June 2016 Volume 27 (6) Leading Edge Technologies for Refining and Fat Modification Plants

IDE: reduced-fat emulsions S ” IN o International News on Fats, Oils, and Related Materials Materials Related Related and and Oils, Oils, Fats, Fats, on on News News International International inform inform Screen Cleaner Als “ replacement Trans-fat detergency laundry Premium minutes beef in 10 10 in beef

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contents 6 Benchtop NMR spectroscopy for meat authentication A rapid screening approach for authenticating beef based on triglyceride composition takes 10 minutes and can be used at key points in the supply chain. Project Cost / Inﬂ uence Curve

MAJOR INFLUENCE MINOR INFLUENCE

HIGH LARGE

Cumulative Inﬂ uence project cost

10 LOW 14 17 SMALL

PLANNING DESIGN/PROCURE CONSTRUCTION START-UP How to get premium laundry detergency 10 A fabric care and cleaning expert explains how using less detergent can actually clean better, save money, and lower environmental impacts.

Ultra-high pressure homogenization for “cleaner” reduced-fat emulsions 14 Can ultra-high pressure homogenization be used to produce sensory-improved reduced-fat emulsions without (or with lower concentrations of) fat replacers?

Front-end loading for a successful capital project 17 Completing the majority of project planning and engineering early costs more upfront but can lower overall costs by making it easier and cheaper to accommodate design changes.

Crystallizers: the crystal-clear answer to trans-fat-free margarine production 22 Learn how the right crystallizer can pay for itself by resulting in better use of production equipment.

Influence of fatty acid composition on properties of industrial products and fuels 28 The fatty acid composition, scientific name, and seed oil content of 25 alternative triglyceride feedstocks—plus the industrial applications of the major fatty acid categories—are summarized in two handy tables. Departments 5 Index to Advertisers Analysis/commentary Publications and more 37 classified Advertising 30 Olio 31 Mintec Update 48 AOCS Meeting Watch 34 Regulatory Review 36 patents 46 latin America Update 38 Extracts & Distillates 41 Book Review 44 AOCS Journal Titles 48 tips from inform|connect Make the Utilize your benefi ts! X AOCS Resource Directory — the most up-to-date contact information for most of your all AOCS members X Inform — a print subscription to the Society’s business and news magazine X Members-only discounts on books, Membership! meetings, technical services, and more X 2 Free AOCS Technical Journal article downloads per year Connect and innovate!

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MemberBenefits-Sep15i.indd 1 7/23/15 5:15 PM 6 • inform June 2016, Vol. 27 (6) Benchtop NMR spectroscopy for meat authentication E. K. Kemsley, M. Defernez, A. D. Watson, and D. Williamson

Nuclear magnetic resonance (NMR) spectroscopy is a well-known technique used in laboratories worldwide. Modern research-grade instruments are based on super-cooled electromagnets that are used to generate the high magnetic fields needed. They are expensive to buy and maintain, occupy a large amount of space, and require highly trained personnel to run them. In recent years, a new crop of low-field NMR spectrometers has appeared on the market. In contrast to their high-field cousins, these instruments are small (often referred to as “benchtop”) and have much lower capital and insignificant running costs. Typically operating at field strengths <100MHz, benchtop spectrometers are based on permanent magnets and work without needing any cryogens. Food sector applications: • In 2013, undeclared horsemeat was detected in a wide starting with triglycerides range of processed meat products on supermarket shelves Since 2012, the Analytical Sciences Unit at the UK’s across the United Kingdom and Europe. The crisis exposed Institute of Food Research (IFR) has been working in shortcomings in testing regimes and highlighted the need partnership with Oxford Instruments (OI), a leading manufacturer of scientific instrumentation, to develop for additional analytical approaches suitable for rapid benchtop NMR spectroscopy for food sector applica- low-cost screening. tions. The project received support from the transla- tional science funding agency, InnovateUK, as well as the Biotechnology and Biological Sciences Research Coun- • Many methods for verifying the species present in cil. The spectrometer at the heart of the project was the PulsarTM, a 60MHz instrument launched by OI in 2013 meat products are DNA-based, but there are other (Fig. 1). compositional factors amenable to measurement which Among the first compound classes targeted were can also provide means of species confirmation. triglycerides, which are the main constituents of the fat component in foods. Triglycerides are ideal samples for study by low-field NMR, as good quality spectra can be • This article describes the development of a rapid screening obtained quickly and easily. To examine fats and oils, samples can simply be mixed with chloroform to reduce approach for authenticating beef based on triglyceride their viscosity, then placed into a standard NMR tube for composition. The screening protocol only takes 10 minutes analysis. 60MHz NMR spectral profiles contain distinct and can be used at key points in the supply chain, such as peaks arising from various moieties (Fig. 2, page 8), from which accurate and precise quantitative information on meat processors or wholesalers, where the incoming raw the mono- and polyunsaturated contents can be calcu- materials are in the form of frozen blocks of trimmings. lated. A first application of this work sought to distin- guish between olive and hazelnut oils, which are highly similar with regards to their fatty acid composition [1]. inform June 2016, Vol. 27 (6) • 7 Analytical advances

FIG. 1. The PulsarTM 60MHz benchtop instrument. To collect a spectrum, an NMR tube containing a liquid sample is introduced into the spectrometer. Data collection is initiated by the operator using acquisition software installed on a PC. Here, the machine is being used to carry out quantitative analysis of edible oils, with the results displayed directly following recording of the NMR spectrum.

To analyze solid foods, an extraction step is needed, approach for authenticating beef. 60MHz NMR spectra were but this can also be relatively simple: shaking a few grams collected from extracts prepared from fresh red meats, spe- of homogenized sample in chloroform, vortexing and filter- cifically beef and two potential adulterant species: pork and ing into the NMR tube is all that is required. Chloroform is horse. an efficient extractor of lipophilic compounds, and using Over the course of a year, the method was refined and this procedure, high quality spectra can be obtained of the repeated on hundreds of meat samples in the laboratories at fat component from a wide range of food products and raw OI and IFR. The results obtained were compelling. Each of the materials [2]. different meats examined exhibited clearly different spectra. For example, in the case of beef versus horse, spectral profiles were found to be entirely distinct. Even allowing for natu- Developing a screening method ral variation, no overlap between the two types was found; for authenticating raw beef the test was completely accurate in determining whether an In 2013, a major incident of food fraud was uncovered, in extract originated from a piece of horsemeat or a piece of which undeclared horsemeat was detected in a wide range beef. Fig. 3, page 8, shows a collection of spectra from the of processed meat products on supermarket shelves across three meat types, along with a graphical representation of the UK and Europe. Thousands of tons of food were recalled, the statistical model built to characterise the beef group. The and there was substantial brand damage to the companies ellipse delineates a confidence interval around the “authentic involved. The crisis exposed shortcomings in testing regimes, beef” group. When challenged with a range of pork and horse and highlighted the need for additional analytical approaches test samples, this model correctly placed all of these outside suitable for rapid low-cost screening. the “authentic beef” group. Many methods for verifying the species present in meat products are DNA-based. However, animals do not differ only Accurate results in 10 minutes in their DNA; there are other compositional factors amena- As part of the project, a stand-alone software package was ble to measurement which can also provide means of species developed to carry out the mathematical analysis of the spec- confirmation. It is common knowledge that pork and beef fat, tra, thereby providing a complete system for authenticating for instance, are very different from one another. This is due raw beef in a screening protocol that takes 10 minutes from to dissimilarities in the animals’ triglyceride compositions, start to finish. The test is intended for use at key points in the which in turn arise from differences in their diets, metabolism supply chain, such as meat processors or wholesalers, where and digestive systems. With this in mind, the teams at IFR and the incoming raw materials are in the form of frozen blocks of OI began an extensive study of the fat component extracted trimmings; it is also suitable for pre-screening ahead of more from raw meats, with the aim of developing a rapid screening 8 • inform June 2016, Vol. 27 (6)

Fig. 2. A typical low-field NMR spectrum of vegetable oil, which is composed largely of triglycerides. Indicated on the figure are some of the key resonances that provide information on the detailed composition of the sample, in particular with regards to the amount and type of unsaturated fatty acid chains.

FIG. 3. Chemometric analysis of key regions of the low-field NMR spectrum (left panel) leads to a simple two-dimensional model in princi- pal component space (right panel), capable of distinguishing beef from pork or horse with complete accuracy across >100 test samples. inform June 2016, Vol. 27 (6) • 9

time-consuming DNA testing. This work was published in an to further fruitful collaboration on industrially important chal- open access paper in Food Chemistry [3], and a patent on this lenges as the technology of benchtop NMR continues to evolve. approach to meat species confirmation is pending. High-field NMR spectroscopy has long been recognized E. K. Kemsley, M. Defernez and A. D. Watson are researchers at as a powerful analytical tool, but the equipment is too expen- the Institute of Food Research, Norwich Research Park, Colney sive and technically demanding to allow deployment anywhere Lane, Norwich, NR4 7UA, UK, http://www.ifr.ac.uk/. apart from specialist laboratories. The advent of benchtop NMR looks set to change this landscape. Through a number of key D. Williamson is a researcher at Oxford Instruments, food sector applications, we have discovered how useful the Tubney Woods, Abingdon, Oxford, OX13 5QX, low-field modality can be, particularly for the analysis of fat- http://www.oxford-instruments.com/. containing samples. The IFR and OI teams are looking forward

Further reading

[1] 60 MHz 1H NMR Spectroscopy for the analysis of edible oils. Parker, T., Limer, E., Watson, A., Defernez, M., Williamson, D., and Kemsley, E.K. TRAC— Trends in Analytical Chemistry (2014) 57: 147–158.

[2] 60 MHz 1H NMR Spectroscopy of triglyceride mixtures. Gerdova, A., Defernez, M., Jakes, W., Limer, E., McCallum, C., Nott, K., Parker, T., Rigby, N., Sagidullin, A., Watson, A.D., Williamson, D., and E.K. Kemsley (2015) in Magnetic Resonance in Food Science: Defining Food by Magnetic Resonance (eds: F. Capozzi, L. Laghi, P.S. Belton) Royal Society of Chemistry pp. 17–30.

[3] Authentication of beef versus horse meat using 60 MHz 1H NMR spectroscopy. Jakes, W., Gerdova, A., Defernez, M., Wat- son, A.D., McCallum, C., Limer, E., Colquhoun, I.J., Williamson, D.C, and Kemsley, E.K. Food Chemistry (2015) 175: 1–9.

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OLFB_inform_June_2016_AOCS.indd 1 4/14/2016 8:37:37 AM 10 • inform June 2016, Vol. 27 (6) How to get premium laundry detergency Floyd E. Friedli

How often do you get a spot on your favorite shirt or blouse and put it in the laundry hamper and forget about it? During the weekly wash you neglect to pre-spot it, leaving your detergent to remove some, but not all of the stain. Then you commit the final mistake and dry it, baking in the stain. We all hate when that happens.

During the past 40 or so years, the surfactants and detergents industry has made massive efforts to improve laundry perfor- • The surfactants industry has made many mance, sustainability, and convenience. Much progress has been product advances to improve laundry made when it comes to developing new more effective ingredients, biodegradable materials, improved enzymes, new formulations, performance and sustainability, but how these new delivery systems, drip-roof caps, and new packaging. products are used affects laundry performance Powdered products have given way to heavy duty liquids (HDL). and sustainability just as much—if not more— Europe has tried tablets, and now in North America pods are the rage. We currently have value brands, mid-tier brands, superior than the products themselves. cleaning brands, color protection brands, skin-sensitivity brands, concentrated brands, super concentrated brands, and oxidizing/ bleaching detergents, as well as pre-spotters that delivery by stick, • Done carefully, pre-spotting improves spray, and liquid. Many of these advances have been covered in performance, uses less detergent, saves Inform. money, and lowers environmental impact. However, over my years in fabric care working on stains in the laboratory and at home, I have observed that how laundry products are used affects laundry performance and sustainability • This article explains the basic chemistry just as much—if not more—than the products themselves. Pre-spotting takes time and effort, but the reality is that behind this approach and why it works. most of us just want to throw a cheap detergent into the washing machine and magically get clean clothes. There are two major problems with this approach. 1. Your detergent might not have the best ingredients for your specific stains and your over-all level of dirt. 2. The available surfactant and polymer molecules are too dilute to actually find the spot on your shirt and remove all of the stain. Fortunately, many times your clothes are not that dirty. Most are slightly soiled with traces of sweat, body oils, food, dirt, and dead skin (basically dust sebum). There may be one or two cloth- ing items with more serious spots of food or grease. So, unless you are washing a load of dirty baseball uniforms or mechanics’ clothes, your detergent has an easy task—except for those one or two problem spots. inform June 2016, Vol. 27 (6) • 11 Surfactants and Detergents

The effects of dilution on dosage Theories Regarding stains, it is no secret that grease is best removed with nonionics, particulates with anionics, some food stains • Most laundry is not that dirty. with enzymes, and red wine with oxidizing agents. Builders and • A few items may have a trouble spot that will only be chelants tie up ions in hard or iron-ontaining water and allow effectively removed with concentrated surfactants placed the surfactants to work better. Polymers help suspend the right on the dirt. removed soils for easier rinsing down the drain before they can • Sorting clothes by color is a waste of time. Why do two redeposit. small loads when you can do one large load with whites Washing machines typically hold 10–28 gallons of water, and colors and try your luck on dye transfer? Use cold water depending on the type of machine and water level chosen to save energy and help avoid dye transfer. (1). This comes to about 38–100 liters of water. The minimum • The time taken to pre-spot is well worth it to avoid concentration needed to get noticeable surfactant activity or washing dirty items a second time or not noticing the cleaning, or Critical Micelle Concentration (CMC), of typical non- item is still dirty and drying it to lock in the stain. ionics is .001–.025% at room temperature (2). A Heavy Duty • Due to improved agitation and lower water usage, which Liquid (HDL) detergent capful dose is about 100 ml (3). Assum- improves the CMC situation, an high-efficiency machine ing HDL are 10–30% solids of which 10–33% are nonionics, you should and does clean better. get about a 3–10 g dose of nonionic in each capful. This dosage gives an “in water” concentration range for the nonionic of .003% –.026% , which is at the CMC in pure water. Again, this My experience in fabric care working on stains resulted level is the minimum needed to get surfactant action and in the development of various theories and procedures cleaning. (see Theories, above, and Friedli’s System on page 12). However, even though the surfactants are dosed at their Pre-spotting has several advantages, “in theory.” CMC and the laundry cycle is long, it is still very difficult for 1. Your clothes come out cleaner, particularly the dirty enough surfactant molecules to find your stain and remove ones. it when dosed in the general water bath. Imagine that you 2. You “may” actually use much less detergent on the have 5 grams of nonionic and 5 grams of anionic that are lost average, by using partial capfuls. in 100,000 milliliters of water. How are they supposed to find 3. Since you are using less detergent, the environmental the stain on your favorite shirt amongst all the other fabric and load you are putting down the drain is much less. washing machine surfaces? The fact that we get reasonable Working for Akzo Nobel Surface Chemistry and get- cleaning most of the time shows the fine surfactant and formu- ting free samples helped the author develop a great pre-spot lation optimization the detergent chemists have accomplished. mix. Not to reveal any secrets, but a blend of a) detergent Pre-spotting overcomes the dilution effect because: range nonionic, b) low-HLB (4) nonionic, c) hard water resis- • the detergent is placed on the spot and not deposited on tant anionic, and d) quality anti-redep polymer works nicely clean fabric or washing machine surfaces; in concentrated form. The low-HLB nonionic is key to grease • the surfactant and solvents in the formulation start to removal, particularly in a pre-spot scenario where the non- soften and dissolve the stain. Hot or warm water also ionic, which has low water solubility and solvent properties, accomplishes this function, but currently we want to softens and starts to dissolve the oily stain. Ethoxlated amines wash in cold water to save energy. (Pre-spotting can be can act as great general nonionics and as grease and grass viewed an alternative to warmer water.) stain removers (5). • Until the surfactant fully disperses, it will be well above From the CMC calculations above, a low-HLB, low-CMC its CMC in the area of the stain to work better to lift and nonionic not only cuts grease, but definitely should be above encapsulate the stain in micelles. its CMC in use.

Test spaghetti Hazelnut-chocolate/olive oil 1 90% removed 80% removed - olive oil ring 2 95% removed 85% removed – very little oil ring 3 95% removed 90% removed – some olive oil ring 4 85% removed 70% removed – olive oil ring

TABLE 1. Wash test results 12 • inform June 2016, Vol. 27 (6)

Practical tests stains, but not as well on the oil ring. Dosage or spot cover- To test my theories, particularly on using less detergent, a age may have been too low. The most disappointing test was “pseudo-scientific study” of two stains—spaghetti sauce and test 4 using the HDL with a pre-spotter in a manner typical chocolate-hazelnut paste diluted 50/50 with olive oil to liquefy of normal laundry when done with pre-spotting. There was it—placed on white 100% cotton T-shirts (6) was undertaken. not enough pre-spotter for the ingredients it contained to do A 1 ml spot of spaghetti sauce and a 1 ml 50/50 mixture an effective job. A few sprays of a dilute pre-spotter just isn’t of chocolate-hazelnut/olive oil was placed on the shirts and enough. So, the recommendation is use a large amount of allowed to dry for 16 hrs. Four washing tests were then per- pre-spotter or just put your HDL on the spot. formed, using one stained shirt and a variety of other normal Since the stains were not removed completely, all the dirty clothes, sheets, and towels in each load. shirts were rewashed using about 5 ml proprietary pre- 1) 60 ml high quality HDL in wash water—~20% solids gives spotter on the stains. With that treatment, the spaghetti 12 grams active ingredients was gone, but traces of the chocolate/hazelnut stain still 2) 30 ml high quality HDL directly on stains—6 grams active remained. Finally, the spots were treated with chlorine ingredients bleach right on the stains and rewashed. By now all the 3) 7 ml proprietary pre-spotter on stains—at 69% actives stains were gone, and the shirts were like new which leads gives 5 gram actives into the next topic. 4) 30 ml high quality HDL in wash water—5 ml commercial pre-spotter on stains—~ 7 grams actives Other options includE Bleach The tests were conducted in a Maytag home washing Some stains are very tough (chocolate/hazelnut spread), machine set to cold wash, medium water volume, and cold ground in, or aged and oxidized. If your fabrics are white, rinse. Stained shirts were removed at the beginning of the spin chlorine bleach is a great solution. Hydrogen peroxide on cycle, and air dried overnight. red wine can work. A high enzyme detergent or pre-spot- Tests 2–4 were designed to see if less overall surfactant ter helps on the right food stains. Again, pre-spotting offers could be used to get good cleaning compared to test 1. In test more success than general dosing particularly if you give the 1, the detergent did better than expected and even removed treatment 10–30 min to work before washing. a small chocolate stain on another pair of khaki pants without Stubbornness has lead the author on multiple occasions pre-spotting. In test 2, using half the detergent, but putting all to use a cotton swab dipped in chlorine bleach to carefully of it on the spots did better and was best at removing the olive treat stains on white fabric in between colored strips on a oil ring that spread out from the chocolate/nut stain. The pro- shirt. Keep water running in a nearby sink in case the bleach prietary pre-spotter used alone in test 3 did the best on the starts to soak near the colored area and you need a quick rinse. Very dilute chlorine bleach is the last desperate solution Friedli’s System for tough stains on colored fabrics. Chlorine bleach comes in 3–9% concentrations. Dilute to about .5% bleach well dis- 1. One load with all colors and articles mixed together persed in water then soak the garment for 10 minutes to an (no sorting), cold water. The exception being “high lint” hour. Make sure all the fabric is under water or at least very items like fluffy towels need to be washed separately. wet. This approach is obviously risky and only to be used when the alternative is to throw away the garment. 2. As you throw the clothes in the washer, quickly check them for spots, stains, or concentrations of dirt. Pre- spot problem areas such as ring-around-the collar on white shirts, grease or spaghetti stains on shirts, par- ticulate dirt on the bottom of khaki pants, and dirty ath- letic socks—especially if they were worn while playing golf or doing yard work. One good option is to put all the detergent on the spots or dirty areas and none in the general water or dispenser. The surfactants placed on the stain will remove that stain, and the leftover surfactants will disperse and find the low levels of soil on the remaining laundry items.

3. Pre-spotting can be done with a premium brand HDL, a bargain liquid, any of the pre-spotters on the market, or the author has his own favorite blend. If you pre-spot, almost anything will work unless the stain is tough. In that case, go to a premium HDL or the author’s blend. inform June 2016, Vol. 27 (6) • 13

The author’s best success was on a yellow cotton golf shirt with thin green strips. Opening a bottle of red wine left little droplets of wine on the shirt. Even immediately washing it with a premium detergent did little, but a two-hour soak with very dilute bleach worked perfectly with no harmful effects at all. Other times this process was partially successful in that the stain was removed, but the overall color of the garment was now different, but at least uni- form in color. This is why it is important to make sure the entire fabric is immersed in the bleach. Pre-spotting takes effort, but is worthwhile. Done carefully, less detergent can be used saving money and lowering environmental impact. Think of it as a way to soften and solubilize the stains, get above the CMC, and take the place of hot or warm water.

Floyd Friedli obtained his Ph.D. in organic chemistry from The Ohio State University. Friedli worked for 24 years at Degussa (originally Sherex, then Witco, then Goldschmidt, then Degussa, now called Evonik) in R&D. He was Technology Manager for Synthe- sis and Fabric Care. He then spent 12 years as an Account Manager for Fabric Care & Cleaning at Akzo Nobel Surface Chemistry. Following retirement from Akzo, he formed Friedli Chemical Consulting LLC (floy- [email protected]) to help companies with surfactant manufacture, surfactant selection, process development, formula optimization and sales/market- ing. Friedli has been a member of AOCS for 37 years and served as an Associated Editor of JAOCS and JSD. Current personal challenges center around a two year-old grandson who is an enthusiastic eater and leaves horrendous stains on shirts and bibs.

More information 1) Whirlpool 2015 data 2) Air Products 2015 Linear Ethoxlate Brochure 3) Actual measurement 4) HLB stands for hydrophilic-lipophilic balance of the nonionic which basically describes the water solubility or dispersibility of an ingredient in water. A low HLB nonionic has low water solubility and tends to associate with oils or organic solvents. 5) Marcel Dekker Surfactant Series Vol 98, Detergency of Specialty Surfactants, Chapter 2. 6) A true laboratory detergency testing sequence would have involved repeating the tests 3–4 times either in a standard washing machine or a Terg-O-Tometer. More dosage levels would usually be tried also. 14 • inform June 2016, Vol. 27 (6) Ultra-high pressure homogenization for “ c l e a n e r ” reduced-fat emulsions Many sauces and dressings are conventionally high in fat. For example, traditional mayonnaise, which is consumed worldwide, contains 75–80 wt% oil. From a technological perspective, the leading role of fat in the structure and sensory properties of emulsions makes it very challenging to reduce or replace fat in such products.

Saioa Alvarez-Sabatel, Ziortza Cruz, Iñigo Martínez de Marañón, and Eduardo Puértolas

Emulsions are dispersions of immiscible fluids. Most sauces and dressings are oil-in-water emulsions (O/W) in which the dispersed • The fat-replacers and other ingredients used to phase, commonly a vegetable oil, is dispersed into an aqueous stabilize low-fat mayonnaise and other reduced- phase in the presence of emulsifying molecules. Their production generally involves the application of mechanical forces (homogeni- fat emulsions may negatively affect sensory zation) to induce oil droplet size reduction and dispersion into the properties. They must also be declared on the continuous water phase. label, which could turn off consumers desiring a Emulsions are by nature unstable systems. Due to the lower density of the oil droplets relative to the aqueous continuous “clean label.” phase, gravity causes the droplets to move upward and form a cream layer during storage. For this reason, the development of long-term, stable, reduced-fat emulsions with adequate textural • Ultra-high pressure homogenization (UHPH) has properties represents an important industrial challenge. Some of been proposed as a way to produce sensory- the most relevant factors influencing emulsion destabilization are improved reduced-fat emulsions without fat the size of the oil droplets, the viscosity of the continuous phase, and the volume fraction of the oil. replacers (achieving a “clean label” solution) Decreasing the size of the droplets and increasing the viscosity or at least with a lower concentration of such of the continuous phase prevent cream layer formation. A reduction in the oil volume fraction diminishes the packaging densities ingredients. of the fat droplets, the viscoelastic properties of the continuous phase, and, consequently, the tendency to cream. Hence, substitut- ing fat with fat replacers and thickening agents is a primary strat- • The first industrial UHPH units (up to 1,000 L/h) egy for enhancing emulsion stability. Such replacement ingredients recently entered the market after demonstrat- increase the continuous phase viscosity, which impedes the upward ing positive results in both pilot- and lab-scale migration of the oil droplets and increases overall viscoelasticity. However, some ingredients, such as xanthan gum, guar gum, and testing, but further work is required to assess inulin, strongly affect the sensory characteristics of foods at the the technology’s ability to structure reduced-fat concentration needed to obtain suitable structural properties. This, together with the industrial trend toward cleaner and simpler labels emulsions at a scale closer to that of industry. has prompted the search for new alternatives. One of the most promising is an emerging technology called ultra-high pressure homogenization (UHPH). inform June 2016, Vol. 27 (6) • 15 High-pressure processing

How does UHPH work? The high pressures (up to 400 MPa) and homogenization forces that are applied during UHPH not only reduce particle size UHPH has some of the same action mechanisms as High Hydro- and change fluid properties, but also inactivate microorganisms, static Pressure (HHP)—although it is important to keep in mind opening the door for pasteurization and homogenization of food that these are two completely different technologies. HHP is liquids in a unique phase (Diels and Michiels, 2006). a batch system in which the applied pressure is evenly distributed throughout the sample. UHPH is a continuous process that combines pressure with homogenization forces, which produces UHPH’s role in structuring effects that are different from those caused by HHP. reduced-fat emulsions UHPH is based on the same principles as conventional homogenization. The process forces a liquid product through a UHPH technology can significantly reduce both oil droplet diam- narrow gap (e.g. nozzle or valve) at high pressure. This sudden eter and size distribution polydispersity which, in turn, increases restriction of flow under high pressure subjects the liquid to very the droplet packing density and emulsion stability (Fig. 2, page high sheer stress, which causes the formation of very fine emul- 16). This was observed in stability tests comparing reduced-fat sion droplets (Fig. 1). In conventional homogenization, the maxi- mayonnaise (down to 35 wt% oil content) that had been struc- mum pressure rarely exceeds 50 MPa, while special designs and tured with and without UHPH. Samples that were structured pressure-resistant materials enable UHPH to apply pressures of without UHPH creamed during the first month of storage, while up to 400 MPa (Alvarez-Sabatel, 2016). Although the energy pro- those that were structured using UHPH remained stable during duced during the process is partially dissipated as thermal energy, the entire length of the six-month experiment (Alvarez-Sabatel, Saioa Alvarez-Sabatel, Ziortza Cruz, Iñigo Martínez de Marañón, and Eduardo Puértolas UHPH is considered a non-thermal technology (Zamora and 2016). Guamis, 2015). Also, the rheological properties of the UHPH-structured sam- During depressurization, different types of homogenization ples changed appreciably due to the increased droplet packing. forces (shear, impact, cavitation, and turbulence, and so on) are The UHPH reduced-fat mayonnaises exhibited textural properties used to reduce particle size and increase process efficiency. The similar to those of traditional full-fat mayonnaises, while the non- magnitude of these forces depends on several processing param- UHPH processed samples behaved like liquids. Processing at vari- eters, including equipment design (impact to valve walls and colli- ous UHPH pressures between 100–300 MPa resulted in stable, sion with other fluids, for example), the applied pressure, and the low-fat mayonnaises (down to 35 wt% oil content) with rheologi- temperature of the incoming fluid. Other properties of an incom- cally different and interesting properties, indicating that UHPH ing fluid, such as its viscosity and the nature of its ingredients and could be used to modulate the final textural properties in a fixed their concentrations, can also affect process efficiency and the emulsion recipe. On the other hand, using UHPH to produce properties of the outgoing fluid. mayonnaise with a fat content lower than 35 wt% resulted in non-acceptable rheological properties regardless of the pressure that was applied. However, this limitation could be overcome by using the technology in combination with fat substitutes, and these two fat-reduction approaches could even produce a syner- gistic effect. UHPH is able to change the technological functionality of some thickening agents that are extensively used as fat substitutes. For example, UHPH improves the gelling properties of inulin, a low-caloric (1.5 Kcal/g) fructoligosaccharide with fiber- like properties (Alvarez-Sabatel, Martínez de Marañón, and Arboleya, 2015). Using inulin, it is possible to produce reduced-fat mayonnaise with as little as 1.5 wt% oil, with long-term stability and relatively adequate texture, but with a poor sensory profile. Applying UHPH (from 100 MPa) could allow the inulin concentration to be decreased by more than the 50%, while maintaining the desirable properties and reducing the described negative sensory profile associated with high inulin concentration (Alvarez- Sabatel, 2016). Independent of the presence of fat substitutes, increasing pressure results in mayonnaises with higher viscoelastic properties. However, above a critical threshold pressure, over-processing phenomena—lower vicoelasticities, creaming, sedimentation, or the immediate separation of the oil and water phases, occur. FIG. 1. Schematic representation of a common UHPH device This critical pressure value varies based on the specific emulsion recipe. 16 • inform June 2016, Vol. 27 (6)

up to 140 and 310 MPa, and up to 2,700 and 1,500 L/h, respectively. The European startup Ypsicon recently launched UHPH equipment that performs up to 350 MPa of 1,000 L/h and is scal- able up to 10,000 L/h. However, to the best of our knowledge in April 2016, neither company had yet constructed industrial units. The price of the smallest industrial-scale units (1,000–3,000 L/h) are around $400,000–700,000. The estimated cost of equipment needed to handle higher flow demanding applications (10,000 L/h) would run between $1,000,000–2,000,000, depending on pressure requirements and annexes. In conclusion, UHPH has strong potential for reduced-fat emulsion structuring, opening the door for designing innovative and healthy liquid foods. The first steps toward industrial implementation have been completed, but further work is required to validate the results obtained at pilot and lab scale on a scale that is close to industrial. In any case, due to the great influence food and ingredient properties have on process efficiency and the characteristics of the final emulsions, industrial application of UHPH requires the process to be optimized for each particular product.

Saioa Alvarez-Sabatel has a Ph.D. and MsC in Food Quality and Safety. Her research is devoted to the impact of emerging food processing technologies on food microstructure, with special emphasis on the technological functionality of food emulsions and ingredients. She can be contacted at [email protected]. Ziortza Cruz has a BSc in Food Science and Technology and an MSc in Pharmacology. She has been involved in more than 50 R&D and transfer projects for the food industry. Her research field is mainly FIG. 2. Visual appearance and confocal laser scanning microscopy focused on emerging processing technologies for preservation and images (CLSM) of control (creamed) and UHPH (stable) reduced-fat the development of new food products. She can be contacted at mayonnaises (52 wt% oil) after six months of chilled storage. In the [email protected]. CLSM images, the oil droplets are red and the rest of ingredients are green. Iñigo Martínez de Marañón has a Ph.D. in Food Science and Tech- nology. He is currently R&D&I Manager at AZTI. He has more than 25 years of experience in Food R&D, mainly related to the study of First steps for industrialization the impact of emerging processing technologies on food quality. UHPH has progressively gained the attention of industry in keep- He can be contacted at [email protected]. ing with the development and scale-up of the systems. During the last 10 years, pilot units (up to 300 L/h) capable of applying Eduardo Puértolas has a Ph.D. in Food Science and Technology. the ultra-high pressures needed to structure reduced-fat emul- He is co-author of more than 40 publications (including 28 peer- sions (100–350 MPa) entered the market. Worldwide, several reviewed papers) and has participated in more than 30 public and have been installed and used for food research and development private projects related to emerging food technologies. He can and demonstration purposes. Most scalability problems have be contacted at [email protected]. been solved during these pilot efforts, and several companies are The authors are with AZTI, Food Research Division, Derio, Spain. beginning to design and commercialize industrial systems. BEE http://www.azti.es/. International advertises two homogenizer models that perform Information

Alvarez-Sabatel, S. (2016). High-pressure homogenization for emulsion fat reduction (Unpublished doctoral thesis). University of the Basque Country, Spain. Alvarez-Sabatel, S., Martínez de Marañón, I., and Arboleya, J.-C. (2015). Impact of high pressure homogenization (HPH) on inulin-gelling properties, stability, and development during storage. Food Hydrocolloids 44: 333–344. http://dx.doi.org/10.1016/j. foodhyd.2014.09.033. Diels, A.M. and Michiels, C. W. (2006). High-pressure homogenization as a non-thermal technique for the inactivation of microorganisms. Critical Reviews in Microbiology 32: 201–216. http://dx.doi.org/10.1080/10408410601023516. Zamora, A., & Guamis, B. (2015). Opportunities for ultra-High-pressure homogenisation (UHPH) for the food industry. Food Engineering Reviews, 7(2), 130–142. doi: 10.1007/s12393-014-9097-4. inform June 2016, Vol. 27 (6) • 17 Project management

Front-end loading for a successful Jens M. Ebert capital project A successful project is not defined solely by whether operational goals were met. In addition to typical cost and schedule constraints, there may also be other success criteria related to safety performance, product quality, sustainability objectives, or implementation of new process technologies to consider.

Front-end loading (FEL) is a phased approach to project execution in which stakeholders make key decisions at the end of each phase about whether, or how, to proceed. • Front-end loading is a phased Each phase advances the project definition to a pre-determined status which generally corresponds to the level of confidence in the project cost estimate, expressed as a per- approach to projects in which centage range around the most probable project value. There are a few variations of most of the planning and this technique, including some which have been customized for use by specific compa- engineering is completed early— nies, but the underlying principles are fairly consistent. Depending on the industry, FEL is also known as pre-project planning (PPP) and front-end engineering design (FEED). when design changes are easier to make and the cost to make them is relatively low.

• This allows stakeholders to make informed investment decisions, and makes it less likely that cost, schedule, or performance issues will arise later.

• A recent analysis of 609 projects showed that proper use of front-end planning reduced overall costs, achieved shorter delivery periods, and resulted in fewer changes. FIG. 1. The influence curve of projects at various stages 18 • inform June 2016, Vol. 27 (6)

Primary Characteristic Secondary Characteristic MATURITY LEVEL OF EXPECTED ACCURACY PROJECT DEFINITION END USAGE METHODOLOGY RANGE ESTIMATE DELIVERABLES Typical purpose Typical estimating Typical variation in low CLASS Expressed as % of of estimate method and high ranges complete definition Capacity factored, Concept L: ‐20% to ‐50% parametric models, Class 5 0% to 2% screening H: +30% to +100% judgment, or analogy Study or L: ‐15% to ‐30% 1% to 15% Equipment factored or Class 4 feasibility parametric models H: +20% to +50% Budget Semi‐detailed unit L: ‐10% to ‐20% authorization Class 3 10% to 40% costs with assembly level H: +10% to +30% or control line items Control or Detailed unit cost with L: ‐5% to ‐15% Class 2 30% to 75% bid/tender forced detailed take‐off H: +5% to +20% Check estimate Detailed unit cost with L: ‐3% to ‐10% 65% to 100% Class 1 or bid/tender detailed take‐off H: +3% to +15%

TABLE. 1. Cost estimate classification matrix for the process industries

The purpose of this structured approach is to give stake- of the underlying project definition and the associated level of holders an opportunity to make informed investment decisions, effort [1]. See Table 1. minimize the associated risk, and maximize the potential for Contingency funds are intended to cover the cost of success. Despite the benefits, it takes discipline to follow this unforeseen variations in design parameters, quantities, unit kind of structured approach and resist the temptation to skip pricing, or execution plans. The amount of contingency ahead. Taking a shortcut may be appropriate in some cases, but included in a project cost estimate is a function of the degree of typically not when there is a significant capital investment at definition vs. the level of uncertainty. stake. On larger projects with more detailed cost estimates, the The best practices associated with FEL are founded on the level of contingency will often be adjusted for each scope area “Influence Curve.” This basic premise is that the majority of to reflect the varying amounts of uncertainty. The compos- project planning and engineering should be completed early in ite value across the entire estimate should still correlate with a project—when the ability to accommodate design changes is the expected accuracy ranges shown above. Therefore, as the still relatively high, and the cost of making those changes is still project definition increases, the contingency decreases. This, in relatively low (Fig 1, page 17). turn, reduces the amount of capital allocated to risk manage- The FEL process, as the name clearly indicates, intentionally ment. This additional capital is now available for other invest- moves some investment to the early part of the project. This ments, as opposed to being sidelined throughout the entire adds additional cost upfront, but that cost is typically minor project (Fig. 2). compared to the potential additional cost and schedule penalty An FEL program typically uses a stage gate process in which associated with corrective changes later in the project—espe- the project must pass through several formal steps, or “gates,” cially when construction work has started. at well-defined milestones before any funding is released to By extension, the more completely a project is defined proceed with the next phase. Each gate will typically include upfront, the less likely it is to experience cost, schedule, or per- a thorough stakeholder review of all aspects of the design to formance issues later, due to the greater accuracy of the cost ensure that the various success criteria will still be satisfied. estimate and supporting documentation. AACE (Association for The project team should be aligned before requesting any the Advancement of Cost Engineering) International published additional funding from senior management. a widely referenced recommended practice for a cost estimate classification system which assigns an expected accuracy range for each of five different estimate classes based on the quality inform June 2016, Vol. 27 (6) • 19

FIG. 2. Example of the variability in accuracy ranges for a process industry estimate

The risks of moving forward Gateway to success without a gated process The most common form of the FEL process contains three In the fats and oils industry, the risks commonly connected to “gates” that must be passed through before proceeding with any project include meeting cost and schedule commitments, but detailed project execution and start-up. Passing through each more importantly, they also include the risks associated with pro- gate requires the completion, presentation, and approval of spe- ducing poor-quality or unsafe product. This possibility demands cific activities (Fig. 3, page 20). the appropriate level of due diligence in project execution at all FEL I: Conceptual engineering / financial feasibility levels. At the same time, the project life cycles in our industry often The purpose of the first project phase, often called FEL I, is to pre- reflect the pressure associated with meeting promises to inves- pare a conceptual basis for making an informed decision about tors for quarterly earnings results. Under these circumstances, the project’s viability and whether or not to pursue it. Depend- the temptation to push ahead can be irresistible. However, the ing upon the size and complexity of the project, this stage can companies that most consistently deliver successful projects typically take approximately three to four weeks. Emphasis is have mastered the ability to slow down at the placed upon establishing the business case, defining criteria for beginning and to plan appropriately before proceeding success, and developing the scope of work required to achieve with execution. those goals. The criteria for success must establish how the project will positively impact the business. The business case, of course, documents the project’s financial benefit. The scope of work supports a preliminary cost estimate, which will typically have accuracy limitations due to the need for numerous assumptions at this stage. 20 • inform June 2016, Vol. 27 (6)

STAGE GATE PROCESS

FEL I FEL II FEL III Execution Start-Up

Conceptual Prelim Design Detail Design Final Design CQV

Expense Pre-Spend Pre-Spend Capital and Capital and Capital Capital Expense Expense 50% 25% Budget and Budget and Contingency Contingency

10%

Freeze Capital Scope Approved

FIG. 3. The stage gate process

While an FEL I package is generally based upon preliminary commitment within a much narrower range. The cost estimate is information, getting it right lays the foundation for subsequent refined to an accuracy range of approximately +/- 25%. successful FEL phases. One factor that can significantly affect the In addition, the final FEL II package will typically include a level of effort required is the accuracy and availability of docu- milestone schedule as well as a procurement strategy, specifica- mentation regarding existing conditions. If the information is tions for long lead equipment, and a preliminary start-up plan to not available, it usually leads to simplifying assumptions (about establish requirements for commissioning, qualification, and the adequacy of electrical power or other utilities, for example), verification. which may not be valid. A well-executed FEL II can produce dramatic cost savings. During a recent project for the design of a cereal production FEL II: Preliminary engineering / financial justification line, the conceptual design of a complex dust collection system Approval of the FEL I package allows for the project to proceed included 10 stainless steel platforms for equipment access. through the first gate into the FEL II phase. The critical element The 30–40 foot-long platforms would span over five conveyor of the FEL II phase is to formalize the project scope. There may systems, and each one would require 10 handrail gates. still be some synchronous opportunities to evaluate, but very Determined to simplify the overall design before freezing the limited alternatives to the design basis upon completion. scope, the engineering team modified the ductwork layout and FEL II begins after the preliminary business case has been blast gate locations. This relatively simple change made it possi- presented to senior management, which will determine whether ble to eliminate seven of the platforms and cut $471,640 from to authorize funding to proceed into the next phase. Depending the construction budget. upon the scope of the project, the FEL II phase may take anywhere from one to three months. FEL III: Basic engineering / financial budget The primary objective of the FEL II phase is to “freeze” the A completed FEL III concludes the capital appropriation request project’s scope and eliminate many of the assumptions and risks process with the submission of supporting documentation to identified during FEL I. Other important activities in this phase senior management and approval committees. include the assignment of an overall project manager, assembly During this phase, the level of engineering definition is gen- of a project team, and the identification of key stakeholders who erally between 30% and 50% complete. The overall time frame should (but without a structured program, often don’t) partici- for common process industry projects is two to five months, pate in project development. depending heavily on project complexity. The overall project FEL II also moves the engineering design ahead to a point execution plan should be well-defined at this point, including the where it becomes possible to validate the business case, identify establishment of an overall project schedule with a critical path and quantify key risks, and forecast the necessary capital logic worked out, a finalized cost estimate, and the associated financial modeling. inform June 2016, Vol. 27 (6) • 21

The start-up plan developed during this phase includes sup- In the processing industries, engineering design typically plier and operations staffing requirements, materials planning, accounts for 7%–15% of the total project value, depending on final definition of success criteria, and a schedule for the com- a wide variety of factors. For example, assuming a project fore- missioning, qualification, and verification (CQV) phases of the cast at $8 million with approximately 10% for professional ser- start-up. These activities require lots of planning and coordina- vices, the total fee would be around $800k. If the FEL process tion among the stakeholders to be successful. required an investment of 40% of that amount, that would be Often, the FEL III phase will provide fewer opportunities $320k, or just 4% of the overall project value. In fact, the FEL for cost savings since the basic project scope has already been process is typically identified as 2%–5% of the typical project’s established, and a relatively well-developed design is only being total installed costs. further refined. Any savings in this phase is more likely to be On the other hand, poorly defined engineering, scope related to risk reduction that comes with increased definition. omissions, incomplete estimating, unplanned downtime, and Major design alternatives should have been vetted during FEL extended start-ups can quickly and easily account for 3% of the II. Nevertheless, FEL III can still wring significant costs from the total installed cost. For this reason, following the FEL process project. becomes a low risk and cost effective approach. One area of opportunity for cost savings at this stage is in In fact, using the FEL process can benefit a project by low- the development of the construction strategy. An example of ering the overall cost—often by as much as the costs of execut- this came up recently in a food plant project which required ing the FEL process itself. the complete demolition and replacement of an upper level According to a 2009 survey whose results were published concrete floor—with minimal impact on operations. The engi- in the CII Best Practices Guide: Improving Project Performance neering team, in conjunction with the contractor, developed [2], owners using front-end planning spend on average 8% less a strategy to implement suspended truss forms which did not than owners who never or infrequently use this method. This require support posts from below. The forms could be relo- result is quite significant when expressed in terms of a large cated to install the new floor one bay at a time, with little to no company’s annual capital plan. interference to the existing plant operations on the lower lev- A separate study of front-end planning benefits conducted els. This solution avoided the removal of process equipment by Research Team 213 of the Construction Industry Institute that would provide the shoring support required by a more typ- reviewed a sample of 609 projects with a projected total value ical forming approach. By figuring out the construction strat- of $37 billion. The analysis indicated that proper use of front- egy during the FEL III phase of the project and including all the end planning resulted in 10% less total cost, 7% shorter delivery appropriate stakeholders, the owner avoided approximately periods, and 5% fewer changes. one month of production down time. Jens Ebert is a senior project manager and senior associate at Cost–benefit analysis SSOE Group. Jens has over 26 years of experience in the field of consulting engineering for clients in the food/beverage, Implementing the FEL process throughout capital appropria- industrial, nutraceutical, and defense sectors. Many projects tion and into a project control budget (+/- 10%) may require have included developing new and unique technologies and 35%–50% of the overall engineering budget. While hardly an products for the market. Jens can be reached in SSOE’s St. Paul, insignificant commitment, this figure ensures that the owner, Minnesota (USA) office at +1. 651.726.7672 or by email at contractors, vendors, and suppliers all have the information [email protected]. necessary for good planning, estimating, and project execution.

Resources

[1] Association for the Advancement of Cost Engineering (AACE), Recommended Practice No. 18R-97: Cost Estimate Classification System (www.aacei.org).

[2] Construction Industry Institute (2012), CII Best Practices Guide: Improving Project Performance, Implementation Resource 166–3, Version 4.0, (www.construction-institute.org). 22 • inform June 2016, Vol. 27 (6)

Crystallizers: the crystal-clear answer to trans-fat-free margarine production Anders Mølbak Jensen No trans fats on your new ingredients list? Congratulations: Life as a production manager at a margarine manufacturer is about to get much more interesting.

Partially hydrogenated oils have long enabled margarine to step up to the plate, forming more stable products and supporting mouth-feel to deliver an eating • Producing high-quality marga- experience not far from that of butter. Their positive effect on shelf-life is well-documented, too. rine without partially hydroge- Without trans fats, it’s much more difficult to consistently produce high- nated oils is challenging. Every quality margarine. In fact, every part of the production process becomes more part of the production process sensitive to a variety of factors that were comfortably, even transparently, handled by partially hydrogenated oils in the past. becomes more sensitive to a variety of factors, requiring Higher melting point significant changes in produc- One such factor is the higher melting point of other fat types. For optimum flavor release, it’s best to use fats that melt at approximately mouth tempera- tion parameters. ture: around 35 oC (95 oF). In the old world, trans fats fit the bill perfectly. In the new one, the only economically feasible, readily available fat type is palm oil, • For example, the slower fractions of palm oil, or interestified fat types. That said, the melting point of palm oil is still a little higher than that of trans crystallization speed of trans- fats, and it lacks comparable functionality. fat alternatives can reduce The melting point of a fat isn’t just important for the consumer’s eating experience, it also affects the ability of manufacturers to work with the fat production capacity, create during the production process. In a trans-fat-free world, you get a mixture of build-up on tube chiller shafts, high-melting-point fractions and liquid oil, resulting in a higher melting point and a tendency toward softer products. and result in a more brittle Perhaps the most important phenomenon for margarine manufacturers to product that may also be more consider, however, is the slower crystallization speed of trans-fat alternatives. sensitive to recrystallization when subjected to storage The effects of slower crystallization Much has been done to address slow crystallization but realistically, manufac- temperature variations. turers are simply unable to produce as much margarine from the same production lines as before. Process parameters, including machine settings, must be adjusted to cope with the slower crystallization, requiring investments in new • This article examines how tube chillers or the use of two machines where only one was needed before. crystallizers can be used to Whichever route is chosen, final product quality just isn’t the same as it was with address such production issues. trans-fat-containing recipes. Without trans fats, margarine begins to crystallize on the tube chiller shaft, reducing production capacity by perhaps 20% from morning to afternoon, as there is gradually less volume to work with. Flushing the tube with heat to restore capacity is one way to fix the problem, but has its own set of drawbacks and can’t be recommended. inform June 2016, Vol. 27 (6) • 23 Trans-fat replacement

Lower production capacity is one effect of slower crystal- properly examine the role played by emulsifiers in relation to lization. Another is that, due to the slower crystallization speed crystallization, and make recommendations to margarine man- of alternative fats, crystallization continues to develop for ufacturers based on our findings. We set the bar high: Our tests longer than the usual 24 or so hours during pre-storage. This would be conducted with one of the most difficult beasts in the changes the structure of the product over an extended period business—puff pastry margarine. of time, so you’re likely to end up with a more brittle product. Because storage has a much greater effect on the final product, storage temperature variations introduce further sensitivity to What affects crystallization in recrystallization. margarine and shortening? Consequently, pre-storage, which was rarely the focus of When chilling begins in the margarine production process, a margarine production process in the good old trans-fat days, there are initially no crystals. Then the first crystals appear, Anders Mølbak Jensen suddenly takes on new significance with respect to product creating a “seat” for more to build upon, finally arriving at a quality. Now, manufacturers must focus on controlling pre- much firmer mass. This firmness needs to be broken down storage during the first 5 to 7 days following production, mak- somewhat, restoring plasticity. ing pre-storage part of the overall production process. For To tackle this problem, we used one of our pilot plants to example, an attempt might be made to reduce brittleness and start the seating earlier in the process. This allowed the prod- ensure consistency by varying pre-storage temperatures from, uct to spend more time in the machine to reduce post-crystal- o o say, 21 C for the first five days then reducing it to 16 C there- lization time. Longer time in the equipment, however, resulted after. One implication for many manufacturers is the need to in greater effect from the pin machine and the following tube invest in pre-storage facilities that can enable the required chillers, resulting in a quite different product. temperature control. In our trials, we compared hydrogenated, interesterified, Slower crystallization, therefore, is a manufacturer’s night- and non-hydrogenated fat in puff pastry margarine. Hydroge- mare, imposing both immediate limitations on total produc- nated fat, as might be expected, performed best, crystallizing tion capacity and gradually reducing capacity during production days due to crystallization buildup on chiller shafts. Non-hydrogenated products will have a slower crystallization speed, and interestified products have a tendency to become overworked and very soft.

In-step AIDS With widespread attention on the ill effects of trans fats, US food manufacturers and their European counterparts now need to come up with trans-fat-free recipes that give margarine’s batch-by-batch quality the best possible chance of success. According to Palsgaard’s applied research and extensive experience in the European market, that particular “something” is most likely to be carefully concocted combinations of crystallizers and emulsifiers. Crystallizers can do much to ease the production process. However, they will not have significant influence on the longer- term storage phase, during which polymorph structure will make for a firmer margarine over time. This is something that manufacturers must give special attention to when developing trans-fat-free strategies.

trans-free production strategies To understand why crystallizers are the toolbox of choice for food manufacturers facing the trans-fat ban, we first needed to gain a better understanding of crystallization processes in margarine oils and fats. We were particularly keen to find out how various process parameters affected the speed and nature of crystallization. Equipped with this knowledge, we could then 24 • inform June 2016, Vol. 27 (6)

TRIVIAL NAME MELTING POINT TRIVIAL NAME MELTING POINT

C12:0 Lauric acid 44.4°C (112°F) Trilaurin 46.1°C (115°F)

C14:0 Myristic acid 54.4°C (130°F) Trimyristin 55°C (131°F)

C16:0 Palmitic acids 62.7°C (145°F) Tripalmetin 65°C (149°F)

C18:0 Stearic acids 69.4°C (157°F) Tristearin 72.2°C (162°F)

C22:0 Bebenic acids 80°C (176°F) Tribehenic 82.2°C (180°F)

C18:1 n-9 cis Oleic acid 16.1°C (61°F) Crystallizer : C22 –C18 61.1°C (142°F)

C18,1 trans Elaidic acid 43.8°C (111°F) Crystallizer : C16 –C18 57.2°C (135°F)

C18:2 n-6 cis Linoleic acid - 6.6°C (20°F) Crystallizer : C16 –C18-C22 58.8°C (138°F)

C18:3 n-3 cis Linolenic acid 12.7°C (9°F) Crystallizer : C18 72.2°C (162°F)

TABLE 1. Melting points of fatty acids, triglycerides, and crystallizers quickly. Much slower to crystallize, non-hydrogenated fats such right place on the chain requires more than a little expertise! With as palm oil clearly performed worst. In fact, both before and these acids in the right positions, however, the melting point can be after the pin machine it was hopelessly overworked, and would brought down to as little as 66 oC instead of, for example, 82 oC. be difficultto pack or, for that matter, to eat. The interesterified fat medium crystallized well, but again was all too easy to Crystallizing effect of crystallizer overwork. compared with tribehenate Using tribehenate Mp, with its 82 oC (180 oF) melting point, speeds Crystallizers: the solution of choice up crystallization greatly in comparison with our reference (40% At Palsgaard, we’ve determined that the most effective strategy palm oil, 40% palm stearin, and 20% liquid soybean oil without is to use crystallizers as a trans-fat-free “remedy.” crystallizer), as can be seen in Fig. 1. These crystallizers can be, for example: The Mp crystallizer we tested almost matches tribehenate Mp’s • high in behenic acid (C22) and stearic acid (C18); speed, but with a lower melting point of 61 oC (142 oF). Both solu- • high in stearic acid (C18) and palmitic acid (C16); tions far outstripped the performance of the reference. The tests • very high in stearic acid (C18); or also revealed that using crystallizers forms more beta prime crystals, • a mixture of behenic acid (C22), stearic acid (C18), and which have a better absorbing effect than other crystal types. palmitic acid (C16). The melting points of various fatty acids, triglycerides, and crystallizers can be seen in Table 1. A key aim is to determine a crystallizer whose melting point makes it easy to use in production. This can be achieved with stearic acid (18), combined with behneic acids. Tribehenic and monobehenics have the most extreme melting points for crystallizers. At 180 oF (82.2 oC), they cannot be handled in a normal production environment. If a pipe were to become blocked, for example, things would become very problematic. Despite this, and in the name of thorough research, we did attempt to use this acid in various recipes, but achieved the same or better results with other products. Other triglyceride compositions, on the other hand, with behenic acids can produce a lower melting point, making them easier to handle in production. Any of these acids can easily purchased, but constructing these triglycerides—using high melting point behenic acids yet ending up with something that has a significantly lower melting point—is no walk in the park. Locating the behenic acids in the FIG. 1. Crystallizing effect of crystallizer compared with tribehenate inform June 2016, Vol. 27 (6) • 25

TRIAL 3 TRIAL 4 TRIAL 5 TRIAL 8 TRIAL 9 TRIAL 10

Oil blend: Palsgaard® 6111 1.70% 1.70% 1.70% 0.00% 0.00% 0.00%

Palm stearin 40.00% 42.00% 45.00% 40.00% 42.00% 45.00%

RBD. palm oil 40.00% 42.00% 45.00% 40.00% 42.00% 45.00%

Liquid soya oil 6°C 18.30% 14.30% 8.30% 20.00% 16.00% 10.00%

100% 100% 100% 100% 100% 100%

Melting point: 56.20% 56.90% 56.20% 51.70% 50.80% 52.80%

Avr. SFC % 10°C/50°F 61.90% 63.00% 67.20% 52.00% 55.40% 59.80%

Avr. SFC % 20°C/68°F 50.00% 51.70% 54.80% 40.20% 42.00% 43.90%

Avr. SFC % 30°C/86°F 31.70% 32.20% 34.20% 21.00% 22.40% 24.80%

Avr. SFC % 40°C/104°F 21.00% 21.80% 22.70% 12.40% 13.00% 13.90%

TABLE 2. SFC values in puff pastry margarine blends with and without crystallizer

SFC values with/without crystallizer crystallization was strong, quickly getting the seating in Moving on with our exploration, we examined more or less the place upon which to build further crystals. Judging by the same puff pastry margarine recipe as in the previous trials, this time SFC values in Table 2, crystallizers have a strong effect on adding 1.7 grams of crystallizer. We were keen to determine the fat crystallization because they activate some of the fats to Solid Fat Content (SFC) values that resulted from this addition. These crystallize more quickly than would otherwise be the case. o o are depicted in Table 2. With other test methods, 24 to 48 hours at 0 C (142 F) The trials demonstrated a somewhat surprising result: While would have been required to do this. 1.7% crystallizer is not a large portion of the recipe, its effect on New Release Handbook of Lipids in Human Function Edited by Ronald Ross Watson and Fabien De Meester December 2015 | ISBN 9781630670368

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Crystallizers and puff pastry Margarine produced for incorporation into puff pastry is very thin when first made, expanding in the oven to arrive at the mouth-feel loved by consumers all over the world. Seen from a puff pastry expansion point of view, trials with Palsgaard’s crystallizers produce a very stable margarine. No matter how hard we work the product, it still performs well in this vital regard. But we were curious to learn what might happen if we were to conduct a baking test on the final product itself. So we mea- sured the effect on ten such pastries of increasing crystallizer dosages from zero to 2%, switching between three different rotation speeds. Normally, rotation speed isn’t a parameter most production staff can work with. Often, that’s because most production machinery has a fixed speed—or enables switching only between one or two levels. Now however, in a trans-fat-free landscape, the ability to adjust rotation speed in combination FIG. 2. The effect of crystallizer doses on production capacity with various dosages of crystallizers has become a key factor for achieving the right result. Crystallizers and capacity In Fig. 5, rotation speed strongly affects expansion results, Next up, we took a closer look at the effect of crystallizers on performing best at around 11 rpm. Introducing crystallizers production capacity. Fig. 2 shows the results of testing a similar smooths out the effects of rotation speeds, enabling a good puff pastry margarine recipe to that used in our other trials. expansion result not only with different process parameters We tested two production capacity levels, each with and but also on different machines—expansion simply becomes less without crystallizers added. In Fig. 2, the pilot plant’s bar pressure sensitive to process parameter variations. There is, of course, indicates that crystallization is occurring. When producing at low production machinery that can arrive at comparable results capacity (40%), the fat has time to crystallize by itself. But at higher without any addition of crystallizers, but few manufacturers capacity (above 70%), low bar pressure shows the fat is more liquid have invested in the up-to-date equipment that can do it. and crystallization is less effective. At low capacity, fast-crystallizing fat types can produce crys- Are crystallizers aways necessary? tallization, but it requires crystallizers to be added to increase con- It is possible to create recipes that perform just as well as—or tact and result in sufficient crystallization both at higher and lower at least comparably—to the performance of a trans-fat-con- capacities. taining formulation. For example, cake margarines that use As a general conclusion, it seems that the more crystallizers fast-crystallizing fat types such as palm oil or coconut oil fat you add, the higher the bar pressure and therefore the better you have nothing to be gained by adding crystallizers. But with can maintain or increase capacity. Without adding crystallizers, you cheaper fat types, small amounts of crystallizers can make a would need to reduce capacity, allowing the blend to remain in the significant difference. tube chillers for longer. So, while adding crystallizers will increase However, in replacing trans, there is no way to avoid recipe costs, there’s a worthwhile trade-off in better utilization of spending some amount of additional funds—and, for most, the production equipment. costs will be high. Manufacturers will need to take a look at Still in our experimental corner, we decided to look more their equipment line-up. Most likely, older machinery won’t be closely at the effect of different crystallizer dosages on production enough to maintain current capacity and product quality on the capacity, moving from zero to 0.5%, 1%, 1.5%, and, finally, right up new, trans-fat-free playing field—not without applying crystal- to 2%. To make things more interesting, we simultaneously tested lizer dosages as high as 2%. the effect of two different rotation speeds: 400 and 800 rpm In Figs. 3 and 4, the colored bars represent the four tube chillers in our pilot lab production setup. It came as no surprise, of course, that the viscosity needed for margarine required The effects of trans fatty acid reduction more energy toward the end of the production line. We also confirmed that applying crystallizers does indeed increase • Higher melting point viscosity by the end of the process, but the difference they • Slow crystallization of the fat types make is nothing extraordinary. • Easier to overwork the fat product • Post crystallization • Change structure over time • Storage: more sensitive to temperature variations inform June 2016, Vol. 27 (6) • 27

Upgrading opens the door to new and better technologies that may, for example,

enable the use of CO2 as a more efficient and effective cooling medium. But even after upgrading to more modern equipment, manufacturers should still expect to incorporate from 0.5 to 1% crystallizer content in their recipes.

A tough journey For European manufacturers who have been battling the effects of low or no-trans-fat recipes for quite some years now, it’s been a tough journey. The only comfort, perhaps, was the fact that everyone was in the same boat. Product quality decreased across the entire industry, and everyone needed to come up with their own answer to the problems. In the United States, things are about to heat up but there’s much to be learned FIG. 3. The effect of crystallizer doses at 400 RPM from the experiences of their European com- petitors. The days of pouring in ingredients, set- ting the machines, and retreating to the comfort of the control room are most likely over. Even minor fluctuations in production require active—and proactive—efforts, and the producers of puff pastry will be affected the most. Those who succeed in this new reality will develop new production strategies, experiment with crystallizers and emulsifiers in their recipes, and prepare for significant capital investments in equipment. The sooner these efforts are made, the lower the overall cost of the necessary transition to trans-free-products—and the smoother the journey for both manufacturers and their FIG. 4. The effect of crystallizer doses at 800 RPM customers—will be.

Anders Mølbak Jensen, is Product & Application Manager, Lipid & Fine Foods at Palsgaard A/S, Juelsminde, Denmark. Before joining the company 16 years ago, he held various roles as a laboratory, quality control and R&D manager at a large margarine producer for 10 years. Jensen holds an M.Sc in food science and technology from the University of Copenhagen, and a Bachelor of Commerce, IT. He can be reached at [email protected], or 011 +45 7682 7682. More information is available at www.palsgaard.com.

FIG. 5. The effect of different process parameters on puff pastry expansion 28 • inform June 2016, Vol. 27 (6) inform June 2016, Vol. 27 (6) • 29 FATTY ACID

Influence of fatty acid composition on proper ties of industrial products and fuels Fatty acid composition, scientific name and seed oil content of 25 alternative triglyceride feedstocks Latin binomial Seed oil C14:0 C16:0 C16:1 C18:0 C18:1 C18:1 C18:1 C18:2 C18:3 C20:0 C20:1 C20:1 C22:0 C22:1 C22:2 C24:1 Others (wt %) ∆9 ∆6 ∆9 D11 ∆9 ∆12 ∆9 ∆12 ∆15 ∆5 ∆11 ∆13 ∆5 ∆13 ∆15 Ailanthus Ailanthus altissima 11 — 3.5 0.3 1.4 — 35.9 4.2 54.0 0.4 — — — — — — — 0.3 Ailanthus Anise Pimpinella anisum 17 8.2 3.9 0.4 0.9 55.0 7.4 1.4 20.1 0.1 0.1 — 0.2 0.1 — — — 2.2 Anise Arugula Eruca vesicaria 27 0.1 4.3 0.3 1.2 — 15.4 1.1 8.3 12.5 0.8 — 9.7 0.9 41.7 — 1.6 2.1 Arugula Black bean Phaseolus vulgaris 2 0.1 10.7 0.3 1.8 — 9.3 1.9 31.1 41.7 0.5 — 0.2 0.5 — — — 1.7 Black bean Camelina Camelina sativa 31 0.1 6.8 — 2.7 18.6 1.1 19.6 32.6 1.5 — 12.4 0.2 2.3 — — 2.1 Camelina Coriander Coriandrum sativum 27 — 5.3 0.3 3.1 68.5 7.6 1.0 13.0 — ————— — —1.2Coriander Corn DDGs Zea mays 10 — 12.6 — 2.5 — 27.9 0.9 54.9 1.2————— — — 0Corn DDGs Cress Lepidium sativum 23 0.1 9.4 0.3 2.8 — 30.6 1.4 7.6 29.3 2.3 — 11.1 0.6 3.0 — — 1.5 Cress Cumin Cuminum cyminum 10 12.7 3.1 0.3 0.7 46.5 5.2 1.2 26.6 0.2 0.1 — 0.1 — — — 0.1 3.2 Cumin Fennel Foeniculum vulgare 22 — 4.1 0.4 1.1 69.2 13.9 — 10.0 0.2 0.3 — — — — — — 0.9 Fennel Field pennycress Thlaspi arvense 36 — 2.4 — 0.2 — 11.0 1.2 19.5 8.9 2.2 — 10.2 0.2 36.2 — 3.6 4.4 Field pennycress Great Northern Phaseolus vulgaris 2 0.1 11.5 0.2 2.0 — 5.2 1.8 33.4 42.8 0.5 — 0.1 0.5 — — — 1.9 Great Northern Hazelnut Corylus avellana 59 — 5.1 0.4 2.1 — 76.9 1.4 13.1 0.2 0.2 — 0.3 — — — — 0.4 Hazelnut Indian cress Tropaeolum majus 8— 0.6 — — — 3.0 0.2 0.2 0.4 — — 18.7 — 74.9 — 1.4 0.6 Indian cress Kidney bean Phaseolus vulgaris 2 0.1 12.3 0.3 1.4 — 9.5 2.6 24.1 46.0 0.5 — 0.2 0.7 — — — 2.3 Kidney bean Meadowfoam Limnanthes alba 31 — 0.6 — 0.2 — 1.0 — 0.9 — 0.8 64.2 — 0.2 10.2 18.9 0.6 2.4 Meadowfoam Moringa Moringa oleifera 35 — 6.5 — 6.0 — 72.2 — 1.0 — 4.0 — 2.0 7.1 — — — 1.3 Moringa Osage orange Maclura pomifera 25 0.1 7.0 0.1 2.4 — 11.9 0.8 76.4 0.4 0.6 — — — — — — 0.3 Osage orange Peanut Arachis hypogaea 45 — 6.7 — 2.3 — 78.2 0.7 4.4 — 1.2 — 1.9 2.6 — — — 1.9 Peanut Pinto bean Phaseolus vulgaris 2 0.1 12.7 0.2 1.7 — 5.9 1.7 32.1 43.3 0.3 — 0.1 0.4 — — — 1.5 Pinto bean Seashore mallow Kosteletzkya pentacarpos 22 — 24.2 0.6 2.0 — 14.0 0.7 48.7 — 0.8 — — 0.3 — — — 8.7 Seashore mallow Shepherd’s purse Capsella bursa-pastoris 27 0.1 9.2 0.4 3.9 — 14.2 2.1 20.5 32.4 1.6 — 10.0 1.3 1.4 — 0.2 2.7 Shepherd’s purse Upland cress Barbarea verna 24 — 3.0 0.2 0.4 — 17.6 1.1 21.5 6.0 0.4 — 7.3 0.3 36.8 — 1.8 3.6 Upland cress Walnut Juglans regia 60 — 7.2 — 2.6 — 15.1 0.8 60.7 12.8 — — 0.2 — — — — 0.5 Walnut Wild Brazilian Brassica juncea 38 — 2.5 0.2 0.8 — 9.2 0.9 15.5 11.1 0.8 — 7.7 0.9 44.1 1.9 4.4 Wild Brazilian

Major fatty acid categories and their industrial applications What makes one feedstock suitable for a particular To investigate this premise, researchers at the What makes one feedstock suitable whereas those containing high amounts These two summary tables of their Typical Advantages Disadvantages Industrial Traditional Selection Alternative feedstocks industrial application, while another is not? Could it US Department of Agriculture–National Center for examples applications feedstocks criteria for for a particular industrial application, of saturated FAs find applications in results are from a poster, “Fatty acid be differences in fatty acid (FA) composition? Agricultural Utilization Research (USDA–NCAUR) in this study while another is not? Could it be differ- soaps, cosmetics, and detergents—or profile of 25 plant oils and implications Saturated FAs have high oxidative stability but poor Peoria, Illinois, USA, determined the fatty acid (FA) SFAs C10:0 Oxidative stability Melting point Soaps Animal fats > 20% Moringa ences in fatty acid (FA) composition? why biodiesel, lubricants, and plasticiz- for industrial applications,” presented at C12:0 Low iodine value Viscosity Detergents Cocoa butter Seashore mallow low-temperature properties; they also lack a double profiles of plant oils extracted from 25 alternative Saturated FAs have high oxidative ers are typically prepared from vegeta- the 2016 AOCS Annual Meeting & Expo C14:0 Cetane number Functionality Surfactants Coconut bond on which to perform chemical modification. Poly- feedstocks, then used these profiles to determine the C16:0 Palm & palm kernel stability but poor low-temperature ble oils containing a high percentage of in Salt Lake City, Utah, USA, May 1–4, unsaturated FAs, on the other hand, exhibit the opposite most suitable application(s) for each oil. C18:0 Rice bran properties; they also lack a double bond monounsaturated FAs. by Bryan Moser, a research chemist at behavior, while monounsaturated FAs strike a balance These two summary tables of their results are from MUFAs C16:1 Acceptable balance Does not Biodiesel Canola > 40% Ailanthus Cumin Meadowfoam on which to perform chemical modi- To investigate this premise, USDA–NCAUR. Large, printable versions C18:1 of stability, melting excel in any Lubricants Olive Anise Fennel Moringa between oxidative stability, cold flow properties, and a poster, “Fatty acid profile of 25 plant oils and implica- fication. Polyunsaturated FAs, on the researchers at the US Department of both tables are available at [POST IN point, viscosity and one particular Hydraulic fluids Soybean Arugula Field pennycress Peanut chemical functionality. Perhaps this is why paints, var- tions for industrial applications,” presented at the 2016 functionality category Sunflower (HO) Coriander Hazelnut Upland cress other hand, exhibit the opposite behav- of Agriculture–National Center for inform|connect; ADD link here]. The nishes, and coatings are prepared by chemically modi- AOCS Annual Meeting & Expo in Salt Lake City, Utah, Cress Indian cress Wild Brazilian ior, while monounsaturated FAs strike Agricultural Utilization Research (USDA– FA profiles of more than 560 oils, fats, fying vegetable oils enriched in polyunsaturated FAs, USA, May 1–4, by Bryan Moser, a research chemist at PUFAs C18:2 Melting point Oxidative Paints & Corn > 40% Ailanthus Kidney bean Shepherd’s a balance between oxidative stability, NCAUR) in Peoria, Illinois, USA, deter- and waxes can be found in Physical and whereas those containing high amounts of saturated FAs USDA–NCAUR. The FA profiles of more than 560 oils, α-C18:3 Viscosity stability coatings Cottonseed Black bean Osage orange purse cold flow properties, and chemical func- mined the fatty acid (FA) profiles of Chemical Characteristics of Oils, Fats, find applications in soaps, cosmetics, and detergents— fats, and waxes can be found in Physical and Chemi- γ-C18:3 Functionality Low iodine Varnishes Linseed Camelina Pinto bean Walnut tionality. Perhaps this is why paints, plant oils extracted from 25 alternative and Waxes, 3rd Edition, edited by David value Plasticizers Safflower Corn DDGs Seashore or why biodiesel, lubricants, and plasticizers are typically cal Characteristics of Oils, Fats, and Waxes, 3rd edition, varnishes, and coatings are prepared feedstocks, then used these profiles to Firestone, AOCS Press, 2013, available Cetane number Soybean Great Northern mallow prepared from vegetable oils containing a high percent- edited by David Firestone, AOCS Press, 2013, available at by chemically modifying vegetable determine the most suitable applica- at http://tinyurl.com/jelvfav. VLCFAs C20:0 Oxidative stability Cardiac health Emollients Ben/Moringa > 25% Arugula Meadowfoam age of monounsaturated FAs. http://tinyurl.com/jelvfav. oils enriched in polyunsaturated FAs, tion(s) for each oil. C22:0 Low iodine value Melting point Emulsifiers Rapeseed (HEAR) Field pennycress Upland cress C22:1 Cetane number Viscosity Cosmetics Indian cress Wild Brazilian

FattyAcid-Infographic-June2016-Inform.indd 2-3 5/23/16 1:42 PM Fatty acid

28 • inform June 2016, Vol. 27 (6) inform June 2016, Vol. 27 (6) • 29 FATTY ACID

Major fatty acid categories and their industrial applications What makes one feedstock suitable whereas those containing high amounts These two summary tables of their Typical Advantages Disadvantages Industrial Traditional Selection Alternative feedstocks examples applications feedstocks criteria for for a particular industrial application, of saturated FAs find applications in results are from a poster, “Fatty acid this study while another is not? Could it be differ- soaps, cosmetics, and detergents—or profile of 25 plant oils and implications SFAs C10:0 Oxidative stability Melting point Soaps Animal fats > 20% Moringa ences in fatty acid (FA) composition? why biodiesel, lubricants, and plasticiz- for industrial applications,” presented at C12:0 Low iodine value Viscosity Detergents Cocoa butter Seashore mallow Saturated FAs have high oxidative ers are typically prepared from vegeta- the 2016 AOCS Annual Meeting & Expo C14:0 Cetane number Functionality Surfactants Coconut C16:0 Palm & palm kernel stability but poor low-temperature ble oils containing a high percentage of in Salt Lake City, Utah, USA, May 1–4, C18:0 Rice bran properties; they also lack a double bond monounsaturated FAs. by Bryan Moser, a research chemist at MUFAs C16:1 Acceptable balance Does not Biodiesel Canola > 40% Ailanthus Cumin Meadowfoam on which to perform chemical modi- To investigate this premise, USDA–NCAUR. Large, printable versions C18:1 of stability, melting excel in any Lubricants Olive Anise Fennel Moringa fication. Polyunsaturated FAs, on the researchers at the US Department of both tables are available at [POST IN point, viscosity and one particular Hydraulic fluids Soybean Arugula Field pennycress Peanut functionality category Sunflower (HO) Coriander Hazelnut Upland cress other hand, exhibit the opposite behav- of Agriculture–National Center for inform|connect; ADD link here]. The Cress Indian cress Wild Brazilian ior, while monounsaturated FAs strike Agricultural Utilization Research (USDA– FA profiles of more than 560 oils, fats, PUFAs C18:2 Melting point Oxidative Paints & Corn > 40% Ailanthus Kidney bean Shepherd’s a balance between oxidative stability, NCAUR) in Peoria, Illinois, USA, deter- and waxes can be found in Physical and α-C18:3 Viscosity stability coatings Cottonseed Black bean Osage orange purse cold flow properties, and chemical func- mined the fatty acid (FA) profiles of Chemical Characteristics of Oils, Fats, γ-C18:3 Functionality Low iodine Varnishes Linseed Camelina Pinto bean Walnut tionality. Perhaps this is why paints, plant oils extracted from 25 alternative and Waxes, 3rd Edition, edited by David value Plasticizers Safflower Corn DDGs Seashore varnishes, and coatings are prepared feedstocks, then used these profiles to Firestone, AOCS Press, 2013, available Cetane number Soybean Great Northern mallow by chemically modifying vegetable determine the most suitable applica- at http://tinyurl.com/jelvfav. VLCFAs C20:0 Oxidative stability Cardiac health Emollients Ben/Moringa > 25% Arugula Meadowfoam oils enriched in polyunsaturated FAs, tion(s) for each oil. C22:0 Low iodine value Melting point Emulsifiers Rapeseed (HEAR) Field pennycress Upland cress C22:1 Cetane number Viscosity Cosmetics Indian cress Wild Brazilian

FattyAcid-Infographic-June2016-Inform.indd 2-3 5/23/16 1:42 PM OLIO 30 • inform June 2016, Vol. 27 (6) New blow to the diet-heart L aura C assiday hypothesis Olio is an Inform column that highlights research, issues, trends, and technologies of interest to the oils and fats community. A recent paper in the British Medical Journal brings to light “lost” data from the Minnesota Coronary Experiment, a large randomized controlled trial conducted from 1968 to 1973 that was designed to test the so-called “diet-heart hypothesis” (Ramsden, C. E., et al., http://dx.doi.org/10.1136/bmj.i1246, 2016). The article strikes a further blow to the already crumbling wall of scientific opinion that dietary saturated fat causes heart disease, and should therefore be avoided.

The BMJ paper, which has been widely covered in the Therefore, researchers led by Christopher Ramsden at media (e.g., http://tinyurl.com/WP-BMJ-study), resurrects the National Institutes of Health (Bethesda, Maryland, USA) unpublished data from the Minnesota Coronary Experiment. recovered raw data and other unpublished documents, includ- This study, conducted by famed nutrition researcher Ancel ing a 1981 master’s thesis, from the Minnesota Coronary Keys, Ivan Frantz, and coworkers, was designed to test Keys’ Experiment. The researchers focused on the 2,355 patients diet-heart hypothesis, which postulated that replacing who were on the study diets for more than one year and had saturated fat in the diet with vegetable oil would lower serum longitudinal measures of serum cholesterol. They recovered cholesterol and thereby reduce coronary heart disease and 149 autopsy files from the 295 autopsies performed. The sur- death. Although based primarily on incomplete epidemiologi- prising results: Although the reduced-saturated-fat diet low- cal data and never confirmed in a randomized controlled trial, ered serum cholesterol compared with the control diet, it was the diet-heart hypothesis is widely accepted as fact and has actually associated with an increased risk of death. In both guided nutritional policy in the United States and elsewhere diet groups, a 30 mg/dL decrease in serum cholesterol was for more than 30 years (Cassiday, L., http://tinyurl.com/ associated with a 22% higher risk of death from any cause. Inform-fat-controversy, 2015). The autopsy results showed that 41% of participants in The study participants were 9,423 men and women aged the intervention group had at least one myocardial infarct, 20–97 years who were institutionalized in either a nursing whereas only 22% of participants in the control group did. home or one of six mental hospitals in the US state of The researchers hypothesize that the increased risk of death Minnesota. Half of the participants were given diets in which in the high-linoleic-acid diet group could have resulted from the usual hospital food was modified to reduce saturated fat increased lipoprotein particle oxidation. intake (from 18.5% to 9.2% of calories) and increase linoleic So why weren’t the original data published? Ramsden and acid intake (from 3.4% to 13.2% of calories). The linoleic acid colleagues suggest several possible reasons: 1) the original came from liquid corn oil, which was used in place of the usual investigators were concerned that certain aspects of the hospital cooking fats or added to various food items. The par- Minnesota Coronary Experiment, such as the complicated ticipants remained on the study diets for a mean period of 384 histories of the study participants, could have biased the days. The researchers collected longitudinal data on serum results, or that the trial did not continue long enough to see cholesterol and cause of death, and a subset of the patients an effect on mortality; 2) statistical software packages for underwent autopsy after death for signs of atherosclero- analyzing the data were not available at the time; 3) the lack sis. In 1989, the researchers published data showing that the of prior published results to “support findings that were so reduced-saturated-fat diet lowered serum cholesterol but contrary to prevailing beliefs and public policy;” and 4) the did not appear to reduce cardiovascular events or death likelihood of rejection of the study results by medical journal (Frantz, I. D., Jr., et al., http://dx.doi.org/10.1161/01. reviewers. ATV.9.1.129). Inexplicably, however, the researchers did not Whatever the reason that these results were buried for include much of the data that were pre-specified by the study, decades, now that they have finally seen the light of day, one for instance, the association between longitudinal changes in can hope that the US Dietary Guidelines Advisory Committee serum cholesterol and the risk of death, or the autopsy results. will consider them when issuing future Guidelines. As one of inform June 2016, Vol. 27 (6) • 31

the largest and most rigorous studies to examine the diet- heart hypothesis, the Minnesota Coronary Experiment adds considerable weight to the growing body of evidence that Olio is produced by Inform’s associate dietary saturated fat does not cause heart disease. Redirect- editor, Laura Cassiday. She can be ing the focus away from saturated fats and toward other cul- contacted at [email protected]. prits, for example, sugar, may help to reverse the trend of rising obesity and chronic disease. However, just as in 1989, there remain firmly entrenched biases against saturated fat that have more to do with belief than science. Information

Cassiday, L. (2015) “Big fat controversy: changing opinions about saturated fat.” Inform, June 2015, 342–349, 377. http://tinyurl. com/Inform-fat-controversy.

Frantz, I. D., Jr., et al. (1989) “Test of effect of lipid lowering by diet on cardiovascular risk. The Minnesota Coronary Survey. Arteriosclerosis 9, 129–135. http://dx.doi.org/10.1161/01.ATV.9.1.129.

Ramsden, C. E., et al. (2016) “Re-evaluation of the traditional diet-heart hypothesis: analysis of recovered data from Minnesota Coronary Experiment (1968–73).” BMJ 353, i1246. http://dx.doi.org/10.1136/bmj.i1246.

Whoriskey, P. (2016) “This study 40 years ago could have reshaped the American diet. But it was never fully published.” The Washington Post, Wonkblog, April 12, 2016. http://tinyurl.com/WP-BMJ-study.

Statistical analysis from Mintec Loraine Hudson

Palm oil prices rose in March and April due to tightening stocks. Although global production in 2015/16 is forecast to remain stable year-on-year at 61.7 million metric tons (MMT), consumption is forecast 6% up year-on-year to 62.1 MMT. As a result, ending stocks are forecast to fall 20% year-on-year to 6.0 MMT, adding upward pressure to palm oil prices. Rapeseed oil prices also rose due to lower expected rapeseed production in 2015/16. The global rapeseed oil production is forecast to fall 3% year- on-year to 27.0 MMT, driven down by a decline in planted area of rapeseed due to lower profitability. Global rapeseed planted area is expected to fall to 33.6m hectares, down 7% year-on-year, driven by falls in Canada (down 3% year-on-year), the EU (-4%) and China (-4%). The forecast has also been reduced due to lower expected crush. In 2015/16, global crush is forecast at 66.6 MMT, down 3% year-on-year. With rapeseed oil consumption forecast at 27.1 MMT, ending stocks are forecast to fall 4% year-on-year to 4.3 MMT. The price differential between palm and rapeseed oil has narrowed considerably since the end of 2015 largely due to concerns over weather- related damage to palm oil output, and resulting in rapeseed oil premium of less than $40 throughout March.

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CorpMbr2016-Spotlight Ad-Jun16i.indd 2 4/21/16 2:28 PM CorpMbr2016-Spotlight Ad-Jun16i.indd 3 4/21/16 2:28 PM Regulatory Review 34 • inform June 2016, Vol. 27 (6)

FSMA final rule on sanitary transportation of human and animal food Regulatory Review is a regular column featuring updates on regulatory matters concerning oils- and fats-related industries.

The US Food and Drug Administration (FDA) has finalized the Food Safety Modernization Act (FSMA) rule on Sanitary Transportation of Human and Animal Food. The rule will help prevent food contamination during motor or rail transportation by requiring shippers, loaders, carriers, and receivers to follow recognized best practices for sanitary transportation, such as properly refriger- ating food and adequately cleaning vehicles between loads. The specific requirements for vehicles and transportation equipment, transportation operations, records, training, and waivers established by the FSMA rule do not apply to transportation by ship or air due to limitations in the law. The earliest compliance dates for some firms begin one year after publication of the final rule in the Federal Register. Here is a summary from the FDA press release (http://tinyurl.com/mkwkrd6).

Who is covered? Key requirements With some exceptions, the final rule applies to shippers, receiv- The rule establishes requirements for: ers, loaders, and carriers who transport food in the United Vehicles and transportation equipment. These requirements States by motor or rail vehicle—whether or not the food is govern the design and maintenance of vehicles and transpor- offered for or enters interstate commerce. The rule also applies tation equipment. For example, such vehicles and equipment to shippers in other countries who ship food to the United must be suitable and adequately cleanable for their intended States directly—by motor or rail vehicle (from Canada or Mex- use and capable of maintaining temperatures necessary for the ico), or by ship or air—and arrange for the transfer of the intact safe transport of food. container onto a motor or rail vehicle for transportation within Transportation operations. These are measures taken during the United States, only if that food will be consumed or distrib- transportation to ensure food safety, such as adequate tem- uted in the United States. perature controls, preventing contamination of ready-to-eat The rule does not apply to exporters who ship food food from touching raw food, protection of food from contam- through the United States (from Canada to Mexico, for ination by non-food items in the same load or previous load, example) by motor or rail vehicle if the food does not enter and protection of food from cross-contact, such as the uninten- US distribution. Companies involved in the transportation of tional incorporation of a food allergen. food intended for export are covered by the rule until the shipment reaches a port or US border. inform June 2016, Vol. 27 (6) • 35

Training. These include the training of carrier personnel in Compliance dates sanitary transportation practices and documentation of the Small businesses. Businesses other than motor carriers who are training. Such training is required when the carrier and ship- not also shippers and/or receivers employing fewer than 500 per- per agree that the carrier is responsible for sanitary conditions sons, and motor carriers having less than $27.5 million in annual during transport. receipts would have to comply two years after the publication of Records. These include maintenance of records of written pro- the final rule. cedures, agreements, and training (required of carriers). The Other businesses. Businesses that are not small and are not other- required retention time for such records depends upon the wise excluded from coverage would have to comply one year after type of record and when the covered activity occurred, but the publication of the final rule. does not exceed 12 months.

Waivers Assistance for industry The FDA FSMA Food Safety Technical Assistance Network The Sanitary Food Transportation Act allows the requirements (http://tinyurl.com/jhakysu) provides information to support of the FSMA rule to be waived if the agency determines that a industry understanding and implementation of FSMA. Questions waiver will not result in the transportation of food under con- submitted online or by mail will be answered by information spe- ditions that would be unsafe for human or animal health. cialists or subject matter experts. The FDA announced in the proposed rule that it intends to The FDA plans to develop an online course that would meet publish waivers for: the training requirements for this rule, and be available before the first compliance dates go into effect. The agency will also issue • Shippers, carriers, and receivers who hold valid permits and guidance to assist industry in complying with the final rule. are inspected under the National Conference on Interstate Milk Shipments (NCIMS) Grade “A” Milk Safety program. This waiver only applies when Grade A milk and milk products— those produced under certain sanitary conditions—are being Exempt from the rule transported. FDA acknowledges that controls for such trans- • Shippers, receivers, or carriers engaged in food transportation operations already exist under the NCIMS pro- portation operations that have less than $500,000 in gram, with state enforcement and FDA oversight. • Food establishments holding valid permits issued by a rel- average annual revenue evant regulatory authority, such as a state or tribal agency, • Transportation activities performed by a farm when engaged as receivers, shippers, and carriers in opera- • Transportation of food that is trans-shipped through the tions in which food is relinquished to customers after being United States to another country transported from the establishment. Examples of such establishments include restaurants, supermarkets, and • Transportation of food that is imported for future export home grocery delivery operations. FDA acknowledges that and that is neither consumed or distributed in the controls for such transportation operations already exist United States under the Retail Food Program, with state, territorial, tribal • Transportation of compressed food gases (e.g. carbon and local enforcement, and FDA oversight. The agency intends to publish these waivers in the Federal dioxide, nitrogen, or oxygen authorized for use in food Register prior to the date firms are required to comply with and beverage products) and food contact substances this rule. • Transportation of human food byproducts transported The FDA also received comments asking for a waiver for for use as animal food without further processing transportation operations for molluscan shellfish for entities that hold valid state permits under the National Shellfish Sani- • Transportation of food that is completely enclosed by tation Program. The agency continues to review comments on a container, except a food that requires temperature this request, and will issue a determination in the near future. control for safety • Transportation of live food animals, except molluscan shellfish 36 • inform June 2016, Vol. 27 (6) patents Supplement composition and method accordance with the present invention, may be non-esterified fatty acids or covalently linked to a lipid, including wax esters, sterol of use esters, triacylglycerols, or any other lipid-related molecular species, Murray, F., O3 Animal Health LLC, US9248155, February 2, 2016 natural or artificial. The branched chain fatty acid can be a C11 to The present invention relates to a dietary supplement composi- C26 branched chain fatty acid and mixtures thereof. tion made of: linolenic expeller pressed soybean oil in the range of 65–85%, Omega 3 (18/12) fish oil 15–35%, and 1–20% alpha- Formulations and dosage forms tocopherol and a method to use this composition to supplement the diet of a domestic animal, such as a canine or an equine. of oxidized phospholipids Sher, N., et al., Vascular Biogenics Ltd., US9254297, February 9, Compositions derived from 2016 The current disclosure provides pharmaceutical composi- metathesized natural oils and tions containing an oxidized phospholipid, such as 1-hexadecyl- amines and methods of making 2-(4′-carboxybutyl)-glycero-3-phosphocholine (VB-201) and a thermosoftening carrier, e.g., a poloxamer. The pharmaceutical Mujkic, M., et al., Dow Corning Corp; Elevance Renewable compositions may further comprise an anti-adherent agent, such Sciences, Inc. US9249360, February 2, 2016 as talc and/or a thixotropic agent. The current disclosure further Wax compositions derived from metathesized natural oils and provides processes for preparing the pharmaceutical compositions. amines and methods of making wax compositions from metathesized The disclosure further provides capsules containing the pharma- natural oils and amines are provided. The wax compositions com- ceutical compositions. Uses of such pharmaceutical compositions prise amidated metathesized natural oils formed from a metathesized and capsules in treating inflammatory disorders are also disclosed. natural oil and at least one amine. The methods comprise providing an amine and providing a metathesized natural oil. The methods further comprise mixing the amine and the metathesized natural oil Supplement composition and method in the presence of a basic catalyst or heat, causing a reaction between of use the amine and metathesized natural oil, therein forming the amidated metathesized natural oil. Fulgham, M., O3 Animal Health LLC, US9254304, February 9, 2016 The present invention relates to a dietary supplement Small liposomes for delivery of immunogen- composition made of: linolenic expeller pressed soybean oil in encoding RNA the range of 65% –85%, Omega 3 (18/12) fish oil 15% –35%, 1% –20% α tocopherol, and 7.5%–15% acai berry powder and Geall, A., and V. Ayush, Novartis Ag, US9254265, February 9, 2016 a method to use this composition to supplement the diet of a Nucleic acid immunization is achieved by delivering RNA domestic animal, such as a canine or an equine. encapsulated within a liposome. The RNA encodes an immunogen of interest, and the liposome has a diameter in the range of 60–180 nm, and ideally in the range 80–160 nm. Thus the invention provides a Compositions and methods for bacterial liposome having a lipid bilayer encapsulating an aqueous core, where- lysis and neutral lipid production in: (i) the lipid bilayer has a diameter in the range of 60–180 nm; and (ii) the aqueous core includes a RNA which encodes an immunogen. Curtiss, Roy, III, and L. Xinyao These liposomes are suitable forin vivo delivery of the RNA to a ver- Arizona Board of Regents for and on Behalf of Arizona State tebrate cell and so they are useful as components in pharmaceutical University, US9255283, February 9, 2016 compositions for immunizing subjects against various diseases. The present invention is directed to a cyanobacterium that produces neutral lipids or alkanes. Such neutral lipids or alkanes Branched-chain fatty acids for prevention may be used for biofuel production. or treatment of gastrointestinal disorders Grease-like gel for repelling rodents Brenna, J.T., and R. Ran-Ressler, Cornell University, US9254275, Richard , N., and W. Ryan, Pacific Tech Ind., Inc, US9258997 February 9, 2016 February 16, 2016 The present invention is directed to a method of preventing or Grease-like compositions are provided for repelling rodents. treating a gastrointestinal condition in a subject, that includes The compositions utilize nontoxic mineral, synthetic, or vegetable administering one or more branched chain fatty acid to the subject oil based gels containing silica, clay, urea, polytetrafluoroethylene, under conditions effective to prevent or treat the gastrointestinal or metallic soap thickeners and capsaicin. condition in the subject. In general, branched chain fatty acids, in

inform June 2016, Vol. 27 (6) • 37

Fat blend vegetable oil and a hydroxyl functional material in the presence of an acid catalyst to form a hydroxyl functional oil polyol, mixing the Krishnadath, B., et al., Loders Croklaan B.V., US9259015, hydroxyl functional oil polyol (with or without epoxidized polybu- February 16, 2016 tadiene) and a functional polyolefin copolymer to form a mixture, A fat blend comprises: (i) a first fat having a solid fat content at reacting the mixture with an ethylenically unsaturated monomer 25 oC of at least 75% and comprising combined SOS and SSO fats component in the presence of an initiator to form a graft copolymer, in an amount of greater than 86% by weight, wherein S is saturated and crosslinking the graft copolymer with a crosslinker to form the fatty acid having from 16 to 18 carbon atoms and O is oleic acid; coating composition, wherein the graft copolymer or the crosslinked and (ii) a second fat having a SOS content of greater than 75% by graft copolymer is inverted into water. weight and a StOSt content of greater than 70% by weight. The fat blend has a solid fat content at 20 oC of greater than 80% and a solid fat content at 35 oC of less than 5%. The fat blend is useful as a cocoa butter replacer. Integrated process for the production of biofuels from different types of starting High-caloric enteral formulations materials and related products De Angelis, N. US9260678, February 16, 2016 Maldonado, Y., et al., Solae LLC, US9259024, February 16, 2016 Process for the production of biocombustible or biofuel mix- Compositions and methods relating to high-caloric enteral tures suitable for different conditions of use, starting from refined or formulations are disclosed herein. The invention provides a dietary raw vegetable oils, including those extracted from seaweed, and/or composition comprising hydrolyzed soy protein and having a low from used food oils and animal fats, each of which is pre-treated with viscosity and acceptable shelf life. Methods of using the dietary specific treatments in order to yield a dried refined oil. The latter compositions of the invention are also disclosed. then undergoes transesterification with an excess of lower alcohols or bioalcohols, and a subsequent separation into a raw glycerine- Water-based coating compositions based phase and a phase containing mixtures of fatty acid alkyl esters and the excess alcohols or bioalcohols. Li, C., et al., Akzo Nobel Coatings Int. B.V., US9260625, February 16, 2016 Coating compositions are disclosed. In some embodiments, the Feed additive composition for ruminants coating compositions are used to coat substrates such as packaging materials and the like for the storage of food and beverages. The and method of producing the same coating compositions can be prepared by reacting an epoxidized Goto, Y., et al., Ajinomoto Co Inc., US9265273, February 23, 2016 A feed additive composition includes a protective agent, lecithin in an amount of 0.05 to 6% by weight relative to a total weight of the composition, a basic amino acid in an amount of at least 40% TD NMR Sample Tubes by weight and less than 65% by weight relative to the total weight of the composition, and water. A method of producing a feed 10, 18, 25(26)mm additive composition includes preparing a molten mixture of at least one protective agent, lecithin and at least one basic amino fl at bottom acid, and solidifying the molten mixture by immersing the molten plain or with fi ll mark mixture in water or an aqueous liquid. The protective agent includes For applications in food science, hydrogenated vegetable oils and/or hydrogenated animal oils having o o the medical, polymer, pharmaceutical melting points of greater than 50 C and less than 90 C. and biodiesel fi elds.

Oxidative Stability Glassware Reaction Vessels, Air Inlet Tubes

Conductivity Vessels Patent information is compiled by Scott Bloomer, a registered US patent agent with Archer Daniels Midland Co., Decatur, Illinois, USA. Contact him at [email protected]. New Era Enterprises, Inc. 1-800821-4667 [email protected] The New Standard in NMR Sampling® www.newera-spectro.com

Quality and value you can rely on! 38 • inform June 2016, Vol. 27 (6) extracts & strength of this association and the amount of dairy needed is not clear. We performed a meta-analysis to quantify the associations of incident T2D with dairy foods at different levels of intake. A systematic literature search of the PubMed, Scopus, and Embase distillates databases (from inception to 14 April 2015) was supplemented by hand searches of reference lists and correspondence with authors of prior studies. Included were prospective cohort studies that examined the association between dairy and incident T2D in healthy Soybean- and coconut-oil-based adults. Data were extracted with the use of a predefined protocol, unsaturated polyester resins: with double data-entry and study quality assessments. Random- thermomechanical characterization effects meta-analyses with summarized dose-response data were performed for total, low-fat, and high-fat dairy, (types of) milk, Costa, C.S.M.F., et al., Ind. Crops Prod. 85: 403–411, 2016, (types of) fermented dairy, cream, ice cream, and sherbet. Non- http://dx.doi.org/10.1016/j.indcrop.2016.01.030. linear associations were investigated, with data modeled with the This paper reports the development of new unsaturated polyes- use of spline knots and visualized via spaghetti plots. The analysis ters resins (UPRs) based on soybean oil and coconut oil. Unsatu- included 22 cohort studies comprised of 579,832 individuals and rated polyesters (UPs) were firstly synthesized by polycondensation 43,118 T2D cases. Total dairy was inversely associated with from renewable monomers and were further crosslinked using T2D risk (RR: 0.97 per 200-g/d increment; 95% CI: 0.95, 1.00; styrene. The chemical structure of the new UPs was confirmed P = 0.04; I2 = 66%), with a suggestive but similar linear inverse as- by attenuated total reflectance Fourier Transform Infrared (ATR- sociation noted for low-fat dairy (RR: 0.96 per 200 g/d; 95% FTIR) and by proton Nuclear Magnetic Resonance (1H NMR) CI: 0.92, 1.00; P = 0.072; I2 = 68%). Nonlinear inverse associations spectroscopies. The thermal and mechanical properties of the UPs were found for yogurt intake (at 80 g/d, RR: 0.86 compared with 0 and UPRs were studied by thermogravimetric analysis (TGA) g/d; 95% CI: 0.83, 0.90; P < 0.001; I2 = 73%) and ice cream intake and by dynamic mechanical thermal analysis (DMTA) to evalu- (at ~10 g/d, RR: 0.81; 95% CI: 0.78, 0.85; P < 0.001; I2 = 86%), but ate the impact of the incorporation of renewable monomers in the no added incremental benefits were found at a higher intake. Other properties of the materials. TGA analysis revealed that bio-based dairy types were not associated with T2D risk. This dose-response UPs are thermally stable until temperatures of 250°C. TheT g values meta-analysis of observational studies suggests a possible role for obtained for these new UPs varied between −11 °C and 2°C, being dairy foods, particularly yogurt, in the prevention of T2D. Results the UP composed by bio-based soybean oil and propylene glycol should be considered in the context of the observed heterogeneity. the resin with the highest Tg . As expected, after crosslinking UPRs showed to be thermally more stable than the UPs. The DMTA High-quality lard with low-cholesterol analysis revealed that the E' and the Tg could be easily tailored by varying the monomers in the formulation. content produced by aqueous enzymatic extraction and β-cyclodextrin treatment Convective drying of papaya seeds Carica( Wang, Q.-L., et al., Eur. J. Lipid Sci.Technol.118: 553–563, 2016, papaya L.) and optimization of oil extraction http://dx.doi.org/10.1002/ejlt.201400662. Chielle, D.P., et al., Ind. Crops Prod. 85: 221–228, 2016, New food processing technology is required for food produc- http://dx.doi.org/10.1016/j.indcrop.2016.03.010. tion with high quality and healthfulness. In this study, a novel The convective air drying of papaya seeds was studied in order application was developed to extract lard from pig fatback, a by- to optimize the seed oil yield. Papaya seeds were dried under dif- product of the slaughter plant, by an aqueous enzymatic extraction ferent conditions of air temperature and air velocity. The operation method (AEE). Various proteases with different properties includ- was characterized by drying rate and drying kinetic curves. Oil was ing Alcalase 2.4 L, Neutrase 1.5 MG, Flavourzyme 1,000 L, and extracted from the seeds, obtained in all drying conditions and, the Protamex were evaluated for their efficiency in oil release and lard yield was optimized. The results revealed that the constant rate and qualities. Alcalase 2.4 L was more effective for oil extraction with falling rate periods occurred during the convective air drying of a yield of 95.19%. A high quality of lard was produced by AEE in papaya seeds. The Overhults kinetic model was suitable to represent comparison with lards produced by conventional extraction meth- the experimental drying curves. The optimal drying conditions, ods in aspects of color, acid value, peroxide value, phospholipids, which provided the maximum seed oil yield, were: air temperature cholesterol, and oxidation stability. A further refinement to reduce of 70 °C and air velocity of 2.0 m s−1. In these conditions, the seed cholesterol from lard by β-cyclodextrin (β-CD) was developed oil yield was 19.23% and the final moisture content was 7.40% and the optimal conditions were established. The optimal condi- (w.b.). High quality oil, with about 90% of oleic acid, was obtained tions were 7% β-CD addition (w/w) to a mixture of equal amount from papaya seeds. of lard and distilled water at reaction temperature 50°C for about 60 min. The cholesterol content of lard from this refinement process was about 3.2 mg/100 g which was about 93.7% reduction from Consumption of dairy foods and diabetes 51.2 mg/100 g. This simple process by AEE and cholesterol reduc- incidence: a dose-response meta- tion did not affect the composition of fatty acids and construction of triglyceride. Factors that were components of lard or produced analysis of observational studies during the lard extraction processes were evaluated for their influ- Gijsbers, L., et al., Am. J. Clin. Nutr. 103: 1111-1124, 2016, ence on the cholesterol removal. Phospholipids could slightly http://dx.doi.org/10.3945/ajcn.115.123216. enhance cholesterol removal, while free fatty acids with saturated or A growing number of cohort studies suggest a potential role unsaturated aliphatic chains would have inhibitory effects because of dairy consumption in type 2 diabetes (T2D) prevention. The of their competition with cholesterol for β-CD. inform June 2016, Vol. 27 (6) • 39

Chemical modifications of ricinolein stability of carotenoids in maize kernels during controlled storage conditions (12 month period), including elevated temperature and in castor oil and methyl ricinoleate relative humidity. There were no significant changes in the content for viscosity reduction to facilitate of individual carotenoids within genotypes during kernel development from 45 days after pollination through the time of harvest. their use as biodiesels Carotenoid losses through traditional grain drying were also mini- Ba, S., et al., Eur. J. Lipid Sci.Technol.118: 651–657, 2016, mal (<9%). However, the stability of carotenoids in maize kernels http://dx.doi.org/10.1002/ejlt.201500120. over storage time after harvest was found to be dependent on both Castor beans contain large quantities of oil and can grow temperature and humidity, with variation observed among geno- in harsh environments. Unlike soybean oil, castor oil cannot be types. Different forms of provitamin A carotenoids follow similar directly used for biodiesel production due to its extremely high degradation rates. The genotype C17xDE3 had a degradation viscosity. Here, we report an alternative source of biodiesel which rate 2 times faster than those of the other genotypes evaluated possesses an ideal viscosity like soybean oil, and this new biodiesel (P < 0.001). These differences in carotenoid stability under con- could be obtained through simple synthetic routes from castor oil. trolled storage were attributed, in part, to observed differences in Moreover, the properties of our newly designed ketone-containing the physical properties of the kernels (surface area and porosity). triglycerides and its transesterified counterpart as biodiesel were These results support the notion that effective control of moisture systematically examined in our study, and their structures were content and temperature of the kernels during storage conditions is characterized by using 1H NMR and 13C NMR. essential to reduce the speed of degradative reactions. Heating two types of enriched margarine: Cross-sectional relationships between complementary analysis of phytosteryl/ dietary fat intake and serum cholesterol phytostanyl fatty acid esters and fatty acids in a Swedish cohort of phytosterol/phytostanol oxidation products 60-year-old men and women Scholz, B., et al., J. Agric. Food Chem. 64: 2699–2708, 2016, Laguzzi, F., et al., J. Hum. Nutr. Diet 29: 325–337, 2016, http://dx.doi.org/10.1021/acs.jafc.6b00617. http://dx.doi.org/10.1111/jhn.12336. Two phytosteryl and/or phytostanyl fatty acid ester-enriched The present study aimed to describe the relationship between margarines were subjected to common heating procedures. UH- self-reported dietary intake and serum cholesterol fatty acids (FAs) PLC-APCI-MS analysis resulted for the first time in comprehensive in a Swedish population of 60-year-old men and women. quantitative data on the decreases of individual phytosteryl/- Cross-sectional data collected in 1997–1998 from 4,232 individu- stanyl fatty acid esters upon heating of enriched foods. These data als residing in Stockholm County were used. Five diet scores were were complemented by determining the concurrently formed created to reflect the intake of saturated fats in general, as well as fats phytosterol/-stanol oxidation products (POPs) via online LC-GC. from dairy, fish, processed meat and vegetable oils and margarines. Microwave-heating led to the least decreases of esters of approxi- Gas chromatography was used to assess 13 FAs in serum cholesterol mately 5% in both margarines. Oven-heating of the margarine in esters. The association between each diet score and specific FAs was a casserole caused the greatest decreases, with 68 and 86% esters assessed by percentile differences (PD) with 95% confidence inter- remaining, respectively; the impact on individual esters was more vals (CI) at the 10th, 25th, 50th, 75th, and 90th percentile of each pronounced with increasing degree of unsaturation of the esterified FA across levels of diet scores using quantile regression. Fish intake fatty acids. In the phytosteryl/-stanyl ester-enriched margarine, was associated with high proportions of eicosapentaenoic acid approximately 20% of the ester losses could be explained by the (EPA) and docosahexaenoic acid (DHA). For each point increase formation of POPs; in the phytostanyl ester-enriched margarine, in fish score, the 50th PD in EPA and DHA was 32.78% (95% CI the POPs accounted for <1% of the observed ester decreases. = 29.22% to 36.35%), and 10.63% (95% CI = 9.52% to 11.74%), respectively. Vegetable fat intake was associated with a high proportion of linoleic acid and total polyunsaturated fatty acids (PUFA) Influence of temperature and humidity on and a low proportion of total saturated fatty acids (SFA). The intake the stability of carotenoids in biofortified of saturated fats in general and dairy fat was slightly associated with specific SFA, although the intake of fat from meat was not. In the maize (Zea mays L.) genotypes during present study population, using a rather simple dietary assessment controlled postharvest storage method, the intake of fish and vegetable fats was clearly associated with serum PUFA, whereas foods rich in saturated fats in general Ortiz, D., et al., J. Agric. Food Chem. 64: 2727–2736, showed a weak relationship with serum SFA. Our results may http://dx.doi.org/10.1021/acs.jafc.5b05698. contribute to increased knowledge about underlying biology in Maize is a staple crop that has been the subject of biofortifica- diet–cardiovascular disease associations. tion efforts to increase the natural content of provitamin A carotenoids. Although significant progress toward increasing provitamin A carotenoid content in maize varieties has been made, postharvest handling factors that influence carotenoid stability during storage have not been fully established. The objectives of this study were to determine carotenoid profiles of six selected provitamin A biofortified maize genotypes at various developmental stages and assess the 40 • inform June 2016, Vol. 27 (6)

Oxidation in EPA- and DHA- Their dynamic role in inflammation and oxidative stress, specifically their interactions with proangiogenic factors in the tumor microen- rich oils: an overview vironment, are well recognized in cancer. Even though the involve- Ismail, A., et al., Eur. J. Lipid Sci. 28: 55–59, 2016, ment of these compounds is one of the key elements in some types http://dx.doi.org/10.1002/lite.201600013. of cancer, knowledge on their role in breast cancer is still limited Oxidation of eicosapentaenoic acid (EPA) and docosahexae- due to the underlying molecular complexity and hormonal control noic acid (DHA) rich omega-3 oils (hereafter referred to as either of breast development and function. This review provides a brief EPA and DHA or omega-3) is a complicated topic, but an impor- overview of some of the current scientific evidence that recognizes tant one to understand. A significant number of consumers cite the role of inflammation and eicosanoids in breast carcinogenesis. fishy burp and/or taste, thought to be the result of oxidation, as one of the main reasons they do not consume EPA and DHA rich oils. Branched chain fatty acids concentrate In addition, consumers note that some articles have raised concerns about the potential for adverse effects associated with consumption prepared from butter oil via urea adduction of oxidized oils. Measuring oxidation in omega-3 oils is complicated Mudgal, S., et al., Eur. J. Lipid Sci.Technol. 118: 669–674, 2016, due to the differences in chemical and physical characteristics of http://dx.doi.org/10.1002/ejlt.201500110. many commercially available products, which means not all meth- Saturated branched chain fatty acids (BCFA) intake in the ods to determine quality are appropriate for all types of oils. A num- US is greater than that of other bioactive fatty acids (FA), yet little ber of consumer advocacy groups, product quality seal programs information is available on methodologies to concentrate them. We and academic groups have published data on levels of oxidation in report here the effect of urea-to-FA (urea:FA) ratio, adduction time, omega-3 oils. Overall, this data shows that commercially available and temperature on the enrichment of branched chain fatty acids omega-3 supplements are low in oxidation. If consumers have a (BCFA) from butter oil. Urea adducts precipitate both saturated poor sensory experience with their omega-3 product, they should and monounsaturated hydrocarbon chains as urea complexes, try another product as an alternative. leaving solubilized polyunsaturated FA and BCFA in the non-urea adduct fraction (NUA). The optimum urea:FA ratio was found to Role of inflammation and be 4:1 and the optimum temperature to be 4°C. Adduction time had negligible effect on BCFA enrichment. Anteiso-15:0 was most eicosanoids in breast cancer enriched across major BCFA under all conditions of temperature, Basu, S., et al., Lipid Technol. 28: 60–64, 2016, time, and urea:FA ratio studied. In our preferred embodiment, a http://dx.doi.org/10.1002/lite.201600017. two-stage urea adduction procedure applied to hydrolyzed butter Mutagenetic and epigenetic influences together with obesity, oil resulted in an enrichment from <2% BCFA in the starting oil nutritional, life-style causes and chronic inflammation are potential to >11% BCFA, indicating an enrichment factor of >6. The best risk-factors for breast cancer. Eicosanoids, namely prostaglandins, method has a first stage performed at 4°C and urea:FA ratio of 4:1, leukotrienes and isoprostanes, are biologically potent compounds and a second stage at 30°C and lower urea:FA ratio (2:1). Overall derived enzymatically or non-enzymatically from arachidonic acid. yield of BCFA in enriched fraction was about 10% of starting BCFA for two stages.

Ionic Liquids in Lipid New Processing and Analysis Opportunities and Challenges Release Edited by Xuebing Xu, Zheng Guo, and Ling-Zhi Cheong List: $175 February 2016 | ISBN 9781630670474 | Available in print and ebook. Member: $123* This title serves as a reference for those interested in state-of-the-art research on the science and technology of ionic liquids (ILs), particularly in relation to lipids *AOCS Members use code AOCS30 processing and analysis. Topics include a review of the chemistry and physics of at checkout for 30% discount and ILs as well as a quantitative understanding of structure-activity relationships at free shipping! the molecular level. Further, chapter authors examine the molecular basis of the toxicity of ILs, the prediction of the properties of ILs, and the rationale and steps Available for purchase at toward a priori design of ionic liquids for task-deﬁ ned applications. store.elsevier.com/aocs Key Features Numerous currencies accepted! ● Reviews the state-of-the-art progress applications of ionic liquids in lipid processing and relevant areas from a variety of perspectives ● Summarizes the latest advances in the measurement of the physical/chemical properties of ionic liquids and available database of thermodynamic properties ● Presents the tremendous opportunity and challenges of ionic liquids as a newly emerging technology for lipids processing area

IonicLiquids-Mar16i-thirdPg.indd 1 1/26/16 2:53 PM inform June 2016, Vol. 27 (6) • 41 Book Review

Trans fats replacement

solutions Dharma R. Kodali (ed.) AOCS Press, 2014, 468 pages Utkarsh Shah ISBN: 9780988856509 http://tinyurl.com/z9shu5z

On June 16, 2015, the US Food and Drug Administration When communicating about trans fats, general audiences (FDA) finalized and published its determination that partially often do not understand that there are different kinds of trans hydrogenated oils (PHO), the primary dietary source of artificial fats, including the artificially processed trans fats that are pro- trans fats in processed foods, are not “generally recognized as duced through partial hydrogenation, the artificially processed safe” (GRAS) for use in human food. The FDA order specifies a trans fats that are used to create CLA supplements, natural compliance date of no later than June 18, 2018. We are already trans fats, and ruminant trans fats. This book nicely touches into June 2016, leaving the industry two years to comply. upon the need for a proper definition of trans fats, and the Substantial efforts have already been made to develop replace- authors successfully define the multiple types of trans fats and ment solutions for industrially produced trans fats. Trans fats their effects on health with clarity. It would have been interest- replacement solutions reviews most aspects of trans fats and ing if the authors had similarly explained the effect these multi- replacement solutions. ple types of trans fats have on the functional properties in food The book discusses several enabling technologies, such applications. The most comprehensive work covered in the as formulation, trait-enhanced oils, palm and coconut oils and book relates to trans fat analysis, which becomes crucial as we their fractions, and interesterified fats, that can be used to move away from industrially produced PHOs completely. The replace trans fats in food products. While manufacturers have importance of quick analytical techniques using Fourier trans- been successful in creating PHO-free products, there is still form-near infrared spectroscopy (FT-NIR) are re-emphasized, a concern that the fats used to replace PHO might increase although validation work for FT-NIR still needs to be done. the amount of saturated fats in these products, as one of the What really impresses me about this book is the breadth of easiest and cheapest ways to replace trans fats while achiev- its content, and its balanced coverage of chemistry, processing, ing solid fat functionality is to replace PHO with saturated fats analysis, and regulation. Initially, the book comes across as a such as palm oil. This could potentially become an issue in the technical book, but then it neatly covers the regulatory details near future. as well. Moreover, it provides a global perspective on the As manufacturers begin looking for innovative techniques replacement efforts and regulations of highest importance to to create trans-free fats with the lowest possible levels of satu- global multi-national companies. The geographical regions dis- rated fats, Trans fats replacement solutions is a good platform cussed include North America, Europe, South America, China, for considering multiple replacement strategies. For exam- Japan, India, Malaysia, Australia, and New Zealand, with a com- ple, the book puts an interesting spin on how to design ideal prehensive chapter dedicated to each one of those regions. designer fats and oleogels that function as trans-free solutions Therefore, this book will be of value to a wide range of read- without adding saturated fats. Per the book, such approaches ers, from experienced scientists and technical leaders to regu- may serve as long-term solutions as opposed to straight latory professionals in all parts of the world. The simplicity of replacement through saturated fats. However, the cost, the language used to explain highly technical terms also makes functionality, and feasibility of implementing such solutions the book appealing for general audiences. All in all, Trans fats on a commercial scale has not been discussed and remains replacement solutions is a valuable book for all trans-free fat/ uncertain. It would have been helpful had the book included oil designers, trans-free product re-formulators, and regulatory more discussions about the limitations of such technologies. professionals. Further discussion about the potential of trans-fat replacement to increase saturated fats in the diet, and the use of oleo- Utkarsh Shah is a senior scientist at The Hershey Company. gels and designer fats in preventing such an increase, would He can be contacted at [email protected]. be meaningful in the coming years and worth a read for future formulators. Welcome New Members

Diane Kelly, Swansea University AOCS is proud to welcome our newest members*. Lisa Kelly, QUALISOY *New and reinstated members joined from January 1 through March 31, 2016. Steven Kelly, Swansea University Alexandra Kendall, University of Manchester Maha Abd. Elrahman, University of Gezira Deborah Chance, University of Missouri Guillermina Gonzalez, RAGASA Salma Khalifa, Savola Food Co Raja-Elie Abdulnour, Brigham And Women’s Lim Chang Hyuk, Aekyung Industry Selene Gonzalez, University of Alberta Abolhassan Khalili, Iranian Vegetable Oil Hospital David Changaris, Ceela Naturals LLC Sai Monaj Gorantla, Indian Institute of Industry Assn Sanjeev Agarwal, Technochem International Dhirajlal Chauhan Chemical Technology Sachin Khapli, New York University Abu Inc Bing-Hung Chen, National Cheng Kung Tsuyoshi Goto, Kyoto University Dhabi Jennifer Altstadt, Sea-Land Chemical Co University Michael Granvogl, Technical University of Dmitriy Khatayevich, Impossible Foods Rivia Amaral, Instituto de Tecnologia de Jingjing Chen, Jiangnan University Munich Kkotsan Kim, Korea University Alimentos ITAL Jingnan Chen, Zhejiang University Liwei Gu, University of Florida Taehoon Kim, Korea University Nuri Andarwulan, Bogor Agricultural Si Chen, Northeast Agricultural University Andrea Guedes, EMBRAPA Michael Kimball University Wai Keat Chen, University of Malaya Alejandro Gugliucci Julie Kindelspire, POET LLC James Anderson, Corbion Peng Cheng, Nankai University Fredrik Gumpel, Novozymes Kohey Kitao, Nitto Pharmaceutical Industries, Jamie Anderson, Sun Products Corp Anis Chikhoune Fatma Gunduz Balpetek, Ege University Ltd. Kathleen Anderson, DSM Nutritional Products Jangwoo Chu, Oh Sung Chemical Ind Co Sahil Gupta, Florida State University Izabela Korwel, HRI Labs Chandra Ankolekar, Kemin Industries Inc Min-Yu Chung, Korea Food Research Institute Nichole Halliday, Rothsay Christoph Krumm, University of Minnesota Rodrigo Araya Rachel Cole, Ohio State University Tianxiang Han, Northeast Agricultural Dmitry Kuklev, W2Fuel LLC Adrian Argudo Fang Cong, Wilmar University Oh-Jea Kwon, Oh Sung Chemical Ind Co Pavel Aronov, Impossible Foods Lanfranco Conte, Universita of Udine Hiroshi Hara, Hokkaido University Jonathan Lai, E2P2L - Solvay China Paul Ashcraft, Flotek Chemistry Zachary Cooper Derell Hardman Ricky Lam, AGT Foods Didem Aykas, Ohio State University Corbion Marc Harrison Nikkia Lassere, Intertek USA Inc Thirupathi Azmeera, Indian Inst of Chemical Marisol Cordova Barragan, UASLP Dustin Hawker, BASF Corp Byung Lee, Korea Res Institute of Chem Tech Technology Jessica Cortopassi, Corto Olive Co Brett Healey, Church & Dwight Co Inc Jeunghee Lee, Daegu University Manochehr Bahmaie, Behshahr Ind Co Prudence Dauphinee, DSM Nutritional Mike Heard, ConAgra Foods Jung-Hoon Lee, Fort Valley State University Vivek Bansal, Brissun Technologies Pvt Ltd Products Kate Hemming, Perdue Agribusiness Ki-Teak Lee, Chungnam National University Amitkumar Barot Chad De Mill, Utah State University Tasha Hermes, Cargill Inc Matt Legg, Phillips 66 James Barren, Kalsec Inc Marvin De Tar, Molecular Technologies Ltd Derek Hess, Utah State University Christophe Len, Universite de Technologie de Chyree Batton, SC Johnson & Son Cedric Deherripon, Vandeputte Shimizu Hidenori, Nitto Pharmaceutical Compiegne Scott Bean, USDA ARS CGAHR Oleochemicals Industries Ltd Bing Li, SC Johnson Eric Bell, Valtris Specialty Chemicals Eduard P.P.A. Derks, DSM Resolve Jessica Hinkle, NOW Foods Jiani Li, Northeast Agricultural University P. Scott Bening, MonoSol LLC Shrinivas Deshmukh, Camlin Fine Sciences Seng Soi Hoong, Malaysian Palm Oil Board Jingbo Li, Aarhus University Jim Benson, Crown Iron Works Inc Ltd Fenghong Huang, Oil Crops Reaearch Juan Li, Omega Protein Inc Amanda Bergamin, CSIRO Food and Nutrition Charlotte Deyrieux, CIRAD UMR IATE Institute, CAAS Qiuhui Li, Northeast Agricultural University Ryan Berko, Cargill Inc Stephen Diegelmann, Afton Chemical Natalia Huerta, Clariant Xu Li, Jiangnan University Matthew Bernart, Pharmatech Inc William Dillavou, Stepan Co Chazley Hulett, Montana State University, Junmei Liang, Wilmar Biotech R&D Ctr Co Ltd Cornelius Bessler, Dalli-Werke GmbH & Co KG Jian Ding, Northeast Agricultural University Northern Wang Liao, University of Alberta Sunil Bhagwat, Institute of Chemical Jixuan Dong, Northeast Agricultural Kosuke Ichihashi, Lion Corp Carli Liguori Technology University Intertek USA Inc Danilo Lima, brprocess Shuang Bi, Northeast Agricultural University Xuyan Dong, Oil Crops Research Institute, Chinami Ishibashi, Hiroshima University Sean Liu, USDA ARS Nirupam Biswas, Monash University CAAS Satoru Ishihara, Amano Enzyme USA Co Ltd Yuanfa Liu, Jiangnan University Malaysia Michael Dreja, Henkel AG & Co KGaA Baraem Pam Ismail, University of Minnesota Haihua Long, Guangzhou Blue Moon Rebecca Blahosky Mannu Dwivedi, MSU Alonso Iturralde, Industrial Danec SA Industrial Co Cory Blanchard, Inventure Renewables Inc Ingolf Ellermann, Crown Iron Works - CMP Ashok Jain, Vibrandt Project Consultants Yao Lu, DSM Nutritional Products Ellen Bloksma Sket (P) Ltd Fernando Luna Cruz, Mone Forwarding Laurine Bogaert, OLEAD Yussef Esparza, University of Alberta Hitesh Jain, Gagan International Henrik Lund, Novozymes AS Christopher Borbone, VICAM Francisco Fabregues, Pinnacle Foods, Inc Anne-Helene Jan, Montpellier SupAgro Xiaolan Luo, Ohio State University Mike Borel, Context Network Aixing Fan, Colgate-Palmolive Zan Jiang, Guangzhou Blue Moon Industrial Wenjun Ma, Northeast Agricultural Swadesh Bose, ITS Testing Services (M) Sdn Hemlata Faujdar, Indira Gandhi National Co University Bhd Open University Mareile Job, Henkel AG & Co KgaA John MacKay, Waters Technologies Corp Ryan Boyd Ben Floan, Crown Iron Works Inc Philip Johnson, University of Nebraska, Monika Madhav, Intertek USA Inc Tatiana Bradaschia, Cargill Agricola SA Garrick Florence, Stratas Foods Lincoln Amborummal Madhavan Jonathan Brekan, Elevance Renewable Ana Forgiarini, Universidad De Los Andes, Richard Johnson, Reckitt Benckiser Samantha Magee, Filtercorp Sciences Lab FIRP David Joiner, Novozymes North America Inc Robert Maloney, Maloney Commodity Diana Budde, Land O’Lakes Inc Masato Fukui, Lion Corp Alexandra Jones, Advanced Fuels Center Services Inc Suzanne Budge, Dalhousie University Noelle Fuller, University of Georgia Andrew Jones, Activated Research Co Emerson Mansano, Coamo Agroindustrial Jiajia Cai, Texas A&M University Ramiro Galleguillos, Lubrizol Jennifer Kaiser, Abbott Nutrition Cooperativa Richard Cairncross, Drexel University Richard Galloway, QUALISOY Karina Kamisato, Alicorp SAA Ebner Manuel, Sun Products Corp Rachel Campbell Mertz, Stratas Foods Kadar Gedi, Sun Products Corp Vikas Kardam, Indian Institute of Technology Hui-Ting Mao, Northeast Agricultural Wenming Cao, Wilmar (Shanghai) Biotech Majd Ghadban Yutaro Kataoka, Nisshin OilliO Group Ltd University R&D Ctr Jaeton Glover, Surface Chemists of Florida Inc Joel Kaufmann, Wenck Associates Inc Dallas Matz, SC Johnson & Son Inc Mark Carkhuff Sachin Goel, University of Toronto Sheshrao Kautkar, GB Pant University of Philip Mausberg, University of Saskatchewan Marcos Cau, YPE--Quimica Amparo Luis Gomez, AAK USA Inc Agriculture & Technology Vera Mazurak, University of Alberta

NewMbrs-Jun16i-2pg.indd 2 4/21/16 2:12 PM All members contribute to the success of the Society while Welcome New Members furthering their professional goals.

Diane Kelly, Swansea University Anthonette McCoy, Nu Skin Pawitchaya Podchong, Silpakorn University Lucas Stolp, University of Minnesota Hideaki Watanabe, Lion Corp AOCS is proud to welcome our newest members*. Lisa Kelly, QUALISOY Dennis McCullough, Process Plus LLC Poornesh Ponnekanti, New York Institute of Chien-Yuan Su Fang Wei, Oil Crops Research Institute *New and reinstated members joined from January 1 through March 31, 2016. Steven Kelly, Swansea University Alex McCurdy, POET LLC Technology Maeva Subileau, Montpellier SupAgro Karl Wei, Procter & Gamble Alexandra Kendall, University of Manchester Terence McGeown, Natures Crops Surya Prakash, MNIT Jaipur Jenna Sullivan Ritter, Nature’s Way Canada Wenck Associates Inc Maha Abd. Elrahman, University of Gezira Deborah Chance, University of Missouri Guillermina Gonzalez, RAGASA Salma Khalifa, Savola Food Co International Palak Pujara, SC Johnson & Son Joanne Sullivan, Pinnacle Foods Sean White, EPL Bio Analytical Services Raja-Elie Abdulnour, Brigham And Women’s Lim Chang Hyuk, Aekyung Industry Selene Gonzalez, University of Alberta Abolhassan Khalili, Iranian Vegetable Oil Aleisha McLachlan, DSM Nutritional Products Andres Puppato, Dallas Group of America Hongbo Sun, Northeast Agricultural Alejandra Wiedeman Hospital David Changaris, Ceela Naturals LLC Sai Monaj Gorantla, Indian Institute of Industry Assn Canada Cecilia Rangel, Instituto Tecnologico University Dylan Wilks, Orange Photonics Inc Sanjeev Agarwal, Technochem International Dhirajlal Chauhan Chemical Technology Sachin Khapli, New York University Abu James McMordie Rupesh Ranjan, UDCT Amravati Shangde Sun, Aarhus University Cody Wilson, Eastman Chemical Inc Bing-Hung Chen, National Cheng Kung Tsuyoshi Goto, Kyoto University Dhabi Sheena McNeill, Intertek Testing Services Shahidah Rashid, University of Malaya, Eric Svenson Tom Wingfi eld, Phillips 66 Jennifer Altstadt, Sea-Land Chemical Co University Michael Granvogl, Technical University of Dmitriy Khatayevich, Impossible Foods Canada Ltd UMCIL Laura Szymczak, Lonza Randall Wood, Procter & Gamble Co Rivia Amaral, Instituto de Tecnologia de Jingjing Chen, Jiangnan University Munich Kkotsan Kim, Korea University Rabiatul Adawiyah Md. Nazeri, University Shivam Rathi Masaki Takaishi, Meiji Co Ltd Victor Hsuehli Wu, Standard Foods Corp, Alimentos ITAL Jingnan Chen, Zhejiang University Liwei Gu, University of Florida Taehoon Kim, Korea University of Malaya Marisa Regitano Darce, Universidade De Sao Igarashi Takako, Kao Corp Taiwan Nuri Andarwulan, Bogor Agricultural Si Chen, Northeast Agricultural University Andrea Guedes, EMBRAPA Michael Kimball Carlos Isaac Medrano Ceja, Aceitera Mevi Paulo ESALQ Michiki Takeuchi, Kyoto University Victoria Wu University Wai Keat Chen, University of Malaya Alejandro Gugliucci Julie Kindelspire, POET LLC Mexico Steven Reider, Lubrizol Keisuke Tanaka, Nikkol Group Cosmos Tech Suo Xiao, University of Akron James Anderson, Corbion Peng Cheng, Nankai University Fredrik Gumpel, Novozymes Kohey Kitao, Nitto Pharmaceutical Industries, Rajesh Meena Eleazer Resurreccion, Montana State Ctr Co Xiaochao Xiong, Washington State University Jamie Anderson, Sun Products Corp Anis Chikhoune Fatma Gunduz Balpetek, Ege University Ltd. Patrick Memoli, Rivertop Renewables University Northern Jenny Tang, DSM Liang Xu, Northeast Agricultural University Kathleen Anderson, DSM Nutritional Products Jangwoo Chu, Oh Sung Chemical Ind Co Sahil Gupta, Florida State University Izabela Korwel, HRI Labs Robert Menzies, Gusmer Enterprises Inc Doug Rivers, ICM Inc Anhad Tayade, IIM Shillong Amar Yadav, Lucknow University Chandra Ankolekar, Kemin Industries Inc Min-Yu Chung, Korea Food Research Institute Nichole Halliday, Rothsay Christoph Krumm, University of Minnesota Francoise Michel Salaun, Diana Pet Food Jim Robertson, Corbion Abbey Thiel, University of Wisconsin, Deepak Yadav, Laxminarayan Institute of Rodrigo Araya Rachel Cole, Ohio State University Tianxiang Han, Northeast Agricultural Dmitry Kuklev, W2Fuel LLC Matthew Miller Cesar Rodriguez, Colgate Palmolive Madison Technology Adrian Argudo Fang Cong, Wilmar University Oh-Jea Kwon, Oh Sung Chemical Ind Co Mudasir Mir, Pondicherry University Brian Rohrback, Infometrix Inc Crista Thomas, Texas Tech University Koichi Yamada, Nitto Pharmaceutical Pavel Aronov, Impossible Foods Lanfranco Conte, Universita of Udine Hiroshi Hara, Hokkaido University Jonathan Lai, E2P2L - Solvay China Ana Miranda Kaitlin Roke, University of Guelph Brian Eckyman Tiensa, University of Guelph Industries Ltd Paul Ashcraft, Flotek Chemistry Zachary Cooper Derell Hardman Ricky Lam, AGT Foods Yoshitaka Miyamae, Lion Corp Alfred Rolle, DSM Nutritional Product Shozo Tomonaga, Kyoto University Zhi-Hong Yang, National Heart, Lung & Didem Aykas, Ohio State University Corbion Marc Harrison Nikkia Lassere, Intertek USA Inc Junki Miyamoto, Hiroshima University Alexandre Romanens, Sani Marc Group Eric Torres, Utah State University Blood Inst Thirupathi Azmeera, Indian Inst of Chemical Marisol Cordova Barragan, UASLP Dustin Hawker, BASF Corp Byung Lee, Korea Res Institute of Chem Tech Ahmed Mohamed Gad, Arma Group Laurence Romsted, Rutgers, The State Elke Trautwein, Unilever R&D Nanthan Yogachandran, Bunge Technology Jessica Cortopassi, Corto Olive Co Brett Healey, Church & Dwight Co Inc Jeunghee Lee, Daegu University Charles Moorefi eld University of New Jersey Tuyen Truong, University of Queensland Sue Young, Crown Iron Works Co Manochehr Bahmaie, Behshahr Ind Co Prudence Dauphinee, DSM Nutritional Mike Heard, ConAgra Foods Jung-Hoon Lee, Fort Valley State University Mubetcel Moorefi eld, Hardy Industrial Siti Rohayu Rubaidi, University of Malaya Apollinaire Tsopmo, Carleton University Wenlin Yu Vivek Bansal, Brissun Technologies Pvt Ltd Products Kate Hemming, Perdue Agribusiness Ki-Teak Lee, Chungnam National University Technologies Mackenzie Russo, Kemin Industries Inc Barry Tulk, DuPont Nutrition & Health Elina Zailer, Spectral Service Amitkumar Barot Chad De Mill, Utah State University Tasha Hermes, Cargill Inc Matt Legg, Phillips 66 Arun Moorthy, University of Guelph Hamid Saadat, Sun Products Corp Ali Ubeyitogullari Qiaozhi Zhang, Northeast Agricultural James Barren, Kalsec Inc Marvin De Tar, Molecular Technologies Ltd Derek Hess, Utah State University Christophe Len, Universite de Technologie de Joseph Moritz, BASF Corp Jobiah Sabelko, Lubrizol Advanced Materials Chinonye Udechukwu University Chyree Batton, SC Johnson & Son Cedric Deherripon, Vandeputte Shimizu Hidenori, Nitto Pharmaceutical Compiegne Kelly Muijlwijk, Wageningen University Katsuyoshi Saitou, Kao Corp Shizuo Ukaji, Nikko Chemicals Co Ltd Ruojie Zhang Scott Bean, USDA ARS CGAHR Oleochemicals Industries Ltd Bing Li, SC Johnson Remco Muntendam, DSM Osama Salih Montes Ulibarri, Sun Products Corp Xiaoyuan Zhang, Northeast Agricultural Eric Bell, Valtris Specialty Chemicals Eduard P.P.A. Derks, DSM Resolve Jessica Hinkle, NOW Foods Jiani Li, Northeast Agricultural University Satoshi Nagaoka, Gifu University Ashwin Sancheti, University of Akron Aman Ullah, University of Alberta University P. Scott Bening, MonoSol LLC Shrinivas Deshmukh, Camlin Fine Sciences Seng Soi Hoong, Malaysian Palm Oil Board Jingbo Li, Aarhus University Sajo Naik, Oil-Dri Corp of America Fazrizatul Shakilla Sani, University of Malaya Aya Umeno, Advanced Industrial Sci & Tech Zipei Zhang Jim Benson, Crown Iron Works Inc Ltd Fenghong Huang, Oil Crops Reaearch Juan Li, Omega Protein Inc Theo Neutzling, Crown Iron Works - CPM Sket Anwesa Sarkar Bijaya Uprety, Lakehead University Mingming Zheng, Oil Crops Research Amanda Bergamin, CSIRO Food and Nutrition Charlotte Deyrieux, CIRAD UMR IATE Institute, CAAS Qiuhui Li, Northeast Agricultural University Kah Soon Ng, PGEO Edible Oils Sdn Bhd Md. 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inform Publications 44 • June 2016, Vol. 27 (6) Membership Application 16INF P.O. Box 17190, Urbana, IL 61803-7190 USA

• Álvarez, C.A. and C.C. Akoh, Preparation of infant formula fat 2016 P: +1 217-693-4813 | F: +1 217-693-4857 | [email protected] | www.aocs.org analog containing capric acid and enriched with DHA and ARA at the sn-2 position Please print or type. • Jana, S. and S. Martini S., Phase behavior of binary blends of four different waxes f Encouraged to join by • Farhoosh, R., A. Sharif, M. Asnaashari, S. Johnny, and N. Molaahmadibahraseman, Temperature-dependent mechanism ❏ Dr. ❏ Mr. ❏ Ms. ❏ Mrs. ❏ Prof. of antioxidant activity of o-Hydroxyl, o-methoxy, and alkyl ester Last Name/Family Name First Name Middle Initial Journal of the American Oil Chemists’ Society derivatives of p-hydroxybenzoic acid in fish oil (April)• • Moreau, R.A., A.F. Harron, M.J. Powell, and J.L. Hoyt, A compari- Firm/Institution son of the levels of oil, carotenoids, and lipolytic enzyme activities Position/Title • Hosseini, H., M. Ghorbani, N. Meshginfar, and A.S. Mahoonak, in modern lines and hybrids of grain sorghum Business Address (Number, Street) A review on frying: procedure, fat, deterioration progress and • Macias-Rodriguez, B. and A.G. Marangoni, Physicochemical and health hazards rheological characterization of roll-in shortenings City, State/Province • Xia, W., S.M. Budge, and M.D. Lumsden, 1H-NMR characterization • Thompson, M.M., et al., Analysis of vitamin K1 in soybean seed: Postal Code, Country Birthdate of epoxides derived from polyunsaturated fatty acids assessing levels in a lineage representing over 35 years of breeding (mm/dd/yyyy) • Montpetit, A. and A.Y. Tremblay, A quantitative method of analysis • Nguyen, Q., et al., Physicochemical properties and ACE-I inhibitory Business Phone Fax Email for sterol glycosides in biodiesel and FAME using GC-FID activity of protein hydrolysates from a non-genetically modified (Expected) Graduation Date (mm/dd/yyyy) • Ok, S., Authentication of commercial extra virgin olive oils soy cultivar • Croat, J.R., M. Berhow, B. Karki, K. Muthukumarappan, and W.R. • Chew, S.-C. and K.-L. Nyam, Oxidative stability of microencapsu- Gibbons, Conversion of canola meal into a high-protein feed lated kenaf seed oil using co-extrusion technology MEMBERSHIP DUES U.S./Non-U.S. Surface Mail Receive Inform via Airmail (Non-U.S.) $ additive via solid-state fungal incubation process ❏ Active ...... ❏ $179 ...... ❏ $269 • He, W.-S., Q. Liu, H. Yu, X.-J. Si, and J.-K. Zhang, Efficient synthesis ❏ Corporate (Bronze) ...... ❏ $875 ...... ❏ $875 ❏ Student* ...... ❏ $ 0 ...... ❏ N/A of octacosanol linoleate catalyzed by ionic liquid and its structure Active membership is “individual” and is not transferable. Membership year is from January 1 through December 31, 2016. characterization *Complimentary student membership includes free access to online Inform only. Stude nt membership applies to full-time graduate students working no • Cheetangdee, N. and S. Benjakul, Oxidation and colloidal more than 50% time in professional work, excluding academic assistantships/fellowships. stability of oil-in-water emulsion as affected by pigmented rice hull OPTIONAL TECHNICAL PUBLICATIONS $ extracts ❏ JAOCS — $185 | ❏ Lipids — $185 | ❏ Journal of Surfactants and Detergents — $185 These prices apply only with membership and include print and online versions and shipping/handling.

DIVISIONS AND SECTIONS DUES (Division memberships are free for students.) $ Divisions Dues/Year Divisions Dues/Year Sections Dues/Year Sections Dues/Year ❏ Agricultural Microscopy $16 ❏ Lipid Oxidation and Quality $10 ❏ Asian $15 ❏ European $25 ❏ Analytical $15 ❏ Phospholipid $20 ❏ Australasian $25 ❏ Indian $10 ❏ Biotechnology $20 ❏ Processing $10 ❏ Canadian $15 ❏ Latin American $15 ❏ Edible Applications Technology $20 ❏ Protein and Co-Products $15 ❏ China FREE ❏ Health and Nutrition $20 ❏ Surfactants and Detergents $30 ❏ Industrial Oil Products $15 MEMBERSHIP PRODUCTS $ ❏ Membership Certifi cate: $25 | ❏ AOCS Lapel Pin: $10 ❏ Membership Certifi cate and AOCS Lapel Pin: $30 Lipids (April) PREFERRED METHOD OF PAYMENT Total Remittance • Hennessy, A.A., P.R. Ross, G.F. Fitzgerald, and C. Stanton, • Rao, Y.P.C., P.P. Kumar, and B.R. Lokesh, Molecular mechanisms ❏ Check or money order is enclosed, payable to AOCS in U.S. funds drawn on a U.S. bank. Sources and bioactive properties of conjugated dietary fatty for the modulation of selected inflammatory markers by dietary ❏ Send bank transfers to: Busey Bank, 100 W. University, Champaign, IL 61820 USA. Account number 11508361. $ acids rice bran oil in rats fed partially hydrogenated vegetable fat Reference: 16INF MEMB. Routing number 071102568. Fax bank transfer details and application to AOCS. • Emery, J.A., F. Norambuena, J. Trushenski, and G.M. Turchini, • Ding, B.-J., et al., The yeast ATF1 acetyltransferase effi ciently ❏ Send an invoice for payment. (Memberships are not active until payment is received.) Uncoupling EPA and DHA in fish nutrition: Dietary demand is acetylates insect pheromone alcohols: implications for the ❏ To pay by credit card, please use our online application (www.aocs.org/join) or contact us at +1 217-693-4813. limited in atlantic salmon and effectively met by DHA alone biological production of moth pheromones • Czajkowska-Mysłek, A., U. Siekierko, and M. Gajewska, • Cavallini, G., et al., A component of the cellular antioxidant Dues are not deductible for charitable contributions for income tax purposes; however, dues may be considered ordinary and necessary business expenses. Application of silver ion high-performance liquid chromatogra- machinery AOCS: Your international forum for fats, oils, proteins, surfactants, and detergents. phy for quantitative analysis of selected n-3 and n-6 PUFA in oil • Brose, S.A., S.A. Golovko, and M.Y. Golovko, Brain 2-arachidon- supplements oylglycerol levels are dramatically and rapidly increased under This Code has been adopted by AOCS to defi ne the rules of professional conduct for its members. • Baack, M.L., S.E. Puumala, S.E. Messier, D.K. Pritchett, and W.S. acute ischemia-injury which is prevented by microwave irradia- AOCS Code of Ethics • Chemistry and its application by scientists, engineers, and technologists have for their prime objective the advancement of science Harris, Daily enteral DHA supplementation alleviates deficiency tion and benefi t of mankind. Accordingly, the Society expects each member: 1) to be familiar with the purpose and objectives of the Society as expressed in in premature infants • Rider T., LeBoeuf R.C., Tso P., Jandacek R.J., The use of kits in the its articles of incorporation; to promote its aim actively; and to strive for self-improvement in said member’s profession; 2) to present conduct that at all • Tan, L., X. Xin, L. Zhai, and L. Shen, Drosophila fed ARA and EPA analysis of tissue lipids requires validation times refl ects dignity upon the profession of chemistry and engineering; 3) to use every honorable means to elevate the standards of the profession and extend its sphere of usefulness; 4) to keep inviolate any confi dence that may be entrusted to said member in such member’s professional capacity; 5) to yields eicosanoids, 15S-Hydroxy-5Z,8Z, 11Z, 13E-eicosatetrae- refuse participation in questionable enterprises and to refuse to engage in any occupation that is contrary to law or the public welfare; 6) to guard against noic acid, and 15S-Hydroxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic unwarranted insinuations that refl ect upon the character or integrity of other chemists and engineers. acid 2016 MbrApp-1p-INF.indd

2016 MbrApp-1p-INF.indd 1 3/28/16 5:30 PM Membership Application 16INF P.O. Box 17190, Urbana, IL 61803-7190 USA 2016 P: +1 217-693-4813 | F: +1 217-693-4857 | [email protected] | www.aocs.org

Please print or type.

f Encouraged to join by

❏ Dr. ❏ Mr. ❏ Ms. ❏ Mrs. ❏ Prof. Last Name/Family Name First Name Middle Initial Firm/Institution Position/Title Business Address (Number, Street) City, State/Province Postal Code, Country Birthdate (mm/dd/yyyy) Business Phone Fax Email (Expected) Graduation Date (mm/dd/yyyy)

MEMBERSHIP DUES U.S./Non-U.S. Surface Mail Receive Inform via Airmail (Non-U.S.) $ ❏ Active ...... ❏ $179 ...... ❏ $269 ❏ Corporate (Bronze) ...... ❏ $875 ...... ❏ $875 ❏ Student* ...... ❏ $ 0 ...... ❏ N/A Active membership is “individual” and is not transferable. Membership year is from January 1 through December 31, 2016. *Complimentary student membership includes free access to online Inform only. Stude nt membership applies to full-time graduate students working no more than 50% time in professional work, excluding academic assistantships/fellowships. OPTIONAL TECHNICAL PUBLICATIONS $ ❏ JAOCS — $185 | ❏ Lipids — $185 | ❏ Journal of Surfactants and Detergents — $185 These prices apply only with membership and include print and online versions and shipping/handling.

PREFERRED METHOD OF PAYMENT Total Remittance ❏ Check or money order is enclosed, payable to AOCS in U.S. funds drawn on a U.S. bank. ❏ Send bank transfers to: Busey Bank, 100 W. University, Champaign, IL 61820 USA. Account number 11508361. $ Reference: 16INF MEMB. Routing number 071102568. Fax bank transfer details and application to AOCS. ❏ Send an invoice for payment. (Memberships are not active until payment is received.) ❏ To pay by credit card, please use our online application (www.aocs.org/join) or contact us at +1 217-693-4813.

Dues are not deductible for charitable contributions for income tax purposes; however, dues may be considered ordinary and necessary business expenses.

AOCS: Your international forum for fats, oils, proteins, surfactants, and detergents.

This Code has been adopted by AOCS to defi ne the rules of professional conduct for its members. AOCS Code of Ethics • Chemistry and its application by scientists, engineers, and technologists have for their prime objective the advancement of science and benefi t of mankind. Accordingly, the Society expects each member: 1) to be familiar with the purpose and objectives of the Society as expressed in its articles of incorporation; to promote its aim actively; and to strive for self-improvement in said member’s profession; 2) to present conduct that at all times refl ects dignity upon the profession of chemistry and engineering; 3) to use every honorable means to elevate the standards of the profession and extend its sphere of usefulness; 4) to keep inviolate any confi dence that may be entrusted to said member in such member’s professional capacity; 5) to refuse participation in questionable enterprises and to refuse to engage in any occupation that is contrary to law or the public welfare; 6) to guard against unwarranted insinuations that refl ect upon the character or integrity of other chemists and engineers.

2016 MbrApp-1p-INF.indd

2016 MbrApp-1p-INF.indd 1 3/28/16 5:30 PM Latin America Update 46 • inform June 2016, Vol. 27 (6)

Olive oil production in South America: Uruguayan extra-virgin olive oil

Latin America Update is a regular Inform column that features information about fats, oils, and related materials in that region.

Leslie Kleiner

When thinking about olives and olive oil, it is common to picture scenes from the Mediterranean. However, various Latin American countries are olive oil producers as well. To learn more about olive oil production in Uruguay, I interviewed Professor Bruno Irigiaray, from the Fats and Oils Laboratory at the Chemistry Department School of the Universidad de la República, Uruguay. inform June 2016, Vol. 27 (6) • 47

that of the polyphenols present in the oil. Many times, it is dif- Q: Which MERCOSUR member countries ficult to compare polyphenol levels among samples of different produce olive oil, and what is their annual origins due to differences in the methodology used. However, production? recent studies performed in Spain report polyphenol levels on two- or three-phase extraction olive oil ranging between 50 and 800 ppm. Uruguayan olive oil has polyphenol levels among A: Argentina, Brazil, Chile, Peru, Mexico, and Uruguay the reported ranges but below 400 ppm. are some of the main olive-oil- producing countries in Latin America. There is also smaller-scale production in Bolivia, Colombia, and Ecuador. The producing countries that are How would you describe the flavor members of MERCOSUR are Argentina, Bolivia, Brazil, and Q: Uruguay. However, only Argentina, Chile, and Uruguay profile of Uruguayan olive oil? are members of the Consejo Oleícola Internacional (IOC: International Olive Council). According to information The flavor profile of Uruguayan olive oil depends, as provided by IOC, the 2014–2015 olive oil production in A: in olive oil from any country of origin, on the olive cultivar, its Uruguay, Argentina, and Chile, was 1,500, 6,000, and 24,000 quality, and other factors such as climate and irrigation. Olive metric tons (MT), respectively. oil arising from the Arbequina variety tends to be sweet, less bitter and spicy, and with molasses notes, while other varieties such as Coratina and Picual have intensely bitter and spicy Q: What are common methods of olive oil notes. Uruguay has an IOC-recognized olive oil tasting panel production in Uruguay? which has been active since the year 2012.

A: Only extra-virgin olive oil is produced in Uruguay. There is no refining of oils of lesser quality, due to the lack of indus- Q: What are the waxes from Uruguayan trial plants for that purpose. Furthermore, Uruguay aims to olive like? produce high-quality oils, and in consequence the priority is to produce extra-virgin olive oil in compliance with analytical testing as established by the methodology specified by IOC. A: The waxes profile is influenced by olive variety, storage, and climatic conditions. In general, in Uruguayan extra virgin olive oils the waxes are mostly comprised of 40 and 42 carbons, and waxes of 44 and 46 carbons are not usually Q: How is olive oil characterized, and how detected. do Uruguayan oils differ from those produced in Mediterranean regions? Latin America Update is produced by Leslie Kleiner, R&D Project A: The fatty acid profile is an important parameter when Coordinator in Confectionery analyzing olive oil, and this profile is expected to fall within the Applications at Roquette Americas, Inc., parameters established by IOC. Another important factor is Geneva, Illinois, USA, and a contributing editor of Inform. She can be reached at [email protected]. 48 • inform June 2016, Vol. 27 (6)

AOCS Meeting Watch October 4–7, 2016. World Conference on Fabric and September 11–14, 2017. 17th AOCS Latin American Home Care—Singapore 2016, Shangri-La Hotel, Singapore. Congress and Exhibition on Fats and Oils, Grand Fiesta http://singapore.aocs.org Americana Coral Beach Hotel, Cancun, Mexico.

April 30–May 3, 2017. AOCS Annual Meeting and Industry For in-depth details on these and other upcoming meet- Showcases, Rosen Shingle Creek, Orlando, Florida, USA. ings, visit http://aocs.org/meetings or contact the AOCS Meetings Department (email: [email protected]; phone: +1 217-693-4821; fax: +1 217-693-4865).

A doctoral student in food science wanted to know if biodiesel producers would be willing to pay a premium for Tips from distillers corn oil with a lower free fatty acid (FFA) content. Tips from inform|connect is a regular Inform column that features tips and other discussion highlights from the community forum board at http://www.informconnect.org/home.

Q: An article in the March 2016 issue of Inform reveals that installation in India with huge capital expenditures failed process contaminants are created when edible fats and measurably. Molecular distillation (short-path distilla- Q:oils are exposed to high temperatures and long residence tion) was very selective in removing the fatty acids and times during traditional deodorization. It seems to me that a other lipid moieties rapidly, based on molecular weight molecular still could prevent, or at least minimize, formation as well as absolute pressure in the system, but in doing of harmful compounds, as the exposure to high tempera- so all the broken down color bodies were left behind in tures is extremely short (a few seconds), compared to hours the deodorized/de-acidified oil. The distilled fatty acids of exposure during traditional deodorization. Why aren’t produced were almost water- white, but the oil itself wiped-film evaporators, short-path distillers, or molecular was dark-colored and could not be reduced by solution, stills commonly used for deodorizing edible fats and oils? as it was a totally "fixed color." It is true that formation of 3-MCPD esters is an issue, but the retention time A: Here is a summary of the responses. required is not for the heat-bleaching alone. Some oils • Wiped-film evaporators or molecular stills are an order and specialty fats, such as cocoa butter and sal oil, con- of magnitude more expensive than the deodorizers used tain pesticides that can be removed only with a longer A: retention at relatively low deodorization temperatures. today. In Southeast Asia, typical capacity requirements are between 1,500–3,000 tons per day of oil per deodor- • Molecular distillation is a fantastic simple unit operation izer. Multiple wiped-film evaporators or molecular stills for heat-sensitive materials like tocopherols and omega-3 would be needed to reach these capacity requirements, fatty acids. It is also good for smaller-capacity biodiesel distil- which would drive up capital expenditures. With palm lation, as one can convert non-edible high-FFA oils into low oil, more time under high temperature is needed to FFA oils by simple one step molecular distillation. break down the color and enable the oil to become vola- • Wiped-film/short-path distillation can help recover tile enough to be stripped. Typically, one hour of resi- some of the valuable nutraceuticals, such as tocopher- dence time under high temperature is required to meet ols, tocotrienols, sesamin, and sterols that are lost during the market demand for oil that is low in (red) color. This refining. Wiped-film/short-path distillation has also con- long residence time is practical in a tray deodorizer, but tributed a lot to the recovery of eicosapentaenoic acid not in a wiped-film evaporator. When the temperature (EPA)/docosahexaenoic acid (DHA) from fish oils, produc- and pressure conditions required to evaporate some of tion of carotene-rich red palm oil, lecithin recovery, and the contaminants are reached, the monoglycerides and the distillation of fatty acids, methyl esters, and glycer- diglycerides are then distilled away. This moves a sig- ine. Capital expenses and color reduction are big issues nificant portion of the yield from high- value palm oil to when processing some high FFA oils by molecular distilla- lower-value palm fatty acid distillate, which has a signifi- tion, but niche oils such as sesame, rice bran, and corn— cantly negative impact on refining margins. which have a high percentage of unsaponifiables and can • Molecular distillation was thought to be the best solution be of huge therapeutic value—can certainly be processed for stripping/physical refining of high-free-fatty-acid (FFA) by wiped film if we are willing relinquish the bias for low rice bran oil (FFA as high as 30%). However, one such color that has gripped the entire industry for many years. Crown Refining We do refining. And we do it well.

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