DOCSLIB.ORG

United States Patent (19) 11) 4,298,730 Galleymore Et Al

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
United States Patent (19) 11) 4,298,730 Galleymore Et Al United States Patent (19) 11) 4,298,730 Galleymore et al. 45 Nov. 3, 1981 54 PROCESS FOR THE PRODUCTION OF A 3,867,301 2/1975 Watanabe............................ 252/132 SURFACTANT CONTAINING SUCROSE 3,963,699 6/1976 Rizzi............. ... 534/119 ESTERS 3,996,206 12/1976 Parker. 536/119 4,032,702 6/1977 James .................................. 536/119 75 Inventors: Harry R. Galleymore, Bath; Kenneth James, Reading; Haydn F. Jones, FOREIGN PATENT DOCUMENTS Reading; Chaman L. Bhardwaj, 1399053 6/1975 United Kingdom................ 536/119 Reading, all of England; James S. Plant, deceased, late of Reading, Primary Examiner-Dennis L. Albrecht England; by Aline P. Plant, Attorney, Agent, or Firm-Ostrolenk, Faber, Gerb & administrator, Manchester, England Soffen 73) Assignee: Tahres Development (N.A.) N.V., (57) ABSTRACT Curacao, Netherlands Antilles The process for the preparation of a surfactant mixture containing sucrose mono- and di-esters, by reacting a 21) Appl. No.: 174,277 starting mixture including solid particulate sucrose, at 22 Filed: Jul. 31, 1980 least one triglyceride of a fatty acid having at least 8 30 Foreign Application Priority Data carbon atoms and a basic transesterification catalyst, at a temperature of from 110 to 140° C. at atmospheric Dec. 19, 1979 (GB) United Kingdom ..... ... 43762/79 pressure and in the absence of any solvent, is improved May 1, 1980 GB United Kingdom ............... 14370/80 by using a starting mixture which: 51) Int. Cl. ....................... C07H 13/06; C11D 1/66; (a) contains a di and/or mono-glyceride in an amount C11D 9/26; C11D 11/04 to provide a hydroxyl value of greater than 500 mg 52) U.S. Cl. ................................... 536/119; 252/89.1; KOHM 100g of starting mixture; 252/132; 252/174.17; 260/410.6 (b) contains at least 10% by weight of a fatty acid 58) Field of Search .................. 252/89.1, 132, 174.21, soap in addition to the basic transesterification 252/174.17; 260/410.6; 536/119 catalyst, at least 50% by weight of the soap being (56) References Cited potassium soap, and (c) (when the soap content is less than 20% by U.S. PATENT DOCUMENTS weight) contains at least 25% by weight of sucrose. 2,970,962 2/1961 Hass .................................... 252/135 The improved process gives good yields in much 3,251,827 5/1966 Schnell .... ..., 536/119 3,480,616 11/1969 Osipow ........... ... 536/119 shorter reaction times and the products have high HLB 3,558,597 1/1971 Von Brachel ... 536/119 values. 3,714,144 1/1973 Feuge .......... ... 536/119 3,792,041 2/1974 Yamagishi........................... 536/119 20 Claims, 10 Drawing Figures 6 5 ki g 3 o 92 s 2 1 0. -- --- T O O 2O 30 40 INTIAL SOAP CONCENTRATION (%) U.S. Patent Nov. 3, 1981 Sheet 1 of 10 4,298,730 Z W 0% 08 U.S. Patent Nov. 3, 1981 Sheet 2 of 10 4,298,730 O 2O 30 40 INITIAL SOAP CONCENTRATION (%) FIG2. U.S. Patent Nov. 3, 1981 Sheet 3 of 10 4,298,730 G#9 Z U.S. Patent Nov. 3, 1981 Sheet 4 of 10 4,298,730 1OO 90 80 70 60 50 LO 3 O 20 10 O "/K SOAP O 10 20 30 O 50 60 70 BO 90 100 1. No SOAP FG4. U.S. Patent Nov. 3, 1981 Sheet 5 of 10 4,298,730 8o ass 2 o Co CO S 32gt N O Ul 2 up d d S 4. so O l 2. mh r N vm O O co o op o O d C O O na n m (/) 30+W U.S. Patent Nov. 3, 1981 Sheet 6 of 10 4,298,730 0009,0099000G00G70007OOGE000£OOGZ000Z00G| '99]+(500l/HOMÂu),TVMINXOHOMHTWIN 000|| 009 0 U.S. Patent Nov. 3, 1981 Sheet 7 of 10 4,298,730 inha CM cy al O s O ap m LL Ns e Sa N Ean O O unwill SSRSS O L Lao to On U?o O ad Le d u r N N m O op e O o s LA) o n CN s Se LA) U.S. Patent Nov. 3, 1981 Sheet 8 of 10 4,298,730 MEDE (GRAPHICAL ESTIMATION) 25 DG N S 20 N / Yv -ME N (%) N A. w w Y. M 15 N/ y / N / MG \ 1. - 7 YSN 10 / --N - 74- - - -DE 21 M A / 2 M 5 / / / / / / / -1 TG of INITIAL SUCROSE CONCENTRATION FIG.8. U.S. Patent Nov. 3, 1981 Sheet 9 of 10 4,298,730 l O 3 5 3 O 10 15 2O 25 30 35 40 PERCENTAGE SUGAR BY WEIGHT USED IN REACTIONS FIG.9. U.S. Patent Nov. 3, 1981 Sheet 10 of 10 4,298,730 O 10 15 20. 25 30, 35 40 PERCENTAGE SUGAR BY WEIGHT USED IN REACTIONS FIG.O. 4,298,730 1. 2 U.S. Pat. No. 3,480,616 (of Osipow et al) describes a PROCESS FOR THE PRODUCTION OF A modified form of the solvent transesterification process SURFACTANT CONTAINING SUCROSE ESTERS in which sucrose is reacted with a methyl ester, such as methyl tallowate, in a solvent such as propylene glycol This invention relates to the production of a surface 5 which dissolves the sucrose but not the fatty compo active material comprising or consisting of one or more nent. An emulsifying agent is used, and the reaction is fatty acid esters of sucrose. performed in a so-called “micro-emulsion'. Although Esters of sucrose with fatty acids, particularly the this process avoids the disadvantages arising from the sucrose mono-esters and di-esters, are potentially very use of a toxic solvent such as dimethylformamide, it still valuable as surfactants and have a number of unique 10 has to be performed under reduced pressure and in the advantages in this role. Thus, they are non-toxic, odour absence of any water. less and tasteless; they are non-irritating to the skin; and, A later modification of the solvent transesterification when ingested, they hydrolyse to form normal food process, described in British Pat. No. 1,332, 190 (of Dai products. Unlike most surfactants, they are biodegrad Ichi Kogyo Seiyaku Co. Ltd.) uses water as the solvent. able under both aerobic and anaerobic conditions; and, 15 The sucrose is completely dissolved in water in the unlike most other non-ionic surfactants, they are solid presence of a fatty acid soap, a fatty acid ester and a and thus readily usable in powdered or spray-dried transesterification catalyst are added, and the mixture is products. They are very good emulsifiers; and they dehydrated under reduced pressure and at elevated perform well as detergents, either alone or in combina temperature so as to produce a homogeneous melt. The tion with anionic surfactants, and can be formulated 20 melt is then maintained at elevated temperature, for the either as high-foaming or low-foaming detergents. Ac transesterification reaction to take place. Although this cordingly, they can be used generally as domestic or process avoids the problems which arise when using an industrial detergents, and also in specialised uses such as organic solvent such as dimethylformamide or propy additives for foodstuffs, animal feeds, cosmetics, phar lene glycol, it is a multistage process which still requires maceuticals and agricultural chemicals. 25 heating under reduced pressure, and the pressure must However, in spite of possessing these advantages, be carefully controlled in relation to the temperature sucrose ester surfactants have never been exploited to when producing the dehydrated melt, in order to avoid their full potential, because of difficulties arising in their hydrolysis of the fatty acid ester. The process is, there production. Many processes have been proposed for the fore, undesirably complicated for use on an industrial preparation of sucrose ester surfactants but, due to tech 30 scale. nical and economical disadvantages, it is still not easy to A solvent-free transesterification process has also achieve large-scale industrial production at a price com been proposed in J. Amer. Oil Chem. Soc. 1970, 47, (2), petitive with other surfactants. 56-60; and U.S. Pat. No. 3,714,144 (of Feuge et al). In Sucrose esters cannot efficiently be prepared by the accordance with this process, it is stated that the sol direct esterification of sucrose with a fatty acid, but 35 vent-free transesterification must be carried out with three other methods are possible: reaction with a fatty the sucrose in the molten state; and the process is, there acid chloride; reaction with a fatty acid anhydride; and fore, performed at a temperature of from 170 to 190° C. transesterification with a fatty acid ester. The reaction After a short time, the molten sucrose begins to degrade with acid chlorides, which is performed in the presence to a black tarry mass, and the reaction with the fatty of pyridine, is uneconomical and will not give good 40 acid ester must necessarily be performed very quickly: yields of sucrose monoesters or diesters: it can be used the reaction is generally stopped within 20 minutes, and to prepare sucrose octa-esters, but these are unsatisfac sometimes after only 2 minutes. As in the solvent pro tory as surfactants. Acid anhydrides of the higher fatty cesses, the reaction is performed under reduced pres acids are not available commercially, and their prepara sure, to distill off the alcoholic by-product. Further tion is complicated and expensive. Consequently, at 45 more, the reaction must be performed in the presence of tempts at finding a commercial process for the prepara an alkali-free anhydrous soap, which serves to solubilise tion of sucrose ester surfactants have concentrated on the fatty acid ester in the molten sucrose and to catalyse the transesterification reaction, generally using methyl the transesterification: alkoxides, free alkalis and ordi or glyceryl esters of fatty acids.
Load more

Recommended publications
  • Sucrose Octanoate Esters Crop 1 2 Identification of Petitioned Substance
    Sucrose Octanoate Esters Crop 1 2 Identification of Petitioned Substance 3 Chemical Names: CAS Numbers: 4 sucrose octanoate esters 15 CAS NO. 42922-74-7 (monooctanoate), 58064-47-4 5 16 (dioctanoate) 6 Other Name: 7 (∀-D-glucopyranosyl-∃-D-fructofuranosyl- Other Codes: 8 octanoate), mono-, di-, and triesters of sucrose 17 OPP Chemical Code: 035300 9 octanoate 10 11 Trade Names: 12 Avachem Sucrose Octanoate Manufacturing Use 13 Product 14 Avachem Sucrose Octanoate [40%] 18 19 Characterization of Petitioned Substance 20 21 Composition of the Substance: 22 23 Sucrose octanoate esters (SOEs) belong to the organic chemical family sucrose fatty acid esters (SFAEs).1 24 SFAEs are surfactants (or surface active agents) that lower the surface tension of a liquid, allowing easier 25 spreading and evaporation. Surfactants are usually organic compounds that contain both hydrophobic 26 (fat-soluble) and hydrophilic (water-soluble) groups (Wikipedia, n. d.). SFAEs have sucrose residues as the 27 hydrophilic group and fatty acid residues as the lipophilic group. SOEs are manufactured from sucrose 28 (table sugar) and an octanoic acid ester commonly found in plants and animals. Sucrose esters, as a class of 29 related compounds, vary depending on the number and locations of esters attached to the sucrose 30 molecules. Sucrose has eight potential places where individual esters may attach (Montello Inc., n. d.). The 31 substance under review is a mixture of mono-, di-, and triesters. 32 33 Sucrose esters were first isolated when researchers investigated the insecticidal properties of the tobacco 34 leaf hairs. This insecticidal property of sucrose esters acts by dissolving the waxy protective coating 35 (cuticle) of target pests, causing them to dry out and die (U.S.
    [Show full text]
  • Sucrose Esters in Gel-To-Milk Emulsion Concepts
    For know-how in sucrose ester techniques Sucrose esters in gel-to-milk emulsion concepts EXPERIENCE OUR EXPERTISE! Introduction Sisterna B.V.is a young and flexible organisation that is solely active in the promotion and sales of Sisterna® sucrose esters. Furthermore Sisterna has developed countless proven and innovative applications of these natural and multifunctional emulsifiers for the cosmetic industry. Sisterna® sucrose esters are based on sucrose and vegetable fatty acids and are a unique range of high quality, non-ionic emulsifiers with an exceptional performance and mildness to skin and eyes. Besides emulsification Sisterna® sucrose esters can offer other unique benefits to personal care formulations. Sisterna has developed various interesting emulsion concepts, such as a gel-to-milk concept, the subject of this paper. Sisterna’s exclusive distributor network ensures the availability and technological knowhow of sucrose esters in personal care applications in the Western Hemisphere. 2 Summary Sisterna® sucrose esters with a high HLB are very suitable emulsifiers for the development of natural 'oil gels' that turn into milk when diluted upon use. These 'oil gels' are in fact concentrated oil-in-glycerin (O/G) emulsions that can be produced by using standard high shear homogenising equipment. Very narrow oil droplet size emulsions with average oil droplet sizes of 300 - 500 micron are obtained. By using just 2% of one single high HLB sucrose ester, preferably sucrose palmitate, it is already possible to produce a gel-to-milk concept containing 60% of oil. Such a concept is very suitable for make-up cleansing. The high oil content will allow to remove all impurities.
    [Show full text]
  • Effects of Selected Polysorbate and Sucrose Ester Emulsifiers on the Physicochemical Properties of Astaxanthin Nanodispersions
    Molecules 2013, 18, 768-777; doi:10.3390/molecules18010768 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.com/journal/molecules Article Effects of Selected Polysorbate and Sucrose Ester Emulsifiers on the Physicochemical Properties of Astaxanthin Nanodispersions Navideh Anarjan 1,2 and Chin Ping Tan 1,* 1 Department of Food Technology, Faculty of Food Science and Technology, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia; E-Mail: [email protected] 2 Young Researchers and Elites Club, East Azarbaijan Science and Research Branch, Islamic Azad University, 15655/461, Tabriz, Iran * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +603-8946-8418; Fax: +603-8942-3552. Received: 7 December 2012; in revised form: 28 December2012 / Accepted: 31 December 2012 / Published: 9 January 2013 Abstract: The effects of selected nonionic emulsifiers on the physicochemical characteristics of astaxanthin nanodispersions produced by an emulsification/evaporation technique were studied. The emulsifiers used were polysorbates (Polysorbate 20, Polysorbate 40, Polysorbate 60 and Polysorbate 80) and sucrose esters of fatty acids (sucrose laurate, palmitate, stearate and oleate). The mean particle diameters of the nanodispersions ranged from 70 nm to 150 nm, depending on the emulsifier used. In the prepared nanodispersions, the astaxanthin particle diameter decreased with increasing emulsifier hydrophilicity and decreasing carbon number of the fatty acid in the emulsifier structure. Astaxanthin nanodispersions with the smallest particle diameters were produced with Polysorbate 20 and sucrose laurate among the polysorbates and the sucrose esters, respectively. We also found that the Polysorbate 80- and sucrose oleate-stabilized nanodispersions had the highest astaxanthin losses (i.e., the lowest astaxanthin contents in the final products) among the nanodispersions.
    [Show full text]
  • Process for the Production of a Surfactant Containing Sucrose Esters
    Patentamt JEuropaischesEuropean Patent Office © Publication number: 0 031 191 Office europeen des brevets A1 © EUROPEAN PATENT APPLICATION © Application number: 80302785.3 © Int. CI.3: C 07 H 15/06 © Date of filing: 13.08.80 © Priority: 19.12.79 GB 7943762 © Inventor: Galleymore, Harry Reginald 01.05.80 GB 8014370 69 High Street Bathford Bath BA1 7SZAvon(GB) © Date of publication of application: (72) Inventor: James, Kenneth 01.07.81 Bulletin 81/26 34, Crawford Close Earley Reading Berkshire(GB) © Designated Contracting States: AT BE CH DE FR IT LI LU NL SE ©) Inventor: Jones, Haydn Frederick 27, Malone Road Woodley © Applicant: TATE & LYLE PATENT HOLDINGS LIMITED Reading Berkshire(GB) 5th Floor, Triningham Building Front Street Hamilton 5(BM) © Inventor: Bhardwaj, Chaman Lai 31 Crescent Road Tilehurst © Applicant: TALRES DEVELOPMENT (N.A.) N.V. Reading Berkshire RG3 5AH(GB) Breedestraat 39C Curacao, Netherlands Antiiles(NL) (72) Inventor: Plant, James Stephen Deceased © Designated Contracting States: G(GB) BE © Representative: Ablewhite, Alan James et al, MARKS & CLERK 57/60 Lincoln's Inn Fields London WC2A3LS(GB) © Process for the production of a surfactant containing sucrose esters. The process for the preparation of a surfactant mixture containing sucrose mono-and di-esters, by reacting a starting mixture including solid particulate sucrose, at least one trig- lyceride of a fatty acid having at least 8 carbon atoms and a basictransesterification catalyst, atatemperature offrom 110 to 140°C at atmospheric pressure and in the absence of any solvent, is improved by using a starting mixture which:- (a) contains a di and/or mono-glyceride in an amount to provide a hydroxyl value of greater than 500 mg KOH/100g of starting mixture; (b) contains at least 10% by weight of a fatty acid soap in addition to the basic transesterification catalyst, at least 50% by weight of the soap being potassium soap, and (c) (when the soap content is less than 20% by weight) contains at least 25% by weight of sucrose.
    [Show full text]
  • Nanoemulsion Including Sucrose Fatty Acid Ester Nanoemulsionen Enthaltend Saccharosefettsäureester Nanoemulsions Comprenant Des Ester D’Acide Gras De Sucrose
    (19) TZZ ¥__T (11) EP 2 563 164 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A23L 29/10 (2016.01) A23L 33/10 (2016.01) 29.06.2016 Bulletin 2016/26 A23L 33/15 (2016.01) A61K 9/107 (2006.01) (21) Application number: 11713391.8 (86) International application number: PCT/US2011/000538 (22) Date of filing: 22.03.2011 (87) International publication number: WO 2011/119228 (29.09.2011 Gazette 2011/39) (54) NANOEMULSION INCLUDING SUCROSE FATTY ACID ESTER NANOEMULSIONEN ENTHALTEND SACCHAROSEFETTSÄUREESTER NANOEMULSIONS COMPRENANT DES ESTER D’ACIDE GRAS DE SUCROSE (84) Designated Contracting States: (72) Inventor: BROMLEY, Philip, J. AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Fullerton, CA 92832 (US) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR (74) Representative: Boult Wade Tennant Designated Extension States: Verulam Gardens BA ME 70 Gray’s Inn Road London WC1X 8BT (GB) (30) Priority: 23.03.2010 US 340944 P (56) References cited: (43) Date of publication of application: WO-A1-2008/039564 WO-A1-2009/029046 06.03.2013 Bulletin 2013/10 WO-A1-2010/008762 DE-A1-102008 015 366 US-A1- 2009 297 665 (73) Proprietor: VIRUN, INC. Walnut, CA 91789 (US) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations.
    [Show full text]
  • Preparation of Sucrose Fatty Acid Esters As Food Emulsifiers and Evaluation of Their Surface Active and Emulsification Properties
    280 Grasas y Aceites Vol. 50. Fase. 4 (1999), 280-282 Preparation of sucrose fatty acid esters as food emulsifiers and evaluation of their surface active and emulsification properties By Mohamed G. Megahed National Research Centre, Fats and Oils Department, Dokki, Cairo, Egypt. RESUMEN preparation of these compounds (Weiss et al., 1971, 1972; Bobaiek, 1977; Akoh and Swanson, 1987, Preparación de esteres de ácidos grasos con sacarosa 1989), however others excluded solvents in such como emulsionantes alimentarios y evaluación de sus propiedades superficiales y emulsionantes. preparation (Heesen et al., 1976; Rizzi and Taylor, 1978). Se ha llevado a cabo un método simple para la preparación de es­ It was planned to use a simple method for teres de sacarosa a partir de ácidos grasos y sacarosa de bajo coste. preparation of emulsifiers from sucrose and different Se han usado ácidos laurico, palmítico y oleíco en su preparación, en fatty acids (lauric, palmitic and oleic) aiming to ausencia de solventes orgánicos. Se obtuvieron rendimientos acepta­ bles del 86.5%, 87.3% y 88.6% para los ásteres del laurico, palmítico develop and improve the method of the preparation y oleíco respectivamente. of sucrose esters. Therefore, it was objective to En los productos se evaluaron sus balances hidrófilo-lipófilo modify the method of Heesen et al., (1976) for the (HLB), sus propiedades de tensión superficial e interfacial así preparation of sucrose emulsifiers (solvent-free como su estabilidad en emulsiones. Los resultados mostraron que estos esteres de sacarosa exhiben propiedades similares a reaction) by replacing the expensive polyalcohols for las de los compuestos preparados comercialmente.
    [Show full text]
  • Research Report A01036: Development of a Method For
    c­ t\.01036 c ( c c c c 0 c c c c :) 0 0 0 o. 0 REPORT FD 04/38 0 DEVELOPMENTOFAMETHODFOR 0 SUCROSE ESTERS (E473) AND 0 SUCROGLYCERIDES (E474) ADDITIVE; IN FOODS 0 0 0 0 0 0 0 0 c ( ( ( ( ( c ( c r ' REPORT FD 04/38 ( ' DEVELOPMENT OF A METHOD FOR. ( SUCROSE ESTERS (E473) AND ( SUCROGLYCERIDES (E474) ADDITIVES ' IN FOODS ( c c ( c l ( c ( ( ( ( ( DEVELOPMENT OF A METHOD FOR SUCROSE ESTERS (E473) AND ( SUCROGLYCERIDES (E474) ADDITIVES IN FOODS ( FINAL REPORT ( c Report Number FD 04/38 c Authors M Scatter, D Roberts ( ( Date March2005 ( Sponsor Food Standards Agency Aviation House 125 Kingsway ' London WC2B 6NH ' Sponsor's Project No. A01036 CSL Project No. L6DG CSLFileNo. FLN7925 Principal Workers M Scatter, D Roberts, D Clarke Contract Manager Dr LCastle Distribution: 1. Dr Dixon (FSA) 5 copies +electronic 2. Prof. Gilbert (CSL) 3. Dr Dennis (CSL) 4. Dr Castle (CSL) ( 5. CSL Library ' ' ' Central Science Laboratory SandHutton York Y0411LZ (UK) Telephone: 01904 462000 Fax: 01904 462111 ( ' (_ ( ( (_ ( Page 1 of 47 ( ' ( ( SUMMARY ( c 1. This report details the findings of Food Standards Agency Project AO 1036: ' Development of a validated method for sucrose esters (E473) and c sucroglycerides (E474) in permitted foods. These additives are complex ' mixtures and have a high molecular weight. These factors prevent their direct ' ' analysis in complex food samples using readily-available techniques. ' ' 2. The analytical strategy adopted therefore was to take advantage of the fact that the additives are soluble in organic solvents. The additives were extracted from foods using a mixture of tetrabydrofuran and ethyl acetate, and the extract freed of any eo-extracted free sugars by washing with saturated sodium sulfate.
    [Show full text]
  • Synthesis of Sucrose Fatty Acid Esters by Using Mixed
    Journal of Oleo Science Copyright ©2020 by Japan Oil Chemists’ Society doi : 10.5650/jos.ess19239 J. Oleo Sci. 69, (7) 693-701 (2020) Synthesis of Sucrose Fatty Acid Esters by Using Mixed Carboxylic-fatty Anhydrides Iteb Trabelsi, Kamel Essid＊ , and Mohamed Hedi Frikha Laboratory of Organic Chemistry LR17ES08: Faculty of sciences in Sfax, Route de Soukra Km 3,5 – BP 1171-3000. Sfax. TUNISIA Abstract: Fatty acid sugar esters are non-ionic surfactant active agents with excellent performance and many uses. This work is devoted to the synthesis of sugar esters by the esterification reaction of sugar with mixed carboxylicpalmitic anhydrides using resin Amberlyst-15 as heterogeneous acid catalyst. These anhydrides should be stable and react as acylating agents. Influence of different reaction parameters, such as the molar ratio (sucrose/anhydride), the type of solvent and the reaction time on the yield of the esterification reaction were studied. The esterification reaction of sucrose with mixed palmitic benzoic anhydride leads to a mixture of sucrose esters of palmitic acid with a good percentage of conversion. The mixed anhydride was both reactive and selective for the preparation of fatty acid ester. Key words: fatty acid, mixed anhydride, heterogeneous acid catalyst, resin Amberlyst-15, esterification, sucrose, acylation of sucrose, sucrose fatty acid esters (SEs) 1 Introduction mixed anhydrides have been often employed in order to Sucrose fatty acid esters（SEs）, commonly called sugar obtain a high yield of ester16）. Mixed anhydrides obtained esters, are nonionic surfactants that have excellent emulsi- from two different carboxylic acids are molecules finding fying, stabilizing, detergency and other useful effect1－4）.
    [Show full text]
  • Sucrose Esters: Their Impact Oh Soybean Oil Utilization
    SUCROSE ESTERS: THEIR IMPACT OH SOYBEAN OIL UTILIZATION William M. Breene Kathleen A. Harrigan Department of Food Science & Nutrition University of Minnesota WHAT ARE SUCROSE ESTERS? Sucrose polyesters (SPE) are not the newest class of food additives on the market but they may well prove to be among the most versatile and controversial. Sucrose itself is unique in its physical and chemical properties; it is a non-reducing disaccharide that is extremely stable except to hydrolysis at the glycoside linkage. It contains eight hydroxyl groups; 3 are primary (Cl', C6', C6) and 5 are secondary, giving ample opportunity for substitution (Table 1). It is highly soluble in water. It is the lowest cost polyhydric alcohol readily available and has the world's highest production of any single pure organic chemical (Parker et al., 1977). Sucrose and its by-products have been used to make ethanol, butanol and acetone by fermentation, and wallboard and paper from sugarcane bagasse, which has also served as a raw material for furfural production (Hass, 1977). Figure 1 depicts the structure of a sucrose octaester; all eight hydroxyl groups are substituted. Table 1. The number of isomers of sucrose derivatives of varying substitution from one (mono) to eight (octa) (Hough, 1977). SUCROSE ISOMERS SUCROSE ISOMERS Mono 8 Penta 56 Di 28 Hexa 28 Tri 56 Hepta 8 Tetra 70 Octa 1 367 4 0 0 RCO Figure 1. Structure of sucrose octaester; R = fatty acid. THE HISTORY OF SUCROSE ESTERS The concept of sucrose polyester production in the U.S. was probably initiated in 1952 when Dr.
    [Show full text]
  • Ultrasound-Assisted Synthesis of Antimicrobial Inulin and Sucrose Esters with 10-Undecylenic Acid
    Article Volume 11, Issue 4, 2021, 12055 - 12067 https://doi.org/10.33263/BRIAC114.1205512067 Ultrasound-Assisted Synthesis of Antimicrobial Inulin and Sucrose Esters with 10-Undecylenic Acid Nadezhda Petkova 1,* , Radka Arabadzhieva 1, Ivanka Hambarliyska 1, Dragomir Vassilev 2 , Gergana Gencheva 1, Yulian Tumbarski 3 , Tsveteslava Ignatova-Ivanova 4, Sevginar Ibryamova 4 , Milena Koleva 2, Panteley Denev 1 1 Department of Organic Chemistry and Inorganic Chemistry, University of Food Technologies, 26 Maritza Blvd., Plovdiv 4002, Bulgaria; [email protected] (N.P.); [email protected] (R.A.); [email protected] (V.H.); [email protected] (P.D.); 2 Department of Physics, Chemistry and Ecology, Technical University of Gabrovo, 4, Hadji Dimitar Str., Gabrovo 5300, Bulgaria; e-mail: [email protected] (D.V.); [email protected] (M.K.); 3 Department of Microbiology, University of Food Technologies, 26 Maritza Blvd., Plovdiv, Bulgaria; [email protected] (Y.T.); 4 Department of Biology, Konstantin Preslavsky University of Shumen, Shumen, Bulgaria; [email protected] (T.I.); e-mail: [email protected] (S.I); * Correspondence: [email protected]; Scopus Author ID 56507003400 Received: 1.12.2020; Revised: 28.12.2020; Accepted: 30.12.2020; Published: 2.01.2021 Abstract: An environmentally friendly and sustainable ultrasound-assisted esterification of long- chained inulin and sucrose with monounsaturated 10-undecylenic acid was performed. The obtained esters were characterized by thin-layer chromatography (TLC), Fourier transforms infrared spectroscopy (FTIR), and nuclear magnetic resonance (NMR) spectroscopy. The spectral analyses demonstrated the successful incorporation of the hydrophobic 10-undecylenoyl residue in the water- soluble carbohydrate backbone. Additionally, the antimicrobial potential of 10-undecylenic esters of inulin and sucrose were tested against nine microorganisms (Gram-positive and Gram-negative bacteria, yeasts, and fungi).
    [Show full text]
  • Safety Assessment of Saccharide Esters As Used in Cosmetics
    Safety Assessment of Saccharide Esters as Used in Cosmetics Status: Final Report Release Date: January 13, 2017 Panel Meeting Date: December 5-6, 2016 The 2016 Cosmetic Ingredient Review Expert Panel members are: Chair, Wilma F. Bergfeld, M.D., F.A.C.P.; Donald V. Belsito, M.D.; Ronald A. Hill, Ph.D.; Curtis D. Klaassen, Ph.D.; Daniel C. Liebler, Ph.D.; James G. Marks, Jr., M.D., Ronald C. Shank, Ph.D.; Thomas J. Slaga, Ph.D.; and Paul W. Snyder, D.V.M., Ph.D. The CIR Director is Lillian J. Gill, D.P.A. This safety assessment was prepared by Laura N. Scott, Scientific Writer/Analyst. © Cosmetic Ingredient Review 1620 L Street, NW, Suite 1200 ♢ Washington, DC 20036-4702 ♢ ph 202.331.0651 ♢ fax 202.331.0088 ♢ [email protected] ABSTRACT This is a safety assessment of 40 saccharide ester ingredients as used in cosmetics. The saccharide esters function in cosmetics as, emollients, skin conditioning-agents, fragrance ingredients, and emulsion stabilizers. The Cosmetic Ingredient Review (CIR) Expert Panel (Panel) reviewed the relevant data for these ingredients. The Panel concluded that the saccharide esters are safe in cosmetics in the present practices of use and concentrations described in this safety assessment. INTRODUCTION This safety assessment includes the 40 saccharide esters listed below. Maltitol Laurate has been reviewed previously by the Panel; in 2008, the Panel concluded that this ingredient is safe as used in cosmetics.1 Although no safety test data were available for Maltitol Laurate, nor was it used in cosmetics at the time it was previously reviewed, available Maltitol and Lauric Acid safety test data were used by the Panel to infer safety for Maltitol Laurate.
    [Show full text]
  • Synthesis of Sugar Esters in Solvent Mixtures by Lipases From
    View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Digital.CSIC Enzyme and Microbial Technology (2005) 36, 391-398 Synthesis of sugar esters in solvent mixtures by lipases from Thermomyces lanuginosus and Candida antarctica B, and their antimicrobial properties Manuel Ferrer a, Juan Soliveri b, Francisco J. Plou a,*, Nieves López-Cortés a, Dolores Reyes-Duarte a, Morten Christensen c, José L. Copa-Patiño b and Antonio Ballesteros a a Departamento de Biocatálisis, Instituto de Catálisis y Petroleoquímica, CSIC, Cantoblanco, 28049 Madrid, Spain. b Departamento de Microbiología y Parasitología, Universidad de Alcalá, Alcalá de Henares, 28871 Madrid, Spain. c Novozymes A/S, Novó Allé, 2880 Bagsvaerd, Denmark Running title: Synthesis and antimicrobial properties of sugar esters Corresponding author: Francisco J. Plou, Departamento de Biocatálisis, Instituto de Catálisis y Petroleoquímica, CSIC, Marie Curie s/n, Campus Cantoblanco, 28049 Madrid, Spain. Fax: 34-91-5854760; E-mail: [email protected]; http://www.icp.csic.es/abg 1 Enzyme and Microbial Technology (2005) 36, 391-398 ABSTRACT The lipases from Thermomyces lanuginosus (immobilized by granulation with silica) and Candida antarctica B (adsorbed on Lewatit, "Novozym 435") were comparatively assayed for the synthesis of sugar esters by transesterification of sugars with fatty acid vinyl esters in 2-methyl-2-butanol:dimethylsulfoxide mixtures. We found that lipase from C. antarctica B is particularly useful for the preparation of 6,6’-di- acylsucrose, whereas T. lanuginosus lipase catalyzes selectively the synthesis of 6-O- acylsucrose. The granulated T. lanuginosus lipase retained more than 80% of its initial activity after 20 cyles of 6 hours.
    [Show full text]