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Journal of Critical Reviews

ISSN- 2394-5125 Vol 7, Issue 9, 2020

COTTONSEED AS A VALUABLE RAW MATERIAL TO OBTAIN TRANS-FREE

Ruzibayev Akbarali Tursunbayevich1 Salijanova Shakhnozakhon Dilmurodovna2, Rakhimov Dilshod Polatovich3

1Dosent, The head of department “Technology of food products”, Tashkent Chemical-Technological Institute, Tashkent, , Email: [email protected] 2PhD student, Tashkent Chemical-Technological Institute, Tashkent, Uzbekistan, Email: [email protected] 3Independent researcher, Tashkent Chemical-Technological Institute, Tashkent, Uzbekistan, email: [email protected]

Received: 25.03.2020 Revised: 15.04.2020 Accepted: 23.05.2020

Abstract The article studies and investigates the production of trans‐free through fractionation of cottonseed oil (CSO), of cottonseed palmitin (CSP) and chemical interesterification of binary blends of fully hydrogenated cottonseed palmitin (FHCSP) and cottonseed oil and their physicochemical changes after the process. Furthermore, it analyzed responses which include composition, , free fatty acid (FFA), slip melting point (SMP) and solid content (SFC) of the fractionated, hydrogenated and interesterified fats. The 40:60 and 50:50 interesterified FHCSP:CSO blends displayed characteristics suited for production of soft tub margarine and stick margarine, respectively. Interesterified blends containing 10-30 % FHCSP could be used for production of puff pastry margarine, roll-in margarine and cake .Trans-free fats obtained through a comprehensive modification of cottonseed oil can be used instead of .

Keywords: cottonseed palmitin, cottonseed oil, chemical interesterification, trans‐free fats, solid fat content, hydrogenation, fractionation

© 2020 by Advance Scientific Research. This is an open-access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/) DOI: http://dx.doi.org/10.31838/jcr.07.09.114 these vegetable are imported from abroad, the cost of INTRODUCTION margarine derived from them is also relatively expensive. Most of Margarine, a food product that is made from a mixture of vegetable the margarine products produced in Uzbekistan are made on the oils and animal fats, milk, flavoring, aromatic and some other basis of hydrogenated fats which called Salomas. Salomas are substances. In physical properties, chemical composition, taste and obtained by catalytic hydrogenation of liquid vegetable oils. As a nutritional value it is close to [1]. Depending on the purpose result of partial hydrogenation, trans acids are also formed in and recipe of use, the following groups of are salomas. After the strict requirement for the amount of trans acid distinguished: for spreading, cooking or baking; for processing and was established, serious problems arose before the manufacturers catering industries; enriched with flavoring additives. In the USA, of margarine based on this oil. Therefore, a lot of research is being Europe and similar foreign countries, are used for done around the world to reduce the amount of trans acids in baking bread, flour confectionery, as well as for frying. In terms of salomas. fat mass, margarines can be as follows: high-fat - 82%, low-fat - 70% and low-calorie - 40 ... 60%[2,3]. Trans-free margarines are used to prepare a wide range of food products [4,5]. In foreign countries, such margarines are made on Demand for margarine products is growing day by day due to the basis of solid fats of plant origin, in particular, palm and palm population growth and limited access to natural butter. However, kernel oil [6-9]. The use of cottonseed oil and its processed as a result of using fats in margarine that do not meet safety products for the production of margarines is of scientific and requirements and excessive consumption of fatty foods, diabetes, practical interest. We have proposed [10-11] fats based on the obesity, and cardiovascular diseases are on the rise. This requires products of catalytic modification of cottonseed oil. in-depth research to improve the technology for producing modified oils for the margarine industry and to develop a , palm and cottonseed oils by the content of certain margarine recipe based on them that meets safety requirements.As fatty acids belong to the palmitic group of the classification of the margarine industry developed, various recipes for margarine fatty oils. Oils of this group are characterized by a high content of were developed and patented. These developments are mainly palmitic acid[12]. Cottonseed oil is the most popular vegetable aimed at reducing the amount of trans acids in margarine, oil in Central Asia. This is due to the national mentality and a expanding the range of fatty raw materials, reducing fat content, large amount of raw materials in the regions. The chemical improving quality and organoleptic characteristics, and much composition of cottonseed oil includes B, E and PP vitamins, more. monounsaturated and saturated fatty acids, which are the main supplier of omega-3 and 6 to the body. oil, which contains Today, palm and coconut oils as well as hydrogenated oils the maximum amount of vitamin E, protects against heart disease (salomas) are used as solid fats for the margarine industry all over and cancer, boosts immunity, maintains potency, helps with the world. Margarine producers in Uzbekistan mainly use palm oil, diabetes and strengthens muscles. The composition of hydrogenated fat and partly . The lack of clear scientific of cottonseed oil consists mainly of unsaturated conclusions on the positive or negative effects of the use of palm oil fatty acids: linoleic, oleic, saturated acids: palmitic, arachidic, in the margarine industry on human health makes it a problem to stearin, myristic. use this oil in this industry. Coconut oil is partly used in the margarine industry due to the fact that it is a rare oil, widely used Modification of fats is a change in the initial properties of fats by in other fields and relatively low melting point. Because both of changing the glyceride and fatty acid content, which is achieved by

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COTTONSEED OIL AS A VALUABLE RAW MATERIAL TO OBTAIN TRANS-FREE MARGARINE interesterification, hydrogenation, fractionation and blending of By partially hydrogenating cottonseed palmitin, a solid oil close fats [3]. to the palm oil performance can be obtained. However, the content of trans acids in salomas obtained during partial MATERIALS AND METHODS hydrogenation is much higher than normal [19]. This limits the Fatty acid analysis & Label Assessment inclusion of salomas in the margarine recipe. It is therefore The fatty acid composition of the samples was measured by advisable to fully hydrogenate the cottonseed palmitin and AGRO-KIMYO STANDART LLC (Tashkent, Uzbekistan) and by the obtain salomas with low trans acid content. In turn, fully Institute of the Chemistry of Plant Substances (Tashkent, hydrogenation of cottonseed palmitin is a more complex process, Uzbekistan). The determination was conducted using the AOAC with high catalyst consumption and long process time. This leads 996.06 method (AOAC International). Fatty acids were to an increase in the cost of salomas. Therefore, in subsequent saponified, methylated and methyl esters were extracted. Then, experiments, work was done to improve the process of fully the methyl esters of the fatty acids were analyzed by capillary gas hydrogenation of cottonseed palmitin and reduce the cost of the chromatography (Agilent Technologies 6890 N) using external product. standards for quantitation. Trans fatty acid was determined by the method of Farag and etc. [14]. Acid and iodine values were We studied the technology of obtaining fully hydrogenated determined according to the AOAC [15] methods. Solid fat cottonseed palmitin in the presence of regenerated and new contents (SFC) were determined using a nuclear magnetic catalyst. The essence of the work is based on the use of new and resonance (NMR) spectrometer according to the AOCS Official regenerated catalysts, as well as the gradual transfer of catalysts Method Cd 16-81. [16]. [22]. Hydrogenation was performed on a cottonseed palmitin with an Raw materials and samples acid value of 0.21 mg KOH/g and a moisture and volatile content Cottonseed (CSO) and sunflower (SFO) oils were used as the of 0.04%. The experiments were carried out at 180 °C by main raw materials for the production of trans-free margarine. stepwise transfer of a new catalyst (N-820) with powdered Refined, bleached, and deodorized SFO and CSO were obtained nickel in the amount of 0.1-0.2% relative to the oil mass and from “Tashkent fat and oil industrial complex” JSC. Regenerated regenerated catalysts in the amount of 0.1-0.4%. In this case, the hydrogenation catalyst and Nysosel-820 catalyst were used to hydrogen consumption is 2 l / min. Initially, the cottonseed obtain hydrogenated cottonseed palmitin. Sodium methoxide, palmitin was hydrogenated in the presence of a regenerated ainteresterification catalyst, was used to obtain the catalyst. After an hour, the process was continued in the interesterified fat.The dry powder of sodium methoxide was presence of a new catalyst. purchased from Fahad Thnayan& Partners for Chemical Products Co (Saudi Arabia). An emulsifier, concentrate was Interesterification is the exchange of radicals in an ether complex used to prepare the margarine emulsion. [13]. In fats and oils technology, this is the process of changing the structure of triglycerides in different phases, liquid and solid Preparation of solid fats for margarine fats in the presence of a catalyst [19]. This process is mainly used For margarine, cottonseed oil was complexly modified to obtain a in the production of soft and ointment edible oils. trans-free solid fat, i.e., fractionated, hydrogenated, and Stearopalmitin is a hydrogenated salomas of cottonseed oil with interesterified. an iodine content of 3-4% J2, consisting only of stearin and Fractionation is the process of breaking down fat or oil into two palmitic glycerides. Stearopalmitin obtained by hydrogenation of (or more) different fractions that differ in terms of fatty acid and cottonseed palmitin does not contain trans-isomers[23]. content [13,17]. This process is widely used in the Fully hydrogenated cottonseed palmitin (FHCSP) and cottonseed production of oils, cottonseed and palm palmitins, and oil(CSO) blends were interesterified under laboratory similar products. conditions.Sodium methoxide was used as catalyst (0.2 %) for Cottonseed oil fractionation is carried out in a crystallizer. chemical interesterification. When reaction temperature of Crystallization occurs at a temperature of 7-10 °C, after which sample reached at the 120 °C, sodium methoxide was added precipitated crystals of solid glycerides are separated on the under reduced pressure and constant agitation for 60 min. The filter. The solid fraction, or the so-called cottonseed palmitin, is temperature was then decreased to 90 °C. To end the reaction used to prepare various types of fat products [18]. with distinctive dark brown color, an excess of citric acid (20 %) was added to neutralize the catalyst. The excess of citric acid and Hydrogenation is the binding of hydrogen to an unsaturated bond in an sodium methoxide was removed with warm water washes and organic compound molecule [19]. In the chemistry of fats and oils, this is the samples were vacuum-dried. the process of obtaining partially solid and solid fats by saturating the unsaturated fatty acids in liquid fats with hydrogen in the presence of a RESULTS AND DISCUSSIONS catalyst. This process is widely used in the production of food salomas The fatty acid contents of cottonseed oil, its fractionated for margarine, shortening, cooking and confectionery oils, as well as cottonseed palmitin and fully hydrogenated palmitin are given in technical salomas for soap, stearin and cosmetics [19-21]. Table 1.

Table 1.Fatty acid composition of fully hydrogenated cottonseed palmitin(FHCSP), cottonseed oil(CSO) and cottonseed palmitin(CSP) Fatty acids %

CSO CSP FHCSP MyristicС14:0 0,6 0,6 0,8

Palmitic С16:0 22,0 37,3 38,3 Palmitoleic С16:1 1,5 1,3 0,0 Stearic С18:0 2,9 4,8 56,7 ArachidicС20:0 0,3 0,3 0,4 Oleic С18:1 20,4 25,6 2,7

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COTTONSEED OIL AS A VALUABLE RAW MATERIAL TO OBTAIN TRANS-FREE MARGARINE

Linoleic С18:2 52,1 30,0 1,1 Linolenic С18:3 0,2 0,1 0,0

Iodine value, % J2 110,0 78,7 4,6 Melting point, ˚С -1 24 59,3

Table 1 shows that when extracting cottonseed palmitin from for the hardness, the fast melting, and release in the mouth cottonseed oil, the fatty acid content in it increased: palmitin and the possible waxy mouth feel at higher temperatures [25]. from 22.0 to 37.3%, stearin from 2.9 to 4.8%, and linol decreased The SFC also has important implications for the overall melting from 52.1 up to 30.0%. With the fully hydrogenation of characteristics of margarines and spreads at various cottonseed palmitin, the fatty acid in salomas increased: palmitic temperatures. The SFC parameter is frequently used to select the acid to 38.3% and stearin to 56.7%, while the ideal fat composition obtained following fat modification. decreased to 2.7% and to 1,1%. The SFC curves of CSO, CSP and FHCSP are illustrated in Figure 1. Fat modification has an important impact on the solid fat content Both temperature and the content of SFA directly affected the (SFC) profile of fat systems, which may be seen as a guideline in rate of SFC evolution. The SFC increase may be due to the content judging whether a certain oil, fat, or blend is suitable for a of SFA (43.0–96.2, Table 1). The CSO showed a reduced SFC particular application [24]. For chocolate, the SFC is responsible almost at all measured temperatures. 100 90 80 70 60 50 40

SFC (%) SFC 30 20 10 0 -10 0 10 20 30 40 50 Temperature (°C) CSO CSP FHCSP

Figure 1.Solid fat content of cottonseed oil (CSO), cottonseed palmitin (CSP) and fully hydrogenated oil cottonseed palmitin (FHCSP)

Chemical interesterification is used in the food industry to produce trans‐free margarines and shortenings. One of the main physical features of fats is their SFC, which correlates with some functional properties such as consistency, spreadability, and sensorial acceptance.

Table 2.Physico-chemical parameters of non-interesterified and interesterified FHCSP and CSO blends № FHCSP, % CSO, % Physico-chemical parameters of blends non-interesterified interesterified FFA,% IV, % J2 Тmp, ˚С FFA,% IV, % J2 Тmp, ˚С 1 10 90 0,15 98,3 41,5 0,13 97,9 27,2 2 15 85 0,17 93,7 43,2 0,13 94,1 29,4 3 20 80 0,16 87,8 45,5 0,14 87,1 32,3 4 25 75 0,18 82,2 48,3 0,14 81,7 35,7 5 30 70 0,19 77,4 51,8 0,15 77,6 39,6 6 40 60 0,21 65,9 54,3 0,15 66,1 46,4 7 50 50 0,23 55,2 56,4 0,16 55,8 47,3

As can be seen from Table 2, the melting temperature of oil and Preparing fat base of margarine fat blend after interesterification was significantly lower than The organoleptic and physical properties of margarine depend that before interesterification. The reason for this is due to the on the physic-chemical properties of oil and fats used in it. composition and properties of the new triglycerides formed as a result of the intermolecular exchange of CSO and FHCSP, which Depending on the purpose, margarine products must have a have 2 different physico-chemical properties. This is due to the certain melting point (fusibility) and ductility. Fusibility is re-grouping of fatty acid radicals in triglycerides, as well as their characterized by the temperature of complete melting, which quantitative changes and their location in the composition. depends on the content and quantitative ratio of solid and liquid fractions: the higher the content of the solid high-melting fraction, the lower the fusibility. Plasticity depends on the ratio of

Journal of critical reviews 574

COTTONSEED OIL AS A VALUABLE RAW MATERIAL TO OBTAIN TRANS-FREE MARGARINE solid to liquid glycerides. Fats, in which the amount of solid We replaced palm oil with interesterifiedfat which is obtained by glycerides is 15-30%, have good ductility and spreadability. In hydrogenated cottonseed palmitin and cottonseed oil blend. dense and non-ductile fat, the content of solid glycerides is more than 30%, and in excessively soft fats - 10-12%. We form the fat base of the margarine on the basis of the initially prepared solid fats and vegetable oils (Table 3). Imported palm oil is used in Uzbekistan to produce trans-free margarine.

Table 3.The fat base of margarines Fat Margarine Ingredients Samples in % Commersial-1 Commersial-2 Suggested Partially hydrogenated oil* 46.0 0 0 Palmoil 38.0 17.0 0 16.0 20.0 20.0 Palm stearin 0 63.0 0 Interesterified fat 0 0 80.0 Total 100 100 100

Melting point of blendТmp, °C 27.7 28.8 28.3

* trans fatty acid content 16.7% Table 3 shows that partially hydrogenated oil, palm stearin and of 78% at 5°C to 16% at 40°C and 62% at 5°C to 13% at 40°C, palm oil in the existing recipes were replaced with interesterified respectively. SFC of PO and PHO decline sharply from their initial fat in the proposed recipe. The use of interesterifiedfat reduces SFC of 71% at 5°C to 0% at 40°C and 48% at 5°C to 0% at 40°C. the melting point of margarine and the amount of trans acid. They are able to maintain the consistency of the margarine at lower temperatures (5°C-15°C), and to soften the margarine Therefore, the SFC curve of the IF wascompared with the texture at serving temperature (25°C-30°C). Combining the common SFC curves of different fats toevaluate their potential individual physical attributes of selected oils and fats will lead to applications for margarine products (Figure 4). the cumulative physical effects required by different In a margarine formulation involving simple blending or margarines.To achieve such an SFC profile in a conventional soft interesterifying several oils and fats, the shape of the curve of margarine formulation, partially hydrogenated soft oil is SFC to the function of temperature is able to show the expected commonly used. CSO has a flat SFC profile with 0% SFC from its melting profile of the final product [26]. The SFC curve can be initial temperature at 5°C (Figure 1); thus, it is liquid in nature at used to determine the special applications of fats [27]. The 5°C and this helps to provide the soft texture to the margarine individual SFC profile of selected oils and fats are shown in . Figure 2. SFC of PS and IF declines sharply from their initial SFC 90 80 70 60 50

40 SFC (%) SFC 30 20 10 0 0 10 20 30 40 50 Temperature (°C) PHO PO PS IF

Figure 2.Solid fat content of oils and fats used in this study. (SFC: Solid fat content, PHO: partially hydrogenated oil, PO: palm oil, PS: palm stearin, IF: interesterified fat)

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COTTONSEED OIL AS A VALUABLE RAW MATERIAL TO OBTAIN TRANS-FREE MARGARINE

Fatty acid compositions affects SFC profile in formulations with 3.2and6.4 % at 35°C. The highest SFC values were obtained for the same type of hard stock. Formulations of samples SM, CP-1 SM at 10-25°C and for CP-2 at 30-40°C which probably resulted and CP-2 as shown in Table 2 contain palm stearin, palm oil, but from the highest total SFA content. comprise different oils and fats in the semi-solid and liquid A trans-free margarine recipe was formulated using the formed portions. The SFC values of margarines (Figure 3) were 30.5, fat base (Table 4). 27.2 and 29.1% at 10°C, 22.2, 16.6and21.3% at 20°C, and 8.4,

Table 4. A trans-free margarine recipe № Margarine ingredients % 1 Fat base 71,6 2 Dye 0,1 3 Emulsifier 0,2 4 Milk 10 5 Salt 0,4 6 Phosphatide concentrate 0,5 7 0,4 8 Antioxidant 0,05 9 Water 16,75 Total 100

Margarine products were prepared in the laboratory on the basis margarine in the proposed recipe differed from the existing of the developed recipes. For this, the components of the margarine samples by its high degree of dispersion and formulation were mixed, an emulsion formed, and the emulsion plasticity. In addition, the use of interesterified oil in its was cooled and crystallized. When it was analyzed the physico- composition allows to increase its plasticity and stability. chemical properties of the prepared margarine products, the

35

30

25

20

15 SFC (%) SFC 10

5

0 0 10 20 30 40 50 Temperature (°C) SM CP-1 CP-2

Figure 3. Solid fat content curves (%) of margarines (SM:suggested margarine, CP-1:First commercial present margarine, CP-2: Second commercial present margarine).

Average SFC values of different margarines were different from need to be hydrogenated in orderto improve their functionality. each other (P<0.01) at all applied temperatures. The SFC values Cottonseed oil will continue to be important ingredients in the at 20 °C were higher than 20% in all of our samples. The highest manufactureof margarines requiring solid fatswith and without SFC values were obtained for samples SM and CP-2. hydrogenation. It has been shown that cottonseed oilproducts performed very well in various types ofmargarines and in several CONCLUSIONS bakery applications. They also performedvery well as frying oils. Manufacturers may choose raw materials from any category of oils andfats to the margarine production. Certain liquid oils may

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COTTONSEED OIL AS A VALUABLE RAW MATERIAL TO OBTAIN TRANS-FREE MARGARINE

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