NZ772540B2 - Method for lowering iodine value of glyceride - Google Patents
Method for lowering iodine value of glyceride Download PDFInfo
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- NZ772540B2 NZ772540B2 NZ772540A NZ77254019A NZ772540B2 NZ 772540 B2 NZ772540 B2 NZ 772540B2 NZ 772540 A NZ772540 A NZ 772540A NZ 77254019 A NZ77254019 A NZ 77254019A NZ 772540 B2 NZ772540 B2 NZ 772540B2
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- New Zealand
- Prior art keywords
- glyceride
- iodine value
- fatty acid
- lowering
- reaction
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- 125000005456 glyceride group Chemical group 0.000 title claims abstract description 99
- 229910052740 iodine Inorganic materials 0.000 title claims abstract description 86
- 239000011630 iodine Substances 0.000 title claims abstract description 86
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 title claims abstract description 85
- 238000000034 method Methods 0.000 title claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 118
- 108090001060 Lipase Proteins 0.000 claims abstract description 51
- 102000004882 Lipase Human genes 0.000 claims abstract description 51
- 150000004671 saturated fatty acids Chemical class 0.000 claims abstract description 49
- 239000004367 Lipase Substances 0.000 claims abstract description 42
- 235000019421 lipase Nutrition 0.000 claims abstract description 42
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 27
- 239000003513 alkali Substances 0.000 claims abstract description 18
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 121
- 235000021314 Palmitic acid Nutrition 0.000 claims description 51
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 51
- 238000003756 stirring Methods 0.000 claims description 35
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 34
- 150000004665 fatty acids Chemical group 0.000 claims description 30
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 29
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 21
- 235000021355 Stearic acid Nutrition 0.000 claims description 15
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 15
- 239000008117 stearic acid Substances 0.000 claims description 15
- 239000005639 Lauric acid Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- 239000011261 inert gas Substances 0.000 claims description 6
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 4
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 4
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 3
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 claims description 3
- 235000021360 Myristic acid Nutrition 0.000 claims description 3
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 2
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 2
- 229960002446 octanoic acid Drugs 0.000 claims description 2
- -1 saturated fatty acid salt Chemical class 0.000 abstract description 10
- 238000007086 side reaction Methods 0.000 abstract description 7
- 230000003197 catalytic effect Effects 0.000 abstract description 4
- 238000011065 in-situ storage Methods 0.000 abstract description 4
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 52
- 235000019482 Palm oil Nutrition 0.000 description 43
- 239000002540 palm oil Substances 0.000 description 43
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000012074 organic phase Substances 0.000 description 32
- 239000000047 product Substances 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 239000000344 soap Substances 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000010438 heat treatment Methods 0.000 description 18
- 239000000741 silica gel Substances 0.000 description 18
- 229910002027 silica gel Inorganic materials 0.000 description 18
- 238000001179 sorption measurement Methods 0.000 description 18
- 229910001873 dinitrogen Inorganic materials 0.000 description 16
- 238000005119 centrifugation Methods 0.000 description 15
- 235000014113 dietary fatty acids Nutrition 0.000 description 15
- 239000000194 fatty acid Substances 0.000 description 15
- 229930195729 fatty acid Natural products 0.000 description 15
- 235000021588 free fatty acids Nutrition 0.000 description 15
- 238000000199 molecular distillation Methods 0.000 description 15
- 238000004321 preservation Methods 0.000 description 14
- 239000006228 supernatant Substances 0.000 description 14
- 239000003346 palm kernel oil Substances 0.000 description 10
- 235000019865 palm kernel oil Nutrition 0.000 description 10
- 108010084311 Novozyme 435 Proteins 0.000 description 9
- 244000299461 Theobroma cacao Species 0.000 description 8
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 8
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 8
- 235000014121 butter Nutrition 0.000 description 8
- 235000001046 cacaotero Nutrition 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000005809 transesterification reaction Methods 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 235000003441 saturated fatty acids Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 229940045870 sodium palmitate Drugs 0.000 description 2
- GGXKEBACDBNFAF-UHFFFAOYSA-M sodium;hexadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCC([O-])=O GGXKEBACDBNFAF-UHFFFAOYSA-M 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108010048733 Lipozyme Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960001947 tripalmitin Drugs 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
Abstract
method for lowering the iodine value of glyceride, comprising: enabling glyceride, saturated fatty acid and alkali to perform catalytic reaction under the action of lipase so as to obtain glyceride having a low iodine value. By means of sufficient quantity of saturated fatty acid residues provided by a saturated fatty acid salt formed in-situ by corresponding saturated fatty acid and alkali and the catalytic action of non-specific lipase, the reaction conditions are mild; the side reaction is rare; and the iodine value of glyceride is effectively lowered.
Description
METHOD FOR LOWERING IODINE VALUE OF GLYCERIDE FIELD OF INVENTION ?001 ? This present disclosure generally relates to the technical field of synthesis and processing of glycerides, and in particular, to a method for lowering iodine value of glycerides.
BACKGROUND OF INVENTION ?002 ? In industrial production, it is necessary to produce glycerides with low iodine value serving as raw materials for chemical production. However, existing methods to increase the saturation of glycerides are mainly carried out by chemical catalysis, and the catalysis reactions require high temperature and strict process conditions. Therefore, a simple process that can effectively lower the iodine value of glycerides is necessary.
SUMMARY OF INVENTION ?003 ? The object of the present disclosure is to provide a method for lowering iodine value of glycerides, which can increase the content of saturated fatty acids in glycerides, thereby effectively reducing the iodine value of glycerides, under simple reaction conditions and few side reactions. ?004 ? The present disclosure provides the following technical solutions to solve technical issues. ?005 ? The present disclosure provides a method for lowering an iodine value of a glyceride, which comprises: enabling a glyceride, a saturated fatty acid, and an alkali to undergo a catalytic reaction under action of a lipase. ?006 ? On the basis of saturated fatty acid residues contained in the glyceride, a sufficient amount of saturated fatty acid residues are provided by the corresponding saturated fatty acid with catalysis of the lipase to achieve mild reaction conditions, few side reactions, and low iodine value of the resulting glyceride.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS ?007 ? In order to make the objectives, technical solutions, and advantages of embodiments of the present disclosure clear, the technical solutions in the embodiments of the present disclosure are described clearly and completely below. If specific conditions are not specified in the embodiments or examples, it can be carried out in accordance with the conventional conditions or the conditions recommended by the manufacturer.
Reagents and instruments without the manufacturer's indication are all known products that can be purchased commercially. ?008 ? A method for lowering an iodine value of a glyceride according to embodiments of the present disclosure is specifically described below. ?009 ? Some embodiments of the present disclosure provide a method of lowering the iodine value of the glyceride, which comprises: enabling a glyceride, a saturated fatty acid and an alkali to undergo a catalytic reaction under action of a lipase to obtain the glyceride with high content of saturated fatty acids. ?0010 ? Iodine value is an index of degree of unsaturation in an organic compound. Iodine value refers to grams of iodine that can be absorbed (added) in 100g of material, mainly used for the determination of oils, fatty acids, waxes and polyesters. The greater the degree of unsaturation, the higher the iodine value. ?0011 ? The glyceride can be monoglyceride, diglyceride, triglyceride, or a mixture of diglyceride and triglyceride. ?0012 ? It should be noted that the catalytic reaction includes transesterification and esterification. When the glyceride is mainly triglyceride, the transesterification is mainly carried out. When the glyceride includes part of diglyceride or part of monoglyceride, there are also esterification. ?0013 ? In some embodiments, the glyceride is glyceride with saturated fatty acid residues. Preferably, the iodine value of the glyceride is greater than 20. Preferably, at least a saturated fatty acid corresponding to saturated fatty acid residues contained in the glyceride is equivalent to the one of the saturated fatty acids added in the reaction system. On the basis of partial ester bonds with specific saturated fatty acid residues in the glyceride, a large amount of fatty acid residues are provided by specific fatty acid salts which are in-situ formed through the reaction between the specific saturated fatty acid and the alkali, thereby catalyzing transesterification and esterification reactions of the fatty acid residues by the lipase. The reactions result in mild reaction conditions, few side reactions and low iodine value of the formed glycerides. ?0014 ? In some embodiments, the amount of the saturated fatty acid is based on the ratio of the glyceride to the saturated fatty acid, and the ratio of saturated fatty acid residues to the total fatty acid residues in the reaction system greater than or equal to 90%, preferably greater than 92%, and more preferably greater than 95%. For example, the saturated fatty acid may be added, so that the ratio of saturated fatty acid residues to the total fatty acid residues in the reaction system is 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98% etc. ?0015 ? In some embodiments, the molar ratio of the alkali to the saturated fatty acid is not more than 1, preferably, the molar ratio of the alkali to the fatty acid is not more than 0.025, and more preferably, the molar ratio of alkali to fatty acid ranges from 0.025 to 0.0001. ?0016 ? In some embodiments, the alkali is any of NaOH, KOH, NaOC H , KOC H , NaOCH , KOCH , solid base catalysts and mixtures 2 5 2 5 3 3 thereof. More preferably, the alkali is NaOH or KOH. By setting the ratio of the reactants, the progress of the transesterification reaction of the esterification reaction can be fully satisfied, and thereby the reactants can be fully contacted to obtain a reaction product with a lower iodine value. ?0017 ? In some embodiments, the lipase may be a non-specific lipase, and its addition amount is 0.05-10% of glycerides, preferably 0.1-8% of glycerides. In a further preferred solution, the addition amount of Novozym 435 is 4-8%, the addition amount of Lipase DF "Amano" 15 ranges 0.1 to 1%, the addition amount of LipozymeTLIM is 4-8%, or the addition amount of LipaseAY30G is added in 0.1-1%. For example, the addition amount of the non- specific lipase can be 0.05%, 0.1%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8% or 9%.
The addition amount of non-specific enzyme has an important influence on the reaction process. If the addition amount is too low, the catalytic effect cannot be achieved. If the addition amount is too high, the costs increase, and the contact between the reactants in the reaction process is affected, thereby resulting in poor reaction effect. Therefore, the addition amount of the non- specific lipase in the above range can fully achieve the catalytic effect on the reaction, so that the reaction can proceed thoroughly in the set reaction time. ?0018 ? In some embodiments, the lipase includes at least one of non-specific lipases and a specific lipase. Preferably, the lipase is a non-specific lipase, and the non-specific lipase includes at least one of Novozym 435, Lipase DF "Amano" 15, LipozymeTLIM and LipaseAY30G. For example, the non- specific lipase can be Novozym 435 or Lipase DF "Amano" 15, or a mixture of Novozym 435 and Lipase DF "Amano" 15. Preferably, the non-specific lipase is Lipase DF "Amano" 15. ?0019 ? In some embodiments, the temperature of the catalytic reaction is 30-90°C, preferably 35-85°C. More preferably, the reaction temperature of the LipozymeTLIM is 65-70°C, the reaction temperature of the Novozym 435 is 75-85°C, the reaction temperature of Lipase DF "Amano" 15 is -40°C, the reaction temperature of the LipaseAY30G is 35-40°C.The catalytic reaction time is 0.5-9 hours, and the preferred reaction time is 1-4 hours. At this reaction temperature, the reaction temperature is lower than that of traditional chemical catalysts, and the reaction easily proceeds. The reaction temperature can be kept constant by heating in a water bath. The heating in the water bath is uniform and the effect of heat transferring effectively makes the reaction easy.
Of course, other heating methods, such as furnace heating, can also be used to maintain the reaction temperature. ?0020 ? In some embodiments, the saturated fatty acid as a reactant in the reaction is selected from at least one of palmitic acid, stearic acid, caprylic acid, capric acid, lauric acid, myristic acid and arachidic acid. Preferably, it is at least one of palmitic acid, stearic acid, myristic acid and lauric acids, and more preferably at least one of palmitic acid and stearic acid. For example, palmitic acid or stearic acid, or saturated fatty acid may also be a mixture of palmitic acid and stearic acid in a certain ratio. ?0021 ? In the embodiment of the present disclosure, the purpose of adding alkali is that the alkali can in -situ react with fatty acids in the reaction system to form fatty acid salts. The fatty acid salts are a type of strong alkali weak acid salt with strong ionization ability and strong fatty acid residue activity.
The ability of fatty acid salts to provide fatty acid residues is much greater than that of free fatty acids or fatty acid esters, thereby accelerating the rate of the transesterification reaction, shortening the reaction time, reducing the amount of the lipase and reducing costs. According to some embodiments, the glyceride containing saturated fatty acid residues may be cocoa butter, coconut oil, palm kernel oil or palm oil. Preferably, the glyceride containing saturated fatty acid residues is palm oil. ?0022 ? In some embodiments, enabling undergoing the catalytic reaction specifically comprises steps of mixing glyceride with the saturated fatty acid and the alkali, adding the lipase, and stirring under a condition of introducing inert gas. The protective effect of inert gas helps to avoid the influence of outside air on the reaction, and the stirring can make the reactants fully contact to make the reaction complete and fast. Furthermore, the catalytic reaction preferably includes steps of mixing the glyceride containing saturated fatty acid residues with the saturated fatty acid salts, and then adding the non-specific lipase, and stirring under a condition of introducing inert gas.
In some embodiments, the speed of stirring during the agitation reaction ranges from 300 to 600 r/min, preferably 400 to 500 r/min. ?0023 ? In some embodiments, the inert gas can be selected from nitrogen, neon, argon, etc. Preferably, the inert gas is nitrogen. ?0024 ? In some embodiments, the reaction system also comprises a solvent. By adding a solvent to the reaction system, the reactants and reaction products can be dissolved in the solvent, thereby it is beneficial to the phase flow between the reactants and mass transfer effect to achieve a desirable effect during the reaction. Moreover, the solvent can also extract the product when the reaction is completed. The solvent can be added to the reaction system together with the reactants, or gradually added to the reaction system during the reaction. In some embodiments, the solvent is n-hexane. In some embodiments, the addition amount of the solvent is 1 to 2 times to the mass of the raw material glycerides. ?0025 ? In some embodiments, after the catalytic reaction, the soap in the organic phase is removed by silica gel adsorption and then the concentration step can be performed. For example, after the catalytic reaction, centrifugation may be performed, and then the soap in the organic phase can be removed by silica gel adsorption. According to some embodiments, the excess fatty acids are removed after the catalytic reaction. Preferably, molecular distillation is performed to remove the excess fatty acids. ?0026 ? It should be noted that for calculating the addition amounts, the mass ratio of the saturated fatty acid to the glyceride can be based on the ratio of the iodine value of the glyceride to the expected iodine value of the product, so that the mass ratio of the saturated fatty acid to the glyceride is not less than the ratio of the iodine value of the glyceride to the expected iodine value of the product minus one. Some embodiments of the present disclosure provide a method for lowering the iodine value of glycerides, which comprises: enabling glycerides containing palmitic acid residues, palmitic acid and alkalis to undergo a catalytic reaction under the action of non-specific lipase to obtain tripalmitin with low iodine value. The glyceride used as raw material is triglycerides. ?0027 ? In some embodiments, the glyceride with low iodine value can also be used to synthesize USU-type triglycerides, such as 1,3-dioleic acid- 2-palmitic acid triglyceride (OPO). ?0028 ? The method can be that the prepared glyceride with low iodine value and unsaturated fatty acid or unsaturated fatty acid glyceride are subjected to Sn-1.3 enzymatic directed reaction under the catalysis of sn-1,3 specific lipase to prepare USU-type triglycerides . ?0029 ? The features and performance of the present disclosure will be further described in detail below in conjunction with examples. ?0030 ? Example 1 ?0031 ? Palmitic acid was weighed out according to the amount of palmitic acid residues of palm oil to keep the ratio of palmitic acid residues to the total fatty acid residues in the reaction system was 90%. 1000g palm oil stearin and 1000ml n-hexane were placed into four-necked flask with heating in a water bath until the palm oil stearin dissolved, and then mixed with the palmitic acid and sodium methoxide. The molar ratio of sodium methoxide and palmitic acid is 0.02. ?0032 ? Then, after nitrogen gas was introduced, the temperature of the water bath was 35° C, and the stirring speed was 400 r/min. After stirring until uniform, 5g of non-specific lipase Lipase DF "Amano" 15 was added, and the reaction was stirred for 4 hours with heat preservation. The supernatant of the organic phase was obtained by centrifugation, the soap in the organic phase was removed by silica gel adsorption, and free fatty acids were removed by molecular distillation to obtain a light yellow solid. The palmitic acid content at the sn-2 position is 88.5%. ?0033 ? Wherein, the palm oil used for the reaction has an iodine value of 35, and the glyceride product obtained after the reaction has an iodine value of 7.5. ?0034 ? Example 2 ?0035 ? Palmitic acid and stearic acid were weighed out according to the amount of palmitic acid residues and stearic acid residues of palm oil to keep the ratio of palmitic acid residues and stearic acid residues to the total fatty acid residues in the reaction system was 92%. 1000g palm oil stearin and 1200ml n-hexane were placed into four-necked flask with heating in a water bath until the palm oil stearin dissolved, and then mixed with the palmitic acid, stearic acid and NaOH. The molar ratio of palmitic acid, stearic acid and NaOH is 8:2:0.1. After nitrogen gas was introduced, the temperature of the water bath was 40° C, and the stirring speed was 350 r/min. After stirring until uniform, 10g of non-specific lipase LipaseAY30G5 was added, and the reaction was stirred for 1 hours with heat preservation. The supernatant of the organic phase was obtained by centrifugation, the soap in the organic phase was removed by silica gel adsorption, and free fatty acids were removed by molecular distillation to obtain a light yellow solid. The palmitic acid content at the sn-2 position is 87.8%. ?0036 ? Wherein, the palm oil used for the reaction has an iodine value of 35, and the glyceride product obtained after the reaction has an iodine value of 7.1. ?0037 ? Example 3 ?0038 ? Palmitic acid was weighed out according to the amount of palmitic acid residues of palm oil to keep the ratio of palmitic acid residues to the total fatty acid residues in the reaction system was 94%. 1000g palm oil stearin and 1500ml n-hexane were placed into four-necked flask with heating in a water bath until the palm oil stearin dissolved, and then mixed with the palmitic acid and potassium hydroxide. The molar ratio of potassium hydroxide and palmitic acid is 0.025. ?0039 ? Then, after nitrogen gas was introduced, the temperature of the water bath was 85° C, and the stirring speed was 500 r/min. After stirring until uniform, 50g of non-specific lipase Novozym 435 was added, and the reaction was stirred for 1 hours with heat preservation. The supernatant of the organic phase was obtained by centrifugation, the soap in the organic phase was removed by silica gel adsorption, and free fatty acids were removed by molecular distillation to obtain a light yellow solid. The palmitic acid content at the sn-2 position is 91.3%. ?0040 ? Wherein, the palm oil used for the reaction has an iodine value of 35, and the glyceride product obtained after the reaction has an iodine value of 7.3. ?0041 ? Example 4 ?0042 ? Palmitic acid was weighed out according to the amount of palmitic acid residues of palm oil to keep the ratio of palmitic acid residues to the total fatty acid residues in the reaction system was 94%. 1000g palm oil stearin and 2000ml n-hexane were placed into four-necked flask with heating in a water bath until the palm oil stearin dissolved, and then mixed with the palmitic acid and sodium ethoxide. The molar ratio of sodium ethoxide and palmitic acid is 0.00125. ?0043 ? Then, after nitrogen gas was introduced, the temperature of the water bath was 65° C, and the stirring speed was 400 r/min. After stirring until uniform, 40g of non-specific lipase LipozymeTLIM was added, and the reaction was stirred for 2 hours with heat preservation. The supernatant of the organic phase was obtained by centrifugation, the soap in the organic phase was removed by silica gel adsorption, and free fatty acids were removed by molecular distillation to obtain a light yellow solid. The palmitic acid content at the sn-2 position is 93.1%. ?0044 ? Wherein, the palm oil used for the reaction has an iodine value of 35, and the glyceride product obtained after the reaction has an iodine value of 5.4. ?0045 ? Example 5 ?0046 ? Palmitic acid was weighed out according to the amount of palmitic acid residues of palm oil to keep the ratio of palmitic acid residues to the total fatty acid residues in the reaction system was 96%. 1000g palm oil stearin and 2000ml n-hexane were placed into four-necked flask with heating in a water bath until the palm oil stearin dissolved, and then mixed with the palmitic acid and potassium hydroxide. The molar ratio of potassium hydroxide and palmitic acid is 0.016. ?0047 ? Then, after nitrogen gas was introduced, the temperature of the water bath was 40° C, and the stirring speed was 380 r/min. After stirring until uniform, 10g of non-specific lipase Lipase DF "Amano" 15 was added, and the reaction was stirred for 2 hours with heat preservation. The supernatant of the organic phase was obtained by centrifugation, the soap in the organic phase was removed by silica gel adsorption, and free fatty acids were removed by molecular distillation to obtain a light yellow solid. The palmitic acid content at the sn-2 position is 93.8%. ?0048 ? Wherein, the palm oil used for the reaction has an iodine value of 35, and the glyceride product obtained after the reaction has an iodine value of 6.2. ?0049 ? Example 6 ?0050 ? Lauric acid was weighed out according to the amount of lauric acid residues of palm kernel oil to keep the ratio of lauric acid residues to the total fatty acid residues in the reaction system was 90%. 1000g palm kernel oil and 1000ml n-hexane were placed into four-necked flask with heating in a water bath until the palm oil dissolved, and then mixed with the lauric acid and potassium methoxide. The molar ratio of potassium methoxide and lauric acid is 0.016. ?0051 ? Then, after nitrogen gas was introduced, the temperature of the water bath was 85° C, and the stirring speed was 400 r/min. After stirring until uniform, 80g of non-specific lipase Novozym 435 was added, and the reaction was stirred for 0.5 hours with heat preservation. The supernatant of the organic phase was obtained by centrifugation, the soap in the organic phase was removed by silica gel adsorption, and free fatty acids were removed by molecular distillation to obtain a light yellow solid. The palmitic acid content at the sn-2 position is 89.5%. ?0052 ? Wherein, the palm kernel oil used for the reaction has an iodine value of 30, and the glyceride product obtained after the reaction has an iodine value of 7.2. ?0053 ? Example 7 ?0054 ? Lauric acid was weighed out according to the amount of lauric acid residues of palm kernel oil to keep the ratio of lauric acid residues to the total fatty acid residues in the reaction system was 92%. 1000g palm kernel oil and 1200ml n-hexane were placed into four-necked flask with heating in a water bath until the palm oil dissolved, and then mixed with the lauric acid and potassium methoxide. The molar ratio of potassium ethoxide and lauric acid is 0.0025. ?0055 ? Then, after nitrogen gas was introduced, the temperature of the water bath was 35° C, and the stirring speed was 300 r/min. After stirring until uniform, 10g of non-specific lipase Lipase DF "Amano" 15 was added, and the reaction was stirred for 2 hours with heat preservation. The supernatant of the organic phase was obtained by centrifugation, the soap in the organic phase was removed by silica gel adsorption, and free fatty acids were removed by molecular distillation to obtain a light yellow solid. The palmitic acid content at the sn-2 position is 91.4%. ?0056 ? Wherein, the palm kernel oil used for the reaction has an iodine value of 30, and the glyceride product obtained after the reaction has an iodine value of 6.4. ?0057 ? Example 8 ?0058 ? Lauric acid was weighed out according to the amount of lauric acid residues of palm kernel oil to keep the ratio of lauric acid residues to the total fatty acid residues in the reaction system was 97%. 1000g palm kernel oil and 2000ml n-hexane were placed into four-necked flask with heating in a water bath until the palm oil dissolved, and then mixed with the lauric acid and NaOH. The molar ratio of NaOH and lauric acid is 0.0001. ?0059 ? Then, after nitrogen gas was introduced, the temperature of the water bath was 40° C, and the stirring speed was 350 r/min. After stirring until uniform, 10g of non-specific lipase Lipase DF "Amano" 15 was added, and the reaction was stirred for 5 hours with heat preservation. The supernatant of the organic phase was obtained by centrifugation, the soap in the organic phase was removed by silica gel adsorption, and free fatty acids were removed by molecular distillation to obtain a light yellow solid. The palmitic acid content at the sn-2 position is 95.4%. ?0060 ? Wherein, the palm kernel oil used for the reaction has an iodine value of 30, and the glyceride product obtained after the reaction has an iodine value of 5.1. ?0061 ? Example 9 ?0062 ? Stearic acid was weighed out according to the amount of stearic acid residues of cacao butter to keep the ratio of stearic acid residues to the total fatty acid residues in the reaction system was 93%. 1000g cacao butter and 1500ml n-hexane were placed into four-necked flask with heating in a water bath until the cacao butter dissolved, and then mixed with the stearic acid and solid acid catalyst (CAS: 5348). The molar ratio of solid acid catalyst and stearic acid is 0.016. ?0063 ? Then, after nitrogen gas was introduced, the temperature of the water bath was 40° C, and the stirring speed was 400 r/min. After stirring until uniform, 5g of non-specific lipase Lipase DF "Amano" 15 was added, and the reaction was stirred for 2 hours with heat preservation. The supernatant of the organic phase was obtained by centrifugation, the soap in the organic phase was removed by silica gel adsorption, and free fatty acids were removed by molecular distillation to obtain a light yellow solid. The palmitic acid content at the sn-2 position is 91.1%. ?0064 ? Wherein, the cacao butter used for the reaction has an iodine value of 28, and the glyceride product obtained after the reaction has an iodine value of 5.8. ?0065 ? Example 10 ?0066 ? Stearic acid was weighed out according to the amount of stearic acid residues of cacao butter to keep the ratio of stearic acid residues to the total fatty acid residues in the reaction system was 93%. 1000g cacao butter and 1500ml n-hexane were placed into four-necked flask with heating in a water bath until the cacao butter dissolved, and then mixed with the stearic acid and potassium hydroxide. The molar ratio of potassium hydroxide and stearic acid is 0.001. ?0067 ? Then, after nitrogen gas was introduced, the temperature of the water bath was 75° C, and the stirring speed was 440 r/min. After stirring until uniform, 60g of non-specific lipase Novozym 435 was added, and the reaction was stirred for 1 hours with heat preservation. The supernatant of the organic phase was obtained by centrifugation, the soap in the organic phase was removed by silica gel adsorption, and free fatty acids were removed by molecular distillation to obtain a light yellow solid. The palmitic acid content at the sn-2 position is 92.3%. ?0068 ? Wherein, the cacao butter used for the reaction has an iodine value of 28, and the glyceride product obtained after the reaction has an iodine value of 6.0. ?0069 ? Example 11 ?0070 ? Palmitic acid was weighed out according to the amount of palmitic acid residues of palm oil stearin to keep the ratio of palmitic acid residues to the total fatty acid residues in the reaction system was 85%. 1000g palm oil stearin and 2000ml n-hexane were placed into four-necked flask with heating in a water bath until the palm oil stearin dissolved, and then mixed with the palmitic acid and potassium hydroxide. The molar ratio of potassium hydroxide and palmitic acid is 0.016. ?0071 ? Then, after nitrogen gas was introduced, the temperature of the water bath was 40° C, and the stirring speed was 380 r/min. After stirring until uniform, 10g of non-specific lipase Lipase DF "Amano" 15 was added, and the reaction was stirred for 2 hours with heat preservation. The supernatant of the organic phase was obtained by centrifugation, the soap in the organic phase was removed by silica gel adsorption, and free fatty acids were removed by molecular distillation to obtain a light yellow solid. The palmitic acid content at the sn-2 position is 80.4%. ?0072 ? Wherein, the palm oil stearin used for the reaction has an iodine value of 35, and the glyceride product obtained after the reaction has an iodine value of 19. ?0073 ? Example 12 ?0074 ? Palmitic acid was weighed out according to the amount of palmitic acid residues of palm oil stearin to keep the ratio of palmitic acid residues to the total fatty acid residues in the reaction system was 94%. 1000g palm oil stearin was placed into four-necked flask with heating in a water bath until the palm oil stearin dissolved, and then mixed with the palmitic acid and potassium hydroxide. The molar ratio of potassium hydroxide and palmitic acid is 0.025. ?0075 ? Then, after nitrogen gas was introduced, the temperature of the water bath was 85° C, and the stirring speed was 500 r/min. After stirring until uniform, 50g of non-specific lipase Novozym 435 was added, and the reaction was stirred for 1 hours with heat preservation. After extraction with 2000mL n-hexane, the soap in the organic phase was removed by silica gel adsorption, and free fatty acids were removed by molecular distillation to obtain a light yellow solid. The palmitic acid content at the sn-2 position is 88.2%. ?0076 ? Wherein, the palm oil stearin used for the reaction has an iodine value of 35, and the glyceride product obtained after the reaction has an iodine value of 20.3. ?0077 ? Example 13 ?0078 ? Palmitic acid was weighed out according to the amount of palmitic acid residues of palm oil to keep the ratio of palmitic acid residues to the total fatty acid residues in the reaction system was 96%. 1000g palm oil stearin and 2000ml n-hexane were placed into four-necked flask with heating in a water bath until the palm oil stearin dissolved, and then mixed with the palmitic acid and potassium hydroxide. The molar ratio of potassium hydroxide and palmitic acid is 0.016. Then, after nitrogen gas was introduced, the temperature of the water bath was 65° C, and the stirring speed was 380 r/min.
After stirring until uniform, 60g of immobilized 1, 3 specific lipase Lipozyme RMIM was added, and the reaction was stirred for 2 hours with heat preservation. The supernatant of the organic phase was obtained by centrifugation, the soap in the organic phase was removed by silica gel adsorption, and free fatty acids were removed by molecular distillation to obtain a light yellow solid. The palmitic acid content at the sn-2 position is 76.6%. ?0079 ? Wherein, the palm oil used for the reaction has an iodine value of 35, and the glyceride product obtained after the reaction has an iodine value of 19.2. ?0080 ? Example 14 ?0081 ? The only difference between Example 14 and Example 5 is that the amount of the non-specific lipase Lipase DF "Amano" 15 added is 0.5 g. The iodine value of the glyceride product obtained after the reaction was 13.1. ?0082 ? Example 15 ?0083 ? The only difference between Example 15 and Example 5 is that the amount of the non-specific lipase Lipase DF "Amano" 15 added is 100 g. The iodine value of the glyceride product obtained after the reaction was 6.0. ?0084 ? Example 16 ?0085 ? The only difference between Example 16 and Example 5 is that the temperature of the water bath for the catalytic reaction is 30°C. The iodine value of the glyceride product obtained after the reaction was 14.2. ?0086 ? Example 17 ?0087 ? The only difference between Example 17 and Example 5 is that the temperature of the water bath for the catalytic reaction is 90°C. The iodine value of the glyceride product obtained after the reaction was 30.4. ?0088 ? Comparative example 1 ?0089 ? 30kg palmitic acid stearin was weighed out and placed into a 100L pilot reactor, 5kg sodium palmitate was added, heated and stirred while nitrogen gas introduced. The reaction temperature was kept at 180° C, and the stirring speed was 300 r/min. The reaction was stirred for 12 hours. Then the reaction system was cooled down to 50 ?. N-hexane was added to dissolve solid. The supernatant of the organic phase was obtained by centrifugation, the soap in the organic phase was removed by silica gel adsorption. Light yellow solid was obtained by concentration process. The palmitic acid content at the sn-2 position is 63.6%. ?0090 ? Wherein, the palm oil stearin used for the reaction has an iodine value of 35, and the glyceride product obtained after the reaction has an iodine value of 24.8. ?0091 ? Comparative example 2 ?0092 ? 30kg palmitic acid stearin was weighed out and placed into a 100L pilot reactor, 5kg sodium palmitate was added, heated and stirred while nitrogen gas introduced. The reaction temperature was kept at 185° C, and the stirring speed was 400 r/min. The reaction was stirred for 20 hours. Then the reaction system was cooled down to 50 ?. N-hexane was added to dissolve solid, and water was added to adsorb soap, then the mixture was filtered. The soap in the organic phase was removed by silica gel adsorption. Light yellow solid was obtained by concentration process. The palmitic acid content at the sn-2 position is 64.2%. ?0093 ? Wherein, the palm oil stearin used for the reaction has an iodine value of 35, and the glyceride product obtained after the reaction has an iodine value of 23.2. ?0094 ? Comparative example 3 ?0095 ? Palmitic acid was weighed out according to the amount of palmitic acid residues of palm oil to keep the ratio of palmitic acid residues to the total fatty acid residues in the reaction system was 96%. 1000g palm oil stearin and 1500ml n-hexane were placed into four-necked flask with heating in a water bath until the palm oil stearin dissolved, and then mixed with the palmitic acid. Then, after nitrogen gas was introduced, the temperature of the water bath was 40° C, and the stirring speed was 380 r/min. After stirring until uniform, 10g of non-specific lipase Lipase DF "Amano" 15 was added, and the reaction was stirred for 1.5 hours with heat preservation. The supernatant of the organic phase was obtained by centrifugation, the soap in the organic phase was removed by silica gel adsorption, and free fatty acids were removed by molecular distillation to obtain a light yellow solid. The palmitic acid content at the sn-2 position is 78%. ?0096 ? Wherein, the palm oil used for the reaction has an iodine value of 35, and the glyceride product obtained after the reaction has an iodine value of 17. ?0097 ? According to Example 1 to Example 10, it can be proved that the purity of the trisaturated fatty acid glycerides prepared by the embodiments of the present disclosure is all over 80% with mild reaction conditions and few side reactions. Through the comparison of Example 5 and Example 11, the addition amount of saturated fatty acid has a greater impact on the purity of the obtained trisaturated fatty acid glycerides. When the addition amount makes the ratio of saturated fatty acid residues to the total fatty acid residues in the reaction system was 90%, products with higher purity can be obtained. By comparing Example 3 and Example 12, adding a solvent into the reaction system is beneficial to the effect of catalyzing the reaction and improving the purity of the product. According to the comparison between Example 5 and Example 13, the non-specific lipase has a better catalytic effect than the specific lipase in the method of the embodiments of the present disclosure. By comparing Example 5 with Examples 14 and 15, it is not that the more lipase is added, the lower the iodine value of the products is. By comparing Example 5 with Example 16 and Example 17, the catalytic reaction effect will be significantly worsened if the temperature is too high or too low. According to Examples 1-10 with Comparative Examples 1-3, compared with the production of trisaturated fatty acid glycerides only under the chemical catalysis of fatty acid salts or the action of lipase, the method in the embodiments of the present disclosure has milder reaction conditions, few side reactions, and greatly improved purity. ?0098 ? In summary, on the basis of saturated fatty acid residues contained in the glyceride, a sufficient amount of saturated fatty acid residues are provided by the saturated fatty acid salt in-situ formed by the corresponding saturated fatty acid and the alkali with catalysis of the lipase to achieve mild reaction conditions, few side reactions, and low iodine value of the resulting glyceride. ?0099 ? The embodiments described above are part of the embodiments of the present disclosure, rather than all of the embodiments. The detailed description of the embodiments of the disclosure is not intended to limit the scope of the claims, but merely represents selected embodiments of the disclosure. Based on the embodiments of the present disclosure, all other embodiments obtained by those of ordinary skill in the art without creative work shall fall within the protection scope of the present disclosure.
Claims (18)
1. A method for lowering an iodine value of a glyceride, comprising: enabling a glyceride, a saturated fatty acid, and an alkali to undergo a catalytic reaction under action of a lipase.
2. The method for lowering the iodine value of the glyceride as claimed in claim 1, wherein a ratio of saturated fatty acid residues to total fatty acid residues in a reaction system of the glyceride and the saturated fatty acid is greater than or equal to 90%.
3. The method for lowering the iodine value of the glyceride as claimed in claim 1, wherein an addition amount of the lipase ranges from 0.05 to 10% of the glyceride.
4. The method for lowering the iodine value of the glyceride as claimed in claim 1, wherein the lipase is a non-specific lipase.
5. The method for lowering the iodine value of the glyceride as claimed in claim 1, wherein temperature of the catalytic reaction ranges from 30 to 90°C, and time of the catalytic reaction ranges from 0.5 to 9 hours.
6. The method for lowering the iodine value of the glyceride as claimed in claim 1, wherein the glyceride is a glyceride containing a saturated fatty acid residue.
7. The method for lowering the iodine value of the glyceride as claimed in claim 1, wherein the iodine value of the glyceride is greater than 20.
8. The method for lowering the iodine value of the glyceride as claimed in claim 1, wherein at least a saturated fatty acid corresponding to saturated fatty acid residues contained in the glyceride is equivalent to the saturated fatty acid.
9. The method for lowering the iodine value of the glyceride as claimed in claim 1, wherein the glyceride is at least one of monoglyceride, diglyceride and triglyceride.
10. The method for lowering the iodine value of the glyceride as claimed in claim 1, wherein the saturated fatty acid is selected from at least one of palmitic acid, stearic acid, caprylic acid, capric acid, lauric acid, myristic acid and arachidic acid.
11. The method for lowering the iodine value of the glyceride as claimed in claim 1, wherein a molar ratio of the alkali to the saturated fatty acid is not greater than
12. The method for lowering the iodine value of the glyceride as claimed in claim 1, wherein enabling undergoing the catalytic reaction comprises steps of mixing the glyceride with the saturated fatty acid and the alkali, adding the lipase, and stirring under a condition of introducing inert gas.
13. The method for lowering the iodine value of the glyceride as claimed in claim 1, wherein the reaction system further comprises a solvent.
14. The method for lowering the iodine value of the glyceride as claimed in claim 13, wherein the solvent is n-hexane.
15. The method for lowering the iodine value of the glyceride as claimed in claim 1, wherein a ratio of saturated fatty acid residues to total fatty acid residues in a reaction system of the glyceride and the saturated fatty acid is greater than 92%.
16. The method for lowering the iodine value of the glyceride as claimed in claim 1, wherein a ratio of saturated fatty acid residues to total fatty acid residues in a reaction system of the glyceride and the saturated fatty acid is greater than 95%.
17. The method for lowering the iodine value of the glyceride as claimed in claim 1, wherein an addition amount of the lipase ranges from 0.1 to 8% of the glyceride.
18. The method for lowering the iodine value of the glyceride as claimed in claim 1, wherein temperature of the catalytic reaction ranges from 35 to 85°C, and the time of catalytic reaction ranges from 1 to 4 hours.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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CN201810725859.7A CN108865445B (en) | 2018-07-04 | 2018-07-04 | Method for reducing iodine value of glyceride |
PCT/CN2019/094644 WO2020007335A1 (en) | 2018-07-04 | 2019-07-04 | Method for lowering iodine value of glyceride |
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Publication Number | Publication Date |
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NZ772540A NZ772540A (en) | 2023-10-27 |
NZ772540B2 true NZ772540B2 (en) | 2024-01-30 |
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