CN114525313B - Method for synthesizing propylene glycol fatty acid monoester by enzymatic method - Google Patents
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- CN114525313B CN114525313B CN202210181840.7A CN202210181840A CN114525313B CN 114525313 B CN114525313 B CN 114525313B CN 202210181840 A CN202210181840 A CN 202210181840A CN 114525313 B CN114525313 B CN 114525313B
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 title claims abstract description 203
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 84
- 239000000194 fatty acid Substances 0.000 title claims abstract description 84
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 84
- -1 propylene glycol fatty acid Chemical class 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims abstract description 25
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 13
- 238000006911 enzymatic reaction Methods 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- 238000005886 esterification reaction Methods 0.000 claims abstract description 26
- 230000005496 eutectics Effects 0.000 claims abstract description 25
- 239000002904 solvent Substances 0.000 claims abstract description 25
- 238000005119 centrifugation Methods 0.000 claims abstract description 16
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 claims abstract description 15
- 235000019743 Choline chloride Nutrition 0.000 claims abstract description 15
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 claims abstract description 15
- 229960003178 choline chloride Drugs 0.000 claims abstract description 15
- 108090001060 Lipase Proteins 0.000 claims abstract description 14
- 239000004367 Lipase Substances 0.000 claims abstract description 14
- 102000004882 Lipase Human genes 0.000 claims abstract description 14
- 235000019421 lipase Nutrition 0.000 claims abstract description 14
- 150000004665 fatty acids Chemical class 0.000 claims description 33
- 108010084311 Novozyme 435 Proteins 0.000 claims description 8
- 108010048733 Lipozyme Proteins 0.000 claims description 7
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 230000002255 enzymatic effect Effects 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 2
- 238000001308 synthesis method Methods 0.000 claims 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 abstract description 13
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 abstract description 13
- 229960003237 betaine Drugs 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 7
- 238000000926 separation method Methods 0.000 abstract description 7
- 229960004063 propylene glycol Drugs 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 4
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 239000004519 grease Substances 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 238000006664 bond formation reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 19
- 235000012424 soybean oil Nutrition 0.000 description 16
- 239000003549 soybean oil Substances 0.000 description 16
- 230000032050 esterification Effects 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 8
- 238000004811 liquid chromatography Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- YWBLIYFXWVRDAA-KTKRTIGZSA-N 3-hydroxypropyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCO YWBLIYFXWVRDAA-KTKRTIGZSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 240000001548 Camellia japonica Species 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000007036 catalytic synthesis reaction Methods 0.000 description 2
- 235000018597 common camellia Nutrition 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 235000019626 lipase activity Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000014594 pastries Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Abstract
The invention discloses a method for synthesizing propylene glycol fatty acid monoester by an enzymatic method, and belongs to the technical field of grease processing. When the lipase is adopted to catalyze and esterify in the eutectic solvent composed of choline chloride or betaine and propylene glycol to prepare propylene glycol fatty acid monoester, the reaction interface is enlarged and the interfacial tension is reduced due to the introduction of the choline chloride or betaine, and the water generated in the reaction process can be captured by the eutectic solvent through hydrogen bond formation, so that the esterification reaction rate is greatly improved, and the propylene glycol fatty acid monoester content in the product is obviously improved; and moreover, after the reaction is finished, separation of propylene glycol fatty acid monoester and the eutectic solvent can be realized through centrifugation, and the product separation is simple and has good effect. The method has the advantages of high reaction rate, high yield of propylene glycol fatty acid monoester, simple product separation, good effect, environmental protection and good economic and ecological benefits and industrial application prospects.
Description
Technical Field
The invention belongs to the technical field of grease processing, and particularly relates to a method for synthesizing propylene glycol fatty acid monoester by an enzymatic method.
Background
Propylene glycol fatty acid monoester (Propylene glyco FATTY ACID monoester) is one of six commonly used emulsifiers in the food industry, is an approved food additive for use by the U.S. Food and Drug Administration (FDA), has good emulsifying properties and foamability, and is widely used in bread, pastry, margarine and ice cream. In the actual food production process, propylene glycol fatty acid monoester is often compounded with monoglyceride to improve the emulsification effect.
At present, chemical methods such as a direct esterification method, a propylene oxide method, an alcoholysis method and the like are industrially used for synthesizing propylene glycol fatty acid monoester. The food-grade propylene glycol fatty acid monoester is usually prepared by adopting a direct esterification method, acid or alkali is used as a catalyst, propylene glycol and fatty acid are catalyzed to carry out esterification reaction at a high temperature of 120-200 ℃, in order to improve the esterification efficiency, organic solvents such as hexane, toluene and the like are usually added into a reaction system to serve as a water carrying agent or react under a vacuum condition, so that water generated by esterification is distilled out, and the reaction is promoted to be carried out in the direction of generating the propylene glycol fatty acid ester. Because of the non-selectivity of the chemical catalyst, the esterification product contains propylene glycol fatty acid monoester and propylene glycol fatty acid diester, and the yield of the propylene glycol fatty acid monoester is generally lower than 70%; in addition, the chemical esterification method has the problems of high energy consumption, large pollution, deep color of products, easy oxidation and isomerization of unsaturated fatty acid and the like in the process of synthesizing propylene glycol fatty acid monoester. Compared with the traditional chemical method, the enzymatic synthesis of the propylene glycol fatty acid monoester has the advantages of mild reaction conditions, strong specificity, high efficiency, safety, environmental protection and the like, and is a main development direction of the propylene glycol fatty acid monoester synthesis. Liu Zhuang et al (Lipase AOL catalytic synthesis of high-purity camellia seed oil propylene glycol monoester, chinese grease, 2021) adopts Lipase AOL catalytic propylene glycol and camellia seed oil fatty acid ester to synthesize propylene glycol fatty acid monoester, and after reaction for 12 hours at 35 ℃, the content of the propylene glycol fatty acid monoester in the product reaches 85.55%; li Xingxing (study of immobilization of lipase SMG1-F278N and catalytic synthesis of propylene glycol oleic monoester, university of North China university 2017) adopts immobilized partial glyceride lipase SMG1-F278N to catalyze esterification of propylene glycol and oleic acid to prepare propylene glycol oleic monoester, and after reaction is carried out for 12 hours at 30 ℃, the content of propylene glycol fatty acid monoester in the product reaches 70%; to improve the intersolubility of propylene glycol and fatty acid, zhang Kai (enzymatic synthesis, separation and purification and property research of 1, 3-propylene glycol monooleate, university of south China's technology, 2011) is used for catalyzing esterification of 1, 3-propylene glycol and oleic acid to synthesize 1, 3-propylene glycol monooleate by using Novozym 435 as a catalyst in a tertiary butanol system, and after reacting for 7 hours at 50 ℃, the content of propylene glycol fatty acid monoester in the product reaches 88.34 percent. In a word, the content of propylene glycol fatty acid monoester in the product is generally lower than 90% when the propylene glycol fatty acid monoester is synthesized by the enzyme method at present, and the reaction time is longer.
Disclosure of Invention
In order to solve the defects in the prior art, the invention aims to provide the method for synthesizing the propylene glycol fatty acid monoester by an enzyme method, which greatly increases and stabilizes an esterification reaction interface, effectively removes water generated in the esterification reaction process, remarkably improves the esterification reaction rate, greatly shortens the reaction time, and ensures that the content of the propylene glycol fatty acid monoester in the product reaches more than 95 percent.
The invention is realized by the following technical scheme:
A method for synthesizing propylene glycol fatty acid monoester by an enzymatic method comprises the following steps:
Step 1: in a eutectic solvent composed of choline chloride or betaine and propylene glycol, catalyzing liquid fatty acid by adopting immobilized lipase at a preset rotating speed for esterification reaction;
Step 2: and after the reaction is finished, carrying out centrifugal treatment to obtain an upper oil phase product containing propylene glycol fatty acid monoester.
Preferably, in step 1, the molar ratio of choline chloride or betaine to propylene glycol is 1:1 to 3.
Preferably, in step1, the molar ratio of propylene glycol to liquid fatty acid is 3 to 7:1.
Preferably, in step 1, the immobilized lipase is Novozym 435 or Lipozyme 435.
Further preferably, the amount of immobilized lipase added is 1% to 5% of the total mass of the substrate.
Preferably, in step 1, the temperature of the esterification reaction is 40 to 70 ℃.
Preferably, in step 1, the time of the esterification reaction is 1 to 3 hours.
Preferably, in step 1, the preset rotation speed is 200-400 rpm.
Preferably, in the step2, the rotational speed of centrifugation is 8000-12000 rpm, and the time of centrifugation is 1-2 min.
Compared with the prior art, the invention has the following beneficial technical effects:
The method for synthesizing propylene glycol fatty acid monoester by using the enzymatic method disclosed by the invention is carried out in a eutectic solvent composed of choline chloride or betaine and propylene glycol, and the reaction interface is increased and the interface tension is decreased when lipase catalyzes the esterification reaction due to the introduction of choline chloride or betaine; in addition, moisture generated during the esterification reaction can be captured by the formation of hydrogen bonds by the eutectic solvent composed of choline chloride or betaine and propylene glycol; under the combined action of the two points, when lipase is catalyzed and esterified in a eutectic solvent consisting of choline chloride or betaine and propylene glycol to synthesize propylene glycol fatty acid monoester, the reaction rate is greatly improved, and the content of the propylene glycol fatty acid monoester in the product is obviously improved; and moreover, after the reaction is finished, the separation of the propylene glycol fatty acid monoester and the eutectic solvent can be realized through centrifugation, and the separation is simple and has good effect. Compared with the method for synthesizing the propylene glycol fatty acid monoester by catalytic esterification in a solvent-free or organic solvent, the method has the advantages of high reaction rate, high yield of the propylene glycol fatty acid monoester, simple product separation, good effect, environmental protection and good economic and ecological benefits and industrial application prospects.
Further, the molar ratio of choline chloride or betaine to propylene glycol is 1:1 to 3, which is favorable for the formation of larger and more stable reaction interfaces during the enzymatic esterification reaction.
Further, the molar ratio of the propylene glycol to the liquid fatty acid is 3-7: 1, a higher esterification reaction rate and propylene glycol fatty acid monoester yield can be ensured.
Further, the immobilized lipase using Novozym 435 or Lipozyme 435 can ensure high fatty acid selectivity and esterification activity.
Further, the esterification reaction temperature is 40-70 ℃, so that higher lipase activity and stability can be ensured.
Further, the rotational speed of centrifugation is 8000-12000 rpm, and the time of centrifugation is 1-2 min, so that the product can be recovered rapidly and with high recovery rate.
Detailed Description
The invention will now be described in further detail with reference to specific examples, which are intended to illustrate, but not to limit, the invention. All percentages are mass percentages, unless otherwise indicated.
Example 1
Into a 5L reaction flask was charged a mixture of 2Kg of a eutectic solvent consisting of choline chloride and propylene glycol in a molar ratio of 1:1, wherein the fatty acid is soybean oil fatty acid, and the molar ratio of the propylene glycol to the soybean oil fatty acid in the eutectic solvent is 3:1, after preheating the reaction mixture to 40℃20g of Novozym 435 were added and the reaction was carried out with stirring at 200 rpm. After 3 hours of reaction, the reaction product is obtained by centrifugation for 1min at 12000 rpm. The content of propylene glycol fatty acid monoester in the product was analyzed by liquid chromatography and found to be 96.01%.
Example 2
Into a 5L reaction flask was charged a mixture of 2Kg of a eutectic solvent consisting of choline chloride and propylene glycol in a molar ratio of 1:3, the fatty acid is soybean oil fatty acid, and the molar ratio of the propylene glycol to the soybean oil fatty acid in the eutectic solvent is 7:1 after preheating the reaction mixture to 50℃40g of Lipozyme 435 were added and the reaction was carried out with stirring at 400 rpm. After 1h of reaction, the reaction product is obtained by centrifugation for 2min at 8000 rpm. The content of propylene glycol fatty acid monoester in the product was analyzed by liquid chromatography and found to be 97.22%.
Example 3
Into a 5L reaction flask was charged a mixture of 2Kg of a eutectic solvent consisting of choline chloride and propylene glycol in a molar ratio of 1:2, the fatty acid is soybean oil fatty acid, and the molar ratio of the propylene glycol to the soybean oil fatty acid in the eutectic solvent is 5:1 after preheating the reaction mixture to 70℃100g of Novozym 435 were added and the reaction was carried out with stirring at 300 rpm. After 1h of reaction, the reaction product is obtained by centrifugation for 1.5min at 10000 rpm. The content of propylene glycol fatty acid monoester in the product was analyzed by liquid chromatography and found to be 97.46%.
Example 4
Into a 5L reaction flask was charged a mixture of 2Kg of a eutectic solvent consisting of betaine and propylene glycol in a molar ratio of 1:2, the fatty acid is soybean oil fatty acid, and the molar ratio of the propylene glycol to the soybean oil fatty acid in the eutectic solvent is 4:1 after preheating the reaction mixture to 60℃60g of Novozym 435 were added and the reaction was carried out with stirring at 250 rpm. After 1h of reaction, the reaction product is obtained by centrifugation for 1min at 12000 rpm. The content of propylene glycol fatty acid monoester in the product was analyzed by liquid chromatography and found to be 96.39%.
Example 5
Into a 5L reaction flask was charged a mixture of 2Kg of a eutectic solvent consisting of betaine and propylene glycol in a molar ratio of 1:3, the fatty acid is soybean oil fatty acid, and the molar ratio of the propylene glycol to the soybean oil fatty acid in the eutectic solvent is 6:1 after preheating the reaction mixture to 50℃40g of Lipozyme 435 were added and the reaction was carried out at a stirring speed of 300 rpm. After 1h of reaction, the reaction product is obtained by centrifugation for 1min at 12000 rpm. The content of propylene glycol fatty acid monoester in the product was analyzed by liquid chromatography and found to be 96.94%.
Example 6
Into a 5L reaction flask was charged a mixture of 2Kg of a eutectic solvent consisting of betaine and propylene glycol in a molar ratio of 1:1, wherein the fatty acid is soybean oil fatty acid, and the molar ratio of the propylene glycol to the soybean oil fatty acid in the eutectic solvent is 4:1 after preheating the reaction mixture to 50℃60g of Lipozyme 435 were added and the reaction was carried out with stirring at 400 rpm. After 1h of reaction, the reaction product is obtained by centrifugation for 1.5min at 10000 rpm. The content of propylene glycol fatty acid monoester in the product was analyzed by liquid chromatography and found to be 97.88%.
Example 7
Into a 5L reaction flask was charged a mixture of 2Kg of a eutectic solvent consisting of choline chloride and propylene glycol in a molar ratio of 1:1, wherein the fatty acid is soybean oil fatty acid, and the molar ratio of the propylene glycol to the soybean oil fatty acid in the eutectic solvent is 3:1, after preheating the reaction mixture to 45℃50g of Novozym 435 were added and the reaction was carried out at a stirring speed of 300 rpm. After 2h of reaction, the reaction product is obtained by centrifugation for 1.5min at 10000 rpm. The content of propylene glycol fatty acid monoester in the product was analyzed by liquid chromatography and found to be 95.67%.
Example 8
Into a 5L reaction flask was charged a mixture of 2Kg of a eutectic solvent consisting of betaine and propylene glycol in a molar ratio of 1:1, wherein the fatty acid is soybean oil fatty acid, and the molar ratio of the propylene glycol to the soybean oil fatty acid in the eutectic solvent is 4:1, after preheating the reaction mixture to 65℃30g of Lipozyme 435 were added and the reaction was carried out at a stirring speed of 200 rpm. After 3h of reaction, the reaction product is obtained by centrifugation for 1.5min at 10000 rpm. The content of propylene glycol fatty acid monoester in the product was analyzed by liquid chromatography and found to be 96.97%.
Claims (5)
1. The enzymatic synthesis method of propylene glycol fatty acid monoester is characterized by comprising the following steps:
Step 1: in a eutectic solvent composed of choline chloride and propylene glycol, catalyzing liquid fatty acid by adopting immobilized lipase at a preset rotating speed to perform esterification reaction; the molar ratio of choline chloride to propylene glycol is 1: 1-3; the immobilized lipase is Novozym 435 or Lipozyme 435; the addition amount of the immobilized lipase is 1% -5% of the total mass of the substrate; the molar ratio of the propylene glycol to the liquid fatty acid is 3-7: 1, a step of;
Step 2: and after the reaction is finished, carrying out centrifugal treatment to obtain an upper oil phase product containing propylene glycol fatty acid monoester.
2. The method for enzymatic synthesis of propylene glycol fatty acid monoester according to claim 1, wherein in step 1, the esterification reaction temperature is 40-70 ℃.
3. The method for synthesizing propylene glycol fatty acid monoester by an enzymatic method according to claim 1, wherein in the step 1, the esterification reaction time is 1-3 hours.
4. The method for synthesizing propylene glycol fatty acid monoester by an enzymatic method according to claim 1, wherein in step 1, the preset rotation speed is 200-400 rpm.
5. The method for synthesizing propylene glycol fatty acid monoester by an enzymatic method according to claim 1, wherein in the step2, the rotational speed of centrifugation is 8000-12000 rpm, and the time of centrifugation is 1-2 min.
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