CN112538505B - Technology for enzymatic transesterification - Google Patents
Technology for enzymatic transesterification Download PDFInfo
- Publication number
- CN112538505B CN112538505B CN202011446104.7A CN202011446104A CN112538505B CN 112538505 B CN112538505 B CN 112538505B CN 202011446104 A CN202011446104 A CN 202011446104A CN 112538505 B CN112538505 B CN 112538505B
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- CN
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- Prior art keywords
- triglyceride
- reaction
- oil
- lipase
- long
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- 238000005809 transesterification reaction Methods 0.000 title claims abstract description 55
- 230000002255 enzymatic effect Effects 0.000 title claims abstract description 22
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims abstract description 94
- 108090001060 Lipase Proteins 0.000 claims abstract description 47
- 102000004882 Lipase Human genes 0.000 claims abstract description 47
- 239000004367 Lipase Substances 0.000 claims abstract description 43
- 235000019421 lipase Nutrition 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 36
- 102000015925 Proto-oncogene Mas Human genes 0.000 claims abstract description 23
- 108050004181 Proto-oncogene Mas Proteins 0.000 claims abstract description 23
- XMXLVNVGGJBUPF-UHFFFAOYSA-N 2-amino-n,n-diethyl-1,3-benzothiazole-6-carboxamide Chemical compound CCN(CC)C(=O)C1=CC=C2N=C(N)SC2=C1 XMXLVNVGGJBUPF-UHFFFAOYSA-N 0.000 claims abstract description 16
- 230000008569 process Effects 0.000 claims abstract description 14
- 230000009471 action Effects 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 88
- 239000000758 substrate Substances 0.000 claims description 38
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 20
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 claims description 15
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims description 15
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 claims description 14
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 claims description 12
- 239000010495 camellia oil Substances 0.000 claims description 11
- 229940093609 tricaprylin Drugs 0.000 claims description 11
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 claims description 11
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 claims description 10
- 235000019482 Palm oil Nutrition 0.000 claims description 9
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 9
- 239000002540 palm oil Substances 0.000 claims description 9
- 239000004006 olive oil Substances 0.000 claims description 7
- 235000008390 olive oil Nutrition 0.000 claims description 7
- VMPHSYLJUKZBJJ-UHFFFAOYSA-N trilaurin Chemical compound CCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC VMPHSYLJUKZBJJ-UHFFFAOYSA-N 0.000 claims description 6
- 229960001947 tripalmitin Drugs 0.000 claims description 6
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims description 6
- 239000001087 glyceryl triacetate Substances 0.000 claims description 5
- 235000013773 glyceryl triacetate Nutrition 0.000 claims description 5
- 229960002622 triacetin Drugs 0.000 claims description 5
- HBOQXIRUPVQLKX-BBWANDEASA-N 1,2,3-trilinoleoylglycerol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COC(=O)CCCCCCC\C=C/C\C=C/CCCCC HBOQXIRUPVQLKX-BBWANDEASA-N 0.000 claims description 4
- 235000019498 Walnut oil Nutrition 0.000 claims description 4
- 235000005687 corn oil Nutrition 0.000 claims description 4
- 239000002285 corn oil Substances 0.000 claims description 4
- 239000003549 soybean oil Substances 0.000 claims description 4
- 235000012424 soybean oil Nutrition 0.000 claims description 4
- 239000003760 tallow Substances 0.000 claims description 4
- 239000008170 walnut oil Substances 0.000 claims description 4
- 235000015278 beef Nutrition 0.000 claims description 3
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 claims description 3
- 229940093633 tricaprin Drugs 0.000 claims description 3
- YZWRNSARCRTXDS-UHFFFAOYSA-N tripropionin Chemical compound CCC(=O)OCC(OC(=O)CC)COC(=O)CC YZWRNSARCRTXDS-UHFFFAOYSA-N 0.000 claims description 3
- 238000006561 solvent free reaction Methods 0.000 claims 1
- 150000003626 triacylglycerols Chemical class 0.000 abstract description 20
- 150000002148 esters Chemical group 0.000 description 26
- 102000004190 Enzymes Human genes 0.000 description 23
- 108090000790 Enzymes Proteins 0.000 description 23
- 239000003925 fat Substances 0.000 description 15
- 235000019197 fats Nutrition 0.000 description 15
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 15
- 229940117972 triolein Drugs 0.000 description 13
- 108010048733 Lipozyme Proteins 0.000 description 10
- 239000012295 chemical reaction liquid Substances 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical group CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 150000002632 lipids Chemical class 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 150000004667 medium chain fatty acids Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 241000723346 Cinnamomum camphora Species 0.000 description 3
- 150000004668 long chain fatty acids Chemical class 0.000 description 3
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 150000004666 short chain fatty acids Chemical class 0.000 description 3
- 235000021391 short chain fatty acids Nutrition 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 241000187180 Streptomyces sp. Species 0.000 description 2
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000007036 catalytic synthesis reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- HBOQXIRUPVQLKX-UHFFFAOYSA-N linoleic acid triglyceride Natural products CCCCCC=CCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC HBOQXIRUPVQLKX-UHFFFAOYSA-N 0.000 description 2
- 229960004488 linolenic acid Drugs 0.000 description 2
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000003346 palm kernel oil Substances 0.000 description 2
- 235000019865 palm kernel oil Nutrition 0.000 description 2
- 125000005457 triglyceride group Chemical group 0.000 description 2
- YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000021294 Docosapentaenoic acid Nutrition 0.000 description 1
- 101100289989 Drosophila melanogaster alpha-Man-Ia gene Proteins 0.000 description 1
- 101150021286 MAS1 gene Proteins 0.000 description 1
- 241000104952 Xanthophyllum eurhynchum Species 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 1
- 229940090949 docosahexaenoic acid Drugs 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 235000019626 lipase activity Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 210000003240 portal vein Anatomy 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 235000019940 salatrim Nutrition 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 229940081852 trilinolein Drugs 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C12P7/6445—Glycerides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN202011446104.7A CN112538505B (en) | 2020-12-08 | 2020-12-08 | Technology for enzymatic transesterification |
Applications Claiming Priority (1)
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CN202011446104.7A CN112538505B (en) | 2020-12-08 | 2020-12-08 | Technology for enzymatic transesterification |
Publications (2)
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CN112538505A CN112538505A (en) | 2021-03-23 |
CN112538505B true CN112538505B (en) | 2021-10-15 |
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Family Applications (1)
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CN202011446104.7A Active CN112538505B (en) | 2020-12-08 | 2020-12-08 | Technology for enzymatic transesterification |
Country Status (1)
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CN (1) | CN112538505B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113287659A (en) * | 2021-05-09 | 2021-08-24 | 南昌大学 | Functional structural oil and preparation method and application thereof |
CN114521655A (en) * | 2022-01-27 | 2022-05-24 | 华南理工大学 | Intestinal tract probiotic promoter containing medium-long chain triglyceride in almond oil and preparation method and application thereof |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4079516B2 (en) * | 1998-06-19 | 2008-04-23 | サントリー株式会社 | Method for producing triglyceride |
KR20020081632A (en) * | 2001-04-19 | 2002-10-30 | (주)라이브맥스 | Preparation Method for CLA-enriched Structured Lipid and The Same Use |
CN101979625B (en) * | 2010-11-03 | 2013-07-17 | 江南大学 | Method for synthesizing triglyceride with medium/long-chain structure by catalyzing ester exchange through enzyme |
CN105821089A (en) * | 2016-06-12 | 2016-08-03 | 江南大学 | Method for enzymatically synthesizing medium-long chain structure triglyceride |
CN107805647A (en) * | 2017-12-14 | 2018-03-16 | 广州白云山汉方现代药业有限公司 | A kind of method of backbone ester in enzymatic clarification |
CN111909972A (en) * | 2020-07-29 | 2020-11-10 | 华南理工大学 | Method for preparing partial glyceride by enzymatic method for hydrolyzing triglyceride |
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2020
- 2020-12-08 CN CN202011446104.7A patent/CN112538505B/en active Active
Also Published As
Publication number | Publication date |
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CN112538505A (en) | 2021-03-23 |
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Legal Events
Date | Code | Title | Description |
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PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20230829 Address after: 510700 self compiled (1) five story 516 room, No. 1 Rui FA Road, Whampoa District, Guangzhou, Guangdong. Patentee after: Guangzhou Yonghua special medicine nutrition Technology Co.,Ltd. Address before: Five 510000 mountain road, Guangzhou, Guangdong, Tianhe District Patentee before: SOUTH CHINA University OF TECHNOLOGY Patentee before: Guangzhou Yonghua special medicine nutrition Technology Co.,Ltd. |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A technique of enzymatic ester exchange Granted publication date: 20211015 Pledgee: Bank of China Limited Foshan Nanhai Xiqiao Sub-branch Pledgor: Guangzhou Yonghua special medicine nutrition Technology Co.,Ltd. Registration number: Y2024980005359 |