CN100376541C - Preparation process of diglyceride - Google Patents
Preparation process of diglyceride Download PDFInfo
- Publication number
- CN100376541C CN100376541C CNB2004100153484A CN200410015348A CN100376541C CN 100376541 C CN100376541 C CN 100376541C CN B2004100153484 A CNB2004100153484 A CN B2004100153484A CN 200410015348 A CN200410015348 A CN 200410015348A CN 100376541 C CN100376541 C CN 100376541C
- Authority
- CN
- China
- Prior art keywords
- reaction
- lipid acid
- triglyceride
- lipase
- glycerine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 83
- 235000011187 glycerol Nutrition 0.000 claims abstract description 40
- 108090001060 Lipase Proteins 0.000 claims abstract description 38
- 102000004882 Lipase Human genes 0.000 claims abstract description 38
- 239000004367 Lipase Substances 0.000 claims abstract description 33
- 235000019421 lipase Nutrition 0.000 claims abstract description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000000741 silica gel Substances 0.000 claims abstract description 30
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 30
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000002252 acyl group Chemical group 0.000 claims abstract description 12
- 239000006227 byproduct Substances 0.000 claims abstract description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 40
- 239000002253 acid Substances 0.000 claims description 39
- 150000002632 lipids Chemical class 0.000 claims description 39
- 108090000790 Enzymes Proteins 0.000 claims description 36
- 102000004190 Enzymes Human genes 0.000 claims description 36
- 239000000047 product Substances 0.000 claims description 20
- 239000000376 reactant Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- 239000012052 hydrophilic carrier Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 150000003626 triacylglycerols Chemical class 0.000 claims description 4
- 108010093096 Immobilized Enzymes Proteins 0.000 claims description 3
- 125000005313 fatty acid group Chemical group 0.000 claims description 3
- 241000228212 Aspergillus Species 0.000 claims description 2
- 241000894006 Bacteria Species 0.000 claims description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 230000000813 microbial effect Effects 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 108010079522 solysime Proteins 0.000 claims description 2
- 238000010189 synthetic method Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 22
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 8
- 239000000194 fatty acid Substances 0.000 abstract description 8
- 229930195729 fatty acid Natural products 0.000 abstract description 8
- 238000006555 catalytic reaction Methods 0.000 abstract description 7
- 230000018044 dehydration Effects 0.000 abstract description 5
- 238000006297 dehydration reaction Methods 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 5
- 150000004665 fatty acids Chemical class 0.000 abstract description 3
- 238000000926 separation method Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract 2
- 238000013019 agitation Methods 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 230000002255 enzymatic effect Effects 0.000 abstract 1
- 238000000199 molecular distillation Methods 0.000 description 11
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 9
- 108010048733 Lipozyme Proteins 0.000 description 8
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 4
- 239000004519 grease Substances 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 208000005156 Dehydration Diseases 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 125000005908 glyceryl ester group Chemical group 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019626 lipase activity Nutrition 0.000 description 1
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 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
- 239000011148 porous material Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Images
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
Abstract
Description
Oleic acid (g) | Glycerine (g) | Silica gel (g) | Enzyme (g) | Temperature of reaction (℃) | Reaction times (hr) | |
Embodiment 1 | 450 | 100 | 60 | 30 | 40 | 8 |
|
450 | 48 | 4.8 | 2.5 | 40 | 24 |
|
450 | 147 | 118 | 30 | 40 | 8 |
Embodiment 4 | 450 | 100 | 125 | 10 | 20 | 24 |
|
450 | 100 | 100 | 30 | 80 | 8 |
Embodiment 6 | 450 | 80 | 24 | 30 | 55 | 8 |
Oleic acid (%) | Mono-glycerides (%) | Triglyceride (%) | Triglyceride level (%) | ||
Embodiment 1 | Reaction product | 13.1 | 14.5 | 64.3 | 8.1 |
The molecular distillation product | 0.1 | 0.3 | 88.3 | 11.3 | |
|
Reaction product | 38.9 | 8.6 | 37.3 | 15.2 |
The molecular distillation product | 0.1 | 0.2 | 71.7 | 28.0 | |
|
Reaction product | 16.6 | 15.8 | 58.5 | 9.1 |
The molecular distillation product | 0.1 | 0.3 | 86.0 | 13.6 | |
Embodiment 4 | Reaction product | 31.6 | 10.2 | 45.0 | 13.2 |
The molecular distillation product | 0.1 | 0.3 | 76.9 | 22.7 | |
|
Reaction product | 15.1 | 12.5 | 55.3 | 17.1 |
The molecular distillation product | 0.1 | 0.3 | 76.1 | 23.5 | |
Embodiment 6 | Reaction product | 23.6 | 11.2 | 52.6 | 12.6 |
The molecular distillation product | 0.1 | 0.3 | 80.2 | 19.4 |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2004100153484A CN100376541C (en) | 2004-02-16 | 2004-02-16 | Preparation process of diglyceride |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2004100153484A CN100376541C (en) | 2004-02-16 | 2004-02-16 | Preparation process of diglyceride |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1560020A CN1560020A (en) | 2005-01-05 |
CN100376541C true CN100376541C (en) | 2008-03-26 |
Family
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Family Applications (1)
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---|---|---|---|
CNB2004100153484A Expired - Fee Related CN100376541C (en) | 2004-02-16 | 2004-02-16 | Preparation process of diglyceride |
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CN (1) | CN100376541C (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1884564B (en) * | 2006-05-31 | 2010-09-08 | 东莞新宝精化有限公司 | Process for the production of diglyceride using holoenzyme |
CN101260417B (en) * | 2008-04-25 | 2011-05-11 | 清华大学 | Technique for preparing 1,3-diglyceride in petroleum ether medium system by enzyme method |
CN101818176B (en) * | 2010-04-09 | 2013-05-15 | 浙江兴业集团有限公司 | Method for transforming fatty acid ethyl ester into glyceride |
CN103361387B (en) * | 2013-07-25 | 2014-12-03 | 华南理工大学 | Production method for coproducing unsaturated monoglyceride by using diglyceride enzyme method |
CN105087686B (en) * | 2014-04-23 | 2019-10-22 | 丰益(上海)生物技术研发中心有限公司 | Pass through the method for lipase-catalyzed preparation biodiesel |
CN110305015B (en) * | 2019-07-30 | 2022-06-14 | 广州白云山汉方现代药业有限公司 | Separation method of natural partial glyceride |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1267322A (en) * | 1997-08-18 | 2000-09-20 | 花王株式会社 | Process for producing diglycerides |
US6361980B2 (en) * | 1999-12-17 | 2002-03-26 | Kao Corporation | Preparation process of diglyceride |
CN1438308A (en) * | 2003-03-06 | 2003-08-27 | 华南理工大学 | Method for producing diglyceride |
-
2004
- 2004-02-16 CN CNB2004100153484A patent/CN100376541C/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1267322A (en) * | 1997-08-18 | 2000-09-20 | 花王株式会社 | Process for producing diglycerides |
US6361980B2 (en) * | 1999-12-17 | 2002-03-26 | Kao Corporation | Preparation process of diglyceride |
CN1438308A (en) * | 2003-03-06 | 2003-08-27 | 华南理工大学 | Method for producing diglyceride |
Also Published As
Publication number | Publication date |
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CN1560020A (en) | 2005-01-05 |
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Owner name: DONGGUAN XINBAO REFINEMENT CO., LTD. Free format text: FORMER OWNER: SOUTH CHINA UNIVERSITY OF TECHNOLOGY Effective date: 20050624 |
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Effective date of registration: 20050624 Address after: 523000 Guangdong province Dongguan city Changping Town Road Xinbao Industrial Zone Applicant after: Dongguan Xinbao Fine Chemical Co., Ltd. Address before: 510640 No. five, 381 mountain road, Guangzhou, Guangdong, Tianhe District Applicant before: South China University of Technology |
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Effective date of registration: 20150929 Address after: Huang Dongshan 522000 Qishan Avenue in Guangdong province Jieyang city Rongcheng District East Ring Road South City Jinfeng Garden Garden Shop No. 24 Patentee after: Guangdong long run renewable resources Co., Ltd. Address before: 523000 Guangdong province Dongguan city Changping Town Road Xinbao Industrial Zone Patentee before: Dongguan Xinbao Fine Chemical Co., Ltd. |
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CF01 | Termination of patent right due to non-payment of annual fee | ||
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Granted publication date: 20080326 Termination date: 20160216 |