CN101182556A - Method of enzymatic synthesis medium-chain diglyceride assisted by microwave-ultrasonic wave - Google Patents
Method of enzymatic synthesis medium-chain diglyceride assisted by microwave-ultrasonic wave Download PDFInfo
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- CN101182556A CN101182556A CNA2007101906066A CN200710190606A CN101182556A CN 101182556 A CN101182556 A CN 101182556A CN A2007101906066 A CNA2007101906066 A CN A2007101906066A CN 200710190606 A CN200710190606 A CN 200710190606A CN 101182556 A CN101182556 A CN 101182556A
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- carbonic acid
- microwave
- reaction
- ultrasonic
- ultrasonic wave
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- 238000000034 method Methods 0.000 title claims abstract description 13
- 230000015572 biosynthetic process Effects 0.000 title abstract description 3
- 230000002255 enzymatic effect Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 102000004190 Enzymes Human genes 0.000 claims abstract description 20
- 108090000790 Enzymes Proteins 0.000 claims abstract description 20
- 102000004882 Lipase Human genes 0.000 claims abstract description 11
- 108090001060 Lipase Proteins 0.000 claims abstract description 11
- 239000004367 Lipase Substances 0.000 claims abstract description 11
- 235000019421 lipase Nutrition 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 28
- 238000006555 catalytic reaction Methods 0.000 claims description 21
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 20
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 18
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 12
- 230000005855 radiation Effects 0.000 claims description 11
- 235000011187 glycerol Nutrition 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 230000009466 transformation Effects 0.000 claims description 7
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 6
- 230000004044 response Effects 0.000 claims description 6
- 238000013019 agitation Methods 0.000 claims description 5
- 239000012153 distilled water Substances 0.000 claims description 5
- 239000011521 glass Substances 0.000 claims description 5
- 238000002479 acid--base titration Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000005070 sampling Methods 0.000 claims description 2
- 238000002604 ultrasonography Methods 0.000 claims description 2
- 238000005516 engineering process Methods 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
- 230000035484 reaction time Effects 0.000 abstract description 2
- 230000002079 cooperative effect Effects 0.000 abstract 2
- 239000006227 byproduct Substances 0.000 abstract 1
- 238000012216 screening Methods 0.000 description 6
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 4
- 230000002153 concerted effect Effects 0.000 description 4
- 238000004891 communication Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 3
- 238000010586 diagram Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000036632 reaction speed Effects 0.000 description 2
- 241000321538 Candidia Species 0.000 description 1
- 208000004930 Fatty Liver Diseases 0.000 description 1
- 206010019708 Hepatic steatosis Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 208000010706 fatty liver disease Diseases 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 231100000240 steatosis hepatitis Toxicity 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A method for using the micro-wave-ultrasonic wave to support enzyme to catalyze and synthesize medium-carbonic acid diglyceride belongs to the organic compound biosynthesis technology field. The invention adopts the cooperative action of the micro-wave-ultrasonic wave to catalyze and synthesize the medium-carbonic acid diglyceride with lipase; and with the cooperative action of heating by microwave and the ration of ultrasonic wave in a cooperative reaction device of the microwave-ultrasonic wave, medium-carbonic acid and diglyceride are taken as the raw materials to catalyze and synthesize the diglyceride with the lipase as the catalyst. The method of the invention can accelerate the reaction and promote the productivity of diglyceride; moreover, with the method, the reaction time can be greatly shortened and the by product is reduced.
Description
Technical field
A kind of method with the synthetic middle carbonic acid triglyceride of microwave-ultrasonic auxiliary enzymes catalysis includes organic compounds biosynthesis technology field.Specifically a kind of method of utilizing the microwave-ultrasonic concerted reaction to carry out lipase-catalyzed esterification is a raw material with middle carbonic acid and glycerine, and heated by microwave, ultrasonic wave radiation acting in conjunction are the synthetic middle carbonic acid triglyceride of catalyst with lipase.
Background technology
The triglyceride (comprising 1,3-triglyceride and 1,2-triglyceride) of middle carbonic acid such as sad or capric acid is the crucial compound of a class, is widely used in industrial circles such as chemical industry, food, daily use chemicals, medicine.As the fat-reducing medicament that the capric acid triglyceride can be used as effectively, has no side effect, can be used for prevention and treatment fatty liver.
Carbonic acid triglyceride during traditional chemical catalysis is synthetic need carry out under high temperature, high pressure and strong acid, alkali condition usually, and side reaction is many, the product separation difficulty, and the production cost height works the mischief to environment again simultaneously.The enzyme catalysis building-up process is carried out usually at normal temperatures and pressures, has reaction conditions gentleness, strong, the catalytic efficiency advantages of higher of catalysis specificity, is typical friendly process.Microwave technology is reacted stereoselective superiority and has been obtained developing rapidly with its energy fast reaction speed, raising reaction yield, change.Suitably the ultrasonic wave of intensity equally can fast reaction speed, improves reaction yield.
Provided by the present invention synthetic in the technology of carbonic acid triglyceride with microwave heating, ultrasonic radiation and enzyme catalysis is effective combines, many characteristics of comprehensive utilization microwave catalysis, ultrasonic wave catalysis and enzymic catalytic reaction, thus provide a kind of efficient, fast, meet the synthetic method of Green Chemistry and environmental friendliness developing direction.The reaction equation of carbonic acid triglyceride is as follows in synthetic:
1-monoglyceride 2-monoglyceride 1,3-triglyceride 1,2-triglyceride triglyceride level wherein, n=7 or 9.
Summary of the invention
The purpose of this invention is to provide a kind of method, carbonic acid triglyceride during application the present invention can synthesize efficiently, apace with the synthetic middle carbonic acid triglyceride of microwave-ultrasonic auxiliary enzymes catalysis.
Purpose of the present invention can reach by the following technical solutions: with glycerine and middle carbonic acid is raw material, the batching mol ratio of glycerine and middle carbonic acid is 1: 2～3, glycerine and middle carbonic acid and distilled water are placed glass reactor, amount of water accounts for 1%～5% of reaction system total mass, after making it to mix with magnetic agitation, move in the microwave-ultrasonic reaction unit, start the microwave-ultrasonic radiation, microwave power is 100～1000W, the ultrasonic wave radiation frequency is 40KHz, and power is 50W, adds lipase when the question response system temperature rises to temperature of reaction and picks up counting, enzyme concentration is a carbonic acid among 2～16g/mol, remove the moisture that generates in the reaction process by vacuum, sampling is with the transformation efficiency of carbonic acid in the determination of acid-basetitration, 30～70 ℃ of reactions to middle carbonic acid transformation efficiency greater than after 99%, stop radiation, shift out product.
Said auxiliary enzymes catalysis synthesizes uses microwave and ultrasound wave auxiliary enzyme catalysis to synthesize simultaneously.
Carbonic acid is sad in said, capric acid or both mixtures.
Beneficial effect of the present invention: the carbonic acid triglyceride needed the reaction times of 6-24hr usually during the enzyme catalysis under the conventional heating was synthetic, and the catalysis of microwave-ultrasonic auxiliary enzymes is synthetic can to improve speed of response and make reaction conditions gentle more and use simultaneously.
Description of drawings
Fig. 1 microwave-assisted enzyme catalyst reaction device synoptic diagram.
Wherein: 1, micro-wave screening cavity, 2, magnetron, 3, reaction vessel, 4, chuck, 5, magnetic stirring apparatus, 6, micro-wave screening heat-eliminating medium accessing port, 7, micro-wave screening heat-eliminating medium outgoing interface, 8, micro-wave screening cavity top micro-wave screening interface, 9, the micro-wave screening temperature sensor, 10, stopple coupon, 11, gas introduction tube, 12, Temperature Feedback control unit, 13, load, 14, ultrasonic generator.
Embodiment
Below the present invention is carried out the description of embodiment, microwave-ultrasonic reaction unit synoptic diagram is referring to Fig. 1.
Sunfat GDC-S is synthesized in embodiment 1 microwave-ultrasonic auxiliary enzymes catalysis
70g is sad, 20g glycerine and 2g distilled water place glass reactor, make it to mix with magnetic agitation.Then above-mentioned reactor is moved in the microwave-ultrasonic concerted reaction device of communication loop water vacuum pump.Microwave power is 1000W, and the ultrasonic wave radiation frequency is 40KHz, and power is 50W.When the question response system temperature rises to 65 ℃, add 5g lipase Nov0435B (antarctic candidia lipase).Sad transformation efficiency is 99% behind the reaction 1.5h, and triglyceride level, triglyceride and monoglyceride molar content are respectively 7%, 61% and 32%.
The capric acid triglyceride is synthesized in embodiment 2 microwave-ultrasonic auxiliary enzymes catalysis
100g capric acid, 20g glycerine and 3g distilled water are placed glass reactor, make it to mix with magnetic agitation.Then above-mentioned reactor is moved in the microwave-ultrasonic concerted reaction device of communication loop water vacuum pump.Microwave power is 700W, and the ultrasonic wave radiation frequency is 40KHz, and power is 50W.When the question response system temperature rises to 50 ℃, add 7g lipase RMIM (Michaelis miehei lipase).The capric acid transformation efficiency is 99.1% behind the reaction 2.5h, and triglyceride level, triglyceride and monoglyceride molar content are respectively 17%, 65% and 18%.
Hot capric acid triglyceride is synthesized in embodiment 3 microwave-ultrasonic auxiliary enzymes catalysis
(sad: capric acid=51: 49 w/w), 21g glycerine and 4g distilled water places glass reactor, makes it to mix with magnetic agitation with carbonic acid in the 120g industry.Then above-mentioned reactor is moved in the microwave-ultrasonic concerted reaction device of communication loop water vacuum pump.Microwave power is 200W, and the ultrasonic wave radiation frequency is 40KHz, and power is 50W.When the question response system temperature rises to 40 ℃, add 8g lipase RM IM (Michaelis miehei lipase).The carbonic acid transformation efficiency was 99.2% during reaction 5h was postindustrial, and triglyceride level, triglyceride and monoglyceride molar content are respectively 19%, 69% and 12%.To heat only enzyme catalysis synthetic if use routine instead, and this reaction needed 12h just can finish reaction.
Claims (3)
- One kind with the catalysis of microwave-ultrasonic auxiliary enzymes synthetic in the method for carbonic acid triglyceride, it is characterized in that with glycerine and middle carbonic acid be raw material, the batching mol ratio of glycerine and middle carbonic acid is 1: 2～3, glycerine and middle carbonic acid and distilled water are placed glass reactor, amount of water accounts for 1%～5% of reaction system total mass, after making it to mix with magnetic agitation, move in the microwave-ultrasonic reaction unit, start the microwave-ultrasonic radiation, microwave power is 100～1000W, the ultrasonic wave radiation frequency is 40KHz, power is 50W, add lipase when the question response system temperature rises to temperature of reaction and pick up counting, enzyme concentration is a carbonic acid among 2～16g/mol, removes the moisture that generates in the reaction process by vacuum, the sampling transformation efficiency of carbonic acid in the determination of acid-basetitration, 30～70 ℃ of reactions to middle carbonic acid transformation efficiency greater than after 99%, stop radiation, shift out product.
- 2. method according to claim 1 is characterized in that said auxiliary enzymes catalysis synthesizes to use microwave and ultrasound wave auxiliary enzyme catalysis synthetic simultaneously.
- 3. method according to claim 1 is characterized in that said middle carbonic acid is sad, capric acid or both mixtures.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2007101906066A CN101182556B (en) | 2007-11-27 | 2007-11-27 | Method of enzymatic synthesis of medium-chain diglyceride assisted by microwave-ultrasonic wave |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2007101906066A CN101182556B (en) | 2007-11-27 | 2007-11-27 | Method of enzymatic synthesis of medium-chain diglyceride assisted by microwave-ultrasonic wave |
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| Publication Number | Publication Date |
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| CN101182556A true CN101182556A (en) | 2008-05-21 |
| CN101182556B CN101182556B (en) | 2010-09-29 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102085472A (en) * | 2010-12-16 | 2011-06-08 | 中国科学院高能物理研究所 | Reduced pressure distillation ultrasonic reactor |
| CN102649974A (en) * | 2012-05-14 | 2012-08-29 | 上海海洋大学 | Method for preparing antioxidant peptide through ultrasonic-microwave synergetic enzymatic hydrolysis |
| CN106148439A (en) * | 2016-09-08 | 2016-11-23 | 东北农业大学 | A kind of method that power ultrasonic pretreatment enzyme law catalysis Adeps Sus domestica glycerol rhizolomy prepares diglyceride |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1428430A (en) * | 2001-12-28 | 2003-07-09 | 中国人民解放军总装备部后勤部军事医学研究所 | Enzyme ultrasonic wave combined catalytic synthesis method |
| CN1995364B (en) * | 2006-12-19 | 2010-12-01 | 江南大学 | Microwave-assisted method for enzyme catalytic synthesis for polyol ester |
-
2007
- 2007-11-27 CN CN2007101906066A patent/CN101182556B/en not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102085472A (en) * | 2010-12-16 | 2011-06-08 | 中国科学院高能物理研究所 | Reduced pressure distillation ultrasonic reactor |
| CN102085472B (en) * | 2010-12-16 | 2013-02-13 | 中国科学院高能物理研究所 | Reduced pressure distillation ultrasonic reactor |
| CN102649974A (en) * | 2012-05-14 | 2012-08-29 | 上海海洋大学 | Method for preparing antioxidant peptide through ultrasonic-microwave synergetic enzymatic hydrolysis |
| CN102649974B (en) * | 2012-05-14 | 2014-03-19 | 上海海洋大学 | Method for preparing antioxidant peptide through ultrasonic-microwave synergetic enzymatic hydrolysis |
| CN106148439A (en) * | 2016-09-08 | 2016-11-23 | 东北农业大学 | A kind of method that power ultrasonic pretreatment enzyme law catalysis Adeps Sus domestica glycerol rhizolomy prepares diglyceride |
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| CN101182556B (en) | 2010-09-29 |
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Address after: 214014 Jiangsu province Wuxi chonganou mount a horse Pier Road No. 18 Chong Chong'an District Service Center Patentee after: Jiangnan University Address before: 1800 No. 214122 Jiangsu city of Wuxi Province Li Lake Avenue Patentee before: Jiangnan University |
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Effective date of registration: 20161025 Address after: 200131 Chinese (Shanghai) free trade zone 500 Foot Road No. three room 330 Patentee after: Shanghai Rui Ning Biological Technology Co., Ltd. Address before: 214014 Jiangsu province Wuxi chonganou mount a horse Pier Road No. 18 Chong Chong'an District Service Center Patentee before: Jiangnan University |
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