CN101260417B - Technique for preparing 1,3-diglyceride in petroleum ether medium system by enzyme method - Google Patents
Technique for preparing 1,3-diglyceride in petroleum ether medium system by enzyme method Download PDFInfo
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- CN101260417B CN101260417B CN2008101050820A CN200810105082A CN101260417B CN 101260417 B CN101260417 B CN 101260417B CN 2008101050820 A CN2008101050820 A CN 2008101050820A CN 200810105082 A CN200810105082 A CN 200810105082A CN 101260417 B CN101260417 B CN 101260417B
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Abstract
The invention discloses a technology for preparing 1,3-diacylglycerol in a petroleum ether medium system by an enzymatic method, belonging to the diacylglycerol technical field. The steps of the technology are as follows: putting glycerin and fatty donor with a molar ratio of 1:0.5 to 1:3, petroleum ether of 20 to 200 percent of the weight of the fatty acid donor, lipase of 2 to 20 percent of theweight of the fatty acid, and 3 angstrom molecular sieve of 10 to 100 percent of the weight of the free fatty acid together into any biochemical reactor adaptive for enzymatic reaction to be uniformly mixed; the temperature is controlled between 30 and 65 DEG C and the reaction time is 1 to 10 hours. The percent conversion from glycerin to diglyceride can reach 70 to 95 percent. The content of 1,3-diacylglycerol in the diglyceride can reach more than 80 percent. The lipase can be certain single lipase or a combination of lipases with different functions. The technology has the advantages that the viscidity of the reaction system is reduced, the mass transfer effect among substrates is reinforced, and the reaction is effectively promoted, thereby improving the catalytic efficiency of the lipase.
Description
Technical field
The present invention relates to the triglyceride technical field, be particularly related in a kind of sherwood oil medium system enzyme process preparation 1,3-triglyceride technology, with sherwood oil as reaction medium, lipase-catalyzed glycerine carries out esterification High-efficient Production 1, the 3-triglyceride with different lipid acid donors.
Background technology
Triglyceride is a kind of the fat mols with two fatty acid chains, and two kinds of isomerss are arranged, promptly 1, and 2-triglyceride and 1,3-triglyceride.Discovering in recent years, 1, the 3-triglyceride is in the intravital absorption metabolic way of people and triglyceride level and 1, the difference of 2-triglyceride.Triglyceride level and 1,2-triglyceride are through digestive ferment digestion back generation mono-glycerides and free fatty acids, after the two absorption enters blood, and major part synthetic glycerine three esters again very.And 1, the 3-triglyceride generates glycerine and free fatty acids after the digestive ferment effect, and the two changes into energy in vivo.Therefore, eat and contain 1, the grease of 3-triglyceride has the effect that prevents weight increase.Triglyceride also can be used as emulsifying agent, fatty plasticity improving agent or is used as the matrix of food, medicine, makeup etc.
Glycerine esterification method synthetic triglyceride is a method relatively more commonly used, but the glycerine viscosity is big, and wetting ability is strong, and in solvent-free system, glycerine and lipid acid donor mutual solubility in system are poor, and mass transfer effect is bad, and Enzymatic transformation efficient is low; As reaction medium, the lipid acid donor can well be dissolved in the sherwood oil the present invention's proposition with sherwood oil, and the introducing of sherwood oil has reduced the viscosity of reaction system, has strengthened the mass transfer effect between the substrate; And,, to compare as reaction medium with sherwood oil with other reaction medium such as normal hexane, in the triglyceride that reaction generates 1, the content of 3-triglyceride significantly raises.
Summary of the invention
The object of the present invention is to provide in a kind of sherwood oil medium system enzyme process preparation 1,3-triglyceride technology is to adopt sherwood oil as reaction medium, makes in the triglyceride that reaction generates 1, and the content of 3-triglyceride significantly raises.
The present invention proposes to prepare as reaction medium with sherwood oil the method for triglyceride.Processing step is: the glycerine and the lipid acid donor that with mol ratio are 1: 0.5～1: 3, sherwood oil based on lipid acid donor quality 20～200%, based on the lipase of lipid acid donor quality 2～20%, based on free lipid acid quality 10%-100%'s in the lipid acid donor
Molecular sieve mixes in any biochemical reactor that is suitable for enzyme reaction of packing into together, and temperature is controlled at 30～65 ℃, successive reaction 1～5 hour, glycerine reaches 70～95% to the transformation efficiency of triglyceride, and in the triglyceride of generation 1, the content of 3-triglyceride reaches more than 80%.Lipase can be certain single fat enzyme, also can be the combination of different performance lipase.
Described lipase is biological lipase, comprises the lipase that derives from Candida antarctica, Thermomyceslanuginosus, Rhizomucor miehei or Rhizopus oryza.
Described lipid acid donor is lipid acid, fatty acid short-chain ester or both mixtures.
Described lipid acid is one or more the mixture that has in the lipid acid of 10～22 carbon atoms.
Described fatty acid short-chain ester is one or more the mixture in the methyl esters, ethyl ester, propyl ester, butyl ester, pentyl ester of above-mentioned lipid acid.
The invention has the beneficial effects as follows and adopt sherwood oil, reduced the viscosity of reaction system, strengthened the mass transfer effect between the substrate, promoted the carrying out of reaction effectively, thereby improved the catalytic efficiency of lipase as reaction medium.Especially sherwood oil is as reaction medium, and the method for preparing triglyceride with in the past esterification is compared, and 1, the content of 3-triglyceride significantly raises.
Embodiment
Further specify the present invention below by embodiment.
Embodiment 1
With mol ratio is 1: 1 glycerine and palmitinic acid, based on free fatty acids quality 50%
Molecular sieve, and based on the sherwood oil of palmitinic acid quality 100%, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 50 ℃ after, adding was reacted 2 hours based on the immobilized lipase Novozym 435 (deriving from Candida antarctica) of palmitinic acid quality 5%, and glycerine reaches 95% to the transformation efficiency of triglyceride, wherein 1, the 3-triglyceride accounts for 90%.
Embodiment 2
With mol ratio 1: 0.5 glycerine and fatty acid methyl ester, and based on the sherwood oil of fatty acid methyl ester quality 150%, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 50 ℃ after, adding was reacted 4 hours based on the immobilized lipase Lipozyme TL IM (deriving from Thermomyceslanuginosus) of fatty acid methyl ester quality 6%, and glycerine reaches 90% to the transformation efficiency of triglyceride, wherein 1, the 3-triglyceride accounts for 85%.
Embodiment 3
With mol ratio is 1: 2 glycerine and oleic acid, based on free fatty acids quality 50%
Molecular sieve, and based on the sherwood oil of oleic acid quality 20%, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 60 ℃ after, adding was reacted 4 hours based on the immobilized lipase Lipozyme RM IM (deriving from Rhizomucor miehe) of oleic acid quality 10%, and glycerine reaches 95% to the transformation efficiency of triglyceride, wherein 1, the 3-triglyceride accounts for 90%.
Embodiment 4
With mol ratio 1: 3 glycerine and fatty-acid ethyl ester, and based on the sherwood oil of fatty-acid ethyl ester quality 50%, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 30 ℃ after, adding was reacted 5 hours based on the immobilized lipase Lipozyme TL IM of fatty-acid ethyl ester quality 10%, and glycerine reaches 85% to the transformation efficiency of triglyceride, wherein 1, the 3-triglyceride accounts for 80%.
Embodiment 5
With mol ratio is 1: 3 glycerine and acidifying oil (fatty acids 80%), based on free fatty acids quality 20%
Molecular sieve, and based on the sherwood oil of stearic acid quality 80%, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 65 ℃ after, adding was reacted 3 hours based on the immobilized lipase Novo 435 of stearic acid quality 2%, and glycerine reaches 80% to the transformation efficiency of triglyceride, wherein 1, the 3-triglyceride accounts for 90%.
Embodiment 6
With mol ratio 1: 1 glycerine and fatty acid ester (mixture of fatty-acid ethyl ester and propyl ester), and based on the sherwood oil of lipid acid propyl ester quality 200%, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 40 ℃ after, adding was reacted 1 hour based on the immobilized lipase Lipozyme RMIM of lipid acid propyl ester quality 10%, and glycerine reaches 90% to the transformation efficiency of triglyceride, wherein 1, the 3-triglyceride accounts for 90%.
Embodiment 7
With mol ratio is 1: 1 glycerine and lipid acid (mixture of oleic acid and palmitinic acid), based on free fatty acids quality 50%
Molecular sieve, and based on the sherwood oil of oleic acid quality 100%, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 50 ℃ after, adding was reacted 3 hours based on the immobilized lipase Novo 435 of oleic acid quality 2% and 5% immobilized lipase Lipozyme TL IM, and glycerine reaches 90% to the transformation efficiency of triglyceride, wherein 1, the 3-triglyceride accounts for 85%.
Embodiment 8
With mol ratio 1: 2 glycerine and fatty acid methyl ester, and based on the sherwood oil of fatty acid methyl ester quality 150%, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 55 ℃ after, adding was reacted 3 hours based on the immobilized lipase Novo 435 of fatty acid methyl ester quality 1% and 4% immobilized lipase LipozymeRM IM, and glycerine reaches 95% to the transformation efficiency of triglyceride, wherein 1, the 3-triglyceride accounts for 80%.
Embodiment 9
With mol ratio is 1: 3 glycerine and oleic acid, based on free fatty acids quality 100%
Molecular sieve, and based on the sherwood oil of oleic acid quality 200%, pack into and mix in the tool plug triangular flask, and place can be temperature automatically controlled reciprocal shaking table be heated to 60 ℃ after, adding was reacted 2 hours based on the immobilized lipase Lipozyme TL IM of oleic acid quality 2% and 3% immobilized lipase Lipozyme RM IM, and glycerine reaches 85% to the transformation efficiency of triglyceride, wherein 1, the 3-triglyceride accounts for 90%.
Claims (4)
1. enzyme process preparation 1 in the sherwood oil medium system, 3-triglyceride technology is characterized in that,
Processing step is: the glycerine and the lipid acid donor that with mol ratio are 1: 0.5～1: 3, sherwood oil based on lipid acid donor quality 20～200%, based on the lipase of lipid acid donor quality 2～20%, based on free lipid acid quality 10-100%'s in the lipid acid donor
Molecular sieve mixes in any biochemical reactor that is suitable for enzyme reaction of packing into together, and temperature is controlled at 30～65 ℃, reacted 1～5 hour, glycerine reaches 70～95% to the transformation efficiency of triglyceride, in the triglyceride of generation 1, the content of 3-triglyceride reaches 80%
Described lipase is the lipase that derives from Candida antarctica, Thermomyces lanuginosus, Rhizomucor miehei or Rhizopus.oryza;
The lipid acid donor is lipid acid, fatty acid short-chain ester or both mixtures.
2. according to the described technology of claim 1, it is characterized in that the use-pattern of lipase is:
Certain single fat enzyme, the perhaps combination of different lipase.
3. according to the described technology of claim 1, it is characterized in that described lipid acid is one or more the mixture that has in the lipid acid of 10～22 carbon atoms.
4. according to the described technology of claim 1, it is characterized in that described fatty acid short-chain ester is one or more the mixture in the methyl esters, ethyl ester, propyl ester, butyl ester, pentyl ester of described lipid acid.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2008101050820A CN101260417B (en) | 2008-04-25 | 2008-04-25 | Technique for preparing 1,3-diglyceride in petroleum ether medium system by enzyme method |
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| CN2008101050820A CN101260417B (en) | 2008-04-25 | 2008-04-25 | Technique for preparing 1,3-diglyceride in petroleum ether medium system by enzyme method |
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| CN101260417B true CN101260417B (en) | 2011-05-11 |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1560020A (en) * | 2004-02-16 | 2005-01-05 | 华南理工大学 | Preparation process of diglyceride |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1560020A (en) * | 2004-02-16 | 2005-01-05 | 华南理工大学 | Preparation process of diglyceride |
Non-Patent Citations (3)
| Title |
|---|
| Matthias Berger et al..Enzymatic Esterification of Glycerol I. Lipase-Catalyzed Synthesis of Regioisomerically Pure 1,3-sn-Diacylglycerols.《JAOCS》.1992,第69卷(第10期),955-959. * |
| MatthiasBergeretal..EnzymaticEsterificationofGlycerolI.Lipase-CatalyzedSynthesisofRegioisomericallyPure1 3-sn-Diacylglycerols.《JAOCS》.1992 |
| Seong Koon Lo et al.Lipase-catalysed production and chemical composition of diacylglycerols from soybean oil deodoriser distillate.《Eur.J.Lipid Sci.Technol》.2004,第106卷218–224. * |
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