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Method for preparing sugar ester through immobilized enzyme catalysis under supercritical CO2 process

An immobilized enzyme, catalytic preparation technology, applied in biochemical equipment and methods, immobilized on/in organic carriers, enzymes, etc., can solve the problems of a large number of organic solvents, long reaction time, complex process, etc. The effect of less environmental pollution, high utilization rate of raw materials, and non-toxic reaction conditions

Active Publication Date: 2019-01-22
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to overcome the technical defects existing in the prior art, such as: complex process, long reaction time, relatively high cost, large use of organic solvents and other problems, the present invention provides a new method for the preparation of sugar esters in a green and efficient manner , especially a supercritical CO 2 Process for the preparation of sugar esters catalyzed by immobilized enzymes

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Ethylation modification of lipase:

[0027] Dissolve 10 mmol of bromopropionic acid in 10 mL of acetonitrile and add it to a dry round-bottomed flask. After the dissolution is complete, slowly add 1.1 mmol of vinylimidazole dropwise, and reflux at 60 °C for 5 hours with magnetic stirring. After the reaction, use Extract twice with anhydrous ether (5*10mL), remove the yellow oily substance in the lower layer, and vacuum-dry at 70°C for 24 hours to obtain a yellow thick liquid 1-vinyl 3-propionyl imidazolium bromide (modifier);

[0028] Take 1 mmol of 1-vinyl 3-propionyl imidazolium bromide, add 1 mmol carbonyldiimidazole, stir magnetically under the action of 2 mL of anhydrous dimethyl sulfoxide, react at room temperature for 2 h and stop, after the reaction is completed , to obtain the active body; add 90 μL of the active body to 5 mL of Candida rugosa lipase solution with a concentration of 150 μM, stop the reaction after 8 h of magnetic stirring at 0 °C, dialyze f...

Embodiment 2

[0034] (1) Ethylation modification of lipase:

[0035] Dissolve 10 mmol of bromopropionic acid in 10 mL of acetonitrile and add it into a dry round-bottomed flask. After the dissolution is complete, slowly add 1.1 mmol of propenylimidazole dropwise, and reflux at 80°C for 7 hours with magnetic stirring. After the reaction is complete, use Extract twice with anhydrous ether (5*10mL), remove the yellow oily substance in the lower layer, and vacuum-dry at 70°C for 24 hours to obtain a yellow thick liquid 1-propenyl 3-propionyl imidazolium bromide (modifier);

[0036] Take 1 mmol of 1-propenyl 3-propionyl imidazolium bromide, add 1 mmol of carbonyldiimidazole, stir magnetically under the action of 2 mL of anhydrous dimethyl sulfoxide, react at room temperature for 5 h and stop, after the reaction is completed , to obtain the active body; add 90 μL of the active body to 5 mL of Candida antarctica lipase solution with a concentration of 200 μM, stop the reaction after magnetic stirr...

Embodiment 3

[0042] (1) Ethylation modification of lipase:

[0043] Dissolve 10 mmol of bromopropionic acid in 10 mL of acetonitrile and add it into a dry round-bottomed flask. After the dissolution is complete, slowly add 1.1 mmol of vinylimidazole dropwise, and reflux at 100 °C for 10 h with magnetic stirring. After the reaction is complete, use Extract twice with anhydrous ether (5*10mL), remove the yellow oily substance in the lower layer, and vacuum-dry at 70°C for 24 hours to obtain a yellow thick liquid 1-vinyl 3-propionyl imidazolium bromide (modifier);

[0044] Take 1 mmol of 1-vinyl 3-propionyl imidazolium bromide, add 1 mmol carbonyldiimidazole, stir magnetically under the action of 2 mL of anhydrous dimethyl sulfoxide, react at room temperature for 8 h and stop, after the reaction is completed , to obtain the active body; add 90 μL of the active body to 5 mL of porcine pancreatic lipase solution with a concentration of 350 μM, stop the reaction after 24 hours of magnetic stirri...

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PUM

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Abstract

The invention belongs to the technical field of biological catalysis, and in particular relates to a method for preparing sugar ester through immobilized enzyme catalysis under the supercritical CO2 process. The method for preparing sugar ester through immobilized enzyme catalysis specifically comprises the following steps: taking bromopropionic acid, acetonitrile and imidazole compounds, and carrying out reaction to obtain a modifier; adding the modifier and carbonyldiimidazole into anhydrous dimethylsulfoxide, and carrying out stirring for reaction, thus obtaining an active body; adding theactive body into a lipase solution, and carrying out reaction to obtain an acylated lipase solution; adding monomer acrylamide into the acylated lipase solution, carrying out stirring for dissolving,introducing nitrogen gas, adding ammonium persulfate and tetramethylethylenediamine, and carrying out polymerization reaction, thus obtaining the immobilized lipase; and mixing sugar with fatty acid,thus obtaining a reactant, adding the immobilized lipase, placing in a reaction still, adding CO2 medium, and carrying out stirring reaction, thus obtaining the sugar ester. For the method provided bythe invention, the reaction conditions are mild, the operation is simple, the conversion rate is high, meanwhile, the enzyme catalyzer can be repeatedly used, the pollution to the environment is small, and the method is expected to realize the industrial production.

Description

technical field [0001] The invention belongs to the technical field of biocatalysis, in particular to a supercritical CO 2 A method for preparing sugar esters catalyzed by immobilized enzymes under the process. Background technique [0002] Sugar ester compounds widely exist in nature and are a class of substances with important physiological activities. They play an important role in the transmembrane transport of substances and energy transfer, as well as in the metabolic process in the living body. As a biological functional molecule and chemical raw material, sugar ester has important application value. For example, sugar ester compounds have a special amphiphilic structure, so they can be used as a nonionic biosurfactant. Compared with the chemical surfactants from the petroleum industry, this kind of surfactants not only has excellent surface properties, but also has the advantages of biocompatibility, biodegradability and non-toxicity, and is a kind of environmental...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/64C12P19/02C12P19/12C12N11/08
CPCC12N9/20C12N11/08C12P7/6454C12P19/02C12P19/12C12Y301/01003Y02P20/54
Inventor 邹彬张黎明夏姣姣储嫣红霍书豪
Owner JIANGSU UNIV
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