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Method for catalytically synthesizing sucrose fatty acid ester by lipase in organic solvent

A technology for synthesizing fatty acids and organic solvents, which is applied in the field of synthesizing fatty acid sucrose esters catalyzed by lipase, which can solve the problems of high production cost and production equipment, reduced production, high toxicity of strong polar organic solvents, etc., to reduce production costs and ensure safety The effect of improving performance and enhancing catalytic activity

Pending Publication Date: 2021-06-08
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the yield of chemically synthesized sucrose esters is higher, it has the following defects: (1) the regioselectivity of chemical catalysts is relatively poor, and the catalyzed products also have by-products such as diesters and triesters except monoesters, which make the raw materials The utilization rate has dropped significantly, and it is not conducive to the separation and purification of the main product, which greatly increases the cost of downstream projects; (2) strong polar organic solvents such as DMSO are highly toxic and have a high boiling point, and it is difficult to remove them with existing separation techniques. Thereby the application of the sucrose ester of gained in the fields such as food, daily chemical product is limited; (3) the reaction condition of chemical method is harsh, usually needs to react under conditions such as high temperature, reduced pressure, and production cost and the requirement to production equipment are relatively high. High, and high temperature is easy to denature and color sucrose esters, thereby reducing yield
The ionization state of lipase largely determines its active conformation, however, there are few reports on the effect of lipase ionization state on the synthesis of sucrose esters in organic media

Method used

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  • Method for catalytically synthesizing sucrose fatty acid ester by lipase in organic solvent
  • Method for catalytically synthesizing sucrose fatty acid ester by lipase in organic solvent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Grind the sucrose into fine powder and dry it in a vacuum oven at 60°C for 6 hours before use. 0.1 mmol (0.034 g) of sucrose, 2.25 mmol (585 μL) of vinyl laurate, and 15 mL of tert-amyl alcohol or tert-butanol were added to two 50 mL round-bottomed flasks, respectively, and stirred for 1 h in a 60° C. water bath. Then add 0.1g Novozym435, 0.09g sodium laurate and 0.4g respectively Molecular sieves were reacted in a water bath at 60°C for 24h. After the reaction, the reaction solution was filtered to recover Novozym435, then washed with tert-amyl alcohol, and dried in vacuum for use. The sucrose monoester concentration in the tert-amyl alcohol system was 2.32 g / L, and the yield was 66.9% by high performance liquid chromatography; the sucrose monoester concentration in the tert-butanol system was 2.04 g / L, and the yield was 58.8%.

[0026] It can be seen that the yield of tert-amyl alcohol system is higher than that of tert-butanol system, so tert-amyl alcohol is used ...

Embodiment 2

[0028] Grind the sucrose into fine powder and dry it in a vacuum oven at 60°C for 6 hours before use. Add 0.08 / 0.1 / 0.4 / 0.6 / 0.8 mmol of sucrose, 2.25 mmol (585 μL) of vinyl laurate and 15 mL of tert-amyl alcohol to five 50 mL round-bottomed flasks, respectively, and stir in a 60° C. water bath for 1 h. Then add 0.1g Novozyme435, 0.09g sodium laurate and 0.4g respectively to the mixture. Molecular sieves were reacted in a water bath at 60°C for 24h. After the reaction, the reaction solution was filtered to recover Novozym435, then washed with tert-amyl alcohol, and dried in vacuum for use. The sucrose monoester concentrations in the tert-amyl alcohol system were measured by high performance liquid chromatography to be 2.3 / 3.61 / 4.26 / 4.28 / 4.13 g / L, respectively.

[0029] It can be seen that the yield of sucrose monoester increases with the increase of sucrose concentration, but when the sucrose concentration in the system is greater than 0.6mmol / 15mL, the yield of sucrose monoe...

Embodiment 3

[0031] Grind the sucrose into fine powder and dry it in a vacuum oven at 60°C for 6 hours before use. 1.51 / 1.70 / 2.25 / 3.40 / 3.61 mmol of vinyl laurate, 0.4 mmol (0.137 g) of sucrose and 15 mL of tert-amyl alcohol were added to five 50 mL round-bottomed flasks, and the mixture was stirred in a 60° C. water bath for 1 h. Add 0.1g Novozyme435, 0.09g sodium laurate and 0.4g respectively to the mixture Molecular sieves were reacted in a water bath at 75°C for 24h. After the reaction, the reaction solution was filtered to recover Novozym435, then washed with tert-amyl alcohol, and dried in vacuum for use. The sucrose monoester concentrations in the tert-amyl alcohol system were measured by high performance liquid chromatography to be 4.86 / 5.40 / 6.42 / 6.40 / 6.37 g / L, respectively.

[0032] It can be seen that the production of sucrose monoester increases with the increase of the concentration of vinyl laurate, but when the concentration of vinyl laurate in the system is greater than 3....

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Abstract

The invention discloses a method for catalytically synthesizing sucrose fatty acid ester by lipase in an organic solvent. According to the method, a low-toxicity organic solvent is used as a reaction medium, substrates sucrose and vinyl laurate are added, sucrose laurate monoester is synthesized under the catalysis of lipase, and lipase can be deprotonated by adding an alkaline substance, so that the lipase activity is greatly improved. According to the method disclosed by the invention, the target of obtaining higher sucrose ester yield in the low-toxicity organic solvent by using a biological method is achieved, and almost all catalytic products are sucrose monoesters, so that the separation and purification of the products are greatly simplified, and the method is a green, safe and low-cost production method.

Description

[0001] (1) Technical field [0002] The invention relates to a method for synthesizing fatty acid sucrose ester catalyzed by lipase in an organic solvent. [0003] (2) Background technology [0004] Fatty acid sucrose ester is a non-ionic surfactant with the advantages of non-toxicity, good biocompatibility, non-irritant and biodegradation. By adjusting the chain length and degree of substitution of the acyl donor, various functional properties of sucrose esters, such as critical micelle concentration (CMC), hydrophilic-lipophilic balance (HLB), etc., can be adjusted in a wide range, so that sucrose Esters meet specific application conditions. Therefore, sucrose esters are widely used in food, daily chemicals, pharmaceuticals and other industries. For example, sucrose ester is a food emulsifier recommended by the Food and Agriculture Organization of the United Nations and the World Health Organization; lauric acid sucrose monoester has a strong inhibitory effect on harmful ba...

Claims

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Application Information

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IPC IPC(8): C12P19/12
CPCC12P19/12
Inventor 陈小龙张珂睿范永仙陆跃乐叶康朱林江
Owner ZHEJIANG UNIV OF TECH
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