Method of using lipase to catalyze and synthesize mannose-6-laurate on line

A technology of laurate and mannose, applied in the field of lipase-catalyzed online controllable selective synthesis of mannose-6-laurate, which can solve the problems of low conversion rate and selectivity, long reaction time, etc. Effects of reaction time, reduced usage, high conversion and reaction selectivity

Active Publication Date: 2013-07-03
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] At present, scholars at home and abroad have studied the enzyme-catalyzed synthesis of mannose esters in organic media, but this method often requires a long reaction time (24h), and the conversion rate and selectivity of the reaction are not high. A lipase-catalyzed selective synthesis of mannose laurate in a channel reactor, aiming to find an efficient and environmentally friendly online controllable selective synthesis of mannose laurate monoester

Method used

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  • Method of using lipase to catalyze and synthesize mannose-6-laurate on line
  • Method of using lipase to catalyze and synthesize mannose-6-laurate on line
  • Method of using lipase to catalyze and synthesize mannose-6-laurate on line

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Synthesis of Mannose-6-laurate

[0027]

[0028] device reference figure 1 : Mannose (0.4mmol) was dissolved in 10mL tert-amyl alcohol: DMSO=4:1 (v / v) mixed solvent, vinyl laurate (4.4mmol) was dissolved in 10mL tert-amyl alcohol, and then packed in Ready-to-use in a 10mL syringe. 0.87g of lipase Lipozyme TLIM was evenly filled in the reaction channel of the microfluidic channel reactor, and driven by the PHD2000 syringe pump, the two reaction solutions were separated at 10.4 μL min -1 The flow rate enters the reaction channel through the "Y" joint for reaction, and the temperature of the reactor is controlled at 52°C by a water bath thermostat. The reaction solution flows continuously in the reaction channel for 30 minutes, and the reaction results are tracked and detected by thin-layer chromatography (TLC).

[0029] The reaction solution was collected online by the product collector, the solvent was distilled off under reduced pressure, and the column ...

Embodiment 2-5

[0033] Change the temperature of the microfluidic channel reactor, others are the same as in Example 1, and the reaction results are as shown in Table 1:

[0034] Table 1: Effect of Temperature on Reaction

[0035]

[0036] The results in Table 1 show that when the flow rate is 10.4 μL min -1 , when the reaction time is 30min, the conversion rate increases obviously with the increase of the reaction temperature. When the reaction temperature reaches 52°C, the conversion rate and selectivity of the reaction are the best. The decrease in enzyme activity leads to a decrease in the conversion rate and selectivity of the reaction, so the optimal reaction temperature of mannose laurate in the microfluidic microchannel reactor in the present invention is 52°C.

Embodiment 6-9

[0038] Change the substrate ratio of vinyl laurate and mannose in the microfluidic microchannel reactor to be 8: 1 (Example 6), 9: 1 (Example 7), 10: 1 (Example 8), 12: 1 (embodiment 9), other are with embodiment 1, and the result is as shown in table 2.

[0039] Table 2: Effect of Mannose to Vinyl Laurate Substrate Ratio on Reaction

[0040] Example

[0041] 9

[0042] The result of table 2 shows, along with the increase of reactant vinyl laurate, the conversion ratio of reaction also thereupon increases, and when substrate ratio is 11: 1, mannose is converted into mannose-6-palmitic acid mono ester, and the selectivity of the reaction is also very high, almost no other mannose esters are formed. Now if continue to increase the consumption of reactant vinyl laurate, the conversion rate and the selectivity of mannose-6-laurate will decrease instead. Therefore, the optimum substrate ratio for the reaction of the present invention is 11:1, under which rea...

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Abstract

The invention discloses a method of using lipase to catalyze and synthesize mannose-6-laurate on line. The method comprises the following steps: taking mannose and vinyl laurate as raw materials according to molar ratio of 1:8-12, taking 0.5-1.0 g of lipase Lipozyme TLIM as a catalyst, taking tert-amyl alcohol and DMSO (dimethyl sulfoxide) mixed solvent as a reaction solvent, uniformly filling the lipase Lipozyme TLIM into a reaction channel of a microfluidic channel reactor, wherein the inner diameter of the reaction channel of the microfluidic channel reactor is 0.8-2.4 mm, and the reaction channel is 0.5-1.0 m long, continuously introducing the raw materials and the reaction solvent into the reaction channel to perform acylation reaction, controlling the temperature of acylation reaction to be 40-55 DEG C, and keeping the acylation reaction for 15-35 min, on line collecting reaction liquid, and conventionally post-processing the reaction liquid to obtain mannose-6-laurate. The method has the advantages of short reaction time, high selectivity and high yield.

Description

(1) Technical field [0001] The invention relates to a lipase-catalyzed method for on-line controllable selective synthesis of mannose-6-laurate. (2) Background technology [0002] Sugar ester is an excellent non-ionic surfactant, which uses natural renewable resource sugar widely existing in nature as raw material, and has broad development prospects. Today's surfactant industry is developing in the direction of green chemistry, which gradually requires non-toxic products, regenerated reaction raw materials, and green reaction processes. As an excellent natural surfactant, sugar esters meet the two requirements of green chemistry: non-toxic products and renewable raw materials, but the reaction process still needs to be further green. [0003] At present, the sugar esters commercially produced at home and abroad are all synthesized by chemical methods, which have many shortcomings, mainly including: the conditions in the reaction process are severe, side reactions such as c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P19/02
Inventor 杜理华罗锡平顾生妹张航诚胡玉婷
Owner ZHEJIANG UNIV OF TECH
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