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Process for double-enzyme coupling-chemical synthesis of epsilon-caprolactone

A chemical method and caprolactone technology, applied in the direction of biochemical equipment and methods, enzymes, hydrolytic enzymes, etc., can solve the problems of lack of commercial enzymes and coenzyme cycles, high use costs, etc., to avoid explosion risks and reduce pH The effect of falling, safe and easy-to-handle reaction conditions

Inactive Publication Date: 2017-05-24
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Enzyme-catalyzed Bayer-Villiger reaction can avoid the use of peroxyacids, but the main problem is the lack of commercial enzymes and coenzyme cycle problems, and the cost of enzymes is relatively high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] A process for synthesizing ε-caprolactone by double-enzyme coupling-chemical method, the specific steps are as follows: firstly, glucose oxidase (GOD) / candida antarctica lipase B (CALB) double-enzyme cross-linked aggregates are prepared, and the process As follows: Dissolve 0.75Kg of GOD enzyme powder (≥500U / g) and CALB enzyme powder (≥200U / g) (the ratio of enzyme activity is 5:1) with 5L of pH 6.0 phosphate buffer solution, at 4°C Add 3 kg of ammonium sulfate under slow stirring at 120 rpm, continue stirring for 1 hour, add cross-linking agent glutaraldehyde to make its concentration 0.1%, cross-link for 2 hours, centrifuge the mixed solution at 4°C, 5000 × g for 5 minutes, remove the supernatant , the precipitate was washed with deionized water, and freeze-dried to obtain GOD / CALB double-enzyme cross-linking enzyme aggregates.

[0046] The above-mentioned GOD / CALB double-enzyme cross-linking enzyme aggregate was used as a catalyst, and the usage amount of the double-e...

Embodiment 2

[0048]A process for synthesizing ε-caprolactone by double-enzyme coupling-chemical method, the specific steps are as follows: firstly, glucose oxidase (GOD) / candida antarctica lipase B (CALB) double-enzyme cross-linked aggregates are prepared, and the process As follows: Dissolve 1.0Kg of GOD enzyme powder (≥500U / g) and CALB enzyme powder (≥200U / g) (the ratio of enzyme activity is 6:1) with 10L of pH 7.0 phosphate buffer, at 4°C Add 5kg ammonium sulfate under slow stirring at 120rpm, continue stirring for 1h, add crosslinking agent glutaraldehyde to make its concentration 0.2%, crosslink for 2.5h, centrifuge the mixed solution at 4°C, 5000×g for 5min, remove the supernatant The precipitation was washed with deionized water, and freeze-dried to obtain GOD / CALB double-enzyme cross-linked enzyme aggregates.

[0049] The above-mentioned GOD / CALB double-enzyme cross-linking enzyme aggregate was used as a catalyst, and the usage amount of the double-enzyme cross-linking enzyme aggre...

Embodiment 3

[0051] A process for synthesizing ε-caprolactone by double-enzyme coupling-chemical method, the specific steps are as follows: firstly, glucose oxidase (GOD) / candida antarctica lipase B (CALB) double-enzyme cross-linked aggregates are prepared, and the process As follows: Dissolve 1.5Kg of GOD enzyme powder (≥500U / g) and CALB enzyme powder (≥200U / g) (the ratio of enzyme activity is 8:1) with 15L of pH 6.5 phosphate buffer, at 4°C Add 6 kg of ammonium sulfate under slow stirring at 120 rpm, continue stirring for 1 h, add cross-linking agent glutaraldehyde to make its concentration 0.3%, cross-link for 3 h, centrifuge the mixed solution at 4°C, 5000 × g for 5 min, remove the supernatant , the precipitate was washed with deionized water, and freeze-dried to obtain GOD / CALB double-enzyme cross-linking enzyme aggregates.

[0052] The above-mentioned GOD / CALB double-enzyme cross-linking enzyme aggregate was used as a catalyst, and the usage amount of the double-enzyme cross-linking ...

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Abstract

The invention relates to a process for double-enzyme coupling-chemical synthesis of epsilon-caprolactone; hydrogen peroxide generated in situ from GOD oxidation of glucose by a GOD / CALB or GOD / ROL double-enzyme cross-linked enzyme aggregate is used as an oxidant, at the same time, peroxy acid is generated in situ through catalyzing oxidation of an acyl donor by CALB or ROL in the cross-linked enzyme aggregate, and then epsilon-caprolactone (epsilon-CL) is generated through oxidation of cyclohexanone by peroxy acid. The yield of the epsilon-caprolactone reaches 97% or more, and the selectivity of the epsilon-caprolactone is 100%. The process reduces enzyme inactivation caused by too high concentration of hydrogen peroxide, avoids an easily explosiveness risk possibly caused by direct addition of peroxy acid, reduces the influence of decrease of enzyme micro-environment pH on the enzyme activity, and can reduce the inhibition of a substrate on an enzyme.

Description

technical field [0001] The invention belongs to the technical field of chemistry-enzyme catalysis, and specifically relates to a process for synthesizing ε-caprolactone by a double-enzyme coupling-chemical method, that is, using glucose oxidase (GOD) / Candida antarctica lipase B (CALB) dual Enzyme-crosslinked enzyme aggregates catalyze the coupling reaction of glucose oxidation and acyl donor perhydrolysis to generate peroxyacid in situ, and then use peroxyacid to oxidize cyclohexanone to caprolactone (ε-CL). Background technique [0002] ε-caprolactone is a widely used organic synthesis intermediate, which can be used to produce synthetic fibers, plastics, films, coatings and plasticizers, etc., especially obtained by polymerizing ε-caprolactone or other monomers Polycaprolactone (PCL) is a kind of fully degradable polymer material, which has good biocompatibility, non-toxicity and good drug penetration, and has been well applied in biomedical engineering. [0003] The main...

Claims

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Application Information

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IPC IPC(8): C12P17/08C12N11/00
CPCC12N9/0006C12N9/20C12N11/00C12P17/08C12Y101/03004C12Y301/01003
Inventor 张媛媛赵兰杰鲁佩玉王丽红
Owner QINGDAO UNIV OF SCI & TECH
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