Method for synthesizing 5-hydroxymethylfurfural ester derivative under enzymatic catalysis

A technology of hydroxymethylfurfural ester and hydroxymethylfurfural, which is applied in the field of bioenergy, fine chemical industry, and enzyme catalysis, can solve the problems of harsh reaction conditions, unfriendly use environment, and complicated process of chemical methods, and achieve repeated utilization, The effect of lowering the activation energy of the reaction and increasing the selectivity

Inactive Publication Date: 2016-08-10
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the chemical synthesis of HMF ester derivatives has made some progress, and the yield is high (usually higher than 80%), there are still harsh reaction conditions, complex processes, and the use of environmentally unfriendly strong aci

Method used

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  • Method for synthesizing 5-hydroxymethylfurfural ester derivative under enzymatic catalysis
  • Method for synthesizing 5-hydroxymethylfurfural ester derivative under enzymatic catalysis
  • Method for synthesizing 5-hydroxymethylfurfural ester derivative under enzymatic catalysis

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 1 mL of 2-methyltetrahydrofuran, 1 mL of levulinic acid, 50 mM HMF, 0.1 g Molecular sieves were added to a stoppered Erlenmeyer flask, then 20 mg of immobilized lipase B from Candida antarctica (purchased from Novozymes) was added, placed in a constant temperature oscillator at 40 °C and 200 r / min under normal pressure, and reacted for 12 h Finally, liquid phase analysis showed that the conversion rate of HMF reached 95%, and HMF levulinate was the only product. as attached figure 1 As shown, the retention times of levulinic acid, HMF, HMF levulinate and 9-fluorenone (internal standard) were 4.50, 4.84, 7.99 and 12.77 min, respectively. The target product was separated by column chromatography with a yield of 90%. NMR analysis (attached figure 2 and 3 ) shows that the target product is HMF levulinate.

Embodiment 2

[0031] 1 mL of 2-methyltetrahydrofuran, 1 mL of levulinic acid, 50 mM HMF, 0.1 g Molecular sieves were added to a stoppered Erlenmeyer flask, and then 20 mg of immobilized lipase from Thermomyces lanuginosus (purchased from Novozymes) was added, placed in a constant temperature oscillator at 40°C and 200 r / min under normal pressure, and reacted for 24 hours. , liquid phase analysis showed that the conversion of HMF was 3%, and HMF levulinate was the only product.

Embodiment 3

[0033] 1 mL of 2-methyltetrahydrofuran, 1 mL of levulinic acid, 50 mM HMF, 0.1 g Molecular sieves were added to a stoppered Erlenmeyer flask, then 20 mg of immobilized lipase derived from Pseudomonas cepacia (purchased from Japan Amano Company) was added, placed in a constant temperature oscillator at 40 ° C and 200 r / min under normal pressure, and after 24 hours of reaction, the liquid Phase analysis indicated 4% conversion of HMF with HMF levulinate as the only product.

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Abstract

The invention discloses a method for synthesizing a 5-hydroxymethylfurfural ester derivative under enzymatic catalysis. The method is characterized by comprising the following steps: uniformly mixing an organic solvent and an acyl donor, adding 5-hydroxymethylfurfural, immobilized lipase and a 4 angstrom molecular sieve, and performing stirring reaction at 20 to 50 DEG C to obtain the 5-hydroxymethylfurfural ester derivative. The method has the advantages of mild reaction condition, environmental friendliness, process simplicity, less side reaction, high selectivity and the like.

Description

technical field [0001] The invention belongs to the fields of enzyme catalysis, bioenergy and fine chemical industry, and in particular relates to a method for synthesizing 5-hydroxymethylfurfural ester derivatives by catalyzing 5-hydroxymethylfurfural acylation with immobilized lipase. Background technique [0002] 5-Hydroxymethylfurfural (HMF) is one of the 14 most potential bio-based platform compounds selected by the US Department of Energy (Green Chem.2010, 12, 539). After carbohydrates are dehydrated, HMF can be prepared. HMF molecules contain active groups such as hydroxyl groups and aldehyde groups, which can be chemically modified to synthesize various high value-added products. For example, HMF can be selectively oxidized to synthesize 2,5-furandicarbaldehyde, 2,5-furandicarboxylic acid, etc. These compounds are important intermediates for the preparation of drugs, polymers and energy sources (Chem.Rev.2013,113, 1499). In addition, HMF can also be acylated to sy...

Claims

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Application Information

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IPC IPC(8): C12P17/04
CPCC12P17/04
Inventor 李宁秦烨芝宗敏华
Owner SOUTH CHINA UNIV OF TECH
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