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A kind of synthetic method of propyl p-hydroxybenzoate

A technology of propyl hydroxybenzoate and synthesis method, which is applied in the field of biocatalytic synthesis, can solve problems such as unreported research, and achieve the effects of low equipment requirements, low cost, and mild reaction

Active Publication Date: 2020-05-08
ANHUI POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the natural substrates of tannase are tannic acid, gallic acid and their esters, and there is no report on the use of tannic acid to catalyze the synthesis of propyl p-hydroxybenzoate

Method used

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  • A kind of synthetic method of propyl p-hydroxybenzoate
  • A kind of synthetic method of propyl p-hydroxybenzoate
  • A kind of synthetic method of propyl p-hydroxybenzoate

Examples

Experimental program
Comparison scheme
Effect test

experiment example 1

[0023] Experimental Example 1: Reaction Feasibility Study

[0024] 1. Preparation of bioimprinting enzymes

[0025] Add 1 mL of 50 mg / mL p-hydroxybenzoic acid (PHBA), 0.2 mL of 250 mg / mL tannase, 0.5 g of diatomaceous earth, and 4 mL of acetic acid buffer into a 50 mL Erlenmeyer flask and vortex for 3-5 minutes. The above mixture was placed at -20°C overnight, then freeze-dried at a low temperature to form a powder, and stored at 4°C for future use.

[0026] 2. Preparation of reaction system

[0027] 2.1. Enzyme-free system: Add 1 mL of n-propanol, 18 mL of n-hexane, 1 mL of 50 mg / mL PHBA, 0.3 mL of acetic acid buffer, and 0.5 g of diatomaceous earth into a 50 mL Erlenmeyer flask to prepare a reaction system.

[0028] 2.2. Natural enzyme system: Add 1mL of n-propanol, 0.2mL of 250mg / mL tannase, 0.5g of diatomaceous earth, and 4mL of acetic acid buffer into a 50mL Erlenmeyer flask and vortex for 3-5min. The above mixture was placed at -20°C overnight, freeze-dried at low tem...

experiment example 2

[0042] Experimental example 2: Determination of the reaction system

[0043] 1. Selection of reaction medium

[0044] Add 4 mL of n-propanol to five 50 mL Erlenmeyer flasks equipped with immobilized imprinted tannase in 1 of Experimental Example 1, and then add 15 mL of n-hexane, n-pentane, n-propanol, benzene and petroleum ether ( 30~60℃), 1mL acetic acid buffer solution, and prepare the catalytic system. Place the Erlenmeyer flask containing the reaction system in a micro-shaking incubator at 40°C and 200 rpm, and catalyze the reaction for 24 hours. The result is as Figure 4 As shown, when the reaction medium is n-propanol, the catalytic performance of the enzyme is the best, and the conversion rate of the substrate is the highest, reaching 4.23% (Table 2). Therefore, n-propanol was chosen as the reaction medium.

[0045] Table 2 The substrate conversion rate of different media

[0046]

[0047]

[0048] 2. Determination of the optimal content of n-propanol

[0...

Embodiment 1

[0053] Add 1 mL of 50 mg / mL PHBA, 0.2 mL of 250 mg / mL tannase, 0.5 g of diatomaceous earth, and 4 mL of acetic acid buffer into a 50 mL Erlenmeyer flask and vortex for 3-5 minutes. The above mixture was placed at -20°C overnight, then freeze-dried at a low temperature to form a powder, and stored at 4°C for future use. To the 50 mL Erlenmeyer flask containing the prepared bioimprinted tannase, add a mixed solution of n-propanol-acetic acid buffer with a total volume of 20 mL, wherein the volume percentage of n-propanol is 50%. Prepared as a catalytic system. Place the Erlenmeyer flask containing the reaction system in a micro-shaking incubator at 40°C and 200 rpm, and catalyze the reaction for 24 hours. The conversion rate of the final substrate was 26.47%, and the purity was 99.95%.

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Abstract

The invention discloses a synthesis method of propyl p-hydroxybenzoate. The synthesis method comprises immobilized bio-imprinting enzyme. An imprinting system of the bio-imprinting enzyme is prepared from tannase, p-hydroxybenzonic acid and kieselguhr according to a mass ratio of (0.1-1): (1-3): 10. A buffer solution for fixing the immobilized bio-imprinting enzyme is an acetic acid buffer solution which has a pH value of 6.0 and the concentration of 100mM. According to the synthesis method, the propyl p-hydroxybenzoate is catalytically synthesized by using the immobilized bio-imprinting tannase, and a compound solvent system of the n-propyl alcohol-acetic acid buffer solution is used for improving the catalytic efficiency. After the method is adopted, the substrate conversion rate reaches 26.5%. The method is mild in reaction, low in energy consumption and less in pollution, and is an efficient, convenient and fast production way, so that a new way is provided for realizing the green and efficient production of propyl p-hydroxybenzoate.

Description

technical field [0001] The invention relates to a method for synthesizing propyl p-hydroxybenzoate, belonging to the technical field of biocatalytic synthesis. Background technique [0002] Propyl p-hydroxybenzoate is an internationally recognized safe, efficient and broad-spectrum preservative. It has the characteristics of extremely low toxicity, non-irritating and relatively stable in a wide pH range. It has a wide range of antibacterial effects on mold, yeast and bacteria. It has always been a widely used preservative in cosmetics and pharmaceuticals. Propyl p-hydroxybenzoate has a certain influence in experiments in the field of life science research, and can be used in biochemical research and tissue culture. At present, the commonly used production method of propyl p-hydroxybenzoate is mainly based on the esterification reaction of chemical catalyst. The traditional chemical catalysis method is carried out under high temperature, high pressure and strong corrosive c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P7/62
CPCC12P7/62
Inventor 聂光军张二伟岳文瑾刘宁赵锐陶勇薛正莲刘艳王洲
Owner ANHUI POLYTECHNIC UNIV
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