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No-catalyst ferulaldhyde hydrodizing process to prepare vanillin in near critical water medium

A technology of near-critical water and catalytic hydrolysis, which is applied in the direction of alkyne addition to prepare oxygenates, organic chemistry, etc., can solve the problems of raw material source limitation, high product cost, and no relevant reports of industrialization, etc., and achieve simple reaction process, The effect of good quality and high product yield

Inactive Publication Date: 2007-01-03
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Eugenol is a natural raw material for the preparation of vanillin, but the main production areas are distributed in Southeast Asia, and the source of raw materials is limited, which makes the product cost higher
[0005] Biosynthesis methods include plant cell culture method and microbial fermentation method, etc., which are still in the laboratory research stage, and there are no relevant reports on industrialization.

Method used

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  • No-catalyst ferulaldhyde hydrodizing process to prepare vanillin in near critical water medium
  • No-catalyst ferulaldhyde hydrodizing process to prepare vanillin in near critical water medium

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Add 200g deionized water and 200g coniferaldehyde into a 500mL intermittent high-pressure reactor, start stirring, heat up to boiling under normal pressure, open the exhaust valve for 2 minutes, and use water vapor to remove the air in the kettle; continue to heat up to 200°C for 8 hours for hydrolysis The hydrolyzate is divided into an aqueous phase and an organic phase after cooling, the aqueous phase is extracted with chloroform, and the extraction phase is evaporated to remove chloroform and then merged with the organic phase; the combined organic phase is distilled under reduced pressure to obtain crude vanillin, and then crystallized with toluene, Ethanol recrystallization yielded 32.2 g of the product vanillin.

Embodiment 2

[0026] Add 260g deionized water and 130g coniferaldehyde into a 500mL intermittent high-pressure reactor, start stirring, heat up to boiling under normal pressure, open the exhaust valve for 3min, and use water vapor to remove the air in the kettle; continue to heat up to 240°C for 4h for hydrolysis The hydrolyzate is divided into an aqueous phase and an organic phase after cooling, and the aqueous phase is extracted with dichloromethane, and the extracted phase is evaporated to remove the dichloromethane and merged with the organic phase; the combined organic phase is distilled under reduced pressure to obtain the crude vanillin, and then After crystallization from toluene and recrystallization from ethanol, 64.6 g of vanillin was obtained.

Embodiment 3

[0028] Add 300g deionized water and 100g coniferaldehyde into a 500mL intermittent high-pressure reactor, start stirring, heat up to boiling under normal pressure, open the exhaust valve for 4min, and use water vapor to remove the air in the kettle; continue to heat up to 260°C for 3h for hydrolysis The hydrolyzate is divided into an aqueous phase and an organic phase after cooling, and the aqueous phase is extracted with n-butanol, and the extracted phase is evaporated to remove n-butanol and merged with the organic phase; the combined organic phase is distilled under reduced pressure to obtain the crude vanillin, and then After crystallization from toluene and recrystallization from ethanol, 75.4 g of vanillin was obtained.

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Abstract

The present invention discloses no-catalyst ferulaaldehyde hydrolyzing process to prepare vanillin in near critical water medium. The process includes the following steps: 1. adding deionized water and ferulaaldehyde in the mass ratio of 1-6 into a high pressure reactor, heating at normal pressure and while stirring to boil, and opening the exhaust valve for 2-5 min; 2 further heating to 200-320 deg.c for hydrolysis for 0.5-8 hr; 3 cooling the hydrolysate, separating into water phase and organic phase, extracting the water phase with organic solvent and distilling the extracted phase before merging with the organic phase; 4 decompression distilling the merged organic phase to obtain crude vanillin product, crystallizing in toluene and re-crystallizing in ethanol to obtain high purity vanillin product. The process is simple, high in yield and environment friendly, and the obtained vanillin product has high quality.

Description

technical field [0001] The invention relates to a method for preparing vanillin by non-catalytic hydrolysis of coniferaldehyde in a near-critical water medium. Background technique [0002] Vanillin, also known as vanillin, chemical name: 3-methoxy-4-hydroxybenzaldehyde, has vanilla aroma and rich milky aroma, is the largest variety in the fragrance industry, and is widely used in food, daily chemicals, tobacco, etc. It is widely used as a fragrance raw material, flavoring agent or fixative in industry. At the same time, vanillin is also an important pharmaceutical intermediate, which is used to synthesize the drug L-dopa for the treatment of Parkinson's and the drug papaverine for the treatment of heart disease. In addition, vanillin can also be used as a defoamer for lubricating oil, a brightener for electroplating, a conductive agent for printed circuit boards, and a deodorant for rubber. Attractants for pesticides and insecticides, etc. At present, the preparation met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/58C07C27/18
Inventor 吕秀阳孙辉
Owner ZHEJIANG UNIV
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