Method for preparing acetosyringone and vanillyl ethyl ketone by oxidizing lignin

A technology of acetosyringone and vanilla ethyl ketone, which is applied in the field of preparation of fine chemicals, can solve the problems of high price, difficulty in preparing vanillyl ethyl ketone and aceto syringone, etc., and achieve the effects of reducing hazards and simplifying reaction steps

Inactive Publication Date: 2011-12-28
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention aims at the problems of difficult preparation and high price of vanillyl ethyl ketone and acetosyringone, and provides a method for

Method used

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  • Method for preparing acetosyringone and vanillyl ethyl ketone by oxidizing lignin
  • Method for preparing acetosyringone and vanillyl ethyl ketone by oxidizing lignin
  • Method for preparing acetosyringone and vanillyl ethyl ketone by oxidizing lignin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 20 mass parts of alkali lignin and 1.2 mass parts of p-nitrobenzoic acid oxidizing agent are stirred uniformly in the sodium hydroxide solution of 2.5mol / L in 200 mL concentration; o C under reaction 5h. The lignin used in addition to alkali lignin can also be one or more of lignin sulfonate, organic solvent lignin or enzymatic lignin. In addition to p-nitrobenzoic acid, the oxidizing agent can also be any of 3,5-dinitrobenzoic acid, 3-nitrosalicylic acid, 5-nitrosalicylic acid or 3,5-dinitrosalicylic acid .

[0032] The reaction liquid was cooled, then acidified to pH 4 with 4 mol / L hydrochloric acid, extracted three times with 250 mL chloroform, combined the extracts and then concentrated by distillation under reduced pressure, the distilled chloroform was recycled, and the concentrate obtained was Crude vanilla ethyl ketone and acetosyringone.

[0033] 10 parts by volume of crude products of vanillyl ethyl ketone and acetosyringone were dissolved in 15 parts by vo...

Embodiment 2

[0035] 20 mass parts of lignosulfonate and 1.2 mass parts of 3,5-dinitrobenzoic acid oxidizing agent are stirred uniformly in the sodium hydroxide solution of 2.5mol / L in 200 mL concentration; o C under reaction 2h. The reaction liquid was cooled, then acidified to pH 4 with 4 mol / L hydrochloric acid, extracted three times with 250 mL chloroform, combined the extracts and then concentrated by distillation under reduced pressure, the distilled chloroform was recycled, and the concentrate obtained was Crude vanilla ethyl ketone and acetosyringone. 10 parts by volume of crude products of vanillyl ethyl ketone and acetosyringone were dissolved in 15 parts by volume of acetone solvent at 40° C., and then separated by three times of recrystallization to obtain vanillyl ethyl ketone and acetosyringone. According to gas chromatography analysis, the separation and purification rates were 96.1% and 97.6%, respectively, and the total yield was 18.1%.

Embodiment 3

[0037]Add 20 parts by mass of lignosulfonate, 0.6 parts by mass of 3,5-dinitrobenzoic acid and 200 mL of 0.5 mol / L sodium hydroxide solution into a 500 mL reactor, stir evenly, at 180 o C for 2 h.

[0038] The reaction liquid was cooled, then acidified to pH 4 with 4 mol / L hydrochloric acid, extracted three times with 250 mL chloroform, combined the extracts and then concentrated by distillation under reduced pressure, the distilled chloroform was recycled, and the concentrate obtained was Crude vanilla ethyl ketone and acetosyringone. 10 parts of the concentrate were dissolved at 60°C with 10 parts of ethanol solvent, and then separated by 4 times of recrystallization to obtain vanillyl ethyl ketone and acetosyringone. According to gas chromatography analysis, the purity was 96.4% and 97.7%, respectively, and the total yield was 18.0 %.

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Abstract

The invention discloses a method for preparing acetovanillone and acetosyringone (AS) through oxidation of lignin by using an oxidizing agent. According to the method, an oxidizing agent reacts with the lignin in an alkaline solution; the resulting reaction solution is subjected to acidification, extraction and concentration to obtain the crude product after completing the reaction; the treatments of recrystallization and rectification are performed to obtain the acetovanillone and the AS. The oxidizing agent is the one selected from p-nitrobenzoic acid, 3,5-dinitrobenzoic acid, 3-nitrosalicylic acid, 5-nitrosalicylic acid or 3,5-dinitrosalicylic acid. According to the present invention, the oxidizing agent has low toxicity, such that the harm to the environment can be reduced; the post-treatment steps are simplified, and the uses of the organic solvents are reduced, such that the secondary pollution to the environment is reduced; the yield is relatively high, the purities of the products are respectively 97.3% and 98.2% through the gas chromatography analysis; the two important chemical raw materials of guaiacol and lilac alcohol can be synchronously obtained when preparing the acetovanillone and the AS.

Description

technical field [0001] The invention belongs to the preparation of fine chemicals, in particular to a method for separating and preparing high-purity acetosyringone and vanillyl ethyl ketone from lignin through oxidation reaction. Background technique [0002] Acetovanillone is also known as Canadian cannabinoid, apocynin, vanilla ethyl ketone, acetyl vanillone, 4'-hydroxy-3'-methoxyacetophenone. Needle crystal, melting point 115°C. The boiling point is 295-300°C. Has a weak vanilla smell. It exists naturally in the root of Apocynum venetum L., the root and stem of Canada hemp (A.cannabinum L.), and can also be prepared by chemical synthesis. Pharmacological experiments have proved that it has choleretic effect on rabbits, contraction effect on rat uterus, and inhibitory effect on frog heart; it also has anti-arthritis and anti-oxidation activities. Acetosyringone (AS), also known as 4'-hydroxy-3',5'-dimethoxyacetophenone, has a melting point of 124-127°C. Stachel et al...

Claims

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Application Information

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IPC IPC(8): C07C49/84C07C45/27
Inventor 周永红杨晓慧刘红军张猛
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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