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Methyl esterification method of low-toxicity rosin-resin acid

A technology of rosin resin acid and rosin resin, which is applied in chemical instruments and methods, carboxylate preparation, organic chemistry, etc., can solve the problems of low reaction yield, high toxicity, and few side reactions, and achieve high yield and low toxicity. The effect of low cost and easy availability of raw materials

Active Publication Date: 2016-06-29
GUANGXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a method for the methyl esterification of rosin resin acid with low toxicity, thereby overcoming the shortcomings of low reaction yield and high toxicity in the process of methyl esterification of rosin resin acid in the prior art, and obtaining a method with high yield A method for rosin resin acid methylation with few side reactions, safety and low toxicity

Method used

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  • Methyl esterification method of low-toxicity rosin-resin acid

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Synthesis of methyl abietic acid:

[0024] Taking abietic acid as raw material, its reaction formula is as follows:

[0025]

[0026] In the reaction formula, I is abietic acid, II represents dimethyl carbonate, and III is the product methyl abietic acid. In the 250mL three-neck flask equipped with stirrer, thermometer and reflux condenser, add 30mL organic solvent DMF, then add abietic acid (0.05mol, 15.0g) and methylation reagent dimethyl carbonate C 3 h 6 o 3 (0.5mol, 45.0g), alkali catalyst lithium hydroxide LiOH·H 2 O (0.1mol, 4.2g), make abietic acid, dimethyl carbonate, lithium hydroxide dissolve in DMF, under the protection of nitrogen, in 100 ℃ of oil baths, be heated to stable reflux, namely when the number of reflux drops in the three-necked bottle is 1 to 2 drops / second is stable, and the stable reflux temperature is 93°C. The progress of the reaction was tracked by thin-layer chromatography every 1 hour until it was detected that there was no reacti...

Embodiment 2

[0034] Synthesis of methyl abietic acid:

[0035] Taking abietic acid as raw material, its reaction formula is as follows:

[0036]

[0037] In the reaction formula, I is abietic acid, II represents dimethyl carbonate, and III is the product methyl abietic acid.

[0038] In the 250mL three-neck flask equipped with stirrer, thermometer and reflux condenser, add 30mL organic solvent DMF, then add abietic acid (0.05mol, 15.0g) and methylation reagent dimethyl carbonate C 3 h 6 o 3 (0.75mol, 67.5g), alkali catalyst potassium carbonate K 2 CO 3 (0.1 mol, 13.8 g). Dissolve abietic acid, dimethyl carbonate, and potassium carbonate in DMF, and heat it in an oil bath at 118°C under the protection of nitrogen to a stable reflux, that is, when the number of reflux drops in the three-necked bottle is 1 to 2 drops / second, it is stable. The stable reflux temperature, ie, the reflux temperature, was 110°C. The progress of the reaction was tracked by thin-layer chromatography every ...

Embodiment 3

[0041] Synthesis of methyl abietic acid:

[0042] Taking abietic acid as raw material, its reaction formula is as follows:

[0043]

[0044] In the reaction formula, I is abietic acid, II is dimethyl carbonate, and III is the product methyl abietic acid.

[0045] In a 250mL three-neck flask equipped with a stirrer, a thermometer and a reflux condenser, add 100mL of organic solvent acetone, then add abietic acid (0.05mol, 15.0g) and methyl esterifying reagent dimethyl carbonate C 3 H 6 O 3 (1.5mol, 135g), alkali catalyst potassium carbonate K 2 CO 3 (0.1 mol, 13.8 g). Abietic acid, dimethyl carbonate and potassium carbonate were dissolved in acetone, and heated to a stable reflux in an oil bath at 75°C under nitrogen protection, that is, when the number of reflux drops in the three-necked flask was 1 to 2 drops / second, it was stable. The stable reflux temperature, that is, the reflux temperature, was 68°C. The progress of the reaction was tracked by thin-layer chromatog...

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Abstract

The invention discloses a methyl esterification method of low-toxicity rosin-resin acid, comprising the following steps: mixing rosin-resin acid and methyl esterification reagent dimethyl carbonate, dissolving in an organic solvent, and reflux reacting at 68-110 DEG C in the presence of a base catalyst for 24-72 h to obtain methyl rosinate-resinate. The methyl rosinate-resinate prepared by the method has yield up to 99.6%, the method has the advantages that materials are easy to obtain, the preparation process is safe, the materials are low in toxicity, and reacting is easy to control and post-treatment is simple and easy.

Description

technical field [0001] The invention relates to a methyl esterification method of rosin resin acid, in particular to a method for methyl esterification of low toxicity rosin resin acid. Background technique [0002] The natural rosin-based resin acid compound is a kind of natural product containing various components and has a wide range of physiological activities, and has medicinal application value. Abietic acid, as the main component of rosin (its content is about 30-40%), can kill a variety of microorganisms, such as microorganisms such as Gram-positive bacteria and fungi, has excellent anti-inflammatory activity, and can also adjust lipid metabolism and treat Atherosclerosis, abietic acid can also be used as an anticonvulsant drug. Dehydroabietic acid is also one of the components of rosin, which is derived from the dehydrogenation isomerization of abietic acid. It also has good biological activity and is considered to be an anti-nicotine substance in vivo and in vitr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/11C07C69/753
CPCC07C67/11C07C69/753
Inventor 张敏向佩莫静蓝擎张岩
Owner GUANGXI UNIV
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