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Method for preparing Guerbet acids by taking malonate as raw material

A technology of malonate and alkyl malonate, which is applied in the field of Guerbet acid preparation technology, can solve the problems that have not been reported in the literature, the reaction is difficult, and the corrosion is large, so as to avoid the reaction difficulty and be easy to operate , the effect of high yield

Inactive Publication Date: 2017-05-31
SHANGHAI ADVANCED RES INST CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the chemical process, the oxidation reaction has technical defects such as difficult reaction, large corrosion and serious pollution.
Other methods for preparing Guerbet acids without oxidation of Guerbet alcohols have not been reported in the literature

Method used

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  • Method for preparing Guerbet acids by taking malonate as raw material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Under nitrogen protection, put 100g of diethyl malonate and 300mL of absolute ethanol into a 1000mL three-necked round-bottomed flask, add 40.5g of sodium methoxide at room temperature, then slowly add 102.8g of bromobutane, and heat up after the addition Reflux and react for 3 hours; cool down to room temperature, then add 40.5g of sodium methoxide, then slowly add 102.8g of bromobutane, and heat up and reflux for 3 hours. Cool down to room temperature, remove the solvent, add 1mol / L sulfuric acid aqueous solution to neutralize the system until the pH value is about 7, wash the organic phase with water, and distill under reduced pressure to obtain diethyl dibutylmalonate, 154g (90.6% yield).

[0025] Take 100g diethyl dibutylmalonate, 550mL sodium hydroxide aqueous solution (the concentration of sodium hydroxide is 4mol / L), and 100mL ethanol were added to a 1000mL round bottom flask, heated to reflux for 12h, cooled to room temperature, and added 4mol / L Sulfuric acid w...

Embodiment 2

[0028] Under nitrogen protection, put 100g of diethyl malonate and 300mL of absolute ethanol into a 1000mL three-necked round-bottomed flask, add 40.5g of sodium methoxide at room temperature, then slowly add 102.8g of bromobutane, and heat up after the addition Reflux and react for 3 hours; cool down to room temperature, then add 40.5g of sodium methoxide, then slowly add 91.2g of chloro-n-hexane, heat up and reflux for 3 hours. Cool to room temperature, remove solvent, add 1mol / L sulfuric acid aqueous solution and neutralize system to about pH value 7, organic phase washing, underpressure distillation obtain 2-butyl-2-hexyldiethyl malonate, 167g (productivity 89.1%).

[0029] Take 100g of diethyl 2-butyl-2-hexylmalonate, 500mL of sodium hydroxide aqueous solution (4mol / L), and 100mL of ethanol into a 1000mL round bottom flask, heat to reflux for 12h, cool down to room temperature, and add 4mol / L Sulfuric acid adjusted the pH value to about 1.9, left standing, the upper laye...

Embodiment 3

[0032] Under the protection of nitrogen, put 100g of diethyl malonate and 300mL of absolute ethanol into a 1000mL three-necked round-bottomed flask, add 40.5g of sodium methoxide at room temperature, then slowly add 91.2g of chloro-n-hexane, and then raise the temperature to reflux , reacted for 3h; cooled down to room temperature, then added 40.5g of sodium methoxide, then slowly added 91.2g of chloro-n-hexane, heated to reflux for 3h. Cool down to room temperature, remove the solvent, add 1mol / L sulfuric acid aqueous solution to neutralize the system to a pH value of about 7, wash the organic phase with water, and distill under reduced pressure to obtain diethyl dihexylmalonate, 184g (89.7% yield).

[0033]Take 100g diethyl dihexylmalonate, 450mL aqueous sodium hydroxide solution (4mol / L), and 100mL ethanol into a 1000mL round bottom flask, heat to reflux for 12h, cool down to room temperature, add 4mol / L sulfuric acid to adjust the pH value to 1.9 Left and right, stand stil...

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Abstract

The invention discloses a method for preparing Guerbet acids by taking malonate as a raw material. The method comprises the following steps: using the malonate as the raw material, and carrying out alkylation reaction under the action of alkali to obtain dialkyl malonate; sequentially carrying out hydrolysis reaction and decarboxylic reaction on obtained dialkyl malonate to obtain the Guerbet acid, wherein the malonate is dimethyl malonate or diethyl malonate; the alkali of the alkylation reaction is selected from one or more of potassium carbonate, sodium hydroxide, potassium hydroxide, sodium methylate and sodium ethoxide; an alkylating reagent is haloalkane with 2 to 20 carbons. According to the method disclosed by the invention, the Guerbet acids are prepared by taking the malonate as the raw material for the first time; related three reactions are easily operated, high temperature or high pressure is not needed, and high yield is realized; by means of the alkylation reaction disclosed by the invention, a main chain structure and a branched chain structure of the Guerbet acids can be flexibly regulated and controlled, and further the Guerbet acids with different properties are obtained.

Description

technical field [0001] The invention relates to the technical field of preparation technology of Guerbet acid, in particular to a method for preparing Guerbet acid by using malonate as raw material. Background technique [0002] Guerbet acid is a fatty acid with a longer branched alkane at the α-position of the carboxylic acid. Compared with straight-chain fatty acids with the same carbon number, it is colorless and odorless, has almost no adverse effects on the human body, low freezing point, and low irritation. It is used in industrial lubricants, metal processing fluids, cosmetics, surfactants and additives, etc. has a wide range of applications. [0003] Guerbet acids are generally prepared by oxidation of Guerbet alcohols. The Guerbet reaction is a reaction in which alcohol-alcohols condense to form higher alcohols. Guerbet alcohols are both the product of this reaction and the source of the name of this type of alcohol. The name Guerbet acid is derived from this. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/38C07C53/128
CPCC07C67/343C07C51/09C07C51/38C07C69/34C07C55/02C07C53/128
Inventor 江泱李久盛许健
Owner SHANGHAI ADVANCED RES INST CHINESE ACADEMY OF SCI
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