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Method for preparing aliphatic alcohol from aliphatic carboxylic acid through decarboxylation

A technology of aliphatic carboxylic acid and aliphatic alcohol, which is applied in the field of energy and chemical industry, can solve the problems of complex reaction process and difficult realization, and achieve the effects of reducing reaction energy consumption and raw material consumption, reducing reaction cost, and wide application prospects

Active Publication Date: 2018-10-23
HAINAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The current decarboxylation methods still face many problems: first, they basically need an external hydrogen source or reducing agent; second, the decarboxylation technology requires high energy consumption conditions such as high temperature and high pressure; third, the reaction process is complicated and difficult to realize

Method used

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  • Method for preparing aliphatic alcohol from aliphatic carboxylic acid through decarboxylation
  • Method for preparing aliphatic alcohol from aliphatic carboxylic acid through decarboxylation
  • Method for preparing aliphatic alcohol from aliphatic carboxylic acid through decarboxylation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: A kind of method that benzoic acid is converted into benzyl alcohol

[0028] Step a, add benzoic acid to N-(hydroxyl)phthalimide, 4-dimethylaminopyridine, and dichloromethane in a three-necked flask and mix evenly, then add dicyclohexylcarbodiimide at 25°C After the reaction is completed, the reaction is carried out by washing and purifying to obtain phenyl N-(acyloxy)phthalimide.

[0029] Wherein the molar weight (mol) of benzoic acid in step a: the molar weight (mol) of N-(hydroxyl) phthalimide: the molar weight (mol) of 4-dimethylaminopyridine: the mole of dichloromethane Amount (mol): Molar amount (mol) of dicyclohexylcarbodiimide=1:1.1:0.1:0.1:0.1.

[0030] Step b, dissolving the phenyl N-(acyloxy)phthalimide obtained in step a in the solvent N,N-dimethylformamide in a three-necked flask, adding reducing agents 2, 2, 6 , 6-tetramethylpiperidine nitroxide free radical and 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate, mixed uniformly; In the pr...

proportion Embodiment 2～5

[0034] Proportional examples 2-5: a kind of method that benzoic acid is converted into benzyl alcohol

[0035] Step a and step c process reaction conditions of embodiment 2~5 are consistent with embodiment 1. In step b of Examples 2-5, when other reaction conditions are consistent with Example 1, by adjusting the reducing agent 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate The consumption of acid diethyl ester, the productive rate that benzoic acid decarboxylation is converted into benzyl alcohol is as follows:

[0036]

[0037] Under the same reaction conditions, when the amount of reducing agent 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate diethyl ester was 0.2 mmol, the decarboxylation of benzoic acid was converted into the product of benzyl alcohol The highest rate reached 95%.

Embodiment 8

[0041] Embodiment 8 A kind of method that palmetate is converted into pentadecyl alcohol

[0042] Step a, add hexadecanoic acid to N-(hydroxyl)phthalimide, 4-dimethylaminopyridine, dichloromethane and mix well in a three-necked flask, then add dicyclohexylcarbodiimide at 25°C The reaction is carried out under conditions, and after the reaction is completed, washing and purification are carried out to obtain pentadecyl N-(acyloxy)phthalimide.

[0043] Wherein the molar weight (mol) of hexadecanoic acid in step a: the molar weight (mol) of N-(hydroxyl) phthalimide: the molar weight (mol) of 4-dimethylaminopyridine: dichloromethane Molar weight (mol): molar weight (mol) of dicyclohexylcarbodiimide=1:1.1:0.1:0.1:0.1.

[0044] Step b, dissolve the pentadecyl N-(acyloxy)phthalimide obtained in step a in the solvent N,N-dimethylformamide in a three-necked flask, add reducing agent 2,2, 6,6-tetramethylpiperidine nitroxide radical and 1,4-dihydro-2,6-dimethyl-3,5-pyridine dicarboxylate...

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Abstract

The invention relates to a method for preparing aliphatic alcohol from aliphatic carboxylic acid through decarboxylation. The method comprises the following steps of converting aliphatic carboxylic acid into aliphatic N-(acyl oxy)phthalimide; then, performing photocatalysis decarboxylation reaction to convert the material into aliphatic N-(oxy)2, 2,6,6-tetramethylpiperidine nitrogen-oxygen free radicals; finally, reducing the materials into aliphatic alcohol. The method provided by the invention has the advantages that good chemical selectivity is realized; the wide and easy-to-obtain materialsources are realized. The defects of harsh reaction conditions and high energy consumption such as high temperature and high pressure of aliphatic carboxylic acid conversion by a conventional heat conversion method are avoided; the reaction process is simple and convenient; the operation is easy; the repeated extraction is avoided; in addition, the additional introduction of high-purity hydrogengas is not needed; the reaction energy consumption and the raw material consumption are greatly reduced; the green and environment-friendly effects are achieved; the environment pollution is small; the wide application prospects are realized.

Description

technical field [0001] The invention relates to the technical field of energy and chemical industry, in particular to a method for preparing fatty alcohol by decarboxylation of fatty carboxylic acid. Background technique [0002] With the rapid consumption of fossil resources, more and more attention has been paid to the development and utilization of renewable clean energy. Biomass is an important renewable energy, and it is the only renewable organic carbon source, which can provide abundant organic carbon resources. Biomass is the only source that can be converted into liquid fuels and is an alternative to fossil fuels. [0003] Carboxylic acids are an important class of biomass platform molecules, which are widespread in nature, stable in nature, and low in toxicity. Decarboxylation of carboxylic acids can provide a route to convert fatty carboxylic acids into fatty alcohols. Therefore, the use of photocatalysis to convert fatty carboxylic acids into more valuable alc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48C07D211/94C07C29/00C07C33/22C07C31/125
CPCC07C29/00C07C31/125C07C33/22C07D209/48C07D211/94
Inventor 郑超李小宝陈光英王玉婷徐杨蕊王煜
Owner HAINAN NORMAL UNIV
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