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Application of tris(2,2'-bipyridyl)ruthenium(II) chloride hexahydrate as catalyst

A technology of hexahydrate and trichloride, applied in the direction of organic compound/hydride/coordination complex catalyst, physical/chemical process catalyst, catalytic reaction, etc. The effect of reaction cost, reduction of reaction energy consumption and raw material consumption, and broad application prospects

Inactive Publication Date: 2018-10-26
HAINAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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
At present, there is no report of tris(2,2'-bipyridyl)ruthenium(II) chloride hexahydrate as a catalyst for the preparation of fatty alcohols from fatty acids

Method used

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  • Application of tris(2,2'-bipyridyl)ruthenium(II) chloride hexahydrate as catalyst
  • Application of tris(2,2'-bipyridyl)ruthenium(II) chloride hexahydrate as catalyst
  • Application of tris(2,2'-bipyridyl)ruthenium(II) chloride hexahydrate as catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Application of three (2,2'-bipyridyl) ruthenium (II) chloride hexahydrate as a catalyst in the preparation of benzyl alcohol from benzoic acid decarboxylation

[0026] 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.

[0027] 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.

[0028] 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 radical ...

proportion Embodiment 4～7

[0035]Ratio Examples 4-7: Application of tris(2,2'-bipyridyl)ruthenium(II) chloride hexahydrate as a catalyst in the preparation of benzyl alcohol by decarboxylation of benzoic acid

[0036] Step a and step c process reaction conditions of embodiment 4~7 are consistent with embodiment 1. In step b of Examples 4-7, 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:

[0037]

[0038] 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

[0039] Example 8 Application of tris(2,2'-bipyridyl)ruthenium(II) chloride hexahydrate as a catalyst in the decarboxylation of hexadecanoic acid to prepare pentadecyl alcohol

[0040] 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.

[0041] 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.

[0042] 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-tetrame...

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Abstract

The invention relates to application of tris(2,2'-bipyridyl)ruthenium(II) chloride hexahydrate as a catalyst for preparing fatty alcohol through decarboxylation of aliphatic carboxylic acid. The application has the advantages that chemical selectivity is high, and materials are extensive and easy to acquire; defects in aliphatic carboxylic acid conversion based on conventional thermochemical methods, including high energy consumption such as high temperature and high pressure, and harsh reaction conditions, are avoided; the reaction process is simple, convenient, and easy to operate, and repeated extraction is avoided; additional injection of high-purity hydrogen is not needed, and reaction energy consumption and raw material consumption are greatly reduced; environment protection is realized, and environment pollution is small; a wide application prospect is achieved.

Description

technical field [0001] The invention relates to the technical field of energy and chemical engineering, in particular to the application of tris(2,2'-bipyridyl)ruthenium(II) chloride hexahydrate as a catalyst in the decarboxylation of fatty carboxylic acids to prepare fatty alcohols. 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. 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. The current decar...

Claims

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Application Information

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IPC IPC(8): B01J31/22C07C29/132C07C31/125C07C33/22
CPCB01J31/1815B01J2231/64B01J2531/0213B01J2531/828C07C29/132C07D209/48C07D211/94C07C33/22C07C31/125
Inventor 郑超李小宝郑彩娟陈光英王玉婷徐杨蕊魏俊杰
Owner HAINAN NORMAL UNIVERSITY
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