Method for preparing 1,2-cyclohexanediol through carrying out catalytic oxidation on cyclohexene by using phase transfer catalyst

A technology of catalytic oxidation and cyclohexanediol, applied in hydroxyl addition preparation, organic chemistry, etc., can solve the problems of difficult separation and recovery, high production cost, and large consumption of ionic liquid, achieve good application prospects, and reduce combustion and explosion The effect of the danger of separation and the convenience of recycling

Active Publication Date: 2015-02-18
BEIJING RISUN TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the yield and selectivity of 1,2-cyclohexanediol in this method are very high, expensive ionic liquid is used as catalyst and solvent, the ionic liquid consumes a lot, separation and recovery are difficult, and the production cost is relatively high.

Method used

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  • Method for preparing 1,2-cyclohexanediol through carrying out catalytic oxidation on cyclohexene by using phase transfer catalyst
  • Method for preparing 1,2-cyclohexanediol through carrying out catalytic oxidation on cyclohexene by using phase transfer catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Preparation of quaternary ammonium octyl trimethyl decapolytungstate:

[0021] Weigh 32.95g of sodium tungstate and add it into a beaker filled with 100mL of water to dissolve, stir magnetically at 60°C, adjust its pH to about 2 with 3mol / L hydrochloric acid, then slowly add 10.02g of Octyltrimethylammonium bromide in 10mL ethanol solution, the solution immediately appears white turbid. After the dropwise addition, the reaction was continued at 90°C for 0.5h. After the reaction, the white or light yellow solid was obtained by filtration, washed with water and ethanol, and dried in vacuum. The obtained product was detected by an organic elemental analyzer, and it was confirmed that it was the target product. Theoretical value: C=17.38%, H=3.46%, N=1.84%; actual value: C=17.29%, H=3.57%, N=1.81%.

Embodiment 2

[0023] Preparation of butyl trimethyl decapolytungstate quaternary ammonium salt:

[0024] Weigh 33.01g of sodium tungstate and add it into a beaker filled with 100mL of water to dissolve, stir magnetically at 60°C, adjust the pH value to about 2 with 3mol / L hydrochloric acid, then slowly add 7.85g 10mL ethanol solution of butyltrimethylammonium bromide, the solution immediately appeared white turbid. After the dropwise addition, the reaction was continued at 90°C for 0.5h. After the reaction, the white or light yellow solid was obtained by filtration, washed with water and ethanol, and dried in vacuum. The obtained product was detected by an organic elemental analyzer, and it was confirmed that it was the target product. Theoretical value: C=11.94%, H=2.58%, N=1.99%; actual value: C=11.89%, H=2.52%, N=2.03%.

Embodiment 3

[0026] Preparation of hexadecyl trimethyl decapolytungstate quaternary ammonium salt:

[0027] Weigh 32.98g of sodium tungstate and add it into a beaker filled with 100mL of water to dissolve, stir magnetically at 60°C, adjust the pH value to about 2 with 3mol / L hydrochloric acid, then slowly add 14.58g 10mL ethanol solution of cetyltrimethylammonium bromide, the solution immediately appears white turbid. After the dropwise addition, the reaction was continued at 90°C for 0.5h. After the reaction, the white or light yellow solid was obtained by filtration, washed with water and ethanol, and dried in vacuum. The obtained product was detected by an organic elemental analyzer, and it was confirmed that it was the target product. Theoretical value: C=26.16%, H=4.86%, N=1.61%; actual value: C=26.20%, H=4.79%, N=1.58%.

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Abstract

The invention relates to a method for preparing 1,2-cyclohexanediol through carrying out catalytic oxidation on cyclohexene by using a phase transfer catalyst. 1,2-cyclohexanediol is prepared through carrying out catalytic oxidation on cyclohexene by taking quaternary ammonium decatungstate as the phase transfer catalyst, phosphoric acid as a catalyst promoter and hydrogen peroxide as an oxidizing agent. The method has the advantages that toxic and harmful organic solvents such as acetonitrile, methylbenzene and methanoic acid are not used as reaction media, the environment pollution is reduced, the risk of combustion explosion generated in the reaction process is reduced, and large-scale production is easy to realize; the used catalyst, i.e., quaternary ammonium decatungstate, has high catalytic activity; and 1,2-cyclohexanediol is simple in preparation process, convenient to separate and recycle and favorable in application prospect.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular, the invention relates to a method for synthesizing 1,2-cyclohexanediol by catalytic oxidation of cyclohexene. Background technique [0002] 1,2-Cyclohexanediol, referred to as CHD, is a white crystal with the molecular formula C 6 h 12 o 2 , with cis and trans structures, soluble in organic solvents such as methanol and chloroform, and easily soluble in water. Since 1,2-cyclohexanediol has two hydroxyl groups and a ring structure in the molecule, it has relatively active chemical properties and can undergo reactions such as addition, substitution, oxidation, and dehydrogenation. 1,2-cyclohexanediol is an extremely important raw material for organic synthesis, which can be used to synthesize polyester, diacrylate, epoxy resin thinner, catechol, etc. It contains saturated aliphatic rings, which can improve the Thermal stability, widely used in the production of fine chemical pro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C35/14C07C29/04
Inventor 张英伟王耀红周君王翔孙长江
Owner BEIJING RISUN TECH CO LTD
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