Method for preparing hexane diacid by liquid-phase catalytic oxidation of cyclohexanol

A technology of liquid-phase catalysis and ring oxidation, which is applied in the production of adipic acid, chemical instruments and methods, and the preparation of organic compounds, etc. It can solve the problems such as the decline in the yield of adipic acid, and meet the requirements of low reaction energy consumption and reaction equipment Low, the effect of low reaction temperature

Inactive Publication Date: 2008-11-12
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it can be clearly seen that the yield of adipic acid drops significantly when no phase transfer agent and additives are used [Applied Chemistry, 2003, 20(6): 570-573]

Method used

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  • Method for preparing hexane diacid by liquid-phase catalytic oxidation of cyclohexanol
  • Method for preparing hexane diacid by liquid-phase catalytic oxidation of cyclohexanol
  • Method for preparing hexane diacid by liquid-phase catalytic oxidation of cyclohexanol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of phosphomolybdovanadic acid:

[0029] 3.58g Na 2 HPO 4 12H 2 O dissolved in 50mL distilled water, 24.2g Na 2 MoO 4 2H 2 O was dissolved in 60mL distilled water, the two solutions were mixed, heated to boiling, and reacted for 30min; then 1.58g NaVO 3 2H 2 O was dissolved in 20mL of distilled water, and the solution was added to the above mixture under stirring, and reacted at 90°C for 30min; stop heating; add 1:1 H while stirring 2 SO 4 until the pH of the solution = 2.0, and continue to stir to room temperature, add 50mL ether to the mixture, shake it well, then add 1:1H 2 SO 4 Continue to vibrate until the solution is divided into three layers after standing still, and the bright red oil in the middle layer is heteropolyacid ether compound. The middle layer was taken, and ether was removed under vacuum at room temperature to obtain 16.4 g of phosphomolybdenum-vanadate.

[0030] According to the above method steps, 1.58g NaVO 3 2H 2 O is repl...

Embodiment 2

[0035] In a 100mL three-necked flask equipped with magnetic stirring and a reflux condenser, add 4.5g (45mmol) of cyclohexanol, 30% H 2 o 2 Oxidant 25mL, heating up to 60°C, adding 0.2g of phosphotungstic acid 1-butyl-3-methylimidazolium salt ([bmim] 3 PW 12 o 40 ) catalyst, stirring reaction 5h. After filtration, the filtrate was cooled to -5°C and kept for 12 hours. Then filter, and vacuum-dry the solid at room temperature for 2 hours to obtain 0.7 g of a white crystalline adipic acid product with a purity of 98% and a yield of adipic acid of 10.15%.

Embodiment 3～6

[0037] The 1-butyl-3-methylimidazolium phosphotungstate catalyst described in Example 2 was replaced by different imidazolium salt heteropolyacids, and other conditions were the same as in Example 2. The test results are listed in Table 1.

[0038] Table 1

[0039]

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Abstract

The invention provides a method for preparing adipic acid through liquid-phase catalytic oxidation of cyclohexanol. H2O2 is taken as oxidant, a heteropoly acid imidazole salt is taken as catalyst, the cyclohexanol undergoes the catalytic oxidation to prepare the adipic acid, the catalyst can be phosphotungstic acid 1-butyl-3-methylimidazolium bmim3PW12O40, phosphomolybdic acid 1-butyl-3-methylimidazolium bmim3PMo12O40, and molybdovanadophosphoric heteropolyacid 1-butyl-3-methylimidazolium bmim3+xPMo12-xVxO40 (x is equal to between 1 and 3) and so on, and the bmim represents a 1-butyl-3-methyl-imidazolium cation. Compared with the method of preparing the adipic acid by industrially using nitric acid (nitrate) to oxidize the cyclohexanol, the method can not produce poisonous oxynitride N2O, and avoids the harm to the environment; and in a reaction system, phase shift catalyst and addition agent are not used, which avoids the potential environmental pollution and has apparent economic and social significance.

Description

(1) Technical field [0001] The invention relates to a method for preparing adipic acid by liquid-phase catalytic oxidation of cyclohexanol, especially a method of using H 2 o 2 A method for preparing adipic acid by catalyzing the oxidation of cyclohexanol as an oxidizing agent and heteropolyacid 1-butyl-3-methylimidazolium salt as a catalyst. (2) Background technology [0002] Adipic acid is an important intermediate in organic synthesis. It has the general properties of aliphatic dibasic acids, and can undergo salt-forming reactions, esterification reactions, amidation reactions, etc., and can be polycondensed with diamines to form high-molecular polymers. . Adipic acid is mainly used in the production of fibers and engineering plastics, and is also used in the production of various esters, most of which are used as plasticizers, and a small part is used as high-grade lubricants. The most important use of adipate polyesters is in the production of polyurethane elastomers...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/285C07C55/14B01J31/02
CPCY02P20/30
Inventor 施介华潘高
Owner ZHEJIANG UNIV OF TECH
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