Method for preparing adipic acid through co-catalytic oxidation of six-carbon oxygenated compound and cyclohexane

A technology of cyclohexane and compound, applied in the field of preparation of adipic acid, can solve the problems of difficult catalyst recovery, environmental pollution, harsh reaction conditions and the like

Active Publication Date: 2013-08-21
上海立科化学科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Not only is the recovery of the catalyst difficult and the cost of the catalyst is high, but also a large amount of metals and additives crystallize out together with adipic acid, which makes the subsequent processing of the product complicated and difficult

Method used

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  • Method for preparing adipic acid through co-catalytic oxidation of six-carbon oxygenated compound and cyclohexane
  • Method for preparing adipic acid through co-catalytic oxidation of six-carbon oxygenated compound and cyclohexane
  • Method for preparing adipic acid through co-catalytic oxidation of six-carbon oxygenated compound and cyclohexane

Examples

Experimental program
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Effect test

Embodiment 1

[0072] Add 600g cyclohexane and 200g solvent acetic acid in a 1.2L batch oxidation reactor, and add 0.6mg metal phthalocyanine (R with general formula (IV) structure 1 = H, R 2 =CH 3 CH 2 , M=Co) as the catalyst, 36g of cyclohexyl hydroperoxide as the co-oxidant, and then 1.2MPa of oxygen was continuously fed into the reactor to maintain the pressure in the reactor at 1.0MPa and the temperature at 153°C to continuously stir the reactants, and stop after 3.5 hours Reaction to obtain the reaction product, cooling, crystallization, filtration and washing to obtain the adipic acid product. The analysis results of gas chromatography and liquid chromatography showed that the conversion rate of cyclohexane was 17.6%, and the selectivity of adipic acid in the final oxidation product diacid was 93.2%.

Embodiment 2

[0074] Add 600g cyclohexane and 200g solvent acetic acid in a 1.2L batch oxidation reactor, and add 5.4mgMnO 2 As a catalyst, 18g of cyclohexyl hydroperoxide is used as a co-oxidant, and then 0.75MPa of oxygen is continuously introduced to maintain the internal pressure of the reactor at 0.6MPa and the temperature at 125°C to continuously stir the reactants. After 4 hours, the reaction was stopped to obtain a reaction product, which was cooled, crystallized, filtered and washed to obtain adipic acid product. The analysis results of gas chromatography and liquid chromatography showed that the conversion rate of cyclohexane was 14.8%, and the selectivity of adipic acid in the final oxidation product diacid was 91.4%.

Embodiment 3

[0076] Add 600g hexanaphthene and 200g solvent acetic acid in a 1.2L batch oxidation reactor, and add 4.8mg metalloporphyrin (R with general formula (I) structure 1 =R 2 =R3 =H, M=Co) as the catalyst, 18g of cyclohexyl hydroperoxide as the co-oxidant, and then 0.75MPa of oxygen was continuously introduced, and the reactants were continuously stirred under the conditions of maintaining the pressure in the reactor at 0.6MPa and the temperature at 125°C. After 4 hours, the reaction was stopped to obtain a reaction product, which was cooled, crystallized, filtered and washed to obtain adipic acid product. The analysis results of gas chromatography and liquid chromatography showed that the conversion rate of cyclohexane was 13.8%, and the selectivity of adipic acid in the final oxidation product diacid was 88.6%.

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Abstract

The invention discloses a method for preparing adipic acid through co-catalytic oxidation of a six-carbon oxygenated compound and cyclohexane. According to the method, cyclohexane is used as a raw material, a six-carbon oxygenated compound is used as a co-oxidant, and one of transitional metal salt or oxide, N-hydroxyphthalimide and analogues, metal phthalocyanine and metalloporphyrin, or a mixture of several ones thereof is used as a catalyst, the mass ratio of the six-carbon oxygenated compound to the cyclohexane is (0.003-9):1, and the dosage of the catalyst is 1-100,000ppm of the total weight of the cyclohexane; and under the conditions that an oxygen-containing gas is continuously introduced, the reaction temperature is 80-155 DEG C, the reaction pressure is 0.1-1.2MPa and the reaction time is 0.4-4 hours, the cyclohexane is oxidized into adipic acid in a solvent in one step. The method disclosed by the invention has the advantages of mild reaction conditions, high once through yield of product, good selectivity and environmental protection.

Description

technical field [0001] The invention relates to a method for preparing adipic acid, in particular to a method for preparing adipic acid by co-catalyzing oxidation of a six-carbon oxygen-containing compound and cyclohexane. Background technique [0002] Adipic acid is an important basic raw material for the nylon and polyurethane industries, as well as an intermediate for many lubricating oil additives. At present, the industrial production of adipic acid mainly uses cyclohexane as the starting material, and produces adipic acid through a two-step process. The first step uses air to oxidize cyclohexane to cyclohexanol and cyclohexanone (KA oil), and the second step uses nitric acid to oxidize KA oil to adipic acid. This route accounts for about 93% of the global total production capacity. Its reaction process is as follows: [0003] [0004] The first step process of the above route often uses a homogeneous cobalt-based catalyst or does not add a catalyst. During the rea...

Claims

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Application Information

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IPC IPC(8): C07C55/14C07C51/215
Inventor 王勤波夏仲平舒文晓毛炳炎叶翔董阳军
Owner 上海立科化学科技有限公司
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