Method for preparing 1,2-cyclohexanediol by catalytic oxidation of cyclohexene

Abstract

The invention belongs to the glycol preparation technique field through the olefin selective oxidation. The invention aims to provide a method for preparing a 1, 2-cyclohexanediol through the cyclohexene catalytic oxidation. The method for preparing the 1, 2-cyclohexanediol of the invention comprises weighting and putting a given amount of cyclohexene, catalyst, solvent and oxidizing agent in a container for reaction, agitation is needed in the process of reaction, a reaction mixture is obtained after the reaction, and the obtained reaction mixture produces the 1, 2- cyclohexanediol through separation. In the invention, the adopted catalyst is a metal oxide, the solvent is a toluene and the oxidizing agent is a tert-butyl hydroperoxide. The method of preparation has advantages of avoiding the problem of high volume of wastewater in the hydroperoxide process of formic acid, hydogen peroxide or acetic acid when being used previously, reducing the production cost, further simplified technical process and non harm to the human body of the adopted catalyst, and is an environment-friendly chemical reaction. The method has a simple device and practical and easy process, and is easy for forming the industrial scale.

Description

technical field [0001] The invention belongs to the technical field of diol preparation by olefin selective oxidation. Background technique [0002] 1,2-Cyclohexanediol is a very important raw material for organic synthesis, which can be used to prepare various organic intermediates, mainly used in industries such as medicine, pesticide, rubber additives, plasticizers and liquid crystal materials, and is also an epoxy The raw material of high-grade resin diluent can also be used for dehydrogenation to prepare catechol, which has a wide range of uses. As early as 1936, Criegee et al. (Ber., 69, 2753 (1936)) prepared 1,2-cyclohexanediol by hydrolysis of epoxycyclohexane. In 1945, Swern et al. (J.Am.Chem.Soc., 67, 1786 (1945)) used hydrogen peroxide as an oxidant and formic acid as an oxygen carrier, and directly oxidized cyclohexene to prepare 1,2-cyclohexanediol , the yield is 65~73%. In 1949, Mugdan et al. (J.Chem.Soc., 1949, 2988) used tungsten trioxide as a catalyst and...

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Problems solved by technology

Tanaka et al. (U.S.Pat.20050096480) used hydrogen peroxide to oxidize cyclohexene to prepare cyclohexanediol in the presence of a polymer containing sulfonic acid groups, and the yield can reach 98%. The yield of this method is very high, and the patent is It is introduced that the high polymer can be recycled, which is an ideal route for the synthesis of cyclohexanediol, but the high polymer products used in the process are expensive and the preparation cost is high

[0003] Because above-mentioned existing preparation 1, the method for 2-cyclohexanediol mostly adopts formic acid or peracetic acid etc. as oxygen carrier, hydrogen peroxide is as oxygenant, and the catalyzers such as bismuth, tungsten and quaternary ammonium salt used in the preparation process and High polymers containing sulfonic acid groups are expensive, so there is a large amount of waste water generated during the preparation process, the steps are cumbersome, the process is complicated, and the disadvantages of high cost affect the industrial production of this product

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