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Method for producing epoxy cyclohexane

A technology of epoxycyclohexane and production method, applied in the direction of organic chemistry, etc., can solve the problems of low utilization rate, low reaction yield, large consumption of aldehydes, etc.

Inactive Publication Date: 2004-11-03
BALING PETRO CHEM CO LTD SINOPEC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Hypochlorous acid oxidation method yield is low, and productive rate is only 70~73%, and three wastes are many ["Fine Organic Chemical Materials and Intermediates Handbook", Chemical Industry Press, 1992]; Hydrogen peroxide oxidation method will use phase transfer catalyst and solvent, hydrogen peroxide utilization rate is 87.6%, epoxycyclohexane selectivity is 93.7% [CN1355067A], there is hydrogen peroxide use safety problem in this method; Catalyzed oxidation method, wherein the best effect is "application molecular oxygen / n-valeraldehyde / Studies on Cyclohexene Oxidation of Cobalt Trioxide System "[1999.11], high aldehyde-ene ratio (aldehyde:ene=3:1, molar ratio) is used in this process, and the consumption of aldehyde is large , the utilization rate is not high
And similar process conditions are used for low aldehyde-ene ratio (aldehyde: alkene is less than 1: 1.5) reaction yield is very low (less than 50%)

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0019] Example 1 uses molybdenum trioxide-cobalt trioxide-phosphoric acid as a catalyst, and the experimental results are shown in Table 1.

[0020] Put 500g of cyclohexene, 90g of isobutyraldehyde, 7.8g of molybdenum trioxide, 2.2g of dicobalt trioxide, and 0.5g of 98% phosphoric acid into a four-neck flask with reflux condenser and stirring, control the temperature at 45°C, and pass oxygen under stirring , control the oxygen flow rate to 40L / h, and react for 6 hours.

example 2

[0021] Example 2 uses molybdenum trioxide-manganese dioxide-nitric acid as a catalyst, and the experimental results are shown in Table 1.

[0022] Add 500 g of cyclohexene, 150 g of isovaleraldehyde, 6.2 g of molybdenum trioxide, 1.2 g of manganese dioxide, and 0.5 g of 65% nitric acid into a four-necked flask with reflux condenser and stirring. Control oxygen flow to be 20L / h, react for 8 hours.

example 3

[0023] Example 3 uses tungsten trioxide-ferric oxide-arsenic acid as a catalyst, and the experimental results are shown in Table 1.

[0024] Put 500g of cyclohexene, 60g of n-valeraldehyde, 7g of tungsten trioxide, 3.2g of ferric oxide, and 0.5g of 95% arsenic acid into a four-neck flask with reflux condenser and stirring, control the temperature at 60°C, and pass oxygen under stirring , control the oxygen flow rate to 30L / h, and react for 4 hours.

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PUM

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Abstract

The epoxy cyclohexane producing process includes using cyclohexene as main material, molecular oxygen as oxygen source, n-valeraldehyde or isovaleraldehyde or isobutylaldehyde as intermediate; adopting re-compounded catalyst including at least one oxide of Mn, Fe, Co and Ni, at least one oxide of Mo and W, and at least one oxo acid of N, P and As; and reaction at 30-80 deg.c for 2-12 hr. The re-compounded catalyst can oxidize aldehyde into per-acid in high selectivity and catalyze the reaction between per-acid with cyclohexene in high selectivity to obtain epoxy cyclohexane as the destination product in the same reactor, with the single-path cyclohexene converting rate reaching 23 % and selectivity reaching 98 %. The reaction process uses no solvent and the metal oxide in the re-compounded catalyst may be reused.

Description

technical field [0001] The invention relates to a production method of epoxycyclohexane. Background technique [0002] Due to the very active epoxy group in the molecular structure of epoxy cyclohexane, it can react with ammonia, amine, phenol, alcohol, carboxylic acid, etc. to generate a series of high value-added compounds, so it is an important Organic synthesis intermediates with a wide range of uses, such as the synthesis of a new type of pesticide, decimate; unsaturated resins with high hardness, high temperature resistance, and acid and alkali resistance; photosensitive materials; polycarbonate; adipaldehyde, etc. [0003] At present, the methods for preparing epoxycyclohexane from cyclohexene epoxidation mainly include: hypochlorous acid oxidation method, hydrogen peroxide oxidation method and catalytic oxidation method. Hypochlorous acid oxidation method yield is low, and productive rate is only 70~73%, and three wastes are many ["Fine Organic Chemical Materials an...

Claims

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Application Information

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IPC IPC(8): C07D301/04
Inventor 陈子明陈保兴刘霞许丽娟
Owner BALING PETRO CHEM CO LTD SINOPEC
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