Method for producing oxidation product of cycloalkane

一种氧化产物、环烷烃的技术，应用在过氧化合物制备、有机化合物的制备、烃氧化制备含氧化合物等方向，能够解决制备成本增加等问题，达到防止低聚化、减轻负荷、提高生成比的效果

Active Publication Date: 2009-09-30
DAICEL CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This also becomes a reason for the increased production cost of cycloalkanones and cycloalkanols

Method used

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  • Method for producing oxidation product of cycloalkane
  • Method for producing oxidation product of cycloalkane
  • Method for producing oxidation product of cycloalkane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0121] 5% by weight of N-hydroxysuccinyl obtained by adding 80 g (1.14 mol) of cyclopentane and dissolving 100 mg of N-hydroxysuccinimide in a 350 ml SUS316 autoclave equipped with a stirrer at room temperature (25°C) 2 g of imine aqueous solution was sealed in the autoclave, pressurized to 3 MPa (gauge pressure) with a mixed gas of 50% by volume of oxygen and 50% by volume of nitrogen, and stirred at 150° C. for 1 hour. As a result, the cyclopentane of 39mmol reacted (conversion rate 3.4%), and generated 9.4mmol cyclopentanone (selectivity 24.1%), 4.8mmol cyclopentanol (selectivity 12.3%), 12.5mmol cyclopentyl hydroperoxide ( selectivity 32.1%). The overall yield of cyclopentanone, cyclopentanol and cyclopentyl hydroperoxide was 2.3%.

Embodiment 2

[0123] 5% by weight of N-hydroxysuccinyl obtained by adding 80 g (0.95 mol) of cyclohexane and dissolving 100 mg of N-hydroxysuccinimide in a 350 ml SUS316 autoclave equipped with a stirrer at room temperature (25°C) 2 g of imine aqueous solution was sealed in the autoclave, pressurized to 3 MPa (gauge pressure) with a mixed gas of 50% by volume of oxygen and 50% by volume of nitrogen, and stirred at 150° C. for 1 hour. As a result, the cyclohexane of 36mmol reacted (conversion rate 3.8%), generated 9.2mmol cyclohexanone (selectivity 25.6%), 4.6mmol cyclohexanol (selectivity 12.8%), 12.3mmol cyclohexyl hydroperoxide (selectivity rate 34.2%). The overall yield of cyclohexanone, cyclohexanol and cyclohexyl hydroperoxide was 2.7%.

reference example 1

[0132] Example 1 was repeated several times, these reaction liquids were mixed, and the organic phase obtained by liquid separation was separated to obtain a cyclopentyl hydroperoxide-containing liquid used below. The composition of the liquid is as follows: 97.3% by weight of cyclopentane, 0.88% by weight of cyclopentanone, 0.41% by weight of cyclopentyl alcohol, 1.20% by weight of cyclopentyl hydroperoxide, and 0.21% by weight of esters (cyclopentyl esters converted to cyclopentyl esters). Pentanol is 0.12 wt%) and N-hydroxysuccinimide is 13 wtppm.

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Abstract

The present invention discloses a method for commercially producing a corresponding useful oxidation product such as a cycloalkylhydroperoxide, a cycloalkanol and a cycloalkanone, especially a particularly useful cycloalkanone, from a cycloalkane with high selectivity and high yield at low cost. This method is efficient, and advantageous in respect of energy and process. Specifically, an oxidation product of a cycloalkane is obtained by oxidizing the cycloalkane in a liquid-liquid two phase system using an aqueous solvent in the presence of a nitrogen atom-containing cyclic compound which contains a structure represented by the formula (I) below as a constituent and has a solubility in water at 25 DEG C of not less than 0.5 g / 100 g-H2O. (In the formula, X represents an oxygen atom or an -OR group (wherein R represents a hydrogen atom or a protecting group of a hydroxyl group).

Description

technical field [0001] The present invention relates to the preparation method of cycloalkane oxidation reaction product. Among cycloalkyl hydroperoxides, cycloalkanols and cycloalkanones as cycloalkane oxidation reaction products, cycloalkyl hydroperoxides are useful as raw materials for the preparation of cycloalkanols or cycloalkanones. In addition, cycloalkanols are used as Starting materials for the preparation of cycloalkanones are useful. In addition, cycloalkanols and cycloalkanones are useful as raw materials for producing polymer compounds such as polyamide-based polymer compounds, intermediate raw materials for fine chemicals, and the like. Background technique [0002] As a method for producing cycloalkane oxidation products, air oxidation of cycloalkane using a transition metal compound such as a cobalt compound as a catalyst is known (see JP-A-9-143109). However, in general, in this method, the yield of the target oxidation product is low, and if the conversi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C27/12C07C35/06C07C45/33C07C49/395C07C407/00C07C409/06B01J31/02
CPCC07C29/50C07C2101/08B01J31/0247C07C409/14B01J2231/70C07C2101/14B01J2531/985C07C45/33C07C407/00C07C2601/08C07C2601/14Y02P20/55C07C49/403C07C49/395C07C35/06C07C35/08
Inventor 大森匠佐藤靖
Owner DAICEL CHEM IND LTD
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