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Oxidation catalyst for hydrocarbon compound, and method and apparatus for producing oxide of hydrocarbon compound using same

A technology for oxidation catalysts and hydrocarbon compounds, which is applied in the directions of organic compound/hydride/coordination complex catalysts, preparation of organic compounds, preparation of peroxy compounds, etc., and can solve the problem of reducing the yield of cyclohexanone and cyclohexanol and accelerating the Hydrocarbon compound oxidation reaction, insufficient selectivity, etc.

Inactive Publication Date: 2013-06-05
UBE IND LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the case of using a transition metal compound, the hydroperoxide is decomposed by the action of the transition metal, and the oxidation reaction of the hydrocarbon compound is accelerated by the generated alkoxyl radical and peroxyl radical. Side reactions, etc., its selectivity is not sufficient
Therefore, it is considered that the method of using a transition metal compound as a catalyst does not correspond to the technical idea of ​​suppressing the decomposition of cyclohexyl hydroperoxide in the above-mentioned oxidation step of cyclohexane and selectively decomposing cyclohexyl hydroperoxide in the next step. capacity, there is the problem that the yield of cyclohexanone and cyclohexanol decreases

Method used

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  • Oxidation catalyst for hydrocarbon compound, and method and apparatus for producing oxide of hydrocarbon compound using same
  • Oxidation catalyst for hydrocarbon compound, and method and apparatus for producing oxide of hydrocarbon compound using same
  • Oxidation catalyst for hydrocarbon compound, and method and apparatus for producing oxide of hydrocarbon compound using same

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no. 1 approach

[0061] The easiness of oxidation of a hydrocarbon compound by molecular oxygen is affected by the bond energy between skeleton carbon and hydrogen. Generally, the bond energy of carbon-hydrogen increases in the order of tertiary carbon, secondary carbon, and primary carbon. In addition, the electron-withdrawing substituent, the aromatic substituent, and the carbon-carbon double bond have the effect of reducing the carbon-hydrogen bond energy of the carbon to which the substituent and the like are bonded and the adjacent carbon. Therefore, straight-chain hydrocarbons and cyclic hydrocarbons having no substituents are generally less likely to be oxidized.

[0062] For example, cyclohexane has a carbon-hydrogen bond energy as high as 94 kcal / mol (Non-Patent Document 1), and is difficult to be oxidized. This is why cyclohexanone and cyclohexanol cannot be obtained in high yields even though cyclohexane is an industrially important compound.

[0063] In order to promote the oxida...

no. 2 approach

[0135] The oxidation catalyst according to the second embodiment of the present invention is an oxidation catalyst comprising the N-hydroxy compound represented by the above-mentioned general formula (1a) and general formula (1b), more preferably comprising the following general formula (3) oxidation catalysts of oxime compounds. The oxime compound represented by general formula (3) can be used individually by 1 type, or can use it in combination of 2 or more types. The oxidation catalyst according to the second embodiment of the present invention has a large effect of promoting the oxidation reaction of hydrocarbon compounds, and can oxidize hydrocarbon compounds even if it is used in a small amount.

[0136]

[0137] In the general formula (3), R1 and R2 are independently substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted A substituted cycloa...

no. 3 approach

[0173] In a third embodiment of the present invention, a hydrocarbon compound is oxidized by means of molecular oxygen (commonly referred to as "auto-oxidation"), thereby forming the corresponding hydroperoxide. Furthermore, the hydroperoxide is decomposed to produce the corresponding ketone and / or alcohol.

[0174] Here, ketones and alcohols are more easily oxidized than hydrocarbon compounds as starting materials, and oxides in high oxidation states such as carboxylic acids are by-produced. Therefore, the following methods are generally used: a method of performing an oxidation reaction without adding a transition metal compound such as cobalt, which is generally used as an oxidation catalyst (called a catalyst-free oxidation method); The method of suppressing the decomposition of hydroperoxide in the oxidation step by using a chemical agent (Patent Document 1), and the method of decomposing the hydroperoxide in a non-oxidizing atmosphere in the next step (referred to as a h...

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Abstract

According to the first embodiment of the present invention, an oxide of a hydrocarbon compound can be produced with high yield and high productivity by oxidizing the hydrocarbon compound with molecular oxygen in the co-presence of an N-hydroxy compound, such as methyl ethyl ketone or N-hydroxysuccinimide, and a phosphate ester, such as dibutyl phosphate. According to another embodiment of the present invention, an oxide of a hydrocarbon compound can be produced with high yield by using an oxidation catalyst that comprises an oxime compound, such as methyl ethyl ketone. According to another embodiment of the present invention, an alcohol and / or a ketone can be produced with high yield by oxidizing the hydrocarbon compound at a temperature of 160 DEG C. or less, and by decomposing the resulting hydroperoxide, for example, in a unit having an inner surface formed by a material from which no transition metal ion is generated.

Description

technical field [0001] The present invention relates to an oxidation catalyst for producing at least one of alcohols, ketones, and hydroperoxides by oxidizing a hydrocarbon compound with molecular oxygen, and a method and apparatus for producing an oxide of a hydrocarbon compound using the same. Background technique [0002] Conventionally, the oxidation of hydrocarbon compounds by molecular oxygen, especially the oxidation by air, has been studied, and various methods have been disclosed. Among the autoxidation of hydrocarbon compounds, the oxidation of cyclohexane is particularly important industrially. The obtained cyclohexanone and cyclohexanol are extremely important compounds as raw materials for nylon 6 and nylon 6,6. [0003] The oxidation of hydrocarbon compounds by molecular oxygen is mainly performed through two steps. The first step is a step of oxidizing a hydrocarbon compound to generate a hydroperoxide, and the second step is a step of decomposing the hydrop...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/02B01J31/04C07C29/50C07C31/135C07C45/33C07C49/303C07C407/00C07C409/14C07B61/00
CPCB01J31/0258C07C51/316B01J2231/70C07C251/48B01J31/0247C07C407/00C07C2101/14C07C251/36C07C29/50C07C251/44B01J31/2239B01J31/0241C07C45/33B01J2531/845B01J19/02B01J31/04C07C2601/14C07C35/08C07C49/303C07C29/94C07C31/135B01J31/02
Inventor 黑泽和德船津城司形切直哉钉本纯一
Owner UBE IND LTD
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