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Method for producing ketone and/or alcohol, and system thereof

一种制造方法、制造系统的技术，应用在酮和/或醇的制造及其系统领域，能够解决分解选择率低、氢过氧化物分解速度慢、不利等问题

Inactive Publication Date: 2017-08-29
UBE IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the pH value of the alkaline metal carbonate aqueous solution is far lower than the pKa of the hydroperoxide (the negative logarithm of the acid dissociation constant is 12 to 13), so the hydroperoxide is dissociated and moved to the alkaline aqueous phase. little effect
Therefore, in the saponification using an alkali metal carbonate aqueous solution, compared with the two-stage saponification using a strong alkali, the decomposition rate of the hydroperoxide is slow, and the decomposition selectivity is also low.
Furthermore, the ketone / alcohol ratio of the produced ketone and alcohol is also lower than that of the two-stage saponification using a strong base. When the purpose is to obtain ketones, it is also disadvantageous in that ketones must be produced through dehydrogenation of alcohols.

Method used

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  • Method for producing ketone and/or alcohol, and system thereof
  • Method for producing ketone and/or alcohol, and system thereof
  • Method for producing ketone and/or alcohol, and system thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0112] 450 g of cyclohexane and 40 g of a 17% by weight aqueous solution of sodium carbonate containing 10 wt. ppm of Co (cobalt) were added to a reactor made of SUS with an internal volume of 500 ml coated with Teflon (registered trademark) on the surface, and heated. to 125°C. In this mixed solution, 50 g of a cyclohexane solution containing 20% ​​by weight of cyclohexyl hydroperoxide, 10% by weight of cyclohexanone, and 20% by weight of cyclohexanol was injected, and samples were collected at regular intervals. While measuring the decomposition rate of cyclohexyl hydroperoxide. The overall decomposition rate constant of cyclohexyl hydroperoxide was 0.063 (1 / min), and the decomposition rate after 20 minutes was 78.4%. In addition, the pH of the aqueous phase before the reaction was 11.9, and the pH of the aqueous phase after the reaction was 10.7.

Embodiment 2

[0114] The reaction was carried out in the same manner as in Example 1 except that the water phase charged into the reactor made of SUS contained 10 weight ppm of Co, 17 weight % of sodium carbonate, and 2.5 weight % of valeric acid. The overall decomposition rate constant of cyclohexyl hydroperoxide was 0.226 (l / min), and the decomposition rate after 20 minutes was 99.7%. In addition, the pH of the aqueous phase before the reaction was 10.3, and the pH of the aqueous phase after the reaction was 10.0.

Embodiment 3

[0116] The reaction was carried out in the same manner as in Example 1, except that the water phase charged into the reactor made of SUS contained 10 weight ppm of Co, 17 weight % of sodium carbonate, and 2.5 weight % of hexanoic acid. The overall decomposition rate constant of cyclohexyl hydroperoxide was 0.199 (l / min), and the decomposition rate after 20 minutes was 99.1%. In addition, the pH of the aqueous phase before the reaction was 10.3, and the pH of the aqueous phase after the reaction was 10.0.

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Abstract

In order to rapidly and highly selectively decompose a hydroperoxide of a hydrocarbon compound, and to produce a target ketone and / or alcohol, this method for producing a ketone and / or alcohol involves decomposing a hydroperoxide in a reaction solution obtained by oxidizing a hydrocarbon compound using molecular oxygen, and producing a ketone and / or alcohol having the same carbon number as the hydrocarbon compound, wherein: a hydroperoxide decomposition step for bringing the reaction solution into contact with an aqueous solution containing a carbonate of an alkaline earth metal or a carbonate of an alkali metal and a transition metal compound, and decomposing the hydroperoxide into a ketone and / or alcohol; a separation step for separating the resulting liquid into an oil phase including the ketone and / or alcohol, and an aqueous phase containing the carbonate of an alkaline earth metal or the carbonate of an alkali metal and the transition metal compound; a recovery step for burning the aqueous phase and recovering the carbonate of an alkali metal or the carbonate of an alkaline earth metal and the transition metal compound; and a recycling step for dissolving at least the carbonate of an alkali metal or the carbonate of an alkaline earth metal among the recovered substances obtained in the recovery step, in water, and recycling to the hydroperoxide decomposition step.

Description

technical field [0001] The present invention relates to a method and system for producing ketones and / or alcohols by decomposing hydroperoxides produced as intermediate products in a method for producing ketones and / or alcohols by oxidizing hydrocarbons with molecular oxygen. Background technique [0002] Research on the oxidation of hydrocarbons with molecular oxygen, especially by air, was published long ago and many methods are disclosed. Among the autoxidations of hydrocarbons, the oxidation of cyclohexane is of particular industrial importance. The obtained cyclohexanone and cyclohexanol are extremely important compounds as raw materials for nylon 6 and nylon 6,6. [0003] Oxidation of hydrocarbons by molecular oxygen takes place via the corresponding hydroperoxides. The selectivity of the oxidation reaction from hydrocarbons to hydroperoxides is high, but hydroperoxides are decomposed into various by-products other than target alcohols and ketones under oxidation rea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/53B01J23/75C07C29/132C07C35/08C07C49/403C07B61/00
CPCB01J23/75C07C29/132C07C35/08C07B61/00C07C49/403B01J19/1881B01J19/2415B01J19/2465B01J2219/00006B01J2219/00177C07C45/53C07C2601/14B01J19/24B01J2219/24
Inventor 黑泽和德杉村欣则下村秀雄倭和雄船津城司形切直哉钉本纯一河井让治
Owner UBE IND LTD
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