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Method for co-production of cyclohexanol and absolute ethyl alcohol

A technology of anhydrous ethanol and cyclohexanol, applied in chemical instruments and methods, preparation of organic compounds, organic compound/hydride/coordination complex catalysts, etc., can solve the problem of acetic acid vapor being corrosive to equipment and the mixture cannot be separated , high energy consumption in the distillation process, etc., to achieve the effect of realizing full utilization of materials, reducing equipment requirements and production energy consumption, and improving conversion rate

Inactive Publication Date: 2014-12-10
河北美邦工程科技股份有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are also some problems in this process route: (1) in the process of cyclohexene esterification reaction, the conversion rate of general cyclohexene is 60%~70%, and the selectivity is 97%~98%, while benzene, cyclohexene Add acetic acid to directly carry out esterification reaction in the mixed solution that alkene, hexanaphthene are formed, because the existence of benzene has bigger influence to the conversion rate and the selectivity of esterification reaction, influences the yield of final product cyclohexanol; ( 2) In the process of cyclohexene esterification, the conversion rate of cyclohexene can only reach 93%~94%; (3) In the process of distilling and separating benzene, cyclohexane and acetic acid, benzene, acetic acid and cyclohexane form a ternary Azeotrope, even cyclohexyl acetate may also participate in the formation of azeotrope, so that the mixture cannot be separated by simple distillation, and even this mixture may not be separated; (4) the distillation process of acetic acid has high energy consumption, And the formed acetic acid vapor is corrosive to the equipment

Method used

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  • Method for co-production of cyclohexanol and absolute ethyl alcohol

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] (1) Add 30 L of benzene, 500 g of Ru-ZnSO to the benzene hydrogenation reactor 4 -Zn(OH) 2 -ZrO 2 / SiO 2 (where Ru, ZnSO 4 , Zn(OH) 2 and ZrO 2 The mass percent composition in the catalyst is respectively 5%, 1%, 1% and 2%) and HZSM-10 molecular sieve 300 g, stir after sealing, be heated to 150 DEG C, then charge into hydrogen in the reactor, make The partial pressure was 5 MPa, and the reaction was carried out for 0.5 hours. A small amount of reaction solution was taken out by the sampling valve and analyzed by gas chromatography. It can be seen that the conversion rate of benzene was 55.3%, and the yield of cyclohexene was 35.2%. After the benzene hydrogenation reaction is completed, the oil phase in the kettle is dewatered to reduce the water content to below 15 ppm.

[0055] (2) Use DMAc as the extractant to extract and remove benzene from the above-mentioned oil phase after dehydration, the flow rate of DMAc is 0.18 kmol / h, and the volume ratio of DMAc to t...

Embodiment 2

[0061] (1) Add 30 L of benzene, 500 g of Ru-ZnSO to the benzene hydrogenation reactor 4 -Zn(OH) 2 -ZrO 2 / SiO 2 (where Ru, ZnSO 4 , Zn(OH) 2 and ZrO 2 The mass percent composition in the catalyst is respectively 5%, 1%, 1% and 2%) and HZSM-10 molecular sieve 300 g, stir after sealing, be heated to 150 DEG C, then charge into hydrogen in the reactor, make The partial pressure is 5 MPa, and the reaction time is 0.5 hours. A small amount of reaction solution was taken out by the sampling valve and analyzed by gas chromatography. It can be seen that the conversion rate of benzene was 55.3%, and the yield of cyclohexene was 35.2%. After the benzene hydrogenation reaction is completed, the oil phase in the kettle is dewatered to reduce the water content to below 15 ppm.

[0062] (2) Use DMAc as the extractant to extract and remove benzene from the above-mentioned oil phase after dehydration, the flow rate of DMAc is 0.18 kmol / h, and the volume ratio of DMAc to the oil phase ...

Embodiment 3

[0068] (1) Add 30 L of benzene, 500 g of Ru-ZnSO to the benzene hydrogenation reactor 4-Zn(OH) 2 -ZrO 2 / SiO 2 (where Ru, ZnSO 4 , Zn(OH) 2 and ZrO 2 The mass percent composition in the catalyst is respectively 5%, 1%, 1% and 2%) and HZSM-10 molecular sieve 300 g, stir after sealing, be heated to 150 DEG C, then charge into hydrogen in the reactor, make The partial pressure was 5 MPa, and the reaction was carried out for 0.5 hours. A small amount of reaction solution was taken out by the sampling valve and analyzed by gas chromatography. It can be seen that the conversion rate of benzene was 55.3%, and the yield of cyclohexene was 35.2%. After the benzene hydrogenation reaction is completed, the oil phase in the kettle is dewatered to reduce the water content to below 15 ppm.

[0069] (2) Use DMAC as the extractant to extract and remove benzene from the above-mentioned oil phase after the dehydration treatment, the DMAC flow rate is 0.18 kmol / h, the volume ratio of the...

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Abstract

The invention discloses a method for co-production of cyclohexanol and absolute ethyl alcohol. The method comprises the steps of: (1) benzene hydrogenation; (2) debenzolization by extraction of a mixture; (3) cyclohexane removal by extractive distillation; (4) first esterification; (5) second esterification; and (6) mixed ester hydrogenation. The method has the characteristics that as a two-step esterification method is adopted, acetic acid which does not react in the first esterification process reacts with excess ethyl alcohol in the second esterification process so as to be converted to ethyl acetate, thus avoiding corrosion to equipment in the subsequent acetic acid distillation separation process, lowering the equipment requirement and the production energy consumption and saving the cost. According to the method disclosed by the invention, cyclohexene has a high conversion rate (no less than 99 percent), and acetic acid is not needed to be separated in the middle process and is completely converted to absolute ethyl alcohol with a higher additional value finally. The cyclohexanol prepared by the method satisfies the high-speed caprolactam spinning production process.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for producing cyclohexanol and ethanol by using benzene and acetic acid as raw materials, and belongs to the technical field of organic synthesis. Background technique [0002] Cyclohexanol is an important chemical raw material, an intermediate in the production of adipic acid and caprolactam, and an important intermediate in the production of nylon 6 and nylon 66. It is widely used in medicine, sanitation, fine chemicals, chemical fiber and wood preservation, etc. Many fields. At present, the main production methods of cyclohexanol are "cyclohexane oxidation method" and "cyclohexene hydration method". "Cyclohexene hydration method" was developed by Japan Ashai Company, and it was industrialized in 1989. The process first produces cyclohexene by selective catalytic hydrogenation of benzene in a tank reactor, accompanied by the complete hydrogenation produc...

Claims

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Application Information

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IPC IPC(8): C07C29/149C07C31/135C07C31/08
CPCC07C29/149B01J31/10C07C5/10C07C5/11C07C7/08C07C67/08C07C2601/14C07C2601/16C07C13/18C07C13/20C07C69/14C07C31/08C07C35/08
Inventor 金作宏张旭斌王富民张玉新尹更昌高文杲
Owner 河北美邦工程科技股份有限公司
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