Method for preparing 1,3-cyclohexanedione through gas-phase hydrogenation of resorcinol

A technology of resorcinol and cyclohexanedione, which is applied in the field of chemical synthesis, can solve the problems of low product yield, metal catalyst loss, troublesome operation, etc., achieve high activity and selectivity, simple preparation process, and catalyst loss small effect

Inactive Publication Date: 2018-10-09
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The post-processing of these two methods is complicated, the product yield is not high, and there are more three wastes, which pollute the environment
[0004] Chinese patent CN 104860802 discloses a method for preparing 1,3-cyclohexanedione by selective catalytic hydrogenation of palladium graphene. This method avoids the use of organic matter and inorganic salts, and overcomes the complexity of raw materials and

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Activated carbon pretreatment:

[0022] Weigh 100g of activated carbon, add 500mL of 0.5N hydrochloric acid solution, treat at 100°C for 4h, filter, wash with water until neutral; add 400mL of water, 20mL of hydrogen peroxide, 3mL of sodium hypochlorite, mix well, let stand at room temperature for 1h, filter, wash, and dry .

[0023] Preparation of Palladium Carbon Catalyst:

[0024] Weigh 10g of pretreated activated carbon, ultrasonically spray and adsorb a mixed solution containing 3mL of 20g / L palladium chloride and 2mL of hydrogen peroxide, add 20mL of water after standing for 1h, adjust the pH to 8 with sodium carbonate, add 10mL of NaHCO 3 , precipitated at 30°C for 24h, added 3mL of formaldehyde and reduced at 30°C for 8h, filtered, washed and dried to obtain catalyst 1.

[0025] Catalyst 1 catalyzes the gas-phase hydrogenation of resorcinol to 1,3-cyclohexanedione:

[0026] Dissolve resorcinol in benzene, and mix it with hydrogen after preheating vaporization...

Embodiment 2

[0029] Activated carbon pretreatment:

[0030] Weigh 100g of activated carbon, add 500mL of 0.5N hydrochloric acid solution, treat at 100°C for 4h, filter, wash with water until neutral; add 400mL of water, 20mL of hydrogen peroxide, 3mL of sodium hypochlorite, mix well, let stand at room temperature for 1h, filter, wash, and dry .

[0031] Preparation of Palladium Carbon Catalyst:

[0032] Weigh 10g of pretreated activated carbon, ultrasonically spray and adsorb a mixed solution containing 3mL of 20g / L palladium chloride, 1.5mL of hydrogen peroxide and 0.2mL of sodium hypochlorite, add 20mL of water after standing for 4 hours, adjust the pH to 9 with sodium carbonate, add 10mL of NaHCO 3 , precipitated at 50°C for 24h, raised the temperature to 60°C, added 8mL formaldehyde for reduction for 6h, filtered, washed, and dried to obtain catalyst 2.

[0033] Catalyst 2 catalyzes the gas-phase hydrogenation of resorcinol to produce 1,3-cyclohexanedione:

[0034] Dissolve resorcin...

Embodiment 3

[0037] Activated carbon pretreatment:

[0038] Weigh 100g of activated carbon, add 500mL of 1N hydrochloric acid solution, treat at 80°C for 3h, filter, wash with water until neutral; add 400mL of water, 30mL of hydrogen peroxide, 3mL of sodium hypochlorite, mix well, let stand at room temperature for 3h, filter, wash, and dry.

[0039] Preparation of Palladium Carbon Catalyst:

[0040] Weigh 10g of pretreated activated carbon, ultrasonically spray and adsorb a mixed solution containing 3mL of 20g / L palladium chloride, 1.5mL of hydrogen peroxide and 0.2mL of sodium hypochlorite, add 20mL of water after standing for 4 hours, adjust the pH to 9 with sodium carbonate, add 10mL of NaHCO 3 , precipitated at 50°C for 24h, raised the temperature to 60°C, added 8mlL formaldehyde for reduction for 6h, filtered, washed, and dried to obtain catalyst 3.

[0041] Catalyst 3 catalyzes the gas-phase hydrogenation of resorcinol to 1,3-cyclohexanedione:

[0042] Dissolve resorcinol in benzen...

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PUM

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Abstract

The invention provides a method for preparing 1,3-cyclohexanedione through gas-phase hydrogenation of resorcinol. The method comprises the following steps: dissolving resorcinol in benzene, then subjecting the dissolved resorcinol to direct vaporization, and mixing the vaporized resorcinol with hydrogen; allowing a mixture obtained in the previous step to pass through a fixed-bed reactor filled with an activated carbon-supported palladium catalyst at a mass space velocity of 0.1/h to 0.7/h, and controlling a molar ratio of hydrogen to phenol to be 2/1 to 10/1, a reaction temperature to be 180-280 DEG C and a reaction pressure of 1.0-2.0 MPa; and condensing a product obtained in the previous step with a condenser so as to obtain the hydrogenation product, i.e., 1,3-cyclohexanedione. As themethod is used for preparation of 1,3-cyclohexanedione, the conversion rate of resorcinol is up to 99.9%, and the selectivity of 1,3-cyclohexanedione is up to 97.8%.

Description

technical field [0001] The invention relates to a method for preparing 1,3-cyclohexanedione by gas-phase hydrogenation of resorcinol, which belongs to the technical field of chemical synthesis. Background technique [0002] 1,3-Cyclohexanedione is a class of important chemical intermediates, which can be used to synthesize carvedilol, a special drug for protecting cardiovascular and cerebrovascular, and treating hypertension, and anthrandansetone, an antiemetic drug. It can also be used to synthesize cosmetics, Polymer additives, excellent herbicides mesotrione and sulcotrione, etc. [0003] There are two main methods for the synthesis of 1,3-cyclohexanedione. One is to use sodium alkoxide as the condensing agent and amides as the reaction medium to synthesize 1,3-cyclohexanedione by cyclization of γ-acetylbutyrate and The condensation method of α, β-unsaturated carboxylic acid ester and ketone to synthesize 1,3-cyclohexanedione (US3922307, 1975; US 4028417, 1977); the othe...

Claims

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Application Information

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IPC IPC(8): C07C49/403C07C45/00
CPCC07C45/006C07C49/403
Inventor 陈琛金汉强赵思远季峰崎孙盛凯杨忠林
Owner CHINA PETROLEUM & CHEM CORP
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