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Method and special catalyst for preparing cyclohexanone in one step by phenol hydrogenation

A technology for the preparation of hydrogen and cyclohexanone, which is applied to catalyst supports, metal/metal oxide/metal hydroxide catalysts, physical/chemical process catalysts, etc., to achieve high selectivity, good stability, and mild reaction conditions

Inactive Publication Date: 2010-05-19
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above results show that the conversion rate and selectivity of cyclohexanone prepared by one-step liquid phase hydrogenation of phenol need to be further improved, and there is an urgent need to develop a low-temperature, high-efficiency, and inexpensive catalytic system for hydrogenation of phenol to cyclohexanone

Method used

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  • Method and special catalyst for preparing cyclohexanone in one step by phenol hydrogenation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1, the molar ratio is 5: 1 loading on TiO 2 AlCl on 3 One-step hydrogenation of phenol to cyclohexanone over a supported Pd catalyst

[0026] Add 1.0mmol phenol, catalyst (by 0.1mmol AlCl 3 (loaded on TiO 2 above) and 0.02 mmol of any of the following supported Pd catalysts: Pd / C, Pd / SiO 2 , Pd / Al 2 o 3 and Pd / SBA-15) and 1ml of dichloromethane, heated to 30°C, fed hydrogen until the system pressure was 1MPa, under stirring conditions, reacted for 30 hours, cooled, degassed, and filtered to separate the catalyst from the reaction solution , and the reaction solution was analyzed by gas chromatography. The gas chromatography conditions are as follows: Agilent 4890D gas chromatograph, FID detector, capillary column (Innowax, 30m × 0.252mm × 0.25μm), take the temperature program, the initial column temperature is 60 ° C, keep for 5 minutes, and then 20 ° C / The heating rate of min was increased to 200°C for 5 minutes. The carrier gas is 99.99% high-puri...

Embodiment 2

[0030] Embodiment 2, the molar ratio is 5: 1 load on SiO 2 AlCl on 3 One-step hydrogenation of phenol to cyclohexanone over a supported Pd catalyst

[0031] Add 1.0mmol phenol, catalyst (by 0.1mmol AlCl 3 (loaded on SiO 2 above) and 0.02 mmol of any of the following supported Pd catalysts: Pd / C, Pd / SiO 2 , Pd / Al 2 o 3 and Pd / SBA-15) and 1ml of dichloromethane, heated to 30°C, fed hydrogen until the system pressure was 1MPa, under stirring conditions, reacted for 30 hours, cooled, degassed, and filtered to separate the catalyst from the reaction solution , and the reaction solution was analyzed by gas chromatography. The gas chromatography conditions are the same as in Example 1.

[0032] The gas chromatographic analysis results of three repeated experiments are shown in Table 2:

[0033] Table 2. Made of AlCl 3 Results of hydrogenation of phenol catalyzed by catalysts composed of different supported Pd catalysts

[0034] catalyst

Embodiment 3

[0035] Embodiment 3, the molar ratio is 5: 1 load on Al 2 o 3 AlCl on 3 One-step hydrogenation of phenol to cyclohexanone over a supported Pd catalyst

[0036] One-step Preparation of Cyclohexanone by Hydrogenation of Phenol

[0037] Add 1.0mmol phenol, catalyst (by 0.1mmol AlCl 3 (loaded at Al 2 o 3 above) and 0.02 mmol of any of the following supported Pd catalysts: Pd / C, Pd / SiO 2 , Pd / Al 2 o 3 and Pd / SBA-15) and 1ml of dichloromethane, heated to 50°C, fed hydrogen until the system pressure was 1MPa, under stirring conditions, reacted for 30 hours, cooled, degassed, and filtered to separate the catalyst from the reaction solution , and the reaction solution was analyzed by gas chromatography. The gas chromatography conditions are the same as in Example 1. The gas chromatographic analysis results of three repeated experiments are shown in Table 3:

[0038] The gas chromatographic analysis results of three repeated experiments are shown in Table 3:

[0039] Table 3...

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Abstract

The invention discloses a method and a special catalyst for preparing cyclohexanone in one step by phenol hydrogenation. The catalyst for preparing the cyclohexanone in one step by phenol hydrogenation comprises Lewis acid and a loading type metal catalyst, wherein the mole ratio of the Lewis acid to the loading type metal catalyst is 10:1 to 1:10. The method for preparing the cyclohexanone comprises the steps of: using dichloromethane or CO2 as a reaction solvent; and reacting the phenol with hydrogen to generate the cyclohexanone in the presence of the catalyst. The method for preparing the cyclohexanone in one step by phenol hydrogenation has the advantages of simple preparing process, high activity and selectivity, moderate reaction condition, good stability, and the like; in addition, after the reaction is completed, reaction liquid and the catalyst can be separated through filtering and repeatedly used, and catalyzing activity and selectivity are not reduced. Experiments prove that the method for preparing the cyclohexanone can achieve the percent conversion of the phenol more than 99.9 percent and the selectivity of the cyclohexanone more than 95 percent.

Description

technical field [0001] The invention relates to a method for preparing cyclohexanone by one-step hydrogenation of phenol and a special catalyst thereof. Background technique [0002] Cyclohexanone is mainly used to prepare monomer caprolactam and adipic acid of synthetic fiber nylon 6 and nylon 66. It is also an important intermediate of fine chemicals such as medicine, paint and dye, and is used in a small amount in industries such as rubber, leather, paint and pesticides. produced solvents. There are two production methods of cyclohexanone, cyclohexane oxidation method (U.Schuchardt, D.Cardoso, R.Sercheli, R.Pereira, R.S.da Cruz, M.C.Guerreiro, D.Mandelli, E.V.Spinacé, E.L.Pires, " Cyclohexane oxidation continues to be a challenge", Appl.Catal.A: Gen., 2001, 211, 1-17) and phenol hydrogenation (L.M.Sikhwivhilu, N.J.Coville, D.Naresh, K.V.R.Chary, V.Vishwanathan, Nanotubular titanate supported palladium catalysts: The influence of structure and morphology on phenol hydrog...

Claims

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Application Information

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IPC IPC(8): C07C49/403C07C45/51B01J23/42B01J23/44B01J32/00
Inventor 姜涛韩布兴刘会贞杨冠英
Owner INST OF CHEM CHINESE ACAD OF SCI
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