Organo-metallic catalyst for preparing cyclohexane by hydrogenation of benzene and preparation method and application thereof

An organometallic and catalyst technology, applied in the field of organometallic catalysts for the hydrogenation of benzene to cyclohexene and its preparation, can solve problems such as pollutants, achieve low reaction temperature, mild reaction conditions, and reduce energy consumption

Active Publication Date: 2011-02-02
PETROCHINA CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the invention is to simplify the catalyst prep

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Dissolve 2.0 grams of ruthenium trichloride and 10.0 milliliters of 2-methyl-5-isopropyl-1,3-cyclohexadiene in 100 milliliters of absolute ethanol, place in a 150 milliliter three-necked flask, and heat at 70 ° C , react under normal pressure conditions, stop the reaction after 2.5 hours, cool to room temperature, and get a red precipitate, after filtering, wash the filter cake 3 times with absolute ethanol, after filtering and drying, [RuCl 2 (C 10 h 16 )] 2 That is Ru-S1, the product yield is 61%.

[0026] The prepared 1.0 g Ru-S1 and 10 g C 6 (CH 3 ) 6 Put it in a reaction tube at 170°C and react under normal pressure, stop the reaction after 5 hours, cool to room temperature, wash the reaction product with n-hexane for 5 times, and dry it in vacuum to obtain the product [RuCl 2 (C 6 (CH 3 ) 6 )] 2 , namely Ru-S2, the product yield is 70%.

[0027] Place the prepared 0.5 gram RuS2, 0.5 gram anhydrous sodium carbonate, 2 gram 1,3-cyclodihexene and 40 millil...

Embodiment 2

[0032] Dissolve 2.0 grams of ruthenium trichloride and 10.0 milliliters of 2-methyl-5-isopropyl-1,4-cyclohexadiene in 100 milliliters of absolute ethanol and place them in a 150 milliliter three-necked flask at 75° C. The reaction was carried out under high pressure conditions, the reaction was stopped after 2.0 hours, cooled to room temperature, and a red precipitate was obtained. After filtration, the filter cake was washed 5 times with absolute ethanol, and the product [RuCl 2 (C 10 h 16 )] 2 That is Ru-S1, the product yield is 63%.

[0033] The prepared 1.0 g Ru-S1 and 10 g C 6 (CH 3 ) 6 Place it in a reaction tube at 180°C and react under normal pressure, stop the reaction after 3 hours, cool to room temperature, wash the reaction product with n-hexane for 5 times, and dry it in vacuum to obtain the product [RuCl 2 (C 6 (CH 3 ) 6 )] 2 , namely Ru-S2, the product yield is 78%.

[0034] The prepared 0.5 g [RuCl 2 (C 6 (CH 3 ) 6 )] 2 , 0.5 grams of anhydrous ...

Embodiment 3

[0039] Dissolve 2.0 g of ruthenium trichloride and 10.0 ml of 2-methyl-5-isopropyl-1,3-cyclohexadiene in 100 ml of anhydrous propanol, place in a 150 ml three-necked flask, and heat at 85°C , react under normal pressure conditions, stop the reaction after 3.0 hours, cool to room temperature, and get a red precipitate, after filtering, wash the filter cake 4 times with absolute ethanol, filter and dry to get the product [RuCl 2 (C 10 h 16 )] 2 That is Ru-S1, and the product yield is 81%.

[0040] The prepared 1.0 g Ru-S1 and 10 g C 6 (CH 3 ) 6 As for the reaction in the reaction tube at 182° C. under normal pressure, the reaction was stopped after 3 hours, cooled to room temperature, washed with n-hexane for 5 times, and vacuum-dried to obtain the product [Ru(C 6 Me 6 )Cl 2 ] 2 That is Ru-S2, the product yield is 76%.

[0041] The prepared 0.5 gram Ru-S2, 0.5 gram anhydrous sodium carbonate, 5 gram cyclopentadiene and 40 milliliters of absolute ethanol are placed in a...

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PUM

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Abstract

The invention relates to an organo-metallic catalyst for preparing cyclohexane by hydrogenation of benzene and a preparation method and application thereof. The preparation method comprises the steps of: reacting RuCl3 with a ligand S1, wherein the mol ratio of the RuCl3 to the ligand S1 is 1:1.1-2.0; reacting Ru-S1 with a ligand S2 according to the mol ratio of 1:10-20, and then reacting with anhydrous sodium carbonate and 1,3-cyclohexadien according to the mol ratio of 1:2:2-1:3:3 to obtain Ru-S1-S2; reacting N-methylimidazole with 1-chlorobutan according to the mol ratio of 1:1-2 with ethylbenzene as a solvent under normal pressure at a temperature of 30-120 DEG C to obtain [BMIM]Cl; and placing the Ru-S1-S2 and the [BMIM]Cl in a fixed bed reactor for reacting to obtain an ionic liquid catalyst, wherein the mol content of the Ru-S1-S2 is 2-5 percent. The invention is used for preparing the cyclohexane by the hydrogenation of the benzene, wherein the conversion rate of the benzene reaches 20-35 percent and the selectivity of the cyclohexane reaches above 65-87 percent.

Description

technical field [0001] The invention belongs to the field of catalyst development for the hydrogenation of benzene to cyclohexene, in particular to an organometallic catalyst for the hydrogenation of benzene to cyclohexene and its preparation method and application. Background technique [0002] As an organic chemical raw material, cyclohexene is widely used in the production of pharmaceutical and pesticide intermediates, feed additives, polyester and nylon raw materials and other chemical products, especially cyclohexene is prepared by partial hydrogenation of benzene, and cyclohexene Compared with the process route of producing adipic acid through complete hydrogenation of benzene, the process route of producing cyclohexanol and reoxidation to produce adipic acid has the characteristics of resource saving, short process, energy saving and high efficiency, no waste and environmental pollution, and at the same time It also improves the safety of the production process. Part...

Claims

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Application Information

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IPC IPC(8): C07C13/20B01J31/22B01J37/00C07C5/11
CPCY02P20/52
Inventor 朱景利张金昌李民王艳辉石鸣彦朱周静程光剑崔欣任建平
Owner PETROCHINA CO LTD
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