A kind of method directly synthesizing cyclohexanone by hydrogenation of nitrobenzene

A technology for nitrobenzene and cyclohexanone, applied in the field of chemical technology, can solve the problems of complex process route, low cyclohexene efficiency and high production cost, and achieve the effects of simple synthesis process, mild reaction conditions and high yield

Active Publication Date: 2015-11-18
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the process route is complex
In particular, the efficiency of partial hydrogenation of benzene to cyclohexene is not high, resulting in higher production costs

Method used

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  • A kind of method directly synthesizing cyclohexanone by hydrogenation of nitrobenzene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] In the autoclave, add nitrobenzene 0.49g successively, the Pd / MCM-41 (molecular sieve) catalyst 0.78g that loading capacity is mass percent 2%, AlCl 3 0.54g, cetyltrimethylammonium bromide 0.006g and water 10ml (the molar ratio is 1:0.037:1:0.004:139). Pass N 2 Make a replacement. Then the temperature was raised to 80°C, and then hydrogen gas was introduced to the reaction pressure of 1.3 MPa and maintained. After 1 hour of reaction, the hydrogen gas flow was stopped and the temperature was lowered to room temperature. The catalyst and the reaction solution were separated by filtration under reduced pressure, and the reaction solution was extracted and separated by toluene to obtain an organic phase, which was analyzed by gas chromatography. The yield of the product cyclohexanone was quantitatively calculated to be 56.7%.

Embodiment 2～5

[0035] The same operation steps and reaction conditions as in the process of synthesizing cyclohexanone in Example 1, the active metals of the catalyst were changed to Ru, Rh, Pt, Au respectively. The organic phase was analyzed by gas chromatography, and the yield of the product cyclohexanone was quantitatively calculated. The experimental results are shown in Table 1.

[0036] The impact of table 1 catalyst active metal on the synthetic cyclohexanone reaction

[0037] Example

Embodiment 6～10

[0039] The operating steps and reaction conditions of the synthetic cyclohexanone process in Example 1 are the same, and the carrier of the catalyst is changed to AC, γ-Al 2 o 3 , TS-1 (molecular sieve), HZSM-5 (molecular sieve), SBA-15 (molecular sieve), etc. The organic phase was analyzed by gas chromatography, and the yield of the product cyclohexanone was quantitatively calculated. The experimental results are shown in Table 2.

[0040] The impact of table 2 catalyst carrier on the synthetic cyclohexanone reaction

[0041] Example

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Abstract

The invention discloses a method for directly synthesizing cyclohexanone from nitrobenzene by adopting a hydrogenation process. The method comprises the following steps: adding nitrobenzene, a catalyst, an aulixilary, a surfactant and a solvent into a high-pressure kettle, introducing N2 for replacement, heating to 30-150 DEG C, introducing hydrogen until the pressure is 0.1-5MPa and keeping the pressure, reacting for 0.1-4 hours, stopping introduction of hydrogen, cooling to room temperature, performing reduced pressure filtering separation on the catalyst and a reaction solution, and performing extraction separation on the reaction solution to obtain a cyclohexanone-containing organic phase. The method has the characteristics that raw material nitrobenzene is cheap and easily available, a synthetic process is easier and convenient, the reaction conditions are mild and the yield is high; the cyclohexanone yield is close to 60%.

Description

technical field [0001] The invention relates to a method for directly synthesizing cyclohexanone by hydrogenation of nitrobenzene, specifically a process for directly synthesizing cyclohexanone by hydrogenation of nitrobenzene with nitrobenzene as a raw material and catalyzed by a loaded metal catalyst. Chemical technology field. Background technique [0002] Cyclohexanone is the main intermediate for the preparation of caprolactam and adipic acid. It is also an important organic chemical raw material and industrial solvent. It is used in industries such as medicine, paint, coating, rubber and pesticides. In addition, it also has a great role in the recycling of printing and plastics. Dosage. [0003] At present, the industrial production process route of cyclohexanone in the world mainly contains three kinds according to the raw materials: cyclohexane liquid-phase oxidation method (U.Schuchardt, D.Cardoso, R.Sercheli, et al. and (H. Zhang, S.M. Mahajani, M.M. Sharma, et ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/403C07C45/00
CPCC07C45/00C07C2601/14C07C49/403
Inventor 王延吉赵茜王淑芳杨云芳任小亮赵新强
Owner HEBEI UNIV OF TECH
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