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Method for preparing alkylcyanophenyl

A technology for alkyl benzonitrile and alkyl benzene is applied in the field of preparing alkyl benzonitrile, and can solve the problem of low dialkyl benzene conversion rate, low product yield, difficult alkyl benzonitrile synthesis reaction, and tert-butyl benzonitrile selectivity. low problems, to achieve the effect of good application value, simple preparation method and environmental friendliness

Inactive Publication Date: 2008-09-17
SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The direct ammoxidation of dialkylbenzene (such as xylene) can obtain two kinds of products of phthalonitrile and alkylbenzonitrile, and general alkylbenzonitrile is as the by-product of phthalonitrile; It is undoubtedly a very attractive idea to prepare alkyl benzonitrile through the base benzonitrile stage, but the problem of low selectivity has not been solved so far.
For example, when using tert-butyltoluene as raw material to prepare tert-butylbenzonitrile by gas-phase ammoxidation method, the reaction generally requires a high temperature of about 400°C. Very low, easy to generate phthalonitrile (Chmyr I M, Bukeikhanov N R, Suvorov B V.Oxidative Ammonolysis ofp-Tert-Butyltoluene in the Presence of a Vanadium-Titanium Catalyst.lzv Akad NaukKaz SSR, Ser Khim, 1982, (3 ): 61-64.) In order to improve the selectivity of generating mononitrile, the reaction temperature can be reduced, such as carrying out the liquid-phase ammoxidation reaction at 100~200° C.; it has been found that as the reaction temperature decreases, the The selectivity increases; however, the reaction temperature is too low, the conversion rate of dialkylbenzene and the yield of the product are all very low, which cannot meet the requirements of the application
Therefore, the direct ammoxidation method is difficult to become the synthetic reaction of alkyl benzonitrile

Method used

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  • Method for preparing alkylcyanophenyl
  • Method for preparing alkylcyanophenyl
  • Method for preparing alkylcyanophenyl

Examples

Experimental program
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Embodiment 1

[0023]

[0024] Add 1.5015g of paraformaldehyde, 3.4075g of anhydrous zinc chloride and 7.5ml of concentrated hydrochloric acid into a 250ml three-necked flask, then heat and stir to fully mix the solid zinc chloride and paraformaldehyde with concentrated hydrochloric acid, when the temperature rises to 60°C 19.8 g of toluene was added, and HCl gas was introduced under vigorous stirring for 6 h. After the reaction was finished, the product was transferred to a separatory funnel for static layering, and the concentrated hydrochloric acid solution of the lower floor was first separated, and then the solution was washed with 10% Na 2 CO 3 Aqueous and distilled water washes, anhydrous Na 2 SO 4 After drying, use a rotary evaporator to evaporate excess toluene, and finally distill under reduced pressure to obtain a mixture of o-methylbenzyl chloride and p-methylbenzyl chloride with a yield of 86.5%.

Embodiment 2

[0026] Add 1.5 g of paraformaldehyde, 2.0 g of anhydrous aluminum chloride and 20 ml of ethylbenzene into the three-neck flask, raise the temperature to 60° C., and pass HCl gas under vigorous stirring for 8 h. After the reaction was over, the product was transferred to a separatory funnel and washed with 10% Na 2 CO 3 Aqueous and distilled water washes, anhydrous Na 2 SO 4 After drying, use a rotary evaporator to evaporate excess ethylbenzene, and finally distill under reduced pressure to obtain a mixture of o-ethylbenzyl chloride and p-ethylbenzyl chloride with a yield of 89.2%.

Embodiment 3

[0028] Add 2.0g of formaldehyde, 3ml of concentrated sulfuric acid, 6ml of concentrated hydrochloric acid and 20ml of cumene into the three-neck flask respectively, then heat to 40°C, and inject HCl gas for 5h under vigorous stirring. After the reaction was finished, the product was transferred to a separatory funnel for static layering, and the concentrated hydrochloric acid solution of the lower floor was first separated, and then the solution was washed with 10% Na 2 CO 3 Aqueous and distilled water washes, anhydrous Na 2 SO 4 After drying, excess cumene was distilled off first by vacuum distillation, and then the mixture of o-cumyl benzyl chloride and p-cumyl benzyl chloride was obtained by vacuum distillation with a yield of 78.7%.

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Abstract

The invention discloses a new method of preparing alkyl cyanophenyl. The new method comprises the following steps: alkylbenzene is used as raw material, is processed through chloromethylation to obtain alkyl benzyl chloride first, and then is processed through ammoxidation to prepare the alkyl cyanophenyl. In the new method, the reaction-path is short, the reaction temperature is low, the yield rate is high, and the selectivity is high. The invention also discloses a high efficiency catalyst used for preparing the alkyl cyanophenyl through the ammonia oxidation process. The catalyst is silica gel or a vanadium chromium five-component system loaded by aluminum oxide, wherein, the vanadium chromium five-component system is VaCrbCcDdEeOx; the catalyst can effectively catalyze the alkyl benzyl chloride to act ammoxidation to obtain the alkyl cyanophenyl; the high efficiency catalyst has the advantages of high activity, high product yield rate, good selectivity, high product purity, long service life, simple technology, etc.

Description

technical field [0001] The invention relates to a new method for preparing alkyl benzonitrile and a special catalyst for ammoxidation. It belongs to the technical field of organic chemistry and also belongs to the technical field of organic fine chemicals. Background technique [0002] Alkylbenzonitriles are very important fine chemicals and organic synthesis intermediates; due to the good reactivity of nitrile groups, alkylbenzoic acids, alkylbenzamides, alkylanilines, A series of fine chemicals such as cyanobenzoic acid are widely used in medicine, pesticides, pigments, dyes, rubber, optoelectronic materials and other fields. [0003] The preparation method of alkyl benzonitrile can be divided into following several kinds according to reaction raw material: the one, alkyl aniline diazotization method, the 2nd, alkyl benzoic acid ammoniation method, the 3rd, alkylbenzaldehyde oximation dehydration method, the 4th, Dialkylbenzene ammoxidation method. The first three metho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/50C07C253/24
Inventor 谢光勇刘娜
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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