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Method for preparing p-methylbenzonitrile through ammoxidation of p-methylbenzyl alcohol

A technology of p-toluene alcohol and tolunitrile, which is applied in the preparation of hydrocarbon ammoxidation, chemical instruments and methods, organic chemistry, etc., can solve the problems of large waste water discharge, serious environmental pollution, and large power consumption, and achieve Ease of separation, high catalytic selectivity, and low cost

Inactive Publication Date: 2019-10-01
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

⑷ p-toluidine reacts with Sandmaer through diazotization, and cyanides the diazonium salt with copper cyanide or potassium cyanide. In the production, aromatic amine and cyanide are used, which is highly toxic, discharges a lot of waste liquid, and seriously pollutes the environment and is safe. The stability is not high, and at the same time, due to the need to freeze in production to maintain low-temperature reaction, resulting in large power consumption, high production costs, and poor economic benefits; (5) in Cs 2 CO 3 , Pd(OAC) 2 / PPh 3 Refluxing CH under action 3 CN, p-toluonitrile is synthesized from p-toluene aldoxime by dehydration; (6) p-toluic acid and urea are reacted in the presence of sulfamic acid to obtain amide, and then dehydration is separated to obtain the product. This method has a large amount of wastewater discharge during the production process. serious environmental pollution

Method used

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  • Method for preparing p-methylbenzonitrile through ammoxidation of p-methylbenzyl alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] First weigh 1.83g of cobalt acetate hexahydrate and 5.61g of 1-ethyl-3-methylimidazolium hydrobromide into a 100ml beaker, stir well, add 2.0g of carbon powder, 40ml of ethanol, continue to stir for 12 hours before using Ethanol was removed by a rotary evaporator, dried and ground into powder, calcined in a tube furnace at a constant temperature of 700°C for 2 hours, and naturally cooled to obtain a Co-N-C catalyst. Take 0.2g of catalyst, 0.345g of p-methylbenzyl alcohol, 1.5ml of ammonia water, 25ml of tert-amyl alcohol, and 5bar of oxygen in a high-pressure reactor, the stirring rate is 400r / min, 130°C, react for 20 hours, and p-methylbenzyl alcohol is converted The rate is 100%, and the selectivity to p-methylbenzonitrile is 100%.

Embodiment 2

[0038] First weigh 1.83g of cobalt nitrate hexahydrate, add 3.93g of 4,4-bipyridine into a 100ml beaker, add 2.0g of carbon powder and 40ml of ethanol after stirring well, continue to stir for 12 hours, remove the ethanol with a rotary evaporator, and dry it Grind into powder, calcined in a tube furnace at a constant temperature of 700°C for 2 hours, and cooled naturally to obtain a Co-N-C catalyst. Get 0.2g catalyzer, 0.345g p-methyl benzyl alcohol, 1.5ml ammonia water, 25ml toluene, 5bar oxygen in autoclave, stirring speed is 400r / min, 150 ℃, reaction 22 hours, p-methyl benzyl alcohol conversion rate is 100%, 100% selectivity to p-methylbenzonitrile.

Embodiment 3

[0040] First weigh 1.83g of cobalt chloride hexahydrate, add 2.53g of 2-methylimidazole into a 100ml beaker, stir well, add 2.0g of carbon powder, 40ml of ethanol, continue to stir for 12 hours, remove the ethanol with a rotary evaporator, and dry it Grind into powder, calcined in a tube furnace at a constant temperature of 700°C for 2 hours, and cooled naturally to obtain a Co-N-C catalyst. Get 0.2g catalyst, 0.345g p-methylbenzyl alcohol, 1.5ml ammonia water, 25ml tetrahydrofuran, 5bar oxygen in the autoclave, stirring speed is 400r / min, 110 ℃, reaction 24 hours, p-methylbenzyl alcohol conversion rate is 100%, 100% selectivity to p-methylbenzonitrile.

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Abstract

The invention discloses a method for preparing p-methylbenzonitrile through ammoxidation of p-methylbenzyl alcohol. The method comprises the following steps that cobalt salt and a nitrogen-containingligand are mixed and stirred, carbon powder and ethyl alcohol are added, uniform stirring and mixing continue to be carried out, rotary evaporation is carried out to remove the ethyl alcohol, and drying, grinding and calcining are carried out to obtain a powdery Co-N-C catalyst; the p-methylbenzyl alcohol, an organic solvent, the Co-N-C catalyst and ammonium hydroxide are put into an autoclave, anappropriate amount of oxygen is introduced, a reaction is carried out at 100-150 DEG C for 12-24 hours, and separation is carried out to obtain the p-methylbenzonitrile. The method for preparing thep-methylbenzonitrile through the ammoxidation of the p-methylbenzyl alcohol has the advantages that the non-precious metal catalyst is used for reducing the cost, the p-methylbenzyl alcohol conversionrate and the p-methylbenzonitrile selectivity both reach 100%, and the catalyst is easy to separate; the whole process meets the concepts of green chemistry and sustainable development, and is a synthetic route with most attraction and industrial application prospects.

Description

Technical field [0001] The invention belongs to the technical field of chemical synthesis, and specifically relates to a method for preparing p-toluonitrile through ammonia oxidation of p-toluyl alcohol. Background technique [0002] The chemical name of p-methylbenzonitrile (P-methylbenzonitrile) is 4-methylbenzonitrile. It is a colorless and transparent liquid at room temperature, with a molecular weight of 117.15, a melting point of 29.5°C, and a boiling point of 217.6°C. p-Toluonitrile is an important intermediate in the production of fluorescent whitening agents OB-1, KSN and DPP pigments. The hydrolysis product, p-toluic acid, and the reduction product, p-toluamine, can also be used in medicines, pesticides and other applications. Synthesis of fine chemical products. [0003] In the past, the main synthesis methods of p-toluonitrile were: (1) Using p-xylene as raw material, vanadium series, chromium series or titanium series as catalysts, under high temperature condit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/28C07C255/50B01J27/24
CPCC07C253/28B01J27/24C07C255/50
Inventor 夏语嫣吕庆阳袁华
Owner WUHAN INSTITUTE OF TECHNOLOGY
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