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Method for preparing 1-amino-2-cyano cyclopentene

A technology of cyanocyclopentene and amino, which is applied in the preparation of carboxylic acid nitrile, chemical instruments and methods, preparation of ammonia-carboxylic acid reaction, etc. It can solve the problem of difficult to obtain pure adipamide and difficult to buy ACCP finished products , less ACCP and other issues

Active Publication Date: 2019-04-12
CHINA TIANCHEN ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, it is difficult to buy finished products of ACCP on the market at present, and there are very few public documents about the preparation method of ACCP. Some documents mention that adipamide is used as a raw material to synthesize ACCP, but it is difficult to obtain higher purity on the market. Adipamide

Method used

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  • Method for preparing 1-amino-2-cyano cyclopentene
  • Method for preparing 1-amino-2-cyano cyclopentene
  • Method for preparing 1-amino-2-cyano cyclopentene

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Mix 0.5g / min dimethyl adipate with 1SLM ammonia and enter the fluidized bed reactor to react with a solid acid catalyst. The catalyst is alumina, the reaction temperature is 330°C, the reaction pressure is 0.1mpa, and the catalyst loading is 10g, and the mass space velocity of dimethyl adipate is 3h -1 , the contact time was 1s, the reaction was stopped after 10 hours of reaction, and the reaction product was condensed and collected to obtain 358g of the product. The main components included adiponitrile, ACCP, methanol and water, wherein the content of ACCP was 13.03g, and the content of adiponitrile was 186g. Then the reaction product was rectified under reduced pressure at 5000 Pa to obtain 87 g of a fraction at 170-180° C., which was mainly a mixture of ACCP and adiponitrile. Put the fraction at 5°C for 2 hours, a large amount of ACCP precipitated, filtered it to obtain 10.5 g of crude ACCP, completely dissolved ACCP with 70°C benzene, then cooled to 10°C, filtered ...

Embodiment 2

[0034] Mix 0.3g / min dimethyl adipate and 1.5SLM ammonia gas into a fixed bed reactor to react with a magnesium phosphate catalyst, the catalyst is magnesium oxide, the reaction temperature is 350°C, the reaction pressure is 0.1mpa, and the catalyst loading is 10g, and the mass space velocity of dimethyl adipate is 1.8h -1 , the contact time was 0.6s, and the reaction was stopped after 24 hours of reaction. The ammonated product of dimethyl adipate was condensed and collected to obtain 515g of the product, the main components of which were adiponitrile, ACCP, methanol and water, wherein the ACCP content was 26.8g, The dinitrile content was 267 g. The reaction product was then subjected to rectification under reduced pressure at 5000 Pa to obtain 105 g of cuts at 170-180° C., and the cuts were mainly a mixture of ACCP and adiponitrile. Put the fraction at 5°C for 2 hours, a large amount of ACCP precipitated, filtered it to obtain 23.5g of crude ACCP, completely dissolved ACCP w...

Embodiment 3

[0036] Mix 0.3g / min dimethyl adipate and 2SLM ammonia into a fixed bed reactor to react with a solid acid catalyst, the catalyst is magnesium phosphate, the reaction temperature is 400°C, the reaction pressure is 0.5mpa, and the catalyst loading is 18g, dimethyl adipate mass space velocity 1h -1 , the contact time was 0.4s, and the reaction was stopped after 10 hours of reaction. The ammonated product of dimethyl adipate was condensed and collected to obtain 215g of the product, the main components of which were adiponitrile, ACCP, methanol and water, wherein the content of ACCP was 6.7g, The dinitrile content was 111 g. The reaction product was then subjected to rectification under reduced pressure at 5000 Pa to obtain 26 g of cuts at 170-180° C., which were mainly ACCP and adiponitrile mixtures. Put the fraction at 5°C for 2 hours, a large amount of ACCP precipitated, filtered it to obtain 5.8 g of crude ACCP, completely dissolved ACCP with xylene at 100°C, then cooled to 1...

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Abstract

The invention provides a method for preparing 1-amino-2-cyano cyclopentene. According to the method, a gas-phase ammonolysis reaction is carried out by taking dimethyl adipate and ammonia gas as raw materials, and a solid acid catalyst is selected as a catalyst. Through the method, a mixture containing 1-amino-2-cyano cyclopentene and adiponitrile is prepared through high-temperature gas-phase ammoniation, and then the pure 1-amino-2-cyano cyclopentene is obtained by utilizing reduced pressure distillation and recrystallization technologies. According to the method, the raw materials are easily available, the method is simple and feasible, product purity is high, and large-scale preparation of the target product can be prepared.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for preparing 1-amino-2-cyanocyclopentene. Background technique [0002] 1-Amino-2-cyanocyclopentene (ACCP) is an isomer of adiponitrile with a molecular weight of 108.14 g / mol, a melting point of 148°C and a boiling point of 275°C at 760mmHg. Its structure diagram and mass spectrum are attached Figure 6 shown. [0003] Production practice shows that whether it is the hydrocyanation method of butadiene or the liquid-phase ammoniation method of adipic acid, more or less of its products will contain 1-amino-2-cyanocyclopentene. Since ACCP will form oligomers on the surface of Raney nickel during the hydrogenation process, it will easily lead to the deactivation of the hydrogenation catalyst. In addition, the hydrogenation products of ACCP aminocyclopentylmethylamine (AMCPA) and hexamethylenediamine (HMDA) have boiling points The proximity is difficult to separ...

Claims

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Application Information

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IPC IPC(8): C07C253/00C07C253/22C07C253/34C07C255/46
CPCC07C253/00C07C253/22C07C253/34C07C2601/10C07C255/46
Inventor 崔艳杰史文涛武金丹杨琦武孙承宇王聪杨克俭
Owner CHINA TIANCHEN ENG
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