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A method for preparing 1-amino-2-cyanocyclopentene

A technology of cyanocyclopentene and amino, which is applied in the preparation of carboxylic acid nitriles, chemical instruments and methods, and the preparation of organic compounds. Amines and other issues

Active Publication Date: 2021-09-03
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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  • A method for preparing 1-amino-2-cyanocyclopentene
  • A method for preparing 1-amino-2-cyanocyclopentene
  • A method for preparing 1-amino-2-cyanocyclopentene

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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, and the reaction was stopped after 10 hours of reaction. The reaction product was condensed and collected to obtain 358g of 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 and ...

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. Then, the reaction product was rectified under reduced pressure at 5000 Pa to obtain 105 g of fractions at 170-180° C., and the fractions 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 23.5 g of crude ACCP, completely dissolved ACCP with 8...

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. Then the reaction product was rectified under reduced pressure at 5000 Pa to obtain 26 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 5.8 g of crude ACCP, completely dissolved ACCP with xylene at 100°C, then cooled to 10°C, fil...

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Abstract

The invention provides a method for preparing 1-amino-2-cyanocyclopentene, the method uses dimethyl adipate and ammonia as raw materials to carry out gas-phase ammonolysis reaction, and the catalyst is selected as a solid acid catalyst; A mixture containing 1-amino-2-cyanocyclopentene and adiponitrile was prepared by high-temperature gas-phase ammoniation, and then pure 1-amino-2-cyanocyclopentene was obtained by vacuum distillation and recrystallization techniques. The method has easy-to-obtain raw materials, is simple and easy to implement, has high product purity, and can realize mass preparation of target products.

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 Image 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 separa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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