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Synthesis method of 2-methylene glutaronitrile

A methyleneglutaronitrile and synthesis method technology, applied in chemical instruments and methods, carboxylic acid nitrile preparation, organic compound preparation, etc., can solve the problems of environmental pollution, low reaction concentration, low selectivity, etc., and achieve atomic Strong economy, easy access to raw materials, and environmental friendliness

Inactive Publication Date: 2013-09-25
JIANGSU YANGNONG CHEM GROUP +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the existing methods for preparing 2-methyleneglutaronitrile by dimerization of acrylonitrile often require harsh conditions such as high temperature and high pressure (Tetrahedron Lett. Defects such as low efficiency and low reaction concentration, especially the need to use expensive and toxic ruthenium catalysts, pollute the environment, and the cost is high (J.Chem.Res.1995,267; J.Mol.Cat.1992,73,L15 -19; J.Chem.Soc.Perkin Trans.12002,1318-1323;Tetrahedron Lett.1987,28,4591-4592;J.Org.Chem.1970,35,3045-3048)

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Add acrylonitrile, tert-butanol, and tricyclohexylphosphine sequentially into a 50mL round-bottomed flask (feeding amount is shown in Table 1), connect a reflux condenser, heat to 70°C and stir for 10 hours under nitrogen protection, and react The liquid gradually turns yellow. Connect the distillation device for distillation, and first distill off the solvent tert-butanol (80-83°C). The residue was transferred to a smaller container (20mL round bottom flask) and distilled under reduced pressure at 115-128°C / 10mmHg to distill out the product 2-methyleneglutaronitrile. 7.0 g of benzonitrile were obtained, yield 86%.

[0016] The feed intake of table 1 reaction raw material, solvent and catalyst

[0017] substance

Embodiment 2

[0019] Other conditions are the same as in Example 1, except that the consumption of the tricyclohexylphosphine catalyst is changed, and the reaction results are shown in Table 2.

[0020] The influence of table 2 catalyst consumption on reaction

[0021] Numbering

Embodiment 3

[0023] Other solvents were used to replace tert-butanol, and the solvent consumption was 20 mL. Other conditions were the same as in Example 1. The experimental results are shown in Table 3.

[0024] The impact of different solvents in table 3 on the reaction

[0025] Numbering

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PUM

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Abstract

The invention provides a synthesis method of 2-methylene glutaronitrile. According to the method, tricyclohexylphosphine is taken as a catalyst; an acrylonitrile dimer is chemically catalyzed under the condition with a solvent or not; the dosage of the catalyst is 0.1-5.0 wt%; the reaction temperature is 50-90 DEG C; and the initial concentration of the acrylonitrile is 3.0-15.2 mol / L. Furthermore, the reaction product is purified in a distilling manner. The method is available in materials, mild in reaction condition, high in yield, good in selectivity, strong in atom economy, friendly to the environment and applicable to industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing 2-methyleneglutaronitrile, more specifically, a method for catalyzing dimerization of acrylonitrile as a raw material into 2-methyleneglutaronitrile. Background technique [0002] 2-Methyleneglutaronitrile is an intermediate for the preparation of the fungicide bromothalonil, which has important application value. Acrylonitrile is cheap and easy to obtain, and using acrylonitrile as raw material to catalyze dimerization into 2-methyleneglutaronitrile is an effective method. The method has the advantages of high atom economy, cheap raw materials and environmental friendliness. [0003] However, the existing methods for preparing 2-methyleneglutaronitrile by dimerization of acrylonitrile often require harsh conditions such as high temperature and high pressure (Tetrahedron Lett. Defects such as low efficiency and low reaction concentration, especially the need to use expensive and toxic ruthenium catal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/09
Inventor 俞磊王俊张旭陈天丁克鸿
Owner JIANGSU YANGNONG CHEM GROUP
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