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Preparation method of 3-bromopropionitrile

A technology of bromopropionitrile and acetonitrile, applied in the field of preparation of 3-bromopropionitrile, can solve the problems of high raw material cost, unfriendly environment, low yield and the like, and achieves high material utilization rate, simple post-processing and high yield Effect

Active Publication Date: 2020-02-14
ASTATECH CHENGDU BIOPHARM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The object of the present invention is to provide a kind of preparation method of 3-bromopropionitrile, solve the problem of high raw material cost, low yield, many three wastes and unfriendly environment in the existing process The problem

Method used

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  • Preparation method of 3-bromopropionitrile
  • Preparation method of 3-bromopropionitrile
  • Preparation method of 3-bromopropionitrile

Examples

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Embodiment 1

[0027] A kind of preparation method of 3-bromopropionitrile of the present invention, concrete steps are as follows: dissolve trimethylbromosilane (71.40kg, 653.60mol, 0.95eq) in acetonitrile (15Vol), start stirring; Under nitrogen protection, 20~40 Add acrylonitrile (25.40kg, 479.25mol, 1eq) dropwise at ℃; add deionized water (10.60kg, 294.44mol, 2eq) dropwise at a controlled reaction temperature of 20-40°C after dropping, and react overnight at 20-40°C Until the raw material disappears substantially, the precipitated solid is filtered, the filtrate is concentrated under reduced pressure until almost no solvent flows out, and the rectification device (75 ± 5°C, 9-12mmTor) is used for rectification to obtain 45.45kg of colorless liquid with a yield of 70.9% ( Gas chromatographic purity greater than 98%). H NMR (CDCl 3 ,400MHz): δ3.52-3.55(t,3H),2.98-3.01(t,2H). Synthetic route of the present invention such as figure 1 shown.

Embodiment 2

[0029] A preparation method of 3-bromopropionitrile of the present invention, the specific steps are as follows: dissolve trimethylbromosilane (71.40g, 0.66mol, 0.95eq) in toluene (12Vol), start stirring; under nitrogen protection, 20-40 Add acrylonitrile (25.40g, 0.48mol, 1eq) dropwise at ℃; add deionized water (10.60g, 0.29mol, 2eq) dropwise at a controlled reaction temperature of 20-40°C after the dropwise addition, and react overnight at 20-40°C Until the raw material disappears substantially, the precipitated solid is filtered, the filtrate is concentrated under reduced pressure until there is no solvent to flow out, and the rectification device (75 ± 5°C, 9-12mmTor) is used for rectification to obtain 38.0g, yield 59.7% (gas chromatographic purity greater than 98%). H NMR (CDCl 3 ,400MHz): δ3.52-3.55(t,3H),2.98-3.01(t,2H).

[0030] Comparing Example 1 and Example 2, it can be seen that the yield of using acetonitrile as the organic solvent is greater than that of tolue...

Embodiment 3

[0032] A preparation method of 3-bromopropionitrile of the present invention, the specific steps are as follows: dissolve trimethylbromosilane (71.40g, 0.66mol, 0.95eq) in acetonitrile (15Vol), and start stirring. Under the protection of nitrogen, add acrylonitrile (25.40g, 0.48mol, 1eq) dropwise at 0-20°C; after the addition, control the reaction temperature at 0-20°C and add deionized water (10.60g, 0.29mol, 2eq) dropwise, After the dropwise addition is completed, react at 10-20°C overnight until the raw materials basically disappear, filter the precipitated solid, concentrate the filtrate under reduced pressure until almost no solvent flows out, and use a rectification device (75±5°C, 9-12mmTor) to rectify to obtain 41.0 g, yield 64.2% (gas chromatography purity greater than 98%). H NMR (CDCl 3 ,400MHz): δ3.52-3.55(t,3H),2.98-3.01(t,2H).

[0033] Comparing Example 1 and Example 3, it can be seen that the yield will change at different reaction temperatures. In the present...

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Abstract

The invention discloses a preparation method of 3-bromopropionitrile, wherein the preparation method comprises the following steps: taking acrylonitrile as a raw material, carrying out trimethylbromosilane intermolecular addition reaction, and distilling and purifying to obtain high-purity 3-bromopropionitrile. According to the method, cheap acrylonitrile is used as the raw material, and the high-purity 3-bromopropionitrile is obtained through the trimethylbromosilane intermolecular addition reaction and finally distillation and purification; the raw material is cheap and easy to obtain, and the method is suitable for commercial production, environmentally friendly, small in amount of generated three wastes and high in yield.

Description

technical field [0001] The invention relates to a preparation method, in particular to a preparation method of 3-bromopropionitrile. Background technique [0002] 3-Bromopropionitrile is an important pharmaceutical intermediate and fine chemical raw material. It is the starting material for the production of the antiviral drug didanosine, and it is also used as the raw material for the production of spermidine. The commonly used preparation method is that β-hydroxypropionitrile and phosphorus tribromide are added to react in benzene. After the reaction, the solvent benzene is evaporated, and then the reactant is distilled under reduced pressure to obtain the pure product of 3-bromopropionitrile. The main steps are as follows ( Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1977); p. 1914–1919). [0003] [0004] The main disadvantages of this process are: phosphorus tribromide is expensive, and a large amount of acid was...

Claims

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Application Information

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IPC IPC(8): C07C255/10C07C253/30C07C253/34
CPCC07C253/30C07C253/34C07C255/10
Inventor 颜林刘漫赵振宇李仟郭鹏
Owner ASTATECH CHENGDU BIOPHARM CORP
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