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Novel process for synthesizing methyl benzoylformate from benzoyl cyanide

A technology of benzoylformic acid and benzoyl cyanide, which is applied in the new process field of synthesizing methyl benzoylformate from benzoyl cyanide, can solve the problems of unfavorable industrial production, high energy consumption of solvent recovery, and increase of waste acid water volume, etc. , to achieve the effect of eliminating potential safety hazards, mild conditions, and rapid response

Inactive Publication Date: 2017-12-15
安道麦股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The melting point of the raw material benzoyl cyanide in this process route is 29-32°C, and it is easy to solidify at low temperature, which is not conducive to the reaction; the intermediate product iminosulfate will violently crystallize and exotherm, stick to the wall, and solidify the material in a short time, etc. problem, there is a great potential safety hazard, which is not conducive to industrial production
[0004] Nantong Dehexi Chemical Co., Ltd. solved the low-temperature curing problem of benzoyl cyanide by adding the solvent methyl benzoate, but the recovery of the solvent in the post-treatment consumes a lot of energy and the yield is low (88-90%)
[0005] Some companies have solved the fluidity problem of the intermediate product iminosulfuric acid ester synthesis process by increasing the proportion of concentrated sulfuric acid, but the amount of waste acid water produced is greatly increased, and the yield is low (85-88%)

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] In the reactor of 500mL, add 133.8g 98% benzoyl cyanide (1mol), 5.85g sodium chloride (0.01mol), 0.5g triethylbenzyl ammonium chloride (0.0022mol), 60ml xylene (0.49mol ), keep adding 127.5g concentration of 85% concentrated sulfuric acid dropwise at 20°C for 1 hour (1.11mol), heat up to 40°C for 1 hour; add 61ml methanol (1.51mol) dropwise at 40°C for 0.5 hour, heat up to 70°C for 3 hours Hours, the reaction was stopped, and the methanol was distilled off. Add 90 g of water, separate the acid water, add 160 g of water to the oil layer, wash twice to obtain a crude product, and rectify under reduced pressure to obtain 164.16 g of methyl benzoylformate, with a content of 90% and a yield of 90%.

Embodiment 2

[0028] In the reactor of 500mL, add 133.8g 98% benzoyl cyanide (1mol), 1g sodium bromide (0.01mol), 0.7g tetrabutylammonium bromide (0.0022mol), 65ml toluene (0.75mol), keep in Add 127.5g of 85% concentrated sulfuric acid (1.11mol) dropwise at 20°C for 1 hour, heat up to 40°C for 1 hour; add 85ml of methanol (2.10mol) dropwise at 40°C for 1 hour, heat up to 85°C for 3 hours, and stop the reaction , methanol was distilled off. Add 90 g of water, separate the acid water, add 160 g of water to the oil layer, wash twice to obtain the crude product, and rectify under reduced pressure to obtain 165.94 g of methyl benzoylformate with a content of 92% and a yield of 93%.

Embodiment 3

[0030] Add 133.8g 98% benzoyl cyanide (1mol), 6.4g ammonium chloride (0.012mol), 0.7g tetrabutylammonium bromide (0.0022mol), 67ml xylene (0.54mol) in the reactor of 500mL, Keep at 20°C and add 160 grams of 85% concentrated sulfuric acid (1.39mol) dropwise for 1 hour, heat up to 40°C for 1 hour; add 100ml methanol (2.47mol) dropwise at 40°C for 1.5 hours, heat up to 90°C for 3 hours, The reaction was stopped and methanol was distilled off. Add 90 g of water, separate the acid water, add 160 g of water to the oil layer, wash twice to obtain a crude product, and rectify under reduced pressure to obtain 165.91 g of methyl benzoylformate, with a content of 94% and a yield of 95%.

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Abstract

The invention discloses a novel process for synthesizing methyl benzoylformate from benzoyl cyanide. The novel process comprises the following steps: dissolving benzoyl cyanide in an organic solvent, adding a halide catalyst and a phase transfer catalyst, lasting for 5-60 minutes at a temperature of 5-20 DEG C, adding dropwise concentrated sulfuric acid to the system, and carrying out thermal reaction for 0.5-5 hours at a temperature of 20-40 DEG C to obtain an intermediate iminosulfate compound; and lasting for 5-60 minutes at a temperature of 30-50 DEG C, adding dropwise methyl alcohol to the system, and carrying out thermal reaction for 0.5-5 hours at a temperature of 50-100 DEG C to obtain methyl benzoylformate. In the novel process disclosed by the invention, the reaction at a low temperature is accelerated obviously by using suitable solvents and composite catalysts, so that the potential safety hazard in industrialized production is eliminated, the stability of production is improved, the energy consumption is reduced, and the yield is up to 96%.

Description

technical field [0001] The invention relates to the field of fine chemicals, in particular to a new process for synthesizing methyl benzoylformate from benzoyl cyanide. Background technique [0002] Methyl benzoylformate is a compound containing carbonyl, carboxylic acid and ester groups. Due to its multiple active groups, it exhibits special properties and can synthesize important biologically active compounds. It is often used in organic synthesis, photoinitiated It is an important intermediate in the synthesis of medicine and pesticide. [0003] The production method of methyl benzoylformate mainly adopts benzoyl cyanide as raw material at present, further acidolysis, esterification obtains methyl benzoylformate. The melting point of the raw material benzoyl cyanide in this process route is 29-32°C, and it is easy to solidify at low temperature, which is not conducive to the reaction; the intermediate product iminosulfate will violently crystallize and exotherm, stick to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/738C07C67/18C07C305/00C07C303/24
CPCC07C67/18C07C303/24C07C305/00C07C69/738
Inventor 刘安平殷宏陈林薛光才姚新沈佩张剑
Owner 安道麦股份有限公司
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