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Novel solvent-free synthesis method of 2, 4, 6-trimethylbenzoyl phenyl ethyl hypophosphite

A technology of trimethylbenzoylbenzene and ethyl hypophosphite, applied in the chemical industry, can solve the problem that ethyl chloride cannot be discharged from the reaction system in time, reduce the utilization rate of raw materials, product purity, product yield and purity Reduce and other problems to ensure quality, improve yield and purity, and achieve the effect of easy operation

Inactive Publication Date: 2020-09-11
宁波海曙琼杰化工技术研发工作室
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The current process for synthesizing ethyl 2,4,6-trimethylbenzoylphenylphosphinate has the disadvantages of harsh reaction conditions, excessive production of three wastes, and low product quality.
For example, the invention patent with the publication number CN103333203A discloses a preparation method of 2,4,6-trimethylbenzoylphenylphosphinate ethyl ester, which first uses toluene as a solvent, triethylamine as an acid-binding agent, and Anhydrous ethanol and phenyl phosphorus dichloride are used as reaction raw materials to react at low temperature to synthesize the intermediate product diethyl phenylphosphinate, and then use toluene as solvent, diethyl phenylphosphinate and 2,4, 6-trimethylbenzoyl chloride is used as a raw material reaction to synthesize 2,4,6-trimethylbenzoylphenylphosphinate ethyl ester under low vacuum conditions. This method introduces toluene as a solvent in the synthesis process, not only It will lead to an increase in the three wastes produced, which is not clean and environmentally friendly, and the presence of toluene will make the ethyl chloride produced in the reaction process unable to be discharged from the reaction system in time, resulting in a Michelle reaction between ethyl chloride and the raw material phenyl phosphorus dichloride. -Albuzov reaction, thereby reducing the utilization rate of raw materials and the purity of the product; in addition, the method adopts the mode of conventional vacuum distillation to 2,4,6-trimethylbenzoylphenylphosphinate ethyl ester after reaction finishes The crude product is post-treated, which will make the heat-sensitive substance 2,4,6-trimethylbenzoylphenylphosphite ethyl ester time in a high temperature state and easily decompose, resulting in a decrease in the yield and purity of the product

Method used

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  • Novel solvent-free synthesis method of 2, 4, 6-trimethylbenzoyl phenyl ethyl hypophosphite
  • Novel solvent-free synthesis method of 2, 4, 6-trimethylbenzoyl phenyl ethyl hypophosphite

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Experimental program
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Embodiment 1

[0029] A new solvent-free synthetic method of 2,4,6-trimethylbenzoylphenylphosphinate ethyl ester, comprising the steps of:

[0030] (1) 220g (4.775mol) of absolute ethanol and 403g (4.908mol) of N-methylimidazole were added to the reaction flask, stirred, and 398g (2.224mol) of phenyl dichloride was added dropwise to the reaction flask at 45°C Phosphate, after the dropwise addition, the temperature was raised to 80°C, and the reaction was carried out at a constant temperature for 45 minutes. After the reaction was completed, it was allowed to stand for stratification, and the supernatant was taken and distilled at night to obtain the intermediate product phenyldiethoxyphosphine;

[0031] (2) 397g (2.003mol) of the intermediate product phenyldiethoxyphosphine obtained in step (1) was added to the reaction flask, stirred, and 383g (2.097mol) was added dropwise to the reaction flask at -0.098Mpa and 45°C. ) 2,4,6-trimethylbenzoyl chloride, after the dropwise addition, the temper...

Embodiment 2

[0033] A new solvent-free synthetic method of 2,4,6-trimethylbenzoylphenylphosphinate ethyl ester, comprising the steps of:

[0034] (1) Add 109g (2.366mol) of absolute ethanol and 194g (2.363mol) of N-methylimidazole into the reaction flask, stir, and add 179g (1.000mol) of phenyl dichloride dropwise to the reaction flask at 30°C Phosphate, after the dropwise addition, the temperature was raised to 70°C, and the reaction was carried out at a constant temperature for 60 minutes. After the reaction was completed, the mixture was allowed to stand for stratification, and the supernatant was taken and distilled at night to obtain the intermediate product phenyldiethoxyphosphine;

[0035] (2) 198g (0.999mol) of the intermediate product phenyldiethoxyphosphine obtained in step (1) was added to the reaction flask, stirred, and 183g (1.002mol) was added dropwise to the reaction flask at -0.098Mpa and 40°C. ) 2,4,6-trimethylbenzoyl chloride, after the dropwise addition, the temperature...

Embodiment 3

[0037] A new solvent-free synthetic method of 2,4,6-trimethylbenzoylphenylphosphinate ethyl ester, comprising the steps of:

[0038] (1) Add 94g (2.040mol) of absolute ethanol and 172g (2.095mol) of N-methylimidazole into the reaction flask, stir, and drop 179g (1.000mol) of phenyl dichloride into the reaction flask at 60°C Phosphate, after the dropwise addition was completed, the temperature was raised to 90°C, and the reaction was carried out at a constant temperature for 30 minutes. After the reaction was completed, the mixture was allowed to stand for stratification, and the supernatant was taken and distilled at night to obtain the intermediate product phenyldiethoxyphosphine;

[0039](2) 198g (0.999mol) of the intermediate product phenyldiethoxyphosphine obtained in step (1) was added to the reaction flask, stirred, and 200g (1.095mol) was added dropwise to the reaction flask at -0.098Mpa and 50°C ) 2,4,6-trimethylbenzoyl chloride, after the dropwise addition, the temper...

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Abstract

The invention discloses a novel solvent-free synthesis method of 2, 4, 6-trimethylbenzoyl phenyl ethyl hypophosphite, and belongs to the technical field of chemical engineering. The method comprises the following steps: firstly, adding absolute ethyl alcohol and N-methylimidazole into a reaction flask, dropwise adding phenyl phosphorus dichloride into the reaction flask at 30-60 DEG C, heating to70-90 DEG C after dropwise adding is completed, carrying out a constant-temperature reaction for 30-60 minutes, standing for layering after the reaction is completed, taking supernate, and distillingto obtain intermediate product phenyl diethoxyphosphine; then, adding the phenyl diethoxyphosphine into the reaction flask, dropwise adding 2, 4, 6-trimethylbenzoyl chloride into the reaction flask under the high vacuum condition of-0.098 Mpa to-0.98 Mpa and at the temperature of 40 DEG C to 50 DEG C, increasing the temperature to 80 DEG C to 90 DEG C after dropwise adding is completed, conductinga constant-temperature reaction for 1 h to 3 h, and then purifying to obtain the target product 2, 4, 6-trimethylbenzoyl phenyl ethyl hypophosphite. The method is simple and convenient to operate, mild in reaction condition, clean and environment-friendly, and the product synthesized by the method is high in yield and purity.

Description

technical field [0001] The invention relates to a new solvent-free synthesis method of ethyl 2,4,6-trimethylbenzoylphenylphosphinate, which belongs to the technical field of chemical industry. Background technique [0002] 2,4,6-Trimethylbenzoylphenylphosphinate ethyl ester is a liquid high-efficiency free radical photoinitiator, which is easy to use, fast curing speed, good yellowing resistance, and its application fields are increasing year by year big. [0003] The current process for synthesizing ethyl 2,4,6-trimethylbenzoylphenylphosphinate has the disadvantages of harsh reaction conditions, excessive waste generation and low product quality. For example, the invention patent with the publication number CN103333203A discloses a preparation method of 2,4,6-trimethylbenzoylphenylphosphinate ethyl ester, which first uses toluene as a solvent, triethylamine as an acid-binding agent, and Anhydrous ethanol and phenyl phosphorus dichloride are used as reaction raw materials ...

Claims

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Application Information

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IPC IPC(8): C07F9/48C07F9/32
CPCC07F9/3241C07F9/3264C07F9/4841
Inventor 刘碧见
Owner 宁波海曙琼杰化工技术研发工作室