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A kind of diphenylfoscumyl ester and its synthetic method

A synthesis method and technology of diphenylphosphine, which are applied in the field of phosphite antioxidants, can solve problems such as poor thermal stability and hydrolytic stability, complicated operation steps, and increased product cost, and achieve high processing stability and simplified Operating procedure, effect of high thermal decomposition temperature

Active Publication Date: 2017-02-01
QINGDAO TECHN COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, PEPQ is a phosphonite auxiliary antioxidant with a P-C bond. Its advantages are high heat resistance and hydrolysis resistance. Its application in polypropylene can increase the effect of many light stabilizers by about 30%. Others Because there is no P-C bond in the product structure, the thermal stability and hydrolytic stability are poor
[0003] Among the published synthesis methods of phosphite compounds, for example, an antioxidant phenylphosphinate bis(2,4-di-tert-butylphenol) disclosed in Chinese Patent Application No. 2012104740114 and its preparation method and application, Acid-binding agents such as triethylamine, N, N-dimethylaniline, and pyridoxine are all used. After the reaction, operations such as suction filtration, washing, and filtration are first required to remove the amine salts generated, and then the amine salts in the filtrate are evaporated. Solvent, the product is obtained by washing with an organic solvent for many times, and the operation steps are complicated
On the one hand, the addition of acid-binding agents will introduce amine impurities, which will affect the quality and complicate the operation; on the other hand, it will increase the cost of the product

Method used

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  • A kind of diphenylfoscumyl ester and its synthetic method
  • A kind of diphenylfoscumyl ester and its synthetic method
  • A kind of diphenylfoscumyl ester and its synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 31.4 grams of cumol and 100 ml of toluene into a 500 ml three-necked flask, and pass in nitrogen gas. After stirring evenly, slowly add a mixture of 22 grams of diphenylphosphine chloride and 20 mL of toluene under the condition of controlling the temperature at 80°C. , kept at 80°C for 4 hours, lowered the temperature, stopped passing nitrogen, evaporated toluene under reduced pressure to obtain a yellow viscous substance, added 40mL of ethanol / acetone (V / V=1:1) and 0.5g of activated carbon, refluxed for 30 minutes, and After hot filtration and cooling, the precipitated solid was filtered and dried to obtain the product with a yield of 85.3% based on diphenylphosphine chloride. The product is analyzed by liquid chromatography with a purity of 99.3%, a 1% thermal weight loss temperature of 351°C, and a phosphorus content of 6.06%.

Embodiment 2

[0030] Add 31.4 grams of cumol and 100 ml of toluene into a 500 ml three-necked flask, pass in nitrogen gas, stir evenly, and slowly add a mixture of 22 grams of diphenylphosphine chloride and 20 ml of toluene under the condition of controlling the temperature at 80°C. , heat up to 100°C and keep warm for 10 hours, cool down, stop nitrogen flow, evaporate toluene under reduced pressure to obtain a yellow sticky substance, add 40mL of ethanol / acetone (V / V=1:1) and 0.5g of activated carbon, and keep at reflux for 30 minutes , filtered while hot, and after cooling, the precipitated solid was filtered and dried to obtain the product, and the yield was 92.6% based on diphenylphosphine chloride. The product is analyzed by liquid chromatography with a purity of 99.4%, a 1% thermal weight loss temperature of 352°C, and a phosphorus content of 6.02%.

Embodiment 3

[0032] Add 31.4 grams of cumol and 100 ml of benzene into a 500 ml three-necked flask, and pass in nitrogen gas. After stirring evenly, slowly add a mixture of 22 grams of diphenylphosphine chloride and 20 ml of benzene under the condition of controlling the temperature at 100°C. , kept at 100°C for 4 hours, lowered the temperature, stopped passing nitrogen, evaporated toluene under reduced pressure to obtain a yellow viscous substance, added 40mL of ethanol / acetone (V / V=1:1.5) and 0.5g of activated carbon, refluxed for 30 minutes, while After hot filtration and cooling, the precipitated solid was filtered and dried to obtain the product with a yield of 88.7% based on diphenylphosphine chloride. The product is analyzed by liquid chromatography with a purity of 99.1%, a 1% thermal weight loss temperature of 349°C, and a phosphorus content of 6.10%.

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Abstract

The invention discloses diphenylphosphine cumyl phenolic ester and a synthetic method thereof. According to the method, shielding gas is introduced into a mixture of 2,4-bis(1-methyl-1-phenylethyl)-pheno and a solvent, mixed liquid of chlorodiphenylphosphine and solvents is added in a dripping mode, and thermal reaction is carried out after addition; after the thermal reaction is over, the protective gas is stopped from being introduced, temperature is lowered, the solvents are removed through distilling at normal pressure or lower pressure, and light yellow thick liquid is obtained; a crystallizing agent is added to the thick liquid, then a proper amount of activated carbon is added, heat preservation is carried out for 30 min in a reflux state, filtration is carried out at a high temperature, white solid is separated after filtered liquid is cooled, and the diphenylphosphine cumyl phenolic ester is obtained after filtering and drying. The synthetic process overcomes the defect that acid-binding agents are used in conventional phosphite ester compound synthesis reaction, by-products generated due to the reaction are actively extruded by the introduced protective gas, and the procedures of suction filtration, washing, generated amine salt filtration and removal and the like are omitted. Besides, the diphenylphosphine cumyl phenolic ester is directly separated by means of the crystallizing agents, so that the environment pollution problem caused due to the fact that the diphenylphosphine cumyl phenolic ester is obtained through multiple times of washing by means of organic solvents in the prior art is solved.

Description

technical field [0001] The invention relates to the technical field of organic chemistry, in particular to phosphite antioxidants. Background technique [0002] Phosphite antioxidants are widely used in the plastics industry and rubber industry. There are many types of antioxidants on the market, such as the antioxidant tris(2,4-di-tert-butylphenol) phosphite (code AO168), antioxidant dioctadecyl pentaerythritol diphosphite, tetrakis(2,4-di-tert-butylphenyl)-4,4`-biphenyl diphosphite (code PEPQ), Antioxidant cumyl pentaerythritol bisphosphite (code AO9228), etc. Among them, PEPQ is a phosphonite auxiliary antioxidant with a P-C bond. Its advantages are high heat resistance and hydrolysis resistance. Its application in polypropylene can increase the effect of many light stabilizers by about 30%. Others Because there is no P-C bond in the product structure, the variety has poor thermal stability and hydrolytic stability. [0003] Among the published synthesis methods of pho...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/46C08K5/5377
Inventor 李艳
Owner QINGDAO TECHN COLLEGE