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Method for synthesizing di(3,5-dimethyl phenyl)phosphorus oxide

A technology of dimethyl phenyl and synthesis method, which is applied in the synthesis field of bis(3,5-dimethylphenyl) phosphorus oxide, can solve the problem of complicated injection chromatography operation, unfavorable promotion and utilization, large solvent loss, etc. problems, to achieve the effect of reducing production costs, improving core competitiveness, and improving yields

Inactive Publication Date: 2014-05-28
JIANGSU CHANGQING AGROCHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The average yield is only about 54%, and the injection chromatography operation is complicated, the production capacity is small, and the solvent loss is large, resulting in high cost
Not conducive to promotion and utilization

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] In a 1000ml reaction flask equipped with stirring, thermometer and reflux condenser, add 28.8g (1.2mol) Mg, 500mlTHF, 0.1g (0.4mmol) iodine and 63g (0.341mol) 3,5-dimethylbromobenzene, Raise the temperature to initiate the reaction, raise the temperature to 60°C, lower the temperature to 20-25°C, add 270g (1.46mol) 3,5-dimethylbromobenzene dropwise, after the dropwise addition, raise the temperature to 45°C for 4 hours, after the reaction, lower the temperature To -10~-5°C, add 55.2g (0.4mol) diethyl phosphite dropwise, after the dropwise addition, stir for 1 hour, and control the temperature at -5~0°C. After the reaction, adjust the pH to 1 with hydrochloric acid. 400ml of toluene was added for extraction and separation, the organic layer was precipitated to obtain a white solid, and 300ml of cyclohexane was added for recrystallization to obtain 68g of bis(3,5-dimethylphenyl)phosphorus oxide with a yield of 65.8%.

Embodiment 2

[0018] In a 1000ml reaction flask equipped with stirring, thermometer and reflux condenser, add 28.8g (1.2mol) Mg, 450mlTHF, 0.2g (0.8mmol) iodine and 54.6g (0.2951mol) 3,5-dimethylbromobenzene , the temperature is raised to initiate the reaction, the temperature rises to 55°C, the temperature is lowered to 25-30°C, 234g (1.2649mol) 3,5-dimethylbromobenzene is added dropwise, the dropwise addition is completed, and the temperature is raised to 50°C for 4 hours. After the reaction, Cool down to -10~-5°C, add 69g (0.5mol) of diethyl phosphite dropwise, after the dropwise addition, stir for 1 hour, keep the temperature at 0~5°C, after the reaction, adjust the pH to 1 with hydrochloric acid, add 500ml of toluene was extracted and separated, and the organic layer was precipitated to obtain a white solid, which was recrystallized by adding 350ml of cyclohexane to obtain 96.6g of bis(3,5-dimethylphenyl)phosphorus oxide with a yield of 74.9%.

Embodiment 3

[0020] In a 2000ml reaction flask equipped with stirring, thermometer and reflux condenser, add 57.6g (2.4mol) Mg, 1000mlTHF, 0.5g (2.0mmol) iodine and 84g (0.454mol) 3,5-dimethylbromobenzene, Raise the temperature to initiate the reaction, raise the temperature to 55°C, lower the temperature to 25-30°C, add 360g (1.946mol) 3,5-dimethylbromobenzene dropwise, after the dropwise addition, raise the temperature to 40°C for 4 hours, after the reaction, lower the temperature To -5~5°C, add 143.5g (1.04mol) diethyl phosphite dropwise, after the dropwise addition, stir for 1 hour, keep the temperature at 0~5°C, after the reaction, adjust the pH to 1 with hydrochloric acid, add 1200ml Toluene was extracted and separated, and the organic layer was precipitated to obtain a white solid, which was recrystallized by adding 800ml of cyclohexane to obtain 196.3g of bis(3,5-dimethylphenyl)phosphorus oxide, with a yield of 73.16%.

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Abstract

The invention discloses a method for synthesizing di(3,5-dimethyl phenyl)phosphorus oxide, and relates to the technical field of synthesis processes of a midbody of a hydrogenation catalyst diphosphine ligand of agriculture herbicide S-isopropyl alachlor. The method comprises the following steps: firstly, completely mixing Mg, tetrahydrofuran and iodine, adding a small amount of 3,5-dimentyl bromobenzene, heating to initialize reaction, raising the temperature of the mixing temperature to be 50-60 DEG C, cooling down, adding a great deal of 3,5-dimentyl bromobenzene, heating to ensure reaction of the mixing system at 45-50 DEG C till the reaction is accomplished, further cooling down, dropping diethyl phosphate, stirring to react till the reaction is accomplished, subsequently adjusting the pH value of the system after reaction to be 1 by using hydrochloric acid, further adding methylbenzene to extract and layer, desolventizing an organic layer to obtain white solid, and recrystalizing the white solid by using cyclohexane so as to obtain the di(3,5-dimethyl phenyl)phosphorus oxide. According to the method, operation steps of column chromatography and the like are eliminated, the capacity is increased, the yield is increased, the energy consumption is reduced, and the production cost is lowered.

Description

technical field [0001] The invention relates to the technical field of the synthesis process of bis(3,5-dimethylphenyl)phosphine oxide, an intermediate of the bisphosphine ligand of the hydrogenation catalyst of the agricultural herbicide S-isopropyl metolachlor. Background technique [0002] Bis(3,5-dimethylphenyl)phosphine oxide is an intermediate for the synthesis of the bisphosphine ligand of the hydrogenation catalyst of the agricultural herbicide S-isopropyl metolachlor. S-Metachlor is a selective herbicide that inhibits cell growth by hindering protein synthesis. Through the young shoots of plants, that is, the coleoptiles of monocotyledonous plants and the hypocotyls of dicotyledonous plants, the absorption and conduction is upward, and the absorption and conduction of seeds and root fluids are small, and the speed is slow. After emergence, it mainly relies on root absorption and upward conduction to inhibit the growth of young shoots and roots. Sensitive weeds are...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/53
Inventor 于国权王建荣吉志扬窦伟
Owner JIANGSU CHANGQING AGROCHEMICAL CO LTD
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