Method for preparing triphenylphosphine in reducing manner

A technology for triphenylphosphine and triphenylphosphine oxide, which is applied in the field of reduction preparation of triphenylphosphine, can solve the problems of rare reaction raw materials, harsh reaction conditions, inability to regenerate reducing agents, etc., and achieves high catalytic efficiency and low catalyst amount. , the effect of less catalyst dosage

Active Publication Date: 2018-08-17
江苏富比亚化学品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned reduction method of triphenylphosphine oxide has the following disadvantages: (1) the raw materials for the reaction are rare and the reaction conditions are harsh;

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Put 27.8g triphenylphosphine oxide, 88.2g diphenylphosphine chloride (mass ratio 1:3.17), 0.56g trifluoromethanesulfonic acid (triphenylphosphine oxide) into the 250mL reaction flask replaced by nitrogen 2% of the mass), the temperature was raised to 150° C., and the temperature was maintained for 12 hours. After cooling to room temperature, turn on the vacuum pump, and after the vacuum reaches 0.098Mpa, slowly raise the temperature, and intercept the mixture of diphenylphosphine chloride and diphenylphosphinyl chloride. After the high boiler is cooled, 50g of toluene is put into it, washed with saturated sodium carbonate to neutrality, the organic layer is washed twice with deionized water, the organic layer is separated, after the toluene is recovered by distillation, 30g of ethanol is put into the bottle, and recrystallized to obtain three 23.6 g of phenylphosphine, the yield is 90%, and the content detected by HPLC is 98.7%.

Embodiment 2

[0045] Put 27.8g triphenylphosphine oxide, 71.6g phenylphosphine dichloride (the mass ratio of the two is 1:2.58), 0.56g trifluoromethanesulfonic acid (triphenylphosphine oxide) into the 250mL reaction flask replaced by nitrogen 2% of the mass), the temperature was raised to 150° C., and the temperature was maintained for 12 hours. After cooling to room temperature, turn on the vacuum pump, and after the vacuum reaches 0.098Mpa, slowly raise the temperature, and intercept the mixture of phenylphosphine dichloride and phenylphosphonodichloride. After the high boiler is cooled, 50g of toluene is put into it, washed with saturated sodium carbonate to neutrality, the organic layer is washed twice with deionized water, the organic layer is separated, after the toluene is recovered by distillation, 30g of ethanol is put into the bottle, and recrystallized to obtain three 21.6 g of phenylphosphine, the yield is 82.4%, and the content detected by HPLC is 98.5%.

Embodiment 3

[0047] Put 27.8g triphenylphosphine oxide, 88.2g diphenylphosphine chloride (mass ratio of the two 1:3.17), 0.56g diphenylphosphonic acid (triphenylphosphine oxide) into the 250mL reaction flask replaced by nitrogen 2% of the mass), the temperature was raised to 150° C., and the temperature was maintained for 12 hours. After cooling to room temperature, turn on the vacuum pump, and after the vacuum reaches 0.098Mpa, slowly raise the temperature, and intercept the mixture of diphenylphosphine chloride and diphenylphosphinyl chloride. After the high boiler is cooled, 50g of toluene is put into it, washed with saturated sodium carbonate to neutrality, the organic layer is washed twice with deionized water, the organic layer is separated, after the toluene is recovered by distillation, 30g of ethanol is put into the bottle, and recrystallized to obtain three 18.4 g of phenylphosphine, the yield is 70%, and the content detected by HPLC is 97.8%.

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Abstract

The invention provides a method for preparing triphenylphosphine in a reducing manner. Phenylphosphonicdichloride or chlorodiphenylphosphine is used as a reducing agent, and raw materials are low in price and easily obtained; under the effect of a catalyst, the phenylphosphonicdichloride or chlorodiphenylphosphine and triphenylphosphine oxide are subjected to reducing reaction, stabilities of phosphine oxygen double bonds in the triphenylphosphine oxide and oxidation products (phenylphosphonic dichloride or diphenylphosphinyl chloride) of a reducing agent are different, the stabilities of thedouble bonds of the phenylphosphonic dichloride and the diphenylphosphinyl chloride are good, the double bonds of the triphenylphosphine oxide are broken under the effect of the catalyst, the double bonds of the formed phenylphosphonic dichloride and the formed diphenylphosphinyl chloride are not easily damaged by the catalyst, and therefore, triphenylphosphine can be obtained under gentle conditions; the oxidation products (the phenylphosphonic dichloride or the diphenylphosphinyl chloride) of the reducing agent are important organic synthesis intermediate (such as synthesis of organic phosphate); and moreover, the amount of the catalyst required in the method is small, and the catalysis efficiency is high.

Description

technical field [0001] The invention relates to the technical field of compound preparation, in particular to a method for reducing and preparing triphenylphosphine. Background technique [0002] Organophosphine compounds and their derivatives are widely used in life science and chemical industry, especially triphenylphosphine, which plays an important role in organometallic catalysis and many classic organic reactions, such as witting reaction, Appel response etc. However, the reaction is often accompanied by the formation of triphenylphosphine oxide as a by-product, so how to eliminate by-products or realize the effective utilization of useless by-products has attracted more and more attention. Among them, the reduction of triphenylphosphine oxide to triphenylphosphine is an effective method to increase the added value of the reaction. [0003] At present, the reduction methods of triphenylphosphine oxide mainly contain: (1) phosphorus and phosgene method; (2) borane met...

Claims

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Application Information

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IPC IPC(8): C07F9/50
CPCC07F9/5022C07F9/509
Inventor 段好东张召举李焕成王祥王忠卫
Owner 江苏富比亚化学品有限公司
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