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Method for production of tricyclohexylphosphine

A technology of tricyclohexylphosphine and hexylphosphine oxide, which is applied in the production field of tricyclohexylphosphine, can solve the problems of high price, difficult preparation of catalyst niobium metal complexes, and dangerous use, and achieves improved yield, good application prospects, The effect of reducing production costs

Active Publication Date: 2012-08-08
PUYANG HUICHENG ELECTRONICS MATERIAL +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the synthesis method of tricyclohexylphosphine mainly adopts the organolithium method. In the organolithium method, the reaction temperature requirement is low, the yield is low, and the energy consumption is large. In addition, the organolithium is expensive and dangerous to use.
U.S. Patent US5530162A reports a method for directly using triphenylphosphine to synthesize tricyclohexylphosphine. The catalyst niobium metal complex used in this process is difficult to prepare and expensive, making it difficult to apply to industrial production

Method used

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  • Method for production of tricyclohexylphosphine

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Embodiment 1

[0019] In a 1L autoclave, add 278 g (1 mol) triphenylphosphine oxide, 13.9 g catalyst Pd / Al 2 o 3 and 300 mL of tetrahydrofuran, nitrogen replacement 3 times and hydrogen replacement 3 times, catalytic hydrogenation at a reaction temperature of 180 °C and a hydrogenation pressure of 6.0 MPa, the reaction was stopped after the GC detection was complete, and the catalyst was removed by filtration to obtain a tricyclohexylphosphine oxide solution .

[0020] Under the protection of Ar gas, add 162g (3 mol) KBH into 2 L reactor 4 and 100 mL of diethyl ether, 133.5 g (1 mol) of anhydrous AlCl at a reaction temperature of 20 °C 3 The diethyl ether (300 mL) solution was dropped into the reactor, and then the tricyclohexylphosphine oxide solution obtained above was dropped into the KBH at this temperature 4 -AlCl 3 In the system, after dropping, the temperature was raised to reflux and stirred overnight. When there was no tricyclohexylphosphine oxide in the sampling analysis, it wa...

Embodiment 2

[0027] In a 1L autoclave, add 278 g (1 mol) of triphenylphosphine oxide, 2.78 g of catalyst Rh / C and 300 mL of dioxane, and replace 3 times with nitrogen and 3 times with hydrogen, at a reaction temperature of 190 °C, Catalytic hydrogenation was carried out at a hydrogenation pressure of 10.0 MPa. The reaction was stopped after GC detection was complete, and the catalyst was removed by filtration to obtain a tricyclohexylphosphine oxide solution.

[0028] Under the protection of Ar gas, add 194.4g (3.6 mol) KBH into 2 L reactor 4 and 200 mL of diethyl ether, 160 g (1.2 mol) of anhydrous AlCl at a temperature of 30 °C 3 The diethyl ether (400 mL) solution was dropped into the reactor, and then the tricyclohexylphosphine oxide solution obtained above was dropped into the KBH at this temperature 4 -AlCl 3 In the system, after dropping, the temperature was raised to reflux and stirred overnight. When there was no tricyclohexylphosphine oxide in the sampling analysis, it was hydr...

Embodiment 3

[0031] In a 1L autoclave, add 278 g (1 mol) of triphenylphosphine oxide, 7.8 g of catalyst Ru / C and 300 mL of cyclohexane. After three times of nitrogen replacement and three times of hydrogen replacement, at a reaction temperature of 200 °C, add Catalyzed hydrogenation under a hydrogen pressure of 8.0 MPa, stopped after the reaction was complete as detected by GC, and filtered to remove the catalyst to obtain tricyclohexylphosphine oxide solution.

[0032] Under the protection of Ar gas, add 243 g (4.5 mol) KBH into the 2 L reactor 4 and 300 mL of diethyl ether, 200 g (1.5 mol) of anhydrous AlCl 3 The diethyl ether (600 mL) solution was dropped into the reactor, and then the tricyclohexylphosphine oxide solution obtained above was dropped into the KBH at this temperature 4 -AlCl 3 In the system, after dropping, the temperature was raised to reflux and stirred overnight. When there was no tricyclohexylphosphine oxide in the sampling analysis, it was hydrolyzed and the organ...

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Abstract

The invention discloses a method for production of tricyclohexylphosphine and belongs to the field of organic synthesis. The method comprises that triphenylphosphine oxide as an initial raw material undergoes a hydrogenation reaction in the presence of a catalyst to produce an intermediate tricyclohexylphosphine oxide; and the intermediate tricyclohexylphosphine oxide is reduced by KBH4-AlCl3 to form tricyclohexylphosphine. The method reduces a production cost, improves a product yield and is suitable for industrial production.

Description

technical field [0001] The invention relates to a production method of chemical products, in particular to a production method of tricyclohexylphosphine, belonging to the field of organic synthesis. Background technique [0002] Coupling reactions are widely used in the synthesis of natural products, functional materials, liquid crystals, drug molecules, and bioactive compounds. In recent years, with the rapid development of homogeneous catalytic technology, transition metal catalysts have been widely used in catalytic coupling reactions, and have attracted much attention due to their catalytic performance, such as high activity and good selectivity. In the research of transition metal catalysis, The structure and properties of phosphine ligands have an important impact on the catalytic performance of transition metals. Therefore, the design and synthesis of phosphine ligands has always been one of the important research contents in the research of transition metal catalyst...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/50
Inventor 杨振强李江涛王福玲杨瑞娜蒋卫鹏曲凤波周铎
Owner PUYANG HUICHENG ELECTRONICS MATERIAL
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