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Preparation method of tricyclohexyl phosphine

A technology of tricyclohexylphosphine and cyclohexyl Grignard, which is applied in the field of preparation of tricyclohexylphosphine, can solve the problems of low product purity, low product yield, complicated processing and the like, and achieves simple post-processing, mild reaction conditions, Operational safety effect

Active Publication Date: 2013-01-16
PANJIN GELIN KAIMO TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The post-processing of this method is more complicated, and there are still problems such as low product yield and low product purity.

Method used

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  • Preparation method of tricyclohexyl phosphine
  • Preparation method of tricyclohexyl phosphine
  • Preparation method of tricyclohexyl phosphine

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preparation example Construction

[0034] 1. Preparation of Cyclohexyl Grignard Reagent

[0035] Under the protection of an inert gas such as nitrogen, magnesium chips and an organic solvent such as anhydrous tetrahydrofuran (THF) or anhydrous methyl tetrahydrofuran are added to the reaction vessel, the magnesium chips are slightly excessive, and the organic solvent can immerse the magnesium chips. Add a few grains of iodine, start the mechanical stirring, add the organic solvent solution of halocyclohexane such as anhydrous THF or anhydrous methyl tetrahydrofuran solution at 50-65°C, first add a small amount dropwise, after the Grignard reaction is triggered, then drop Add, the temperature is maintained at about 50-65 ° C, after the dropwise addition is completed, keep warm and stir. The reaction holding temperature is controlled at 30-70°C, preferably 45-65°C, and the holding time is controlled at 8-16 hours, preferably 12-16 hours.

[0036] 2. Preparation of Tricyclohexylphosphine

[0037] Lower the tempe...

Embodiment 1

[0048]Replace the reaction bottle with a nitrogen atmosphere, add 12.8g of analytically pure magnesium chips and anhydrous THF, and just immerse the magnesium chips in THF. Add 1-2 grains of iodine, start mechanical stirring, add 200mL of anhydrous THF solution of 59.3g of analytically pure chlorocyclohexane at 60°C, first drop 20mL and then stop the dropwise addition, after the Grignard reaction is triggered, then add dropwise , the temperature was maintained at 60°C, and after the dropwise addition was completed, it was stirred at 45°C for 12 hours.

[0049] The temperature of the reaction solution was lowered to 15°C, and 22g of analytically pure PCl was added dropwise 3 150 mL of anhydrous THF solution, the temperature was controlled at 25°C, and after the dropwise addition was completed, it was kept at 45°C for 1 hour.

[0050] After cooling down to room temperature, add saturated NH dropwise in an ice-water bath 4 Cl aqueous solution until the reaction liquid was clear...

Embodiment 2

[0057] Replace the reaction bottle with a nitrogen atmosphere, add 12.8g of analytically pure magnesium chips and anhydrous THF, and just immerse the magnesium chips in THF. Add 1-2 grains of iodine, start mechanical stirring, add 200mL of anhydrous THF solution of 59.3g of analytically pure chlorocyclohexane at 60°C, first drop 20mL and then stop the dropwise addition, after the Grignard reaction is triggered, then add dropwise , the temperature was maintained at 60°C, and after the dropwise addition was completed, it was stirred at 60°C for 16 hours.

[0058] The temperature of the reaction solution was lowered to 15°C, and 22g of analytically pure PCl was added dropwise 3 150 mL of anhydrous THF solution, the temperature was controlled at 25°C, and after the dropwise addition was completed, it was kept at 40°C for 2 hours.

[0059] After cooling down to room temperature, add saturated NH dropwise in an ice-water bath 4 Cl aqueous solution until the reaction liquid was cle...

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Abstract

The invention relates to a preparation method of tricyclohexyl phosphine, which comprises the following steps: reacting a cyclohexyl Grignard reagent and phosphorus trihalide, dropwisely adding a saturated strongly-acidic weakly-alkaline inorganic salt water solution at low temperature to carry out quenching, adding tetrafluoroboric acid to prepare a salt, and resolving the salt with triethylamine to obtain the tricyclohexyl phosphine, wherein the cyclohexyl Grignard reagent is prepared by carrying out Grignard reaction on halogenated cyclohexane and magnesium metal under inert gas shielding. According to the invention, the product is subjected to after-treatment by a chemical process; the tetrafluoroboric acid firstly reacts with tricyclohexyl phosphine to form a salt to completely extract the tricyclohexyl phosphine from the reaction solution, and the salt is resolved with the triethylamine. The invention has very obvious beneficial effects, and greatly enhances the preparation yield; and the prepared product has the advantages of high purity, high quality and low preparation cost.

Description

technical field [0001] The invention relates to a preparation method of tricyclohexylphosphine, which belongs to the technical field of organic synthesis. Background technique [0002] Tricyclohexylphosphine plays a wide role in modern organic synthesis and practical applications. It is mainly used as a ligand in coupling reactions such as Buchwald and Suzuki. It is used in organic catalysts, transition metal complex catalysts, sunscreens, and photofunctional complexes. It has a very wide range of applications in the synthesis of substances such as In the synthesis of these substances, it is especially required that tricyclohexylphosphine has higher purity and better quality. [0003] So far, in order to obtain tricyclohexylphosphine with high purity and high yield, many preparation schemes of tricyclohexylphosphine have been proposed and tried. It is reported in the literature that cyclohexyl Grignard reagent is used to react with phosphorus trichloride. After the reactio...

Claims

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Application Information

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IPC IPC(8): C07F9/50
Inventor 宫宁瑞
Owner PANJIN GELIN KAIMO TECH CO LTD
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