Preparation method of trialkyl phosphine borofluoride

A technology of alkylphosphine fluoroborate and fluoroboric acid, which is applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc., and can solve bad smell, unfriendly environment, purchase restrictions, etc. problems, to achieve the effect of convenient use and storage, simple method and wide application

Inactive Publication Date: 2013-04-03
DALIAN NETCHEM CHIRAL TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] The currently known synthetic method of trialkylphosphine basically adopts the reaction of phosphorus trichloride and Grignard reagent. After the reaction is completed, the ammonium chloride is quenched, and the oil layer is separated, and the trialkylphosphine generated is obtained by distilling off the solvent. This method has many defects: (1) Phosphorus trichloride is highly poisonous, and its purchase is subject to certain restrictions; (2) The product alkylphosphine is easily oxidized by air to trialkylphosphine oxide. smell; (3) more wastes are produced; (4) not suitable for long-term storage
Trialkylphosphine has a strong smell and is not friendly to the environment
Many trialkylphosphines are sensitive to air. This process limits the synthesis of such trialkylphosphines and is not universal

Method used

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  • Preparation method of trialkyl phosphine borofluoride
  • Preparation method of trialkyl phosphine borofluoride

Examples

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example 1

[0018] A method for preparing trialkylphosphine fluoroborate, the raw material alkyl Grignard reagent reacts with phosphorus tribromide at low temperature, after adding fluoroboric acid to form a salt, extraction, concentration, recrystallization, and cooling to precipitate trialkylphosphine fluoroboron salt.

[0019] Reaction mechanism of the present invention is as follows:

[0020]

[0021] In the formula, R: alkyl or aromatic hydrocarbon group.

[0022] Specific process:

[0023] Add 76.8g magnesium and 300g cyclohexyl chloride tetrahydrofuran solution to a 2000 mL round bottom flask equipped with a nitrogen protection device and mechanical stirring. Control the temperature ≤ 40°C, add iodine to trigger, add cyclohexyl chloride tetrahydrofuran solution dropwise with a constant pressure dropping funnel, control the temperature at 60-65°C, after the addition is complete, stir and reflux for 2 hours. Under the protection of argon, configure 110.2g of phosphorus tribro...

Embodiment 2

[0025] A method for preparing trialkylphosphine fluoroborate, which is the same as the method and reaction mechanism of Example 1, and the specific process:

[0026] Under the protection of nitrogen, add 7.28g (1.05eq) magnesium chips and 15.2g (1 / 8 of the total weight) chlorobutane THF solution (26.7g chlorocyclohexane dissolved in 135mL THF) into a 250mL four-necked bottle , heat up to 55-60°C, add 2 grains of iodine to trigger successfully, add dropwise the remaining 105.5g (total 1.0eq) chlorobutane tetrahydrofuran solution, while maintaining boiling reflux, after the dropwise addition, heat to reflux for 2h, Cool down to room temperature for later use, and analyze and measure the concentration to be 1.82±0.3mmol / g (about 154g). In a 500mL four-neck flask, under the protection of argon, put 7.5g (0.182eq) of phosphorus tribromide and 70mLTHF, and stir at room temperature. 988mg (0.0182eq) of cuprous iodide and 898mg (0.0364eq) of lithium bromide, lower the temperature to -...

Embodiment 3

[0029] A method for preparing trialkylphosphine fluoroborate, which is the same as the method and reaction mechanism of Example 1, and the specific process:

[0030] Under the protection of nitrogen, add 24.3g (1.05eq) magnesium chips and 60.8g (one-eighth of the total weight) chlorobutane THF solution (88g chlorocyclohexane dissolved in 450mL THF) into a 1000mL four-necked bottle, Heat up to 55-60°C, add 2 grains of iodine to trigger successfully, add dropwise the remaining tert-chlorobutane solution while maintaining boiling reflux, after the dropwise addition, heat to reflux for 2 hours, cool down to room temperature for later use, under nitrogen protection, Prepare 47.8g of phosphorus tribromide and 226mLTHF (water content 0.01%), cool down to -20°C with dry ice ethanol, add the Grignard reagent dropwise to phosphorus trichloride, control the temperature at -15°C to -10°C, and complete the dropwise addition After that, raise the temperature to room temperature, stir for 3 ...

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PUM

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Abstract

The invention discloses a preparation method of trialkyl phosphine borofluoride. The preparation method comprises the following steps of: reacting a raw material, alkyl Grignard reagent, with phosphorus tribromide at a lower temperature; adding fluoboric acid into the obtained object for salification; and carrying out extraction, concentration and recrystallization on the obtained product, and cooling the obtained product so as to separate out the trialkyl phosphine borofluoride. The preparation method disclosed by the invention is simple and easy to implement, is safe and environmental-friendly, and is low in cost; the yield of the trialkyl phosphine borofluoride prepared by the method with the alkyl Grignard reagent and phosphorus tribromide is high and can be up to 49%-55%, and an organic solvent extracted in the reaction can be directly recycled. The method disclosed by the invention also has the innovation that trialkyl phosphine compounds sensitive to air are converted into borofluoride with stable properties in air, and the trialkyl phosphine borofluoride is convenient to use and store and has a wide application range.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, in particular to a synthesis method for preparing trialkylphosphine fluoroborate. Background technique [0002] The currently known synthetic method of trialkylphosphine basically adopts the reaction of phosphorus trichloride and Grignard reagent. After the reaction is completed, the ammonium chloride is quenched, and the oil layer is separated, and the trialkylphosphine generated is obtained by distilling off the solvent. This method has many defects: (1) Phosphorus trichloride is highly poisonous, and its purchase is subject to certain restrictions; (2) The product alkylphosphine is easily oxidized by air to trialkylphosphine oxide. smell; (3) more wastes are produced; (4) not suitable for long-term storage. Trialkylphosphine has a strong odor and is not friendly to the environment. Multiple washings to remove impurities will generate a large amount of waste water, which no...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/50
Inventor 才连金刘启宾
Owner DALIAN NETCHEM CHIRAL TECH
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