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Method for preparing quaternary ammonium aluminum hydride

A technology of aluminum hydride and quaternary ammonium, applied in the field of preparation of quaternary ammonium aluminum hydride, can solve the problems of poor solubility, difficulty in purification, and inability to obtain products effectively, and achieves the effect of avoiding filtration of impurity salts and shortening reaction time

Inactive Publication Date: 2019-01-29
LIMING RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Regrettably, these reducing agents all have many shortcomings: (1) be afraid of tide and water, all need to carry out under the protection of inert gas in use or storage process, in order to avoid combustion, even explosion accident; (2) in Non-ether solvents, especially inert aromatic solvents, have very poor solubility, which limits their application; (3) although they are a class of efficient reducing agents, their steric selectivity is poor in stereochemistry and cannot Effectively obtain products with a certain spatial configuration
Thereby, existing method prepares quaternary ammonium aluminum hydride and has the shortcoming that reaction time is long, purification difficulty, yield are not high

Method used

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  • Method for preparing quaternary ammonium aluminum hydride
  • Method for preparing quaternary ammonium aluminum hydride
  • Method for preparing quaternary ammonium aluminum hydride

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Under nitrogen protection, weigh 1.56g LiAlH 4 (0.0411mol) in a 500mL three-necked flask, add 80mL of anhydrous ethylene glycol dimethyl ether, and install a reflux condenser and a constant pressure dropping funnel; then weigh 15g of tetra-n-octylammonium bromide (0.0274mol) in Add 80mL of anhydrous ethylene glycol dimethyl ether to a 250mL flask with a branch, heat and stir in an oil bath at 50°C to dissolve; then, transfer the tetra-n-octylammonium bromide solution to a constant pressure dropping funnel Add dropwise to the there-necked flask within 40min; after the dropwise addition, continue to heat and reflux for 4h; after the reaction, add 160mL of n-heptane and filter through a sand core funnel to obtain a transparent and clear filtrate; then carry out vacuum distillation on the filtrate, Most of the solvent was removed, and finally vacuum-dried in an oil bath at 55° C. for 2 h to obtain 12.94 g of a waxy solid with a yield of about 94.9%.

Embodiment 2

[0031] Under nitrogen protection, weigh 0.78g LiAlH 4 (0.0206mol) in a 250mL three-neck flask, add 50mL of anhydrous ethylene glycol dimethyl ether, and install a reflux condenser and a constant pressure dropping funnel; then weigh 5.54g of tri-n-octylmethyl ammonium chloride (0.0137 mol) into a 250mL flask with a branched mouth, then add 50mL of anhydrous ethylene glycol dimethyl ether, and heat and stir in an oil bath at 50°C to dissolve; subsequently, transfer the tri-n-octylmethylammonium chloride solution to In the constant pressure dropping funnel, add it dropwise into the three-neck flask within 40 minutes, and the solution begins to form a large amount of white precipitate; after the dropwise addition, continue to heat and reflux for 2 hours; Transparent and clear filtrate; the filtrate was distilled under reduced pressure to remove most of the solvent, and finally dried in vacuum in an oil bath at 55° C. for 2 hours to obtain 5.10 g of a waxy solid with a yield of abo...

Embodiment 3

[0033] Under nitrogen protection, weigh 1.11g NaAlH 4 (0.0206mol) in a 500mL three-necked flask, add 80mL tetrahydrofuran, and install a reflux condenser and a constant pressure dropping funnel; then weigh 10.85g hexadecyldimethylbenzyl ammonium chloride (0.0274mol) in 250mL Add 80 mL of anhydrous ethylene glycol dimethyl ether to a flask with a branched mouth, heat and stir in an oil bath at 50°C to dissolve; then, transfer the cetyl dimethyl benzyl ammonium chloride solution to a constant In the pressure dropping funnel, drop it into the three-necked bottle within 40 minutes, and the solution begins to form a large amount of white precipitate; after the dropwise addition, continue to heat and reflux for 4 hours; The clarified filtrate; the filtrate was distilled under reduced pressure to remove most of the solvent, and finally vacuum-dried in an oil bath at 55° C. for 2 hours to obtain 10.32 g of a waxy solid with a yield of about 96.1%.

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Abstract

The invention discloses a method for preparing a quaternary ammonium aluminum hydride. The method comprises the following steps: (1) adding an alkali metal aluminum hydride into a reactor with a reflux condensation tube and a constant-pressure dropping funnel under the protection of nitrogen, adding an organic solvent, then weighing a quaternary ammonium salt in a flask with a branch opening, adding an organic solvent, and carrying out heating and stirring for dissolving to obtain a quaternary ammonium salt solution; (2) transferring the quaternary ammonium salt solution to a constant-pressuredropping funnel under the protection of nitrogen, dropwise adding the quaternary ammonium salt solution into the reactor, and carrying out a heating reflux reaction for 2-6 hours; and (3) after the reaction is finished, adding a non-polar alkane with an equal volume into the solution, carrying out filtering, and removing the solvent from the filtrate to obtain a waxy solid, namely the quaternaryammonium aluminum hydride. The method is simple in process, short in reaction time, convenient in purification and high in yield.

Description

technical field [0001] The invention relates to a preparation method of quaternary ammonium aluminum hydride, belonging to the field of organic metal hydrides. Background technique [0002] In organic synthesis, metal aluminum hydrides such as lithium aluminum hydride and sodium aluminum hydride are commonly used high-efficiency reducing agents, especially for compounds such as esters, carboxylic acids, amides, and halogenated hydrocarbons. Regrettably, these reducing agents all have many shortcomings: (1) be afraid of tide and water, all need to carry out under the protection of inert gas in use or storage process, in order to avoid combustion, even explosion accident; (2) in Non-ether solvents, especially inert aromatic solvents, have very poor solubility, which limits their application; (3) although they are a class of efficient reducing agents, their steric selectivity is poor in stereochemistry and cannot Effectively obtain products with a certain spatial configuration...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/00C07C211/63
CPCC07C209/00C07C211/63
Inventor 李文江夏宇邢校辉常伟林于文杰王建伟薛金强尚丙坤
Owner LIMING RES INST OF CHEM IND
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