Amino-acid ester derivative cation type chiral ionic liquid and preparation method thereof

A chiral ionic liquid and amino acid ester technology are applied to the cationic chiral ionic liquid of amino acid ester derivatives and the preparation thereof, the cationic ionic liquid of amino acid derivatives and the field of preparation thereof, which can solve the problem of rough preparation methods and limited scope of use. , simple structure, etc.

Active Publication Date: 2015-12-16
TANGSHAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, reports on the synthesis of ionic liquids using amino acids as chiral sources have gradually increased. For example, Chinese patents CN1383920A, CN104693056A and CN1383921A respectively describe a kind of L-amino acid sulfate type chiral ionic liquid and its preparation method and L-amino acid sulfate Type chiral ionic liquid and the technical scheme of preparation method thereof, CN1621152A has described amino acid ester cationic ionic liquid and preparation method thereof, these disclosed technical schemes have enriched the kind of amino acid ionic liquid, have provided beneficial exploration for the application of ionic liquid, but above-mentioned The amino acid ionic liquid preparation method described in the patent application is rough, and the amino acid cation structure is simple (either carboxyl or amino), which limits its application range

Method used

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Effect test

Embodiment 1

[0026] Amino acid ester derivative cationic chiral ionic liquid, its structural formula is as follows:

[0027] , The amino acid is D-, L-alanine

[0028] In the amino acid derivative cation, R ’ For CH 3 Or CH 3 CH 2 . The X - BF 4 - , PF 6 - , HSO 4 - Any of them.

[0029] The general formula of the amino acid ester derivative cationic chiral ionic liquid is A + X - , Where A + Cationic derivative of amino acid ester, X - BF 4 - , PF 6 - , HSO 4 - .

Embodiment 2

[0031] Preparation method of amino acid ester derivative cationic chiral ionic liquid

[0032] (1) Slowly add thionyl chloride dropwise to methanol under a low temperature environment of -14℃~-10℃, continue to react for 1 hour after the dripping, warm up to room temperature, add amino acids in batches, keep at 50℃ and stir for 4 After hours, the solvent was removed by rotary evaporation to obtain the hydrochloride of the amino acid ester, which was a viscous liquid;

[0033] (2) Mannich reaction: add paraformaldehyde to methanol, adjust the pH to 5 with dilute hydrochloric acid, heat until the paraformaldehyde is dissolved, and then lower to room temperature to add the product amino acid ester hydrochloride and acetone of step (1) , Heating to reflux for 48 hours, rotary evaporation to remove the solvent, the crude product is purified by column chromatography (eluent is a mixture of methanol and dichloromethane in a volume ratio of 1:20) to obtain the amino acid ester derivative Ma...

Embodiment 3

[0044] Preparation of cationic chiral ionic liquids of methyl alanine methyl ester derivatives

[0045] (1) Synthesis of alanine methyl ester

[0046] Take 125mL of methanol and add it to a 250mL three-necked flask (make sure the environment is dry during the reaction, with a drying device; the reaction will generate HCl and SO 2 Gas, use lye absorption device), cool it to -14℃ in a low temperature constant temperature reaction bath, slowly add 10mL (0.138mol) SOCl dropwise under magnetic stirring 2 Control the reaction temperature below -10°C during the dropping, and continue the reaction for 1 hour after the dropping is completed. The reaction solution was transferred to a 250mL round bottom flask, the temperature was naturally raised to room temperature, 12.21g (0.137mol) of alanine was added, and the reaction was stopped after heating and refluxing for 4 hours under magnetic stirring. The product was rotary evaporated and the solvent was evaporated to obtain alanine methyl este...

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Abstract

The invention provides an amino-acid ester derivative cation type chiral ionic liquid and a preparation method thereof. A general formula of the amino-acid ester derivative cation type chiral ionic liquid is A<+>X<->, wherein A<+> represents an amino-acid ester cation derivative, and X<-> represents one of BF4<->, PF6<-> and HSO4<->. The preparation method comprises steps as follows: amino acid, methyl alcohol and thionyl chloride react at the low temperature, and amino acid ester hydrochloride is obtained; amino acid ester hydrochloride has a Mannich reaction with paraformaldehyde and acetone, and amino acid ester derivative Mannich base is obtained; amino acid ester derivative Mannich base reacts with bromo-hydrocarbon, and a bromate type chiral ionic liquid of the amino-acid ester derivative is obtained; bromide ions of the bromate type chiral ionic liquid of the amino-acid ester derivative are exchanged, and the amino-acid ester derivative cation type chiral ionic liquid is obtained. The amino-acid ester derivative cation type chiral ionic liquid has the multiple advantages of high selectivity of a chiral substance as well as non-volatility, non-toxicity and pollution prevention of an ionic liquid, and is suitable for large-scale production of the fine chemical industry.

Description

technical field [0001] The invention relates to an amino acid derivative cationic ionic liquid and a preparation method thereof, in particular to a cationic amino acid ester derivative cationic chiral ionic liquid and a preparation method thereof, belonging to the technical field of chemical materials and their preparation. Background technique [0002] Ionic liquids are salts composed of organic cations and organic or inorganic anions that are liquid at or near room temperature. Ionic liquids have excellent physical and chemical properties such as low vapor pressure, good electrical conductivity, strong polarity, wide electrochemical window, high thermal stability, and good solubility and catalytic properties for certain substances. As well as the anion-cation structure that can be modified / tuned, and can be recycled, it is considered to be a new type of green solvent that can replace commonly used volatile organic solvents, and has been widely used in the field of chemical...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/12C07C227/18
Inventor 蔡明建
Owner TANGSHAN NORMAL UNIV
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