Amino acid ester derivative cationic chiral ionic liquid and preparation method thereof

A technology of chiral ionic liquid and amino acid ester, which is applied in the fields of amino acid derivative cationic ionic liquid and its preparation, amino acid ester derivative cationic chiral ionic liquid and its preparation field, which can solve the problem of limited scope of use and rough preparation method , simple structure and other issues, to achieve the effect of low price, new varieties and low steam pressure

Active Publication Date: 2017-03-29
TANGSHAN NORMAL UNIV
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  • Summary
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  • 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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Experimental program
Comparison scheme
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] Among the amino acid derivative cations, R ’ for CH 3 or CH 3 CH 2 . The X - for BF 4 - 、PF 6 - 、HSO 4 - any of the.

[0029] The general formula of the amino acid ester derivative cationic chiral ionic liquid is A + x - , where A + For amino acid ester cationic derivatives, X - for 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 at a low temperature environment of -14°C to -10°C, continue to react for 1 hour after the drop is complete, raise the temperature to room temperature, add amino acids in batches, keep stirring at 50°C for 4 After hours, the solvent was removed by rotary evaporation to obtain the hydrochloride of 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 dissolves, then cool down to room temperature and add the product of step (1) amino acid ester hydrochloride and acetone , heated to reflux for 48 hours, and the solvent was removed by rotary evaporation, and the crude product was purified by column chromatography (a mixture of methanol and dichloromethane with a volume ratio of 1:20 was used as the e...

Embodiment 3

[0044] Preparation of Cationic Chiral Ionic Liquids of 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 (the environment should be anhydrous during the reaction, with a drying device; the reaction will generate HCl and SO 2 Gas, use alkali liquid absorption device), cool it to -14°C 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 dropwise addition, and continue the reaction for 1h after the dropwise addition is completed. The reaction solution was transferred to a 250mL round-bottomed flask, the temperature was naturally raised to room temperature, 12.21g (0.137mol) of alanine was added, and the reaction was stopped after heating to reflux under magnetic stirring for 4 hours. The product was rotary evaporated, and after the solvent was evapo...

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Abstract

A novel amino acid ester derivative cationic chiral ionic liquid and a preparation method thereof. The general formula of the amino acid ester derivative cationic chiral ionic liquid is A+X-, wherein A+ is an amino acid ester cationic derivative, and X-is BF4-, PF6-, HSO4-. The preparation method is: react amino acid with methanol and thionyl chloride at low temperature to obtain amino acid ester hydrochloride; react amino acid ester hydrochloride with paraformaldehyde and acetone through Mannich reaction to obtain amino acid ester derivative Mannich base Amino acid ester derivative Mannich base reacts with brominated hydrocarbon to obtain bromide salt chiral ionic liquid of amino acid ester derivative; amino acid ester derivative is obtained by exchanging the bromide ion of the bromide salt chiral ionic liquid of amino acid ester derivative Cationic chiral ionic liquid. The invention has many advantages such as high selectivity of chiral substances, non-volatile, non-toxic, non-polluting ionic liquid, and is suitable for large-scale production in 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 Patents(China)
IPC IPC(8): C07C229/12C07C227/18
Inventor 蔡明建
Owner TANGSHAN NORMAL UNIV
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