[ethyl (R)-(+)-beta-(1- methylimidazolyl)-propionate]X chiral ionic liquid and synthesis method thereof

A technology of chiral ionic liquid and methylimidazole, applied in the preparation of carboxylate, organic chemistry, etc., can solve the problems of high melting point and low yield of imidazole-type chiral ionic liquid

Inactive Publication Date: 2011-08-03
NORTHWESTERN POLYTECHNICAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In order to overcome the deficiencies of high melting point and low yield of imidazole-type chiral ionic liquids prepared by existing preparation methods, the invention provides a [(R)-(+)-β-(1-methylimidazole)-propionic acid Ethyl ester]X chiral ionic liquid

Method used

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  • [ethyl (R)-(+)-beta-(1- methylimidazolyl)-propionate]X chiral ionic liquid and synthesis method thereof
  • [ethyl (R)-(+)-beta-(1- methylimidazolyl)-propionate]X chiral ionic liquid and synthesis method thereof

Examples

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Embodiment 1

[0022]Example 1: Synthesis of (R)-(+)-β-(1-methylimidazole)-propionic acid ethyl ester chiral ionic liquid: (S)-(-)-2-chloropropionic acid 43.6 g and 117ml of absolute ethanol were mixed, 2ml of concentrated sulfuric acid was added as a catalyst, and the reaction was stirred and refluxed at 55°C for 48h at a stirring rate of 400r / min. After the reaction was completed, 150 ml of distilled water was added to separate the layers, and the lower layer liquid was taken out by liquid separation, and then distilled under reduced pressure at -0.1 MPa to obtain a colorless transparent liquid. The product was analyzed by high performance liquid chromatography, and the product was ethyl (S)-(-)-2-chloropropionate with a purity of 98.1%. Add 20.5g of N-methylimidazole into a 250ml three-necked flask, weigh 34.1g of the self-synthesized (S)-(-)-2-chloropropionic acid ethyl ester and add it to the dropping funnel, in a water bath at 60°C, Ethyl (S)-(-)-2-chloropropionate was added dropwise ...

Embodiment 2

[0024] Example 2: Synthesis of (R)-(+)-β-(1-methylimidazole)-propionic acid ethyl ester chiral ionic liquid: (S)-(-)-2-chloropropionic acid 43.6 g and 105ml of absolute ethanol were mixed, 2ml of concentrated sulfuric acid was added as a catalyst, and the reaction was stirred and refluxed at 60°C for 40h at a stirring rate of 400r / min. After the reaction was completed, 150 ml of distilled water was added to separate the layers, and the lower layer liquid was taken out by liquid separation, and then distilled under reduced pressure at -0.1 MPa to obtain a colorless transparent liquid. The product was analyzed by high performance liquid chromatography, and the product was ethyl (S)-(-)-2-chloropropionate with a purity of 97.8%. Add 20.5g of N-methylimidazole into a 250ml three-necked flask, weigh 47.8g of the self-synthesized (S)-(-)-2-chloropropionic acid ethyl ester and add it to the dropping funnel. In a water bath at 70°C, place Ethyl (S)-(-)-2-chloropropionate was added dr...

Embodiment 3

[0026] Example 3: Synthesis of (R)-(+)-β-(1-methylimidazole)-propionic acid ethyl ester chiral ionic liquid: (S)-(-)-2-chloropropionic acid 43.6 g and 105ml of absolute ethanol were mixed, 2ml of concentrated sulfuric acid was added as a catalyst, and the reaction was stirred and refluxed at 60°C for 40h at a stirring rate of 400r / min. After the reaction was completed, 150 ml of distilled water was added to separate the layers, and the lower layer liquid was taken out by liquid separation, and then distilled under reduced pressure at -0.1 MPa to obtain a colorless transparent liquid. The product was analyzed by high performance liquid chromatography, and the product was ethyl (S)-(-)-2-chloropropionate with a purity of 97.8%. Add 20.5g of N-methylimidazole into a 250ml three-necked flask, weigh 41.0g of the self-synthesized (S)-(-)-2-chloropropionic acid ethyl ester and add it to the dropping funnel, in a water bath at 65°C, Ethyl (S)-(-)-2-chloropropionate was added dropwise...

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Abstract

The invention discloses a [ethyl (R)-(+)-beta-(1-methylimidazole)-propionate]X chiral ionic liquid and a synthesis method which is used for solving the technical problem that imidazole type chiral ionic liquid prepared by the existing preparation method has high liquid melting point and low yield. The technical scheme is as follows: (S)-(-)-2-chloropropionic acid and (S)-(-)-2-bromopropionic acid are taken as raw materials and undergo esterification reaction with absolute ethyl alcohol to generate stable (S)-(-)-2-chloropropionic acid ethyl ester or (S)-(-)-2-bromopropionic acid ethyl ester; the (S)-(-)-2-chloropropionic acid ethyl ester or (S)-(-)-2-bromopropionic acid ethyl ester undergoes alkylation reaction with N- methylimidazole to generate chlorinated ethyl (R)-(+)-beta-(1-methylimidazole)-propionate or brominated ethyl (R)-(+)-beta-(1- methylimidazole)-propionate chiral ionic liquid; the chlorinated ethyl (R)-(+)-beta-(1- methylimidazole)- ropionate or brominated ethyl (R)-(+)-beta-(1- methylimidazole)-propionat chiral ionic liquid is used as an intermediate to undergo the anion exchange reaction with salts containing anions such as BF4<->, PF6<->, SCN<->, CH3COO<-> so as to obtain the [ethyl (R)-(+)-beta-(1- methylimidazole)-propionate] X chiral ionic liquid. The melting point of the [ethyl (R)-(+)-beta-(1- methylimidazole)-propionate] X chiral ionic liquid is reduced to minus 40 to minus 36 DEG C from 5 to 16 DEG C of the melting point of the background art; the yield of the [ethyl (R)-(+)-beta-(1- methylimidazole)-propionate] X chiral ionic liquid is increased to 52.8 to 60.5% from 20 to 35% of yield of the background art.

Description

technical field [0001] The invention relates to a chiral ionic liquid, in particular to a [(R)-(+)-β-(1-methylimidazole)-ethyl propionate]X chiral ionic liquid. It also relates to the synthesis method of this [(R)-(+)-β-(1-methylimidazole)-ethyl propionate]X chiral ionic liquid. Background technique [0002] Chiral ionic liquids have the dual functions of chiral materials and liquid materials. In addition to the functional characteristics of chiral materials, they also have excellent properties that general liquid materials do not have, such as: (1) It has a very wide range of liquid states, from below Room temperature to above 300°C, and has good physical and chemical stability; (2) low volatility and almost invisible vapor pressure at room temperature; (3) non-flammable; (4) for many inorganic Or organic matter has good solubility; (5) It is a kind of polar, non-coordinating solvent; (6) Its physical and chemical properties can be adjusted by selecting anion and cation. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/60C07C331/02C07C53/10C07C51/41
Inventor 胡小玲管萍赵亚梅李大鹏
Owner NORTHWESTERN POLYTECHNICAL UNIV
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