Functionalized ionic liquid capable of selectively separating amino acids, preparation method and application thereof

An ionic liquid and amino acid technology, applied in the field of organic synthesis and biological separation and purification, can solve the problems of limited improvement ability of separation and purification process, single type of ionic liquid, diversity of difficult-to-functionalize ionic liquids, etc. Highly economical effect

Inactive Publication Date: 2015-02-04
ZHEJIANG GONGSHANG UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, for most biological researchers, the application research of ionic liquids in the field of biomass separation and purification, especially the separation and purification of amino acids, is often based on traditional ionic liquids with relatively simple structures as extractants, in order to improve separation and purification effect (separation efficiency or selectivity), but there are many limitations in this process: 1) the high viscosity of traditional ionic liquids weakens the mass transfer efficiency; 2) the lack of "specific" functional groups in the molecular structure, for the separation The ability to improve the purification process is limited; 3) The type of ionic liquid is single, and there is a lack of targeted structural design and effective preparation methods, which is not conducive to the research on the extraction and separation of biomass
Although functional ionic liquids can be used to easily and quickly optimize the separation and purification process of biomass, this research direction is an interdisciplinary subject, and it is difficult for biologists who are familiar with the structure of biomass to effectively use modern organic synthesis techniques to realize various functional ionic liquids. Sexual structure needs to be envisaged, so development is slow

Method used

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  • Functionalized ionic liquid capable of selectively separating amino acids, preparation method and application thereof
  • Functionalized ionic liquid capable of selectively separating amino acids, preparation method and application thereof
  • Functionalized ionic liquid capable of selectively separating amino acids, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] 1) Synthesis of 5,6,7,8-tetrahydropyridine [1,2-α]-3-(acetyl-n-butylamine) imidazole trifluorosulfonic acid isophenylalanine salt, ([4C-imCH 2 CONHBu][Tf-Phe]):

[0062] First, the anion (N-Trifluoromethanesulfonylphenylalanine, [Tf-Phe]) part was synthesized: at 0°C, thionyl chloride (0.24mol, 28.55g) was slowly added dropwise into a solution of phenylalanine (0.2mol, 33.04g). In methanol (100mL), after the dropwise addition was completed, the temperature was raised to reflux for 5h. After the reaction, filter, collect the filtrate, and remove the solvent under reduced pressure to obtain a white solid (yield94%). The intermediate (0.1mol, 18.00g) was dissolved in 100mL of dichloromethane, and placed at -78°C under nitrogen protection, and trifluoromethanesulfonic anhydride (0.1mol, 16.90mL) (CAS : 358-23-6) was slowly added dropwise into the system, after the dropwise addition was completed, it was raised to room temperature and stirred overnight. After the reacti...

Embodiment 2

[0074] 1) Synthesis of 6,7-dihydro-5H-pyrrole[1,2α]-3-(acetyl-alkylamine) imidazole trifluorosulfonic acid valine salt ([3C-imCH 2 CONHBu][Tf-Val]):

[0075] First, the anion (N-Trifluoromethanesulfonylvaline, [Tf-Val]) part was synthesized: at 0°C, thionyl chloride (0.24mol, 28.55g) was slowly added dropwise into methanol dissolved in valine (0.2mol, 23.43g) (100mL), after the dropwise addition was completed, the temperature was raised to reflux for 5h. After the reaction, filter, collect the filtrate, and remove the solvent under reduced pressure to obtain a white solid intermediate product (yield95%). The intermediate (0.15mol, 19.68g) was dissolved in 100mL of dichloromethane, and placed at -78°C under nitrogen protection, trifluoromethanesulfonic anhydride (0.2mol, 33.80mL) (CAS : 358-23-6) was slowly added dropwise into the system, and after the dropwise addition was completed, return to room temperature and stirred overnight. After the reaction, wash with dilute hy...

Embodiment 3

[0079] 1) Synthesis of 6,7-dihydro-5H-pyrrole [1,2-α]-3-(acetyl-alkylamine) imidazole trifluorosulfonic acid leucine salt, ([3C-imCH 2 CONHBu][Tf-Leu]):

[0080] First, the anion (N-Trifluoromethanesulfonylleucine, [Tf-Leu]) part was synthesized: at 0°C, thionyl chloride (0.24mol, 28.55g) was slowly added dropwise into methanol dissolved with leucine (0.2mol, 26.23g) (100mL), after the dropwise addition was completed, the temperature was raised to reflux for 5h. After the reaction, filter, collect the filtrate, and remove the solvent under reduced pressure to obtain a white solid intermediate product (yield92%). The intermediate (0.15mol, 21.78g) was dissolved in 100mL of dichloromethane, and placed at -78°C under nitrogen protection, trifluoromethanesulfonic anhydride (0.2mol, 33.80mL) (CAS : 358-23-6) was slowly added dropwise into the system, and after the dropwise addition was completed, return to room temperature and stirred overnight. After the reaction, wash with d...

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Abstract

The invention discloses a functionalized ionic liquid for modifying lipase, the structure of the functionalized ionic liquid is shown as formula (I), wherein M is 1 ~ 2; R1 and R2 are independently selected from substituted or unsubstituted alkyl, and the substituent on the alkyl is aryl. The functionalized ionic liquid is bonded with water to construct an ion liquid / water liquid- liquid two phase system, and by use of the selective separation and purification process of amino acids, the separation and purification efficacy and selectivity of the amino acids can be improved. The invention also discloses a preparation method of the functionalized ionic liquid and a method using the ion liquid / water liquid- liquid two phase system for selective separation and purification process of the amino acids, and provides a simple and flexible separation engineering technology with high separation efficiency and good selectivity.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and biological separation and purification, and specifically relates to a functionalized ionic liquid with multiple heterocyclic skeleton structures modified by amino acids, and a liquid-liquid two-phase system constructed by using such functional ionic liquids. Separation and purification of amino acids. Background technique [0002] Amino acid is an important basic substance that constitutes biological proteins and is related to life activities. Its molecular structure has amphoteric organic functional groups. They are widely used in the fields of food and medicine. However, the cost incurred in their separation and purification process often accounts for more than 80% of the entire production expenditure. The traditional separation and purification of amino acids is achieved by using ion exchange resins, but this technology not only consumes a lot of reagent materials, but also has ...

Claims

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Application Information

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IPC IPC(8): C07C311/16C07C227/40
Inventor 石玉刚孟岳成陈杰
Owner ZHEJIANG GONGSHANG UNIVERSITY
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