CN108558765A - A kind of ether functional ionic liquids and preparation method thereof - Google Patents

A kind of ether functional ionic liquids and preparation method thereof Download PDF

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Publication number
CN108558765A
CN108558765A CN201810311591.2A CN201810311591A CN108558765A CN 108558765 A CN108558765 A CN 108558765A CN 201810311591 A CN201810311591 A CN 201810311591A CN 108558765 A CN108558765 A CN 108558765A
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China
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preparation
ether
ionic liquids
functional ionic
ether functional
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CN201810311591.2A
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Inventor
佟静
井立强
刘春辉
刘海春
龚燕燕
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Liaoning University
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Liaoning University
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Priority to CN201810311591.2A priority Critical patent/CN108558765A/en
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/60Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/18Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/22Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention discloses a kind of ether functional ionic liquids and preparation method thereof.The ether functional ionic liquids have the structural formula as shown in (I).The ether functional ionic liquid preparation of the present invention is simple, and purity is high, at low cost, can effectively absorb sour gas, expand the type of ionic liquid and increased ionic liquid adjustability and practicability.

Description

A kind of ether functional ionic liquids and preparation method thereof
Technical field
The present invention relates to field of ionic liquid, it is specifically related to a kind of ether functional ionic liquids and preparation method thereof.
Background technology
As the ionic liquid of novel green medium, because having special physical property and chemical property and good Design causes extensive concern and the research of numerous scholars.Ionic liquid refers to the organic salt being in a liquid state at room temperature, this Kind liquid salt is made of organic cation and organic anion or inorganic anion.This fuse salt being in a liquid state but it is different In other ionic compounds.Ionic liquid has that lower vapour pressure, difficult volatilization, low boiling point, polarity is strong, dissolubility is strong and wider Chemical potential.
Discharge with the development that human being's production is lived, global warming, greenhouse gases aggravates, Acid rain damages dynamics It increases, causes extensive concern.How sour gas is effectively handled simultaneously, becomes primary task.Usually processing is acid Gas has Physical Absorption partition method, chemical absorbing partition method, adsorption separation method, membrane separation process etc..Ionic liquid has pole Big adjustability and the property done, thus considerably increases the type and purposes of ionic liquid.And ionic liquid at this stage Research is not also perfect, is constantly being occurred for novel ionic liquid yet.Therefore how to expand ionic liquid type and Purposes is the project that this field is constantly studied.
Invention content
The object of the present invention is to provide a kind of easy to operate, at low cost, purity height, the strong functions containing ether of stability The ionic liquid of type.
The technical solution adopted by the present invention is:A kind of ether functional ionic liquids have the structural formula as shown in (I):
A kind of preparation method of ether functional ionic liquids, includes the following steps:
1) by N- methylimidazoles and 2- chloroethyl ether compounds, under the protection of nitrogen, 78-82 DEG C of reaction 45-50h, Gained reactant places and freezes 10-15h in refrigerator, and liquid separation removes supernatant liquid, appropriate organic solvent washing is added, then rotate steaming Hair removes organic solvent, obtains ether functionality chloride salt ions liquid;
2) ether functionality chloride salt ions liquid is added in anion exchange resin and reacts 2-4h, obtain hydrogen-oxygen type ether Base functional ionic liquids;
3) hydrogen-oxygen type ether functional ionic liquids and suitable amino acid are mixed, reacts 70-75h at room temperature, rotated Evaporation, it is dry, obtain ether functional ionic liquids.
Preferably, the molar ratio of N- methylimidazoles and 2- chloroethyl ether compounds is 1:1.1.
Preferably, the 2- chloroethyl ether compounds are 2- chloroethyl methyl ethers.
Preferably, the organic solvent is ethyl acetate and acetonitrile by volume 1:The mixed liquor of (1-2).
Preferably, the anion exchange resin is 717 type anion exchange resin.
Preferably, the molar ratio of hydrogen-oxygen type ether functional ionic liquids and amino acid is 1:1.05.
The beneficial effects of the invention are as follows:The amino acids ether functional ionic liquids that the present invention synthesizes, have expanded ion The type of liquid improves the purity of product.
Description of the drawings
Fig. 1 is the nucleus magnetic hydrogen spectrum of ether functional ionic liquids prepared by embodiment 1.
Specific embodiment
It is further illustrated the present invention below by specific example.The present invention is not limited to embodiments, described not departing from Range under, can have small variation.
A kind of 1 ether functional ionic liquids of embodiment
Preparation method is as follows:
1) 1mol N- methylimidazoles are added in three-necked flask, under conditions of ice salt bath, are slowly added to 1.1mol 2- Chloroethyl methyl ether is transferred to oil bath pan, is passed through nitrogen, is warming up to 80 DEG C, stirs 48h.Reactant place refrigerator in, 0 DEG C with Lower freezing 10-15h, liquid separation remove supernatant liquid, the solids ethyl acetate of 8ml and the mixed liquor (v of acetonitrile:V=1:1) it washes It washs three times, filtering rotates evaporative removal organic solvent, and products therefrom at 65 DEG C, steam by dry 8-10h, repeated washing, rotation Hair, drying steps are three times, finally 8-10 hours dry in vacuum drying chamber, obtain 1- (2- methoxy ethyls) -3- methylimidazoles Chloride salt ions liquid.
2) 717 type anion exchange resin are taken, by activating and regenerating, processing obtains hydrogen-oxygen type anion exchange resin, will Hydrogen-oxygen type anion exchange resin fills column, is washed to neutrality, is allowed to dry.By 1- (2- methoxy ethyls) -3- methylimidazole villaumites from Sub- liquid is added in hydrogen-oxygen type anion exchange resin, is reacted 2-4h, is obtained hydrogen-oxygen type 1- (2- methoxy ethyls) -3- methyl Imidazole ion liquid, and demarcate rapidly.
3) 1mol hydrogen-oxygen types 1- (2- methoxy ethyls) -3- methylimidazoles ionic liquids and 1.05mol threonines are mixed, 72h is reacted at room temperature, and rotary evaporation is dry, obtains 1- (2- methoxy ethyls) -3- methylimidazole threonine ionic liquids, ties Structure formula is as follows, yield 85.6%, purity 98%.The nucleus magnetic hydrogen spectrum of product such as Fig. 1.

Claims (7)

1. a kind of ether functional ionic liquids, which is characterized in that have the structural formula as shown in (I):
2. a kind of preparation method of ether functional ionic liquids described in claim 1, which is characterized in that including walking as follows Suddenly:
1) by N- methylimidazoles and 2- chloroethyl ether compounds, under the protection of nitrogen, 78-82 DEG C of reaction 45-50h, gained Reactant is placed and freezes 10-15h in refrigerator, and liquid separation removes supernatant liquid, appropriate organic solvent washing is added, then rotary evaporation removes Organic solvent is removed, ether functionality chloride salt ions liquid is obtained;
2) ether functionality chloride salt ions liquid is added in anion exchange resin and reacts 2-4h, obtain hydrogen-oxygen type ether work( It can property ionic liquid;
3) hydrogen-oxygen type ether functional ionic liquids and suitable amino acid are mixed, reacts 70-75h at room temperature, rotary evaporation, It is dry, obtain ether functional ionic liquids.
3. preparation method according to claim 2, which is characterized in that step 1), N- methylimidazoles and 2- chloroethyl ethers The molar ratio of compound is 1:1.1.
4. preparation method according to claim 2, which is characterized in that step 1), the 2- chloroethyl ether compounds For 2- chloroethyl methyl ethers.
5. preparation method according to claim 2, which is characterized in that step 1), the organic solvent are ethyl acetate With acetonitrile by volume 1:The mixed liquor of (1-2).
6. preparation method according to claim 2, which is characterized in that step 2), the anion exchange resin are 717 Type anion exchange resin.
7. preparation method according to claim 2, which is characterized in that step 3), hydrogen-oxygen type ether functional ionic liquids Molar ratio with amino acid is 1:1.05.
CN201810311591.2A 2018-04-09 2018-04-09 A kind of ether functional ionic liquids and preparation method thereof Pending CN108558765A (en)

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Application Number Priority Date Filing Date Title
CN201810311591.2A CN108558765A (en) 2018-04-09 2018-04-09 A kind of ether functional ionic liquids and preparation method thereof

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CN108558765A true CN108558765A (en) 2018-09-21

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110041265A (en) * 2019-05-10 2019-07-23 辽宁大学 A kind of functional form group containing ether ionic liquid and preparation method thereof
CN114671812A (en) * 2022-04-29 2022-06-28 辽宁大学 Functional ionic liquid containing ether group and preparation method thereof
CN114700018A (en) * 2022-04-08 2022-07-05 上海交通大学 Semi-automatic integrated reaction device and preparation method of imidazole amino acid ionic liquid

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101033213A (en) * 2007-03-30 2007-09-12 辽宁大学 Phenylalanine-1-methyl-3-butyl-imidazole amino acid ionic liquid and preparing method thereof
CN106220566A (en) * 2016-07-21 2016-12-14 辽宁大学 A kind of with amino acid whose ionic liquid and its preparation method and application

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101033213A (en) * 2007-03-30 2007-09-12 辽宁大学 Phenylalanine-1-methyl-3-butyl-imidazole amino acid ionic liquid and preparing method thereof
CN106220566A (en) * 2016-07-21 2016-12-14 辽宁大学 A kind of with amino acid whose ionic liquid and its preparation method and application

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SAKI FUJIWARA ET AL.: "Cation-π interactions within aromatic amino acid ionic liquids: A new tool for designing functional ionic liquids", 《JOURNAL OF MOLECULAR LIQUIDS》 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110041265A (en) * 2019-05-10 2019-07-23 辽宁大学 A kind of functional form group containing ether ionic liquid and preparation method thereof
CN114700018A (en) * 2022-04-08 2022-07-05 上海交通大学 Semi-automatic integrated reaction device and preparation method of imidazole amino acid ionic liquid
CN114671812A (en) * 2022-04-29 2022-06-28 辽宁大学 Functional ionic liquid containing ether group and preparation method thereof

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