CN103242235A - Chloridized 1-vinyl-3-amino-formyl methyl-imidazole bifunctional ionic liquid and synthetic method thereof - Google Patents
Chloridized 1-vinyl-3-amino-formyl methyl-imidazole bifunctional ionic liquid and synthetic method thereof Download PDFInfo
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Abstract
The invention provides chloridized 1-vinyl-3-amino-formyl methyl-imidazole bifunctional ionic liquid and a synthetic method thereof. The chloridized 1-vinyl-3-amino-formyl methyl-imidazole bifunctional ionic liquid is obtained by taking 1-vinylimidazole and 2-chloroacetamide as raw materials, acetone as a solvent and phenol as a polymerization inhibitor, and reacting at 45-55 DEG C. The synthesized ionic liquid enriches the variety of polymerizable ionic liquid, and provides more selections for the application of the ionic liquid in the fields of functional materials, catalysis, separation and the like. Besides, the synthetic method is simple in step, does not need special equipment and is lower in cost.
Description
Technical field
The present invention relates to a kind of bifunctional ionic liquid chlorination 1-vinyl-3-carbamoyl methyl imidazoles and synthetic method thereof with two keys and amide group, belong to functional materials and preparing technical field thereof.
Background technology
Ionic liquid is formed the melting salt that is in a liquid state by organic cation and inorganic anion or inorganic cation and organic anion under 100 ℃.Ionic liquid does not almost have vapour pressure, and is not flammable, has higher ion density and ionic conductivity, and inorganics and organism are had dissolving power preferably.Because the adjustability of yin, yang ion can obtain the ionic liquid of required character by changing the structure of yin, yang ion in the ionic liquid.Therefore, ionic liquid had widespread usage in the last few years in separation chemistry, electrochemistry, organic chemistry even polymer chemistry.
An important branch as ionic liquid, the polymerizable ionic liquid had both had the constitutional features of ionic liquid, can be prepared into polymkeric substance again, the polymkeric substance of preparation can obtain special function because of ionic liquid special construction and character, therefore has been subjected to investigator's extensive concern.Wherein based on the ionic liquid of 1-vinyl imidazole because its raw material sources are wide, price is comparatively cheap, synthetic method is simple, ionic liquid is stable, become the focus of ionic liquid investigator concern in the last few years.People [Lu Guo such as Guo Lu, Qiliang Deng, Guozhen Fang, et al.Journal of Chromatography A., 2011,1218:6271-6277] be function monomer with chlorination 1-vinyl-3-butyl imidazole, prepared the grand molecularly imprinted polymer of chlorine sulphur, these imprinted polymers can have recognition effect preferably to microsphere by electrostatic interaction.Yet along with the development of polymerizable ionic liquid, single double bond containing ionic liquid can not satisfy demands of applications, and more and more researchers begins multiple functional group is synthesized in a kind of ionic liquid, forms the polyfunctionality ionic liquid.People such as Deng Jun [Deng Jun, Du Qiuliang, Fu Xiangkai etc., Chinese science: chemistry., 2012,42 (6): 766-775] synthesize the chlorination 1-vinyl-3-alkyl acetate imidazole ion liquid with two keys and ester group in 2011, and utilized it to prepare polymer dielectric.People such as child's voice [child's voice, Fan Jieping, Xiao Zhuyun etc., chemical industry journal., 2011,62 (S2): 155-159] prepared bromination 1-vinyl-3-carboxyalkyl imidazole ion liquid, this ionic liquid because have polymerizability and
Acidity has potential using value in fields such as catalysis, gas adsorption.
Summary of the invention
The technical problem that solves
For fear of the deficiencies in the prior art part, the present invention proposes a kind of chlorination 1-vinyl-3-carbamoyl methyl imidazoles bifunctional ionic liquid and synthetic method, it is comparatively single to solve present ionic liquid kind, but the kind with the research extension ion liquid of polymerizable ionic liquid, widen the ionic liquid research field, have important researching value and wide application prospect.
Technical scheme
A kind of chlorination 1-vinyl-3-carbamoyl methyl imidazoles bifunctional ionic liquid is characterized in that constitutional features is:
A kind of synthetic method for preparing described chlorination 1-vinyl-3-carbamoyl methyl imidazoles bifunctional ionic liquid is characterized in that step is as follows:
Step 1: the 2-chlor(o)acetamide is dissolved in the acetone, and fully stirs 20min down at 50 ℃, obtain containing the clarification acetone soln of 2-chlor(o)acetamide; Described 2-chlor(o)acetamide molten with mass ratio acetone be 1: 15～25;
Step 2: add stopper phenol in the solution of step 1, obtain mixing solutions; Add-on is 1% of 1-vinyl imidazole quality;
Step 3: the 1-vinyl imidazole is joined in the mixing solutions of step 2 gained, under 45～55 ℃, reaction 18～24h filters, and obtains white precipitate; Described 1-vinyl imidazole and 2-chlor(o)acetamide mol ratio are 1: 1～1: 2.5;
Step 4: with white precipitate washing with acetone 3 times, at 50 ℃ of following vacuum-drying 3h, obtain white powder chlorination 1-vinyl-3-carbamoyl methyl imidazoles bifunctional ionic liquid.
Beneficial effect
A kind of chlorination 1-vinyl-3-carbamoyl methyl imidazoles bifunctional ionic liquid and synthetic method that the present invention proposes, be raw material with 1-vinyl imidazole and 2-chlor(o)acetamide, acetone is solvent, phenol is stopper, reacts down at 45～55 ℃ to obtain chlorination 1-vinyl-3-carbamoyl methyl imidazole ion liquid.The ionic liquid that is synthesized has enriched the kind of polymerizable ionic liquid, for ionic liquid provides more choices in Application for Field such as functional materials, catalysis and separation.And step is simple, does not need specific installation, and cost is lower.
Embodiment
Now in conjunction with the embodiments the present invention is further described:
Embodiment 1:
With 3.00g(32.10mmol) the 2-chlor(o)acetamide join in the middle of the acetone of 45.00g, stir down fully 20min at 50 ℃, obtain containing the clarification acetone soln of 2-chlor(o)acetamide.The stopper phenol that adds 0.03g in the solution, after the stirring, add 3.02g(32.10mmol) the 1-vinyl imidazole, 45 ℃ of reaction 24h down, reaction obtains white precipitate, with white precipitate washing with acetone 3 times, each acetone consumption 30mL filters, in vacuum drying oven, 50 ℃ of following vacuum drying 3h obtain chlorination 1-vinyl-3-carbamoyl methyl imidazoles white powder 1.93g, productive rate 32%.
Embodiment 2:
With 4.50g(48.15mmol) the 2-chlor(o)acetamide join in the middle of the acetone of 90.00g, stir down fully 20min at 50 ℃, obtain containing the clarification acetone soln of 2-chlor(o)acetamide.The stopper phenol that adds 0.03g in the solution, after the stirring, add 3.02g(32.1mmol) the 1-vinyl imidazole, 48 ℃ of reaction 24h down, reaction obtains white precipitate, with white precipitate washing with acetone 3 times, each acetone consumption 30mL filters, in vacuum drying oven, 50 ℃ of following vacuum drying 3h obtain chlorination 1-vinyl-3-carbamoyl methyl imidazoles white powder 2.23g, productive rate 37%.
Embodiment 3:
With 6.00g(64.20mmol) the 2-chlor(o)acetamide join in the middle of the acetone of 150.00g, stir down fully 20min at 50 ℃, obtain containing the clarification acetone soln of 2-chlor(o)acetamide.The stopper phenol that adds 0.03g in the solution, after the stirring, add 3.02g(32.1mmol) the 1-vinyl imidazole, 50 ℃ of reaction 18h down, reaction obtains white precipitate, with white precipitate washing with acetone 3 times, each acetone consumption 30mL filters, in vacuum drying oven, 50 ℃ of following vacuum drying 3h obtain chlorination 1-vinyl-3-carbamoyl methyl imidazoles white powder 2.05g, productive rate 34%.
Embodiment 4:
With 7.50g(32.1mmol) the 2-chlor(o)acetamide join in the middle of the acetone of 150.00g, stir down fully 20min at 50 ℃, obtain containing the clarification acetone soln of 2-chlor(o)acetamide.The stopper phenol that adds 0.03g in the solution, after the stirring, add 3.02g(32.1mmol) the 1-vinyl imidazole, 52 ℃ of reaction 20h down, reaction obtains white precipitate, with white precipitate washing with acetone 3 times, each acetone consumption 30mL filters, in vacuum drying oven, 50 ℃ of following vacuum drying 3h obtain chlorination 1-vinyl-3-carbamoyl methyl imidazoles white powder 2.53g, productive rate 42%.
Embodiment 5:
With 3.00g(32.1mmol) the 2-chlor(o)acetamide join in the middle of the acetone of 60.00g, stir down fully 20min at 50 ℃, obtain containing the clarification acetone soln of 2-chlor(o)acetamide.The stopper phenol that adds 0.03g in the solution, after the stirring, add 3.02g(32.1mmol) the 1-vinyl imidazole, 55 ℃ of reaction 18h down, reaction obtains white precipitate, with white precipitate washing with acetone 3 times, each acetone consumption 30mL filters, in vacuum drying oven, 50 ℃ of following vacuum drying 3h obtain chlorination 1-vinyl-3-carbamoyl methyl imidazoles white powder 2.83g, productive rate 47%.
Claims (2)
1. chlorination 1-vinyl-3-carbamoyl methyl imidazoles bifunctional ionic liquid is characterized in that constitutional features is:
2. synthetic method for preparing the described chlorination 1-vinyl of claim 1-3-carbamoyl methyl imidazoles bifunctional ionic liquid is characterized in that step is as follows:
Step 1: the 2-chlor(o)acetamide is dissolved in the acetone, and fully stirs 20min down at 50 ℃, obtain containing the clarification acetone soln of 2-chlor(o)acetamide; Described 2-chlor(o)acetamide molten with mass ratio acetone be 1: 15～25;
Step 2: add stopper phenol in the solution of step 1, obtain mixing solutions; Add-on is 1% of 1-vinyl imidazole quality;
Step 3: the 1-vinyl imidazole is joined in the mixing solutions of step 2 gained, under 45～55 ℃, reaction 18～24h filters, and obtains white precipitate; Described 1-vinyl imidazole and 2-chlor(o)acetamide mol ratio are 1: 1～1: 2.5;
Step 4: with white precipitate washing with acetone 3 times, at 50 ℃ of following vacuum-drying 3h, obtain white powder chlorination 1-vinyl-3-carbamoyl methyl imidazoles bifunctional ionic liquid.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104529901A (en) * | 2014-12-31 | 2015-04-22 | 西北工业大学 | Imidazole unsaturated ionic liquid and preparation method thereof |
| CN105838068A (en) * | 2016-05-18 | 2016-08-10 | 苏州大学 | Polyion liquid-modified carbon nano-tube hybrid material and preparation method thereof |
| CN106046782A (en) * | 2016-05-18 | 2016-10-26 | 苏州大学 | Modified cyanate resin and preparation method thereof |
| CN106328995A (en) * | 2015-07-07 | 2017-01-11 | 中国科学院过程工程研究所 | Electrolyte additive for lithium ion battery |
| CN109053576A (en) * | 2018-07-26 | 2018-12-21 | 中国科学院过程工程研究所 | A kind of ionic liquid curing agent and preparation method thereof suitable for epoxy resin |
| CN109627216A (en) * | 2018-12-26 | 2019-04-16 | 陕西科技大学 | A kind of chlorination 1- aminoacyl methyl -3- vinyl iminazole ionic liquid and preparation method thereof |
| CN112979554A (en) * | 2021-02-03 | 2021-06-18 | 西京学院 | Ionic liquid containing carbon-carbon double bond and phenolic hydroxyl functional group simultaneously and synthesis method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5922653A (en) * | 1995-12-20 | 1999-07-13 | Phillips Petroleum Company | Compositions and processes for treating subterranean formations |
| CN101341872A (en) * | 2008-08-22 | 2009-01-14 | 集美大学 | Ion liquid anti-virus activities bactericide, synthesis and application thereof |
| CN101591296A (en) * | 2009-06-19 | 2009-12-02 | 中国科学院上海有机化学研究所 | A kind of high-density ionic liquid and preparation method thereof |
| WO2013066941A1 (en) * | 2011-10-31 | 2013-05-10 | The Board Of Trustees Of The University Of Arkansas | Catalytic membranes and applications thereof |
-
2013
- 2013-05-16 CN CN201310182015XA patent/CN103242235A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5922653A (en) * | 1995-12-20 | 1999-07-13 | Phillips Petroleum Company | Compositions and processes for treating subterranean formations |
| CN101341872A (en) * | 2008-08-22 | 2009-01-14 | 集美大学 | Ion liquid anti-virus activities bactericide, synthesis and application thereof |
| CN101591296A (en) * | 2009-06-19 | 2009-12-02 | 中国科学院上海有机化学研究所 | A kind of high-density ionic liquid and preparation method thereof |
| WO2013066941A1 (en) * | 2011-10-31 | 2013-05-10 | The Board Of Trustees Of The University Of Arkansas | Catalytic membranes and applications thereof |
Non-Patent Citations (3)
| Title |
|---|
| QIULIANG DU，等: "Polymer Electrolytes Based on Polymeric Ionic Liquid Poly(methyl 2-(3-vinylimidazolidin-1-yl)acetate bis(trifluoromethane sulfonyl)imide)", 《JOURNAL OF INORGANIC AND ORGANOMETALLIC POLYMERS AND MATERIALS》 * |
| YANPENG YU，等: "Pd nanoparticles on a porous ionic copolymer: a highly active and recyclable catalyst for Suzuki–Miyaura reaction under air in water", 《CHEMICAL COMMUNICATIONS》 * |
| YUBING XIONG,等: "Novel One-Step Synthesis to Cross-Linked Polymeric Nanoparticles as Highly Active and Selective Catalysts for Cycloaddition of CO2 to Epoxides", 《JOURNAL OF APPLIED POLYMER SCIENCE》 * |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104529901A (en) * | 2014-12-31 | 2015-04-22 | 西北工业大学 | Imidazole unsaturated ionic liquid and preparation method thereof |
| CN106328995A (en) * | 2015-07-07 | 2017-01-11 | 中国科学院过程工程研究所 | Electrolyte additive for lithium ion battery |
| CN105838068A (en) * | 2016-05-18 | 2016-08-10 | 苏州大学 | Polyion liquid-modified carbon nano-tube hybrid material and preparation method thereof |
| CN106046782A (en) * | 2016-05-18 | 2016-10-26 | 苏州大学 | Modified cyanate resin and preparation method thereof |
| CN105838068B (en) * | 2016-05-18 | 2018-06-29 | 苏州大学 | A kind of carbon nano-tube modified hybrid material of poly ion liquid and preparation method thereof |
| CN106046782B (en) * | 2016-05-18 | 2018-07-20 | 苏州大学 | A kind of modified cyanic acid ester resin and preparation method thereof |
| CN109053576A (en) * | 2018-07-26 | 2018-12-21 | 中国科学院过程工程研究所 | A kind of ionic liquid curing agent and preparation method thereof suitable for epoxy resin |
| CN109053576B (en) * | 2018-07-26 | 2020-06-19 | 中国科学院过程工程研究所 | Ionic liquid curing agent suitable for epoxy resin and preparation method thereof |
| CN109627216A (en) * | 2018-12-26 | 2019-04-16 | 陕西科技大学 | A kind of chlorination 1- aminoacyl methyl -3- vinyl iminazole ionic liquid and preparation method thereof |
| CN112979554A (en) * | 2021-02-03 | 2021-06-18 | 西京学院 | Ionic liquid containing carbon-carbon double bond and phenolic hydroxyl functional group simultaneously and synthesis method thereof |
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Application publication date: 20130814 |