CN105061496A - Novel ionic liquid preparation method - Google Patents
Novel ionic liquid preparation method Download PDFInfo
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- CN105061496A CN105061496A CN201510511334.XA CN201510511334A CN105061496A CN 105061496 A CN105061496 A CN 105061496A CN 201510511334 A CN201510511334 A CN 201510511334A CN 105061496 A CN105061496 A CN 105061496A
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Abstract
The invention discloses a novel ionic liquid preparation method. The novel ionic liquid preparation method comprises the following steps: weighing unsaturated pendant imidazole and alkyl phosphate according to the substance ratio of 1:(1-1.2); dripping unsaturated pendant imidazole into stirred alkyl phosphate in an ice-water bath drop by drop; after dripping, heating the mixture to be 50-90 DEG C; stirring for reaction for 9-48 h under the reflow condition; using ethyl acetate to extract a mixed product for 3-8 times; steaming to remove a solvent at 50-80 DEG C; finally, performing vacuum drying on the obtained product in the presence of phosphorus pentoxide. The novel ionic liquid preparation method is a novel method for preparing ionic liquid, and when the structures of reactants are different, the obtained novel ionic liquid structures are also different. As the ionic liquid prepared by the method is excellent in performance and designable in structure, an applicable structure can be designed as required, and accordingly, a favorable foundation is laid for expanding application of the novel ionic liquid preparation method to the fields of organic synthesis, extraction separation, electrochemistry, nanometer material preparation, clean fuel production, environmental science, catalytic science and the like.
Description
Technical field
The present invention relates to ionic liquid preparation field, particularly a kind of preparation method of novel ion liquid.
Background technology
Ionic liquid, as the green solvent of novel reusable edible, presents liquid state at normal temperature or higher than under normal temperature, and its concrete structure is organic cation and organic or inorganic anion composition.Ionic liquid has following characteristics: wider liquid stabilising scope, stronger dissolving power, and lower vapour pressure, has certain viscosity, stronger catalytic activity.Due to the performance that it is superior, ionic liquid is widely used in organic synthesis, extracting and separating, electrochemistry, and prepared by nano material, Clean Fuel Production, environmental science, the every field such as catalytic science.Ionic liquid has obviously advantage as solvent: non-volatile, stable in properties, is easy to reclaim, and strong polarity, has good solubility to many inorganic salt, organism and macromolecular material, and can obtain higher concentration.These features show that ionic liquid completely may as the substitute of organic solvent.(Zhang Xingchen. ionic liquid---from theoretical basis to progress. Beijing: Chemical Industry Press, 2008,6:1-12)
Ionic liquid due to its phase transition temperature range wider, most of ionic liquid shows good thermostability, and thermolysis starting temperature is generally between 200 ~ 400 DEG C.The density of ionic liquid, between viscosity and specific conductivity, there is close relationship, with size, the shape of ion and interact relevant, simultaneously these all form with ionic liquid in the structure of zwitterion closely bound up, therefore ionic liquid has designability, can by the structure of regulating YIN and YANG ion, and synthesize various ionic liquid by suitable method, then detect its properties, therefrom select the ionic liquid meeting application conditions of good performance.
Summary of the invention
The invention provides a kind of preparation method of novel ion liquid, by " one kettle way " after being mixed by the amount of substances such as unsaturated side base imidazoles and alkyl phosphate, at suitable temperature and reaction times condition, synthesize novel ion liquid.
The present invention in order to the technical scheme solving its technical problem and adopt is: a kind of preparation method of novel ion liquid, its processing step and condition as follows:
Take unsaturated side base imidazoles and alkyl phosphate, make its amount of substance than being 1:1 ~ 1.2, in the alkyl phosphate that unsaturated side base imidazoles is dropwise added in ice-water bath, stirred, after dripping, by mixture heat to 50-90 DEG C, stirred at reflux condition reaction 9-48h, then be extracted with ethyl acetate mix products 3-8 time, desolventize 50-80 DEG C of steaming again, finally again by products therefrom 40-80 DEG C of vacuum-drying under Vanadium Pentoxide in FLAKES exists;
Unsaturated side base imidazoles and alkyl phosphate reaction expression as follows:
In above-mentioned chemical reaction general formula, described radicals R can be H
2c=CH---H
2c=CH-CH
2---, HC ≡ C---CH
2---, H
2c=CH---CH
2---CH2---described R
1, R
3be selected from C
1-C
18alkyl, R
2be selected from H and C
1-C
18alkyl.
As a further improvement on the present invention, the amount of described reactant species is than being 1:1 ~ 1.2, and temperature of reaction is 50 to 90 DEG C, and the reaction times is 9 to 48h, and the temperature of reaction is not very high, and condition is comparatively gentle; Reaction times, the product obtained find reaction 9h, 14h, 24h, 48h after removal of impurities process after did not have too big difference in its yield aspects, can more than 90% at 9h to 48h.
As a further improvement on the present invention, first mixed reactant is dropwise uniformly mixed under frozen water condition before reaction, contributes in next step back flow reaction.。
As a further improvement on the present invention, use " one kettle way " reaction, with unsaturated side base imidazoles and alkyl phosphate for raw material, do not add the third solvent any, for later stage removal of impurities process simplifies step.
As a further improvement on the present invention, with common low poison solvent extraction into ethyl acetate after reaction, ethyl acetate is adopted to make extraction agent, because two kinds of reactants can be miscible with it, and the ionic liquid generated is got along well, and it mixes, can effectively remove the reactant that may not react completely, the boiling point of ethyl acetate is relatively low simultaneously, can be easy to removing of reducing pressure at a lower temperature.
The invention has the beneficial effects as follows: compared with prior art, tool has the following advantages in the present invention:
Owing to the present invention is to provide a kind of novel method preparing ionic liquid, when reaction materil structure is different, the novel ion liquid structure obtained is also different.What prepare due to the present invention is the ionic liquid of excellent performance, its structure has designability, thus suitable structure can be designed as required, for expanding it in organic synthesis, extracting and separating, electrochemistry, prepared by nano material, Clean Fuel Production, environmental science, the application of the every field such as catalytic science is had laid a good foundation.
Embodiment
In order to deepen the understanding of the present invention, below in conjunction with embodiment, the invention will be further described, and this embodiment only for explaining the present invention, does not form limiting the scope of the present invention.
Embodiment 1:
Take N-vinyl imidazole and trimethyl phosphite 99, make its amount of substance than being 1:1 ~ 1.2,, in the alkyl phosphate that N-vinyl imidazole is dropwise added in ice-water bath, stirred, after dripping, by mixture heat to 50-90 DEG C, stirred at reflux condition reaction 9-48h, then be extracted with ethyl acetate mix products 3-8 time, then desolventize 50-80 DEG C of steaming, last again by products therefrom 40-80 DEG C of vacuum-drying under Vanadium Pentoxide in FLAKES exists, obtain 1-vinyl-3-methyl-imidazoles dimethyl phosphate salt.
Embodiment 2:
Take N-allyl imidazole and trimethyl phosphite 99, make its amount of substance than being 1:1 ~ 1.2,, in the alkyl phosphate that N-allyl imidazole is dropwise added in ice-water bath, stirred, after dripping, by mixture heat to 50-90 DEG C, stirred at reflux condition reaction 9-48h, then be extracted with ethyl acetate mix products 3-8 time, then desolventize 50-80 DEG C of steaming, last again by products therefrom 40-80 DEG C of vacuum-drying under Vanadium Pentoxide in FLAKES exists, obtain 1-allyl group-3-methyl-imidazoles dimethyl phosphate salt.
Embodiment 3:
Take N-propargyl imidazoles and trimethyl phosphite 99, make its amount of substance than being 1:1 ~ 1.2, in the alkyl phosphate that N-propargyl imidazoles is dropwise added in ice-water bath, stirred, after dripping, by mixture heat to 50-90 DEG C, stirred at reflux condition reaction 9-48h, be extracted with ethyl acetate mix products 3-8 time again, desolventize 50-80 DEG C of steaming again, finally again by products therefrom 40-80 DEG C of vacuum-drying under Vanadium Pentoxide in FLAKES exists, obtain 1-propargyl-3-methyl-imidazoles dimethyl phosphate salt.
Embodiment 4:
Take N-n-butene base imidazoles and trimethyl phosphite 99, make its amount of substance than being 1:1 ~ 1.2, in the alkyl phosphate that N-n-butene base imidazoles is dropwise added in ice-water bath, stirred, after dripping, by mixture heat to 50-90 DEG C, stirred at reflux condition reaction 9-48h, be extracted with ethyl acetate mix products 3-8 time again, desolventize 50-80 DEG C of steaming again, last again by products therefrom 40-80 DEG C of vacuum-drying under Vanadium Pentoxide in FLAKES exists, obtain 1-n-butene base-3-methyl-imidazoles dimethyl phosphate salt.
Claims (5)
1. a preparation method for novel ion liquid, is characterized in that: its processing step and condition as follows:
Take unsaturated side base imidazoles and alkyl phosphate, make its amount of substance than being 1:1 ~ 1.2, in the alkyl phosphate that unsaturated side base imidazoles is dropwise added in ice-water bath, stirred, after dripping, by mixture heat to 50-90 DEG C, stirred at reflux condition reaction 9-48h, then be extracted with ethyl acetate mix products 3-8 time, desolventize 50-80 DEG C of steaming again, finally again by products therefrom 40-80 DEG C of vacuum-drying under Vanadium Pentoxide in FLAKES exists;
Unsaturated side base imidazoles and alkyl phosphate reaction expression as follows:
In above-mentioned chemical reaction general formula, described radicals R can be H
2c=CH---H
2c=CH-CH
2-, HC ≡ C-CH
2---, H
2c=CH---CH
2-CH
2---described R
1, R
3be selected from C
1-C
18alkyl, R
2be selected from H and C
1-C
18alkyl.
2. the preparation method of a kind of novel ion liquid according to claim 1, is characterized in that: the amount of described reactant species is than being 1:1 ~ 1.2, and temperature of reaction is 50 to 90 DEG C, and the reaction times is 9 to 48h.
3. the preparation method of a kind of novel ion liquid according to claim 1, is characterized in that: be first dropwise uniformly mixed under frozen water condition by mixed reactant before reaction.
4. the preparation method of a kind of novel ion liquid according to claim 1, is characterized in that: use " one kettle way " reaction, with unsaturated side base imidazoles and alkyl phosphate for raw material, do not add the third solvent any.
5. the preparation method of a kind of novel ion liquid according to claim 1, is characterized in that: with common low poison solvent extraction into ethyl acetate after reaction.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106647355A (en) * | 2016-11-09 | 2017-05-10 | 中国民用航空飞行学院 | Data processing method and system for flight situation environment evaluation |
| TWI678229B (en) * | 2016-06-14 | 2019-12-01 | 德商贏創德固賽有限責任公司 | Process for dehumidifying moist gas mixtures |
| US10493400B2 (en) | 2016-06-14 | 2019-12-03 | Evonik Degussa Gmbh | Process for dehumidifying moist gas mixtures |
| US10500540B2 (en) | 2015-07-08 | 2019-12-10 | Evonik Degussa Gmbh | Method for dehumidifying humid gas mixtures using ionic liquids |
| US10512881B2 (en) | 2016-06-14 | 2019-12-24 | Evonik Degussa Gmbh | Process for dehumidifying moist gas mixtures |
| CN117106332A (en) * | 2023-10-23 | 2023-11-24 | 中国林业科学研究院木材工业研究所 | Flame-retardant amino resin coating for repairing cracks of carbon layer as well as preparation method and application thereof |
| WO2023226344A1 (en) * | 2022-05-26 | 2023-11-30 | 苏州金宏气体股份有限公司 | Ionic liquid composition and preparation method therefor |
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| CN103172754A (en) * | 2013-04-07 | 2013-06-26 | 中国科学院过程工程研究所 | Method for preparing carboxymethylcellulose from ionic liquid |
| CN104529752A (en) * | 2014-12-30 | 2015-04-22 | 浙江大学 | Technology of preparing acetylpropionic acid through continuous biodegradation of cellulose in ionic liquid-water media |
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| CN103172754A (en) * | 2013-04-07 | 2013-06-26 | 中国科学院过程工程研究所 | Method for preparing carboxymethylcellulose from ionic liquid |
| CN104529752A (en) * | 2014-12-30 | 2015-04-22 | 浙江大学 | Technology of preparing acetylpropionic acid through continuous biodegradation of cellulose in ionic liquid-water media |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10500540B2 (en) | 2015-07-08 | 2019-12-10 | Evonik Degussa Gmbh | Method for dehumidifying humid gas mixtures using ionic liquids |
| TWI678229B (en) * | 2016-06-14 | 2019-12-01 | 德商贏創德固賽有限責任公司 | Process for dehumidifying moist gas mixtures |
| US10493400B2 (en) | 2016-06-14 | 2019-12-03 | Evonik Degussa Gmbh | Process for dehumidifying moist gas mixtures |
| US10512881B2 (en) | 2016-06-14 | 2019-12-24 | Evonik Degussa Gmbh | Process for dehumidifying moist gas mixtures |
| US10512883B2 (en) | 2016-06-14 | 2019-12-24 | Evonik Degussa Gmbh | Process for dehumidifying moist gas mixtures |
| CN106647355A (en) * | 2016-11-09 | 2017-05-10 | 中国民用航空飞行学院 | Data processing method and system for flight situation environment evaluation |
| CN106647355B (en) * | 2016-11-09 | 2023-11-07 | 中国民用航空飞行学院 | Data processing method and system for flight scenario environment evaluation |
| WO2023226344A1 (en) * | 2022-05-26 | 2023-11-30 | 苏州金宏气体股份有限公司 | Ionic liquid composition and preparation method therefor |
| CN117106332A (en) * | 2023-10-23 | 2023-11-24 | 中国林业科学研究院木材工业研究所 | Flame-retardant amino resin coating for repairing cracks of carbon layer as well as preparation method and application thereof |
| CN117106332B (en) * | 2023-10-23 | 2023-12-29 | 中国林业科学研究院木材工业研究所 | Flame-retardant amino resin coating for repairing cracks of carbon layer as well as preparation method and application thereof |
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Application publication date: 20151118 |