CN106187903A - A kind of synthetic method of alkali ionic liquid - Google Patents
A kind of synthetic method of alkali ionic liquid Download PDFInfo
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- CN106187903A CN106187903A CN201610768676.4A CN201610768676A CN106187903A CN 106187903 A CN106187903 A CN 106187903A CN 201610768676 A CN201610768676 A CN 201610768676A CN 106187903 A CN106187903 A CN 106187903A
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- ionic liquid
- liquid
- alkali ionic
- synthesis
- synthetic method
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
- B01J31/0282—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aliphatic ring, e.g. morpholinium
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic 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
- C07D233/56—Heterocyclic 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
- C07D233/58—Heterocyclic 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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses the synthetic method of a kind of alkali ionic liquid.The alkali ionic liquid of the present invention uses two-step synthesis method, synthesizes by the way of salt exchanges.It is an advantage of the invention that the advantage both with inorganic base, and simple to operate, have again in water and air stable, it is easily isolated, high catalytic efficiency and the new features of repeatable usability, during base catalysis, provides the probability of a kind of new eco-friendly base catalyst.This alkali ionic liquid because can easily be accommodated, non-volatility, non-corrosiveness and can and many immiscible organic solvents thus show the huge potential quality replacing tradition base catalyst, there is important prospects for commercial application.
Description
Technical field
The invention belongs to technical field of ionic liquid material, be specifically related to the synthetic method of a kind of alkali ionic liquid.
Background technology
Ionic liquid (Ionic Liquids, be called for short ILs) be a class completely by organic cation and inorganic or organic the moon from
Son composition and the fusing point salt less than 100 DEG C.Usually said ionic liquid is ionic liquid at room temperature, and it is attached in room temperature or room temperature
The electrolyte of nearly following one-tenth liquid.Compared with traditional ionic compound, at room temperature it is liquid；With traditional liquid object
Matter is compared, and structurally it is made up of zwitterion again.Therefore, ionic liquid has the physics of uniqueness, chemical property also
Replace the prospect of the unfriendly solvent of traditional environment.
Ionic liquid at room temperature includes acidity, neutrality and alkali ionic liquid.Acidity and neutral ion liquid are by well
Cognition is also used successfully in many organic reactions.But, the relevant report about alkali ionic liquid is the most considerably less.According to
Arrhenius soda acid theory of electrolytic dissociation, can ionize out OH in aqueous-Ionic liquid, i.e. belong to alkali ionic liquid.This kind of
It is OH that ionic liquid is primarily referred to as anion-Alkali ionic liquid, such as alkyl imidazole salt hydroxyl alkaline ionic liquid.Although
The development of alkali ionic liquid is started late, but also experienced by considerably complicated development course.In late 1970s,
AlCl3First type alkali ionic liquid is found, but due to chloroaluminate ionic liquid instability in water, air, its application
By a definite limitation.Start studied to Lewis alkali ionic liquid at the beginning of the nineties, up to the present, had and compared
Kind system.
Traditional liquid alkali catalyst such as triethylamine and pyridine etc., catalysis activity is higher, but catalyst and product are not
Easily separated.Catalyzed by solid base reaction has that selectivity is good and product such as is easily isolated at the advantage, but catalyst preparation is complicated, cost
Costliness, intensity is poor, easily by the CO in air2And H2The impurity such as O pollute.Alkali ionic liquid is owing to having the excellent of inorganic base
Point, stable in water and air, it is easy to separate, high catalytic efficiency and repeatable usability, provide during base catalysis
A kind of probability of new eco-friendly base catalyst.Applying most is that salt exchanges method, can synthesize air and water
Stable ionic liquid, and simple to operate.This kind of strong alkali ionic liquid because can easily be accommodated, non-volatility, non-corrosiveness
And energy with many immiscible organic solvents thus shows the huge potential quality replacing tradition base catalyst, there is important industry and answer
Use prospect.
Summary of the invention
Present disclosure is:
A kind of alkali ionic liquid, it is characterised in that: using two-step synthesis method, by the way of salt exchanges, synthesis obtains
Basic imidazole salt ion liquid.
The synthetic method of the present invention, the first step: N-methyl miaow is joined according to mol ratio 1:1.05 with brominated methans
In there-necked flask, 110 DEG C of magnetic agitation, condensing reflux reaction lh, obtain faint yellow viscous liquid；By liquid crude product second
Acetoacetic ester washs 3 times, decompression distillation, adds acetone, and concussion is dissolved, and adds a small amount of crystal seed, stands 2-3h, precipitation to be crystallized, takes out
Filter acetone, obtains highly purified intermediate, is placed in 70 DEG C of oven dryings to constant weight.
Second step: the synthesis of basic ion liquid, takes appropriate ionic liquid intermediate and is dissolved in the dichloromethane of 50ml, adds
Equimolar granular solids sodium hydroxide, stirs 10h under room temperature, sucking filtration removes NaBr precipitation, and at 40 DEG C, rotary evaporation removes
Solvent, obtains crude product ionic liquid；Taking 20ml absolute ether to wash 3 times, rotary evaporation removes ether, is dried under vacuum at 70 DEG C
Constant weight, obtains thick alkali ionic liquid.
Advantages of the present invention with effect is:
It is simple and direct that the alkali ionic liquid that the present invention synthesizes has synthetic method, and process is environmentally friendly, the product of synthesis
In water and air stable, it is easy to separate, the advantage such as high catalytic efficiency and repeatable usability.
Accompanying drawing explanation
For allowing the preparation process of the present invention become apparent, being described as follows of accompanying drawing:
Fig. 1 illustrates a kind of preparation flow figure according to an embodiment of the present invention.
Detailed description of the invention
Embodiment 1:
The first step: N monomethyl imidazoles and bromination of n-butane are joined in there-necked flask according to mol ratio 1:1.05,110
DEG C magnetic agitation, condensing reflux reaction lh, obtain faint yellow viscous liquid [Bmim] Br, by liquid crude product ethyl acetate
Washing 3 times, decompression distillation, add acetone, concussion is dissolved, and adds a small amount of crystal seed, stands 2-3h, treats [Bmim] Br crystallization,
Sucking filtration acetone, obtains highly purified intermediate [Bmim] Br, is placed in 70 DEG C of vacuum drying ovens and is dried to constant weight.
Second step: the synthesis of alkali ionic liquid [Bmim] oH, takes appropriate ionic liquid intermediate [Bmim] Br and is dissolved in
In the dichloromethane of 50ml, adding equimolar granular solids sodium hydroxide, stir 10h under room temperature, sucking filtration removes NaBr and sinks
Form sediment, rotate evaporation of solvent at 40 DEG C, obtain crude product ionic liquid [Bmim] OH, take 20ml absolute ether and wash 3 times, rotate
Evaporation removes ether, is dried under vacuum to constant weight, obtains brown color thick alkali ionic liquid [Bmim] OH at 70 DEG C.
Embodiment 2:
Brominated methans bromination of n-butane is changed to bromoethane, and other Step By Conditions are constant, available [Emim] [Ac].
Claims (4)
1. the synthetic method of a functionalized ion liquid, it is characterised in that: the method uses two-step synthesis method, is exchanged by salt
Mode, synthesis obtain basic imidazole salt ion liquid.Concretely comprise the following steps:
The first step: N-methyl miaow is joined in there-necked flask with brominated methans according to quantitative mol ratio, certain reaction
Condition, obtains faint yellow viscous liquid；Liquid crude product ethyl acetate is washed 3 times, decompression distillation, add acetone, shake
Swing dissolving, add a small amount of crystal seed, stand 2-3h, precipitation to be crystallized, sucking filtration acetone, obtain highly purified intermediate, be placed in
70 DEG C of oven dryings are to constant weight.
Second step: the synthesis of basic ion liquid, takes appropriate ionic liquid intermediate and is dissolved in the dichloromethane of 50ml, adds appropriate
Granular solids sodium hydroxide, under room temperature stir 10h, sucking filtration remove NaBr precipitation, at 40 DEG C rotate evaporation of solvent,
To crude product ionic liquid；Taking 20ml absolute ether to wash 3 times, rotary evaporation removes ether, is dried under vacuum to constant weight at 70 DEG C,
To thick alkali ionic liquid.
Method the most according to claim 1, it is characterised in that: in the described first step, N-methyl miaow is pressed with brominated methans
It is 1:1.05 according to mol ratio.
Method the most according to claim 1, it is characterised in that: N-methyl miaow and brominated methans in the described first step
Reaction condition is to be stirred continuously in 110 DEG C of oil baths, condensing reflux 1h.
Method the most according to claim 1, it is characterised in that: the granular solids hydroxide added in described second step
The molal quantity of sodium is equal with the molal quantity of ionic liquid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610768676.4A CN106187903A (en) | 2016-08-30 | 2016-08-30 | A kind of synthetic method of alkali ionic liquid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610768676.4A CN106187903A (en) | 2016-08-30 | 2016-08-30 | A kind of synthetic method of alkali ionic liquid |
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| Publication Number | Publication Date |
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| CN106187903A true CN106187903A (en) | 2016-12-07 |
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| CN201610768676.4A Pending CN106187903A (en) | 2016-08-30 | 2016-08-30 | A kind of synthetic method of alkali ionic liquid |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110862332A (en) * | 2019-11-29 | 2020-03-06 | 山东理工大学 | Green process for synthesizing 0- (3-chloro-2-propenyl) hydroxylamine by taking ionic liquid as solvent |
-
2016
- 2016-08-30 CN CN201610768676.4A patent/CN106187903A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110862332A (en) * | 2019-11-29 | 2020-03-06 | 山东理工大学 | Green process for synthesizing 0- (3-chloro-2-propenyl) hydroxylamine by taking ionic liquid as solvent |
| CN110862332B (en) * | 2019-11-29 | 2022-10-04 | 山东理工大学 | Process for synthesizing O- (3-chloro-2-propenyl) hydroxylamine by taking ionic liquid as solvent |
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Application publication date: 20161207 |