CN106810499A - A kind of ionic liquid and preparation method thereof - Google Patents
A kind of ionic liquid and preparation method thereof Download PDFInfo
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- CN106810499A CN106810499A CN201611058877.1A CN201611058877A CN106810499A CN 106810499 A CN106810499 A CN 106810499A CN 201611058877 A CN201611058877 A CN 201611058877A CN 106810499 A CN106810499 A CN 106810499A
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- CN
- China
- Prior art keywords
- ionic liquid
- parts
- ethyl imidazol
- methyl alcohol
- quaternary ammonium
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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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
Abstract
Ionic liquid, with many unique properties, has tempting prospect as new environment-friendly " green solvent " of a class in many fields.Ionic liquid can be used for separation process, particularly chemical reaction, the aspect such as catalytic reaction and electrochemistry as solvent, and obtain many good experimental results.Ionic liquid is easy to recycle so as to reduce the pollution to environment, is referred to as green solvent.It is Material synthesis N ethyl imidazol(e) ionic liquids, and performance study is carried out to it by mass spectrometric measurement and conductance with methyl alcohol, N ethyl imidazol(e)s, dimethyl carbonate the invention discloses one kind.
Description
Technical field
The present invention relates to chemical field, and in particular to a kind of ionic liquid and preparation method thereof.
Technical background
Ionic liquid is by nitrogen, phosphorus organic cation and big inorganic anion（BF4 ˉ, PF6- etc.）Composition in room temperature and adjacent
Temperature（- 30~50 DEG C）Under completely in ion organic liquid material, be difficult to Mi Dui because its ion has highly asymmetric property
Product, hinders it to crystallize, therefore is liquid under normal temperature, normally referred to as " ionic liquid at room temperature "（Roomtemperature ionic
liquid ).Ionic liquid has many special performances, and is adjusted by its zwitterion, controllable its physics and chemistry
Matter.
The organic cation of ionic liquid is usually：Alkyl-quaternaryammonium cations are abbreviated [NRxH4- x]+；Alkyl quaternary phosphine cation
Brief note [PRxH4- x]+；Alkyl-substituted imidazol ion is abbreviated as [RRIm]+；Alkyl-substituted pyridinium ion is abbreviated as [RPy]+With
Alkyl sulfonium cation etc..Wherein, it is more to alkyl-substituted imidazol ion and the research of alkyl-substituted pyridinium ion.Anion can
Being that inorganic anion can also be organic anion, including hexafluorophosphoricacid acid ions, tetrafluoroborate ion, trifluoromethyl sulphur
Acid ion, double-（Trifluoromethane sulfonic acid）Amine ion, trifluoroacetic acid ion, acetate ion, nitrate ion, halide ion
Deng.
Ionic liquid has liquid range wide, and this causes many reactions in ionic liquid to have the excellent dynamics can
Control property.It is generally acknowledged that, the symmetry of cationic structural is lower, and ion interphase interaction is weaker, and cation charge distribution is uniform, then
Its fusing point is lower;Anion volume increases, and can also promote fusing point to reduce.The fusing point of ionic liquid is mostly in 0~100 DEG C of model
In enclosing.Researcher also found many ionic liquids in -80~100 DEG C or so the glassy states shown in wide temperature range,
This illustrates that their crystallization rate is very slow, and with considerably long melting range.The heat endurance of ionic liquid receives carbon-heterodesmic respectively
With the influence of Hyarogen-bonding, still there is preferable heat endurance typically when higher than 200 DEG C.Water content is to its heat endurance
In the presence of influence.
The density of ionic liquid it is main by the type of zwitterion depending on, imidazoles system ionic liquid normal temperature (291~303K)
Density is substantially in 1.1~1.7gcm-3Between.The length of the density of ionic liquid and N- alkyl chains on imidazoles salt cation is almost
It is linear, while can also reduce with the increase of its organic cation volume.Usual anion is bigger, ionic liquid
Density is bigger.
The viscosity of ionic liquid is mainly determined that the influence of hydrogen bond is clearly by hydrogen bond and Van der Waals force.Under normal temperature its
Viscosity is larger (being tens times of water).Its viscosity is reduced with the rising of temperature;With the growth of cationic substituent carbochain
Increase.Anion is [N (CN)2]-Ionic liquid viscosity it is generally relatively low.For the ionic liquid of aluminium chlorate class, work as ionic liquid
When body is for alkalescence, i.e. x (AlCl3)<When 0.5, because exist substantial amounts of chlorion make hydrogen atom on imidazoles salt cation and chlorine from
Hydrogen bond action between son is strengthened and causes the viscosity of ionic liquid to increase;When ionic liquid is for acidity, i.e. x (AlCl3)>
When 0.5, because the chlorion for existing seldom weakens the hydrogen bond action between hydrogen atom and chlorion on imidazoles salt cation, this
When ionic liquid viscosity decline.Its viscosity increases and increases with the volume of anion when cation is identical.
There is sizable Coulomb force in the dissolubility of ionic liquid, exactly this coulomb compared with other solvents, inside it
Power makes it have very strong polarity and has special solvability to various organic and inorganic and polymeric material.It is good using its
Dissolubility, can be by the strong Bronsted acid of some polarity and Lewis acid and metal complex catalyst dissolving, and reaching catalyst circulation makes
Purpose.Substitution alkyl carbon chain lengths on glyoxaline cation have considerable influence to amphipathic property.It is both BF4 -Anion,
At 25 DEG C, when the carbon number of alkyl is more than 5, ionic liquid is water insoluble;During less than 5, ionic liquid is then miscible with water.For hexafluoro
The alkyl-substituted glyoxaline ion liquid of phosphate anion, its hydrophobicity gradually increases with the increase of kation alkyl chain length
Greatly.Swatlosk etc. has found, in H2O and ionic liquid [C4mim]PF6In the diphasic system of composition, introducing third component also can shadow
Dissolubility between each phase of sound, this provides wide sky to reconcile dissolubility of the material between ionic liquid and other solvents
Between, from this point it can be seen that, by design and regulation ionic liquid can realize its replace volatile organic molecular solvents from
Some organic compounds of extract and separate are possible in the aqueous solution.
Room-temperature imidazolium-based ionic liquids material as a kind of new material because of its unique physicochemical property, in organic chemistry, electricity
Chemistry and separation process show good application prospect.Research both at home and abroad increasing in recent years is to imidazoles room-temperature ion
The preparation of fluent material, property and its application conduct extensive research report, are not only because room-temperature imidazolium-based ionic liquids
Material can dissolve various inorganic matters as catalyst carrier, can also dissolve gas chromatography so that reaction efficiency, separation effect
Rate is higher, and selectivity is more preferably.The application of room-temperature imidazolium-based ionic liquids material can mitigate environmental pollution, reduce disappearing for solvent
Consumption, new approaches are provided for people find green material.
The content of the invention
The present invention is Material synthesis N- ethyl imidazol(e) ionic liquids, and passes through by with methyl alcohol, N- ethyl imidazol(e)s, dimethyl carbonate
Infrared test, nuclear magnetic resonance test, mass spectrometric measurement and conductance carry out performance study to it.
To achieve these goals, the technical scheme taken：
A kind of ionic liquid, it is characterised in that raw material include the raw material of following weight portion：
Methyl alcohol：20 ~ 60 parts of N- ethyl imidazol(e)s：20 ~ 50 parts of dimethyl carbonates：20 ~ 50 parts.
Preferably, a kind of ionic liquid, the raw material comprising following weight portion：
Methyl alcohol：30 ~ 40 parts of N- ethyl imidazol(e)s：30 ~ 40 parts of dimethyl carbonates：30 ~ 40 parts.
Preferably, a kind of ionic liquid, the raw material comprising following weight portion：
Methyl alcohol：30 parts of N- ethyl imidazol(e)s：35 parts of dimethyl carbonates：35 parts.
A kind of preparation technology of core pattern ionic liquid, the technique is comprised the following steps：
1st step：The synthesis of N- ethyl imidazol(e) quaternary ammonium salts
Methyl alcohol, N- ethyl imidazol(e)s, dimethyl carbonate are added in autoclave, it is vacuumized by water pump, temperature
Control is reacted at 130 DEG C, and reaction obtains light yellow product after terminating, and the reaction equation is：
。
Moisture removal is removed into product distillation.
Second step：The synthesis of the ionic liquid of quaternary ammonium salt
A certain amount of methyl alcohol is taken out plus appropriate（40%）HBF4Mixing, is titrated with appropriate quaternary ammonium salt（Determined to use according to amine value
Amount）, titrated in 90 minutes, then allow solution reaction 30 minutes.
The reaction equation is：
。
Product is stored in molecular sieve with being not added with the bottle of molecular sieve respectively.
Further, the N- ethyl imidazol(e) purity content for being used is 99%.
Further, the fluoboric acid purity for being used is 40.9%.
Beneficial effect：The beneficial effects of the present invention are one kind is provided with N- ethyl imidazol(e)s as raw material, with dimethyl carbonate
N- ethyl imidazol(e) quaternary ammonium salts are obtained with methyl alcohol reaction.Reacted with quaternary ammonium salt and boron fluoric acid again and obtain N- ethyl imidazol(e) ionic liquids
Mode.
Brief description of the drawings：
Accompanying drawing 1 is a kind of obtained N- ethyl imidazol(e)s quaternary ammonium salt of the novel ion liquid in embodiment 1-4 and preparation method thereof
The mass spectrogram of molecular weight.
Specific embodiment
The technical problems to be solved by the invention are to provide a kind of novel ion liquid and preparation method thereof.
Technical scheme includes the synthesis of the ionic liquid of the synthesis and quaternary ammonium salt of N- ethyl imidazol(e) quaternary ammonium salts.
Embodiment 1
1st, the synthesis of imidazoles quaternary ammonium salt
30 parts by weight Methanol, 35 weight portion N- ethyl imidazol(e)s, 35 weight portion dimethyl carbonates are added in autoclave, is passed through
Water pump is vacuumized to it, and temperature control is reacted at 130 DEG C, and reaction obtains light yellow product after terminating, the reaction side
Formula is：
。
2nd, the synthesis of the ionic liquid of quaternary ammonium salt
A certain amount of methyl alcohol is taken out plus appropriate（40%）HBF4Mixing, is titrated with appropriate quaternary ammonium salt（Determined to use according to amine value
Amount）, titrated in 90 minutes, then allow solution reaction 30 minutes.
The reaction equation is：
。
Embodiment 2
1st, the synthesis of imidazoles quaternary ammonium salt
20 parts by weight Methanol, 40 weight portion N- ethyl imidazol(e)s, 40 weight portion dimethyl carbonates are added in autoclave, is passed through
Water pump is vacuumized to it, and temperature control is reacted at 130 DEG C, and reaction obtains light yellow product after terminating, the reaction side
Formula is：
。
2nd, the synthesis of the ionic liquid of quaternary ammonium salt
A certain amount of methyl alcohol is taken out plus appropriate（40%）HBF4Mixing, is titrated with appropriate quaternary ammonium salt（Determined to use according to amine value
Amount）, titrated in 90 minutes, then allow solution reaction 30 minutes.
The reaction equation is：
。
Embodiment 3
1st, the synthesis of imidazoles quaternary ammonium salt
40 parts by weight Methanol, 30 weight portion N- ethyl imidazol(e)s, 30 weight portion dimethyl carbonates are added in autoclave, is passed through
Water pump is vacuumized to it, and temperature control is reacted at 130 DEG C, and reaction obtains light yellow product after terminating, the reaction side
Formula is：
2nd, the synthesis of the ionic liquid of quaternary ammonium salt
A certain amount of methyl alcohol is taken out plus appropriate（40%）HBF4Mixing, is titrated with appropriate quaternary ammonium salt（Determined to use according to amine value
Amount）, titrated in 90 minutes, then allow solution reaction 30 minutes.
The reaction equation is：
。
Embodiment 4
The present embodiment carries out mass spectrometric measurement and conductance and carries out performance study to it to embodiment 1 ~ 3.
Being calculated by molecular formula can show that N- ethyl imidazol(e) quaternary ammonium salts molecular weight obtains the molecule of mass spectrometric measurement for 111,3 embodiments
Amount is 111, it was demonstrated that the first step product of the preparation method is N- ethyl imidazol(e) quaternary ammonium salts.
Finally it should be noted that the above embodiments are merely illustrative of the technical solutions of the present invention rather than the present invention is protected
The limitation of scope, although being elaborated to the present invention with reference to preferred embodiment, one of ordinary skill in the art should manage
Solution, can modify or equivalent, without deviating from the essence and model of technical solution of the present invention to technical scheme
Enclose.
Claims (6)
1. a kind of ionic liquid, it is characterised in that raw material include the raw material of following weight portion：
Methyl alcohol：20 ~ 60 parts of N- ethyl imidazol(e)s：20 ~ 50 parts of dimethyl carbonates：20 ~ 50 parts.
2. a kind of ionic liquid according to claim 1, it is characterised in that the raw material comprising following weight portion：
Methyl alcohol：30 ~ 40 parts of N- ethyl imidazol(e)s：30 ~ 40 parts of dimethyl carbonates：30 ~ 40 parts.
3. a kind of ionic liquid according to claim 1, it is characterised in that the raw material comprising following weight portion：
Methyl alcohol：30 parts of N- ethyl imidazol(e)s：35 parts of dimethyl carbonates：35 parts.
4. a kind of ionic liquid according to claim 1, it is characterised in that the molecular formula of described ionic liquid is。
5. the preparation of a kind of ionic liquid according to claim 1, it is characterised in that carried out using two-part reaction method
Prepare, comprise the following steps：
（1）The synthesis of N- ethyl imidazol(e) quaternary ammonium salts:
A certain proportion of methyl alcohol, N- ethyl imidazol(e)s, dimethyl carbonate are added in autoclave, it is taken out by water pump
Vacuum, temperature control is reacted at 130 DEG C, and reaction obtains light yellow product after terminating, and the reaction equation is：
Moisture removal is removed into product distillation；
（2）The synthesis of the ionic liquid of quaternary ammonium salt:
Take out the HBF that a certain amount of methyl alcohol is plus appropriate 40%4Mixing, is titrated with appropriate quaternary ammonium salt, has been titrated in 90 minutes, then
Allow solution reaction 30 minutes, the reaction equation is：
。
6. a kind of preparation method of ionic liquid according to claim 5, it is characterised in that the fluoboric acid purity for being used
It is 40.9%.
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| CN201611058877.1A CN106810499A (en) | 2016-11-28 | 2016-11-28 | A kind of ionic liquid and preparation method thereof |
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| CN201611058877.1A CN106810499A (en) | 2016-11-28 | 2016-11-28 | A kind of ionic liquid and preparation method thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112299968A (en) * | 2020-11-26 | 2021-02-02 | 山东卓俊实业有限公司 | Preparation method of chemical raw material |
Citations (3)
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|---|---|---|---|---|
| CN1669100A (en) * | 2002-07-26 | 2005-09-14 | 三洋化成工业株式会社 | Electrolyte for electrochemical capacitor and electrochemical capacitor containing the same |
| CN101633641A (en) * | 2009-08-11 | 2010-01-27 | 华南师范大学 | Preparation method of imidazole type ionic liquid |
| CN101987824A (en) * | 2009-07-31 | 2011-03-23 | 武汉凯门化学有限公司 | Preparation method of high-purity conductive salt for super capacitor |
-
2016
- 2016-11-28 CN CN201611058877.1A patent/CN106810499A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1669100A (en) * | 2002-07-26 | 2005-09-14 | 三洋化成工业株式会社 | Electrolyte for electrochemical capacitor and electrochemical capacitor containing the same |
| CN101987824A (en) * | 2009-07-31 | 2011-03-23 | 武汉凯门化学有限公司 | Preparation method of high-purity conductive salt for super capacitor |
| CN101633641A (en) * | 2009-08-11 | 2010-01-27 | 华南师范大学 | Preparation method of imidazole type ionic liquid |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112299968A (en) * | 2020-11-26 | 2021-02-02 | 山东卓俊实业有限公司 | Preparation method of chemical raw material |
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Application publication date: 20170609 |