CN101092399A - Method for preparing ionic liquid with anion being as ion in halogen family - Google Patents
Method for preparing ionic liquid with anion being as ion in halogen family Download PDFInfo
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Abstract
This invention relates to a method for preparing an ionic liquid with halogen anions. The method comprises: (1) uniformly mixing compound (I) and halogenated hydrocarbon (II) at a mol. ratio of 1:(1.0-1.05) at normal temperature; (2) adding into a reaction kettle, reacting at room temperature to 150 deg.C under 0.105-0.25 MPa for 0.5-20 h, recovering the pressure to normal pressure after the reaction, cooling, extracting with 1/5-4/5 volume ethyl acetate for 2-3 times, and vacuum-distilling at 40-80 deg.C for purification. The method has such advantages as rapid reaction, short time and low cost, and is environmentally friendly. The prepared ionic liquid can be used as the solvent for organic reactions and polymerizations, and in chemical separation and electrochemical field.
Description
Technical field
The invention belongs to the ionic liquid preparing technical field, particularly relating to a kind of negatively charged ion is halogen family ionic preparation method of ionic liquid.
Background technology
Ionic liquid at room temperature is compared with conventional solvent, and fusing point is low, and the boiling point height is non-volatile, exists with liquid state in wide temperature range, and good thermostability is arranged; Can change its physicochemical property by the yin, yang ionic combination of selecting to suit, be the good solvent of many organism, inorganics and macromolecular material.Ionic liquid is widely used in electrochemistry, organic synthesis, catalysis as a kind of green solvent and the field such as separates, and also is the good solvent of many macromolecular polymerization reactions and processing simultaneously.Therefore, be considered to the friendly type solvent of novel environmental that has bright prospects in the synthetic and cleaner production of a kind of green.
Preparation method of ionic liquid is divided into two kinds usually: a kind of is that raw material reacts with halohydrocarbon with containing the cationic organism of target, and final synthetic anionic is a halogen family ionic ionic liquid.Second kind is is halogen family ionic ionic liquid with the negatively charged ion and contains the anionic organism of target or inorganics is a raw material, carries out ion exchange reaction, and final synthetic anionic is the target anion ion liquid.
To sum up, no matter synthesize which kind of ionic liquid, negatively charged ion is that the halogen family ionic is ion liquid synthetic all essential.
As far back as people ([J] .Inorg Chem such as nineteen eighty-two Wilkes, 1982,21:1263～1264) be raw material with N-Methylimidazole and halogenated alkane just, being solvent with conventional solvents such as acetonitriles is being lower than the methyl alkyl imidazolium halides of having passed through the quaterisation one-step synthesis under 100 ℃ the experiment condition.But the shortcoming of this method is to need solvent in building-up process.In order to address this problem, people such as Huddleston ([J] .Chem Commun, 1998,18:1765～1766) according to etc. mol ratio reinforced, at 70 ℃, reaction times reaches under 72 hours the condition has realized the muriatic solvent-free preparation of 1-butyl 3-Methylimidazole, has obtained the higher ionic liquid of product purity.Its defective is a long reaction time, and efficient is low.Along with the expansion of ionic liquid Application Areas, corresponding ion liquid synthetic method is also progressively being improved, and as synthesizing of functionalized ion liquid, Chinese patent CN1782043A provides a kind of synthetic method of ion liquid lubricant.Mainly be with imidazolyl ionic liquid and quaternary phosphonium ionic liquid by weight concentration be respectively 5～95% and 95%～5% mix after, obtain by vibration, ultrasonic dispersing.Resulting ion liquid lubricant has that volatility is low, thermostability and the good characteristics of sticking warm nature tool; The improvement of ionic liquid synthetic technology for another example, it is raw material that 200510011377.8 of Chinese patents adopt 1: 1～1: 1.1 N-alkyl imidazole of mol ratio and halohydrocarbon, under normal pressure, realize addition reaction in the closed reactor, synthetic by N, the ionic liquid that N-dialkylimidazolium positively charged ion and halide anion are formed, and utilize supercritical CO
2Extracting and separating reaction product and unreacted raw material.It is raw material that Chinese patent 200610033301.X adopts the N-alkyl imidazole and the halohydrocarbon of certain mol proportion (1: 1.1～1: 1.5), uses CO
2Come the air in the metathesis reactor to carry out quaterisation, be synthesizing halogen alkyl imidazole type ionic liquid under the condition of room temperature～150 ℃ in temperature of reaction, and use supercritical CO
2Extract excessive halogenated alkane.02155945.7 of patent discloses a kind of synthetic method that contains the ionic liquid at room temperature of unsaturated double-bond.Mainly be to be to mix mutually in 1.1: 1～1.9: 1 in molar ratio with a haloolefin R1X and N-alkyl imidazoles, after temperature is 10～100 ℃ of following stoichiometric numbers hour, obtain ionic liquid dialkyl imidazolium halide drone.
In the above-mentioned reaction method, its common trait is: be reflected under the normal pressure and carry out, temperature of reaction is controlled near the boiling point of halohydrocarbon, and the mode of employing condensing reflux is controlled the activity and the loss of reactant.Therefore, existing problem is:
(1) reaction times longer, reaction often needs reflux more than 24 hours, and transformation efficiency is low.
(2) adopt the excessive method of halohydrocarbon to improve reaction conversion ratio, increased the solvent load and the washing times of product washing purifying, cost rises.
Patent CN1188211C discloses a kind of employing microwave-assisted and has prepared ion liquid method, but the technology of microwave method is difficult to control, and the thermal effect of microwave and electric field action easily cause reaction mass overheated and influence quality product, and can't scale operation.Patent 200410018529.2 discloses a kind of ion liquid synthetic method.It uses the supersonic cell crusher under the condition of 740W～760W, to mol ratio is that 1: 1.0～1: 1.1 the Methylimidazole and the mixed solution of hydrobromic ether carry out supersound process, 0.5～1 hour postcooling, use the ethyl acetate extraction 2～3 times of equal volume then, obtain water soluble ion liquid after 6～8 hours 60 ℃～80 ℃ vacuum-dryings.This method influences product quality owing to utilize high-power ultrasonication to cause reaction too fierce easily, has increased the cost of purification of products.
Summary of the invention
It is halogen family ionic preparation method of ionic liquid that technical problem to be solved by this invention provides a kind of negatively charged ion, and this method has overcome the defective of prior art, and speed of reaction is fast, and the time is short, and cost is low, and is environmentally friendly.
A kind of negatively charged ion of the present invention is a halogen family ionic preparation method of ionic liquid, comprises the following steps: that (1) will contain the cationic compound of target (I) is 1: 1.0～1: 1.05 with halon (II) in molar ratio, at normal temperatures uniform mixing;
(2) add in the reactor, the control reacting kettle inner pressure is 0.105～0.25MPa in the reaction process, temperature of reaction is room temperature～150 ℃, and the reaction times is 0.5～20 hour, after reaction finishes, discharge the still internal pressure to normal pressure, cool to room temperature is with the ethyl acetate extraction of 1/5～4/5 volume 2～3 times, then 40～80 ℃ of following underpressure distillation, carry out purifying, productive rate＞90%.Described compound (I) is selected from a kind of in the following compounds:
Alkyl quaternary ammonium hydroxyethyl alkyl quaternary ammonium alkyl sulfonium alkyl quaternary phosphonium
Alkyl pyridine alkyl pyrroles alkyl pyrazoles alkyl imidazoles
Wherein: R1, R2, R3, R4, R5 and R6 can be identical, also can be different, they are respectively that H or carbonatoms are the alkyl of 1-8.
The general formula of described compound (II) is R-X
Wherein: R is that carbonatoms is the alkyl of 1-8, and X is a kind of among Cl, the Br.
Described positively charged ion is following a kind of:
Alkyl quaternary ammonium ion hydroxyethyl alkyl quaternary ammonium ion alkyl sulfonium cation alkyl quaternary phosphonium ion
Alkyl pyridinium ion alkyl pyrroles ion alkyl pyrazoles ion alkyl imidazol ion
Wherein: R1, R2, R3, R4, R5 and R6 can be identical, also can be different, they are respectively that H or carbonatoms are the alkyl of 1-8.
Negatively charged ion is Cl
-, Br
-In a kind of.
Pressure-controlling in the described reactor of step (2) can be selected a kind of of following mode for use, by the vaporization control pressure of halohydrocarbon or by control pressures such as rare gas element such as nitrogen, carbonic acid gas.
Described preparation method, it is synthetic to be used for the laboratory, also can be used for suitability for industrialized production.
Described ionic liquid can be used as the solvent of organic reaction, polyreaction, also can be used for chemical separating and electrochemical reaction.
The invention has the beneficial effects as follows:
Adopt the method for controlling reactor internal pressure of the present invention, accelerated speed of response, reduced the excessive ratio of halohydrocarbon, reduced halohydrocarbon in the reaction process because the loss that volatilization causes, reduced the consumption of solvent in the purge process, reduce the cost recovery of unreacted reactant, improved reaction efficiency.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment only to be used to the present invention is described and be not used in and limit the scope of the invention.Should be understood that in addition those skilled in the art can make various changes or modifications the present invention after the content of having read the present invention's instruction, these equivalent form of values fall within the application's appended claims institute restricted portion equally.
Embodiment 1
In the pressurizeed closed reaction kettle of 250ml, add 41.055g (0.500mol) N-Methylimidazole and 46.300g (0.500mol) n-propylcarbinyl chloride successively, at room temperature stir and make it to mix and feed N
2The reactor that reaction mixture will be housed behind the 5min is heated to 85 ℃, control still internal pressure is to 0.12MPa, react after 8 hours, stop to stir, discharge the still internal pressure to normal pressure, behind the question response thing cool to room temperature, taking out reaction product and with the ethyl acetate extraction of 20ml 3 times, obtain the ionic liquid 85.695g of 1-butyl 3-Methylimidazole chlorate again at 80 ℃ of following underpressure distillation 0.5h, is 98.1% with the productive rate of the calculating of N-Methylimidazole.
Embodiment 2
Add 41.055g (0.500mol) N-Methylimidazole and 38.648g (0.505mol) chlorallylene in the pressurizeed closed reaction kettle of 250m1 successively, at room temperature agitation and dropping makes it to mix and feed N
2The reactor that reaction mixture will be housed behind the 25min is heated to 70 ℃, control still internal pressure is to 0.16MPa, react after 0.5 hour, stop to stir, discharge the still internal pressure to normal pressure, behind the question response thing cool to room temperature, taking out reaction product and with the ethyl acetate extraction of 25ml 3 times, obtain the ionic liquid 74.164g of 1-allyl group 3-Methylimidazole chlorate again at 40 ℃ of following underpressure distillation 0.8h, is 93.5% with the productive rate of the calculating of N-Methylimidazole.
Embodiment 3
In the pressurizeed closed reaction kettle of 250ml, add 41.055g (0.500mol) N-Methylimidazole and 68.515g (0.500mol) bromination of n-butane successively, at room temperature stir and make it to mix and feed N
2The reactor that reaction mixture will be housed behind the 5min is heated to 110 ℃, control still internal pressure is to 0.2MPa, react after 2 hours, stop to stir, discharge the still internal pressure to normal pressure, behind the question response thing cool to room temperature, taking out reaction product and with the ethyl acetate extraction of 56ml 3 times, obtain the ionic liquid 103.763g of 1-butyl 3-Methylimidazole Bromide again at 75 ℃ of following underpressure distillation 1.2h, is 94.7% with the productive rate of the calculating of N-Methylimidazole.
Embodiment 4
Add 41.050g (0.500mol) N-methylpyrazole and 56.125g (0.515mol) monobromethane in the pressurizeed closed reaction kettle of 250ml successively, at room temperature agitation and dropping makes it to mix and feed N
2The reactor that reaction mixture will be housed behind the 30min is heated to 50 ℃, control still internal pressure is to 0.15MPa, react after 1 hour, stop to stir, discharge the still internal pressure to normal pressure, behind the question response thing cool to room temperature, taking out reaction product and with the ethyl acetate extraction of 60ml 2 times, obtain the ionic liquid 89.330g of 1-ethyl 3-Methylimidazole Bromide again at 75 ℃ of following underpressure distillation 1.5h, is 93.5% with the productive rate of the calculating of N-methylpyrazole.
Embodiment 5
Add 41.050g (0.500mol) N-methylpyrazole and 40.178g (0.525mol) chlorallylene in the pressurizeed closed reaction kettle of 250ml successively, at room temperature agitation and dropping makes it to mix and feed N
2The reactor that reaction mixture will be housed behind the 30min is heated to 50 ℃, control still internal pressure is to 0.105MPa, react after 2.5 hours, stop to stir, discharge the still internal pressure to normal pressure, behind the question response thing cool to room temperature, taking out reaction product and with the ethyl acetate extraction of 64ml 2 times, obtain the ionic liquid 73.287g of 1-allyl group 2-methylpyrazole chlorate again at 65 ℃ of following underpressure distillation 1.4h, is 92.4% with the productive rate of the calculating of N-methylpyrazole.
Embodiment 6
In the pressurizeed closed reaction kettle of 10L, add 1.58Kg (20mol) pyridine and 2.69Kg (20mol) chloro octane successively, at room temperature stir and make it to mix, the reactor that reaction mixture will be housed behind the 20min is heated to 85 ℃, control still internal pressure is to 0.105MPa, react after 20 hours, stop to stir, discharge the still internal pressure to normal pressure, behind the question response thing cool to room temperature, the ethyl acetate extraction of taking-up reaction product and usefulness 5L 3 times, obtaining the ionic liquid 3.88Kg of 1-butyl-pyridinium chlorate again at 75 ℃ of following underpressure distillation 2h, is 91% with the productive rate of the calculating of pyridine.
Embodiment 7
In the pressurizeed closed reaction kettle of 250ml, add 42.575g (0.500mol) N-methylpyrrole and 55.580g (0.510mol) monobromethane successively, at room temperature stir and make it to mix and feed N
2Control still internal pressure is to 0.105MPa behind the 5min, react after 8 hours, stop to stir, discharge the still internal pressure to normal pressure, behind the question response thing cool to room temperature, the ethyl acetate extraction of taking-up reaction product and usefulness 55ml 3 times, obtaining the ionic liquid 92.988g of 1-ethyl-methyl pyrroles chlorate again at 70 ℃ of following underpressure distillation 1h, is 95.8% with the productive rate of the calculating of N-methylpyrrole.
Embodiment 8
In the pressurizeed closed reaction kettle of 250ml, add 50.595g (0.500mol) triethylamine and 68.515g (0.500mol) bromination of n-butane successively, at room temperature stir and make it to mix and feed N
2The reactor that reaction mixture will be housed behind the 5min is heated to 100 ℃, control still internal pressure is to 0.25MPa, react after 2 hours, stop to stir, discharge the still internal pressure to normal pressure, behind the question response thing cool to room temperature, taking out reaction product and with the ethyl acetate extraction of 75ml 3 times, obtain the ionic liquid 115.179g of triethyl butyl ammonium chloride again at 80 ℃ of following underpressure distillation 1.2h, is 96.7% with the productive rate of the calculating of triethylamine.
Embodiment 9
In the pressurizeed closed reaction kettle of 250ml, add 59.080g (0.500mol) triethyl phosphine and 54.49g (0.500mol) monobromethane successively, at room temperature stir and make it to mix and feed C0
2The reactor that reaction mixture will be housed behind the 5min is heated to 50 ℃, control still internal pressure is to 0.18MPa, react after 2 hours, stop to stir, discharge the still internal pressure to normal pressure, behind the question response thing cool to room temperature, taking out reaction product and with the ethyl acetate extraction of 45ml 3 times, obtain the ionic liquid 108.232g of tetraethyl-bromination squama again at 55 ℃ of following underpressure distillation 1h, is 95.3% with the productive rate of the calculating of triethyl phosphine.
Embodiment 10
In the pressurizeed closed reaction kettle of 250ml, add 44.570g (0.500mol) dimethylethanolamine and 48.152g (0.520mol) n-propylcarbinyl chloride successively, at room temperature stir and make it to mix and feed N
2The reactor that reaction mixture will be housed behind the 5min is heated to 95 ℃, control still internal pressure is to 0.16MPa, react after 12 hours, stop to stir, discharge the still internal pressure to normal pressure, behind the question response thing cool to room temperature, taking out reaction product and with the ethyl acetate extraction of 84ml 2 times, obtain the ionic liquid 89.416g of dimethylbutyl ethanol ammonium chloride again at 70 ℃ of following underpressure distillation 1.25h, is 98.4% with the productive rate of the calculating of dimethylethanolamine.
Claims (7)
1. a negatively charged ion is a halogen family ionic preparation method of ionic liquid, comprises the following steps:
(1) with mol ratio is 1: 1.0～1: 1.05 compound (I) and halon (II) uniform mixing at normal temperatures;
(2) add in the reactor, pressure 0.105～0.25MPa, room temperature～150 ℃, 0.5～20 hour time, after reaction finishes, discharge the still internal pressure to normal pressure, cooling, with the ethyl acetate extraction of 1/5～4/5 volume 2～3 times, 40～80 ℃ of underpressure distillation purifying.
Described compound (I) is selected from a kind of in the following compounds:
Alkyl quaternary ammonium hydroxyethyl alkyl quaternary ammonium alkyl sulfonium alkyl quaternary phosphonium
Alkyl pyridine alkyl pyrroles alkyl pyrazoles alkyl imidazoles
Wherein: R1, R2, R3, R4, R5 and R6 can be identical, also can be different, they are respectively that H or carbonatoms are the alkyl of 1-8.
The general formula of described halon (II) is R-X:
Wherein: R is that carbonatoms is the alkyl of 1-8, and X is a kind of among Cl, the Br.
2. a kind of negatively charged ion according to claim 1 is a halogen family ionic preparation method of ionic liquid, it is characterized in that: described ion liquid positively charged ion is following a kind of:
Alkyl quaternary ammonium ion hydroxyethyl alkyl quaternary ammonium ion alkyl sulfonium cation alkyl quaternary phosphonium ion
Alkyl pyridinium ion alkyl pyrroles ion alkyl pyrazoles ion alkyl imidazol ion
Wherein: R1, R2, R3, R4, R5 and R6 can be identical, also can be different, they are respectively that H or carbonatoms are the alkyl of 1-8.
3. a kind of negatively charged ion according to claim 1 is a halogen family ionic preparation method of ionic liquid, it is characterized in that: described ion liquid negatively charged ion is Cl
-Or Br
-
4. a kind of negatively charged ion according to claim 1 and 2 is a halogen family ionic preparation method of ionic liquid, it is characterized in that: described compound (I) is a kind of in N-Methylimidazole, N-methylpyrazole, pyridine, N-methylpyrrole, triethylamine, triethyl phosphine, the dimethylethanolamine.
5. be halogen family ionic preparation method of ionic liquid according to claim 1 or 3 described a kind of negatively charged ion, it is characterized in that: a kind of in the n-propylcarbinyl chloride, chlorallylene, bromination of n-butane, monobromethane, chlorallylene, chloro octane, monobromethane, bromination of n-butane, n-propylcarbinyl chloride of described halon (II).
6. a kind of negatively charged ion according to claim 1 is a halogen family ionic preparation method of ionic liquid, it is characterized in that: the pressure-controlling in the described reactor of step (2) is for the vaporization control pressure by halohydrocarbon or by rare gas element such as nitrogen, carbonic acid gas control pressure.
7. be halogen family ionic preparation method of ionic liquid according to the described a kind of negatively charged ion of claim 1-8, it is characterized in that: described preparation method is used for the laboratory and synthesizes or be used for suitability for industrialized production.
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Application publication date: 20071226 |