CN1304376C - Method for preparing ion liquid in halogenated alkyl imidazole type - Google Patents
Method for preparing ion liquid in halogenated alkyl imidazole type Download PDFInfo
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- CN1304376C CN1304376C CNB2005100113778A CN200510011377A CN1304376C CN 1304376 C CN1304376 C CN 1304376C CN B2005100113778 A CNB2005100113778 A CN B2005100113778A CN 200510011377 A CN200510011377 A CN 200510011377A CN 1304376 C CN1304376 C CN 1304376C
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- supercritical
- continuous extraction
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- alkyl imidazole
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 238000000034 method Methods 0.000 title claims abstract description 23
- -1 halogenated alkyl imidazole Chemical compound 0.000 title claims abstract description 16
- 239000007788 liquid Substances 0.000 title claims description 19
- 239000002994 raw material Substances 0.000 claims abstract description 25
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 12
- 238000007259 addition reaction Methods 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 238000000605 extraction Methods 0.000 claims description 21
- 150000005826 halohydrocarbons Chemical class 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 abstract description 17
- 239000002608 ionic liquid Substances 0.000 abstract description 13
- 239000003960 organic solvent Substances 0.000 abstract description 6
- 150000008282 halocarbons Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 10
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 9
- 239000000376 reactant Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 3
- WHLZPGRDRYCVRQ-UHFFFAOYSA-N 1-butyl-2-methylimidazole Chemical class CCCCN1C=CN=C1C WHLZPGRDRYCVRQ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- GMGLGUFSJCMZNT-UHFFFAOYSA-N BrCCCCCC.BrCCCCCC Chemical compound BrCCCCCC.BrCCCCCC GMGLGUFSJCMZNT-UHFFFAOYSA-N 0.000 description 1
- WHOKBKXRGWNZRS-UHFFFAOYSA-N CC=1NC=CN1.[Br] Chemical compound CC=1NC=CN1.[Br] WHOKBKXRGWNZRS-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a method for preparing ionic liquid in halogenated alkyl imidazole type, which relates to a new method for preparing ionic liquid. In the method of the present invention, N-alkylimidazole and halogenated hydrocarbon with approximately the same molar weight are used as raw material for addition reaction in a closed reactor at ordinary pressure, so that ionic liquid composed of N, N-dialkyl imidazole positive ions and halogen negative ions is synthesized; reaction products and unreacted raw material are extracted and separated by supercritical CO2. The method avoids using the raw material of excessive halogenated hydrocarbon, and no organic solvent is used in the process of separating and purifying the ionic liquid of the reaction products. The method for preparing ionic liquid has the advantages of simple operation, high efficiency and cleanness, and is suitable for the synthesization of laboratory scale and also for industrial production.
Description
Technical field
The invention belongs to the chemical material preparing technical field, relate to a kind of ion liquid new preparation process.Present method is applicable to that with N-alkyl imidazole and halohydrocarbon be raw material, the synthetic ion liquid occasion of being made up of N, N-dialkylimidazolium positively charged ion and halide anion.
Background technology
Ionic liquid is meant the material that is made of ion that is in a liquid state under near the temperature room temperature.Liquid wide ranges, soluble end are wide because ionic liquid has, low volatility, high stability, electrochemical window are wide, peculiar properties such as recycle can be regulated and be easy to chemical property, applied research at aspects such as sepn process, chemical reaction (especially catalyzed reaction) and electrochemistry has obtained many gratifying results, therefore, be considered to have in the synthetic and cleaner production of a kind of green the novel environmental close friend's of broad prospect of application green solvent.
The ionic liquid that positively charged ion is made up of N, N-dialkylimidazolium ion is a big class ionic liquid that is widely used under study for action at present.Generally, this type of ion liquid route of synthesis all is at first to prepare N, N-dialkylimidazolium halide ions liquid by N-alkyl imidazole and halohydrocarbon addition reaction, makes all kinds of N of containing, the cationic ionic liquid of N-dialkylimidazolium through replacement(metathesis)reaction again.Therefore, N, N-dialkylimidazolium halide ions liquid are the ionic liquid that a class has good characteristic, are again to produce other ion liquid key intermediates of the same type.
The preparation method of N, N-dialkylimidazolium halide ions liquid carries out usually in two steps: at first, with N-alkyl imidazole and halohydrocarbon is starting raw material, adopting acetone, toluene, acetonitrile, trichloromethane or excessive halohydrocarbon is solvent, finishes addition reaction in having the normal pressure reactor of reflux; After finishing, reaction carries out purification operations, make product N, the crystallization of N-dialkylimidazolium halogenide at low temperatures, separate with unreacted raw material and organic solvent, for improving purity, can in acetonitrile, ethyl acetate or trichloromethane equal solvent, carry out repeatedly the recrystallization operation, also can under reduced pressure, distill, to remove volatile solvent reaction product.This method need be used a large amount of volatile organic solvents, easily environment is polluted, and simultaneously, adopts excessive halohydrocarbon to cause waste to raw material.
Namboodiri and Verma have successively studied the synthetic N of the promoted non-solvent method of microwave technology, N-dialkylimidazolium halogenide and N, N-dialkylimidazolium tetrafluoro and have closed borate (Chem.Commun.2001,643-644; Tetrahedron Lett.2002,43,5381-5383).The microwave method reaction conditions is wayward, the thermal effect of microwave and electric field action easily cause reaction mass overheated and influence product quality, in addition, and for unreacted halohydrocarbon etc., still need adopt recrystallization or underpressure distillation to separate, can not avoid using volatile solvent fully.
Summary of the invention
At the deficiencies in the prior art and defective, the new preparation process that the purpose of this invention is to provide a kind of ion liquid in halogenated alkyl imidazole type, to overcome existing preparation method's process complexity, to use a large amount of volatile organic solvents, and the shortcoming that raw material halohydrocarbon utilization ratio is low, thereby provide a kind of efficient, eco-friendly ionic liquid preparation method.
Technical scheme of the present invention is as follows:
A kind of preparation method of ion liquid in halogenated alkyl imidazole type is characterized in that this method carries out as follows:
1) be raw material with N-alkyl imidazole and halohydrocarbon, raw materials used mol ratio is the N-alkyl imidazole: halohydrocarbon=1: 1~1: 1.1, under normal pressure, realize addition reaction in the closed reactor, and 40~150 ℃ of temperature of reaction, preferable reaction temperature are 40~80 ℃;
2) after the abundant reaction, in encloses container, feed CO
2, make reactor pressure be increased to subcritical range, utilize supercritical CO
2Continuous extraction reaction product isolated and unreacted raw material, temperature is 40~150 ℃ in the sepn process, preferred temperature is 40~80 ℃; Pressure 7.0~30.0MPa, preferred pressure is 7.0~15.0MPa;
3) by supercritical CO
2The isolating unreacted raw material of continuous extraction is collected in the separator of reactor downstream, and reactor is interior through supercritical CO
2Reaction product after the continuous extraction is ion liquid in halogenated alkyl imidazole type, and its chemical structural formula is:
Wherein, it is 4~8 alkyl that R, R ' represent carbonatoms respectively, comprises straight chained alkyl or branched-chain alkyl; X=Cl, Br, I.
Its feature of technology of the present invention also is: adopt supercritical CO
2Continuous extraction reaction product isolated and unreacted raw material, sepn process CO
2Flow 1.0~3.0L/min, continuous extraction 3~6 hours.
The preparation method of ion liquid in halogenated alkyl imidazole type provided by the invention, its key problem in technology is that employing N-alkyl imidazole and halohydrocarbon are raw material, halohydrocarbon need not excessive, finishes reaction in encloses container, after reaction finishes, utilizes supercritical CO
2Continuous extraction reaction product isolated and unreacted raw material.Its advantage is: 1. do not adopt excessive raw material halohydrocarbon, reduce the volatilization loss of halohydrocarbon and the environmental pollution that brings thus, improved the utilization ratio of halohydrocarbon.2. in the addition reaction process, do not adopt any organic solvent, eliminated the environmental problem that solvent may cause, simultaneously, reduced cost.3. in product separation and purification process, adopt supercritical CO
2Continuous extraction, simple to operate, unreacted raw material can all reclaim.Present method is a kind of efficient, and the ionic liquid preparation method of economic and complete environmental protection has realized not using any organic solvent, whole process environmental friendliness in ion liquid preparation process.
Embodiment
The preparation method of a kind of ion liquid in halogenated alkyl imidazole type provided by the present invention, be raw material N-alkyl imidazole and the halohydrocarbon that adopts approximate equimolar amount, under normal pressure, in closed reactor, finish the addition reaction of N-alkyl imidazole and halohydrocarbon, fully after the reaction, adopt supercritical CO
2Continuous extraction reaction product isolated and unreacted raw material.
Halohydrocarbon and the addition reaction of N-alkyl imidazole are shown below:
It is 4~8 alkyl that R, R ' represent carbonatoms respectively, comprises straight chained alkyl or branched-chain alkyl, X=Cl, Br, I.
Embodiment 1
But in the closed reactor of 200ml, add N-Methylimidazole 8.212g (0.100mol) successively, 1-chlorobutane 9.720g (0.105mol) was 40 ℃ of stirring reactions 24 hours.After reaction finishes, feed supercritical CO
2, under 40 ℃ of pressure 7.0MPa and temperature, CO
2Flow 1.0L/min, continuous extraction 4 hours separates obtaining product N, N-butyl methyl imidazoles villaumite 14.796g and unreacted reactant 3.136g (containing chlorobutane 1.875g and N-Methylimidazole 1.261g); The productive rate that calculates with chlorobutane is 80.7%.
Embodiment 2
But in the closed reactor of 200ml, add N-Methylimidazole 12.318g (0.150mol) successively, 1-chlorobutane 15.135g (0.163mol) was 80 ℃ of stirring reactions 12 hours.Reaction finishes, and feeds supercritical CO
2, under 80 ℃ of pressure 20.OMPa and temperature, CO
2Flow 1.0L/min, continuous extraction 4 hours separates obtaining product N, N-butyl methyl imidazoles villaumite 24.249g and unreacted reactant 3.204g (containing chlorobutane 2.285g and N-Methylimidazole 0.919g); Productive rate 84.9% with chlorobutane calculating.
Embodiment 3
But in the closed reactor of 200ml, add N-Methylimidazole 16.424g (0.200mol) successively, 1-chlorobutane 19.440g (0.210mol) was 150 ℃ of stirring reactions 8 hours.Reaction finishes, and feeds supercritical CO
2, under 150 ℃ of pressure 15.0MPa and temperature, CO
2Flow 1.0L/min, continuous extraction 3 hours separates obtaining product N, N-butyl methyl imidazoles villaumite 33.568g and unreacted reactant 2.296g (containing chlorobutane 1.652g and N-Methylimidazole 0.644g); Productive rate 91.5% with chlorobutane calculating.
Embodiment 4
But in the closed reactor of 200ml, add N-Methylimidazole 16.424g (0.200mol) successively, 1-n-butyl bromide 28.774g (0.210mol) was 120 ℃ of stirring reactions 6 hours.Reaction finishes, and feeds supercritical CO
2, under 120 ℃ of pressure 20.0MPa and temperature, CO
2Flow 1.0L/min, continuous extraction 6 hours separates obtaining product N, N-butyl methyl imidazoles bromine salt 39.445g and unreacted reactant 5.753g (containing n-butyl bromide 4.111g and N-Methylimidazole 1.642g); Productive rate 85.7% with n-butyl bromide calculating.
Embodiment 5
But in the closed reactor of 200ml, add N-Methylimidazole 16.424g (0.200mol) successively, hexyl bromide 1 bromohexane 34.665g (0.210mol) was 80 ℃ of stirring reactions 10 hours.Reaction finishes, and feeds supercritical CO
2, under 80 ℃ of pressure 30.0MPa and temperature, CO
2Flow 1.0L/min, continuous extraction 6 hours separates obtaining product N, N-hexyl methyl imidazoles bromine salt 42.022g and unreacted reactant 8.067g (containing bromohexane 5.603g and N-Methylimidazole 2.464g); Productive rate 83.8% with n-butyl bromide calculating.
Embodiment 6
But in the closed reactor of 200ml, add N-Methylimidazole 8.212g (0.100mol) successively, 1-bromooctane 21.243g (0.110mol) was 90 ℃ of stirring reactions 15 hours.Reaction finishes, and feeds supercritical CO
2, under 90 ℃ of pressure 25.0MPa and temperature.CO
2Flow 1.0L/min, continuous extraction 6 hours separates obtaining product N, N-octyl group Methylimidazole bromine salt 21.193g and unreacted reactant 8.262g (containing bromooctane 6.373g and N-Methylimidazole 1.889g); Productive rate 70.0% with bromooctane calculating.
Embodiment 7
But in the closed reactor of 200ml, add N-Methylimidazole 16.424g (0.200mol) successively, 1-butyl iodide 38.644g (0.210mol) was 100 ℃ of stirring reactions 10 hours.Reaction finishes, and feeds supercritical CO
2, under 100 ℃ of pressure 15.0MPa and temperature, CO
2Flow 1.0L/min, continuous extraction 6 hours separates obtaining product N, N-butyl methyl iodonium imidazolide salts 46.575g and unreacted reactant 8.493g (containing butyl iodide 6.440g and N-Methylimidazole 2.053g); Productive rate 83.3% with butyl iodide calculating.
Claims (4)
1. the preparation method of an ion liquid in halogenated alkyl imidazole type is characterized in that this method carries out as follows:
1) be raw material with N-alkyl imidazole and halohydrocarbon, raw materials used mol ratio is the N-alkyl imidazole: halohydrocarbon=1: 1~1: 1.1, under normal pressure, realize addition reaction in the closed reactor, 40~150 ℃ of temperature of reaction;
2) after the abundant reaction, in encloses container, feed CO
2, make reactor pressure be increased to subcritical range, utilize supercritical CO
2Continuous extraction reaction product isolated and unreacted raw material, temperature is 40~150 ℃ in the sepn process, pressure 7.0~30.0MPa;
3) by supercritical CO
2The isolating unreacted raw material of continuous extraction is collected in the separator of reactor downstream, and reactor is interior through supercritical CO
2Reaction product after the continuous extraction is ion liquid in halogenated alkyl imidazole type, and its chemical structural formula is:
Wherein, it is 4~8 alkyl that R, R ' represent carbonatoms respectively, comprises straight chained alkyl or branched-chain alkyl; X=Cl, Br, I.
2. preparation method according to claim 1 is characterized in that: the temperature range of finishing the addition reaction of N-alkyl imidazole and halohydrocarbon in the step 1) under normal pressure in the closed reactor is 40~80 ℃.
3. preparation method according to claim 1 is characterized in that: step 2) the middle supercritical CO that adopts
2Continuous extraction reaction product isolated and unreacted raw material, temperature is 40~80 ℃ in its sepn process, pressure 7.0~15.0MPa.
4. according to the described preparation method of the arbitrary claim of claim 1~3, it is characterized in that: adopt supercritical CO
2Continuous extraction reaction product isolated and unreacted raw material, sepn process CO
2Flow 1.0~3.0L/min, continuous extraction 3~6 hours.
Priority Applications (1)
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CNB2005100113778A CN1304376C (en) | 2005-03-04 | 2005-03-04 | Method for preparing ion liquid in halogenated alkyl imidazole type |
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CNB2005100113778A CN1304376C (en) | 2005-03-04 | 2005-03-04 | Method for preparing ion liquid in halogenated alkyl imidazole type |
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CN1696117A CN1696117A (en) | 2005-11-16 |
CN1304376C true CN1304376C (en) | 2007-03-14 |
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CN100369900C (en) * | 2006-01-24 | 2008-02-20 | 广东工业大学 | Process for preparing ionic liquid |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5371101A (en) * | 1992-04-28 | 1994-12-06 | Takeda Chemical Industries, Ltd. | Azole compounds, their production and use |
CN1521163A (en) * | 2003-01-27 | 2004-08-18 | 浙江工业大学 | Process for preparing room temperature ionic liquid |
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US5371101A (en) * | 1992-04-28 | 1994-12-06 | Takeda Chemical Industries, Ltd. | Azole compounds, their production and use |
CN1521163A (en) * | 2003-01-27 | 2004-08-18 | 浙江工业大学 | Process for preparing room temperature ionic liquid |
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