CN103242176B - Based on the functional ion liquid and preparation method thereof of choline chloride 60 - Google Patents

Based on the functional ion liquid and preparation method thereof of choline chloride 60 Download PDF

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CN103242176B
CN103242176B CN201310182178.8A CN201310182178A CN103242176B CN 103242176 B CN103242176 B CN 103242176B CN 201310182178 A CN201310182178 A CN 201310182178A CN 103242176 B CN103242176 B CN 103242176B
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应安国
李嵘嵘
杨健国
邱方利
王云龙
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Taizhou University
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    • 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
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    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract

The invention belongs to chemical material and preparing technical field thereof, disclose a kind of functional ion liquid based on choline chloride 60 and preparation method thereof, described ionic liquid has following structural formula I, wherein, and X --for methoxyl group negative ion, oxyethyl group negative ion, n-propyl alcohol negative ion, Virahol negative ion, trimethyl carbinol negative ion and propyl carbinol negative ion etc.This ion liquid dissolving is good, and can be used as a kind of catalyzer solvent of holding concurrently and be applied in organic synthesis, and preparation technology is simple, yield is high, purity is high.

Description

Based on the functional ion liquid and preparation method thereof of choline chloride 60
Technical field
The invention belongs to chemical material and preparing technical field, specifically, relate to a kind of functional ion liquid based on choline chloride 60 and preparation method thereof.
Background technology
As everyone knows, ionic liquid is made up of organic cation and inorganic or organic anion, is the salt of liquid state under room temperature or near room temperature.Ionic liquid has the advantages such as low volatility, low melting point, structure designability, broadening window, good conductivity and good solubility energy, makes it all be widely used in every field.In " ionic liquid-character, Synthesis and applications " book that Deng Youquan writes, describe the application of ionic liquid at all kinds of organic synthesis operating unit.Chinese patent CN101148392, CN1563008, CN1810757, CN1712093 etc. have set forth the application of ionic liquid in extracting and separating.Ionic liquid is successfully applied to field of nanometer technology by Chinese patent CN101177252, CN11600429, CN101177299 etc.Chinese patent CN101164122, CN101248495 etc. report the applicable cases that ionic liquid is prepared at electro-conductive material and conducting film.At present, ionic liquid can be divided into following a few class substantially: the pyridinium ion that the imidazol ion that alkyl replaces, alkyl replace, alkyl quaternary phosphine ion and alkyl quaternary ammonium ion.At present, the ionic liquid ubiquity of report preparation cost higher, there is the problems such as certain toxicity and non-biodegradable.
Prior art is compared, and the present invention has following unusual effect:
(1) the present invention prepare functional ion liquid adopt ion exchange reaction belong to neutralization reaction; technique is simple, and facility investment is few, need not nitrogen protection; gained ionic liquid product yield can up to 97%, purity up to 98%, can produce without any by product in reaction process.
(2) functional ion liquid of the present invention to common organic reagent and material dissolves good, and due to the existence of hydroxyl in positively charged ion, there is certain alkalescence and hydrogen bond donor feature, can be used as catalyzer solvent of holding concurrently and be applied in organic synthesis.Functional ion liquid of the present invention is particularly useful for catalysis Knoevenagel condensing aromatic aldehydes and active methylene compound reaction, benzopyran derivatives is prepared in catalysis, beta-amino ketones, ester, nitrile and amide derivatives are prepared in catalysis, and make product have higher yield and purity.
Summary of the invention
Choline chloride 60 (HOC 2h 4n (CH 3) 3 +cl -) wide material sources, price is very cheap and without any toxicity (document Greenchemistry, 2011,13,82-90), contriver explores the series function ionic liquid that preparation take choline chloride 60 as raw material.
The object of the invention is to provide a kind of functional ion liquid formed for positively charged ion with the positive ion in choline chloride 60, and provides the preparation method of this kind of ionic liquid.Ionic liquid of the present invention is cheap, low toxicity is even nontoxic, and the catalyzer or the solvent that can be used as a kind of green are widely used in organic synthesis.
The object of the invention is to realize in the following manner:
Based on a functional ion liquid for choline chloride 60, this functional ion liquid has following structural formula I:
Wherein, X --for CH 3o -, CH 3cH 2o -, CH 3cH 2cH 2o -, CH 3(CH 3) CHO -, (CH 3) 3cO -, CH 3cH 2cH 2cH 2o -, CH 3cH 2cH 2cH 2cH 2o -, CH 3cH 2cH 2cH 2cH 2cH 2o -, CH 3cH 2cH 2cH 2cH 2cH 2cH 2o -, CH 3cH 2cH 2cH 2cH 2cH 2cH 2cH 2o -, or CH 3cH 2cH 2cH 2cH 2cH 2cH 2cH 2cH 2o -.
Preferred X --for methoxyl group negative ion, oxyethyl group negative ion, n-propyl alcohol negative ion, Virahol negative ion, trimethyl carbinol negative ion or propyl carbinol negative ion.
Described functional ion liquid is preferably:
The preparation method of above-mentioned functions ionic liquid comprises the following steps: the metal-salt MX of choline chloride 60 and equimolar amount carries out ion exchange reaction at temperature is 60 ~ 215 DEG C, and obtain functional ion liquid, its reaction equation is as follows:
Wherein, M is Na +, or K +; X is CH 3o -, CH 3cH 2o -, CH 3cH 2cH 2o -, CH 3(CH 3) CHO -, (CH 3) 3cO -, CH 3cH 2cH 2cH 2o -, CH 3cH 2cH 2cH 2cH 2o -, CH 3cH 2cH 2cH 2cH 2cH 2o -, CH 3cH 2cH 2cH 2cH 2cH 2cH 2o -, CH 3cH 2cH 2cH 2cH 2cH 2cH 2cH 2o -, or CH 3cH 2cH 2cH 2cH 2cH 2cH 2cH 2cH 2o -.
X is preferably methoxyl group negative ion, oxyethyl group negative ion, n-propyl alcohol negative ion, Virahol negative ion, trimethyl carbinol negative ion or propyl carbinol negative ion.
The solvent that above-mentioned ion exchange reaction adopts is methyl alcohol, ethanol, n-propyl alcohol, Virahol, the trimethyl carbinol or propyl carbinol.
Above-mentioned preparation method's preferable reaction temperature is 60-100 DEG C, and most preferably temperature of reaction is 64.5-97.1 DEG C.Reaction times can be 12 ~ 24 hours.React complete, can vacuum-drying 5 ~ 10 hours under 60 ~ 80 DEG C of conditions, obtain light yellow transparent liquid, be in a liquid state under room temperature, its structural formula is as follows:
The particularly reactant of the present invention's employing
CH 3cH 2cH 2cH 2cH 2cH 2cH 2oNa, CH 3cH 2cH 2cH 2cH 2cH 2cH 2cH 2oNa, CH 3cH 2cH 2cH 2cH 2cH 2cH 2cH 2cH 2oNa, CH 3cH 2cH 2cH 2cH 2cH 2cH 2oK, CH 3cH 2cH 2cH 2cH 2cH 2cH 2cH 2oK, CH 3cH 2cH 2cH 2cH 2cH 2cH 2cH 2cH 2oK, structure is comparatively large, and the sterically hindered of reaction position microcosmic is seen and is difficult to reaction, but overcome above-mentioned difficulties in preparation process of the present invention comparatively greatly, still obtains the higher ionic liquid of catalytic performance.
The ionic liquid of preparation can be used 1hNMR, 13cNMR structural confirmation.
Embodiment
Below with reference to embodiment, the present invention will be further described, and embodiments of the invention are only for illustration of technical scheme of the present invention, and non-limiting the present invention.
Embodiment 1
Experimental installation is there-necked flask mainly, in order to stir fully, adopts mechanical stirring.Flask is placed in by the choline chloride 60 of precise with containing the methanol solution of sodium methylate (with choline chloride 60 etc. mole), flask is placed in oil bath, under high-speed stirring, 64.5 DEG C are reacted 12 hours, cooling, filtration, filtrate washed with diethylether, then underpressure distillation is except desolventizing, and gained liquid vacuum 60 DEG C of dryings 5 hours, obtain light yellow transparent liquid, yield 97%, purity is 98%.The ionic liquid prepared: 1hNMR (400M, D 2o): δ 4.05 (m, 2H), 3.49 (t, 2H, J=5.2Hz), 3.36 (s, 3H), 3.20 (s, 9H); 13cNMR (100M, D 2o): δ 67.86,55.73,53.91,53.84,48.92.
Reaction formula is:
Embodiment 2
Experimental installation is there-necked flask mainly, in order to stir fully, adopts mechanical stirring.Flask is placed in by the choline chloride 60 of precise with containing the ethanolic soln of sodium ethylate (with choline chloride 60 etc. mole), flask is placed in oil bath, under high-speed stirring, 78.4 DEG C are reacted 12 hours, cold filtration, filtrate washed with diethylether, then underpressure distillation is except desolventizing, and gained liquid vacuum 70 DEG C of dryings 5 hours, obtain light yellow transparent liquid, yield 93%, purity is 96%.The ionic liquid prepared: 1hNMR (400M, D 2o): δ 3.98 (m, 2H), 3.44 (t, 2H, J=4.8Hz), 3.13 (s, 9H), 2.42 (q, 2H, J=7.2Hz), 1.82 (t, 3H, J=7.2Hz); 13cNMR (100M, D 2o): δ 67.42,55.57,53.84,35.6,23.46.
Reaction formula is:
Embodiment 3
Experimental installation is there-necked flask mainly, in order to stir fully, adopts mechanical stirring.Flask is placed in by the choline chloride 60 of precise with containing the n-propyl alcohol solution of n-propyl alcohol sodium (with choline chloride 60 etc. mole), flask is placed in oil bath, under high-speed stirring, 97.1 DEG C are reacted 12 hours, cold filtration, filtrate washed with diethylether, then underpressure distillation is except desolventizing, and gained liquid vacuum 80 DEG C of dryings 5 hours, obtain light yellow transparent liquid, yield 96%, purity is 98%.The ionic liquid prepared: 1hNMR (400M, D 2o): δ 4.03 (m, 2H), 3.48 (t, 2H, J=5.2Hz), 3.16 (s, 9H), 2.26 (t, 2H, J=7.2Hz), 1.82 (m, 2H), 0.86 (t, 3H, J=7.2Hz); 13cNMR (100M, D 2o): δ 67.49,55.68,54.02,53.97 .53.94,39.73,25.8,13.46.
Reaction formula is:
Embodiment 4
Experimental installation is there-necked flask mainly, in order to stir fully, adopts mechanical stirring.Flask is placed in by the choline chloride 60 of precise with containing the t-butanol solution of potassium tert.-butoxide (with choline chloride 60 etc. mole), flask is placed in oil bath, under high-speed stirring, 82.4 DEG C are reacted 24 hours, cold filtration, filtrate washed with diethylether, then underpressure distillation is except desolventizing, and gained liquid vacuum 60 DEG C of dryings 10 hours, obtain light yellow transparent liquid, yield 92%, purity is 97%.The ionic liquid prepared: 1hNMR (400M, D 2o): δ 4.02 (m, 2H), 3.48 (t, 2H, J=4.8Hz), 3.16 (s, 9H), 1.09 (s, 9H); 13cNMR (100M, D 2o): δ 70.42,58.61,56.83,14.82.
Reaction formula is:
Embodiment 5
Experimental installation is there-necked flask mainly, in order to stir fully, adopts mechanical stirring.Flask is placed in by the choline chloride 60 of precise with containing the enanthol solution of enanthol potassium (with choline chloride 60 etc. mole), flask is placed in oil bath, under high-speed stirring, 176 DEG C are reacted 24 hours, cold filtration, filtrate washed with diethylether, then underpressure distillation is except desolventizing, and gained liquid vacuum 80 DEG C of dryings 5 hours, obtain light yellow transparent liquid, yield 86%, purity is 95%.The ionic liquid prepared: 1hNMR (400M, D 2o): δ 3.95 (m, 2H), 3.46 (t, 2H, J=7.2Hz), 3.15 (s, 9H), 2.24 (t, 2H, J=7.2Hz), 1.96-1.71 (m, 10H), 0.88 (t, 3H, J=7.2Hz); 13cNMR (100M, D 2o): δ 67.52,56.01,53.85,54.05 .53.88,40.62,31.68,29.82,28.52,27.63,26.32,13.23.
Reaction formula is:
Embodiment 6
Experimental installation is there-necked flask mainly, in order to stir fully, adopts mechanical stirring.Flask is placed in by the choline chloride 60 of precise with containing the octanol solution of octanol potassium (with choline chloride 60 etc. mole), flask is placed in oil bath, under high-speed stirring, 184 DEG C are reacted 24 hours, cold filtration, filtrate washed with diethylether, then underpressure distillation is except desolventizing, and gained liquid vacuum 80 DEG C of dryings 5 hours, obtain light yellow transparent liquid, yield 83%, purity is 96%.The ionic liquid prepared: 1hNMR (400M, D 2o): δ 4.02 (m, 2H), 3.48 (t, 2H, J=4.8Hz), 3.18 (s, 9H), 2.31 (t, 2H, J=7.2Hz), 1.89-1.73 (m, 12H), 0.83 (t, 3H, J=7.2Hz); 13cNMR (100M, D 2o): δ 67.58,56.03,53.89,54.55 .54.03,40.68,31.75,30.06,29.38,28.63,27.63,26.33,13.35.
Reaction formula is:
Embodiment 7
Experimental installation is there-necked flask mainly, in order to stir fully, adopts mechanical stirring.Flask is placed in by the choline chloride 60 of precise with containing the nonyl alcohol solution of nonyl alcohol potassium (with choline chloride 60 etc. mole), flask is placed in oil bath, under high-speed stirring, 215 DEG C are reacted 24 hours, cold filtration, filtrate washed with diethylether, then underpressure distillation is except desolventizing, and gained liquid vacuum 80 DEG C of dryings 5 hours, obtain light yellow transparent liquid, yield 85%, purity is 96%.The ionic liquid prepared: 1hNMR (400M, D 2o): δ 4.05 (m, 2H), 3.50 (t, 2H, J=4.8Hz), 3.15 (s, 9H), 2.35 (t, 2H, J=7.2Hz), 1.92-1.68 (m, 14H), 0.91 (t, 3H, J=7.2Hz); 13cNMR (100M, D 2o): δ 67.51,56.11,53.85,55.12,54.03,41.05,31.68,30.73,29.78,29.14,28.65,27.22,26.39,14.08.
Reaction formula is:
Embodiment 8
Phenyl aldehyde (5mmol), propane dinitrile (6mmol), Ketene dimethyl (6mmol), 5mL water, 0.25mmol are joined in 50mL single port bottle according to the ionic liquid that embodiment 7 method prepares, 80 DEG C are stirred 2 hours TLC and detect, raw material disappears, filter, Vacuum dry filter cake obtains product, yield: 90%, content 98%.Structure of title compound confirms: 1hNMR (400MHz, DMSO-d 6) (ppm): 7.29-7.10 (m, 5H), 7.03 (br, s; 2H), 4.15 (s, 1H), 2.51 (br; s, 3H), 2.25 (d; 1H, J=16Hz), 2.08 (d; 1H, J=16Hz), 1.05 (s; 3H), 0.96 (s, 3H); 13cNMR (100MHz, DMSO-d 6) (ppm): 196.3,163.2,159.3,145.6,128.9,127.9,127.2,121.1,113.4,60.1,50.8.
Embodiment 9
Morpholine (5mmol), methyl acrylate (5.5mmol), 1mmol are joined in 50mL single port bottle according to the ionic liquid that embodiment 7 method prepares successively, stirring at room temperature 2 hours, TLC detects, raw material disappears, use extracted with diethyl ether reaction solution, merge organic phase, column chromatography for separation obtains product, yield 88%, content 96%.Structure of title compound confirms: 1hNMR (400MHz, CDCl 3) (ppm): 3.66 (s, 3H, OCH 3), 3.67-3.65 (m, 4H, morpholinyl), 2.65 (t, 2H, J=6Hz, CH 2), 2.48 (t, 2H, J=6Hz, CH 2), 2.43-2.41 (m, 4H, morpholinyl); 13cNMR (100MHz, CDCl 3) (ppm): 172.8,66.8,53.8,53.3,51.6,31.7.
Embodiment 10
Phenyl aldehyde (5mmol), propane dinitrile (6mmol), 4mL water, 0.25mmol are joined in 50mL single port bottle according to the ionic liquid that embodiment 7 method prepares successively, stirring at room temperature 10 minutes TLC detect, raw material disappears, filter, Vacuum dry filter cake obtains product, yield 96%, content 98%.Structure of title compound confirms: 1hNMR (400MHz, CDCl 3) (ppm): 7.91 (d, 2H, J=7.6Hz, ArH), 7.79 (s, 1H, C=CH); 7.64 (t, 1H, J=7.6Hz, ArH), 7.27 (t, 2H; J=7.6Hz, ArH), 7.27 (t, 2H, J=7.6Hz, ArH); 13cNMR (100MHz, CDCl 3) (ppm): 160.0,134.6,130.9,130.7,129.6,113.7,112.5,82.7.
Embodiment 11
Phenyl aldehyde (5mmol), propane dinitrile (6mmol), Ketene dimethyl (6mmol), 5mL water, 0.25mmol are joined in 50mL single port bottle according to the ionic liquid that embodiment 6 method prepares, 80 DEG C are stirred 2 hours TLC and detect, raw material disappears, filter, Vacuum dry filter cake obtains product, yield: 88%, content 96%.Structure of title compound NMR is with embodiment 8.
Embodiment 12
Morpholine (5mmol), methyl acrylate (5.5mmol), 1mmol are joined in 50mL single port bottle according to the ionic liquid that embodiment 6 method prepares successively, stirring at room temperature 1.5 hours, TLC detects, raw material disappears, use extracted with diethyl ether reaction solution, merge organic phase, column chromatography for separation obtains product, yield 90%, content 98%.Products obtained therefrom NMR structure is with embodiment 9.
Embodiment 13
Phenyl aldehyde (5mmol), propane dinitrile (6mmol), 4mL water, 0.25mmol are joined in 50mL single port bottle according to the ionic liquid that embodiment 6 method prepares successively, stirring at room temperature 10 minutes TLC detect, raw material disappears, filter, Vacuum dry filter cake obtains product, yield 93%, content 99%.Products obtained therefrom NMR structure is with embodiment 10.
Embodiment 14
Phenyl aldehyde (5mmol), propane dinitrile (6mmol), Ketene dimethyl (6mmol), 5mL water, 0.25mmol are joined in 50mL single port bottle according to the ionic liquid that embodiment 5 method prepares, 80 DEG C are stirred 1.5 hours TLC and detect, raw material disappears, filter, Vacuum dry filter cake obtains product, yield: 93%, content 98%.Products obtained therefrom NMR structure is with embodiment 8.
Embodiment 15
Morpholine (5mmol), methyl acrylate (5.5mmol), 1mmol are joined in 50mL single port bottle according to the ionic liquid that embodiment 5 method prepares successively, stirring at room temperature 1 hour, TLC detects, raw material disappears, use extracted with diethyl ether reaction solution, merge organic phase, column chromatography for separation obtains product, yield 95%, content 98%.Products obtained therefrom NMR structure is with embodiment 9.
Embodiment 16
Phenyl aldehyde (5mmol), propane dinitrile (6mmol), 4mL water, 0.25mmol are joined in 50mL single port bottle according to the ionic liquid that embodiment 5 method prepares successively, stirring at room temperature 10 minutes TLC detect, raw material disappears, filter, Vacuum dry filter cake obtains product, yield 96%, content 98%.Products obtained therefrom NMR structure is with embodiment 10.

Claims (9)

1. based on a functional ion liquid for choline chloride 60, it is characterized in that, described functional ion liquid has following structural formula I:
Wherein, X -for CH 3o -, CH 3cH 2o -, CH 3cH 2cH 2o -, CH 3(CH 3) CHO -, (CH 3) 3cO -, CH 3cH 2cH 2cH 2o -, CH 3cH 2cH 2cH 2cH 2o -, CH 3cH 2cH 2cH 2cH 2cH 2o -, CH 3cH 2cH 2cH 2cH 2cH 2cH 2o -, CH 3cH 2cH 2cH 2cH 2cH 2cH 2cH 2o -or CH 3cH 2cH 2cH 2cH 2cH 2cH 2cH 2cH 2o -.
2. functional ion liquid as claimed in claim 1, is characterized in that, described X -for methoxyl group negative ion, oxyethyl group negative ion, n-propyl alcohol negative ion, Virahol negative ion, trimethyl carbinol negative ion or propyl carbinol negative ion.
3. functional ion liquid as claimed in claim 1, it is characterized in that, described functional ion liquid is
4. the preparation method of a functional ion liquid according to claim 1, it is characterized in that the method comprises the following steps: the metal-salt MX of choline chloride 60 and equimolar amount carries out ion exchange reaction at temperature is 60 ~ 215 DEG C, obtain functional ion liquid, its reaction equation is as follows:
Wherein, M is Na +, or K +; X is CH 3o -, CH 3cH 2o -, CH 3cH 2cH 2o -, CH 3(CH 3) CHO -, (CH 3) 3cO -, CH 3cH 2cH 2cH 2o -, CH 3cH 2cH 2cH 2cH 2o -, CH 3cH 2cH 2cH 2cH 2cH 2o -, CH 3cH 2cH 2cH 2cH 2cH 2cH 2o -, CH 3cH 2cH 2cH 2cH 2cH 2cH 2cH 2o -or CH 3cH 2cH 2cH 2cH 2cH 2cH 2cH 2cH 2o -.
5. preparation method as claimed in claim 4, it is characterized in that, described X is methoxyl group negative ion, oxyethyl group negative ion, n-propyl alcohol negative ion, Virahol negative ion, trimethyl carbinol negative ion or propyl carbinol negative ion.
6. preparation method as claimed in claim 4, it is characterized in that, described temperature of reaction is 60-100 DEG C, and the reaction times is 12-24 hour.
7. preparation method as claimed in claim 4, is characterized in that, the solvent that described ion exchange reaction adopts is methyl alcohol, ethanol, n-propyl alcohol, Virahol, the trimethyl carbinol or propyl carbinol.
8. preparation method as claimed in claim 7, is characterized in that, after ion exchange reaction completes, cooling, filtration, after filtrate washed with diethylether, underpressure distillation is except desolventizing.
9. the preparation method as described in claim 4 or 7, is characterized in that, by the vacuum-drying 5 ~ 10 hours under 60 ~ 80 DEG C of conditions of gained liquid.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1651089A (en) * 2004-12-06 2005-08-10 河北师范大学 Non-toxic ionic liquid, preparation method and its application
CN101260051A (en) * 2008-04-24 2008-09-10 中国科学院过程工程研究所 Biodegradable choline-like ionic liquid
CN102321466A (en) * 2011-06-08 2012-01-18 浙江大学 Reversible thermochromic solution system based on ionic liquid solvent and application thereof
CN102533907A (en) * 2012-01-10 2012-07-04 华南理工大学 Method for increasing enzymolysis efficiency of rice straws through choline and amino acid ionic liquid pretreatment

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US20070129568A1 (en) * 2005-12-06 2007-06-07 Ngimat, Co. Ionic liquids
WO2007138307A2 (en) * 2006-05-25 2007-12-06 The Queen's University Of Belfast Process for removing sulfur-containing acids from crude oil

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1651089A (en) * 2004-12-06 2005-08-10 河北师范大学 Non-toxic ionic liquid, preparation method and its application
CN101260051A (en) * 2008-04-24 2008-09-10 中国科学院过程工程研究所 Biodegradable choline-like ionic liquid
CN102321466A (en) * 2011-06-08 2012-01-18 浙江大学 Reversible thermochromic solution system based on ionic liquid solvent and application thereof
CN102533907A (en) * 2012-01-10 2012-07-04 华南理工大学 Method for increasing enzymolysis efficiency of rice straws through choline and amino acid ionic liquid pretreatment

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