CN102206199A - Synthesis method for cyclic carbonate under catalysis of supported Bronsted acidic ionic liquid catalyst - Google Patents
Synthesis method for cyclic carbonate under catalysis of supported Bronsted acidic ionic liquid catalyst Download PDFInfo
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- CN102206199A CN102206199A CN2011100884028A CN201110088402A CN102206199A CN 102206199 A CN102206199 A CN 102206199A CN 2011100884028 A CN2011100884028 A CN 2011100884028A CN 201110088402 A CN201110088402 A CN 201110088402A CN 102206199 A CN102206199 A CN 102206199A
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Abstract
The invention provides a synthesis method for a cyclic carbonate under catalysis of a supported acidic ionic liquid catalyst, relates to a synthesis method for the cyclic carbonate, and mainly solves the technical problems that the catalyst is difficult to recover and the energy consumption is high during the separation process in the existing cyclic carbonate preparation methods. The method provided by the invention comprises the following steps of: adding the supported acidic ionic liquid catalyst to an autoclave, adding an epoxy compound, closing the autoclave, introducing carbon dioxide to the autoclave until the internal pressure of the autoclave is 0.5-5 MPa, heating to the reaction temperature of 80-200 DEG C, reacting while maintaining the pressure and temperature for 1.0-10 hours, cooling the autoclave to room temperature, slowly discharging carbon dioxide, filtering and distilling under reduced pressure to obtain the cyclic carbonate. The catalytic synthesis method has the advantages of mild reaction conditions, high catalyst activity, easy separation of the catalyst from a product, recyclable catalyst, etc.
Description
Technical field
The present invention relates to the synthetic method of cyclic carbonate; Be specifically related to pass through the cycloaddition reaction method for cyclic carbonates by carbonic acid gas and epoxy compounds.
Background technology
At present, as the CO of main greenhouse gas
2Quantity discharged just increase progressively with annual 4% speed, this has caused and has seriously influenced for Human's production, life.Simultaneously, CO
2Be again abundant, the most cheap C of reserves on the earth
1Resource.Under gentle relatively condition, realize CO
2Chemical fixation meet the requirement of Sustainable development, production process greenization, become one of hot issue of academic research and industrialization process.Utilize CO
2With the epoxide synthesizing annular carbonate be CO
2One of important channel of recycling, carbonic acid gas is carried out utilization as a kind of carbon oxygen resource in this reaction, is the Atom economy reaction, and its atom utilization reaches 100%.The cyclic carbonate that obtains of reaction is a kind of important industrial raw material, all is widely used in the synthesizing of electrolytic solution, polar solvent and the medicine of battery and fine chemicals.Since the structures shape of carbonic acid gas its have certain unreactiveness, so can the key that carry out smoothly of this reaction just be to activate the effective catalyst of carbonic acid gas.
At present, the catalyzer of having reported that is used for catalysis carbonic acid gas and epoxy compounds synthesizing annular carbonate has (X.Yin, J.R.Moss, Coord.Chem.Rev.1999,181,27 such as quaternary ammonium salt, transition metal complex, metal oxide, organic bases; R.L.Paddock, S.T.Nguyen, J.Am.Chem.Soc.2001,121,11498; Pasquale R.Angew.Chem.Int.Ed.2009,48,2946; W.L.Dai.Catal.Lett.2010,137,74; Y.Xie, K.Ding, Z.Liu.Chem.Eur.J.2010,16,6687), but under the effect of these catalyzer, mostly exist severe reaction conditions, needs to use problems such as solvent, product separation difficulty and catalyst recovery difficulty in the reaction process.
Summary of the invention
The present invention will solve existing preparation cyclic carbonate method and have catalyst recovery difficulty and the high technical problem of sepn process energy consumption; And provide immobilized
The method of acidic ionic liquid catalysts catalytically synthesizing cyclic carbonate ester.
Immobilized among the present invention
The method of synthesizing cyclic carbonate ester in presence of acidic ionic liquid catalyst is undertaken by following step: with immobilized
Acidic ionic liquid catalysts adds in the autoclave, and is described immobilized
Acidic ionic liquid catalysts is that carrier surface or duct internal burden have
The catalyzer of acidic ion liquid is pressed again
Acidic ion liquid and epoxy compounds mol ratio are that 1～8: 100 ratios add epoxy compounds in autoclave, airtight autoclave, feeding carbonic acid gas to the pressure in the autoclave is 0.5～5MPa, be warming up to temperature of reaction, temperature of reaction is 80～200 ℃, insulation constant voltage reaction 1.0～10 hours, then autoclave is cooled to room temperature, slowly emit carbonic acid gas, filtering the back underpressure distillation, promptly obtaining cyclic carbonate.
Reaction conditions gentleness of the present invention: not using any organic solvent in the catalytic process, is an eco-friendly catalytic process, and the present invention is that the pressure in autoclave is to carry out under 0.5～5MPa and 80～200 ℃ of temperature.The technology of the inventive method is simple, the reactive behavior height of catalyzer, and the yield of high cyclic carbonate that obtains is 92.7%.The inventive method is separated and catalyzer can be separated with product by simple filtering, thereby the catalyzer after separating can directly recycle and reduced production cost.Target product cyclic carbonate selectivity is up to more than 98%.The inventive method prepares advantages such as cyclic carbonate has efficiently, economy, environmental protection, has extraordinary prospects for commercial application.
Description of drawings
Fig. 1 is the mass spectroscopy spectrogram of the propylene carbonate that makes of embodiment 15; Fig. 2 is the mass spectroscopy spectrogram of 4-benzene-[1,3] dioxy ring penta-2-ketone of making of embodiment 34; Fig. 3 is the mass spectroscopy spectrogram of cyclohexyl [1,3] dioxy ring penta-2-ketone of making of embodiment 35.
Embodiment
Technical solution of the present invention is not limited to following cited embodiment, also comprises the arbitrary combination between each embodiment.
Embodiment one: immobilized in the present embodiment
The method of synthesizing cyclic carbonate ester in presence of acidic ionic liquid catalyst is undertaken by following step: with immobilized
Acidic ionic liquid catalysts adds in the autoclave, and is described immobilized
Acidic ionic liquid catalysts is that carrier surface or duct internal burden have
The catalyzer of acidic ion liquid is pressed again
Acidic ion liquid and epoxy compounds mol ratio are that 1～8: 100 ratios add epoxy compounds in autoclave, airtight autoclave, feeding carbonic acid gas to the pressure in the autoclave is 0.5～5MPa, intensification is warming up to temperature of reaction, and temperature of reaction is 80～200 ℃, insulation constant voltage reaction 1.0～10 hours, then autoclave is cooled to room temperature, slowly emit carbonic acid gas, filtering the back underpressure distillation, promptly obtaining cyclic carbonate.
The highest yield that present embodiment obtains cyclic carbonate is 92.7%, and selectivity is up to more than 98%.
Described immobilized
The preparation method of acidic ionic liquid catalysts is as follows: carrier, imidazoles are placed acetonitrile stirring and refluxing 24h, be cooled to room temperature then, filter, wash, vacuum-drying obtains the precursor of load imidazoles functional group to constant weight; Again this precursor and 2-bromo-butyric acid are placed toluene, stirring reaction 24h under 80 ℃ of conditions is cooled to room temperature with reaction system then, and filtration washing to filtrate is neutral, is put in and is dried to constant weight in the vacuum drying oven, obtains immobilized
Acidic ionic liquid catalysts.
Embodiment two: what present embodiment and embodiment one were different is: the chemical formula of described epoxy compounds is
R in the formula
1-be H-, R
2-be H-, CH
3-, ClCH
2-,
C
4H
9-, C
2H
3-or
Other step is identical with embodiment one with parameter.
Embodiment three: what present embodiment was different with embodiment one or two is: described immobilized
The acidic ionic liquid catalysts load
The chemical formula of acidic ion liquid is
Or
N=2 in the formula～6, m=1～3, X is Cl, Br, I or HSO
4Other step is identical with embodiment one or two with parameter.
Embodiment four: what present embodiment was different with one of embodiment one to three is: described immobilized
The carrier of acidic ionic liquid catalysts is polystyrene resin (chlorine ball), SiO
2, MCM-41, AlMCM-41 or SBA-15.Other step is identical with one of embodiment one to three with parameter.
Embodiment five: what present embodiment was different with one of embodiment one to four is: described immobilized
In the acidic ionic liquid catalysts
The charge capacity of acidic ion liquid is 0.1～10mmol/g.Other step is identical with one of embodiment one to four with parameter.
Embodiment six: what present embodiment was different with one of embodiment one to five is: press
Acidic ion liquid and epoxy compounds mol ratio are that 2～6: 100 ratios add epoxy compounds in autoclave.Other step is identical with one of embodiment one to five with parameter.
Embodiment seven: what present embodiment was different with one of embodiment one to five is: press
Acidic ion liquid and epoxy compounds mol ratio are that 3～5: 100 ratios add epoxy compounds in autoclave.Other step is identical with one of embodiment one to five with parameter.
Embodiment eight: what present embodiment was different with one of embodiment one to five is: press
Acidic ion liquid and epoxy compounds mol ratio are that 4: 100 ratios add epoxy compounds in autoclave.Other step is identical with one of embodiment one to five with parameter.
Embodiment nine: what present embodiment was different with one of embodiment one to eight is: described temperature of reaction is 80～200 ℃.Other step is identical with one of embodiment one to eight with parameter.
Embodiment ten: what present embodiment was different with one of embodiment one to eight is: described temperature of reaction is 100～130 ℃.Other step is identical with one of embodiment one to eight with parameter.
Embodiment 11: what present embodiment was different with one of embodiment one to eight is: described temperature of reaction is 120 ℃.Other step is identical with one of embodiment one to eight with parameter.
Embodiment 12: what present embodiment was different with one of embodiment one to 11 is: the pressure in the described autoclave is 0.5～5.0MPa.Other step is identical with one of embodiment one to 11 with parameter.
Embodiment 13: what present embodiment was different with one of embodiment one to 11 is: the pressure in the described autoclave is 1.0～2.5MPa.Other step is identical with one of embodiment one to 11 with parameter.
Embodiment 14: what present embodiment was different with one of embodiment one to 11 is: the pressure in the described autoclave is 1.0～2.5MPa.Other step is identical with one of embodiment one to 11 with parameter.
Embodiment 15: immobilized in the present embodiment
The method of synthesizing cyclic carbonate ester in presence of acidic ionic liquid catalyst is as follows: adding 0.5g is immobilized in the 70ml autoclave
Acidic ionic liquid catalysts, described immobilized
The acidic ionic liquid catalysts load
Acidic ion liquid is that 1-methyl-3-(2-carboxyl-ethyl) imidazoles bromine salt (PS-HBImBr) adds the 5ml epoxy compounds again, and is described immobilized
The carrier of acidic ionic liquid catalysts is a polystyrene resin, described epoxy compounds is a propylene oxide, airtight autoclave, and feeding carbonic acid gas to the pressure in the autoclave is 2.5MPa, be warming up to temperature of reaction, temperature of reaction is 120 ℃, and insulation constant voltage reaction 3 hours is cooled to room temperature with autoclave then, slowly emit carbonic acid gas then, underpressure distillation (removing unreacted propylene oxide), filtering separation catalyzer and product obtain the propylene carbonate (see figure 1).
The reaction equation of present embodiment is as follows:
Carry out qualitative analysis through 6890/5973 chromatograph mass spectrometer, the selectivity that generates propylene carbonate in the present embodiment is greater than 98%, yield 84.7%.
Present embodiment is described immobilized
The preparation method of acidic ionic liquid catalysts is as follows:
With chlorine ball (PS-Cl) (5g), imidazoles (1.77g) and acetonitrile (20ml) place in three mouthfuls of round-bottomed flasks of 100ml, stirring and refluxing is to reacting 24h.Be cooled to room temperature, filter, wash, vacuum-drying obtains the precursor PS-Im (6.2g) of load imidazoles functional group to constant weight.
PS-Im (6.2g) and 2-bromo-butyric acid (4.6g) are placed in the 100mL round-bottomed flask that fills 30mL toluene 80 ℃ of stirring reaction 24h.Reaction is cooled to room temperature with reaction system after finishing, and filtration washing to filtrate is neutral, is put in and is dried to constant weight in the vacuum drying oven, obtains supported ion liquid PS-HBImBr catalyzer (7.13g).
Embodiment 16: what present embodiment and embodiment 15 were different is: described solid-supported catalyst load
Acidic ion liquid is 1-methyl-3-(carboxyl methyl) imidazoles bromine salt.Other step is identical with embodiment 15 with parameter.
Carry out qualitative analysis through 6890/5973 chromatograph mass spectrometer, the selectivity that generates propylene carbonate in the present embodiment is greater than 98%, the yield 71.6% of product.
Embodiment 17: what present embodiment and embodiment 15 were different is: described solid-supported catalyst load
Acidic ion liquid is 1-methyl-3-(carboxyl methyl) imidazoles villaumite.Other step is identical with embodiment 15 with parameter.
Analyze through 6890/5973 chromatograph mass spectrometer, the selectivity that generates propylene carbonate in the present embodiment is greater than 98%, yield 67.5%.
Embodiment 18: what present embodiment and embodiment 15 were different is: described solid-supported catalyst load
Acidic ion liquid is 1-methyl-3-(carboxyl methyl) iodonium imidazolide salts.Other step is identical with embodiment 15 with parameter.
Carry out qualitative analysis through 6890/5973 chromatograph mass spectrometer, the selectivity that generates propylene carbonate in the present embodiment is greater than 98%, yield 66.5%.
Embodiment 19: what present embodiment and embodiment 15 were different is: described solid-supported catalyst load
Acidic ion liquid is 1-methyl-3-(4-sulfonic group-butyl) imidazole bisulfate.Other step is identical with embodiment 15 with parameter.
Analyze through 6890/5973 chromatograph mass spectrometer, the selectivity that generates propylene carbonate in the present embodiment is greater than 98%, yield 29.8%.
Embodiment 20: what present embodiment and embodiment 15 were different is: immobilized
The acidic ionic liquid catalysts consumption is 0.3g, obtains propylene carbonate.Other step is identical with embodiment 15 with parameter.
Analyze through 6890/5973 chromatograph mass spectrometer, the selectivity that generates propylene carbonate in the present embodiment is greater than 98%, yield 75.5%.
Embodiment 21: what present embodiment and embodiment 15 were different is: immobilized
The acidic ionic liquid catalysts consumption is 0.7g, obtains propylene carbonate.Other step is identical with embodiment 15 with parameter.
Analyze through 6890/5973 chromatograph mass spectrometer, the selectivity that generates propylene carbonate in the present embodiment is greater than 98%, yield 92.1%.
Embodiment 22: what present embodiment and embodiment 21 were different is: described immobilized
The carrier of acidic ionic liquid catalysts is SiO
2, obtain propylene carbonate.Other step is identical with embodiment 21 with parameter.
Analyze through 6890/5973 chromatograph mass spectrometer, the selectivity that generates propylene carbonate in the present embodiment is greater than 98%, yield 91.0%.
Embodiment 23: what present embodiment and embodiment 21 were different is: described immobilized
The carrier of acidic ionic liquid catalysts is MCM-41, obtains propylene carbonate.Other step is identical with embodiment 21 with parameter.
Analyze through 6890/5973 chromatograph mass spectrometer, the selectivity that generates propylene carbonate in the present embodiment is greater than 98%, yield 95.8%.
Embodiment 24: what present embodiment and embodiment 21 were different is: described immobilized
The carrier of acidic ionic liquid catalysts is AlMCM-41, obtains propylene carbonate.Other step is identical with embodiment 21 with parameter.
Analyze through 6890/5973 chromatograph mass spectrometer, the selectivity that generates propylene carbonate in the present embodiment is greater than 98%, yield 92.3%.
Embodiment 25: what present embodiment and embodiment 21 were different is: temperature of reaction is 80 ℃, obtains propylene carbonate.Other step is identical with embodiment 21 with parameter.
Analyze through 6890/5973 chromatograph mass spectrometer, the selectivity that generates propylene carbonate in the present embodiment is greater than 98%, yield 32.1%.
Embodiment 26: what present embodiment and embodiment 21 were different is: temperature of reaction is 100 ℃.Other step is identical with embodiment 21 with parameter.
Analyze through 6890/5973 chromatograph mass spectrometer, the selectivity that generates propylene carbonate in the present embodiment is greater than 98%, yield 69.2%.
Embodiment 27: what present embodiment and embodiment 21 were different is: temperature of reaction is 130 ℃.Other step is identical with embodiment 21 with parameter.
Analyze through 6890/5973 chromatograph mass spectrometer, the selectivity that generates propylene carbonate in the present embodiment is greater than 98%, yield 93.0%.
Embodiment 28: what present embodiment and embodiment 21 were different is: the pressure in the autoclave is 1.0MPa.Other step is identical with embodiment 21 with parameter.
Analyze through 6890/5973 chromatograph mass spectrometer, the selectivity that generates propylene carbonate in the present embodiment is greater than 98%, yield 65.5%.
Embodiment 29: what present embodiment and embodiment 21 were different is: the pressure in the autoclave is 1.5MPa.Other step is identical with embodiment 21 with parameter.
Analyze through 6890/5973 chromatograph mass spectrometer, the selectivity that generates propylene carbonate in the present embodiment is greater than 98%, yield 90.1%.
Embodiment 30: what present embodiment and embodiment 21 were different is: the pressure in the autoclave is 2.0MPa.Other step is identical with embodiment 21 with parameter.
Analyze through 6890/5973 chromatograph mass spectrometer, the selectivity that generates propylene carbonate in the present embodiment is greater than 98%, yield 92.7%.
The embodiment hentriaconta-: what present embodiment and embodiment 21 were different is: the reaction times is 1.5h.Other step is identical with embodiment 21 with parameter.
Carry out qualitative analysis through 6890/5973 chromatograph mass spectrometer, the selectivity that generates propylene carbonate in the present embodiment is greater than 98%, yield 81.1%.
Embodiment 32: what present embodiment and embodiment 21 were different is: the reaction times is 2.5h.Other step is identical with embodiment 21 with parameter.
Analyze through 6890/5973 chromatograph mass spectrometer, the selectivity that generates propylene carbonate in the present embodiment is greater than 98%, yield 90.2%.
Embodiment 33: what this enforcement and embodiment 21 were different is: described epoxy compounds is an epoxy chloropropane, obtains 4-chloromethyl-[1,3] dioxy ring penta-2-ketone at last.Other step is identical with embodiment 21 with parameter.
Analyze through 6890/5973 chromatograph mass spectrometer, generate the selectivity 98.2% of 4-chloromethyl-[1,3] dioxy ring penta-2-ketone in the present embodiment, yield is 94.2%.
The present embodiment reaction equation is
Embodiment 34: what present embodiment and embodiment 21 were different is: described epoxy compounds is a Styrene oxide 98min., obtains 4-benzene-[1,3] dioxy ring penta-2-ketone (see figure 2) at last.Other step is identical with embodiment 21 with parameter.
Analyze through 6890/5973 chromatograph mass spectrometer, generate the selectivity 94.2% of 4-benzene-[1,3] dioxy ring penta-2-ketone in the present embodiment, yield is 92.7%.
The present embodiment reaction equation is
Embodiment 35: what this enforcement and embodiment 21 were different is: described epoxy compounds is a cyclohexene oxide, obtains cyclohexyl [1,3] dioxy ring penta-2-ketone (see figure 3) at last.Other step is identical with embodiment 21 with parameter.
Analyze through 6890/5973 chromatograph mass spectrometer, generate the selectivity 96.8% of cyclohexyl [1,3] dioxy ring penta-2-ketone in the present embodiment, yield is 34.5%.
The present embodiment reaction equation is
Embodiment 36: what this enforcement and embodiment 21 were different is: described epoxy compounds is a phenoxy group methylene radical oxyethane, obtains 4-allyloxy methyl [1,3] dioxy ring penta-2-ketone at last.Other step is identical with embodiment 21 with parameter.
Analyze through 6890/5973 chromatograph mass spectrometer, 4-allyloxy methyl [1,3] the dioxy ring penta-2-ketone selectivity 98.9% that generates in the present embodiment, yield is 91.1%.
The present embodiment reaction equation is
Embodiment 37: what this enforcement and embodiment 21 were different is: described immobilized
Acidic ionic liquid catalysts is after reusing through four times.Other step is identical with embodiment 21 with parameter.
Analyze through 6890/5973 chromatograph mass spectrometer, the selectivity that generates propylene carbonate in the present embodiment is 98%, and yield is 91.2%.
Claims (10)
1. immobilized
The method of acidic ionic liquid catalysts catalytically synthesizing cyclic carbonate ester is characterized in that immobilized
The method of synthesizing cyclic carbonate ester in presence of acidic ionic liquid catalyst is undertaken by following step: with immobilized
Acidic ionic liquid catalysts adds in the autoclave, and is described immobilized
Acidic ionic liquid catalysts is that carrier surface or duct internal burden have
The catalyzer of acidic ion liquid is pressed again
Acidic ion liquid and epoxy compounds mol ratio are that 1～8: 100 ratios add epoxy compounds in autoclave, airtight autoclave, feeding carbonic acid gas to the pressure in the autoclave is 0.5～5MPa, be warming up to temperature of reaction, temperature of reaction is 80～200 ℃, insulation constant voltage reaction 1.0～10 hours, then autoclave is cooled to room temperature, slowly emit carbonic acid gas, filtering the back underpressure distillation, promptly obtaining cyclic carbonate.
2. according to claim 1 immobilized
The method of acidic ionic liquid catalysts catalytically synthesizing cyclic carbonate ester is characterized in that the chemical formula of described epoxy compounds is
R in the formula
1-be H-, R
2-be H-, CH
3-, ClCH
2-,
C
4H
9-, C
2H
3-or
3. according to claim 1 and 2 immobilized
The method of acidic ionic liquid catalysts catalytically synthesizing cyclic carbonate ester is characterized in that immobilized
The acidic ionic liquid catalysts load
The chemical formula of acidic ion liquid is
Or
N=2 in the formula～6, m=1～3, X is Cl, Br, I or HSO
4
4. according to claim 3 immobilized
The method of acidic ionic liquid catalysts catalytically synthesizing cyclic carbonate ester is characterized in that described immobilized
The carrier of acidic ionic liquid catalysts is SiO
2, MCM-41, AlMCM-41 or SBA-15.
5. according to claim 4 immobilized
The method of acidic ionic liquid catalysts catalytically synthesizing cyclic carbonate ester is characterized in that immobilized
In the acidic ionic liquid catalysts
The charge capacity of acidic ion liquid is 0.1～10mmol/g.
6. according to claim 5 immobilized
The method of acidic ionic liquid catalysts catalytically synthesizing cyclic carbonate ester, it is characterized in that by
Acidic ion liquid and epoxy compounds mol ratio are that 2～6: 100 ratios add epoxy compounds in autoclave.
7. according to claim 5 immobilized
The method of acidic ionic liquid catalysts catalytically synthesizing cyclic carbonate ester, it is characterized in that by
Acidic ion liquid and epoxy compounds mol ratio are that 4: 100 ratios add epoxy compounds in autoclave.
8. according to claim 6 immobilized
The method of acidic ionic liquid catalysts catalytically synthesizing cyclic carbonate ester is characterized in that 100～130 ℃ of described temperature of reaction.
9. according to claim 6 immobilized
The method of acidic ionic liquid catalysts catalytically synthesizing cyclic carbonate ester is characterized in that 120 ℃ of described temperature of reaction.
10. according to claim 8 immobilized
The method of acidic ionic liquid catalysts catalytically synthesizing cyclic carbonate ester is characterized in that the pressure in the described autoclave is 1.0～2.5MPa.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106831595A (en) * | 2017-01-19 | 2017-06-13 | 河南大学 | A kind of benzyl imidazole ionic liquid and the method using its catalytically synthesizing cyclic carbonate ester |
| CN109575162A (en) * | 2017-09-29 | 2019-04-05 | 中国石油化工股份有限公司 | Ion exchange resin and purposes |
| CN113185490A (en) * | 2021-04-15 | 2021-07-30 | 西北大学 | Carboxylic acid/metal halide composite catalytic CO2Method for preparing cyclic carbonate by cycloaddition with epoxide |
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| CN101318949A (en) * | 2008-07-23 | 2008-12-10 | 中国科学院过程工程研究所 | Process for synthesizing cyclic carbonate with catalysis of solid carried ion liquid catalyst |
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| CN101318949A (en) * | 2008-07-23 | 2008-12-10 | 中国科学院过程工程研究所 | Process for synthesizing cyclic carbonate with catalysis of solid carried ion liquid catalyst |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106831595A (en) * | 2017-01-19 | 2017-06-13 | 河南大学 | A kind of benzyl imidazole ionic liquid and the method using its catalytically synthesizing cyclic carbonate ester |
| CN106831595B (en) * | 2017-01-19 | 2019-04-05 | 河南大学 | A kind of benzyl imidazole ionic liquid and the method using its catalytically synthesizing cyclic carbonate ester |
| CN109575162A (en) * | 2017-09-29 | 2019-04-05 | 中国石油化工股份有限公司 | Ion exchange resin and purposes |
| CN109575162B (en) * | 2017-09-29 | 2021-03-30 | 中国石油化工股份有限公司 | Ion exchange resin and use |
| CN113185490A (en) * | 2021-04-15 | 2021-07-30 | 西北大学 | Carboxylic acid/metal halide composite catalytic CO2Method for preparing cyclic carbonate by cycloaddition with epoxide |
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Application publication date: 20111005 |