CN109134420A - A kind of preparation method of cyclic carbonate ester - Google Patents
A kind of preparation method of cyclic carbonate ester Download PDFInfo
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- CN109134420A CN109134420A CN201811087291.7A CN201811087291A CN109134420A CN 109134420 A CN109134420 A CN 109134420A CN 201811087291 A CN201811087291 A CN 201811087291A CN 109134420 A CN109134420 A CN 109134420A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
Abstract
The present invention provides a kind of preparation method of cyclic carbonate ester, the preparation method includes the following steps: the synthesis using catalyst cyclic carbonate ester, and the catalyst is aminoacrylic acid class ion liquid polymer heterogeneous catalyst；Cyclic carbonate ester selectivity with higher and conversion ratio are prepared using the above method, the purity of obtained cyclic carbonate ester product is up to 99.9mol%, compared to traditional method for preparing cyclic carbonate ester, the active site of ion liquid polymer catalyst used in the present invention is more, high catalytic efficiency, stabilization is not easily decomposed, preparation process is simple, additive amount is few, is easy many advantages, such as separating from liquid phase, industrial application value with higher.
Description
Technical field
The invention belongs to green catalysis field more particularly to a kind of preparation methods of cyclic carbonate ester.
Background technique
Carbon dioxide is as one of greenhouse gases, and efficiently trapping and conversion are the research centers of gravity of current numerous scholars
One of, it is a variety of high attached that carbon dioxide can obtain cyclic carbonate ester, dimethyl carbonate or isocyanates etc. by a variety of synthesizing means
Value added compound, wherein a kind of high bp polar solvent of the cyclic carbonate ester as aprotic that purposes is very extensive both may be used
It to serve as the electrolyte in lithium ion battery, and can be used for the synthesis of medicine and fine chemical product intermediate, therefore pass through green
Chemical means utilize carbon dioxide as Material synthesis cyclic carbonate ester, belong to current chemical industry technology in the urgent need to address
Problem.
Since carbon dioxide gas reactivity is poor, made at present using carbon dioxide gas as raw material in chemical industry
Standby cyclic carbonate ester mainly passes through the reaction condition existing for high temperature and pressure and catalyst by carbon dioxide gas and epoxy group
Lower progress, catalyst is particularly significant for the reaction of synthesizing cyclic carbonate ester, at present it has been reported that synthesizing cyclic carbonate ester urge
Agent can be divided into homogeneous catalyst and two class of heterogeneous catalysis, and homogeneous catalyst is primarily referred to as lewis acid and halide ion group
At homogeneous catalysis system, including quaternary ammonium salt, quaternary phosphonium salt, glyoxaline ion liquid, Lewis Acid metal complex etc., such as
A kind of method for preparing cyclic carbonate ester using succinimide and halide united catalyst is disclosed in CN108299375A, benefit
With the synergistic effect of succinimide and halide, reaction temperature is 25~90 DEG C, and reaction pressure is 0.1~1MPa, reaction
Time is 1~10h, and obtained cyclic carbonate ester yield can reach 90% or more, however, the usual dosage of above-mentioned homogeneous catalyst
It is larger, there is separation difficulty in aftertreatment technology after completion of the reaction, needed during the separation process using environmentally harmful molten
Agent is difficult to the problem of being suitable for the urgent need to resolve such as industrialization successive reaction, therefore application prospect is little.
Heterogeneous catalysis due to its be insoluble in reaction system, be easily isolated, be easy to be arranged in the reactor etc. it is excellent
Point, belongs to the research hotspot in cyclic carbonate ester synthesis field at present, and the heterogeneous catalysis developed so far includes that quaternary phosphonium salt is negative
Carrier series catalysts, alkali metal salt loaded catalyst and base-modified ion-exchange resin catalyst etc., use load type gold
The heterogeneous catalysis such as metal catalyst and support type quaternary ammonium salt catalyst can be able to solve catalyst to a certain extent and return
The problems such as difficult is received, however, activity is usually lower in the reaction, it is larger usually to there is dosage, synthesizes for above-mentioned heterogeneous catalysis
Complicated, the problems such as service life is shorter, to cause its use cost high, for example, disclosing in CN101318949A
A method of using catalysis of solid carried ion liquid catalyst synthesizing cyclic carbonate ester, wherein mesopore molecular sieve is utilized as load
Body has imidazole salt ionic liquid in its area load, although obtained catalyst can urge under lower temperature and pressure
It is combined to cyclic carbonate ester, but its catalytic efficiency is lower, service life is shorter, and a kind of utilize is disclosed in CN103030623A and is loaded
The composite catalyst being made of the silica supports and grafting of metal silicate the silica supports of alkyl silicate, will
It is used for catalytic epoxyethane and catalytic efficiency is higher when carbon dioxide reaction prepares cyclic carbonate ester and additional amount is less, however its
The carrier loaded ability used is limited, and the service life of obtained catalyst is still shorter.
In recent years, ion liquid polymer because its have without carrier, will not decompose, long service life, active site it is more
And there is structure there can be biggish work by the extensive concern of researcher by many advantages such as different base group modifications or modifications
The potentiality used for cyclic carbonate ester synthetic catalyst.On the basis of existing technology, those skilled in the art needs further
It attempts to utilize ion liquid polymer, especially with aminoacrylic acid class ion liquid polymer, by conduct after its functionalization
A kind of heterogeneous cyclic carbonate ester synthetic catalyst uses, make it have can under conditions of solvent-free, high temperature, high pressure efficient catalytic
Synthesizing annular carbonate improves its service life, it was demonstrated that potentiality of the heterogeneous catalysis in cyclic carbonate ester industrialized production.
Summary of the invention
It can be in solvent-free, high temperature, high pressure in view of the deficiencies of the prior art, the present invention intends to provide one kind
Under conditions of efficient catalytic synthesizing annular carbonate method, it was demonstrated that heterogeneous catalysis is in cyclic carbonate ester industrialized production
Potentiality.
For this purpose, one of the objects of the present invention is to provide a kind of preparation method of cyclic carbonate ester, the preparation side
Method includes the following steps:
Use the synthesis of catalyst cyclic carbonate ester.
It include ion liquid polymer in the catalyst.
The ion liquid polymer has the structure as shown in formula one:
Wherein, m and n is each independently selected from random natural number, and m+n >=4, for example, 5,8,12,20,40,60,100,
120,150,180,200,250 or 300 etc..
R1And R2It is each independently selected from hydrogen atom or any one alkane group, for example, hydrogen atom, methyl, ethyl, third
Base, isopropyl, butyl or isobutyl group etc..
R3~R6It is each independently selected from any one alkane group, for example, methyl, ethyl, propyl, isopropyl, butyl
Or isobutyl group etc..
A1And A2It is each independently selected from any one alkylene hydrocarbyl group, for example, methylene, ethylidene, propylidene or Asia
Butyl etc..
X1And X2It is each independently selected from any one compatibility anion.
B1And B2It is each independently selected from the alkane of any one alkane group, hydroxy-end capped alkane group, carboxy blocking
The alkane group of group or sulfonate radical sealing end.
Present invention utilizes ion liquid polymers as catalyst synthesizing cyclic carbonate ester, and ionic liquid richness is utilized
Characteristic containing ion is conducive to stablize reaction intermediate, reduces reaction activity, meanwhile, the characteristics of polymer, makes ionic liquid
Body can be used as heterogeneous catalysis, be conducive to the separation of catalyst and reduced the generation of side reaction, further increase ring
The conversion ratio of carbonic acid ester synthesis reaction.
Preferably, the preparation method includes the following steps:
Addition reaction occurs under the catalysis of catalyst for carbon dioxide and the compound containing epoxy group, obtains ring carbon acid
Ester.
Preferably, the reaction temperature of the addition reaction be 80~150 DEG C, for example, 85 DEG C, 90 DEG C, 95 DEG C, 100 DEG C,
105 DEG C, 115 DEG C, 125 DEG C, 135 DEG C or 145 DEG C etc..
Preferably, the reaction pressure of the addition reaction be 1~5MPa, for example, 1.5MPa, 1.8MPa, 2.0MPa,
2.5MPa, 3.2MPa, 3.5MPa, 4.0MPa or 4.5MPa etc..
Preferably, the reaction time of the addition reaction be 1~8h, for example, 1.5h, 2h, 2.5h, 3h, 3.5h, 4h,
4.5h, 5h, 5.5h, 6h, 6.5h, 7h, 7.5h etc..
Preferably, the partial size of the catalyst be 10~100mm, for example, 12mm, 15mm, 20mm, 30mm, 40mm,
50mm, 60mm, 70mm, 80mm, 90mm or 95mm etc., suitable catalyst particle size may advantageously facilitate the absorption of carbon dioxide, into
And improve titanium dioxide charcoal percent conversion.
Preferably, the catalyst and the mass ratio of the epoxy group in the compound containing epoxy group are 1:2~200,
For example, 1:3,1:5,1:10,1:20,1:30,1:50,1:70,1:90,1:110,1:130,1:150,1:170 or 1:190 etc..
Preferably, the compound containing epoxy group be ethylene oxide, propylene oxide, epoxy butane, epoxychloropropane,
Styrene oxide, 7-oxa-bicyclo[4.1.0 or oxidation pentamethylene in any one or at least two mixture.
Preferably, in structure shown in formula one, m+n≤136, the degree of polymerization is excessively high to easily lead to catalytic efficiency decline.
Preferably, in structure shown in formula one, R1And R2It is each independently selected from hydrogen atom or methyl.
Preferably, in structure shown in formula one, R3~R6It is each independently selected from the alkane of any one carbon atom number≤4
Group.
Preferably, in structure shown in formula one, A1And A2It is each independently selected from the alkylene of any one carbon atom number≤4
Hydrocarbyl group.
Preferably, in structure shown in formula one, A1And A2It is each independently selected from ethylidene or propylidene.
Preferably, in structure shown in formula one, X1And X2It is each independently selected from tetrafluoroborate, hexafluoro-phosphate radical, sulfuric acid
Hydrogen radical, sulfate radical, dihydrogen phosphate, nitrate anion, bis- (fluoroform sulphonyl) imines roots, trifluoromethanesulfonic acid root, hydroxyl, fluorine from
Any one in son, chloride ion or bromide ion.
Preferably, in structure shown in formula one, B1And B2The quantity of carbon atom is 2~10 in group.
Preferably, in structure shown in formula one, B1And B2Group be each independently selected from ethoxy, hydroxypropyl, carboxyethyl or
Any one group in carboxylic propyl, in catalysis reaction, the B group of hydroxyl can be by forming hydrogen between epoxides
Key interacts, and the activation energy of reaction is greatly lowered, and then reactant is promoted efficiently to be converted into product.
Preferably, the preparation method includes the following steps:
The catalyst fines that compound containing epoxy group and partial size are 10~1000 μm are placed in closed reactor and are mixed
It closes uniformly, maintains temperature of reaction kettle in the range of 80~150 DEG C, carbon dioxide gas is continually fed into reaction kettle, maintain kettle
The pressure of interior reaction system carries out 1~8h of addition reaction, obtains cyclic carbonate ester in the range of 1~5MPa.
Numberical range of the present invention not only includes enumerated point value, further includes the above-mentioned numerical value not included
Arbitrary point value between range, as space is limited and for concise consideration, range described in the present invention no longer exclusive list includes
Specific point value.
Compared with prior art, the invention has the benefit that
(1) the present invention provides a kind of novel aminoacrylic acid class ion liquid polymer heterogeneous catalyst, it is utilized
It is catalyzed carbon dioxide and addition reaction occurs with the compound containing epoxy group, obtain cyclic carbonate ester, prepare ring using the above method
Carbonic ester selectivity with higher and conversion ratio, the purity of obtained cyclic carbonate ester product is up to 99.9mol%.
(2) compared to traditional method for preparing cyclic carbonate ester, ion liquid polymer catalyst used in the present invention
Active site is more, high catalytic efficiency, stabilization is not easily decomposed, preparation process is simple, additive amount is few, is easy to separate from liquid phase
Many advantages, such as, industrial application value with higher.
Specific embodiment
The technical scheme of the invention is further explained by means of specific implementation.
The ion liquid polymer used in following examples and reference examples can also be passed through by commercially available
Voluntarily synthesis obtains.
Illustratively, ion liquid polymer can synthesize to obtain as follows:
A certain amount of dimethylaminoethyl methacrylate monomer and bromoethanol is added in step (1) in 100mL flask,
12h is stirred at 25 DEG C to be reacted, and after reaction, is washed repeatedly reaction product 3 times with ethyl acetate, is later produced reaction
Object is dried in vacuum overnight at 40 DEG C, obtains white powder substance, as ionic liquid monomer；
The methanol of the ionic liquid monomer and 30mL that synthesize in 3g step (1) is added in step (2) in 100mL flask
With chloroform mixed liquor, the oil-soluble initiator azodiisobutyronitrile (AIBN) for the 0.3wt% that quality is monomer mass is then added,
Later, mixed liquor carries out Raolical polymerizable under 70 DEG C of nitrogen atmospheres, after reaction for 24 hours, is removed using Rotary Evaporators surplus
Remaining solvent is washed residual product 3 times repeatedly with ether and acetone, is finally dried in vacuum overnight at 40 DEG C to get ion is arrived
Liquid polymers 1, and measure stability.
It can be obtained by GPC test, the average degree of polymerization of obtained ion liquid polymer is 68.
By increasing and changing type, the replacement bromoethanol of polymerized monomer as other kinds of compound or change initiator
Additional amount, the ion liquid polymer of those skilled in the art available arbitrary structures and the degree of polymerization.
In various embodiments of the present invention, 6820GC-TCD type gas chromatograph that the yield of product is produced by agilent company
It is quantitative determined.
Embodiment 1
It is closed that 1 powder of ion liquid polymer that 143mmol propylene oxide and 300mg partial size are 100mm is placed in 750mL
It is uniformly mixed in reaction kettle, maintains temperature of reaction kettle at 110 DEG C, carbon dioxide gas is continually fed into reaction kettle, maintained in kettle
The pressure of reaction system carries out addition reaction 3h, obtains product propene carbonate, the yield of propene carbonate is in 2MPa
99.8mol%.
The ion liquid polymer 1 has the structure as shown in compound 1:
Embodiment 2
Difference with embodiment 1 is only that the ion liquid polymer 1 replaces with ion liquid polymer 2.
Embodiment 2 obtains product propene carbonate, and the yield of propene carbonate is 99.6mol%.
The ion liquid polymer 2 has the structure as shown in compound 2:
Embodiment 3
Difference with embodiment 1 is only that the ion liquid polymer 1 replaces with ion liquid polymer 3.
Embodiment 3 obtains product propene carbonate, and the yield of propene carbonate is 98.8mol%.
The ion liquid polymer 3 has the structure as shown in compound 3:
Embodiment 4
Difference with embodiment 1 is only that the ion liquid polymer 1 replaces with ion liquid polymer 4.
Embodiment 4 obtains product propene carbonate, and the yield of propene carbonate is 99.6mol%.
The ion liquid polymer 4 has the structure as shown in compound 4:
Embodiment 5
Difference with embodiment 1 is only that the partial size of 1 powder of ion liquid polymer is 10mm.
Embodiment 5 obtains product propene carbonate, and the yield of propene carbonate is 99.9mol%.
Embodiment 6
Difference with embodiment 1 is only that the additional amount of 1 powder of ion liquid polymer is 30mg.
Embodiment 6 obtains product propene carbonate, and the yield of propene carbonate is 99.2mol%.
Embodiment 7
Difference with embodiment 1 is only that the temperature of reaction kettle is controlled at 150 DEG C, the pressure control of reaction system in kettle
In 4.4MPa, the time of addition reaction is 1h.
Embodiment 7 obtains product propene carbonate, and the yield of propene carbonate is 99.5mol%.
Embodiment 8
Difference with embodiment 1 is only that the temperature of reaction kettle is controlled at 80 DEG C, and the pressure control of reaction system exists in kettle
1.2MPa, the time of addition reaction are 8h.
Embodiment 8 obtains product propene carbonate, and the yield of propene carbonate is 99.6mol%.
Embodiment 9
Difference with embodiment 1 is only that the ion liquid polymer 1 replaces with ion liquid polymer 5.
Embodiment 9 obtains product propene carbonate, and the yield of propene carbonate is 98.1mol%.
The ion liquid polymer 5 has the structure as shown in compound 5:
Embodiment 10
Difference with embodiment 1 is only that the ion liquid polymer 1 replaces with ion liquid polymer 6.
Embodiment 10 obtains product propene carbonate, and the yield of propene carbonate is 95.8mol%.
The ion liquid polymer 6 has the structure as shown in compound 6:
Embodiment 11
Difference with embodiment 1 is only that, propylene oxide therein is replaced with to the epoxychloropropane of same molar.
Embodiment 11 obtains product carbonic acid chloropropene ester, and the yield of carbonic acid chloropropene ester is 96.4mol%.
Embodiment 12
Difference with embodiment 1 is only that, propylene oxide therein is replaced with to the styrene oxide of same molar.
Embodiment 12 obtains product carbonic acid styrene esters, and the yield of carbonic acid styrene esters is 93.9mol%.
In conclusion the present invention provides a kind of novel aminoacrylic acid class ion liquid polymer heterogeneous catalyst,
Carbon dioxide is catalyzed using it, addition reaction occurs with the compound containing epoxy group, obtain cyclic carbonate ester, use the above method
Cyclic carbonate ester selectivity with higher and conversion ratio are prepared, the purity of obtained cyclic carbonate ester product is up to 99.9mol%, phase
Compared with traditional method for preparing cyclic carbonate ester, the active site of ion liquid polymer catalyst used in the present invention
More, high catalytic efficiency, stabilization is not easily decomposed, preparation process is simple, additive amount is few, is easy many advantages, such as separating from liquid phase,
Industrial application value with higher.
Particular embodiments described above has carried out further in detail the purpose of the present invention, technical scheme and beneficial effects
It describes in detail bright, it should be understood that the above is only a specific embodiment of the present invention, is not intended to restrict the invention, it is all
Within the spirit and principles in the present invention, any modification, equivalent substitution, improvement and etc. done should be included in guarantor of the invention
Within the scope of shield.
Claims (10)
1. a kind of preparation method of cyclic carbonate ester, which is characterized in that the preparation method includes the following steps:
Use the synthesis of catalyst cyclic carbonate ester；
It include ion liquid polymer in the catalyst；
The ion liquid polymer has the structure as shown in formula one:
Wherein, m and n is each independently selected from random natural number, and m+n >=4；
R1And R2It is each independently selected from hydrogen atom or any one alkane group；
R3~R6It is each independently selected from any one alkane group；
A1And A2It is each independently selected from any one alkylene hydrocarbyl group；
X1And X2It is each independently selected from any one compatibility anion；
B1And B2It is each independently selected from the alkane group of any one alkane group, hydroxy-end capped alkane group, carboxy blocking
Or the alkane group of sulfonate radical sealing end.
2. preparation method according to claim 1, which is characterized in that the preparation method includes the following steps:
Addition reaction occurs under the catalysis of catalyst for carbon dioxide and the compound containing epoxy group, obtains cyclic carbonate ester.
3. preparation method according to claim 2, which is characterized in that the reaction temperature of the addition reaction is 80~150
℃；
Preferably, the reaction pressure of the addition reaction is 1~5MPa；
Preferably, the reaction time of the addition reaction is 1~8h.
4. preparation method described according to claim 1~one of 3, which is characterized in that the partial size of the catalyst be 10~
100mm；
Preferably, the catalyst and the mass ratio of the epoxy group in the compound containing epoxy group are 1:2~200.
5. preparation method according to claim 2, which is characterized in that the compound containing epoxy group is epoxy second
Alkane, propylene oxide, epoxy butane, epoxychloropropane, styrene oxide, 7-oxa-bicyclo[4.1.0 or oxidation pentamethylene in any one
Or at least two mixture.
6. preparation method described according to claim 1~one of 5, which is characterized in that in structure shown in formula one, m+n≤
136；
Preferably, in structure shown in formula one, R1And R2It is each independently selected from hydrogen atom or methyl；
Preferably, in structure shown in formula one, R3~R6It is each independently selected from the alkane group of any one carbon atom number≤4.
7. preparation method described according to claim 1~one of 6, which is characterized in that in structure shown in formula one, A1And A2Respectively
From the alkylene hydrocarbyl group independently selected from any one carbon atom number≤4；
Preferably, in structure shown in formula one, A1And A2It is each independently selected from ethylidene or propylidene.
8. preparation method described according to claim 1~one of 7, which is characterized in that in structure shown in formula one, X1And X2Respectively
From independently selected from tetrafluoroborate, hexafluoro-phosphate radical, bisulfate ion, sulfate radical, dihydrogen phosphate, nitrate anion, bis- (fluoroforms
Alkane sulphonyl) any one in imines root, trifluoromethanesulfonic acid root, hydroxyl, fluorine ion, chloride ion or bromide ion.
9. preparation method described according to claim 1~one of 8, which is characterized in that in structure shown in formula one, B1And B2Base
The quantity of carbon atom is 2~10 in group；
Preferably, in structure shown in formula one, B1And B2Group is each independently selected from ethoxy, hydroxypropyl, carboxyethyl or carboxylic third
Any one group in base.
10. preparation method described according to claim 1~one of 9, which is characterized in that the preparation method includes following step
It is rapid:
Compound containing epoxy group is placed in closed reactor with the catalyst fines that partial size is 10~1000 μm and is mixed
It is even, it maintains temperature of reaction kettle in the range of 80~150 DEG C, carbon dioxide gas is continually fed into reaction kettle, remain anti-in kettle
It answers the pressure of system in the range of 1~5MPa, carries out 1~8h of addition reaction, obtain cyclic carbonate ester.
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Cited By (7)
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| CN112159386A (en) * | 2020-09-16 | 2021-01-01 | 中国科学院过程工程研究所 | Method for synthesizing cyclic carbonate by mild catalysis of ionic liquid crosslinked polymer |
| CN112250656A (en) * | 2020-11-03 | 2021-01-22 | 中国科学院过程工程研究所 | Method for catalytically synthesizing cyclic carbonate based on multi-active-center ionic liquid |
| CN112341394A (en) * | 2020-11-03 | 2021-02-09 | 中国科学院过程工程研究所 | Method for preparing cyclic carbonate ester by catalysis of hydrogen bond donor functionalized polymeric ionic liquid |
| CN112495431A (en) * | 2020-11-24 | 2021-03-16 | 中国科学院过程工程研究所 | Method for synthesizing cyclic carbonate by mild catalysis of multi-site ionic liquid |
| 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 |
| CN114276322A (en) * | 2022-01-06 | 2022-04-05 | 惠州市绿色能源与新材料研究院 | Method for preparing cyclic carbonate by photo-initiated polymerization of ionic liquid material |
| CN115739179A (en) * | 2022-11-01 | 2023-03-07 | 南京大学 | Composite polymer catalyst, and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112159386A (en) * | 2020-09-16 | 2021-01-01 | 中国科学院过程工程研究所 | Method for synthesizing cyclic carbonate by mild catalysis of ionic liquid crosslinked polymer |
| CN112159386B (en) * | 2020-09-16 | 2021-12-03 | 中国科学院过程工程研究所 | Method for synthesizing cyclic carbonate by mild catalysis of ionic liquid crosslinked polymer |
| CN112250656A (en) * | 2020-11-03 | 2021-01-22 | 中国科学院过程工程研究所 | Method for catalytically synthesizing cyclic carbonate based on multi-active-center ionic liquid |
| CN112341394A (en) * | 2020-11-03 | 2021-02-09 | 中国科学院过程工程研究所 | Method for preparing cyclic carbonate ester by catalysis of hydrogen bond donor functionalized polymeric ionic liquid |
| CN112250656B (en) * | 2020-11-03 | 2022-06-17 | 中国科学院过程工程研究所 | Method for catalytically synthesizing cyclic carbonate based on multi-active-center ionic liquid |
| CN112495431A (en) * | 2020-11-24 | 2021-03-16 | 中国科学院过程工程研究所 | Method for synthesizing cyclic carbonate by mild catalysis of multi-site ionic liquid |
| CN112495431B (en) * | 2020-11-24 | 2022-02-11 | 中国科学院过程工程研究所 | Method for synthesizing cyclic carbonate by mild catalysis of multi-site ionic liquid |
| 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 |
| CN114276322A (en) * | 2022-01-06 | 2022-04-05 | 惠州市绿色能源与新材料研究院 | Method for preparing cyclic carbonate by photo-initiated polymerization of ionic liquid material |
| CN115739179A (en) * | 2022-11-01 | 2023-03-07 | 南京大学 | Composite polymer catalyst, and preparation method and application thereof |
| CN115739179B (en) * | 2022-11-01 | 2024-04-09 | 南京大学 | Composite high-molecular catalyst and preparation method and application thereof |
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