CN102838583A - Method for preparing cyclic carbonate by using functionalized quaternary phosphonium salt ionic liquid - Google Patents
Method for preparing cyclic carbonate by using functionalized quaternary phosphonium salt ionic liquid Download PDFInfo
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- CN102838583A CN102838583A CN201210330545XA CN201210330545A CN102838583A CN 102838583 A CN102838583 A CN 102838583A CN 201210330545X A CN201210330545X A CN 201210330545XA CN 201210330545 A CN201210330545 A CN 201210330545A CN 102838583 A CN102838583 A CN 102838583A
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- ionic liquid
- cyclic carbonate
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- quaternary alkylphosphonium
- alkylphosphonium salt
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Abstract
A method for preparing cyclic carbonate by using functionalized quaternary phosphonium salt ionic liquid is characterized in that the functionalized quaternary phosphonium salt ionic liquid is served as a catalyst, the amount of the catalyst is 1 per mill-2% of a molar weight of an epoxy compound, the reaction pressure is 0.1-10.0MPa, the reaction temperature is 25 DEG C-180 DEG C, the reaction time is 0.5-24 hours, and carbon dioxide and the epoxy compound are catalyzed under the conditions to additionally synthesize the corresponding cyclic carbonate. The preparation method is soft in reaction condition, and the used catalyst is a single-component catalyst which has the advantages of low cost, high activity and selectivity, good stability and the like.
Description
Technical field
The present invention relates to prepare the method for cyclic carbonate, specifically referring to a kind of is raw material with carbonic acid gas and epoxy compounds, is the method for preparing cyclic carbonate under the catalyzer condition through cycloaddition at functionalization quaternary alkylphosphonium salt ionic liquid.
Technical background
Carbonic acid gas is topmost greenhouse gases on the present earth, but simultaneously also is nontoxic, cheapness and the abundant C1 resource of reserves.Along with Greenhouse effect and fossil oil shortage the increasingly sharpening of " carbon source crisis " of causing, CO
2Recycling becomes one of hot subject of international in recent years competitively research.Though CO
2Can be converted into multiple useful chemical (as: methyl alcohol, acetic acid, Whitfield's ointment, urea, carbonic ether etc.), but directly with CO
2For the industrialized route of raw material few.Wherein, through CO
2Cheap with the reaction of epoxide cycloaddition synthesizing annular carbonate because of its cost of material, atom utilization is high, meet " Green Chemistry " but development become minority industrialized utilization CO
2One of approach [Green Chem., 2005,7:518-523].Cyclic carbonate is one type of crucial chemical products; Have favorable biological degradability, solvability and other physical properties; It is good clean polar solvent; Can be used for also that resol production, polycarbonate are synthetic, thermosetting resin is synthetic, thermal recording material is synthetic, and as electrolytic solution, metal extraction agent, cosmetics additive and the chemical intermediate etc. of high-energy-density lithium cell and electric capacity.
Over past ten years, advantage such as ionic-liquid catalyst is simple, with low cost because of its preparation, kind is various, textural property is adjustable is widely used as the catalyzer [Appl. Catal. A:Gen., 2009,366:2-12] of cycloaddition synthesizing annular carbonate.Use therein more be imidazole salts ionic liquid [Green Chem, 2012,14:654-660], pyridinium salt ionic liquid [Chem. Eng.; 2008; 25:471-473] 、 quaternary alkylphosphonium salt ionic liquid [Appl. Catal. A:Gen., 2008,341:106-111] and quaternary ammonium salt ionic liquid [Appl. Catal. A:Gen.; 2005,287:221-226].Though these ionic liquids have certain catalytic activity to cycloaddition reaction; But all a bit or some problem: self activity is not high or under the condition that promotors such as metal halide exist, just show catalytic activity preferably; Stability is bad, and active ingredient is to water sensitive, severe reaction conditions etc.Especially quaternary alkylphosphonium salt ionic-liquid catalyst; Only there is [Appl. Catal. A:Gen. at transition metal halide promotors such as (like zinc halides); 2008,341:106-111], or [Green Chem. under the super critical condition; 2003,5:92-94] just have a catalytic activity preferably.
Therefore, develop and a kind ofly exist, and the catalyzer that under mild reaction conditions, self promptly has a greater activity is the difficult problem that solution is needed in present cycloaddition field badly at solvent-free and promotor.
Summary of the invention
The object of the present invention is to provide a kind of functionalization quaternary alkylphosphonium salt ionic liquid to prepare the method for cyclic carbonate; Be implemented in mild reaction conditions and do not add any solvent and the promotor condition under, efficient, highly selective is by carbonic acid gas and epoxy compounds cycloaddition synthesizing annular carbonate.
Reaction expression of the present invention is:
Work as R
1During=H, R
2Be H, CH
3, CH
2Cl, C
2H
5, C
4H
9, C
6H
5, C
4H
9O, C
7H
7A kind of among the O.
Work as R
1During ≠ H, the structure of epoxy compounds is:
A kind of functionalization quaternary alkylphosphonium salt ionic liquid prepares the method for cyclic carbonate; It is characterized in that functions of use quaternary alkylphosphonium salt ionic liquid is as catalyzer; At catalyst levels is 1 ‰ ~ 2% of epoxy compounds molar weight, and reaction pressure is 0.1 ~ 10.0 MPa, and temperature of reaction is 25
oC ~ 180
oC, the reaction times is catalysis carbonic acid gas and the synthetic corresponding cyclic carbonic ether of epoxy compounds cycloaddition under 0.5 ~ 24 hour condition.
Said functionalization quaternary alkylphosphonium salt ionic liquid has following general structure:
In the formula: n is 1 to 8 integer;
A is selected from a kind of in hydroxyl, carboxyl, amido, acyl group or the ester group;
Substituent R
1, R
2, R
3For containing saturated or unsaturated alkyl, aromatic base, the heterocyclic group of 1 ~ 20 carbon atom, R
1, R
2, R
3Can be identical, also can be different;
X wherein
-Be selected from F
–, Cl
–, Br
–, I
–, BF
4 –, BF
6 –, ClO
4 –, BH
4 –, SbF
6 –, ZnCl
3 –, SnCl
3 –, CF
3SO
3 –, NO
2 –, NO
3 –, SO
4 –, PO
4 –, RCOO
–, N (FSO
2)
2 –, N (CF
3SO
2)
2 –, C (CF
3SO
2)
3 –, CF
3COO
–, CF
3SO
3 –, CH
3SO
3 –Or ROSO
3 –In a kind of.
R
1, R
2And R
3Preferred alkyl and aromatic group.
X
–Be halide-ions, wherein preferred Cl
–, Br
–And I
–
The structure of raw material epoxy compounds is:
Work as R
1During=H, R
2Be H, CH
3, CH
2Cl, C
2H
5, C
4H
9, C
6H
5, C
4H
9O, C
7H
7A kind of among the O.
Work as R
1During ≠ H, the structure of epoxy compounds is:
Technique effect of the present invention is: this preparing method's reaction conditions is gentle, and catalyst system therefor is a single component catalyst, has that cost is low, an activity and selectivity is high, and advantage such as good stability.
Embodiment
In order to further specify details of the present invention, enumerate some embodiment below, but the invention is not restricted to following embodiment, before and after not breaking away from, under the scope of said aim, change and implement to be included in the technical scope of the present invention.
Embodiment 1
In 100 mL stainless steel autoclaves, add 2-hydroxyethyl tri-phenyl-phosphorus bromide 0.1390 g successively, propylene oxide 2.5 mL, sealed reactor charges into carbonic acid gas to 2.5 MPa, slowly is raised to 120 by the intelligent constant-temperature controller then
oC reacts 4.0 h, is cooled to room temperature, opens reaction kettle, opens the vent valve excessive carbon dioxide of draining, and through the gas chromatograph analysis, gained cyclic carbonate selectivity is 99.1% with products therefrom, and yield is 96.8%.
Embodiment 2
With embodiment 1, catalyst system therefor is a 2-aminoethyl tri-phenyl-phosphorus bromide, and add-on is 0.1390 g, and other conditions are constant, and gained cyclic carbonate selectivity is 99.0%, and yield is 95.3%.
Embodiment 3
With embodiment 1, catalyst system therefor is the ethyloic tri-phenyl-phosphorus bromide, and add-on is 0.1500 g, and other conditions are constant, and gained cyclic carbonate selectivity is 99.8%, and yield is 98.3%.
Embodiment 4
With embodiment 1, temperature of reaction is 110
OC, reaction pressure is 3.0 MPa, reaction times 4.5 h, and other conditions are constant, and gained cyclic carbonate selectivity is 99.4%, and yield is 93.5%.
Embodiment 5
With embodiment 1, temperature of reaction is 120
OC, reaction pressure is 5.0 MPa, and other conditions are constant, and gained cyclic carbonate selectivity is 100%, and yield is 96.8%.
Embodiment 6
With embodiment 1, temperature of reaction is 130
OC, reaction pressure is 2.0 MPa, reaction times 2.0 h, and other conditions are constant, and gained cyclic carbonate selectivity is 99.2%, and yield is 92.7%.
Embodiment 7
With embodiment 1,2-hydroxyethyl tri-phenyl-phosphorus bromide consumption is 0.0139 g, and temperature of reaction is 130
oC, reaction pressure 2.0 MPa, reaction times 10 h, other conditions are constant, and gained cyclic carbonate selectivity is 100%, and yield is 96.8%.
Embodiment 8
With embodiment 1,2-hydroxyethyl tri-phenyl-phosphorus bromide consumption is 0.2780 g, and temperature of reaction is 130
OC, reaction pressure is 3.0 MPa, and the reaction times is 2 h, and other conditions are constant, and gained cyclic carbonate selectivity is 99.9%, yield is 99.9%.
Embodiment 9
With embodiment 1, used epoxy compounds is epoxy chloropropane 2.5 mL, and catalyzer 2-hydroxyethyl tri-phenyl-phosphorus bromide is 0.1241 g, and temperature of reaction is 120
OC, the reaction times is 4 h, other conditions are constant, and gained cyclic carbonate selectivity 97.0%, yield is 97.2%.
Embodiment 10
With embodiment 1, used epoxy compounds is Styryl oxide 2.5 mL, and catalyzer 2-hydroxyethyl tri-phenyl-phosphorus bromide is 0.0852 g, and temperature of reaction is 120
OC, the reaction times is 4 h, other conditions are constant, and gained cyclic carbonate selectivity 99.2%, yield is 91.0%.
Embodiment 11
With embodiment 1, used epoxy compounds is epoxy cyclohexane 2.5 mL, and catalyzer 2-hydroxyethyl tri-phenyl-phosphorus bromide is 0.0957 g, and temperature of reaction is 120
OC, the reaction times is 4 h, other conditions are constant, and gained cyclic carbonate selectivity 99.1%, yield is 73.5%.
Embodiment 12
With embodiment 1, used epoxy compounds is phenyl glycidyl ether 2.5 mL, and catalyzer 2-hydroxyethyl tri-phenyl-phosphorus bromide is 0.0718 g, and temperature of reaction is 120
OC, the reaction times is 4 h, other conditions are constant, and gained cyclic carbonate selectivity 99.1%, yield is 93.9%.
Claims (7)
1. a functionalization quaternary alkylphosphonium salt ionic liquid prepares the method for cyclic carbonate; It is characterized in that functions of use quaternary alkylphosphonium salt ionic liquid is as catalyzer; At catalyst levels is 1 ‰ ~ 2% of epoxy compounds molar weight, and reaction pressure is 0.1 ~ 10.0 MPa, and temperature of reaction is 25
oC ~ 180
oC, the reaction times is catalysis carbonic acid gas and the synthetic corresponding cyclic carbonic ether of epoxy compounds cycloaddition under 0.5 ~ 24 hour condition.
2. a kind of functionalization quaternary alkylphosphonium salt ionic liquid according to claim 1 prepares the method for cyclic carbonate, it is characterized in that said functionalization quaternary alkylphosphonium salt ionic liquid has following general structure:
In the formula: n is 1 to 8 integer;
A is selected from a kind of in hydroxyl, carboxyl, amido, acyl group or the ester group;
Substituent R
1, R
2, R
3For containing saturated or unsaturated alkyl, aromatic base, the heterocyclic group of 1 ~ 20 carbon atom, R
1, R
2, R
3Can be identical, also can be different;
X wherein
-Be selected from F
–, Cl
–, Br
–, I
–, BF
4 –, BF
6 –, ClO
4 –, BH
4 –, SbF
6 –, ZnCl
3 –, SnCl
3 –, CF
3SO
3 –, NO
2 –, NO
3 –, SO
4 –, PO
4 –, RCOO
–, N (FSO
2)
2 –, N (CF
3SO
2)
2 –, C (CF
3SO
2)
3 –, CF
3COO
–, CF
3SO
3 –, CH
3SO
3 –Or ROSO
3 –In a kind of.
3. a kind of functionalization quaternary alkylphosphonium salt ionic liquid according to claim 2 prepares the method for cyclic carbonate, it is characterized in that R
1, R
2And R
3Preferred alkyl and aromatic group.
4. a kind of functionalization quaternary alkylphosphonium salt ionic liquid according to claim 2 prepares the method for cyclic carbonate, it is characterized in that X
–Be halide-ions, wherein preferred Cl
–, Br
–And I
–
5. a kind of functionalization quaternary alkylphosphonium salt ionic liquid according to claim 1 prepares the method for cyclic carbonate, it is characterized in that the structure of raw material epoxy compounds is:
6. a kind of functionalization quaternary alkylphosphonium salt ionic liquid according to claim 5 prepares the method for cyclic carbonate, it is characterized in that working as R
1During=H, R
2Be H, CH
3, CH
2Cl, C
2H
5, C
4H
9, C
6H
5, C
4H
9O, C
7H
7A kind of among the O.
7. a kind of functionalization quaternary alkylphosphonium salt ionic liquid according to claim 5 prepares the method for cyclic carbonate, it is characterized in that working as R
1During ≠ H, the structure of epoxy compounds is:
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|---|---|---|---|---|
| CN103664863A (en) * | 2013-12-20 | 2014-03-26 | 黑龙江大学 | Method for synthesizing cyclic carbonate by catalysis of amino functional ionic liquid |
| CN104974128A (en) * | 2015-07-24 | 2015-10-14 | 大连理工大学 | Method for preparing cyclic carbonate by using supported quaternary phosphonium salt catalyst |
| CN105294643A (en) * | 2014-07-24 | 2016-02-03 | 中国石油化工股份有限公司 | Catalyst and method for preparing ethylene carbonate from oxirane and carbon dioxide |
| CN105367541A (en) * | 2014-08-11 | 2016-03-02 | 中国科学院过程工程研究所 | Method for synthesizing cyclic carbonate through polyionic liquid nanometer catalysis cycloaddition reaction |
| CN105381819A (en) * | 2015-12-09 | 2016-03-09 | 大连理工大学 | Supported biquaternary ammonium salt catalyst, preparation method, and preparation method of cyclic carbonate |
| CN109970700A (en) * | 2019-04-25 | 2019-07-05 | 青岛科技大学 | A kind of quaternary phosphine type eutectic ionic liquid catalysis carbon dioxide couples the method for preparing cyclic carbonate with epoxides |
| CN109970699A (en) * | 2019-04-25 | 2019-07-05 | 青岛科技大学 | A kind of method of the fixed carbon dioxide synthesizing annular carbonate of chemistry under novel eutectic ionic liquid normal temperature and pressure conditions |
| CN113292530A (en) * | 2021-04-30 | 2021-08-24 | 深圳新宙邦科技股份有限公司 | Method for preparing cyclic carbonate from quaternary phosphonium salt |
| CN114014833A (en) * | 2021-12-09 | 2022-02-08 | 浙江理工大学 | Method for preparing cyclic carbonate from low-concentration carbon dioxide and catalyst used in method |
| CN115181087A (en) * | 2022-08-25 | 2022-10-14 | 山东东岳高分子材料有限公司 | Method for preparing ethylene carbonate by ionic liquid composite catalyst |
| CN115724820A (en) * | 2022-11-24 | 2023-03-03 | 惠州市绿色能源与新材料研究院 | Method for preparing cyclic carbonate by catalyzing carbon dioxide with phosphine-based complex |
| CN115779963A (en) * | 2022-11-30 | 2023-03-14 | 深圳新宙邦科技股份有限公司 | Application of catalyst in catalyzing reaction of epoxy compound and carbon dioxide |
| CN115894428A (en) * | 2022-11-08 | 2023-04-04 | 中国科学院过程工程研究所 | Method for synthesizing carbonic ester by double-effect ionic liquid composite system |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102391241A (en) * | 2011-10-21 | 2012-03-28 | 中国科学院过程工程研究所 | Method for preparing cyclic carbonate with chitosan loading type catalyst |
-
2012
- 2012-09-10 CN CN201210330545XA patent/CN102838583A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102391241A (en) * | 2011-10-21 | 2012-03-28 | 中国科学院过程工程研究所 | Method for preparing cyclic carbonate with chitosan loading type catalyst |
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| CN103664863A (en) * | 2013-12-20 | 2014-03-26 | 黑龙江大学 | Method for synthesizing cyclic carbonate by catalysis of amino functional ionic liquid |
| CN103664863B (en) * | 2013-12-20 | 2015-10-28 | 黑龙江大学 | The method of the ionic liquid-catalyzed synthesizing annular carbonate of amino functional |
| CN105294643A (en) * | 2014-07-24 | 2016-02-03 | 中国石油化工股份有限公司 | Catalyst and method for preparing ethylene carbonate from oxirane and carbon dioxide |
| CN105294643B (en) * | 2014-07-24 | 2018-07-13 | 中国石油化工股份有限公司 | Ethylene oxide and carbon dioxide prepare the catalyst and its method of ethylene carbonate |
| CN105367541A (en) * | 2014-08-11 | 2016-03-02 | 中国科学院过程工程研究所 | Method for synthesizing cyclic carbonate through polyionic liquid nanometer catalysis cycloaddition reaction |
| CN105367541B (en) * | 2014-08-11 | 2018-06-15 | 中国科学院过程工程研究所 | The method of poly ion liquid nano-catalytic cycloaddition reaction synthesizing annular carbonate |
| CN104974128A (en) * | 2015-07-24 | 2015-10-14 | 大连理工大学 | Method for preparing cyclic carbonate by using supported quaternary phosphonium salt catalyst |
| CN104974128B (en) * | 2015-07-24 | 2017-12-26 | 大连理工大学 | A kind of method of support type quaternary alkylphosphonium salt catalyst preparation cyclic carbonate |
| CN105381819A (en) * | 2015-12-09 | 2016-03-09 | 大连理工大学 | Supported biquaternary ammonium salt catalyst, preparation method, and preparation method of cyclic carbonate |
| CN105381819B (en) * | 2015-12-09 | 2018-04-10 | 大连理工大学 | The preparation method of support type bi-quaternary ammonium salt catalyst and preparation method thereof and cyclic carbonate |
| CN109970700A (en) * | 2019-04-25 | 2019-07-05 | 青岛科技大学 | A kind of quaternary phosphine type eutectic ionic liquid catalysis carbon dioxide couples the method for preparing cyclic carbonate with epoxides |
| CN109970699A (en) * | 2019-04-25 | 2019-07-05 | 青岛科技大学 | A kind of method of the fixed carbon dioxide synthesizing annular carbonate of chemistry under novel eutectic ionic liquid normal temperature and pressure conditions |
| CN109970699B (en) * | 2019-04-25 | 2021-04-27 | 青岛科技大学 | Method for synthesizing cyclic carbonate by chemically fixing carbon dioxide under normal temperature and pressure conditions through novel eutectic ionic liquid |
| CN109970700B (en) * | 2019-04-25 | 2021-04-27 | 青岛科技大学 | Method for preparing cyclic carbonate by coupling carbon dioxide and epoxide under catalysis of quaternary phosphonium eutectic ionic liquid |
| CN113292530A (en) * | 2021-04-30 | 2021-08-24 | 深圳新宙邦科技股份有限公司 | Method for preparing cyclic carbonate from quaternary phosphonium salt |
| CN114014833A (en) * | 2021-12-09 | 2022-02-08 | 浙江理工大学 | Method for preparing cyclic carbonate from low-concentration carbon dioxide and catalyst used in method |
| CN114014833B (en) * | 2021-12-09 | 2023-09-15 | 浙江理工大学 | Method for preparing cyclic carbonate from low-concentration carbon dioxide and catalyst used by method |
| CN115181087A (en) * | 2022-08-25 | 2022-10-14 | 山东东岳高分子材料有限公司 | Method for preparing ethylene carbonate by ionic liquid composite catalyst |
| CN115894428A (en) * | 2022-11-08 | 2023-04-04 | 中国科学院过程工程研究所 | Method for synthesizing carbonic ester by double-effect ionic liquid composite system |
| CN115724820A (en) * | 2022-11-24 | 2023-03-03 | 惠州市绿色能源与新材料研究院 | Method for preparing cyclic carbonate by catalyzing carbon dioxide with phosphine-based complex |
| CN115779963A (en) * | 2022-11-30 | 2023-03-14 | 深圳新宙邦科技股份有限公司 | Application of catalyst in catalyzing reaction of epoxy compound and carbon dioxide |
| CN115779963B (en) * | 2022-11-30 | 2023-09-08 | 深圳新宙邦科技股份有限公司 | Application of catalyst in catalyzing reaction of epoxy compound and carbon dioxide |
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Application publication date: 20121226 |