Frontiers of Chemical Science and Engineering >
Polyethylene glycol-supported ionic liquid as a highly efficient catalyst for the synthesis of propylene carbonate under mild conditions
Received date: 10 Jan 2012
Accepted date: 16 Mar 2012
Published date: 05 Sep 2012
Copyright
The coupling reaction of propylene and CO2 to form propylene carbonate (PC) was promoted by an ionic liquid (IL) covalently bound to polyethylene glycol (PEG). The supported ionic liquid, which has both acidic and basic components, proved to be an active catalyst for PC synthesis under mild conditions. The effects of different cations and anions, reaction temperature, CO2 pressure, and reaction time were investigated. It was demonstrated that the acid group in the catalyst plays an important role in the reaction. With this system, a high PC yield (95%) was achieved under mild conditions (3.0 MPa, 120°C and 4 h) without a co-solvent. In addition, the catalyst was readily recovered and reused. Based on the experimental results, a plausible mechanism for the catalyst was proposed.
Rui YAO , Hua WANG , Jinyu HAN . Polyethylene glycol-supported ionic liquid as a highly efficient catalyst for the synthesis of propylene carbonate under mild conditions[J]. Frontiers of Chemical Science and Engineering, 2012 , 6(3) : 239 -245 . DOI: 10.1007/s11705-012-1297-y
1 |
Sakakura T, Choi J C, Yasuda H. Transformation of carbon dioxide. Chemical Reviews, 2007, 107(6): 2365–2387
|
2 |
Dai W L, Luo S L, Yin S F, Au C T. The direct transformation of carbon dioxide to organic carbonates over heterogeneous catalysts. Applied Catalysis A: General, 2009, 366(1): 2–12
|
3 |
Zhang S J, Chen Y H, Li F W, Lu X M, Dai W B, Mori R. Fixation and conversion of CO2 using ionic liquids. Catalysis Today, 2006, 115(1–4): 61–69
|
4 |
Sako T, Fukai T, Sahashi R, Sone M, Matsuno M. Cycloaddition of oxirane group with carbon dioxide in the supercritical homogeneous state. Industrial & Engineering Chemistry Research, 2002, 41(22): 5353–5358
|
5 |
Caló V, Nacci A, Monopoli A, Fanizzi A. Cyclic carbonate formation from carbon dioxide and oxiranes in tetrabutylammonium halides as solvents and catalysts. Organic Letters, 2002, 4(15): 2561–2563
|
6 |
Chang T, Jing H W, Jin L L, Qiu W Y. Quaternary onium tribromide catalyzed cyclic carbonate synthesis from carbon dioxide and epoxides. Journal of Molecular Catalysis A: Chemical, 2007, 264(1–2): 241–247
|
7 |
He L N, Yasuda T, Sakakura T. New procedure for recycling homogeneous catalyst: propylene carbonate synthesis under supercritical CO2. Green Chemistry, 2003, 5(1): 92–94
|
8 |
Jiang J L, Gao F X, Hua R M, Qiu X Q. Re(CO)5Br-catalyzed coupling of epoxides with CO2 affording cyclic carbonates under solvent-free conditions. Journal of Organic Chemistry, 2005, 70(1): 381–383
|
9 |
Kim H S, Kim J J, Kwon H N, Chung M J, Lee B G, Jang H G. Well-defined highly active heterogeneous catalyst system for the coupling reactions of carbon dioxide and epoxides. Journal of Catalysis, 2002, 205(1): 226–229
|
10 |
Kawanami H, Sasaki A, Matsui K, Ikushima Y. A rapid and effective synthesis of propylene carbonate using a supercritical CO2-ionic liquid system. Chemical Communications, 2003, 2003(7): 896–897
|
11 |
Wang J Q, Yue X D, Cai F, He L N. Solventless synthesis of cyclic carbonates from carbon dioxide and epoxides catalyzed by silica-supported ionic liquids under supercritical conditions. Catalysis Communications, 2007, 8(2): 167–172
|
12 |
Peng J J, Deng Y Q. Cycloaddition of carbon dioxide to propylene oxide catalyzed with ionic liquid. New Journal of Chemistry, 2001, 25(4): 639–641
|
13 |
Yang H Z, Gu Y L, Deng Y Q, Shi F. Electrochemical activation of carbon dioxide in ionic liquid: synthesis of cyclic carbonates at mild reaction conditions. Chemical Communications, 2002, 2002(3): 274–275
|
14 |
Kim H S, Kim J J, Kim H, Jang H G. Imidazolium zinc tetrahalide-catalyzed coupling reaction of CO2 and ethylene oxide or propylene oxide. Journal of Catalysis, 2003, 220(1): 44–46
|
15 |
Li F, Xiao L, Xia C, Hu B. Chemical fixationof CO2 with highly efficient ZnCl2/[BMIm]Br catalyst system. Tetrahedron Letters, 2004, 45(45): 8307–8310
|
16 |
Sun J M, Fujita S I, Arai M. Development in the green synthesis of cyclic carbonate from carbon dioxide using ionic liquids. Journal of Organometallic Chemistry, 2005, 690(15): 3490–3497
|
17 |
Xiao L F, Li F W, Peng J J, Xia C G. Immobilized ionic liquid zinc chloride: heterogeneous catalyst for synthesis of cyclic carbonates from carbon dioxide and epoxides. Journal of Molecular Catalysis A: Chemical, 2006, 253(1–2): 265–269
|
18 |
Sun J, Zhang S J, Cheng W G, Ren G Y. Hydroxyl-functionalized ionic liquid: a novel efficient catalyst for chemical fixation of CO2 to cyclic carbonate. Tetrahedron Letters, 2008, 49(22): 3588–3591
|
19 |
Kim Y J, Varma R S. Tetrahaloindate(III)-based ionic liquids in the coupling reaction of carbon dioxide and epoxides to generate cyclic carbonates: H-bonding and mechanistic studies. Journal of Organic Chemistry, 2005, 70(20): 7882–7891
|
20 |
Tian J S, Miao C X, Wang J Q, Cai F, Du Y, Zhao Y, He L N. Efficient synthesis of dimethy carbonate from methanol, propylene oxide and CO2 catalyzed by recyclable inorganic base/phosphonium halide-functionalized polyethylene glycol. Green Chemistry, 2007, 9(6): 566–571
|
21 |
Dai W L, Chen L, Yin S F, Luo S L, Au C T. 3-(2-Hydroxyl-ethyl)-1-propylimidazolium bromide immobilized on SBA-15 as efficient catalyst for the synthesis of cyclic carbonates via the coupling of carbon dioxide with epoxides. Catalysis Letters, 2010, 135(3–4): 295–304
|
22 |
Wang J Q, Kong D L, Chen J Y, Cai F, He L N. Synthesis of cyclic carbonates from epoxides and carbon dioxide over silica-supported quaternary ammonium salts under supercritical conditions. Journal of Molecular Catalysis A: Chemical, 2006, 249(1–2): 143–148
|
23 |
Du Y, Wang J Q, Chen J Y, Cai F, Tian J S, Kong D L, He L N. A poly(ethylene glycol)-supported quaternary ammonium salt for highly efficient and environmentally friendly chemical fixation of CO2 with epoxides under supercritical conditions. Tetrahedron Letters, 2006, 47(8): 1271–1275
|
24 |
Sun J, Cheng W G, Fan W, Wang Y H, Meng Z Y, Zhang S J. Reusable and efficient polymer-supported task-specific ionic liquid catalyst for cycloaddition of epoxide with CO2. Catalysis Today, 2009, 148(3–4): 361–367
|
25 |
Ulusoy M, Cetinkaya E, Cetinkaya B. Conversion of carbon dioxide to cyclic carbonates using diimine Ru(II) complexes as catalysts. Applied Organometallic Chemistry, 2009, 23(2): 68–74
|
26 |
Xie Y, Zhang Z F, Jiang T, He J L, Han B X, Wu T B, Ding K L. CO2 cycloaddition reactions catalyzed by an ionic liquid grafted onto a highly cross-linked polymer matrix. Angewandte Chemie International Edition, 2007, 46(38): 7255–7258
|
27 |
Heldebrant D J, Witt H N, Walsh S M, Ellis T, Rauscher J, Jessop P G. Liquid polymers as solvents for catalytic reductions. Green Chemistry, 2006, 8(9): 807–815
|
28 |
Gourgouillon D, Avelino H J, Fareleira J, Ponte M N. Simultaneous viscosity and density measurement of supercritical CO2-satureted PEG 400. Journal of Supercritical Fluids, 1998, 13(1–3): 177–185
|
29 |
Harrison K L, Johnston K P, Sanchez I C. Effect of surfactants on the interfacial tension between supercritical carbonate dioxide and polyethylene glocol. Langmuir, 1996, 12(11): 2637–2644
|
30 |
Dariva C, Coelho L A F, Oliveira J V. A kinetic approach for predicting diffusivities in dense fluid mixtures. Fluid Phase Equilibria, 1999, 158–160(b): 1045–1054
|
31 |
Kawanami H, Sasaki A, Matsui K, Ikushima Y. A rapid and effective synthesis of propylene carbonate using a supercritical CO2-ionic liquid system. Chemical Communications, 2003, 7(7): 896–897
|
32 |
Nomura R, Kimura M, Teshima S, Ninagawa A, Matsuda H. Directsynthesis of cyclic carbonates in the presence of organometallic compounds. Catalyses by systems from IVA, VA, and VIA group compounds and Lewis base. Bulletin of the Chemical Society of Japan, 1982, 55(10): 3200–3203
|
33 |
Udayakumar S, Lee M K, Shim H L, Park D W. Functionalization of organic ions on hybrid MCM-41 for cycloaddition reaction: the effective conversion of carbon dioxide. Applied Catalysis A: General, 2009, 365(1): 88–95
|
34 |
Udayakumar S, Park S W, Park D W, Choi B S. Immobilization of ionic liquid on hybrid MCM-41 system for the chemical fixation of carbon dioxide on cyclic carbonate. Catalysis Communications, 2008, 9(7): 1563–1570
|
35 |
Zhu A L, Jiang T, Han B X, Zhang J C, Xie Y, Ma X M. Supported choline chloride/urea as a heterogeneous catalyst for chemical fixation of carbon dioxide to cyclic carbonates. Green Chemistry, 2007, 9(2): 169–172
|
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