Polyethylene glycol-supported ionic liquid as a highly efficient catalyst for the synthesis of propylene carbonate under mild conditions

Rui YAO, Hua WANG, Jinyu HAN

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PDF(291 KB)
Front. Chem. Sci. Eng. ›› 2012, Vol. 6 ›› Issue (3) : 239-245. DOI: 10.1007/s11705-012-1297-y
RESEARCH ARTICLE
RESEARCH ARTICLE

Polyethylene glycol-supported ionic liquid as a highly efficient catalyst for the synthesis of propylene carbonate under mild conditions

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Abstract

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.

Keywords

ionic liquid / PEG-supported ionic liquid / carbon dioxide / propylene carbonate

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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. Front Chem Sci Eng, 2012, 6(3): 239‒245 https://doi.org/10.1007/s11705-012-1297-y

References

[1]
Sakakura T, Choi J C, Yasuda H. Transformation of carbon dioxide. Chemical Reviews, 2007, 107(6): 2365–2387
CrossRef Pubmed Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar
[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
CrossRef Pubmed Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar
[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
CrossRef Pubmed Google scholar
[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
CrossRef Google scholar
[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
CrossRef Pubmed Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar
[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
CrossRef Pubmed Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar
[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
CrossRef Pubmed Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar
[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
CrossRef Pubmed Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar
[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
CrossRef Google scholar

Acknowledgments

The work was supported by the National Natural Science Foundation of China (Grant No. 21076152), the Special Research Fund for the Doctoral Program of Higher Education of China (No. 2100032110018) and the Program of Introducing Talents of Discipline to Universities, China (No. B06006).

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