Abstract
Various zinc halide-based ionic liquids were prepared from zinc halides and onium halides as catalysts for the synthesis of styrene carbonate (SC) from styrene oxide and carbon dioxide. The effects of the ionic liquid catalyst composition (types of onium cation and halide, onium cation/zinc ratio) and CO2 pressure on the reaction were investigated. The effectiveness of the onium cation as the active catalyst component was in the order of tetrabutylammonium > 1-butylpyridinium > 1-butyl-3-methylimidazolium ≫ choline. The type of halide atom originating from the zinc salt affected the catalytic activity of the ionic liquid more significantly than that of the one originating from the onium salt. The onium cation/zinc ratio also affected the SC yield, but its manner was different depending on the type of onium cation. Influence of CO2 pressure was not significant.
Graphical Abstract
Various zinc halide-based ionic liquids were prepared from zinc halides and onium halides as catalysts for the synthesis of styrene carbonate from styrene oxide and CO2. Effects of types of onium cations and halides, the molar ratio of onium cation to zinc, and CO2 pressure on the carbonate yield were investigated.
Similar content being viewed by others
References
Shaikh AAG, Sivaram S (1996) Chem Rev 96:951
Xiaoding X, Moulijn JA (1996) Energy Fuels 10:305
Weissermel K, Arpe HJ (1997) Industrial organic chemistry. VCH, Weinheim
Darensbourg DJ, Holtcamp MW (1996) Coord Chem Rev 153:155
Shi M, Shen YM (2003) Curr Org Chem 7:737
Fujita S, Arai M (2005) J Jpn Petrol Inst 48:67
Sun J, Fujita S, Arai M (2005) J Organometal Chem 690:3490
Omae I (2006) Catal Today 115:33
Sakakura T, Choi J, Yasuda H (2007) Chem Rev 107:2365
Sakakura T, Khono K (2009) Chem Commun 1312
Kim HS, Kim JJ, Le BG, Jung OS, Jang HG, Kang SO (2000) Angew Chem Int Ed 39:4096
Shen YM, Duan WL, Shi M (2003) J Org Chem 68:1559
Kim HS, Kim JJ, Le SD, Lah MS, Moon D, Jang HG (2003) Chem Eur J 9:678
Palgunadi J, Lwon OS, Lee H, Bae JY, Ahn BS, Min NY, Kim HS (2004) Catal Today 98:511
Ramin M, Grunwaldt JD, Baiker A (2005) J Catal 234:256
Ramin M, Grunwaldt JD, Baiker A (2006) Appl Catal A Gen 305:46
Ion A, Parvulescu V, Jacob P, de Dos D (2009) Appl Catal A Gen 363:40
Qiao K, Ono F, Bao Q, Tomida D, Yokoyama C (2009) J Mol Catal A Chem 303:30
Dümler W, Kisch H (1990) Chem Ber 123:277
Sun J, Fujita S, Zhao F, Arai M (2004) Green Chem 6:613
Sanker M, Tarte NH, Manikandan P (2004) Appl Catal A Gen 276:217
Mori K, Mitani Y, Hara T, Mizugaki T, Ebitani K, Kaneda K (2005) Chem Commun 3331
Sun J, Fujita S, Zhao F, Arai M (2005) Appl Catal A Gen 287:221
Xiao LF, Li FW, Xia CG (2005) Appl Catal A Gen 279:125
Xie H, Li S, Zhang S (2006) J Mol Catal A Chem 250:30
Xiao LF, Li FW, Peng JJ, Xia CG (2006) J Mol Catal A Chem 253:265
Sun J, Wang L, Zhang S, Li Z, Zhang X, Dai W, Mori R (2006) J Mol Catal A Chem 256:295
Ramin M, Van Vegten N, Grunwaldt JD, Baiker A (2006) J Mol Catal A Chem 258:165
Ono F, Qiao K, Tomida D, Yokoyama C (2007) J Mol Catal A Chem 263:223
Lee EH, Ahn JY, Dharman MM, Park DW, Park SW, Kim I (2008) Catal Today 131:130
Wu SS, Zhang XW, Dai WL, Yin SF, Li WS, Ren YQ, Au CT (2008) Appl Catal A Gen 341:106
Sun J, Ren J, Zhang S, Cheng W (2009) Tetrahedron Lett 50:423
Srivastva R, Fujita S, Arai M (2009) React Kinet Catal Lett 96:55
Paddock RL, Nguyen ST (2001) J Am Chem Soc 123:11498
Shen YM, Duan WL, Shi M (2003) Adv Synth Catal 345:337
Kossev K, Koseva N, Troev K (2003) J Mol Catal A Chem 194:29
Tsuda T, Sanada S, Ueda K, Saegusa T (1976) Inorg Chem 15:2329
Aida T, Inoue S (1983) J Am Chem Soc 105:1304
Darensburg DJ, Holtcamp MW, Struck GE, Zimmer MS, Niezgoda SA, Rainey P, Robertson JB, Draper JD, Reibenspies JH (1999) J Am Chem Soc 121:107
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Fujita, Si., Nishiura, M. & Arai, M. Synthesis of Styrene Carbonate from Carbon Dioxide and Styrene Oxide with Various Zinc Halide-Based Ionic Liquids. Catal Lett 135, 263–268 (2010). https://doi.org/10.1007/s10562-010-0286-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-010-0286-3