Abstract
A catalyst system for the efficient two-step coupling of CO2 and styrene to styrene carbonate was developed. Gold nanoparticles immobilized on multi-walled carbon nanotubes (Au/CNT) of 6 nm in diameter were used as a catalyst for the epoxidation step. The process was carried out at 80 °C for 4 h in the presence of anhydrous tert-butyl hydroperoxide as an oxidant. The reaction of the resulting epoxide and CO2 was catalyzed by the 1-butyl-3-methylimidazolium bromide [bmim]Br-ZnBr2 system under the CO2 pressure (1.2 MPa) at 120 °C. A high styrene carbonate yield of 60 % was achieved. After the reaction, Au/CNT could be easily separated and reused without any significant loss of activity.
Graphical Abstract
Similar content being viewed by others
References
Aresta M, Dibenedetto A, Angelini A (2014) Chem Rev 114:1709
Sakakura T, Choi J-C, Yasuda H (2007) Chem Rev 107:2365
Song C (2006) Catal Today 115:2
North M, Pasquale R, Young C (2010) Green Chem 12:1514
Hargrove GL, Maruvada S (2014) US Patent 2014/0331727 A1
Gan H, Takeuchi ES (1998) US Patent 5753389 A
Sun J, Yao X, Cheng W, Zhang S (2014) Green Chem 16:3297
Lombardo VM, Dhulst EA, Leitsch EK, Wilmot N, Heath WH, Gies AP, Miller MD, Torkelson JM, Scheidt KA (2015) Eur J Org Chem 2015:2791
Sun J, Liang L, Sun J, Jiang Y, Lin K, Xu X, Wang R (2011) Catal Surv Asia 15:49
Aresta M, Dibenedetto A (2002) J Mol Catal Chem 182–183:399
Sun J, Fujita S, Bhanage BM, Arai M (2004) Catal Today 93–95:383
Bai D, Jing H (2010) Green Chem 12:39
Eghbali N, Li C-J (2007) Green Chem 9:213
Wang J-L, Wang J-Q, He L-N, Dou X-Y, Wu F (2008) Green Chem 10:1218
Xiang D, Liu X, Sun J, Xiao F-S, Sun J (2009) Catal Today 148:383
Chen F, Dong T, Xu T, Li X, Hu C (2011) Green Chem 13:2518
Ono F, Qiao K, Tomida D, Yokoyama C (2007) Appl Catal A Gen 333:107
Carvalho Rocha C, Onfroy T, Launay F (2015) CR Chimie 18:270
Peng L, Zhang J, Yang S, Han B, Sang X, Liu C, Ma X, Yang G (2015) Chem Commun 51:4398
Jin Y, Zhuang D, Yu N, Zhao H, Ding Y, Qin L, Liu J, Yin D, Qiu H, Fu Z, Yin D (2009) Microporous Mesoporous Mater 126:159
Jin Y, Wang P, Yin D, Liu J, Qiu H, Yu N (2008) Microporous Mesoporous Mater 111:569
Wang F, Liu C, Liu G, Liu J (2015) J Porous Mater 22:1423
Liu J, Wang F, Xu T, Gu Z (2010) Catal Lett 134:51
Sun J, Fujita S, Zhao F, Hasegawa M, Arai M (2005) J Catal 230:398
Wang Y, Sun J, Xiang D, Wang L, Sun J, Xiao F-S (2009) Catal Lett 129:437
Lancaster NL, Salter PA, Welton T, Young GB (2002) J Org Chem 67:8855
Liu HR, Yu HW, Zhou EP, Zhang XH, Zhang XC (2013) Asian J Chem 25:8266
Peng X, Chen J, Misewich JA, Wong SS (2009) Chem Soc Rev 38:1076
Li B, He P, Yi G, Lin H, Yuan Y (2009) Catal Lett 133:33
Haruta M (1997) Catal Today 36:153
He Q, O’Brien JW, Kitselman KA, Tompkins LE, Curtis GCT, Kerton FM (2014) Catal Sci Technol 4:1513
Shim J-J, Kim D, Ra CS (2006) Bull Korean Chem Soc 27:744
Li F, Xiao L, Xia C, Hu B (2004) Tetrahedron Lett 45:8307
Bawaked S, Dummer NF, Bethell D, Knight DW, Hutchings GJ (2011) Green Chem 13:127
Paul S, Zhu Y, Romain C, Brooks R, Saini PK, Williams CK (2015) Chem Commun 51:6459
Acknowledgments
This work was supported by the Polish National Science Centre (NCN); Decision No.: 2011/03/B/ST8/06178. Co-author of this paper, Katarzyna Jasiak, is a scholar under the project “DoktoRIS—Scholarship Programme for Innovative Silesia” co-financed by the European Union under the European Social Fund.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Jasiak, K., Krawczyk, T., Pawlyta, M. et al. One-Pot Synthesis of Styrene Carbonate from Styrene and CO2 Over the Nanogold-Ionic Liquid Catalyst. Catal Lett 146, 893–901 (2016). https://doi.org/10.1007/s10562-016-1703-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-016-1703-z