Cationic organobismuth complex as an effective catalyst for conversion of CO<sub>2</sub> into cyclic carbonates

doi:10.1007/s11783-008-0068-y

Front Envir Sci Eng Chin

2009, Vol. 3

Issue (1) : 32-37 https://doi.org/10.1007/s11783-008-0068-y

Research article

Cationic organobismuth complex as an effective catalyst for conversion of CO₂ into cyclic carbonates

Xiaowen ZHANG¹, Weili DAI¹, Shuangfeng YIN¹(

), Shenglian LUO¹(

), Chak-Tong AU²

1. College of Chemistry and Chemical Engineering, Hunan University; 2. Department of Chemistry, Hong Kong Baptist University

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Abstract

In order to achieve high-efficiency conversion of CO₂ into valuable chemicals, and to exploit new applications of organobismuth compounds, cationic organobismuth complex with 5,6,7,12-tetrahydrodibenz[c,f]1^,5 azabismocine framework was examined for the first time for the coupling of CO₂ into cyclic carbonates, using terminal epoxides as substrates and tetrabutylammonium halide as co-catalyst in a solvent-free environment under mild conditions. It is shown that the catalyst exhibited high activity and selectivity for the coupling reaction of CO₂ with a wide range of terminal epoxide. The selectivity of propylene carbonates could reach 100%, and the maximum turnover frequency was up to 10740 h^-1 at 120°C and 3 MPa CO₂ pressure when tetrabutylammonium iodide was used as co-catalyst. Moreover, the catalyst is environment friendly, resistant to air and water, and can be readily reused and recycled without any loss of activity, demonstrating a potential in industrial application.

Keywords cationic organobismuth complex terminal epoxide carbon dioxide coupling cyclic carbonate

Corresponding Author(s): YIN Shuangfeng,Email:sf_yin@hnu.cn; sllou@hnu.cn; LUO Shenglian,Email:sf_yin@hnu.cn; sllou@hnu.cn

Issue Date: 05 March 2009

Cite this article:

Xiaowen ZHANG,Weili DAI,Shuangfeng YIN, et al. Cationic organobismuth complex as an effective catalyst for conversion of CO₂ into cyclic carbonates[J]. Front Envir Sci Eng Chin, 2009, 3(1): 32-37.

URL:

https://academic.hep.com.cn/fese/EN/10.1007/s11783-008-0068-y
https://academic.hep.com.cn/fese/EN/Y2009/V3/I1/32

Fig0

Tab0 Catalytic performance of Catalysts

1	SakakuraT, ChoiJ C, YasudaH. Transformation of carbon dioxide. Chem. Rev. , 2007, 107(6): 2365–2387 doi: 10.1021/cr068357u
2	YangH, XuZ, FanM, GuptaR, SlimaneR B, BlandA E, WrightI. Progress in carbon dioxide separation and capture: A review. J. Environ. Sci. , 2008, 20(1): 14–27 doi: 10.1016/S1001-0742(08)60002-9
3	KasugaK, KabataN. The fixation of carbon dioxide with 1,2-epoxypropane catalyzed by alkali-metal halide in the presence of a crown ether. Inorg. Chim. Acta , 1997, 257(2): 277–278 doi: 10.1016/S0020-1693(96)05481-3
4	LuX B, ZhangY J, JinK, LuoL M, WangH. Highly active electrophile-nucleophile catalyst system for the cycloaddition of CO₂ to epoxides at ambient temperature. J. Catal. , 2004, 227(2): 537–541 doi: 10.1016/j.jcat.2004.07.018
5	JingH, NguyenS T. SnCl₄-organic base: Highly efficient catalyst system for coupling reaction of CO₂ and epoxides. J. Mol. Catal. A , 2007, 261(1): 12–15 doi: 10.1016/j.molcata.2006.07.057
6	KimH S, KimJ J, KimH, JangH G. Imidazolium zinc tetrahalide-catalyzed coupling reaction of CO₂ and ethylene oxide or propylene oxide. J. Catal. , 2003, 220(1): 44–46 doi: 10.1016/S0021-9517(03)00238-0
7	LiF, XiaoL, XiaC, HuB. Chemical fixation of CO₂ with highly efficient ZnCl₂/[BMIm]Br catalyst system. Tetrahedron Lett. , 2004, 45(45): 8307–8310 doi: 10.1016/j.tetlet.2004.09.074
8	SunJ, FujitaS, ZhaoF, AraiM. Synthesis of styrene carbonate from styrene oxide and carbon dioxide in the presence of zinc bromide and ionic liquid under mild conditions. Green Chem. , 2004, 6(12): 613–616 doi: 10.1039/b413229g
9	XiaoL F, LiF W, PengJ J, XiaC G. Immobilized ionic liquid/zinc chloride: Heterogeneous catalyst for synthesis of cyclic carbonates from carbon dioxide and epoxides. J. Mol. Catal. A , 2006, 253(1–2): 265–269
10	XiaoL F, LiF W, XiaC G. An easily recoverable and efficient natural biopolymer-supported zinc chloride catalyst system for the chemical fixation of carbon dioxide to cyclic carbonate. Appl. Catal. A , 2005, 279(1–2): 125–129
11	KimY J, VarmaR S. Tetrahaloindate(III)-based ionic liquids in the coupling reaction of carbon dioxide and epoxides to generate cyclic carbonates: H-bonding and mechanistic studies. J. Org. Chem. , 2005, 70(20): 7882–7891 doi: 10.1021/jo050699x
12	ZhaoY, TianJ S, QiX H, HanZ N, ZhuangY Y, HeL N. Quaternary ammonium salt-functionalized chitosan: An easily recyclable catalyst for efficient synthesis of cyclic carbonates from epoxides and carbon dioxide. J. Mol. Catal. A , 2007, 271(1–2): 284–289
13	LuX B, ZhangY J, LiangB, LiX, WangH. Chemical fixation of carbon dioxide to cyclic carbonates under extremely mild conditions with highly active bifunctional catalysts. J. Mol. Catal. A , 2004, 210(1–2): 31–34
14	LuX B, HeR, BaiC X. Synthesis of ethylene carbonate from supercritical carbon dioxide/ethylene oxide mixture in the presence of bifunctional catalyst. J. Mol. Catal. A , 2002, 186(1–2): 1–11
15	SunJ M, FujitaS I, ZhaoF Y, AraiM. A highly efficient catalyst system of ZnBr₂/n-Bu₄NI for the synthesis of styrene carbonate from styrene oxide and supercritical carbon dioxide. Appl. Catal. A , 2005, 287(2): 221–226 doi: 10.1016/j.apcata.2005.03.035
16	OnoF, QiaoK, TomidaD, YokoyamaC. Rapid synthesis of cyclic carbonates from CO₂ and epoxides under microwave irradiation with controlled temperature and pressure. J. Mol. Catal. A , 2007, 263(1–2): 223–226
17	XieH, LiS, ZhangS. Highly active, hexabutylguanidinium salt/zinc bromide binary catalyst for the coupling reaction of carbon dioxide and epoxides. J. Mol. Catal. A , 2006, 250(1–2): 30–34
18	SunJ, WangL, ZhangS, LiZ, ZhangX, DaiW, MoriR. ZnCl₂/phosphonium halide: An efficient Lewis acid/base catalyst for the synthesis of cyclic carbonate. J. Mol. Catal. A , 2006, 256(1–2): 295–300
19	PaddockR L, NguyenS T. Chemical CO₂ fixation: Cr(III) salen complexes as highly efficient catalysts for the coupling of CO₂ and epoxides. J. Am. Chem. Soc. , 2001, 123(46): 11498–11499 doi: 10.1021/ja0164677
20	JutzF, GrunwaldtJ D, BaikerA. Mn(III)(salen)-catalyzed synthesis of cyclic organic carbonates from propylene and styrene oxide in “supercritical” CO₂. J. Mol. Catal. A , 2008, 279(1): 94–103 doi: 10.1016/j.molcata.2007.10.010
21	BuZ, QinG, CaoS. A ruthenium complex exhibiting high catalytic efficiency for the formation of propylene carbonate from carbon dioxide. J. Mol. Catal. A , 2007, 277(1–2): 35–39
22	SuzukiH, MatanoY. Organobismuth Chemistry. Amsterdam: Elsevier, 2001
23	GagnonA, St-OngeM, LittleK, DuplessisM, BarabeìF. Direct N-cyclopropylation of cyclic amides and azoles employing a cyclopropylbismuth reagent. J. Am. Chem. Soc. , 2007, 129(1): 44–45 doi: 10.1021/ja0676758
24	WuS S, DaiW L, YinS F, LiW S, AuC T. Bismuth subnitrate as an efficient heterogeneous catalyst for acetalization and ketalization of carbonyl compounds with diols. Catal. Lett. , 2008, 124(1–2): 127–132 doi: 10.1007/s10562-008-9435-3
25	BaoM, HayashiT, ShimadaS. Cationic organobismuth complex with 5,6,7,12-tetrahydrodibenz[c,f][1,5]azabismocine framework and its coordination complexes with neutral molecules. Organometallics , 2007, 26(7): 1816–1822 doi: 10.1021/om0611453

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