Abstract
A novel Schiff base complex BCED–Zn has been found to be an effective catalyst for copolymerization of CO2 and cyclohexene oxide to afford alternating copolymer poly(cyclohexenylene carbonate) (PCHC), and the turnover number was up to 421.1 at 110°C and 4 MPa CO2 pressure for 24 h. The influence of the reaction conditions such as reaction time, reaction temperature and CO2 pressure was discussed and optimized. The thermal stability of PCHC was measured by thermogravimetric analysis, indicating that the 5 % weight loss temperature was about 232 °C and the maximum weight loss temperature was around 256 °C.
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References
Li H.C., Niu Y.S.: Synthesis of biodegradable polycarbonate by alternating copolymerization of carbon dioxide and propylene oxide using a cobalt/Schiff base catalyst. React. Funct. Polym. 71(2), 121–125 (2011)
Arakawa H., Aresta M., Armor J.N.: Catalysis research of relevance to carbon management: progress, challenges, and opportunities. Chem. Rev. 101(4), 953–996 (2001)
Zhang X.H., Wei R.J., Sun X.K., Zhang J.F., Du B.Y., Fan Z.Q., Qi G.R.: Selective copolymerization of carbon dioxide with propylene oxide catalyzed by a nanolamellar double metal cyanide complex catalyst at low polymerization temperatures. Polymer 52, 5494–5502 (2011)
Nakano K., Kobayashi K., Ohkawara T., Imoto H., Nozaki K.: Copolymerization of epoxides with carbon dioxide catalyzed by iron–corrole complexes: synthesis of a crystalline copolymer. J. Am. Chem. Soc. 135(23), 8456–8459 (2013)
Ikpo N., Flogeras J.C., Kerton F.M.: Aluminium coordination complexes in copolymerization reactions of carbon dioxide and epoxides. Dalton Trans. 42(25), 8998–9006 (2013)
Inoue S., Kitamura K., Tsuruta T.: Copolymerization of carbon dioxide and epoxide. J. Polym. Sci. B Polym. Lett. 7, 287–292 (1969)
Yu K.Q., Jones C.W.: Silica-immobilized zinc β-diiminate catalysts for the copolymerization of epoxides and carbon dioxide. Organometallics 22, 2571–2580 (2003)
Duan Z.Y., Wang X.Y., Gao Q., Zhang L., Liu B.Y., Kim I.: Highly active bifunctional cobalt-salen complexes for the synthesis of poly(ester-block-carbonate) copolymer via terpolymerization of carbon dioxide, propylene oxide, and norbornene anhydride isomer: roles of anhydride conformation consideration. J. Polym. Sci. A Polym. Chem. 52(6), 789–795 (2014)
Kim I., Kim S.M., Kim J.S., Son G.W., Park D.W., Ha C.S.: Synthesis and alternating copolymerizations of carbon dioxide with cyclohexene oxide over (6-MepyCAr2O)Zn(OAc) complexes containing bidentate pyridine-alkoxide ligands. Prepr. Pap. Am. Chem. Soc. Div. Fuel Chem. 49(1), 11–12 (2004)
Sugimoto H., Ohshima H., Inoue S.: Alternating copolymerization of carbon dioxide and epoxide by manganese porphyrin: the first example of polycarbonate synthesis from 1-atm carbon dioxide. J. Polym. Sci. A Polym. Chem. 41(22), 3549–3555 (2003)
Darensbourg D.J., Wildeson J.R., Yarbrough J.C.: Bis 2,6-difluorophenoxide dimeric complexes of Zinc and cadmium and their phosphine adducts: lessons learned relative to carbon dioxide/cyclohexene oxide alternating copolymerization processes catalyzed by zinc phenoxides. J. Am. Chem. Soc. 122(50), 12487–12496 (2000)
Jeon J.Y., Eo S.C., Varghese J.Y., Lee B.Y.: Copolymerization and terpolymerization of carbon dioxide/propylene oxide/phthalic anhydride using a (salen)Co(III) complex tethering four quaternary ammonium salts. Beilstein J. Org. Chem. 10, 1787–1795 (2014)
Moore D.R., Cheng M., Lobkovsky E.B., Coates G.W.: Mechanism of the alternating copolymerization of epoxides and CO 2 using beta-diiminate zinc catalysts: evidence for a bimetallic epoxide enchainment. J. Am. Chem. Soc. 125(39), 11911–11924 (2003)
Sakakura T., Choi J.C., Yasuda H.: Transformation of carbon dioxide. Chem. Rev. 107, 2365–2387 (2007)
Wang J., Shan X.F., Shan S.Y., Su H.Y., Wu S.S., Jia Q.M.: A novel supported salenCrIIICl catalyst for alternating copolymerization of cyclohexene oxide with carbon dioxide. Catal. Commun. 59, 116–121 (2015)
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Based on 10th International Conference on Novel Materials and their Synthesis (NMS) – China.
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Fan, L., Qin, G. & Cao, S. Synthesis of Polycarbonates by Copolymerization of Carbon Dioxide and Cyclohexene Oxide Using Schiff Base Complex as Catalyst. Arab J Sci Eng 40, 2861–2866 (2015). https://doi.org/10.1007/s13369-015-1667-0
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DOI: https://doi.org/10.1007/s13369-015-1667-0