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Transesterification Between Diphenyl Carbonate and 1,4-Butanediol to Polycarbonate Diol Catalyzed by Various Metal Acetylacetonates
Corresponding Author(s) : Liping Wang
Asian Journal of Chemistry,
Vol. 27 No. 8 (2015): Vol 27 Issue 8
Abstract
The catalytic activities of various metal acetylacetonates for the synthesis of polycarbonate diol via transesterification between diphenyl carbonate and 1,4-butanediol were investigated. Their catalytic activities in the esterification process is monitored by measuring the amount of phenol generated and the number average molecular weight Mn and the hydroxyl value of polycarbonate diol are used as the index in polycondensation process. Zn(acac)2 and Al(acac)3 exhibited higher catalytic activities for transesterification between diphenyl carbonate and 1,4-butanediol. Under the optimal reaction conditions, polycarbonate diol with the Mn over 2300 and the hydroxyl value below 48.2 mg KOH/g was prepared. X-ray diffraction result shows that polycarbonate diol is a semi-crystalline and the degree of crystallinity is 73.4 %.
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- L.A. Matheson, R.S. Labow and J.P. Santerre, J. Biomed. Mater. Res., 61, 505 (2002); doi:10.1002/jbm.10286.
- H. Schnell, Chemistry and Physics of Polycarbonates, Wiley, New York, p. 9 (1964).
- H. Hocker and H. Heul, in ed.: J.C. Salomone, Cyclic Carbonates (Ring-Opening Polymerization), Polymeric Materials Encyclopedia, CRC Press, Boca Raton, Florida, p. 16 (1996).
- A. Rokicki and W. Kuran, J. Macromol. Sci. Rev. Macromol. Chem. C, 21, 135 (1981).
- Y.X. Feng, N. Yin, Q.F. Li, J.W. Wang, M.Q. Kang and X.K. Wang, Ind. Eng. Chem. Res., 47, 2140 (2008); doi:10.1021/ie070759k.
- H. Steffen, B. Rolf and B. Lotar, US Patent 20050065360 (2005).
- X.Y. Xie, J.H. Li, C.S. He, C.R. Fan and Y.P. Zhong, Polym. Mater. Sci. Eng., 18, 169 (2002).
- J. Tillack and J. Laue, WO Patent 03002630A3 (2003).
- H.J. Buysch and H. Krimm, DE Patent 2523352A1 (1976).
- T. Murai and T. Fujii, EP Patent 0343572A2 (1989).
- P. Cao, W.B. Shi, X.G. Yang, T. Kang, Y. Ch Lei and G.Y. Wang, Petrochem. Tech., 3, 346 (2010).
- S.T. Chen and Y.L. Hu, Petrochem. Tech., 6, 896 (2006).
- K. Tomita and H. Ida, Polymer, 14, 55 (1973); doi:10.1016/0032-3861(73)90096-7.
- Y.H. Zhang, Inorg. Chem., 21, 3889 (1982); doi:10.1021/ic00141a006.
- D.N. Ye, D.S. Ai and R.S. Zen, Sci. China Series B Chem., 9, 303 (1999).
- F.A. Cotton, G. Wilkinson, C.A. Murillo and B. Manfred, Advanced Inorganic Chemistry, Wiley-Interscience New York, edn. 6, p. 168 (1999).
References
L.A. Matheson, R.S. Labow and J.P. Santerre, J. Biomed. Mater. Res., 61, 505 (2002); doi:10.1002/jbm.10286.
H. Schnell, Chemistry and Physics of Polycarbonates, Wiley, New York, p. 9 (1964).
H. Hocker and H. Heul, in ed.: J.C. Salomone, Cyclic Carbonates (Ring-Opening Polymerization), Polymeric Materials Encyclopedia, CRC Press, Boca Raton, Florida, p. 16 (1996).
A. Rokicki and W. Kuran, J. Macromol. Sci. Rev. Macromol. Chem. C, 21, 135 (1981).
Y.X. Feng, N. Yin, Q.F. Li, J.W. Wang, M.Q. Kang and X.K. Wang, Ind. Eng. Chem. Res., 47, 2140 (2008); doi:10.1021/ie070759k.
H. Steffen, B. Rolf and B. Lotar, US Patent 20050065360 (2005).
X.Y. Xie, J.H. Li, C.S. He, C.R. Fan and Y.P. Zhong, Polym. Mater. Sci. Eng., 18, 169 (2002).
J. Tillack and J. Laue, WO Patent 03002630A3 (2003).
H.J. Buysch and H. Krimm, DE Patent 2523352A1 (1976).
T. Murai and T. Fujii, EP Patent 0343572A2 (1989).
P. Cao, W.B. Shi, X.G. Yang, T. Kang, Y. Ch Lei and G.Y. Wang, Petrochem. Tech., 3, 346 (2010).
S.T. Chen and Y.L. Hu, Petrochem. Tech., 6, 896 (2006).
K. Tomita and H. Ida, Polymer, 14, 55 (1973); doi:10.1016/0032-3861(73)90096-7.
Y.H. Zhang, Inorg. Chem., 21, 3889 (1982); doi:10.1021/ic00141a006.
D.N. Ye, D.S. Ai and R.S. Zen, Sci. China Series B Chem., 9, 303 (1999).
F.A. Cotton, G. Wilkinson, C.A. Murillo and B. Manfred, Advanced Inorganic Chemistry, Wiley-Interscience New York, edn. 6, p. 168 (1999).