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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Synthesis of Diphenyl Carbonate from Carbon Dioxide, Phenol, and Carbon Tetrachloride Catalysed by ZnCl2 Using Trifluoromethanesulfonic Acid as Functional Co-Catalyst

Guozhi Fan A B , Min Wang A , Zhenxiao Duan A , Minghai Wan A and Tao Fang A
+ Author Affiliations
- Author Affiliations

A School of Chemical and Environmental Engineering, Wuhan Polytechnic University, Wuhan 430023, P. R. China.

B Corresponding author. Email: fgzcch@whpu.edu.cn

Australian Journal of Chemistry 65(12) 1667-1673 https://doi.org/10.1071/CH12115
Submitted: 24 February 2012  Accepted: 24 August 2012   Published: 24 September 2012

Abstract

Diphenyl carbonate (DPC) was synthesised from carbon dioxide, phenol, and carbon tetrachloride catalysed by the Lewis acid ZnCl2 with the addition of co-catalyst. It was found that common bases are not effective co-catalysts for the production of DPC, and only slight enhancement in the catalytic activity of ZnCl2 was observed in the presence of inorganic additives such as inorganic carbonates and quaternary ammonium salts. Although poor conversion of phenol and yield of DPC were obtained using ZnCl2 or trifluoromethanesulfonic acid (CF3SO3H) as the sole catalyst, the catalytic activity of ZnCl2 was significantly improved by the addition of a catalytic amount of CF3SO3H. CF3SO3H has been proven to be an effective co-catalyst. The conversion of phenol and the yield of DPC were dependent on the amount of ZnCl2 and CF3SO3H, the reaction temperature, and the pressure of CO2. A possible reaction mechanism for the synthesis of DPC catalysed by the co-catalytic system including ZnCl2 and CF3SO3H was also proposed.


References

[1]  H. Arakawa, M. Aresta, J. N. Armor, M. A. Barteau, E. J. Beckman, A. Bell, J. E. Bercaw, C. Creutz, E. Dinjus, D. A. Dixon, K. Domen, D. L. DuBois, J. Eckert, E. Fujita, D. H. Gibson, W. A. Goddard, D. W. Goodman, J. Keller, G. J. Kubas, H. H. Kung, J. E. Lyons, L. E. Manzer, T. J. Marks, K. Morokuma, K. M. Nicholas, R. Periana, L. Que, J. Rostrup-Nielson, W. M. H. Sachtler, L. D. Schmidt, A. Sen, G. A. Somorjai, P. C. Stair, B. R. Stults, W. Tumas, Chem. Rev. 2001, 101, 953.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXisFehsLg%3D&md5=fb5e6570ec715e5bc1333f8057a46c48CAS |

[2]  I. Omae, Catal. Today 2006, 115, 33.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XkvF2ksro%3D&md5=4a0c8e3aeb0c82ce483d6aaff3e78bf2CAS |

[3]  T. Sakakura, K. Kohno, Chem. Commun. 2009, 1312,
         | Crossref | GoogleScholarGoogle Scholar |

[4]  G. Centi, S. Perathoner, Catal. Today 2009, 148, 191.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsVCqs7nO&md5=f75073e804235e4c385b65caf4c5682eCAS |

[5]  S. N. Riduan, Y. Zhang, Dalton Trans. 2010, 39, 3347.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXjslWjsro%3D&md5=81cf301b46737c68aea4f93f827c5f50CAS |

[6]  H. Kawanami, A. Sasaki, K. Matsui, Y. Ikushima, Chem. Commun. 2003, 896,
         | Crossref | GoogleScholarGoogle Scholar |

[7]  J. Sun, S. Fujita, F. Zhao, M. Hasegawa, M. Arai, J. Catal. 2005, 230, 398.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhvVSktr4%3D&md5=0b478fdc9faa030ecc801e27cc9bf8a5CAS |

[8]  J. Sun, S. Fujita, F. Zhao, M. Arai, Appl. Catal. A Gen. 2005, 287, 221.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXltVOiu7o%3D&md5=19f2b664caaaeffa20508fa6bfaf135bCAS |

[9]  B. M. Bhanage, S. Fujita, Y. Ikushima, M. Arai, Green Chem. 2003, 5, 340.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXktlyqsr4%3D&md5=1523c08bc74a76907574753ad744de56CAS |

[10]  Z. Zhang, S. Hu, J. Song, W. Li, G. Yang, B. Han, ChemSusChem 2009, 2, 234.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXktFKrur0%3D&md5=1336fe73ab78a573e211fc5ef61ed83bCAS |

[11]  Z. Zhang, Y. Xie, W. Li, S. Hu, J. Song, T. Jiang, B. Han, Angew. Chem. Int. Ed. 2008, 47, 1127.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhvFSns78%3D&md5=84b50f9bcbf3afe2e2383c62728d8941CAS |

[12]  A. Correa, R. Martĺn, J. Am. Chem. Soc. 2009, 131, 15974.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht1OkurfL&md5=4344d1227730f8eb01ef9836f7fcac05CAS |

[13]  T. Iijima, T. Yamaguchi, J. Mol. Catal. Chem. 2008, 295, 52.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXht12rsrrL&md5=a98653b4d9402f5aec5cd56d7c16c855CAS |

[14]  T. Iijima, T. Yamaguchi, Appl. Catal. A Gen. 2008, 345, 12.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXnvVGgt7k%3D&md5=c5bf0cc4e4df428d85ae44bdb7c883d1CAS |

[15]  X. Miao, J. Q. Wang, W. Ying, Y. Duan, L. N. He, ChemSusChem 2008, 1, 236.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXltFOhtLc%3D&md5=58ffc1682f741e8c3e942547668449a1CAS |

[16]  W. Clegg, R. W. Harrington, M. North, R. Pasquale, Chem. – Eur. J. 2010, 16, 6828.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXnvVOku7g%3D&md5=63ed6f0fcf617fc486e09480315ed2d8CAS |

[17]  H. Sato, H. Yoshioka, Y. Izumi, J. Mol. Catal. Chem. 1999, 149, 25.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXnvVWgtb8%3D&md5=4729a8a44aa13f306bd09a8118d85ab8CAS |

[18]  J. Penzien, R. Q. Su, T. E. Müller, J. Mol. Catal. Chem. 2002, 182–183, 489.
         | Crossref | GoogleScholarGoogle Scholar |

[19]  M. van Schilt, M. Kemmere, A. Keurentjes, Catal. Today 2006, 115, 162.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XkvF2lt7Y%3D&md5=b472c02a82943754889dcd79d8301063CAS |

[20]  S. Dinda, A. V. Patwardhan, S. R. Panda, N. C. Pradhan, Chem. Eng. J. 2008, 136, 349.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhsVers7o%3D&md5=096a2eb752ddc619173745d4951c1f10CAS |

[21]  S. Udayakumar, S. W. Park, D. W. Park, B. S. Choi, Catal. Commun. 2008, 9, 1563.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXjsVShs78%3D&md5=4f9b7939de5aa4fa4c1343b877257cceCAS |

[22]  X. B. Lu, L. Shi, Y. M. Wang, R. Zhang, Y. J. Zhang, X. J. Peng, Z. C. Zhang, B. Li, J. Am. Chem. Soc. 2006, 128, 1664.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XjvV2rsw%3D%3D&md5=13f1451418a2a4371b88ad86aa94803eCAS |

[23]  K. Kohno, J. C. Choi, Y. Ohshima, H. Yasuda, T. Sakakura, ChemSusChem 2008, 1, 186.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXltFOhtL8%3D&md5=0421d71b7694e7eafffad07907f557eeCAS |

[24]  T. Sakai, Y. Tsutsumi, T. Ema, Green Chem. 2008, 10, 337.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXislSmsLY%3D&md5=a3a3771b00cca4d0ede5f07dad86d9afCAS |

[25]  W. L. Dai, S. L. Luo, S. F. Yin, C. T. Au, Appl. Catal. A Gen. 2009, 366, 2.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXpvF2nt70%3D&md5=f348985cf91f6021855ba3fd56c1fa40CAS |

[26]  J. Gong, X. Ma, S. Wang, Appl. Catal. A Gen. 2007, 316, 1.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xht1WltL3E&md5=e246e246c83f6cd01aa9ccac17bec24bCAS |

[27]  I. Hatanaka, N. Mitsuyasu, G. Yin, Y. Fujiwara, T. Kitamura, K. Kusakabe, T. Yamaji, J. Organomet. Chem. 2003, 674, 96.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXjs1Cgsrw%3D&md5=2dd975d84be17c2ab23e9e207f53fd5dCAS |

[28]  H. Naeimi, L. Moradi, J. Mol. Catal. Chem. 2006, 256, 242.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XoslGmtrY%3D&md5=ea67d607268f6e7ef4036f69baf0dc85CAS |

[29]  G. A. Olah, B. Török, J. P. Joschek, I. Bucsi, P. M. Esteves, G. Rasul, G. K. S. Prakash, J. Am. Chem. Soc. 2002, 124, 11379.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XmsFGmur8%3D&md5=0eca28e4161f79a63e9053989a61ce92CAS |

[30]  Z. Li, Z. Qin, J. Mol. Catal. Chem. 2007, 264, 255.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXit12ltb8%3D&md5=b7c16698106231d5d0e7825e66ea36c3CAS |

[31]  K. Su, Z. Li, B. Cheng, Y. Ren, Catal. Commun. 2008, 9, 1666.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXjsVShsb4%3D&md5=790ca027a094e64dea079af5eed49f6aCAS |

[32]  Z. Li, Z. Qin, H. Zhu, J. Wang, Chem. Lett. 2006, 35, 784.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XnsVyhsrc%3D&md5=e39b1fc3cb9b870a2bb0bc4c954a1659CAS |

[33]  G. Z. Fan, S. I. Fujita, B. Zou, N. Masahiro, X. C. Meng, M. Arai, Catal. Lett. 2009, 133, 280.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsVagsL%2FP&md5=7df72f96ecde1ddcd5917a34ec0163dbCAS |

[34]  G. Z. Fan, Z. G. Wang, B. Zou, M. Wang, Fuel Process. Technol. 2011, 92, 1052.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXisVOisL8%3D&md5=4a22aea1d15120ab7168d5fe8751bde3CAS |

[35]  G. Z. Fan, H. T. Zhao, Z. X. Duan, T. Fang, M. H. Wan, L. N. He, Catal. Sci. Technol 2011, 1, 1138.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtFymtLbK&md5=3a001c8fd77112496c62f32c9f717e8cCAS |

[36]  Y. Tae Kim, E. D. Park, Appl. Catal. A Gen. 2009, 361, 26.
         | Crossref | GoogleScholarGoogle Scholar |

[37]  G. Z. Fan, T. Li, G. X. Li, D. J. Zhu, Chin. J. Catal. 2005, 26, 625.
         | 1:CAS:528:DC%2BD2MXhtVersbfN&md5=78dfabe262e90a0702fd64caabbd9a6eCAS |

[38]  G. Z. Fan, J. Huang, Z. Q. Li, T. Li, G. X. Li, J. Mol. Catal. Chem. 2007, 267, 34.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXjsVOisLY%3D&md5=dd48a1388f6aabd33c66443e5027378bCAS |

[39]  G. Z. Fan, T. Li, G. X. Li, Appl. Organomet. Chem. 2006, 20, 656.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtVKgurfF&md5=c1180318f4fea7457d344c0ecaed0d38CAS |

[40]  M. Chatterjee, Y. Ikushima, F. Zhao, New J. Chem. 2003, 27, 510.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhsV2ktrY%3D&md5=7d674a1118eb9b48747858af95bacb9eCAS |

[41]  A. A. Clifford, K. Pople, W. J. Gaskill, K. D. Bartle, C. M. Rayner, J. Chem. Soc., Faraday Trans. 1998, 94, 1451.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXjtVagsb0%3D&md5=2f4aa5a2980ae45ae571f0d4fa4b8200CAS |

[42]  F. Zhao, R. Zhang, M. Chatterjee, M. Ikushima, M. Arai, Adv. Synth. Catal. 2004, 346, 661.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXlt1Ojtrk%3D&md5=b329baecab7c489703ebf2a04d137a47CAS |

[43]  Y. Kayaki, T. Suzuki, T. Ikariya, Chem. Asian J. 2008, 3, 1865.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXht1GksLrO&md5=9633fcffc904e4d81f1fb050b593b022CAS |

[44]  S. Ravipaty, A. G. Sclafani, B. R. Fonslow, D. J. Chesney, J. Chem. Eng. Data 2006, 51, 1310.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XmtFGls7s%3D&md5=a98f1747aa704f0efb123a9f7754af8aCAS |

[45]  J. García-González, M. J. Molina, F. Rodríguez, F. Mirada, J. Chem. Eng. Data 2001, 46, 918.
         | Crossref | GoogleScholarGoogle Scholar |

[46]  Y. Xiao, Y. X. Wu, C. W. Wan, W. Y Ying, Acta Petrol. Sin. (Petrol. Process. Sect.) 2009, 25, 407.
         | 1:CAS:528:DC%2BD1MXovVKmtb0%3D&md5=296ae16e32036f6f0982ab5050fb0189CAS |

[47]  Y. Kosugi, K. Takahashi, Y. Imaoka, J. Chem. Res. (S) 1999, 114,
         | Crossref | GoogleScholarGoogle Scholar |

[48]  F. Wessely, K. Benedict, H. Benger, G. Friedrich, F. Prilinger, Monatsh. Chem. 1950, 81, 1071.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG3MXksVakuw%3D%3D&md5=2b7f25e25d8b7e1324d586234b8ef81fCAS |

[49]  Y. Kosugi, Y. Imaoka, F. Gotoh, M. A. Rahim, Y. Matsuid, K. Sakanishi, Org. Biomol. Chem. 2003, 1, 817.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXjt1Ggtbc%3D&md5=b97013b4919c6c416d3f62ff23f90e7bCAS |

[50]  P. Van der Avert, S. G. Podkolzin, O. Manoilova, H. D. Winne, B. M. Weckhuysen, Chem. – Eur. J. 2004, 10, 1637.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXjt1Sls74%3D&md5=19d78cfa8a945578be80aec25f077ad7CAS |

[51]  A. Farrokhnia, B. Sakakini, K.C. Waugh, Catal. Lett. 2001, 76, 241.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXptVGgtL4%3D&md5=71198ebe583a499f8d8cdf7af6e218e7CAS |