Abstract
Diphenyl carbonate (DPC) was synthesized from phenol and dense phase CO2 in the presence of CCl4 and K2CO3 using different catalysts of ZnCl2, ZnBr2, Lewis acid ionic liquids including 1-butyl-3-methylimidazolium chloride (BMIMCl) and bromide (BMIMBr). It was found that K2CO3 was not required, ZnCl2 and ZnBr2 were similar in the catalytic performance, and the use of BMIMCl and BMIMBr was not effective for the production of DPC. For the reactions with ZnCl2 in CCl4, the effects of such reaction variables as temperature, CO2 pressure, the amount of ZnCl2, and the volume of CCl4 were studied in detail. It was shown that the pressure was less influential while a larger amount of ZnCl2, a smaller volume of CCl4, and a low temperature of around 100°C were beneficial for the synthesis of DPC. On the basis of the results obtained, possible reaction mechanisms were discussed.
Similar content being viewed by others
References
Gong J, Ma X, Wang S (2007) Appl Catal A Gen 316:1
Hatanaka I, Mitsuyasu N, Yin G, Fujiwara Y, Kitamura T, Kusakabe K, Yamaji T (2003) J Organomet Chem 674:96
Zhao X, Sun N, Wang S, Li F, Wang Y (2008) Ind Eng Chem Res 47:5298
Rivetti F, Paludetto R, Romano U (1997) EP Patent 785:184
Inaba M, Sawa K, Tanaka T (1997) JP Patent 09(110):805
Yasuda H, Maki N, Choi JC, Sakakura T (2003) J Organomet Chem 682:66
Yasuda H, Watarai K, Choi JC, Sakakura T (2005) J Mol Catal A Chem 236:149
Tundo P, Trotta F, Molaglio G, Ligorati F (1988) Ind Eng Chem Res 27:1565
Fan GZ, Li T, Li GX (2006) Appl Organomet Chem 20:656
Fan GZ, Huang J, Li ZQ, Li T, Li GX (2007) J Mol Catal A Chem 267:34
Omae I (2006) Catal Today 115:33
Schilt MV, Kemmere M, Keurentjes A (2006) Catal Today 115:162
Dinda S, Patwardhan AV, Panda SR, Pradhan NC (2008) Chem Eng J 136:349
Kawanami H, Sasaki A, Matsui K, Ikushima Y (2003) Chem Commun 896
Sun J, Fujita S, Zhao F, Hasegawa M, Arai M (2005) J Catal 230:398
Sun J, Fujita S, Zhao F, Arai M (2005) Appl Catal A Gen 287:221
Bhanage BM, Fujita S, Ikushima Y, Arai M (2003) Green Chem 5:340
Yasuda H, He LN, Sakakura T, Hu CW (2005) J Catal 233:119
Ulusoy M, Cetinkaya E, Cetinkaya B (2009) Appl Organomet Chem 23:68
Tian JS, Miao CX, Wang JQ, Cai F, Du Y, Zhao Y, He LN (2007) Green Chem 9:566
Bhanage BM, Fujita S, He Y, Ikushima Y, Shirai M, Torii K, Arai M (2002) Catal Lett 83:137
Du ZP, Wang Y, Wang GY (2005) Nat Gas Chem Ind 30:21
Naeimi H, Moradi L (2006) J Mol Catal A Chem 256:242
Olah GA, Török B, Joschek JP, Bucsi I, Esteves PM, Rasul G, Prakash GKS (2002) J Am Chem Soc 124:11379
Iijim T, Yamaguchi T (2008) Appl Catal A Gen 345:12
Iijima T, Yamaguchi T (2008) J Mol Catal A Chem 295:52
Shi F, Deng Y, Sima T, Peng J, Gu Y, Qiao B (2003) Angew Chem Int Ed 42:3257
Li Z, Qin Z (2007) J Mol Catal A Chem 264:255
Su K, Li Z, Cheng B, Ren Y (2008) Catal Commun 9:1666
Li Z, Qin Z, Zhu H, Wang J (2006) Chem Lett 35:784
Schmittinger P (2000) Chlorine, principles and industrial practice. Wiley VCH, Weinheim
Jessop PJ, Ikariya T, Noyori R (1999) Chem Rev 99:475
Hobbs HR, Thomas NR (2007) Chem Rev 107:2786
Arai M, Fujita S, Shirai M (2009) J Supercrit Fluid 47:351
Zhao F, Fujita S, Akihara S, Arai M (2005) J Phys Chem A 109:4419
Lindsey S, Jeskey H (1957) Chem Rev 57:583
Li C, Liu W, Zhao Z (2007) Catal Commun 81:834
Alexander MV, Khandekar AC, Samant AD (2004) J Mol Catal A Chem 223:75
Abbott AP, Capper G, Davies DL, Munro HL, Rasheed RK, Tambyrajah V (2001) Chem Commun 2010
Wessely F, Benedict K, Benger H, Friedrich G, Prilinger F (1950) Monatsh 81:1071
Kosugi Y, Takahashi K, Imaoka Y (1999) J Chem Res 114
Kosugi Y, Imaoka Y, Gotoh F, Rahim MA, Matsui Y, Sakanishi K (2003) Org Biomol Chem 1:817
Clifford AA, Pople K, Gaskill WJ, Bartle KD, Rayner CM (1998) J Chem Soc Faraday Trans 94:1451
Song J, Zhang Z, Hu S, Wu T, Jiang T, Han B (2009) Green Chem 11:1031
Zhao F, Zhang R, Chatterjee M, Ikushima M, Arai M (2004) Adv Synth Catal 346:661
Chatterjee M, Ikushima Y, Zhao F (2002) New J Chem 27:27
Meng X, Cheng H, Akiyama Y, Hao Y, Qiao W, Yu Y, Zhao F, Fujita S, Arai M (2009) J Catal 264:1
Tang QL, Hong QJ, Liu ZP (2009) J Catal 263:114
Acknowledgments
This work was supported by the Research Project of Hubei Provincial Department of Education of China (Q20091810).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Fan, G., Fujita, Si., Zou, B. et al. Synthesis of Diphenyl Carbonate from Phenol and Carbon Dioxide in the Presence of Carbon Tetrachloride and Zinc Chloride. Catal Lett 133, 280–287 (2009). https://doi.org/10.1007/s10562-009-0189-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-009-0189-3