Abstract
The solvent-free catalytic oxidation of toluene using molecular oxygen over metalloporphyrin/N-hydroxyphthalimide (NHPI)/cetyl trimethyl ammonium bromide (CTAB) has been developed. The results showed that the type of metalloporphyrin used, catalyst loading, reaction temperature, and the flow rate of oxygen all influenced the conversion of toluene and the selectivities of the products. Furthermore, a co-catalysis was observed between metalloporphyrin, NHPI, and CTAB. The toluene conversion was significantly improved from 10.74 to 40.95 mol% after adding CTAB to the reaction mixture. Based upon experimental observations, a possible mechanism was also proposed for the present oxidation.
Graphical Abstract
Similar content being viewed by others
References
Sheldon RA, Kochi JK (1981) Metal catalyzed oxidation organic compounds. Academic Press, New York
Borgaonkar HV, Raverkar SR, Chandalia SB (1984) Ind Eng Chem Prod Res Dev 359:455
Partenheimer W (1995) Catal Today 23:69
Kantam ML, Sreekanth P, Rao KK, Kumar TP, Rao BP et al (2002) Catal Lett 81:223
Guo CC, Liu Q, Wang XT, Hu HY (2005) Appl Catal A 282:55
Huang G, Wang AP, Liu SY, Guo YA et al (2007) Catal Lett 114:174
Kesavan L, Tiruvalam R, Rahim MH et al (2011) Science 331:195
Wang F, Xu J, Li XQ, Gao J et al (2005) Adv Synth Catal 347:1987
Li XH, Chen JS, Wang XC, Sun JH, Antonietti M (2011) J Am Chem Soc 133:8074
Ishii Y, Sakaguchi S, Iwahama T (2001) Adv Synth Catal 343:393
Yang GY, Zheng LW, Wu GH, Lin XS et al (2007) Adv Synth Catal 349:2445
Ellis PE, Lyons JE (1990) Coord Chem Rev 105:181
Guo CC, Liu XQ, Liu Q, Liu Y et al (2009) J Porphyr Phthalocyanines 13:1250
Jiang Q, Sheng WB, Guo XD, Tang J, Guo CC (2013) J Mol Catal A 373:121
Liu Q, Guo CC (2012) Sci China Chem 55:2036
Deng W, Luo WP, Tan Z, Liu Q et al (2013) J Mol Catal A 372:84
Guo CC, Gui MD, Zhu SJ (1994) Chin J Org Chem 14:163
Steven E, John R, Lindsay S (2000) J Chem Soc Perkin Trans 2:1541
Jiang Q, Xiao Y, Tan Z, Li QH, Guo CC (2008) J Mol Catal A 285:162
Guo CC, Chu MF, Liu Q et al (2003) Appl Catal A 246:303
Black JF (1978) J Am Chem Soc 100:527
Kantam ML, Sreekanth P (2002) Catal Lett 81:223
Meunier B, Visser S, Shaik S (2004) Chem Rev 104:3947
Meunier B (1992) Chem Rev 92:1411
Mansuy D (1993) Coord Chem Rev 125:129
Ma H, Xu J, Zhang QH (2007) Catal Commun 8:27
Stephenson NA, Bell AT (2007) J Mol Catal A 275:54
Traylor TG, Xu F (1987) J Am Chem Soc 109:6201
László J, Csányi, Károly J (1997) J Mol Catal A 120:125
Toribio PP, Campos MJ, Fierro JL (2005) Appl Catal A 294:290
Acknowledgments
We thank the financial supports of National Natural Science Foundation of China (Grants CN21372068).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Deng, W., Wan, Yp., Jiang, H. et al. Solvent-Free Aerobic Oxidation of Toluene over Metalloporphyrin/NHPI/CTAB: Synergy and Mechanism. Catal Lett 144, 333–339 (2014). https://doi.org/10.1007/s10562-013-1104-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-013-1104-5