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Selective oxidation of o -nitrotoluene to o -nitrobenzaldehyde with metalloporphyrins as biomimetic catalysts |
| Xinling WANG,Yuanbin SHE, |
| Institute of Green Chemistry
and Fine Chemicals, Beijing University of Technology, Beijing 100124,
China; |
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Abstract Selective oxidation of o-nitrotoluene to o-nitrobenzaldehyde with metalloporphyrins as biomimetic catalysts was studied. The peripheral substituent around porphyrin rings and various process parameters of NaOH concentration, reaction temperature, reaction time and oxygen pressure all affect the selectivity of o-nitrobenzaldehyde. Further, 82.0% selectivity of o-nitrobenzaldehyde was achieved under the optimum conditions: 1.0×10−5mol•L−1 of T(p-NO2)PPFeCl catalyst, 2.5mol•L−1 of NaOH, 0.2mol•L−1 of o-nitrotoluene, 45°C and 2.0MPa for 6h.
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Issue Date: 05 December 2009
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Wei Y Y, Cai M M, Lu C X. Studies on catalytic side-chain oxidation of nitroaromaticsto aldehydes with oxygen. Catal Lett, 2003, 90(1―2): 81―84
doi: 10.1023/A:1025824528577
|
|
Lozar J J, Savall A J. Oxidation of o-nitrotoluene by cerium(IV) methanesulfonate. Ind Eng Chem Res, 1995, 34: 3149―3153
doi: 10.1021/ie00048a028
|
|
Marti H R, Gnehm R. Process for producing o-nitrobenzaldehyde. US Patent, 4463195, 1984
|
|
Holm B. Methodof manufacturing o- and p-nitrobenzaldehyde. US Patent, 4605777, 1986
|
|
Popkov A. Synthesisof 2-nitrobenzaldehyde from 2-nitrotoluene. Acta Chim Slov, 2005, 52: 460―462
|
|
Meunier B. Metalloporphyrinsas versatile catalysts for oxidation reactions and oxidative DNA cleavage. Chem Rev, 1992, 92(6): 1411―1456
doi: 10.1021/cr00014a008
|
|
Groves J T, Bonchio M, Carofiglio T, Shalyaev K. Rapidcatalytic oxygenation of hydrocarbons by ruthenium pentafluorophenylporphyrincomplexes: evidence for the involvement of a Ru(III) intermediate. J Am Chem Soc, 1996, 118: 8961―8963
doi: 10.1021/ja9542092
|
|
She Y B, Fan L L, Zhang Y H, Song X F. Novel technologyfor green synthesis of p-nitrobenzaldehydewith metalloporphyrins as biomimetic catalysts. Journal of Chemical Industry and Engineering, 2004, 12: 2032―2037 (in Chinese)
|
|
Yuan Y, Ji H B, Chen Y X, Han Y, Song X F, She Y B, Zhong R G. Oxidation of cyclohexaneto adipic acid using Fe-porphyrin as a biomimetic catalyst. Org Process Res Dev, 2004, 8: 418―420
doi: 10.1021/op049974s
|
|
Zhang Y H, She Y B, Zhong R G,et al. Study on the correlation between molecular frontierorbital energy and catalytic activity of cobalt porphyrins. Acta Chim Sin, 2004, 62: 2228―2232 (in Chinese)
|
|
Song X F, She Y B, Ji H B, Zhang Y H. Highly efficient,mild, bromide-free and acetic acid-free oxygen oxidation of p-nitrotoluene to p-nitrobenzoic acid with metal pathalocyanine catalysts. Org Process Res Dev, 2005, 9: 297―301
doi: 10.1021/op049810b
|
|
Chen Y X, She Y B, Xu J, Li Y. Studies onQSAR of metalloporphyrin catalysts in the oxidation of cyclohexaneto adipic acid. Front Chem Eng China, 2007, 1(2): 155―161
doi: 10.1007/s11705-007-0029-1
|
|
She Y B, Luo Z H, Song, X F, Duan L L, Yun Y, Zhang T H. Novel green synthesis of o-nitrobenzaldehydeby oxidation of o-nitrotoluenewith metal porphyrins as biomimetic catalysts. Journal of Chemical Industry and Engineering, 2007, 58(11): 2782―2786 (in Chinese)
|
|
Wang L Z, She Y B, Zhong R G, Ji H B, Zhang Y H, Song X F. A green process for oxidation of p-nitrotoluene catalyzed by metalloporphyrins under mild conditions. Org Process Res Dev, 2006,10: 757―761
doi: 10.1021/op060056z
|
|
Chandalia S B, Mukhopadhyay S. Kinetics of catalyzed liquid-phaseoxidation of p-nitrotoluene byair in basic medium. Org Process Res Dev, 1999, 3: 109―113
doi: 10.1021/op980053p
|
|
She Y B, Zhang S F, Yang J Z, Study of cocatalyticaction of NaOH for oxidation of nitrotoluenein liquid-phase. J Dalian Univ Technol, 1999, 39: 56―59 (in Chinese)
|
|
Lyons J E, Ellis P E, Myers H K. Halogenated metalloporphyrin complexes as catalysts forselective reactions of acyclic alkanes with molecular oxygen. J Catal, 1995, 155: 59―73
doi: 10.1006/jcat.1995.1188
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