Abstract
Novel mono-Schiff base MnIII complexes with pendant aza-crown or morpholino groups have been synthesized and studied as catalysts in aerobic oxidation of p-xylene to p-toluic acid. The oxidation of p-xylene to p-toluic acid with air at 120 °C under normal atmospheric pressure occured efficiently in the presence of aza-crown ether substituted mono-Schiff base MnIII complexes. Significant selectivity (up to ~90%) and conversion levels (up to ~38%) were obtained. The effect of the aza-crown ether pendant in MnIII Schiff base complexes on the oxidation of p-xylene was also investigated by comparison with the morpholino pendant analogues. The addition of alkali metal ions accelerated the rate of conversion of p-xylene to p-toluic acid.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
M. Hudlicky, Oxidation in Organic Chemistry, ACS Monograph 186, American Chemical Society, Washington DC
B.M. Trost, Comprehensive Organic Synthesis (Oxidiation), New York, 1991
C.R. Jacob S.P. Varkey P. Ratnasamy (1999) Appl. Catal. A 182 91 Occurrence Handle1:CAS:528:DyaK1MXis1Kjtb8%3D
F. Fang J. Sun R. Zheng W.W. Qiu J. Tang M.Y. He (2004) Tetrahedron 60 1225 Occurrence Handle10.1016/j.tet.2004.04.012
W. Partenheimer (1991) J. Mol. Catal. 67 35 Occurrence Handle1:CAS:528:DyaK3MXlsFyhurY%3D
W. Partenheimer and R.K. Gipe in Catalytic Selective Oxidation, S.T. Oyama and W. Highower (eds), ACS Symp. Ser., 523, 81 (1993)
W. Zeng J.Z. Li S.Y. Qin (2004) Supramol. Chem. 16 569 Occurrence Handle1:CAS:528:DC%2BD2cXhtFWqsL%2FK
S.B. Haliigudi B.M. Devassy M.P. Degaonkar S. Gopinathan (2000) React. Kinet. Catal. Lett. 71 289
H. Hochisako, H. Ihara, J. Kamiya and K. Yamnda, Chem. Commun., 19 (1997)
A. Galon D. Andreu A.M. Echavarren P. Prades (1992) J. Am. Chem. Soc. 114 1511
X.X. Lu S.Y. Qin Z.Z. Zhou V.W.W. Yam (2003) Inorg. Chem. Acta 346 49 Occurrence Handle10.1016/S0020-1693(02)01391-9 Occurrence Handle1:CAS:528:DC%2BD3sXhvFSku78%3D
R.J.M.K. Gebbink, C.F. Martens, M.C. Feiter, K.D. Karlin and R.J.M. Nolte, Chem. Commun., 389 (1997)
X.Y. Wei J.Z. Li B. Zhou S.Y. Qin (2004) Transition. Met. Chem. 29 457 Occurrence Handle10.1023/B:TMCH.0000027463.00158.6b Occurrence Handle1:CAS:528:DC%2BD2cXjvVKns7Y%3D
K. Auwers O. Bürger (1904) Chem. Ber. 37 3929
T.B. Lu C.T. Wu (1985) Chin. J. Org. Chem. 4 312
W. Zeng J.Z. Li Z.H. Mao Z. Hong S.Y Qin (2004) Adv. Synth. Catal. 346 1385 Occurrence Handle10.1002/adsc.200404094 Occurrence Handle1:CAS:528:DC%2BD2cXoslegt7g%3D
W.J. Geary (1971) Coord. Chem. Rev. 7 81 Occurrence Handle10.1016/S0010-8545(00)80009-0 Occurrence Handle1:CAS:528:DyaE3MXlsVCgsrg%3D
W. Zeng Z.H. Mao X.Y. Wei J.Z. Li Z. Hong S.Y. Qin (2002) J. Supramol. Chem. 2 510 Occurrence Handle10.1016/j.jsupra.2004.02.001
F. Vögtle E. Weber U. Elben (1980) Kontakte(Darmstadt) 2 36
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Yan, J., Li, Jz., Li, Kb. et al. Synthesis and Study of Mono-Schiff Base MnIII Complexes with Aza-crown or Morpholino Pendant as Catalyst in Aerobic Oxidation of p-xylene to p-toluic Acid. Transition Met Chem 31, 286–292 (2006). https://doi.org/10.1007/s11243-005-6369-0
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s11243-005-6369-0