Reaction Mechanism for Selective Oxidation of Anethole to Anisaldehyde by Hydrogen Peroxide in Presence of Ferric Vanadate

Xingdong Yao; Caihua Peng; Zhanwang Shi

doi:10.14233/ajchem.2014.18171

Issue

Vol. 26 No. 17 (2014): Vol 26 Issue 17

Issue Published : August 27, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Reaction Mechanism for Selective Oxidation of Anethole to Anisaldehyde by Hydrogen Peroxide in Presence of Ferric Vanadate

https://doi.org/10.14233/ajchem.2014.18171

Xingdong Yao

Key Laboratory of Forest Chemistry & Engineering of Guangxi, School of Chemistry & Chemical Engineering, Guangxi University for Nationalities, Nanning 530006, P.R. China

Caihua Peng

Key Laboratory of Forest Chemistry & Engineering of Guangxi, School of Chemistry & Chemical Engineering, Guangxi University for Nationalities, Nanning 530006, P.R. China

Zhanwang Shi

Key Laboratory of Forest Chemistry & Engineering of Guangxi, School of Chemistry & Chemical Engineering, Guangxi University for Nationalities, Nanning 530006, P.R. China

Corresponding Author(s) : Xingdong Yao

13321716154@163.com

Asian Journal of Chemistry, Vol. 26 No. 17 (2014): Vol 26 Issue 17
Article Published : August 12, 2014

Abstract

The reaction mechanism and kinetics for the oxidation of anethole to anisaldehyde by H₂O₂ in the presence of ferric vanadate have been investigated. The results show it is a homogeneous system with vanadium oxodiperoxo ion as the actual oxidant. The reaction follows the pseudo-first order rate equation. Free radical reaction mechanism has been verified by DPPH. A plausible reaction mechanism has been proposed based on the experimental results.

Keywords

Anethole Anisaldehyde Ferric vanadate Hydrogen peroxide Reaction mechanism

Yao, X., Peng, C., & Shi, Z. (2014). Reaction Mechanism for Selective Oxidation of Anethole to Anisaldehyde by Hydrogen Peroxide in Presence of Ferric Vanadate. Asian Journal of Chemistry, 26(17), 5623–5626. https://doi.org/10.14233/ajchem.2014.18171

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References

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References

Q. Wang, F. Liu and S. Yu, Adv. Fine Petrochem., 7, 34 (2006).

I. Kubo and I. Kinst-Hori, J. Agric. Food Chem., 46, 1268 (1998); doi:10.1021/jf9708958.

J. Grimshaw and C. Hua, Electrochim. Acta, 39, 497 (1994); doi:10.1016/0013-4686(94)80092-8.

S. Fliszar and M. Granger, J. Am. Chem. Soc., 91, 3330 (1969); doi:10.1021/ja01040a039.

Y. Xiao, H. Huang, D. Yin, D. Guo, L. Mao and Z. Fu, Catal. Commun., 10, 29 (2008); doi:10.1016/j.catcom.2008.07.035.

H.M. Alvarez, D.P. Barbosa, A.T. Fricks, D.A.G. Aranda, R.H. Valdés and O.A.C. Antunes, Org. Process Res. Dev., 10, 941 (2006); doi:10.1021/op060117t.

A.Y. Yang, S.R. Liu and G.M. Cao, Syn. Chem., 3, 147 (1995).

K. Okamoto, S. Narayama, A. Katsuo, I. Shigematsu and H. Yanase, J. Biosci. Bioeng., 93, 207 (2002); doi:10.1016/S1389-1723(02)80015-9.

H. Mang, J. Gross, M. Lara, C. Goessler, H. Schoemaker, G.M. Guebitz and W. Kroutil, Tetrahedron, 63, 3350 (2007); doi:10.1016/j.tet.2007.02.034.

R. Noyori, M. Aoki and K. Sato, Chem. Commun., 16, 1977 (2003); doi:10.1039/b303160h.

N. Mizuno, K. Yamaguchi and K. Kamata, Coord. Chem. Rev., 249, 1944 (2005); doi:10.1016/j.ccr.2004.11.019.

K. Kamata, K. Yonehara and Y. Sumida, Science, 300, 964 (2003); doi:10.1126/science.1083176.

P. Wright and J. Abbot, Int. J. Chem. Kinet., 25, 901 (1993); doi:10.1002/kin.550251104.

G.B. Shul'pin, Y. Ishii, S. Sakaguchi and T. Iwahama, Russ. Chem. Bull., 48, 887 (1999); doi:10.1007/BF02494631.

V. Conte, F. Di Furia and G. Licini, Appl. Catal. A, 157, 335 (1997); doi:10.1016/S0926-860X(97)00023-9.

X. Yao, C. Peng, Y. Nie, Z. Shi and F. Lei, Chinese Patent 201310180914.6 (2013).

G. Kakabadse and H.J. Wilson, Nature, 180, 861 (1957); doi:10.1038/180861a0.

O.W. Howarth and J.R. Hunt, J. Chem. Soc., Dalton Trans., 1388 (1979); doi:10.1039/dt9790001388.

A.T. Harrison and O.W. Howarth, J. Chem. Soc., Dalton Trans., 1173 (1985); doi:10.1039/dt9850001173.

N.J. Campbell, A.C. Dengel and W.P. Griffith, Polyhedron, 8, 1379 (1989); doi:10.1016/S0277-5387(00)86249-X.

F. Secco, Inorg. Chem., 19, 2722 (1980); doi:10.1021/ic50211a047.

M.J. Clague and A. Butler, J. Am. Chem. Soc., 117, 3475 (1995); doi:10.1021/ja00117a016.

Y. Ishii, K. Yamawaki, T. Ura, H. Yamada, T. Yoshida and M. Ogawa, J. Org. Chem., 53, 3587 (1988); doi:10.1021/jo00250a032.

G. Strukul, Catalytic Oxidations with Hydrogen Peroxide as Oxidant Kluwer Academic, Dordrecht, p. 177 (1992).

A.G.J. Ligtenbarg, R. Hage and B.L. Feringa, Coord. Chem. Rev., 237, 89 (2003); doi:10.1016/S0010-8545(02)00308-9.

C. Bolm, Coord. Chem. Rev., 237, 245 (2003); doi:10.1016/S0010-8545(02)00249-7.

J. Hartung and M. Greb, J. Organomet. Chem., 661, 67 (2002); doi:10.1016/S0022-328X(02)01807-7.

A. Butler, M.J. Clague and G.E. Meister, Chem. Rev., 94, 625 (1994); doi:10.1021/cr00027a004.

Issue

Vol. 26 No. 17 (2014): Vol 26 Issue 17

Reaction Mechanism for Selective Oxidation of Anethole to Anisaldehyde by Hydrogen Peroxide in Presence of Ferric Vanadate

Corresponding Author(s) : Xingdong Yao

Abstract

Keywords

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