An Eco-Friendly Catalytic Route for One-Pot Synthesis of Phenols from Aromatics and Hydroxylamine

Abstract:

A series of ionic liquids were used as a co-solvent in the reaction of one-pot synthesis of phenols from aromatics and hydroxylamine. Then an eco-friendly catalytic system, i.e., [HSO₃-bmi [CF₃SO₃]-H₂O-HAc media with (NH₄)₆Mo₇O₂₄·4H₂O catalyst, was designed for the reaction. The results showed that aromatics were successfully hydroxylated to give the corresponding phenols. Recycling experiments suggested that the catalytic system was stable enough to be recycled.

• Periodical: Advanced Materials Research (Volumes 781-784)
• Pages: 163-168
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.781-784.163
• Online since: September 2013
• Authors: Li Ya Gao, Xue Jun Tan, Wei Xue, Dong Sheng Zhang, Xin Qiang Zhao, Yan Ji Wang*
• Keywords: Aromatics, Hydroxylamine, Hydroxylation, Ionic Liquid (IL), Molybdenum, Phenols

References

[1] M. Weber, M. Weber, Phenols, in: L. Pilato, Phenolic Resins: A Century of Progress, Springer-Verlag, Berlin Heidelberg, 2010, pp.9-23.

[2] M. Bolognini, F. Cavani, D. Scagliarini, C. Flego, C. Perego, M. Saba, Heterogeneous basic catalysts as alternatives to homogeneous catalysts: reactivity of Mg/Al mixed oxides in the alkylation of m-cresol with methanol, Catal. Today. 75 (2002).

DOI: 10.1016/s0920-5861(02)00050-0

[3] A. Bhaumik, P. Mukherjee, R. Kumar, Triphase catalysis over titanium - silicate molecular sieves under solvent - free conditions, J. Catal. 178 (1998) 101-107.

DOI: 10.1006/jcat.1998.2131

[4] B. Vogel, C. Schneider, E. Klemm, The synthesis of cresol from toluene and N2O on H[Al]ZSM-5: minimizing the product diffusion limitation by the use of small crystals, Catal. Lett. 79 (2002) 107-112.

[5] H.A. Burton, I.V. Kozhevnikov, Biphasic oxidation of arenes with oxygen catalysed by Pd(II)-heteropoly acid system: oxidative coupling versus hydroxylation, J. Mol. Catal. A: Chem. 185 (2002) 285-290.

DOI: 10.1016/s1381-1169(02)00127-9

[6] F. Gao, R. Hua, Highly efficient K7NiV13O38-catalyzed hydroxylation of aromatics with aqueous hydrogen peroxide (30%), Appl. Catal. A: Gen. 270 (2004) 223-226.

DOI: 10.1016/j.apcata.2004.05.007

[7] D. Zhang, L. Gao, W. Xue, X. Zhao, S. Wang, Y. Wang, One-pot synthesis of phenols by hydroxylation of aromatics with hydroxylamine, Chem. Lett. 41(2012) 369-371.

DOI: 10.1246/cl.2012.369

[8] C.M. Gordon, New Developments in catalysis using ionic liquids, Appl. Catal. A: Gen. 222 (2001) 101-117.

[9] H. Olivier-Bourbigou, L. Magna, D. Morvan, Ionic liquids and catalysis: Recent progress from knowledge to applications, App Catal A: Gen. 373 (2010) 1-56.

DOI: 10.1016/j.apcata.2009.10.008

[10] Z. Duan, Y. Gu, J. Zhang, L. Zhu, Y. Deng, Protic pyridinium ionic liquids: Synthesis, acidity determination and their performances for acid catalysis, J. Mol. Catal. A: Chem. 250 (2006) 163-168.

DOI: 10.1016/j.molcata.2006.01.035