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Alkylation of 4-methoxyphenol with MTBE catalyzed by 12-tungstophoric acid supported on neutral alumina

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Abstract

Alkylation of 4-methoxyphenol with MTBE catalyzed by neutral alumina-supported heteropolyphosphotungstic acids and several other kinds of solid acids was investigated. The results indicate that the reaction activity is correlated with the total acidity of catalysts and the distributions of O-alkylated, mono- and di-C-alkylated products correspond to weak, moderate and strong acidity of catalysts, respectively. They are tunable by supporting different amounts of H3PW12O40 on neutral alumina, and the supported catalysts can be reused.

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References

  1. Mahon, J.H., Chapman, R.A.: Estimation of 2- and 3-tert-Butyl-4-hydroxyanisole isomers in commercial butylated hydroxyanisole. Anal. Chem. 24, 534–536 (1952)

    Article  CAS  Google Scholar 

  2. Kraybill, H.R., Dugan, L.R.: ANTIOXIDANTS new developments for food use. J. Agric. Food. Chem. 2, 81–84 (1954)

    Article  CAS  Google Scholar 

  3. Szalkowski, C.R., Garber, J.B.: Determination of 2,6-di-tert-butyl-4- hydroxytoluene (BHT): application to edible fats and oils. J. Agric. Food. Chem. 10, 490–495 (1962)

    Article  CAS  Google Scholar 

  4. Alkylation of phenols. US 2,470,902 (C 07 C 37/11), publ. 24.05.49

  5. Preparation of tertiary butyl hydroquinone. US 2,722,556 (C 07 C 37/16), publ. 01.11.55

  6. Timofeeva, M.N.: Acid catalysis by heteropoly acids. Appl. Catal. A Gen. 256, 19–35 (2003)

    Article  CAS  Google Scholar 

  7. Okuhara, T.: Water-tolerant solid acid catalysts. Chem. Rev. 102, 3641–3666 (2002)

    Article  CAS  Google Scholar 

  8. Kuang, W., Rives, A., Fournier, M.M., Hubaut, R.: Structure and reactivity of silica-supported 12-tungstophosphoric acid. Appl. Catal. A Gen. 250, 221–229 (2003)

    Article  CAS  Google Scholar 

  9. Bhatt, N., Patel, A.: Liquid phase tert-butylation of cresols catalysed by 12-tungstophosphoricacid and 12-tungstosilicicacid supported onto neutral alumina. Catal. Lett. 113, 99–103 (2007)

    Article  CAS  Google Scholar 

  10. Devassy, B.M., Halligudi, S.B.: Zirconia-supported heteropoly acids: Characterization and catalytic behavior in liquid-phase veratrole benzoylation. J. Catal. 236, 313–323 (2005)

    Article  CAS  Google Scholar 

  11. Bachiller-Baeza, B., Anderson, J.A.: FTIR and reaction studies of styrene and toluene over silica–zirconia-supported heteropoly acid catalysts. J. Catal. 228, 225–233 (2004)

    Article  CAS  Google Scholar 

  12. Yadav, G.D., Doshi, N.S.: Alkylation of phenol with methyl-tert-butyl ether and tert-butanol over solid acids: efficacies of clay-based catalysts. Appl. Catal. A Gen. 236, 129–147 (2002)

    Article  CAS  Google Scholar 

  13. Yadav, G.D., Rahuman, M.S.M.: Efficacy of solid acids in the synthesis of butylated hydroxyl anisoles by alkylation of 4-methoxyphenol with MTBE. Appl. Catal. A Gen. 253, 113–123 (2003)

    Article  CAS  Google Scholar 

  14. Li, G., Ren, F.G., Cui, Y.J., Yang, F., Zhang, J.: Alkylation of 2-naphthol with long-chain olefins over zeolites. React. Kinet. Catal. Lett. 93, 109–117 (2008)

    Article  CAS  Google Scholar 

  15. Subramanian, S., Mitra, A., Satyanarayana, C.V.V., Chakrabarty, D.K.: Para-selective butylation of phenol over silicoaluminophosphate molecular sieve SAPO-11 catalyst. Appl. Catal. A Gen 159, 229–240 (1997)

    Article  CAS  Google Scholar 

  16. Sugii, T., Ohnishi, R., Zhang, J., Miyaji, A., Kamiya, Y., Okuhara, T.: Acidity-attenuated heteropolyacid catalysts: acidity measurement using benzonitrile-TPD and catalytic performance in the skeletal isomerization of n-heptane. Catal. Today 116, 179–183 (2006)

    Article  CAS  Google Scholar 

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Acknowledgments

The authors thank Mr. Zhimin Wang from Zhejiang Shuren University for GC–MS measurements. We are grateful to the financial support given by NSFC (20573094).

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Authors and Affiliations

  1. Institute of Catalysis and Key Lab of Applied Chemistry of Zhejiang Province, Zhejiang University, Hangzhou, 310028, People’s Republic of China

    Huangju Cai, Jianxin Mao, Yufei Tao & Xiaoming Zheng

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  1. Huangju Cai
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  2. Jianxin Mao
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Correspondence to Jianxin Mao.

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Cai, H., Mao, J., Tao, Y. et al. Alkylation of 4-methoxyphenol with MTBE catalyzed by 12-tungstophoric acid supported on neutral alumina. React Kinet Catal Lett 97, 43–50 (2009). https://doi.org/10.1007/s11144-009-0021-5

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  • DOI: https://doi.org/10.1007/s11144-009-0021-5

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