Synthesis of 1-butoxy-4-tert-butylbenzene under The Effect of Multi-site Phase Transfer Catalysis System – A Kinetic Study

Manickam Sathiyaraj  -  PG & Research, Department of Chemistry, Pachaiyappa’s Col, India
*Perumal Venkatesh  -  PG & Research, Department of Chemistry, Pachaiyappa’s Col, India
Received: 5 Apr 2020; Revised: 25 Apr 2020; Accepted: 26 Apr 2020; Published: 1 Aug 2020; Available online: 30 Jul 2020.
Open Access Copyright (c) 2020 Bulletin of Chemical Reaction Engineering & Catalysis
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Phase transfer catalysis technique proved to be a useful method for synthesizing various organic compounds under heterogeneous reactions and recognized as a viable environmentally friendly. The influence of a new multi site phase transfer catalyst (MPTC) is the synthesis of 1-butoxy-4-tertbutylbenzene from 4-tert-butylphenol with 1-bromobutane (BB) under heterogeneous solid-liquid condition using potassium hydroxide as a base at 60 °C. The higher conversion of 1-bromobutane was achieved by using the synergistic condition of multi-site phase transfer catalyst in better efficacy. The reaction rate enhanced by decreases the volume of water. The apparent the reaction rate was found to be pseudo-first order kinetics. The apparent rate constant was increased linearly with the increase in the concentration of various parameters, such as: MPTC, temperature, potassium hydroxide, and stirring speed. The activation energy (Ea) was also calculated through the Arrhenius plot. Copyright © 2020 BCREC Group. All rights reserved


Keywords: MPTC; phase transfer catalysis; 4-(tert-butyl)phenol; 1-bromobutane; kinetics; 1-butoxy-4-(tert-butyl)benzene

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  1. Rasmussen, J.K., Smith, H.K. (1981). Phase transfer free radical reactions: The Crown ether potassium peroxy disulphate initiator system. Journal of American Chemical Society, 103, 730-736.
  2. Wang, M.L., Hsieh, Y.M. (2004). Kinetic study of dichlorocyclopropanation of 4-Vinyl-1-cyclohexene by a Novel Multisite Phase Transfer Catalyst. Journal of Molecular Catalysis A: Chemistry, 210, 59–68.
  3. Vajjiravel, M., Umapathy, M.J. (2010). Synthesis, characterization and application of a multi-site phase transfer catalyst in radical polymerization of n-butyl methacrylate—a kinetic study. International Journal of Polymeric Materials, 59, 647-662.
  4. Makosza, M., Fedorynski, M. (2012). Phase Transfer Catalysis – Basic Principles, Mechanism and Specific Features. Current Catalysis, 57, 79–87.
  5. Yadav, G. D. (2004). Insight into green phase - transfer catalysis. Topics in Catalysis, 29, 145-161.
  6. Jones, R.A. (2001). Quaternary Ammonium Salts: Their Use in PhaseTransfer Catalysed Reactions. Academic Press: U.K.
  7. Ocic, O. (2005). Oil Refineries in the 21st Century: Energy Efficient, Cost Effective, Environmentally Benign; John Wiley & Sons: New York.
  8. Murugan, E., Tamizharasu, G. (2012). Synthesis and Characterization of New Soluble Multisite Phase Transfer Catalysts and Their Catalysis in Free Radical Polymerization of Methyl Methacrylate Aided by Ultrasound - A Kinetic Study. Journal of Applied Polymer science, 125, 263–273.
  9. Vivekanand, P.A., Balakrishnan, T. (2009). Kinetics of dichlorocyclopropanation of vinylcyclohexane catalysed by a new multi-site phase transfer catalyst. Catalysis Communication, 72, 687-692.
  10. Wang, M. L., Lee, Z.F., (2006). Reaction of 4,4-bis (chloromethyl)-1,10-biphenyl and Phenol in two-phase medium via phase-transfer catalysis. Journal of Molecular Catalysis A: Chemistry, 264, 19- 127.
  11. Loganathan, S., Rajendran, V. (2013). Ultrasound assisted polymerization of N-vinyl imidazole under phase-transfer catalysis condition – A kinetic study. Ultrasonics Sonochemistry, 20, 308-313.
  12. Mason, D., Magdassi, S., Sasson, Y. (1991). Role of a third liquid phase in phase-transfer Catalysis. Journal of Organic Chemistry, 56, 7229- 7232.
  13. Abimannan, P., Rajendran, V. (2016). Kinetic Study for the Synthesis of 1-nitro-4-(prop-2- yn yloxy) benzene in Solid-Liquid PTC Condition. Current Catalysis, 5, 44-50.
  14. Selvaraj, V., Rajendran, V. (2013). Preparation of 1,3-bis(allyloxy)benzene under a New multi- site phase-transfer catalyst combined with ultrasonication – A kinetic study. Ultrasonics Sonochemistry, 20, 1236–1244.
  15. Idoux, J.P., Wysocki, R., Young, S., Turcot, J., Ohlman, C., Leonard, R. (1983). polymer-supported "multi-site" phase transfer catalysts. Synthetic Communication, 13, 39-144.
  16. Vivekanand, P.A., Balakrishnan, T. (2009). Superior catalytic efficiency of a new multisite Phase transfer catalyst in the C-alkylation of dimedone – a kinetic study. Catalysis Communication, 10, 1371- 1375.
  17. Balakrishnan, T., Jeyachandran, J.P. (1995). New multi-site phase transfer catalyst for the addition of dichlorocarbene to styrene. Journal of Chemical Society: Perkin Trans, 2, 2081- 2085.
  18. Balakrishnan, T., Shanmugan, K. (2007). New multi-site phase transfer catalyst for the addition of dichlorocarbene to olefins. Indian Journal of Chemistry A, 46, 1069-1074.
  19. Murugan, E., Tamizharasu, G. (2012). New soluble multi-site phase transfer catalysts and their catalysis for dichlorocarbene addition to citronellal assisted by ultrasound—A kinetic study. Journal of Molecular Catalysis A: Chemistry, 364, 81–89.
  20. Wang, M.L., Lee, Z.F. (2006). Synthesis of Novel Multisite Phase-Transfer Catalysts and Their Applications to the Catalyzed Reaction of Bisphenol A and Allyl Bromide. Industrial Engineering Chemistry Research, 45, 4918-4926.
  21. Balakrishnan, T., Murugan, E., Siva, A. (2004). Synthesis and characterization of novel soluble multi-site phase transfer catalyst; its efficiency compared with single-site phase transfer catalyst in the alkylation of phenylacetonitrile as a model reaction. Applied Catalysis A: General, 273, 89-97.
  22. Harikumar, K., Rajendran, V. (2014). Ultrasound assisted the preparation of 1-butoxy-4-nitrobenzene under a new multi-site phase-transfer catalyst – Kinetic study. Ultrasonics Sonochemistry, 21, 208 – 215.
  23. Brahmayya, M., Wang, M.L. (2016). Kinetic study for benzyloxylation of p-bromotoluene using phase transfer catalyst assisted by microwave irradiation. Journal of Taiwan Institute of Chemical Engineering, 000, 1–7.
  24. Vajjiravel, M., Marimuthu, E., Yoganand, K.S., Umapathy, M.J. (2017). Multi-site phase transfer catalyzed radical polymerization of methyl methacrylate in mixed aqueous–organic medium: a kinetic study. International Journal of Industrial Chemistry, 8, 241–251.
  25. Vajjiravel, M., Umapathy, M.J. (2016). Phase transfer catalyst aided radical polymerization of n-butyl acrylate in two-phase system: a kinetic study. International Journal of Industrial Chemistry, 7, 441–448.
  26. Wang, M.L., Rajendran, V. (2007). Ultrasound assisted phase-transfer catalytic epoxidation of 1,7-octadiene – A kinetic study. Ultrasonics Sonochemistry, 14, 46–54.
  27. Murugan, E., Siva, A. (2006). New trimeric Cinchona alkaloid-based quaternary Ammonium salts as efficient chiral phase transfer catalysts for enantioselective synthesis of α-amino acids. Journal of Molecular Catalysis A: Chemistry, 248, 1-9.
  28. Kirsten, T.A., Olov, S., Christer, H. (2000). Tyrosinase-Mediated Formation of a Reactive Quinone from the Depigmenting Agents, 4-tert-Butylphenol and 4-tert-Butylcatechol. Pigment Cell Research, 13, 33-38.
  29. Starks, M., Liotta, C.L., Halpern, M. (1994). Phase Transfer Catalysis, Fundamentals, Applications, and Industrial Perspectives, Chapman & Hall, New York.
  30. Makosza, M., Fedorynski, M. (2003). Phase Transfer Catalysis. Catalysis Reviews, 45, 321-367
  31. Wang, M.L., Hsieh, Y.M., Chang, R.Y. (2003). Kinetics study of dichlorocyclopropanation of 1,7-octadiene under phase transfer catalysis conditions at high alkaline concentration. Industrial Engineering Chemistry Research, 42, 4702-4707.

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