Ultrasonically Promoted Synthesis of Ethyl 2-(naphthalen-2-yloxy)acetate in Solid-Liquid Heterogeneous Phase Transfer Catalysis Condition

Pachaiyappan Abimannan  -  Pachaiyappa’s College for Men, Kanchipuram, Tamil Nadu,, India
*Venugopal Rajendran  -  Pachaiyappa’s College for Men, Kanchipuram, Tamil Nadu,, India
Received: 28 Jun 2016; Published: 11 Oct 2016.
Open Access Copyright (c) 2016 Bulletin of Chemical Reaction Engineering & Catalysis
Creative Commons License
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.

Citation Format:
Cover Image

In this paper, the synthesis of ethyl 2-(naphthalen-2-yloxy)acetate from β-naphthol and ethyl 2-bromoacetate under ultrasound and catalyzed by quaternary ammonium salt in solid-liquid heterogeneous condition was described. Trace amount of water play a major role in this solid-liquid reaction. The reaction follows pseudo first order rate law. The apparent rate constant of the organic phase reaction was obtained form the experimental data. The combination of small amount of tetrabutylammonium bromide (TBAB) and ultrasound (kapp = 25.22×10-3 min-1) shows several fold enhanced rate of the reaction than the conventional operation (kapp = 6.42×10-3 min-1 for TBAB only).  The rate constant increases (0.05 to 0.3 g) with increase in the concentration of catalyst (from kapp = 10.12×10-3 min-1 to kapp = 34.46×10-3 min-1). The other kinetic effects such as, effect of agitation speed, kind of frequency of ultrasound, kind of various quantity of K2CO3, quantity of water, temperature, different quaternary ammonium salts, solvents and volume of organic solvents on the conversion of ethyl 2-bromoacetate  and apparent rate constant were investigated in detail and rational explanations are provided. Copyright © 2016 BCREC GROUP. All rights reserved

Received: 4th November 2015; Revised: 13rd January 2016; Accepted: 16th January 2016

How to Cite: Abimannan, P., Rajendran, V. (2016). Ultrasonically Promoted Synthesis of Ethyl 2-(naphthalen-2-yloxy)acetate in Solid-Liquid Heterogeneous Phase Transfer Catalysis Condition. Bulletin of Chemical Reaction Engineering & Catalysis, 11 (3): 273-283 (doi:10.9767/bcrec.11.3.567.273-283)

Permalink/DOI: http://doi.org/10.9767/bcrec.11.3.567.273-283

phase-transfer catalyst; solid-liquid mode; ethyl 2-bromoacetate; ethyl 2-(naphthalen-2-yloxy)acetate; ultrasonication

Article Metrics:

  1. Starks, C.M., Liotta, C.L., Halpern, M.E. (1994). Phase-Transfer Catalysis: Fundamentals, Applications, and Industrial Perspectives, Chapman and Hall Publications, New York, U.S.A.
  2. Weber, W.P., Gokel, G.W. (1997). Phase Transfer Catalysis in Organic Syntheses, Springer Verlag, New York, U.S.A.
  3. Dehmlow, E.V., Dehmlow, S.S. (1993). Phase Transfer Catalysis, 3rd ed., VCH, New York, U.S.A.
  4. Menger, F.M. (1972). Reactivity of organic molecules at phase boundaries. Chem. Soc. Rev. 1: 229-240.
  5. Sasson, Y., Neumann, R. (1997). Handbook of Phase Transfer Catalysis, Blackie Academic and Professional (Chapman & Hall), London.
  6. Makosza, M., Wawrzyniewicz, M. (1969). Reaction of organic anions XXIV catalytic method for preparation of dichlorocyclopropane derivatives in aqueous medium. Tetrahedran Lett. 53: 4659-4662.
  7. (a) Bijudas, K., Bashpa, P., Bibin, V.P., Nair, L., Priya, A.P., Aswathy, M., Krishnendu, C., Lisha, P. (2015). Bulletin of Chemical Reaction Engineering & Catalysis, 10 (1): 38-42. (doi:10.9767/bcrec.10.1.7189.38-42)
  8. Bijudas, K., Bashpa, P., Nair, T.D.R. (2014). Bulletin of Chemical Reaction Engineering & Catalysis, 9 (2): 142-147. (doi:10.9767/bcrec.9.2.6476.142-147)
  9. (a) Mason T.J. (1997). Ultrasound in synthetic organic chemistry. Chem. Soc. Rev., 26: 443–451.
  10. (b) Polackova, V., Hutka, M., Toma, S. (2005). ultrasound effect on Suzuki reactions. 1. Synthesis of unsymmetrical biaryls. Ultrason. Sonochem. 12: 99–102.
  11. Wang, M.L., Rajendran, V. (2006). A kinetic study of thioether synthesis under influence of ultrasound assisted phase-transfer catalysis. J. Mol. Catal. A: Chem. 244: 237–243.
  12. Wang, M.L., Rajendran, V. (2007). Ultrasound assisted phase-transfer catalytic epoxidation of 1,7-octadiene – a kinetic study. Ultrason. Sonochem., 14: 46–54.
  13. Li, J.T., Li, X.L. (2007). An efficient and practical synthesis of methylene dioximes by combination of ultrasound and phase transfer catalyst. Ultrason. Sonochem., 14: 677–679.
  14. Nandurkar, N.S., Bhanushali, M.J., Jagtap, S.R., Bhanage, B.M. (2007). Ultrasound promoted regioselective nitration of phenols using dilute nitric acid in the presence of phase transfer catalyst. Ultrason. Sonochem. 14: 41–45.
  15. Yang, H.M., Peng, G.Y. (2010). Ultrasound-assisted third-liquid phase-transfer catalyzed esterification of sodium salicylate in a continuous two-phase flow reactor. Ultrason. Sonochem. 17: 239–245.
  16. Wang, M.L., Chen, C.J. (2010). Kinetic Study of Synthesizing 1-(3-Phenylpropyl)pyrrolidine-2,5-dione under Solid-Liquid Phase-Transfer Catalytic Conditions Assisted by Ultrasonic Irradiation. Org. Process. Res. Dev. 14: 737–745.
  17. Mason, T.J., Lorimer, J.P. (1998). Sonochemistry: Theory, applications and uses of ultrasound in chemistry, Ellis Horwood Limited.
  18. Lan, J.K. (1995). Hydrolysis and substitution reactions of halo-ester, MS Thesis, National Tsing-Hua University, Taiwan.
  19. Rokade, Y., Dongare, N. (2010). Synthesis and antimicrobial activity of some azetidinone derivatives with the β-naphthol. Rasayan J. Chem, 3: 641-645.
  20. Bhaumik, A., Upendhar, M., Soundarya, D., Sravan Kumar, P., Manogna, Ch. (2013). Synthesis, characterization and evaluation for anti-arthritic activity of some novel 4- thiazolidinone derivatives. Int. Res J Pharm. App Sci. 3 (5): 88-93.
  21. Muhammad, S. A., Nadeem, H., Sadiq, A. (2014). Computational drug designing against salmonella typhi: a causative agent of typhoid Int. J. Pharm. 4(1): 252- 255.
  22. Bhaumik, A., Chandra, M. A., Saha, S., Mastanaiah, J., Visalakshi, T. (2014). Synthesis, characterization and evaluation of anticonvulsant activity of some novel 4-thiazolidinone derivatives. Sch. Acad. J. Pharm. 3(2): 128-132.
  23. Naik, S.D., Doraiswamy, L.K. (1997). Mathematical model of solid-liquid phase-transfer Catalysis. Chem. Eng. Sci. 52: 4533-4546.
  24. Yadav, G.D., Sharma, M.M. (1981). Kinetics of benzyl chloride with sodium acetate/benzoate: phase transfer catalysis in solid-liquid system. Ind. Eng. Chem. Proc. Des. Dev. 20: 385-390.
  25. Vander, Z.M.C., Hartner, F.W. (1978). Solid–liquid phase-transfer catalysis by a quaternary ammonium salt. A comparison with crown ethers and polyalkylamines. J. Org. Chem. 43: 2655-2657.
  26. Sasson Y., Zahalka, H.A. (1983). Catalyst poisoning phenomenon in phase transfer catalysis: effect of aqueous phase concentration. J. Chem. Soc., Chem. Commun. 1347-1349.
  27. Torok, B., Balazsik, K., Felfoldi, K., Bartok, M. (2001). Asymmetric reaction in Sonochemistry. Ultrason. Sonochem. 8: 191-200.
  28. Guilet, R., Berlan, J., Louisnared, O., Schwartzentruber, J. (1998). Influence of ultrasound power on the alkylation of phenylacetonitrile under solid-liquid phase transfer catalysis conditions. Ultrason. Sonochem. 5: 21-25.
  29. Vivekanand, P. A., Wang, M. L. (2011). Sonocatalyzed synthesis of 2-phenylvaleronitrile under controlled reaction conditions – A kinetic study. Ultrason. Sonochem. 18: 1241–1248.
  30. Abimannan, P., Selvaraj, V., Rajendran, V. (2015). Sonication effect on the reaction of 4-bromo-1-methylbenzene with sodium sulfide in liquid–liquid multi-site phase-transfer catalysis condition – Kinetic study. Ultrason. Sonochem. 23: 156–164.
  31. Wang, M.L., Rajendran, V. (2007). Ethoxylation of p-chloronitrobenzene using phase-transfer catalysts by ultrasound irradiation – A kinetic study. Ultrason. Sonochem. 14: 368–374.
  32. Wang, M.L., Rajendran, V. (2007). Kinetics for dichlorocyclopropanation of 1,7-octadiene under the influence of ultrasound assisted phase-transfer catalysis condition. J. Mol. Catal. A: Chem. 273: 5–13.
  33. Rajendran, V., Wang, M.L. (2008). Dichlorocarbene addition to allyl phenyl ether under phase-transfer catalysis conditions – a kinetic study. J. Mol. Catal. A: Chem. 288: 23–27.
  34. Selvaraj, V., Rajendran, V. (2014). Propargylation of indene-1,3-dione under a new phase-transfer catalyst combined with ultrasonication – A kinetic study. Ultrason. Sonochem. 21: 612–619.
  35. Zhao, Q., Sun, J., Li, J., He, J. (2013). Kinetics and mechanism of Horner–Wadsworth–Emmons reaction of weakly acidic phosphonate in solid–liquid phase-transfer catalysis system. Catal. Commun. 36: 98–103.
  36. Jeeru, L.R., Pradhan, N.C., Kundu, G. (2015). Reduction of Chloronitrobenzenes by Aqueous Ammonium Sulphide: Triphase Catalysis by Anion Exchange Resin Indian Chemical Engineer, DOI: 10.1080/00194506.2015.1044028, pp 1-18.
  37. Landeros, J.M., Silvestre, H.A., Guadarrama, P. (2013). Synthesis of branched cores by poly-O-alkylation reaction under phase transferconditions. A systematic study. J. Mol. Struct. 1037: 412–419.
  38. Selvaraj, V., Rajendran, V. (2014). Ultrasound assisted the preparation of 1-(4-nitrophenyl)imidazole under a new multi-site phase-transfer catalyst – Kinetic study. Ultrason. Sonochem. 21: 620–627.
  39. Albanese, D., Landini, D., Maia, A., Penso, M. (1999). Phase transfer catalysis: some recent applications in organic Synthesis. J. Mol. Catal. A: Chem. 150: 113–131.
  40. Wang, M.L., Chen, C.J. (2008). Kinetic Study of Synthesizing 1-(3-Phenylpropyl)-pyrrolidine-2,5-dione under Solid−Liquid Phase-Transfer Catalysis. Org. Process Res. Dev. 12: 748.
  41. Kurella, S., Basu, J.K. and Sengupta, S. (2015). Study of Solid–Liquid Phase Transfer Catalysed Reaction to Produce P-Nitroanisole Using 18-Crown-6 as Catalyst. Indian Chemical Engineer, DOI: 10.1080/00194506.2015.1064791.
  42. Zhao, Q., Sun, J., Liu, B., He, J. (2013). Synthesis of stilbene, 1,4-distyrylbenzene and 4,4’-distyrylbiphenyl via Horner-Wadsworth-Emmons reaction in phase-transfer catalysis System. Dyes and Pigments. 99: 339-347.