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An Alternate Green Route to Synthesis of Mono and Diesters using Solid Acid Catalysts

Author Affiliations

  • 1Applied Chemistry Department, Faculty of Technology and Engineering, The M. S. University of Baroda, Vadodara, 390 001, Gujarat, INDIA

Res.J.chem.sci., Volume 5, Issue (2), Pages 48-58, February,18 (2015)

Abstract

The conventional catalysts used in esterification reactions are liquid acids that are not environment friendly. Keeping with global trends, in the present endeavour, an effort has been made to replace the conventional homogeneous liquid acid catalysts by heterogeneous solid acid catalysts. M(IV) Phosphotungstates [M(IV)= Zr, Ti and Sn] which possess inherent acidity have been synthesized by sol-gel route whereas, 12-Tungstophosphoric acid (12-TPA) has been supported onto ZrO2, TiO2 and SnO2 resulting in 12-TPA/ZrO2, 12-TPA/TiO2 and 12-TPA/SnO2 which possesses induced acidity have been synthesized by process of anchoring and calcination. All the catalysts have been characterized for elemental analysis by ICP-AES, TGA, FTIR, SEM, EDX, XRD, surface area (by BET method) and surface acidity (by NH3-TPD method). The potential utility of these materials as solid acid catalysts have been explored by studying esterification as a model reaction wherein mono and diesters have been synthesized. The catalytic activity of synthesized materials has been compared and correlated with acid properties of the materials.

References

  1. Otera J., Esterification, Wiley-VCH: Weinheim, Germany, (2003)
  2. Yadav G.D. and Murkute A.D., Kinetics of synthesis of perfumery grade p-tert-butylcyclohexyl acetate over ion exchange resin catalyst, Int. J. Chem. Reactor Eng., 1, 1-11 (2003)
  3. Ma Y., Jin T., Wang Z. and Li T., A rapid and efficient method for acetylation of phenols with acetic anhydried catalyzed by TiO/SO2- solid super acids, Indian J. Chem., 42B, 1777-1778 (2003)
  4. Ma Y., Wang Q. L., Yan H., Ji X. and Qiu Q., Synthesis of nano-sized Ce0.850.1Ru0.052 (M = Si, Fe) solid solution exhibiting high CO oxidation and water gas shift activity, Appl. Catal. A: Gen., 139, 51-57 (1996)
  5. Okudan S. and Baktir A., Esterification Reaction of polystyrene modified with maleic anhydride in the presence of resin catalyst, Adv. Poly. Technol., 1-11 (2012)
  6. Cheng Y., Feng Y., Ren Y., Liu X., Gao A., Benqiao H., Yan F. and Jianxin L., Comprehensive kinetic studies of acidic oil continuous esterification by cation-exchange resin in fixed bed reactors, Bioresource Technol., 113,65-72 (2012)
  7. Zhang B., Ren J., Liu X., Guo Y., Lu G. and Wang Y., Novel sulfonated carbonaceous materials from p-toluenesulfonic acid/glucose as a high-performance solid-acid catalyst, Catal. Commu., 11, 629-632 (2010)
  8. Toor A. P., Sharma M. and Kumar G., Wanchoo R. K., Ion exchange resin catalyzed esterification of lactic acid with isopropanol : A kinetic study, Bull. Chem. React. Engg. Catal., 6(1), 24-31 (2011)
  9. Brahamkhatri V. and Patel A., Biodiesel Production by Esterification of Free Fatty Acids over 12-Tungstophosphoric Acid Anchored to MCM-41, Ind. Eng. Chem. Res., 50(24), 13693-13702 (2011)
  10. Nascimento L.A.S., Tito L.M.Z., Angelica A.S., Costa C.F.F., Zamian J.M. and Rocha Filho G.N., Esterification of oleic acid over solid acid catalysts prepared from Amazon flint kaolin, Appl. Catal. B: Environ., 101, 495-503 (2011)
  11. Helen L.N., Nicholas A., Zafiropoulos A., Thomas Foglia T., Edward D., Samulski L. and Wenbin L., Mesoporous silica-supported diarylammonium catalysts for esterification of free fatty acids ingreases, J. Am. Oil Chem. Soc., 87, 445-449 (2010)
  12. Bhaumik A. and Inagaki S., Mesoporous Titanium Phosphate Molecular Sieves with Ion-Exchange Capacity, J. Am. Chem. Soc., 123, 691-696 (2001)
  13. Slade R.C.T., Knowels J.A., Jones D.J. and Roziere J., The isomorphous acid salts -Zr(HPO·HO, Ti(HPO·HO and -Zr(HAsO·HO: Comparative thermochemistry and vibrational spectroscopy, Solid State Ionics, 96, 9-19 (1997)
  14. Joshi R., Patel H. and Chudasama U., Synthesis of monoester and diesters using eco-friendly solid acid catalysts M(IV) tungstates and phosphates, Ind. J. Chem.Technol., 15, 238-243 (2008)
  15. Patel H., Joshi R. and Chudasama U., Use of zirconium(IV) phosphate as a solid acid catalyst in some esterification reactions, Ind. J. Chem., 47(A), 348-352 (2008)
  16. Thakkar R. and Chudasama U., Synthesis of mono and diesters using eco-friendly solid acid catalyst - zirconium titanium phosphate, Green Chemistry Letters and Reviews 2, 61-69 (2009)
  17. Patel S., Chudasama U. and Ganeshpure P., Cyclodehydration of 1,4-butanediol catalyzed by metal (IV) phosphates, React. Kinet. Catal. Lett., 76, 317-325 (2002)
  18. Patel S., Chudasama U. and Ganeshpure P., Ketalization of Ketones with diols catalyzed by Metal (IV) phosphates as solid acid catalysts, J. Mol. Cat. A: Chem., 194, 267-271 (2003)
  19. Patel S., Chudasama U. and Ganeshpure P., Tetravalent metal acid salts: Solid acid catalysts for hydration of nitriles to amindes, Indian J. Chem., 42B, 1168-1169 (2003)
  20. Patel S., Chudasama U. and Ganeshpure P., Metal (IV) Phosphates as solid acid catalysts for selective cyclodehydration of 1,N – diols, Green Chem., 3, 143-145 (2001)
  21. Joshi R. and Chudasama U., Synthesis of coumarins via the pechmann condensation using inorganic ion exchangers as solid acid catalysts, J. Sci. Ind. Res., 67,1092-1097 (2008)
  22. Ghodke S. and Chudasama U., Solvent free synthesis of coumarins using environment friendly solid acid catalysts, Appl. Catal. A: Gen., 453, 219-226 (2013)
  23. Khder A.E.R.S., Preparation, characterization and catalytic activity of tin oxide-supported 12-tungstophosphoric acid as a solid catalyst, Appl. Catal. A: Gen., 343(1-2), 109-116 (2008)
  24. Waghmare N.G., Kasinathan P., Amrute A., Lucas N. and Halligudi S.B., Titania supported silicotungstic acid: An efficient solid acid catalyst for veratrole acylation, Cata. Comm., 9, 2026-2029 (2008)
  25. Reddy C., Iyengar P., Nagendrappa G. and Prakash B.J., Esterification of dicarboxylic acids to diesters over n+-montmorillonite clay catalysts, Catal. Lett., 101,87-91 (2005)
  26. Shanmugam S., Viswanathan B. and Varadarajan B.K., Esterification by solid acid catalysts : A comparison, J. Mol. Catal. A: Chem., 223, 143-147 (2004)
  27. Manohar B., Reddy V.R. and Reddy B.M., Esterification by ZrO and Mo-ZrO eco-friendly solid acid catalysts, Synth. Comm., 28, 3183-3187 (1998)
  28. Arabi M., Amini M.M., Abedini M., Nemati A. and Alizadeh M., Esterification of phthalic anhydride with 1-butanol and 2-ethylhexanol catalyzed by heteropolyacidsJ. Mol. Catal. A: Chem., 200, 105-110 (2003)
  29. Kolah A., Ashtana N.S., Vu D.T., Lira C.T. and Miller D.J., Reaction kinetics for the heterogeneously catalyzed esterification of succinic acid with ethanol, Ind. Eng. Chem. Res., 47, 5313-5317 (2008)
  30. Thorat T.S., Yadav V.M. and Yadav G.D., Esterification of phthalic anhydride with 2-ethylhexanol by solid superacidic catalysts, Appl. Catal. 90, 73-96 (1992)