Synthesis of ethyl levulinate as fuel additives using heterogeneous solid superacidic catalysts: Efficacy and kinetic modeling

Chemical Engineering Journal

Volumn 243, Issue , 2014, Pages 556-563

  Yadav, Ganapati D ^a   Yadav, Akhilesh R ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Alkyl levulinate; Biomass catalysis; Fuel additives; Green chemistry; Levulinic acid; Solid superacid

Indexed keywords

EID: 84894036141     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2014.01.013     Document Type: Article

References (41)

1. Klass D.L. Biomass for Renewable Energy, Fuels, and Chemicals 1998, Elsevier Inc., Amsterdam.
2. Corma A., Iborra S., Velty A. Chemical routes for the transformation of biomass into chemicals. Chem. Rev. 2007, 107:2411-2502.
3. Biorefinery: From Biomass to Chemicals and Fuels 2012, Walter De Gruyter Inc. M. Aresta, A. Dibenedetto, F. Dumeignil (Eds.).
4. Naik S.N., Goud V.V., Rout P.K., Dalai A.K. Production of first and second generation biofuels: a comprehensive review. Renew. Sus. Energy Rev. 2010, 14:578-597.
5. Yang F., Liu Q., Bai X., Du Y. Conversion of biomass into 5-hydroxymethylfurfural using solid acid catalyst. Bioresour. Technol. 2011, 102:3424-3429.
6. Zhao H.B., Holladay J.E., Brown H., Zhang Z.C. Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural. Science 2007, 316:1597-1600.
7. Chinnappan A., Kim H. Environmentally benign catalyst: synthesis, characterization, and properties of pyridinium dicationic molten salts (ionic liquids) and use of application in esterification. Chem. Eng. J. 2012, 187:283.
8. Yi Y.B., Ha M.G., Lee J.W., Chung C.H. New role of chromium fluoride: its catalytic action on the synthesis of hydroxymethylfurfural in ionic liquid using raw plant biomass and characterization of biomass hydrolysis. Chem. Eng. J. 2012, 180:370-375.
9. Liu B., Zhang Z., Zhao Z.K. Microwave-assisted catalytic conversion of cellulose into 5-hydroxymethylfurfural in ionic liquids. Chem. Eng. J. 2013, 215-216:517-521.
10. Olson E.S., Kielden M.R., Schlag A.J., Sharma R.K. Carbohydrates as organic raw materials. ACS Symp. Ser. 2001, 784:51-56.
11. Yadav G.D., Yadav A.R. Insight into esterification of eugenol to eugenol benzoate using a solid superacidic modified zirconia catalyst UDCaT-5. Chem. Eng. J. 2012, 192:146-155.
12. Yadav G.D., Mehta P.H. Heterogeneous catalysis in esterification reactions: preparation of phenethyl acetate and cyclohexyl acetate by using a variety of solid acidic catalysts. Ind. Eng. Chem. Res. 1994, 33(9):2198-2208.
13. Harmon M.E., Ferrell W.K., Franklin J.F. Effects on carbon storage of conversion of old-growth forests to young forests. Science 1990, 247:699-702.
14. Biorefinery Systems - An Overview Biorefineries - Industrial Processes and Products: Status Quo and Future Directions, vol. 1 2006, Wiley-VCH, Weinheim. B. Kamm, M. Kamm, P.R. Gruber, S. Kromus (Eds.).
15. Timokhim B.V., Baransky V.A., Eliseeva G.D. Levulinic acid in organic synthesis. Russ. Chem. Rev. 1999, 68:73-84.
16. Kitano M., Tanimoto F., Okabayashi M. Levulinic acid, a new chemical raw material. Chem. Econ. Eng. Rev. 1975, 7:25-29.
17. Leonard R.H. Levulinic acid as a basic chemical raw material. Ind. Eng. Chem. 1956, 48:1331-1341.
18. Khusnutdinov R.I., Baiguzina A.R., Smirnov A.A., Mukminov R.R., Dzhemilev U.M. Furfuryl alcohol in synthesis of levulinic acid esters and difurylmethane with Fe and Rh complexes. Russ. J. Appl. Chem. 2007, 80:1687-1690.
19. Bozell J.J., Moens L., Elliott D.C., Wang Y., Neuenscwander G.G., Fitzpatrick S.W., Bilski R.J., Jarnefeld J.L. Production of levulinic acid and use as a platform chemical for derived products. Resour. Conserv. Recy. 2000, 28:227-239.
20. P.M. Ayoub, Process for the reactive extraction of levulinic acid, 2005, WO Patent 2005070867.
21. Corma A., García H. Lewis acids: from conventional homogeneous to green homogeneous and heterogeneous catalysis. Chem. Rev. 2003, 103:4307-4365.
22. Yadav G.D., Thathagar M.B. Esterification of maleic acid with ethanol over cation exchange resin catalysts. React. Func. Polym. 2002, 52:99-110.
23. Penga L., Lina L., Zhanga J., Shia J., Liub S. Solid acid catalyzed glucose conversion to ethyl levulinate. Appl. Catal. A Gen. 2011, 397:259-265.
24. Kozhevnikov I.V. Heteropoly acids and related compounds as catalysts for fine chemical synthesis. Catal. Rev. Sci. Eng. 1995, 37:311-352.
25. Yadav G.D. Synergism of clay and heteropoly acids as nanocatalysts for development of green processes with potential industrial applications. Catal. Surveys Asia 2005, 9(2):117-137.
26. Yadav G.D., Nair J.J. Sulfated zirconia and its modified versions as promising catalysts for industrial processes. Micro. Meso. Mater. 1999, 33:1-48.
27. Yadav G.D., Goel P.K. A new efficient catalyst UDCaT-1 for the alkylation of ethylbenzene with ethanol to diethyl benzene. Clean Tech. Environ. Policy 2002, 4:165-170.
28. Yadav G.D., Nair J.J. Isomerization of citronellal to isopulegol using eclectically engineered sulfated zirconia-carbon molecular sieve composite catalysts, UDCaT-2. Langmuir 2000, 16:4072-4079.
29. Yadav G.D., Murkute A.D. Preparation of novel catalyst UDCaT-5: enhancement in activity of acid treated zirconia-effect of treatment with chlorosulfonic acid vis-a-vis sulfuric acid. J. Catal. 2004, 224:218-223.
30. Yadav G.D., Murkute A.D. Development of novel mesoporous catalystUDCaT-6: kinetics of synthesis of tert-amyl methyl ether (TAME) from tert-amyl alcohol and methanol. J. Phys. Chem. A 2004, 108:9557-9566.
31. Yadav G.D., Pathre G.S. Novel mesoporous solid acid catalysts: activity and selectivity in the synthesis of thymol by isopropylation of m-cresol with isopropanol over UDCaT-4, 5 and 6. J. Phys. Chem. A 2005, 109:11080-11088.
32. Yadav G.D., Murkute A.D. A novel efficient mesoporous solid acid catalyst UDCaT-4: dehydration of isopropanol and alkylation of mesitylene. Langmuir 2004, 20:11607-11619.
33. Yadav G.D., Murkute A.D. Preparation of novel mesoporous solid acid catalyst UDCaT-4 via synergism of persulfated alumina and zirconia into hexagonal mesoporous silica for alkylation reactions. Adv. Synth. Catal. 2004, 346:389-394.
34. Yadav G.D., Ajgaonkar N.P., Varma A. Preparation of highly superacidic sulfated zirconia via combustion synthesis and its application in Pechmann condensation of resorcinol with ethyl acetoacetate. J. Catal. 2012, 292:99-110.
35. Yadav G.D., Sharma R.V., Katole S.O. Selective dehydration of glycerol to acrolein: development of efficient and robust solid acid catalyst MUICaT-5. Ind. Eng. Chem. Res. 2013, 52(30):10133-10144.
36. Yadav G.D., Doshi N.S. Alkylation of hydroquinone with methyl-tertbutyl ether and tert-butanol. Catal. Today 2000, 60:263-273.
37. Yadav G.D., Sengupta S. Friedel-crafts alkylation of diphenyl oxide with benzyl chloride over sulphated zirconia. Org. Proc. Res. Dev. 2002, 6:256-262.
38. Yadav G.D., Doshi N.S. Synthesis of linear phenyldodecanes by the alkylation of benzene with 1-dodecene over non-zeolitic catalysts. Org. Proc. Res. Dev. 2002, 6:263-272.
39. Yadav G.D., Krishnan M.S. Etherification of beta-naphthol with alkanols using modified clays and sulfated zirconia. Ind. Eng. Chem. Res. 1998, 37:3358-3365.
40. Fogler H.S. Elements of Chemical Reaction Engineering 1995, Prentice-Hall, New Delhi. second ed.
41. Reid R.C., Prausnitz M.J., Sherwood T.K. The Properties of Gases and Liquids 1977, McGraw-Hill, New York. third ed.