Friedel-Crafts green alkylation of xylenes with tert-butanol over mesoporous superacid UDCaT-5

Chemical Engineering Research and Design

Volumn 90, Issue 9, 2012, Pages 1322-1334

  Yadav, Ganapati D ^a   Kamble, Shashikant B ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Friedel Crafts green alkylation; Green chemistry; Sulfated zirconia; Tert Butyl xylenes; UDCaT 5

Indexed keywords

EXPERIMENTAL DATA; FRIEDEL-CRAFTS; GREEN CHEMISTRY; HIGH SULFUR CONTENTS; LIQUID PHASE; M-XYLENE; MESOPOROUS; O-XYLENE; OPERATING PARAMETERS; OPTIMUM REACTION CONDITIONS; P-XYLENE; REACTION PATHWAYS; REACTION TEMPERATURE; SECOND ORDER KINETICS; SULFATED ZIRCONIA; SUPERACID; SYNERGISTIC EFFECT; SYSTEMATIC INVESTIGATIONS; TERT BUTANOL; TETRAGONAL PHASE; UDCAT-4; UDCAT-5; UDCAT-6;

ACIDS; ALCOHOLS; ALKYLATION; CATALYST ACTIVITY; INTEGRAL EQUATIONS; REUSABILITY; ZIRCONIA;

XYLENE;

EID: 84865551521     PISSN: 02638762     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cherd.2011.12.005     Document Type: Article

References (43)

1. Adam F., Ahmed A.E. The benzylation of xylenes using heterogeneous catalysts from rice husk ash silica modified with gallium, indium and iron. Chem. Eng. J. 2008, 145:328-334.
2. Clark J.H., Macquarrie D.J. Heterogeneous catalysis in liquid phase transformations of importance in the industrial preparation of fine chemicals. Org. Process Res. Dev. 1997, 1:149-162.
3. Clark J.H., Monks G.L., Nightingale D.J., Price P.M., White J.F. A new solid acid-based route to linear alkylbenzenes. J. Catal. 2000, 193(2):348-350.
4. Corma A. Inorganic solid acids and their use in acid-catalyzed hydrocarbon reactions. Chem. Rev. 1995, 95:559-614.
5. Corma C., Garcia H. Lewis acids: from conventional homogeneous to green homogeneous and heterogeneous catalysis. Chem. Rev. 2003, 103:4307-4366.
6. Derfer J.M., Derfer M.M. Kirk-Othmer Encyclopedia of Chemical Technology, vol. 22 1978, Wiley-Interscience, New York, p. 742.
7. Fiege H., Bayer A., Leverkusen G. Ullmann's Encyclopedia of Industrial Chemistry 1991, Wiley-VCH Verlag GmbH, Weinheim, Germany. 5th ed.
8. Fogler H.S. Elements of Chemical Reaction Engineering 1995, Prentice-Hall, New Delhi, India. 2nd ed.
9. Franck H.G., Stadelhofer J.W. Industrial Aromatic Chemistry 1988, Springer, Berlin.
10. Golay S., Wolfrath O., Doepper R., Renken A. Dynamics of Surface and Reaction Kinetics in Heterogeneous Catalysis, vol. 109 1997, Elsevier, Amsterdam, p. 295.
11. Gracia M.J., Losada E., Luque R., Campelo J.M., Luna D., Marinas J.M., Romero A.A. Activity of Gallium and Aluminum SBA-15 materials in the Friedel-Crafts alkylation of toluene with benzyl chloride and benzyl alcohol. Appl. Catal. A: Gen. 2008, 349:148-155.
12. Isakov Y.L., Minachev K.M., Kalinin V.P., Isakova T.A. Selective alkylation of xylenes by alcohols on zeolite catalysts. Russ. Chem. Bull. 1996, 45:2763-2768.
13. Kumbhar P.S., Yadav G.D. Catalysis by sulfur-promoted superacidic zirconia: condensation reactions of hydroquinone with aniline and substituted anilines. Chem. Eng. Sci. 1989, 44:2535-2544.
14. Lorenc J.F., Lambeth G., Scheffer W. Kirk-Othmer Encyclopedia of Chemical Technology, vol. 2 1992, Wiley-Interscience, New York.
15. Olah G.A. Friedel-Crafts and Related Reactions 1963, Wiley-Interscience, New York.
16. Olah G.A., Krishnamuri R., Suryaprakash G.K. Comprehensive Organic Synthesis, vol. 3 1991, Pergamon, Oxford, (Chapter 1.8).
17. Reid R.C., Prausnitz M.J., Sherwood T.K. The Properties of Gases and Liquids 1977, McGraw-Hill, New York. 3rd ed.
18. Rouge A., Spoetzl B., Gebauer K., Schenk R., Renken A. Microchannel reactors for fast periodic operation: the catalytic dehydration of isopropanol. Chem. Eng. Sci. 2001, 56:1419-1427.
19. Sheldon R.A., Downing R.S. Heterogeneous catalytic transformations for environmentally friendly production. Appl. Catal. A: Gen. 1999, 189:163-183.
20. Sheldon R.A., van Bekkum H. Fine Chemicals through Heterogeneous Catalysis 2001, Wiley-Interscience, Weinheim, Toronto.
21. Song C., Kirby S. Shape-selective alkylation of naphthalene with isopropanol over mordenite catalysts. Microporous Mater. 1994, 2:467-476.
22. van Bekkum H., Hoefnagel A.J., Vankoten M.A., Gunnewegh E.A., Vogt A.H.G., Kouwenhoven H.W. Zeolite catalyzed aromatic acylation and related reaches. Stud. Surf. Sci. Catal. 1994, 83:379-390.
23. Wilson K., Shorrock J.K., Renson A., Hoyer W., Gosselin B., Macquarrie D.J., Clark J.H. Novel supported solid acid catalysts for environmentally friendly organic synthesis. Stud. Surf. Sci. Catal. 2000, 130:3429-3434.
24. Yadav G.D. Synergism of clay and heteropoly acids as nano-catalysts for the development of green processes with potential industrial applications. Catal. Surv. Asia 2005, 9:117-137.
25. Yadav G.D., Asthana N.S. Kinetics and mechanism of selective mono-acylation of mesitylene. Ind. Eng. Chem. Res. 2002, 41:5565-5575.
26. Yadav G.D., Bokade V.V. Novelties of heteropolyacid supported on clay: Etherification of phenethyl alcohol with alkanols. Appl. Catal. A: Gen. 1996, 147:299-323.
27. 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. 2002, 236:129-147.
28. Yadav G.D., Kamble S.B. Synthesis of carvacrol by Friedel-Crafts alkylation of o-cresol with isopropanol using superacidic catalyst UDCaT-5. J. Chem. Technol. Biotechnol. 2009, 84:1499-1508.
29. Yadav G.D., Kamble S.B. Selectivity engineering in isopropylation of mesitylene with isopropyl alcohol over cesium substituted heteropolyacid supported on K-10 clay. Clean Technol. Environ. Policy 2009, 11:447-457.
30. Yadav G.D., Kamble S.B. Friedel-Crafts alkylation of mesitylene with tert-butyl alcohol over novel solid acid catalyst UDCaT-5. Int. J. Chem. Reactor Eng. 2009, 7:A12. http://www.bepress.com/ijcre/vol7/A12.
31. Yadav G.D., Doshi N.S. Alkylation of aniline with methyl-tert-butyl ether (MTBE) and tert-butanol over solid acids: product distribution and kinetics. J. Mol. Catal. A: Chem. 2003, 194:195-209.
32. Yadav G.D., Manyar H.G. Novelties of synthesis of acetoveratrone using heteropolyacid supported on hexagonal mesoporous silica. Micropor. Mesopor. Mater. 2003, 63:85-96.
33. Yadav G.D., Murkute A.D. Novel efficient mesoporous solid acid catalyst UDCaT-4: dehydration of 2-propanol and alkylation of mesitylene. Langmuir 2004, 20:11607-11619.
34. Yadav G.D., Murkute A.D. Preparation of a novel catalyst UDCaT-5: enhancement in activity of acid-treated zirconia-effect of treatment with chlorosulfonic acid vis-à-vis sulfuric acid. J. Catal. 2004, 224:218-223.
35. Yadav G.D., Murkute A.D. Development of a novel mesoporous catalyst UDCaT-6: Kinetics of synthesis of tert-amyl methyl ether (TAME) from tert-amyl alcohol and methanol. J. Phys. Chem. A 2004, 108:9557-9566.
36. Yadav G.D., Nair J.J. Novelties of eclectically engineered sulfated zirconia and carbon molecular sieve catalysts in cyclisation of citronellal to isopulegol. Chem. Commun. 1998, 2369-2370.
37. Yadav G.D., Nair J.J. Sulfated zirconia and its modified versions as promising catalysts for industrial processes. Micropor. Mesopor. Mater. 1999, 33:1-48.
38. Yadav G.D., Nair J.J. Selectivity engineering in the nitration of chlorobenzene using eclectically engineered sulfated zirconia and carbon molecular sieve catalysts. Catal. Lett. 1999, 62:49-52.
39. Yadav G.D., Nair J.J. Isomerisation of citronellal to isopulegol using shape selective catalysts. Langmuir 2000, 16:4072-4079.
40. 40/K-10 clay. Ind. Eng. Chem. Res. 2005, 44:1706-1715.
41. Yadav G.D., Salgaonkar S.S. UDCaT-4: a novel mesoporous superacid catalyst in the selective synthesis of 4,4'-diisopropylbiphenyl by the isopropylation of biphenyl. Micropor. Mesopor. Mater. 2005, 80:129-137.
42. Yadav G.D., Thorat T.S. Role of benzyl ether in the inversion of reactivities in Friedel-Crafts alkylation of toluene by benzyl chloride and benzyl alcohol. Tetrahedron Lett. 1996, 37:5405-5408.
43. Yadav G.D., Pujari A.A., Joshi A.V. Alkylation of p-cresol with methyl-tert-butyl ether (MTBE) over a novel solid acid catalyst UDCaT-1. Green Chem. 1999, 1:269-274.