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Korean Journal of Chemical Engineering, Vol.20, No.1, 39-43, 2003
Diphenylmethane Synthesis Using Ionic Liquids as Lewis Acid Catalyst
Friedel-Crafts alkylation of benzene with benzyl chloride was studied by using organochloroaluminate ionic liquids as Lewis acid catalyst. The reaction was performed in the temperature range of 40 to 70 ℃ at benzene/benzyl chloride=17, where selectivity to diphenylmethane was high. The optimum AlCl3/BMIC ratio of the ionic liquid for the benzylation reaction was 2. Superior performance was obtained with butyl group constituting the cationic species of the ionic liquid. Stirring speed had a major impact on catalytic activity of the BMIC-AlCl3 ionic liquid; benzyl chloride conversion decreased substantially from 98 to 68% as stirring speed was reduced from 900 to 500 rpm, and eventually no reaction took place at 200 rpm. BMIC-AlCl3 ionic liquid was more active than Fe-MCM-41 at the expense of a small drop in selectivity but still higher than 96% selectivity was obtained. The ionic liquid could be easily
recovered after phase separation. The performance of BMIC-AlCl3 ionic liquid was maintained after the second run with 97.4% conversion and 95.6% selectivity, but a sudden drop in activity was observed after the third run with only 26.8% conversion.
[References]
- Adams CJ, Earle MJ, Roberts G, Seddon KR, Chem. Commun., 2097, 1998
- Bonhote P, Dias AP, Papageorgiou N, Kalyanasundaram K, Gratzel M, Inorg. Chem., 35(5), 1168, 1996
- Chauvin Y, Olivier-Bourbigou H, Chemtech., Sep., 26, 1995
- Clark JH, Rhodes CN, "Clean Synthesis Using Porous Inorganic Solid Catalysts and Supported Reagents," The Royal Society of Chemistry, Cambridge, UK, 2000
- Chung YM, Ahn WS, Lim PK, J. Catal., 173(1), 210, 1998
- Earle MJ, McCormac PB, Seddon KR, Chem. Commun., 2245, 1998
- Freemantle M, Chem. Eng. News, 76(13), 32, 1998
- Gondos G, Kapocsi I, J. Phys. Chem. Solids, 57, 855, 1996
- Gordon CM, Holbrey JD, Kennedy AR, Seddon KR, J. Mater. Chem., 8, 2627, 1998
- He NY, Bao SL, Xu QH, Appl. Catal. A: Gen., 169(1), 29, 1998
- Huddlestone JG, Willauer HD, Swatloski RP, Visser AE, Rogers RD, Chem. Commun., 1756, 1998
- Koyande SN, Jaiswal RG, Jayaram RV, Ind. Eng. Chem. Res., 37(3), 908, 1998
- Lee CW, Tetrahedron, 40, 2461, 1999
- Marsh KN, Deev A, Wu ACT, Tran E, Klamt A, Korean J. Chem. Eng., 19(3), 357, 2002
- Pai SG, Bajpai AR, Deshpande AB, Samant SD, Synth. Commun., 27, 2267, 1997
- Shbrir F, "Alkylation Reaction Using Supported Ionic Liquid Catalyst," WO 99/03163, 1999
- Simon LC, Dupont J, de Souza RF, Appl. Catal. A: Gen., 175(1-2), 215, 1998
- Singh AP, Pandey AK, Catal. Lett., 60(3), 157, 1999
- Welton T, Chem. Rev., 99(8), 2071, 1999
- Wilkes JS, Levisky JA, Wilson RA, Hussey CL, Inorg. Chem., 21, 1263, 1982
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- Ahn JY, Shim HL, Kim KH, Kim I, Park SW, Park DW, Korean Journal of Chemical Engineering, 25(4), 693, 2008
- Zhang J, Huang C, Chen B, Li J, Li Y, Korean Journal of Chemical Engineering, 25(5), 982, 2008
- Lee MK, Shim HL, Dharman MM, Kim KH, Park SW, Park DW, Korean Journal of Chemical Engineering, 25(5), 1004, 2008
- Yu JI, Ju HY, Kim KH, Park DW, Korean Journal of Chemical Engineering, 27(2), 446, 2010
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