Novel acidic ionic liquids catalytic systems for friedel-crafts alkylation of aromatic compounds with alkenes

Chemistry Letters

Volumn 33, Issue 4, 2004, Pages 472-473

  Qiao, Kun ^a   Yokoyama, Chiaki ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALKENE DERIVATIVE; AROMATIC COMPOUND; ION;

ACIDITY; ARTICLE; CATALYSIS; CHEMICAL REACTION; FRIEDEL CRAFTS REACTION; LIQUID; TEMPERATURE;

EID: 3142658251     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.472     Document Type: Article

References (16)

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2. For recent reviews on ionic liquids, see a) J. Dupont, R. F. de Souza, and P. A. Z. Suarez, Chem. Rev., 102, 3667 (2002). b) P. Wasserscheid and W. Keim, Angew. Chem., Int. Ed., 39, 3772 (2000). T. Welton, Chem. Rev., 99, 2071 (1999). C. M. Gordon, Appl. Catal., A, 222, 101 (2001). e) R. A. Sheldon, Chem. Commun., 2001, 2399.
3. For recent reviews on ionic liquids, see a) J. Dupont, R. F. de Souza, and P. A. Z. Suarez, Chem. Rev., 102, 3667 (2002). b) P. Wasserscheid and W. Keim, Angew. Chem., Int. Ed., 39, 3772 (2000). T. Welton, Chem. Rev., 99, 2071 (1999). C. M. Gordon, Appl. Catal., A, 222, 101 (2001). e) R. A. Sheldon, Chem. Commun., 2001, 2399.
4. For recent reviews on ionic liquids, see a) J. Dupont, R. F. de Souza, and P. A. Z. Suarez, Chem. Rev., 102, 3667 (2002). b) P. Wasserscheid and W. Keim, Angew. Chem., Int. Ed., 39, 3772 (2000). c) T. Welton, Chem. Rev., 99, 2071 (1999). C. M. Gordon, Appl. Catal., A, 222, 101 (2001). e) R. A. Sheldon, Chem. Commun., 2001, 2399.
5. For recent reviews on ionic liquids, see a) J. Dupont, R. F. de Souza, and P. A. Z. Suarez, Chem. Rev., 102, 3667 (2002). b) P. Wasserscheid and W. Keim, Angew. Chem., Int. Ed., 39, 3772 (2000). c) T. Welton, Chem. Rev., 99, 2071 (1999). d) C. M. Gordon, Appl. Catal., A, 222, 101 (2001). e) R. A. Sheldon, Chem. Commun., 2001, 2399.
6. For recent reviews on ionic liquids, see a) J. Dupont, R. F. de Souza, and P. A. Z. Suarez, Chem. Rev., 102, 3667 (2002). b) P. Wasserscheid and W. Keim, Angew. Chem., Int. Ed., 39, 3772 (2000). c) T. Welton, Chem. Rev., 99, 2071 (1999). d) C. M. Gordon, Appl. Catal., A, 222, 101 (2001). e) R. A. Sheldon, Chem. Commun., 2001, 2399.
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10. The experimental procedure for preparation of ionic liquids 1 is as follows: thionyl chloride (0.12 mol) was charged into a 50 mL two-neck flask with reflux and magnetic stirrer. Under reflux conditions, the Brønsted acidic ionic liquid 2 (0.1 mol), prepared according to reference 6, was slowly added into the flask, then the reaction was proceeded for another 8 h. Remove the unreacted thionyl chloride by distillation and the residual liquid was product. Then the product was further purified under vacuum at 50°C for 2 h. DTA analysis shows that the melting point of ionic liquid 1a and 1b are 219.8 and 211.8 K, respectively.
11. A. C. Cole, J. L. Jensen, I. Ntai, K. L. T. Tran, K. J. Weaver, D. C. Forbes, and J. H. Davis, Jr., J. Am. Chem. Soc., 124, 5962 (2002).
12. In a typical experiment, ionic liquid, aromatic compounds and alkene are charged into a 10 mL test tube with magnetic stirrer. Then the reaction is carried out at desired temperature for 5 to 24 h. After reaction, the components in the upper organic layer are analyzed by a gas chromatograph equipped with a FID detector (Shimadzu GC-14A, ULBON HR-52 capillary column 25 m x 0.32 mm).
13. B. S. Kwak and T. J. Kim, Catal. Lett., 59, 55 (1999), and references cited therein.
14. Lewis acidic ionic liquid 1b has also no activity for alkylation of benzene with 1-dodecene, cyclopentene and cyclohexene.
15. 3 (about 4% yield) are also examined.
16. O. Mouhtady, H. Gaspard-Iloughmane, N. Roques, and C. L. Roux, Tetrahedron Lett., 44, 6379 (2003).