Ionic liquid as catalyst for solid-liquid phase transfer catalyzed synthesis of p-nitrodiphenyl ether

Industrial and Engineering Chemistry Research

Volumn 47, Issue 23, 2008, Pages 9081-9089

  Yadav, Ganapati D ^a   Motirale, Bhavana G ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; CATALYSIS; CATALYST SELECTIVITY; EQUILIBRIUM CONSTANTS; ETHERS; FUNCTIONS; ION EXCHANGE; ION EXCHANGERS; IONIZATION OF LIQUIDS; IONS; LIQUIDS; MATHEMATICAL MODELS; MICROWAVE IRRADIATION; MICROWAVES; ORGANIC COMPOUNDS; RATE CONSTANTS; REACTION KINETICS; REUSABILITY;

CATALYZED SYNTHESES; CONVENTIONAL HEATING; HIGH TEMPERATURES; LIQUID PHASE; PHASE TRANSFERS; POTASSIUM PHENOXIDES; UNCATALYZED REACTIONS;

IONIC LIQUIDS;

EID: 57949112177     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie800340j     Document Type: Article

References (52)

1. Rogers, R. D.; Seddon, K. R. Ionic Liquids: Progress and Prospects. ACS Symp. Ser. 2003, 856, 100-107.
2. Rogers, R. D., Seddon, K. R., Eds. Working Salts: Syntheses and Uses of Task-Specific Ionic Liquids: ACS: Washington, 2002; Vol. 818, pp 247-259.
3. Rogers, R. D., Seddon, K. R., Volkov, S., Eds. Green Industrial Applications of Ionic Liquids, NATO Science Series II: Mathematics, Physics, Chemistry. Kluwer: Dordrecht, 2002.
4. Earle, M. J.; Seddon, K. R.; McCormac, P. B. The First High Yield Green Route to a Pharmaceutical in a Room Temperature Ionic Liquid. Green Chem. 2000, 2, 261-262.
5. Allen, D.; Baston, G.; Bradley, A. E.; Gorman, T.; Haile, A.; Hamblett, I.; Hatter, J. E.; Healey, M. J. F.; Hodgson, B.; Lewin, R.; Lovell, K. V.; Newton, B.; Pitner, W. R.; Rooney, D. W.; Sers, D. K.; Seddon, R.; Sims, H. E.; Thied, R. C. An Investigation of the Radiochemical Stability of Ionic Liquids. Green Chem. 2002, 4, 152-158.
6. Kitazume, T. Organic Synthesis in Ionic Liquids. Kagaku Kogyo. 2000, 51, 437-444.
7. Welton, T. Room-temperature Ionic Liquids. Solvents for Synthesis and Catalysis. Chem. Rev. 1999, 99, 2071-2083.
8. Earle, M. J.; Seddon, K. R. Ionic Liquids, Green Solvents for the Future. Pure Appl. Chem. 2000, 72 (7), 1391-1398.
9. Rooney, D. W.; Seddon, K. R. Ionic liquids, in handbook of solvents; G. Wypych Chem Tech Publishing: Toronto, 2001.
10. (a) Seddon, K. R.; Hardacre, C.; McCauley, B. J. Catalyst Comprising Indium Salt Organic Ionic Liquid Process for Friedel- Crafts Reactions, World Pat., WO 03028883, 2003.
11. (b) Adams, C. J.; Earle, M. J.; Roberts, G.; Seddon, K. R. Fridel Crafts Reactions in Room Temperature Ionic Liquids. Chem. Commun. 1998, 19, 2097-2098.
12. (c) Earle, M. J.; Hakala, U.; McAuley, B. J.; Nieuwenhuyzen, M.; Ramani, A.; Seddon, K. R. Metal Bis{(trifluoromethyl)sulfonyl}amide Complexes: Highly Efficient Friedel-Crafts Acylation Catalysts. Chem. Commun. 2004, 12, 1368-1369.
13. Earle, M. J.; McCormac, P. B.; Seddon, K. R. Diels-Alder Reactions in Ionic Liquids: A Safe Recyclable Alternative to Lithium Perchloratediethyl ether Mixtures. Green Chem. 1999, 1, 23-25.
14. McNulty, J.; Capretta, A.; Wilson, J.; Dyck, J.; Adabeng, G.; Robertson, A. Suzuki Cross-Coupling Reactions of Aryl Halides in Phosphonium Salt Ionic Liquid under Mild Conditions. Chem. Commun. 2002, 1986-1987.
15. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. The Heck Reaction in Ionic Liquids: A Multiphasic Catalyst System. Org. Lett. 1999, 1, 997-1000.
16. Kaufmann, D. E.; Nouroozian, M.; Henze, H. Molten Salts as an Efficient Medium for Palladium Catalyzed C-C Coupling Reactions. Syn. Lett. 1996, 1091-1092.
17. Gerritismas, D.; Robertson, A. J.; McNulty, A. Capretta, Heck Reactions of Aryl Halides in Phosphonium Salt Ionic Liquids. Library Screening and Applications. Tetrahedron Lett. 2004, 45, 7629-7631.
18. Winterton, N.; Seddon, K. R.; Patell, Y. Halogenation of Unsaturated Hydrocarbons in Ionic Liquids, World Pat., WO 0037400, 2000.
19. Hardacre, C.; Holbrey, J. D.; Katdare, S. P.; Seddon, K. R. Alternating Copolymerisation of Styrene and Carbon Monoxide in Ionic Liquids. Green Chem. 2002, 4, 143-146.
20. Adams, C. J.; Earle, M. J.; Seddon, K. R. Catalytic Cracking Reactions of Polyethylene to Light Alkanes in Ionic Liquids. Green Chem. 2000, 2 (1), 21-24.
21. Seddon, K. R. A. Stark, Selective Catalytic Oxidation of Benzyl Alcohol and Alkylbenzenes in Ionic Liquids. Green Chem. 2002, 4 (2), 119-123.
22. Dyson, P. J.; Ellis, D. J.; Parker, D. G.; Welton, T. Arene Hydrogenation in a Room-Temperature Ionic Liquid Using a Ruthenium Cluster Catalyst. Chem. Commun. 1999, 1, 25-26.
23. Gorodetsky, B.; Ramnial, T.; Brenda, N. R.; Clyburne, J. Electrochemical Reduction of an Imidazolium Cation: A Convenient Preparation of Imidazol-2-Ylidenes and Their Observation in an Ionic Liquid. Chem. Commun. 2004, 17, 1972-1973.
24. Gowda, G.; Chen, H.; Khetrapal, C.; Weiss, R. Amphotropic Ionic Liquid Crystals with Low Order Parameters. Chem. Mater. 2004, 16, 2101-2106.
25. Van, R. F.; Lau, R. M.; Sheldon, R. A. Biocatalytic Transformations in Ionic Liquids Trends In Biotechnology. Biotechnology 2003, 21, 131-138.
26. Bradaric, C. J.; Downard, A.; Kennedy, C. A.; Robertson, J.; Yuehui, Z. Industrial Preparation of Phosphonium Ionic Liquids. Green Chem. 2003, 5, 143-152.
27. Earle, M. J.; Katdare, S. P.; Seddon, K. R. The First Use of Ionic Liquids to Dramatically Influence the Outcome of Chemical Reactions. Org. Lett. 2004, 6, 707-710.
28. Earle, M. J.; McCormac, P. B.; Seddon, K. R. Diels-Alder Reactions in Ionic Liquids: A Safe Recyclable Alternative to Lithium Perchlorate-Diethyl Ether Mixtures. Green Chem. 1999, 1, 23-25.
29. Klingshirn, M. A.; Rogers, R. D.; Shaughnessy, K. H. Palladium-Catalyzed Hydroesterification of Styrene Derivatives in the Presence of Ionic Liquids. J. Organomet. Chem. 2005, 690, 3620-3636.
30. 2 Immobilized in Ionic Liquids. Tetrahedron 2005, 61, 9541-9544.
31. Picquet, M.; Stutzmann, S.; Tkatchenko, I.; Tommasi, I.; Zimmermann, J.; Wasserscheid, P. Selective Palladium-Catalysed Dimerisation of Methyl Acrylate in Ionic Liquids: Towards a Continuous Process. Green Chem. 2003, 5, 153-162.
32. Stark, C. M. Phase-transfer catalysis. I. Heterogeneous Reactions Involving Anion Transfer by Quaternary Ammonium and Phosphonium Salts. J. Am. Chem. Soc. 1971, 93, 195-199.
33. Cull, S. G.; Holbrey, J. D.; Vargas-Mora, V.; Seddon, K. R.; Lye, G. J. Room Temperature Ionic Liquids as Replacements or Organic Solvents in Multiphase Bioprocess Operations. Biotechnol. Bioeng. 2000, 69, 227-233.
34. Gupta, R. L.; Dey, D. K.; Juneja, T. R. Mutagenicity of 4-Nitrodiphenyl Ether and Its Metabolites. Toxicol. Lett. 1986, 34 (1), 13-21.
35. Tozaburo, K.; Katsuo, R. Local Anesthetics: Henoxy dialkyl amino cylanilide Derivative. Ann. Rept. Tohoku Coll. Pharma. 1956, 3, 63 CA; 51: 5718d.
36. Hamada, Y.; Matsuoka, H.; Hachisuka, Y.; Wakayama, T.; Kawase, T.; Sugiura, M. Studies on Chemotherapeutics ix. Antimicrobial Activity and Synthesis of Haloacetamidodiphenyl Ether Compounds and Haloacetamido Diphenyl Sulfide Compounds. Yakugahu Zasshi 1976, 96 (11), 1271. CA; 86: 1209184y.
37. Varma, R. S.; Kapoor, A. Synthesis of 4-(3-Benzalzolylmethyl)- Aminodiphenyl Ethers and Other Related Products as Potential Antimicrubial Agents. Pharmazie. 1980, 35 (2), 78. CA; 93: 114376c.
38. Jones, W. J.; Gannett, T. P. Dinitrodiphenyl Ether, US 4558164, 1985. CA, 104: 12623a.
39. Brewster, R. Q.; Groening, T. p- Nitrodiphenyl Ether. Org. Syn. Coll. 1943, 2, 445-446.
40. Rebeiro, G. L.; Khadilkar, B. M. Microwave Assisted Aromatic Nucleophilic Substitution Reaction Under Solvent Less Condition. Syn. Commun. 2003, 33 (8), 1405-1410.
41. Mil'to, V. I.; Yu, G. S.; Mironov, O. V.; Kopeikin, V. V. Kinetics of The Reactions of 4-Nitrochlorobenzene with Substituted Phenolates in an Aprotic Polar Solvent. Kinetics Catal. 2001, 42 (4), 466-470.
42. Mil'to, V. I.; Yu, G. S.; Mironov, O. V.; Kopeikin, V. V. Kinetics of the Reactions of 4-Nitrochlorobenzenew with Substituted Phenols in the Presence of Potassium Carbonate. Kinetics Catal. 2001, 42 (4), 471-473.
43. Mckillop, A.; Fiaud, J. C.; Hug, R. P. The Use of Phase-Transfer Catalysis for the Synthesis of Phenol Ethers. Tetrahedron 1974, 30, 1379-1382.
44. Yadav, G. D.; Desai, N. M. Novelties of Low Energy Microwave Irradiation in Tri-Phase vis-à-vis Bi-Liquid Phase Transfer Catalysis in Selective Etherification Aromatic Phenols. Catal. Commun. 2006, 7, 325-330.
45. Futano, M. D. Preparation of Nitro Substituted Diphenyl Ethers, US Patent 4287372, 1981.
46. Paradisi, C.; Quintily, U.; Scorrano, G. Anion Activation in the Synthesis of Ethers from Oxygen Anions and 1-Chloro-4-Nitrobenzene. J. Org. Chem. 1983, 48, 3022-3026.
47. Tundo, P.; Vnturello, E. E.; Angeletti, P. Phase-Transfer Catalysts Immobilized and Adsorbed on Alumina and Silica Gel. J. Am. Chem. Soc. 1982, 104, 6551-6555.
48. Yadav, G. D.; Subramanian, S. Novelties of solid-liquid phase transfer catalyzed synthesis of o-nitrodiphenyl ether. J. Mol. Catal. A: Chem. 2004, 209, 75.
49. Yadav, G. D.; Purandare, S. A. Novelties of selective synthesis of 3-methyl-4-nitro-diphenylether under solid-liquid phase transfer catalysis. J. Mol. Catal. A: Chem. 2005, 237, 60-66.
50. Yadav, G. D.; Desai, N. M. Novelties of low energy microwave irradiation in tri-phase vis-aÌ-vis bi-liquid phase-transfer catalysis in selective etherification of aromatic phenols. Catal. Commun. 2006, 7 (6), 325-330.
51. Yadav, G. D.; Bisht, P. M. Fundamental analysis of microwave irradiated liquid-liquid phase transfer catalysis (MILL-PTC): Simultaneous measurement of rate and exchange equilibrium constants in selective O-alkylation of p-tert-butylphenol with benzyl chloride. J. Mol. Catal. A: Chem. 2005, 236 (1-2), 54-64.
52. Yadav, G. D.; Bisht, P. M. Novelties of microwave irradiated solid-liquid phase transfer catalysis (MISL-PTC) in synthesis of 2′- benzyloxyacetophenon. J. Mol. Catal. A: Chem. 2004, 221 (1-2), 59-69.