Multiphase oxidation of aniline to nitrosobenzene with hydrogen peroxide catalyzed by heteropolyacids

Synlett

Volumn , Issue 7, 2008, Pages 967-970

  Tundo, P ^a,b   Romanelli, G P ^c   Vazquez P G ^c   Loris, A ^a   Arico F ^a  

^a Interuniversity Consortium 'Chemistry for the Environment'   (Italy)

^b CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

^c DEPARTAMENTO DE QUÍMICA   (Argentina)

Author keywords

Aniline; Hydrogen peroxide; Keggin polyoxometalate; Multiphase system; Oxidation

Indexed keywords

ACID; ANILINE; HYDROGEN PEROXIDE; NITROSOBENZENE;

ARTICLE; CATALYST; OXIDATION;

EID: 42949096132     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1072502     Document Type: Article

References (24)

1. Oppolzer, W.; Tamura, O.; Sundarabau, G.; Signer, M. J. Am. Chem. Soc. 1992, 114, 5900.
2. Adam, W.; Krebs, O. Chem. Rev. 2003, 103, 4131.
3. Viehe, H. G.; Merenly, R.; Francotte, E.; Van Meersche, M.; Germani, G.; Declerq, J. P.; Bodart-Gilmont, J. J. Am. Chem. Soc. 1977, 99, 2340.
4. Kopp, F.; Sapountzis, I.; Knochel, P. Synlett 2003, 885.
5. Goelitz, P.; de Meijere, A. Angew. Chem. 1977, 16, 854.
6. Rice, W. G.; Schaeffer, C. A.; Graham, L.; Bu, M.; McDougal, J. S.; Orloff, S. L.; Villinger, F.; Young, M.; Oroszlan, S.; Fesen, M. R.; Pommier, Y.; Mendeleyev, J.; Kun, E. Nature (London) 1993, 361, 473.
7. (a) Gowenlock, B. G.; Richter-Addo, G. B. Chem. Rev. 2004, 104, 3315.
8. (b) Yu, B.-C.; Shirai, Y.; Tour, J. M. Tetrahedron 2006, 62, 10303.
9. (c) Priewisch, B.; Ruck-Braun, K. J. Org. Chem. 2005, 70, 2350.
10. Zhu, Z.; Espenson, J. H. J. Org. Chem. 1995, 60, 1326.
11. Giera, H.; Lange, W.; Meiers, M.; Pires, R. Eur. Patent Appl., EP1099683A1, 2001.
12. (a) Tollari, S.; Cuscela, M.; Porta, F. J. Chem. Soc., Chem. Commun. 1993, 1510.
13. (b) Defoin, A. Synthesis 2004, 706.
14. Alizadeha, M. H.; Tayebee, R. J. Braz. Chem. Soc. 2005, 16, 108.
15. Okujara, T.; Mizuno, M. Appl. Catal. A: Gen. 2001, 222, 63.
16. Corma, A. Chem. Rev. 1995, 95, 559.
17. (a) Risono, M. Chem. Commun. 2001, 1141.
18. (b) Simonova, M. V.; Zhizhina, E. G.; Russkikh, V. V.; Matveev, K. I. Russ. Chem. Bull. 2005, 54, 1532.
19. Villabrille, P. I.; Romanelli, G. P.; Vàzquez, P. G.; Càceres, C. V. Appl. Catal. A: Gen. 2004, 270, 101.
20. Romanelli, G. P.; Vàzquez, P. G.; Tundo, P. Synlett 2005, 75.
21. Results not yet published.
22. 40 (M12P), was obtained from Aldrich. All the others were prepared according to conventional procedures described in ref. 16. Catalysts were characterized with a Bruker IFS 66 FT-IR equipment, employing KBr discs. The acidity was measured via potentiometric titration, adding little amounts of a solution of n-butylamine in MeCN (0.05 N) to the suspended solid (0.05 g) in MeCN (90 mL) stirred during the whole procedure. The difference of potential (mV) was recorded with a digital pHmeter (Instrumentalia S.R.L.), equipped with a combined electrode.
23. 2 (35% p/V, 5 mL) and heteropolyacid (2 mmol%). The reaction mixture was stirred with a magnetic bar at 700 rpm. General Procedure for Oxidation in Multiphasic Conditions: The aforementioned procedure was employed for reactions in multiphasic conditions, with the addition of Aliquat 336 (2.32 mL) in isooctane (10% p/V) solution and employing isooctane instead of MeCN as organic solvent. Samples Analysis: Samples were withdrawn from the organic phase at 20 min time intervals during a total reaction period of 420 min. Each sample volume was approximately 20 μL and it was diluted with 1-2 mL of isooctane or MeCN. The solution was stirred in the presence of silica gel and filtered to remove the Aliquat 336 before the injection in the GC. Concentrations were calculated with the internal standard method. Conversions were obtained with GC analysis performed with a Varian GC 3400 instrument, in the presence of n-decane as internal standard. The capillary column was a 30 m Chromopack CP Sil 8 CB, whose diameter was 0.32 mm. The identification of products was performed with GC-MS (detector HP 5971) for comparison with authentic samples.
24. Villabrille, P. I. PhD Thesis; Universidad Nacional de La Plata: Argentina, 2006.