Nanoparticles of organosilane-based nitrite ionic liquid immobilized on silica for the diazotization of aniline derivatives and subsequent synthesis of azo dyes

Dyes and Pigments

Volumn 92, Issue 3, 2012, Pages 1308-1313

  Valizadeh, Hassan ^a   Amiri, Mohammad ^a   Hosseinzadeh, Fatemeh ^a  

^a AZARBAIJAN SHAHID MADANI UNIVERSITY   (Iran)

Author keywords

Azo dyes; Azo coupling; Diazotization; Immobilized ionic liquid; Nanoparticle; Nitrite ionic liquid

Indexed keywords

ANILINE DERIVATIVES; AZO-COUPLING; DIAZONIUM SALTS; DIAZOTIZATION; EXCELLENT PERFORMANCE; EXPERIMENTAL PROCEDURE; GOOD YIELD; HETEROGENEOUS CONDITIONS; IMIDAZOLIUM; IMMOBILIZED IONIC LIQUID; IN-SITU; MODEL REACTIONS; N-METHYLIMIDAZOLE; NITRITE IONIC LIQUID; NITROSONIUM; ROOM TEMPERATURE; SHORT REACTION TIME; TRIMETHOXYSILANE;

ANILINE; AZO DYES; IONS; NANOPARTICLES; PHENOLS; SILICA; SYNTHESIS (CHEMICAL);

IONIC LIQUIDS;

EID: 80054069392     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2011.09.013     Document Type: Article

References (32)

1. N.T.S. Phan, M.V.D. Sluys, and C.W. Jones On the nature of the active species in palladium catalyzed Mizoroki-Heck and Suzuki-Miyaura couplings - homogeneous or heterogeneous catalysis, a critical review Adv Synth Catal 348 2006 609 679 (Pubitemid 43573698)
2. S.M. Lee, H.J. Yoon, J.H. Kim, W.J. Chung, and Y.S. Lee Highly active organosilane-based N-heterocyclic carbene-palladium complex immobilized on silica particles for the Suzuki reaction Pure Appl Chem 79 2007 1553 1559
3. T. Welton Room-temperature ionic liquids. Solvents for synthesis and catalysis Chem Rev 99 1999 2071 2083 and references cited therein (Pubitemid 129585179)
4. K. Gong, D. Fang, H.L. Wang, X.L. Zhou, and Z.L. Liu The one-pot synthesis of 14- alkyl- or aryl-14H-dibenzo[a, j]xanthenes catalyzed by task-specific ionic liquid Dye Pigments 80 2009 30 33
5. L. Wang, H. Li, and P. Li Task-specific ionic liquid as base, ligand and reaction medium for the palladium-catalyzed Heck reaction Tetrahedron 65 2009 364 368
6. D.E. Siyutkin, A.S. Kucherenko, M.I. Struchkova, and S.G. Zlotin A novel (S)-proline-modified task-specific chiral ionic liquid - an amphiphilic recoverable catalyst for direct asymmetric aldol reactions in water Tetrahedron Lett 49 2008 1212 1216
7. M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, and A. Zare 3-Methyl-1-sulfonic acid imidazolium chloride as a new, efficient and recyclable catalyst and solvent for the preparation of N-sulfonyl imines at room temperature J Iran Chem Soc 7 2010 646 651
8. A.R. Hajipour, F. Rafiee, and A.E. Ruoho A rapid and convenient method for the synthesis of aldoximes under microwave irradiation using in situ generated ionic liquids J Iran Chem Soc 7 2010 114 118
9. A.R. Hajipour, and F. Rafiee Basic ionic liquids. A short review J Iran Chem. Soc 6 2009 647 648
10. H. Valizadeh, and A. Shomali A new nitrite ionic liquid (IL-ONO) as a nitrosonium source for the efficient diazotization of aniline derivatives and in-situ synthesis of azo dyes Dye Pigments 92 3 2012 1138 1143
11. W.A. Herrmann, V.P.W. Bhm, C.W.K. Gstttmayr, M. Grosche, C.P. Reisinger, and T. Weskamp J Organomet Chem 616 2001 617 618
12. M.S. Sanford, J.A. Love, and R.H. Grubbs Mechanism and activity of ruthenium olefin metathesis catalysts J Am Chem Soc 123 2001 6543 6554 (Pubitemid 32916448)
13. A.K. Chatterjee, and R.H. Grubbs Synthesis of trisubstituted alkenes via olefin cross-metathesis Org Lett 1 1999 1751 1753
14. R. Sugimura, K. Qiao, D. Tomida, and C. Yokoyama Immobilization of acidic ionic liquids by copolymerization with styrene and their catalytic use for acetal formation Catal Commun 8 2007 770 772 (Pubitemid 46342007)
15. G. Wang, N. Yu, L. Peng, R. Tan, H. Zhao, and D. Yin Immobilized chloroferrate ionic liquid: an efficient and reusable catalyst for synthesis of diphenylmethane and its derivatives Catal Lett 123 2008 252 258
16. T.C. Kuo, R.L. Mc Creery, and G.M. Swain Electrochemical modification of boron-doped chemical vapor deposited diamond surfaces with covalently bonded monolayers Electrochem Solid-state Lett 2 1999 288 290
17. A. Adenier, M.C. Bernard, M.M. Chehimi, E. Cabet-Deliry, B. Desbat, and O. Fagebaume Covalent modification of iron surfaces by electrochemical reduction of aryldiazonium salts J Am Chem Soc 123 2001 4541 4549 (Pubitemid 32923382)
18. M.P. Stewart, F. Maya, D.V. Kosynkin, S.M. Dirk, J.J. Stapleton, and C.L. McGuiness Direct covalent grafting of conjugated molecules onto Si, GaAs, and Pd surfaces from aryldiazonium salts J Am Chem Soc 126 2004 370 378 (Pubitemid 38090377)
19. H.A. Dabbagh, A. Teimouri, and A.N. Chermahini Green and efficient diazotization and diazo coupling reactions on clays Dye Pigments 73 2007 239 244 (Pubitemid 44341037)
20. D.A. Gorlushko, V.D. Filimonov, E.A. Krasnokutskaya, N.I. Semenischeva, B.S. Go, and H.Y. Hwang Iodination of aryl amines in a water-paste form via stable aryl diazonium tosylates Tetrahedron Lett 49 2008 1080 1082
21. H. Faustino, R.M. El-Shishtawy, L.V. Reis, P.F. Santos, and P. Almeida 2-Nitrosobenzothiazoles: useful synthons for new azobenzothiazole dyes Tetrahedron Lett 49 2008 6907 6909
22. N.P. Noroozi, J. Khalafy, and Z. Malekpoor Can be azo dyes obtained by grinding under solvent-free conditions? J Chin Chem Soc 56 2009 1018 1027
23. E. Abdel-latif, and M.A. Metwally Waste-free solid-state organic syntheses: solvent-free alkylation heterocyclization, and azo-coupling reactions Monat für Chem 138 2007 771 776
24. J. Merrington, M. James, and M. Bradley Supported diazonium salts - convenient reagents for the combinatorial synthesis of azo dye Chem Commun 2002 140 141 (Pubitemid 34102071)
25. M.A. Zolfigol Silica sulfuric acid/NaNO2 as a novel heterogeneous system for production of thionitrites and disulfides under mild conditions Tetrahedron 57 2001 9509 9511 (Pubitemid 33016767)
26. A.R. Hajipour, B.B.F. Mirjalili, A. Zarei, L. Khazdooz, and A.E. Ruoho A novel method for sulfonation of aromatic rings with silica sulfuric acid Tetrahedron Lett 45 2004 6607 6609 (Pubitemid 39091866)
27. 2 as a novel heterogeneous system for the oxidation of 1,4-dihydropyridines under mild conditions Green Chem 4 2002 562 564
28. M.A. Zolfigol, B.B.F. Mirjalili, A. Bamoniri, M.A. Karimi, A. Zarei, and L. Khazdooz Nitration of aromatic compounds on silica sulfuric acid Bull Kor Chem Soc 25 2004 1414 1416
29. A.R. Hajipour, A. Zarei, L. Khazdooz, B.B.F. Mirjalili, N. Sheikhan, and S. Zahmatkesh Silica sulfuric acid as an efficient heterogeneous catalyst for the synthesis of 1,1-Diacetates under solvent-free conditions Synthesis 20 2005 3644 3648 (Pubitemid 43028685)
30. A.R. Hajipour, A. Zarei, and A.E. Ruoho Efficient method for iodination of alcohols using KI/silica sulfuric acid (SSA) Synth Commun 36 2006 1039 1050
31. S.A. Hameed Characterization and thermal decomposition of indolylidene aniline azo-dyes derivatives Jord J Chem 2 2007 133 144
32. H. Valizadeh, M. Amiri, A. Shomali, and F. Hosseinzadeh Ionic liquid 1-(3-trimethoxysilylpropyl)-3-methylimidazolium nitrite as a new reagent for the efficient diazotization of aniline derivatives and in situ synthesis of azo dyes J Iran Chem Soc 8 2011 495 501