Application of modified clays in diazotization and azo coupling reactions in water

Alireza Najafi Chermahini; Maryam Doukheh; Hassan Zadeh Hassan; Mehdi Bostanian

Journal of Industrial and Engineering Chemistry, Vol.18, No.2, 826-833, March, 2012

DOI10.1016/j.jiec.2011.11.146 Export Citation

Application of modified clays in diazotization and azo coupling reactions in water

Alireza Najafi Chermahini^†, Maryam Doukheh, Hassan Zadeh Hassan, and Mehdi Bostanian

Department of Chemistry, Faculty of Science, Yasouj University, 75918-74831 Yasouj, Iran

E-mail:

Diazotization and diazo coupling reaction of a series of aromatic amines and activated aromatic compounds over eco-friendly modified clay catalysts are described. The reaction was catalyzed by modified montmorillonite K-10 including Cu2+, Fe3+, and Zn2+ metal ions. The versatility of this method was checked by using various amines and phenols, which showed reasonable yields of products. These inexpensive, noncorrosive and reusable catalysts were found to exhibit bifunctional catalytic properties for diazotization and diazo coupling reactions. The catalysts could be reused several times without significant loss of their catalytic reactivity.

Keywords:Diazotization;Azo dye;Modified clay;Montmorillonite K-10;Reusable catalyst

[References]

Waring DR, Hallas G, The Chemistry and Application of Dyes, Plenum, New York, (1990)
Zollinger H, Diazo Chemistry I, Aromatic and Heteroaromatic Compounds, VCH Publishers Ltd., New York (1994)
Katz HE, Singer KD, Sohn JE, Dirk CW, King LA, Gordon HM, J. Am. Chem. Soc., 109, 6561 (1987)
Wang S, Shen S, Xu H, Dyes Pigments., 44, 195 (2000)
Li XY, Wu YQ, Gu DH, Gan FX, Mater. Sci. Eng. B., 158, 53 (2009)
Gan FX, Hou LS, Wang GB, Liu HY, Mater. Sci. Eng. B., 76, 63 (2000)
Sabi Y, Tamada S, Iwamura T, Oyamada M, Bruder F, Oster R, Jpn. J. Appl. Phys., 42, 1056 (2003)
Chen ZM, Wu YQ, Gu DH, Gan FX, Dyes Pigments., 76, 624 (2008)
Kirkan B, Gup R, Turk. J. Chem., 32, 9 (2008)
Gaber M, Fayed TA, El-Daly S, El-Sayed YSY, Spectrochim. Acta A., 68, 169 (2007)
Garg HG, Sharma RA, J. Med. Chem., 12, 1122 (1969)
Heiss GS, Gowan B, Dabbs ER, FEMS Microbiol. Lett., 99, 221 (1992)
Katritzky, Pozharskii AF, Handbook of Heterocyclic Chemistry, 2nd ed., Pergammon/Elsevier Science, Oxford (2000)
Elguero J, Katritzky AR, Denisko OV, Adv. Heterocycl. Chem., 76, 1 (2000)
Revanasiddappa HD, Manju B, IL Farmaco., 56, 615 (2001)
Sakthivel S, Neppolin B, Shankar MV, Arabindo B, Palanichamy M, Murugesam V, Sol. Energy Mater. Sol. Cells., 77, 65 (2003)
Rageh NM, Spectrochim. Acta A., 60, 103 (2004)
Bratton AC, Marshall EK, J. Biol. Chem., 128, 537 (1939)
Nagaraja P, Yathirajan HS, Raju CR, Vasantha RA, Nagendra MS, Hemantha KMS, IL Farmaco., 58, 1295 (2003)
Saunders KH, Allen RLM, Aromatic Diazo Compounds, 3rd ed., Edward Arnold (Publishers) Ltd., London (1985)
Clark JH, Chemistry of Waste Minimization, Chapman and Hall, London (1995)
Dabbagh HA, Mansoori Y, Dyes Pigments., 54, 37 (2002)
Valizadeh H, Shomali A, Dyes Pigments., 92, 1138 (2012)
Velasco MI, Kinen CO, de Rossi RH, Rossi LI, Dyes Pigments., 90, 259 (2011)
Rahman ML, Tschierske C, Yusoff M, Silong S, Tetrahedron Lett., 46, 2303 (2005)
Clark JH, Catalysis of Organic Reactions by Supported Inorganic Reagents, VCH, New York (1994)
Okuhara T, Chem. Rev., 102(10), 3641 (2002)
Ben Achma R, Ghorbel A, Dafinov A, Medina F, Appl. Catal., A., 349, 42 (2008)
Varma RS, Tetrahedron., 58, 1235 (2002)
Shinde AB, Shrigadi NB, Samant SD, Appl. Catal. A: Gen., 276(1-2), 5 (2004)
Batista J, Pintar A, Ceh M, Catal. Lett., 43(1-2), 79 (1997)
Yin W, Shi M, Tetrahedron., 61, 10861 (2005)
Guelou E, Barrault J, Fournier J, Tatibouet JM, Appl. Catal. B: Environ., 44(1), 1 (2003)
Caudo S, Centi G, Genovese C, Perathoner S, Appl. Catal. B: Environ., 70(1-4), 437 (2007)
Damodaran B, Litka J, Malathy L, Synth. Commun., 33, 863 (2003)
Dabbagh HA, Teimouri A, Chermahini AN, Dyes Pigments., 73, 239 (2007)
Zarei A, Hajipour AR, Khazdooz L, Mirjalili BF, Chermahini AR, Dyes Pigments., 81, 240 (2009)
Chermahini AN, Teimouri A, Momenbeik F, Dalirnasab Z, Ghaedi A, Roosta M, J.Heterocycl. Chem., 47, 913 (2010)
Chermahini AN, Teimouri A, Moaddeli A, Heteroat. Chem., 22, 168 (2011)
Velasco MI, Kinen CO, Rossi RH, Rossi LI, Dyes Pigments., 44, 259 (2011)
Martino C, Lucedio G, Marino P, J. Chem. Soc. Perk. Trans., 2, 455 (1982)
Jacques P, Strub H, See J, Jean-Pierre F, Tetrahedron., 35, 2071 (1979)
Bauer FO, J. Prakt. Chem. (Leipzig)., 2, 261 (1917)
Carrara B, Gazz. Chim. Ital., 53, 289 (1923)
Butler RN, O’Shea PD, Shelly DP, J. Chem. Soc. Perk. Trans., 1, 1039 (1987)
Todres ZV, Ovsepyan GT, Ionina EA, Kosnikov AY, Lindeman SV, Struchkov YT, Bull. Acad. Sci. USSR, Div. Chem. Sci. 37 (1988) 1651 (English Translation) (Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1988; 1845-52).
Bhalerao NV, Panse DG, Bapat BV, Ghatge BB, Ind. J. Chem. B., 24, 327 (1985)
Heemstra JM, Moore JS, Tetrahedron., 60, 7287 (2004)
Auwers K, Michaelis F, Chem. Ber., 47, 1293 (1914)

[1] Waring DR, Hallas G, The Chemistry and Application of Dyes, Plenum, New York, (1990)

[2] Zollinger H, Diazo Chemistry I, Aromatic and Heteroaromatic Compounds, VCH Publishers Ltd., New York (1994)

[3] Katz HE, Singer KD, Sohn JE, Dirk CW, King LA, Gordon HM, J. Am. Chem. Soc., 109, 6561 (1987)

[4] Wang S, Shen S, Xu H, Dyes Pigments., 44, 195 (2000)

[5] Li XY, Wu YQ, Gu DH, Gan FX, Mater. Sci. Eng. B., 158, 53 (2009)

[6] Gan FX, Hou LS, Wang GB, Liu HY, Mater. Sci. Eng. B., 76, 63 (2000)

[7] Sabi Y, Tamada S, Iwamura T, Oyamada M, Bruder F, Oster R, Jpn. J. Appl. Phys., 42, 1056 (2003)

[8] Chen ZM, Wu YQ, Gu DH, Gan FX, Dyes Pigments., 76, 624 (2008)

[9] Kirkan B, Gup R, Turk. J. Chem., 32, 9 (2008)

[10] Gaber M, Fayed TA, El-Daly S, El-Sayed YSY, Spectrochim. Acta A., 68, 169 (2007)

[11] Garg HG, Sharma RA, J. Med. Chem., 12, 1122 (1969)

[12] Heiss GS, Gowan B, Dabbs ER, FEMS Microbiol. Lett., 99, 221 (1992)

[13] Katritzky, Pozharskii AF, Handbook of Heterocyclic Chemistry, 2nd ed., Pergammon/Elsevier Science, Oxford (2000)

[14] Elguero J, Katritzky AR, Denisko OV, Adv. Heterocycl. Chem., 76, 1 (2000)

[15] Revanasiddappa HD, Manju B, IL Farmaco., 56, 615 (2001)

[16] Sakthivel S, Neppolin B, Shankar MV, Arabindo B, Palanichamy M, Murugesam V, Sol. Energy Mater. Sol. Cells., 77, 65 (2003)

[17] Rageh NM, Spectrochim. Acta A., 60, 103 (2004)

[18] Bratton AC, Marshall EK, J. Biol. Chem., 128, 537 (1939)

[19] Nagaraja P, Yathirajan HS, Raju CR, Vasantha RA, Nagendra MS, Hemantha KMS, IL Farmaco., 58, 1295 (2003)

[20] Saunders KH, Allen RLM, Aromatic Diazo Compounds, 3rd ed., Edward Arnold (Publishers) Ltd., London (1985)

[21] Clark JH, Chemistry of Waste Minimization, Chapman and Hall, London (1995)

[22] Dabbagh HA, Mansoori Y, Dyes Pigments., 54, 37 (2002)

[23] Valizadeh H, Shomali A, Dyes Pigments., 92, 1138 (2012)

[24] Velasco MI, Kinen CO, de Rossi RH, Rossi LI, Dyes Pigments., 90, 259 (2011)

[25] Rahman ML, Tschierske C, Yusoff M, Silong S, Tetrahedron Lett., 46, 2303 (2005)

[26] Clark JH, Catalysis of Organic Reactions by Supported Inorganic Reagents, VCH, New York (1994)

[27] Okuhara T, Chem. Rev., 102(10), 3641 (2002)

[28] Ben Achma R, Ghorbel A, Dafinov A, Medina F, Appl. Catal., A., 349, 42 (2008)

[29] Varma RS, Tetrahedron., 58, 1235 (2002)

[30] Shinde AB, Shrigadi NB, Samant SD, Appl. Catal. A: Gen., 276(1-2), 5 (2004)

[31] Batista J, Pintar A, Ceh M, Catal. Lett., 43(1-2), 79 (1997)

[32] Yin W, Shi M, Tetrahedron., 61, 10861 (2005)

[33] Guelou E, Barrault J, Fournier J, Tatibouet JM, Appl. Catal. B: Environ., 44(1), 1 (2003)

[34] Caudo S, Centi G, Genovese C, Perathoner S, Appl. Catal. B: Environ., 70(1-4), 437 (2007)

[35] Damodaran B, Litka J, Malathy L, Synth. Commun., 33, 863 (2003)

[36] Dabbagh HA, Teimouri A, Chermahini AN, Dyes Pigments., 73, 239 (2007)

[37] Zarei A, Hajipour AR, Khazdooz L, Mirjalili BF, Chermahini AR, Dyes Pigments., 81, 240 (2009)

[38] Chermahini AN, Teimouri A, Momenbeik F, Dalirnasab Z, Ghaedi A, Roosta M, J.Heterocycl. Chem., 47, 913 (2010)

[39] Chermahini AN, Teimouri A, Moaddeli A, Heteroat. Chem., 22, 168 (2011)

[40] Velasco MI, Kinen CO, Rossi RH, Rossi LI, Dyes Pigments., 44, 259 (2011)

[41] Martino C, Lucedio G, Marino P, J. Chem. Soc. Perk. Trans., 2, 455 (1982)

[42] Jacques P, Strub H, See J, Jean-Pierre F, Tetrahedron., 35, 2071 (1979)

[43] Bauer FO, J. Prakt. Chem. (Leipzig)., 2, 261 (1917)

[44] Carrara B, Gazz. Chim. Ital., 53, 289 (1923)

[45] Butler RN, O’Shea PD, Shelly DP, J. Chem. Soc. Perk. Trans., 1, 1039 (1987)

[46] Todres ZV, Ovsepyan GT, Ionina EA, Kosnikov AY, Lindeman SV, Struchkov YT, Bull. Acad. Sci. USSR, Div. Chem. Sci. 37 (1988) 1651 (English Translation) (Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1988; 1845-52).

[47] Bhalerao NV, Panse DG, Bapat BV, Ghatge BB, Ind. J. Chem. B., 24, 327 (1985)

[48] Heemstra JM, Moore JS, Tetrahedron., 60, 7287 (2004)

[49] Auwers K, Michaelis F, Chem. Ber., 47, 1293 (1914)