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Platinum nanoparticle catalysed coupling of phenol derivatives with 4-aminoantipyrine in aqueous medium

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Abstract

The oxidative coupling of phenols with 4-aminoantipyrine (AmNH2) has been studied by UV–visible spectroscopy using platinum nanoparticles as catalyst. The rate of antipyrilquinoneimine dye formation depends on the nature of substrates, temperature, pH, and the use of microheterogeneous media such as sodium dodecylsulphate (SDS), cetyl trimethylammonium bromide (CTAB) and Triton X-100 (TX-100). The reactivity trend observed for differently substituted phenols follows the order: 3,5-dimethylphenol > phenol > o-chlorophenol > o-nitrophenol. The rate of dye formation is greater at acid pH than at basic pH and the optimum pH is 5.4. A reaction pathway is proposed, involving the activation of o-chlorophenol with AmNH2 by metal nanoparticles and concomitant reactions of free radicals. Transmission electron microscopy results show that the particle size is 20 nm for the platinum nanoparticles involved in catalysis.

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References

  1. Sharma RK, Sharman P, Maitra A (2003) J Colloid Interface Sci 265:134. doi:10.1016/S0021-9797(03)00463-6

    Article  CAS  Google Scholar 

  2. Mastikhin VM, Goncharova SN, Tapilin VM, Terskikh VV, Balzhiunimaev BS (1995) J Mol Catal A Chem 96:175. doi:10.1016/1381-1169(94)00019-0

    Article  CAS  Google Scholar 

  3. Burda C, Chen X, Narayanan R, El-Sayed MA (2005) Chem Rev 105:1025. doi:10.1021/cr030063a

    Article  CAS  Google Scholar 

  4. Prabhuram J, Wang X, Hui CL, Hsing I-M (2003) J Phys Chem B 107:11057. doi:10.1021/jp0357929

    Article  CAS  Google Scholar 

  5. Roucoux A, Schulz J, Patin H (2002) Chem Rev 102:3757. doi:10.1021/cr010350j

    Article  CAS  Google Scholar 

  6. Narayanan R, El-Sayed MA (2004) J Am Chem Soc 126:7194. doi:10.1021/ja0486061

    Article  CAS  Google Scholar 

  7. Atlanta GA (1999) Agency for toxic substances and disease registry (ATSDR) toxicological profile for chlorophenols. U.S. Department of Health and Human Services, Public Health Service, Atlanta

    Google Scholar 

  8. Mishra S, Singh V, Jain A, Verma KK (2001) Analyst 126:1663. doi:10.1039/b103008f

    Article  CAS  Google Scholar 

  9. Clark EA, Anliker R, Utzinger RO (1980) The handbook of environmental chemistry, vol 3A. Springer-Verlag, Berlin, pp 181–215

    Google Scholar 

  10. Villalobos DA, Buchanan ID (2002) J Environ Eng Sci 1:65. doi:10.1139/s01-003

    Article  CAS  Google Scholar 

  11. Nicell JA, Bewtra JK, Biswas N, Taylor E (1993) Water Res 27:1629. doi:10.1016/0043-1354(93)90127-4

    Article  CAS  Google Scholar 

  12. Laurenti E, Ghibaudi E, Ardissone S, Ferrari RP (2003) J Inorg Biochem 95:171. doi:10.1016/S0162-0134(03)00101-6

    Article  CAS  Google Scholar 

  13. Entezari MH, Petrier C (2004) Appl Catal B: Environ 53:257. doi:10.1016/j.apcatb.2004.01.025

    Article  CAS  Google Scholar 

  14. Groves JT (2001) J Porphyr Phthalocyan 4:350. doi :10.1002/(SICI)1099-1409(200006/07)4:4<350::AID-JPP249>3.0.CO;2-G

    Article  Google Scholar 

  15. Metelitza DI, Litvinchuk AK, Savenkova MI (1991) J Mol Catal 67:401. doi:10.1016/0304-5102(91)80052-5

    Article  Google Scholar 

  16. Vinodu MV, Padmanabhan M (2001) Proc Indian Acad Sci (Chem Sci) 113:1

    Article  CAS  Google Scholar 

  17. Degrand C, Limoges B, Martre AM, Schollhorn B (2001) Analyst 126:887. doi:10.1039/b100533m

    Article  CAS  Google Scholar 

  18. Zhang J, Tang Y, Xie J-Q, Song Z-R, Wang L, Hu C-W (2005) React Kinet Catal Lett 85:269. doi:10.1007/s11144-005-0270-x

    Article  CAS  Google Scholar 

  19. Rajendiran N, Santhanalakshmi J (2006) J Mol Catal A: Chem 245:185. doi:10.1016/j.molcata.2005.09.045

    Article  CAS  Google Scholar 

  20. Santhanalakshmi J, Kasthuri J, Rajendiran N (2006) J Mol Catal A: Chem 265:282

    Google Scholar 

  21. Yang J, Deivaraj TC, Too H-P, Lee JY (2004) Langmuir 20:4241. doi:10.1021/la0361159

    Article  CAS  Google Scholar 

  22. Bonet F, Delmas V, Grugeon S, Orbina RH, Silvert P-Y, Elhsissen KT (1999) Nanostruct Mater 11:1277. doi:10.1016/S0965-9773(99)00419-5

    Article  CAS  Google Scholar 

  23. Chen C-W, Arai K, Yamamoto K, Serizawa T, Akashi M (2000) Macromol Chem Phys 201:2811. doi :10.1002/1521-3935(20001201)201:18<2811::AID-MACP2811>3.0.CO;2-0

    Article  CAS  Google Scholar 

  24. Xie TM, Dyrssen D (1984) Anal Chim Acta 160:21. doi:10.1016/S0003-2670(00)84505-5

    Article  CAS  Google Scholar 

  25. Jana NR, Sau TK, Pal T (1999) J Phys Chem B 103:115. doi:10.1021/jp982731f

    Article  CAS  Google Scholar 

  26. Zheng X, Zhu L, Yan A, Wang X, Xie Y (2003) J Colloid Interface Sci 268:357. doi:10.1016/j.jcis.2003.09.021

    Article  CAS  Google Scholar 

  27. Li Y, Petroski J, EI-Sayed MA (2000) J Phy Chem B104:10956. doi:10.1021/jp002569s

    Google Scholar 

  28. Carvalho RH, Lemos F, Lemos M, Vojinovic V, Fonseca LP, Cabral JMS (2006) Bioprocess Biosyst 29:99. doi:10.1007/s00449-006-0057-0

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Engineering and Technology, S.R.M. University, Chennai, 603 203, India

    Jayapalan Kasthuri

  2. Department of Physical Chemistry, University of Madras, Guindy Campus, Chennai, 600 025, India

    Jayadevan Santhanalakshmi

  3. Department of Polymer Science, University of Madras, Guindy Campus, Chennai, 600 025, India

    Nagappan Rajendiran

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  1. Jayapalan Kasthuri
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  2. Jayadevan Santhanalakshmi
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  3. Nagappan Rajendiran
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Correspondence to Jayadevan Santhanalakshmi.

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Kasthuri, J., Santhanalakshmi, J. & Rajendiran, N. Platinum nanoparticle catalysed coupling of phenol derivatives with 4-aminoantipyrine in aqueous medium. Transition Met Chem 33, 899–905 (2008). https://doi.org/10.1007/s11243-008-9130-7

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