화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Journal of Industrial and Engineering Chemistry, Vol.42, 53-62, October, 2016
DOI10.1016/j.jiec.2016.07.028  Export Citation
Selective heteroaromatic nitrogen base promoted chromium(VI) oxidation of isomeric pentanols in aqueous micellar media at room temperature
Pintu Sar, Aniruddha Ghosh, Susanta Malik, Dhiman Ray1, Bijan Das1, and Bidyut Saha†
  • Homogeneous Catalysis Laboratory, Department of Chemistry, The University of Burdwan, Burdwan 713104, India
  • 1Department of Chemistry, Presidency University, 86/1 College Street, Kolkata 700073, India
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Oxidation of the three isomeric pentanols by potassium dichromate in aqueous acidic medium was investigated spectrophotometrically at 25 °C. The oxidation leads to the formation of corresponding carbonyl products as identified by 1H NMR measurement and other techniques. The effects of cationic (cetylpyridinium chloride, CPCl), anionic (sodium dodecylsulphate, NaDS) and nonionic surfactant (polyoxyethylene octyl phenyl ether, TX-100) on reaction kinetics were studied. Moreover the catalytic effect of surfactant in presence of three heteroaromatic nitrogen bases: 2-picolinic acid (2-PA), 2,20-bipyridyl (2,20-bipy) and 1,10-phenanthroline (1,10-phen) on the oxidation were also investigated. The value of the rate constant in promoted and unpromoted reaction has been found to be higher in NaDS than in TX-100 and CPCl micellar medium. Conductivity and tensiometry measurements were carried out to determine critical micellization concentration and free energy of micellization (ΔGm°) of the used surfactant in presence of three pentanols. Among the different surfactant and promoter the combination of 2,20-bipy and NaDS is efficient to exhibit ~1000 fold rate enhancement for oxidation of 1-pentanol and it is ‘selective’ over the rest of two pentanols oxidation.
Keywords:Pentanol;Chromium(VI);Valeraldehyde;Metal-organic conjugate;Surfactant
  1. Sharma SK, Jasra RV, Indian J. Chem. Sect A-Inorg. Bio-Inorg. Phys. Theor. Anal. Chem., 54A, 451 (2015)
  2. Wang Y, Guo M, Jiang Y, J. Chromatogr. A, 952, 79 (2002)
  3. Cheng H, Crit. Rev. Food Sci. Nutr., 50, 938 (2010)
  4. Philippe E, Seuvre AM, Colas B, Langendorff V, Schippa C, Voilley A, J. Agric. Food Chem., 51, 1393 (2003)
  5. Pettersson J, Karlsson PC, Goransson U, Rafter JJ, Bohlin L, Biol. Pharm. Bull., 31, 534 (2008)
  6. Clark JH, Tavener SJ, Org. Process Res. Dev., 11, 149 (2007)
  7. Lan EI, Dekishima Y, Chuang DS, Liao JC, AIChE J., 59(9), 3167 (2013)
  8. Heufer KA, Sarathy SM, Curran HJ, Davis AC, Westbrook CK, Pitz WJ, Energy Fuels, 26(11), 6678 (2012)
  9. Togbe C, Halter F, Foucher F, Mounaim-Rousselle C, Dagaut P, Proc. Combust. Inst., 33, 367 (2011)
  10. Dayma G, Togbe C, Dagaut P, Energy Fuels, 25(11), 4986 (2011)
  11. Bitenc M, Horvat B, Likozar B, Drazic G, Orel ZC, Appl. Catal. B: Environ., 136-137, 202 (2013)
  12. Suhadolnik L, Pohar A, Likozar B, Ceh M, Chem. Eng. J., 303, 292 (2016)
  13. Krivec M, Pohar A, Likozar B, Drazic G, AIChE J., 61(2), 572 (2015)
  14. Saha R, Saha B, J. Coord. Chem., 64, 1782 (2011)
  15. Lewicki S, Zdanowski R, Krzyzowska M, Lewicka A, Debski B, Niemcewicz M, Goniewicz M, Ann. Agric. Environ. Med., 21, 331 (2014)
  16. Saha B, Orvig C, Coord. Chem. Rev., 254, 2959 (2010)
  17. Patel S, Mishra BK, Tetrahedron, 63, 4367 (2007)
  18. Bijudas K, Nair TDR, Curr. Chem. Lett., 3, 109 (2014)
  19. Khan Z, Kabir-ud-Din, Akram M, J. Chem. Res.(S), 460 (1998)
  20. Samal PC, Pattnaik BB, Rao SCD, Mahapatro SN, Tetrahedron, 39, 143 (1983)
  21. Bertonia FA, Bellua SE, Gonzaleza JC, Sala LF, Carbohydr. Polym., 114, 1 (2014)
  22. Fawzy A, Ashour SS, Musleh MA, Hassan RM, Asghar BH, J. Saudi Chem. Soc., 20, 450 (2016)
  23. Banas B, Inorg. Chim. Acta, 53, L13 (1981)
  24. Malik VS, Asghar BH, Mansoor SS, J. Taibah Univ. Sci., 10, 131 (2016)
  25. Sengupta KK, Sengupta S, Basu SN, Carbohydr. Res., 71, 75 (1979)
  26. Carreto ML, Rubio S, Perez-Bendito D, Analyst, 121, 33R (1996)
  27. Tascioglu S, Tetrahedron, 52, 11113 (1996)
  28. Dwars T, Paetzold E, Oehme G, Angew. Chem.-Int. Edit., 44, 7174 (2005)
  29. Sorella GL, Strukul G, Scarso A, Green Chem., 17, 644 (2015)
  30. Otto S, Engberts JBFN, Kwak JCT, J. Am. Chem. Soc., 120(37), 9517 (1998)
  31. Vashishtha M, Mishra M, Shaha DO, Appl. Catal. A: Gen., 466, 38 (2013)
  32. Balakumar S, Thanasekaran P, Rajkumar E, Adaikalasamy KJ, Rajagopal S, Ramaraj R, Rajendran T, Manimaran B, Lu KL, Org. Biomol. Chem., 4, 352 (2006)
  33. Al-Blewi FF, Al-Lohedan HA, Rafiquee MZA, Issa ZA, J. Saudi Chem. Soc., 18, 632 (2014)
  34. Pawar B, Padalkar V, Phatangare K, Nirmalkar S, Chaskar A, Catal. Sci. Technol., 1, 1641 (2011)
  35. Nishikata T, Lipshutz BH, Chem. Commun., 6472 (2009)
  36. Shrivastava A, Singh AK, Sachdev N, Shrivastava DR, Katre Y, Singh SP, Singh M, Mejuto JC, J. Mol. Catal. A-Chem., 361-362, 1 (2012)
  37. Rocek J, Peng TY, J. Am. Chem. Soc., 99, 7622 (1977)
  38. Rajalakshmi K, Ramachandramoorthy T, Srinivasan S, J. Chem. Pharm. Res., 4, 894 (2012)
  39. Kaes C, Katz A, Hosseini MW, Chem. Rev., 100(10), 3553 (2000)
  40. Islam M, Saha B, Das AK, J. Mol. Catal. A-Chem., 266(1-2), 21 (2007)
  41. Ghosh SK, Basu A, Saha R, Ghosh A, Mukherjee K, Saha B, J. Coord. Chem., 65, 1158 (2012)
  42. Meenakshisundaram S, Sarathi N, Transition Met. Chem., 31, 569 (2006)
  43. Ghosh A, Saha R, Ghosh SK, Mukherjee K, Saha B, Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 109, 55 (2013)
  44. Ghosh A, Saha R, Saha B, J. Ind. Eng. Chem., 20(1), 345 (2014)
  45. Mukherjee K, Saha R, Ghosh A, Ghosh SK, Saha B, J. Mol. Liq., 179, 1 (2013)
  46. Sar P, Ghosh A, Malik S, Saha B, J. Carbonydr. Chem., 35, 86 (2016)
  47. Saha R, Ghosh A, Sar P, Saha I, Ghosh SK, Mukherjee K, Saha B, Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 116, 524 (2013)
  48. Malik S, Ghosh A, Saha B, J. Solution Chem., 45, 109 (2016)
  49. Anton SD, Morrison CD, Cefalu WT, Martin CK, Diabetes Technol. Ther., 10, 405 (2008)
  50. Morgan ME, Uchiyama H, Christian SD, Tucker EE, Scamehorn JF, Langmuir, 10(7), 2170 (1994)
  51. Gunaseelan K, Ismail K, J. Colloid Interface Sci., 258(1), 110 (2003)
  52. Ruiz CC, Molina-Bolivar JA, Aguiar J, MacIsaac G, Moroze S, Palepu R, Langmuir, 17(22), 6831 (2001)
  53. Pan A, Naskar B, Prameela GKS, Kumar BVNP, Mandal AB, Bhattacharya SC, Moulik SP, Langmuir, 28(39), 13830 (2012)
  54. Kumar L, Mahajan T, Agarwal DD, Ind. Eng. Chem. Res., 51(5), 2227 (2012)
  55. Perez-Benito JF, Arias C, Rodriguez RM, Ros M, New J. Chem., 22, 1445 (1998)
  56. Cotton FA, Wilkinson G, Murillo CA, Bochmann M, Advanced Inorganic Chemistry, 6th ed., John Wiley & Sons, New York, 1999 p. 747.
  57. Rao IV, Ruckenstein R, J. Colloid Interface Sci., 113, 375 (1986)
  58. Banipal TS, Kaur H, Banipal PK, J. Mol. Liq., 218, 112 (2016)
  59. Zdziennicka A, Szymczyk K, Krawczyk J, Janczuk B, Fluid Phase Equilib., 322-323, 126 (2012)
  60. Rafati AA, Gharibi H, Rezaie-Sameti M, J. Mol. Liq., 111, 109 (2004)
  61. Gholivand MB, Ghasemi JB, Saaidpour S, Mohajeri A, Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 71, 1158 (2008)
  62. Bhardwaj V, Sharma P, Chauhan S, Thermochim. Acta, 566, 155 (2013)
  63. Rubio DA, Zanette D, Nome F, Bunton CA, Langmuir, 10(4), 1151 (1994)
  64. Jakubowska A, J. Colloid Interface Sci., 346(2), 398 (2010)
  65. Lin C, Yang L, Xu M, An Q, Xiang Z, Liu X, RSC Adv., 6, 51552 (2016)
  66. Das S, Mondal S, Ghosh S, J. Chem. Eng. Data, 58, 2586 (2013)
  67. Koya PA, Wagay TA, Ismail K, J. Solution Chem., 44, 100 (2015)
  68. Thakkar K, Bharatiya B, Shah DO, Ray D, Aswal VK, Bahadur P, Colloids Surf. A: Physicochem. Eng. Asp., 484, 547 (2015)
  69. Denkova PS, Van Lokeren L, Verbruggen I, Willem R, J. Phys. Chem. B, 112(35), 10935 (2008)
  70. Jha RK, Shylesh S, Bhoware SS, Singh AP, Microporous Mesoporous Mater., 95, 154 (2006)
  71. Sen PK, Chatterjee P, Pal B, J. Mol. Catal. A-Chem., 396, 23 (2015)
  72. Bhardwaj V, Sharma P, Chauhan MS, Chauhan S, J. Mol. Liq., 180, 192 (2013)
  73. Sudholter EJR, van de Langkruis GB, Engberts JBFN, Recl. Trav. Chim. Pays-Bas, 99, 73 (1980)
  74. Manzo G, Carboni M, Rinaldi AC, Casu M, Scorciapino MA, Magn. Reson. Chem., 51, 176 (2013)
  75. Patel V, Ray D, Aswal VK, Bahadur P, Colloids Surf. A: Physicochem. Eng. Asp., 450, 106 (2014)
  76. Dharaiya N, Bahadur P, Singh K, Marangoni DG, Bahadur P, Colloids Surf. A: Physicochem. Eng. Asp., 436, 252 (2013)
  77. Choudhury SD, Barooah N, Aswal VK, Pal H, Bhasikuttana AC, Mohanty J, Soft Matter, 10, 3485 (2014)
  78. Paradies HH, J. Phys. Chem., 84, 599 (1980)
  79. Kamboj R, Singh S, Chauhan V, Colloids Surf. A: Physicochem. Eng. Asp., 441, 233 (2014)