Solvent and microwave effects on oxidation of aromatic a-diketones

Shidokht Nazari; Khashayar Ghandi

Journal of Industrial and Engineering Chemistry, Vol.21, 198-205, January, 2015

DOI10.1016/j.jiec.2014.02.025 Export Citation

Solvent and microwave effects on oxidation of aromatic a-diketones

Shidokht Nazari, and Khashayar Ghandi^†

Department of Chemistry and Biochemistry, Mount Allison University, 63C York Street, Sackville, NB E4L 1G8, Canada

E-mail:

The effects of microwave irradiation and solvent choice on the oxidation of acenaphthenequinone to 1,8-naphthalic anhydride were investigated. Rate constants of microwave-assisted reactions were larger than those conducted in an oil bath. Both the activation energy and pre-exponential factor of the microwave-assisted reaction changed in comparison to the conventional thermal-heating method. The outcome of the kinetic study on this oxidation reaction might be attributed to a microwave non-thermal effect.

Keywords:Solvent effects;Microwave-enhanced chemistry;Oxidation kinetics

[References]

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Cui L, Hui KN, Hui KS, Lee SK, Zhou W, Wan ZP, Mater. Lett., 75, 175 (2012)
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de Souza ROMA, Antunes OAC, Kroutil W, Kappe CO, J. Org. Chem., 74, 6157 (2009)
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Han DH, Cha SY, Yang HY, Water Res., 38, 2782 (2004)
Hua I, Hoffmann MR, Environ. Sci. Technol., 31, 2237 (1997)
Michelin RA, Sgarbossa P, Scarso A, Strukul G, Coord. Chem. Rev., 254, 646 (2010)
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Mora-Diez N, Keller S, Alvarez-Idaboy JR, Org. Biomol. Chem., 7, 3682 (2009)
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Friess SL, Soloway AH, J. Am. Chem. Soc., 73, 3968 (1951)
Hawthorne MF, Emmons WD, J. Am. Chem. Soc., 80, 6398 (1958)
Ogata Y, Sawaki Y, J. Am. Chem. Soc., 94, 4189 (1972)
Bose TK, Chahine R, Merabet M, Akyel C, Bosisio RG, IEEE Trans. EI-22, 41 (1987)
Ergan BT, Bayramog˘lu M, J. Ind. Eng. Chem., 19(1), 299 (2013)
Spotheim-Maurizot M, Mostafavi M, Douki T, Belloni J, Radiation Chemistry from Basics to Application in Material and Life Sciences, EDP Sciences, 2008.

[Referenced By]

[1] Giguere RJ, Bray TL, Duncan SM, Majetich G, Tetrahedron Lett., 27, 4945 (1986)

[2] Gedye R, Smith F, Westaway K, Ali H, Baldisera L, Laberge L, Tetrahedron Lett., 27, 279 (1986)

[3] Cui L, Hui KN, Hui KS, Lee SK, Zhou W, Wan ZP, Mater. Lett., 75, 175 (2012)

[4] Loupy A, Strauss CR, Microwaves in Organic Synthesis, Wiley-VCH Verlag GmbH & Co. KGaA, 2004p. 35.

[5] Yan J, Wei T, Qiao WM, Shao B, Zhao QK, Zhang LJ, Fan ZJ, Electrochim. Acta, 55(23), 6973 (2010)

[6] Ebner C, Bodner T, Stelzer F, Wiesbrock F, Macromol. Rapid Commun., 32(3), 254 (2011)

[7] Brooks WLA, Sumerlin BS, Isr. J. Chem., 52, 256 (2012)

[8] Theis J, Ritter H, Polym. Int., 61, 1238 (2012)

[9] Alcazar J, Diels G, Schoentjes B, Mini-Rev. Med. Chem., 7, 345 (2007)

[10] Sekhon BS, Int. J. Pharm Tech. Res., 2, 827 (2010)

[11] Dubey A, Srivastava SK, Srivastava SD, Bioorg.Med. Chem. Lett., 21, 569 (2011)

[12] Ghazzali M, El-Faham A, Abdel-Megeed A, Al-Farhan K, J. Mol. Struct., 1013, 163 (2012)

[13] Moseley JD, Kappe CO, Green Chem., 13, 794 (2011)

[14] Zhang X, Hayward DO, Mingos MP, Chem. Commun., 975 (1999)

[15] Horikoshi S, Osawa A, Abe M, Serpone N, J. Phys. Chem. C, 115, 23030 (2011)

[16] Klan P, Literak J, Relich S, J. Photochem. Photobiol. A-Chem., 143, 49 (2001)

[17] de’la Hoz A, Diaz-Ortiz A, Moreno A, Chem. Soc. Rev., 34, 164 (2005)

[18] Perreux L, Loupy A, Tetrahedron, 57, 9199 (2001)

[19] Loupy A, Microwaves in Organic Synthesis, 1st ed., Wiley-VCH, 2002.

[20] Herrero MA, Kremsner JM, Kappe CO, J. Org. Chem., 73, 36 (2007)

[21] Bacsa B, Horvati K, Bosze S, Andreae F, Kappe CO, J. Org. Chem., 73, 7532 (2008)

[22] de Souza ROMA, Antunes OAC, Kroutil W, Kappe CO, J. Org. Chem., 74, 6157 (2009)

[23] Ramier J, Renard E, Grande D, Macromol. Chem. Phys., 213, 784 (2012)

[24] Dallinger D, Irfan M, Suljanovic A, Kappe CO, J. Org. Chem., 75, 5278 (2010)

[25] Liu ZD, Lu YC, Yang BD, Luo GS, J. Appl. Polym. Sci., 127(1), 628 (2013)

[26] Ergan BT, Bayramoglu M, Ind. Eng. Chem. Res., 50(11), 6629 (2011)

[27] Tellez HM, Alquisira JP, Alonso CR, Cortes JGL, Toledano CA, Int. J. Mol. Sci., 12(10), 6703 (2011)

[28] Costa C, Santos VHS, Araujo PHH, Sayer C, Santos AF, Dariva C, Fortuny M, J. Appl. Polym. Sci., 118(3), 1421 (2010)

[29] Ravera M, Musso D, Gosetti F, Cassino C, Gamalero E, Osella D, Chemosphere, 79, 144 (2010)

[30] Zhao D, Cheng J, Hoffmann M, Front. Environ. Sci. Eng. Chin., 5, 57 (2011)

[31] Han DH, Cha SY, Yang HY, Water Res., 38, 2782 (2004)

[32] Hua I, Hoffmann MR, Environ. Sci. Technol., 31, 2237 (1997)

[33] Michelin RA, Sgarbossa P, Scarso A, Strukul G, Coord. Chem. Rev., 254, 646 (2010)

[34] Renz M, Meunier B, Eur. J. Org. Chem., 1999, 737 (1999)

[35] Mora-Diez N, Keller S, Alvarez-Idaboy JR, Org. Biomol. Chem., 7, 3682 (2009)

[36] Bunton CA, Nature, 163, 444 (1949)

[37] Bukharkina TV, Grechishkina OS, Digurov NG, Kon’kov II, Org. Process Res. Dev., 6, 394 (2002)

[38] Xuhong Q, Zhenghua Z, Kongchang C, Dyes Pigment., 11, 13 (1989)

[39] Rusanov A, Polymer Synthesis, Springer, Berlin, Heidelberg, 1994p. 115.

[40] Nazari S, Ghandi K, Fresen. Environ. Bull. (2014)

[41] Lauzon JM, Arseneau DJ, Brodovitch JC, Clyburne J, Cormier P, McCollum B, Ghandi K, Phys. Chem. Chem. Phys., 10, 5957 (2008)

[42] Ghandi K, US 2012/0049101 A1 (2012).

[43] Radhasyam P, Krishna PA, Chakrapani P, Kumari SS, Kumari MS, Bull. Chem. Soc. Jpn., 61, 1363 (2008)

[44] Barnes RP, Lewis RE, J. Am. Chem. Soc., 58, 947 (1936)

[45] Hassall CH, Organic Reactions, John Wiley & Sons, Inc., 2004.

[46] Hayes BL, Aldrichim. Acta, 37 (2004)

[47] Friess SL, Soloway AH, J. Am. Chem. Soc., 73, 3968 (1951)

[48] Hawthorne MF, Emmons WD, J. Am. Chem. Soc., 80, 6398 (1958)

[49] Ogata Y, Sawaki Y, J. Am. Chem. Soc., 94, 4189 (1972)

[50] Bose TK, Chahine R, Merabet M, Akyel C, Bosisio RG, IEEE Trans. EI-22, 41 (1987)

[51] Ergan BT, Bayramog˘lu M, J. Ind. Eng. Chem., 19(1), 299 (2013)

[52] Spotheim-Maurizot M, Mostafavi M, Douki T, Belloni J, Radiation Chemistry from Basics to Application in Material and Life Sciences, EDP Sciences, 2008.