Catalytic oxidation of 1,3-diisopropylbenzene using imidazolium ionic liquid as catalyst

Shuai Xu; Chongpin Huang; Jie Zhang; Jia Liu; Biaohua Chen

Korean Journal of Chemical Engineering, Vol.26, No.4, 985-989, July, 2009

DOI10.1007/s11814-009-0163-1 Export Citation

Catalytic oxidation of 1,3-diisopropylbenzene using imidazolium ionic liquid as catalyst

Shuai Xu, Chongpin Huang^†, Jie Zhang, Jia Liu, and Biaohua Chen

State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Beijing 100029, China

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Peroxidation of alkylaromatics is the key step in the synthesis of phenols. Different imidazolium ionic liquids were investigated for the oxidation of cumene. The selectivity of cumene hydroperoxide (CHP) increased with different ionic liquids in the order [C4mim]Cl<[C4mim]Br<[C4mim]BF4<[C4mim]OH. This finding could be interpreted as being due to the partial decomposition of CHP by the acidic proton of the imidazolium cation. Thus [C4mim]OH was chosen as the catalyst for the oxidation of 1,3-diisopropylbenzene to corresponding hydroperoxides and its derivatives. The catalytic performance of [C4mim]OH was also better than that of the traditional catalyst NaOH. Furthermore, the effects of the operating variables were investigated and the mechanism was discussed.

Keywords:Catalysis;Ionic Liquid;1,3-Diisopropylbenzene;Hydroperoxide;Oxidation

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[Referenced By]

[1] Schmidt RJ, Appl. Catal. A: Gen., 280(1), 89 (2005)

[2] Wu CY, Pittsburgh P, US Patent, 4,935,551 (1990)

[3] Takaishi HS, Nishinomiya ID, Toyonaka TC, Tanimoto K, Hosaka H, US Patent, 3,953,521 (1976)

[4] Minisci F, Recupero F, Cecchetto A, Gambarotti C, Punta C, Paganelli R, Org. Process Res. Dev., 8, 163 (2004)

[5] Boyaci FG, Takac S, Ozdamar TH, Appl. Catal. A: Gen., 172(1), 59 (1998)

[6] Fukuda O, Sakaguchi S, Ishii Y, Adv. Synth. Catal., 343, 809 (2001)

[7] Aoki Y, Sakaguchi S, Ishii Y, Adv. Synth. Catal., 346, 199 (2004)

[8] Ishii Y, Sakaguchi S, Iwahama T, Adv. Synth. Catal., 343, 393 (2001)

[9] Sheldon RA, Arends IWCE, J. Mol. Catal. A-Chem., 251(1-2), 200 (2006)

[10] Minisci F, Punta C, Recupero F, J. Mol. Catal. A-Chem., 251(1-2), 129 (2006)

[11] Aoki Y, Hirai N, Sakaguchi S, Ishii Y, Tetrahedron., 61, 10995 (2005)

[12] Welton T, Chem. Rev., 99(8), 2071 (1999)

[13] Sheldon R, Chem. Commun., 2399 (2001)

[14] Wasserscheid P, Keim W, Angew. Chem. Int. Ed., 39, 3772 (2000)

[15] Rogers RD, Seddon KR, Science, 302, 792 (2003)

[16] Ju HY, Manju MD, Kim KH, Park SW, Park DW, Korean J. Chem. Eng., 24(5), 917 (2007)

[17] Lee EH, Cha SW, Dharma MM, Choe Y, Ahn JY, Park DW, Korean J. Chem. Eng., 24(3), 547 (2007)

[18] Mun NY, Kim KH, Park DW, Choe Y, Kim I, Korean J. Chem. Eng., 22(4), 556 (2005)

[19] Ju HY, Ahn JY, Manju MD, Kim KH, Park DW, Korean J. Chem. Eng., 25(3), 471 (2008)

[20] Muzart J, Adv. Synth. Catal., 348, 275 (2006)

[21] Zhu HP, Yang F, Tang J, He MY, Green Chem., 5, 38 (2003)

[22] Driver G, Johnson KE, Green Chem., 5, 163 (2003)

[23] Seddon KR, Stark A, Green Chem., 4, 119 (2002)

[24] Mehnert CP, Dispenziere NC, Cook RA, Chem. Commun., 1610 (2002)

[25] Rossi LM, Machado G, Fichtner PFP, Teixeira SR, Dupont J, Catal. Lett., 92(3-4), 149 (2004)

[26] Wan QX, Liu Y, Lu Y, Li M, Wu HH, Catal. Lett., 121, 331 (2008)

[27] Ranu BC, Banerjee S, Org. Lett., 7, 3049 (2005)

[28] Xu JM, Qiao C, Liu BK, Wu Q, Lin XF, Tetrahedron., 63, 986 (2007)

[29] Ranu BC, Banerjee S, Jana R, Tetrahedron., 63, 776 (2007)

[30] Huddleston JG, Visser AE, Reichert WM, Willauer HD, Broker GA, Rogers RD, Green Chem., 3, 156 (2001)

[31] Bonhote P, Dias AP, Papageorgiou N, Kalyanasundaram K, Gratzel M, Inorg. Chem., 35(5), 1168 (1996)

[32] Handy ST, Okello M, J. Org. Chem., 70, 1915 (2005)

[33] Wu CY, US Patent, 4,847,437 (1989)