Metal-free mild oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran

Neha Mittal; Grace M. Nisola; Lenny B. Malihan; Jeong Gil Seo; Seong-Poong Lee; Wook-Jin Chung

Korean Journal of Chemical Engineering, Vol.31, No.8, 1362-1367, August, 2014

DOI10.1007/s11814-014-0036-0 Export Citation

Metal-free mild oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran

Neha Mittal, Grace M. Nisola, Lenny B. Malihan, Jeong Gil Seo, Seong-Poong Lee, and Wook-Jin Chung^†

Energy and Environment Fusion Technology Center (E2FTC), Department of Energy and Biotechnology (DEB), Myongji University, Myongji-ro 116, Nam-dong, Cheoin-gu, Yongin City, Gyeonggi-do 449-728, Korea

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The potential of 4-hydroxy-2,2,6,6-tetramethyl-piperidine-1-oxyl (4-hydroxy-TEMPO radical) as an oxidant with [bis(acetoxy)-iodo]benzene (BAIB) and acetic acid (CH3COOH) as co-oxidants to convert 5-hydroxymethylfurfural (5-HMF) into 2,5-diformylfuran (2,5-DFF) was investigated. The effects of oxidant/acid dosages, choice of appropriate solvent, reaction temperature and time were determined to maximize the 2,5-DFF yield. Optimally, 66% 2,5-DFF yield was achieved in TEMPO/BAIB/CH3COOH system at 30 ℃ after 45 min in ethyl acetate. The reaction system is environmentally benign (metal-free) and energy efficient (mild at short reaction period). With scarce reports on 2,5-DFF production, the developed system provides an alternative route for a better access and wider application of this important platform chemical.

Keywords:2,5-Diformylfuran;5-Hydroxymethylfurfural;Homogeneous;Oxidation;Radical;TEMPO

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[2] Ma J, Yu W, Wang M, Jia X, Lu F, Xu J, Chin. J. Catal., 34, 492 (2013)

[3] Ra CH, Jeong GT, Shin MK, Kim SK, Bioresour. Technol., 140, 421 (2013)

[4] Yang WR, Sen A, ChemSusChem, 3, 597 (2010)

[5] Xiang X, He L, Yang Y, Guo B, Tong DM, Hu CW, Catal. Lett., 141(5), 735 (2011)

[6] Gupta NK, Nishimura S, Takagaki A, Ebitani K, Green Chem., 13, 824 (2011)

[7] Chun JA, Lee JW, Yi YB, Hong SS, Chung CH, Korean J. Chem. Eng., 27(3), 930 (2010)

[8] Ren Q, Huang Y, Ma H, Wang F, Gao J, Xu J, Bioresources, 8, 1563 (2013)

[9] Ma J, Pang Y, Wang M, Xu J, Ma H, Nie X, J. Mater. Chem., 22, 3457 (2012)

[10] Hopkins KT, Wilson WD, Bender BC, McCurdy DR, Hall JE, Tidwell RR, Kumar A, Bajic M, Boykin DW, J. Med. Chem., 41, 3872 (1998)

[11] Benahmedgasmi AS, Frere P, Jubault M, Gorgues A, Cousseau J, Garrigues B, Synth. Met., 56, 1751 (1993)

[12] Ma J, Wang M, Du Z, Chen C, Gao J, Xu J, Polym. Chem., 3, 2346 (2012)

[13] Sheibley DW, Manzo MA, Gonzalezsanabria OD, J. Electrochem. Soc., 130, 255 (1983)

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[15] Lewkowski J, Arkivoc, 2, 17 (2001)

[16] Amarasekara AS, Green D, Williams LD, Eur. Polym. J., 45, 595 (2009)

[17] Leshkov YR, Barrett CJ, Liu ZY, Nature, 447, 982 (2007)

[18] Ma JO, Du ZT, Xu J, Chu QH, Pang Y, ChemSusChem, 4, 51 (2011)

[19] Rosatella AA, Simeonov AP, Frade RFM, Afonso CAM, Green Chem., 13, 754 (2011)

[20] Antonyraj CA, Jeong J, Kim B, Shin S, Kim S, Lee KY, Cho JK, J. Ind. Eng. Chem., 19(3), 1056 (2013)

[21] Carlini C, Patrono P, Galletti AMR, Sbrana G, Zima V, Appl. Catal. A: Gen., 289(2), 197 (2005)

[22] Navarro OC, Canos AC, Chornet SI, Top. Catal., 52, 304 (2009)

[23] Stahlberg T, Eyjolfsdottir E, Gorbanev YY, Sadaba I, Riisager A, Catal. Lett., 142(9), 1089 (2012)

[24] Shen Y, Zhang S, Li H, Ren Y, Liu H, Chem.-Eur. J., 16, 7368 (2010)

[25] Pina CD, Falletta E, Prati L, Rossi M, Chem. Soc. Rev., 37, 2077 (2008)

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[35] Tebben L, Studer A, Angew. Chem.-Int. Edit., 50, 5034 (2011)

[36] Hoover JM, Ryland BL, Stahl SS, J. Am. Chem. Soc., 135(6), 2357 (2013)

[37] Toorn JCV, Kemperman G, Sheldon RA, Arends IWCE, J. Org. Chem., 74, 3085 (2009)

[38] Tohma H, Kita Y, Adv. Synth. Catal., 346, 111 (2004)

[39] Uyanik M, Ishihara K, Chem. Commun., 2086 (2009)

[40] Mico A, Margarita R, Parlanti L, Vescovi A, Piancatelli G, J. Org. Chem., 62, 6974 (1997)

[41] Epp JB, Widlanski TS, J. Org. Chem., 64, 295 (1999)

[42] Semmelhack MF, Schmid CR, Cortes DA, Chou S, J. Am. Chem. Soc., 106, 3374 (1984)

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