|
Korean Journal of Chemical Engineering, Vol.31, No.8, 1362-1367, 2014
Metal-free mild oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran
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.
[References]
- Hu L, Sun Y, Lin L, Liu S, J. Taiwan Inst. Chem. Eng., 43, 718, 2012
- Ma J, Yu W, Wang M, Jia X, Lu F, Xu J, Chin. J. Catal., 34, 492, 2013
- Ra CH, Jeong GT, Shin MK, Kim SK, Bioresour. Technol., 140, 421, 2013
- Yang WR, Sen A, ChemSusChem, 3, 597, 2010
- Xiang X, He L, Yang Y, Guo B, Tong DM, Hu CW, Catal. Lett., 141(5), 735, 2011
- Gupta NK, Nishimura S, Takagaki A, Ebitani K, Green Chem., 13, 824, 2011
- Chun JA, Lee JW, Yi YB, Hong SS, Chung CH, Korean J. Chem. Eng., 27(3), 930, 2010
- Ren Q, Huang Y, Ma H, Wang F, Gao J, Xu J, Bioresources, 8, 1563, 2013
- Ma J, Pang Y, Wang M, Xu J, Ma H, Nie X, J. Mater. Chem., 22, 3457, 2012
- Hopkins KT, Wilson WD, Bender BC, McCurdy DR, Hall JE, Tidwell RR, Kumar A, Bajic M, Boykin DW, J. Med. Chem., 41, 3872, 1998
- Benahmedgasmi AS, Frere P, Jubault M, Gorgues A, Cousseau J, Garrigues B, Synth. Met., 56, 1751, 1993
- Ma J, Wang M, Du Z, Chen C, Gao J, Xu J, Polym. Chem., 3, 2346, 2012
- Sheibley DW, Manzo MA, Gonzalezsanabria OD, J. Electrochem. Soc., 130, 255, 1983
- Poeta MD, Schell WA, Dykstra CC, Jones S, Tidwell RR, Czarny A, Bajic M, Bajic M, Kumar A, Boykin D, Perfect JR, Antimicrob. Agents Chemother., 42, 2495, 1998
- Lewkowski J, Arkivoc, 2, 17, 2001
- Amarasekara AS, Green D, Williams LD, Eur. Polym. J., 45, 595, 2009
- Leshkov YR, Barrett CJ, Liu ZY, Nature, 447, 982, 2007
- Ma JO, Du ZT, Xu J, Chu QH, Pang Y, ChemSusChem, 4, 51, 2011
- Rosatella AA, Simeonov AP, Frade RFM, Afonso CAM, Green Chem., 13, 754, 2011
- Antonyraj CA, Jeong J, Kim B, Shin S, Kim S, Lee KY, Cho JK, J. Ind. Eng. Chem., 19(3), 1056, 2013
- Carlini C, Patrono P, Galletti AMR, Sbrana G, Zima V, Appl. Catal. A: Gen., 289(2), 197, 2005
- Navarro OC, Canos AC, Chornet SI, Top. Catal., 52, 304, 2009
- Stahlberg T, Eyjolfsdottir E, Gorbanev YY, Sadaba I, Riisager A, Catal. Lett., 142(9), 1089, 2012
- Shen Y, Zhang S, Li H, Ren Y, Liu H, Chem.-Eur. J., 16, 7368, 2010
- Pina CD, Falletta E, Prati L, Rossi M, Chem. Soc. Rev., 37, 2077, 2008
- Besson M, Gallezot P, Catal. Today, 57(1-2), 127, 2000
- Reijendam JW, Heeres GJ, Janssen MJ, Tetrahedron, 26, 1291, 1970
- Cottier L, Descotes G, Lewkowski J, Skowronski R, Pol. J. Chem., 68, 693, 1994
- Cottier L, Descotes G, Lewkowski J, Skowronski R, Viollet E, J. Heterocycl. Chem., 32, 927, 1995
- Cottier L, Descotes G, Lewkowski J, Skowronski R, Org. Prep. Proced. Int., 27, 564, 1995
- Amarasekara AS, Green D, McMillan E, Catal. Commun., 9, 286, 2008
- Partenheimer W, Grushin VV, Adv. Synth. Catal., 343, 102, 2001
- Nooy AEJ, de Besemar AC, Bekkum HV, Synthesis, 10, 1153, 1996
- Vogler T, Studer A, Synthesis, 13, 1979, 2008
- Tebben L, Studer A, Angew. Chem.-Int. Edit., 50, 5034, 2011
- Hoover JM, Ryland BL, Stahl SS, J. Am. Chem. Soc., 135(6), 2357, 2013
- Toorn JCV, Kemperman G, Sheldon RA, Arends IWCE, J. Org. Chem., 74, 3085, 2009
- Tohma H, Kita Y, Adv. Synth. Catal., 346, 111, 2004
- Uyanik M, Ishihara K, Chem. Commun., 2086, 2009
- Mico A, Margarita R, Parlanti L, Vescovi A, Piancatelli G, J. Org. Chem., 62, 6974, 1997
- Epp JB, Widlanski TS, J. Org. Chem., 64, 295, 1999
- Semmelhack MF, Schmid CR, Cortes DA, Chou S, J. Am. Chem. Soc., 106, 3374, 1984
- Hansen TM, Florence GJ, Mas PL, Chen J, Abrams JN, Forsyth CJ, Tetrahedron Lett., 44, 57, 2003
- Takagaki A, Takahashi M, Nishimura S, Ebitani K, ACS Catal., 1, 1562, 2011
- Herrerias CI, Zhang TY, Li CJ, Tetrahedron Lett., 47, 13, 2006
- Kirumakki SR, Nagaraju N, Narayanan S, Appl. Catal. A: Gen., 273(1-2), 1, 2004
|