Efficient preparation of DHMF and HMFA from biomass-derived HMF via a Cannizzaro reaction in ionic liquids

Eun-Sil Kang; Da Won Chae; Baekjin Kim; Young Gyu Kim

Journal of Industrial and Engineering Chemistry, Vol.18, No.1, 174-177, January, 2012

DOI10.1016/j.jiec.2011.11.020 Export Citation

Efficient preparation of DHMF and HMFA from biomass-derived HMF via a Cannizzaro reaction in ionic liquids

Eun-Sil Kang, Da Won Chae, Baekjin Kim¹, and Young Gyu Kim^†

Department of Chemical and Biological Engineering, Seoul National University, Seoul 151-744, Republic of Korea
¹Green Chemistry & Manufacturing System Division, Green Process R&D Department & Polymer Materials Research, Korea Institute of Industrial Technology(KITECH), ChoeonAn 330-825, Republic of Korea

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2,5-Dihydroxymethylfuran (DHMF) and 5-hydroxymethylfuranoic acid (HMFA) are the versatile intermediate chemicals of high industrial potential. An efficient preparation of both DHMF and HMFA is reported from biomass-derived HMF via a Cannizzaro reaction using ionic liquids as a reusable reaction solvent under the water-free conditions. The operationally simple and environment-friendly process produces both DHMF and HMFA from HMF consistently in good to high yields up to five runs with the recycled ionic liquid.

Keywords:5-Hydroxymethylfurfural (HMF);2,5-Dihydroxymethylfuran (DHMF);5-Hydroxymethylfuranoic acid (HMFA);Ionic liquid;Cannizzaro reaction

[References]

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Matsumoto I, Nakagawa K, Horiuchi K, Jpn. Kokai., 73, 763 (1973)
Timko JM, Cram DJ, J. Am. Chem. Soc., 96, 7159 (1974)
Hirai H, J. Macromol. Sci. Chem., A21, 1165 (1984)
Gandini A, Belgacem MN, Prog. Polym. Sci., 22, 1203 (1997)
Moreau C, Belgacem MN, Gandini A, Top. Catal., 27, 11 (2004)
Faury A, Gaset A, Gorrichon JP, Inf. Chim., 214, 203 (1981)
Schiavo V, Descotes G, Mentech J, Bull. Soc. Chim. Fr., 704 (1991)
Luijkx GCA, Huck NPM, Bekkum HV, Rantwijk FV, Maat L, Heterocycles., 77, 1037 (2009)
Chidambaram M, Bell AT, Green Chem., 12, 1253 (2010)
Furanix Technologies B.V., 5-Substituted 2-(alkoxymethyl)furans, WO2009/30509, March 12 (2009)
Battelle Memorial Institute, Hydroxymethylfurfural reduction methods and methods of producing furandimethanol, US2007/287845, December 13 (2007)
Moye CJ, Rev. Pure Appl. Chem., 14, 161 (1964)
Finan PA, J. Chem. Soc., 3917 (1963)
Cottier L, Descotes G, Soro Y, Synth. Commun., 33, 4285 (2004)
Goswami S, Dey S, Jana S, Tetrahedron., 64, 6358 (2008)
Blanksma JJ, Chem. Zentralbl., 81, 539 (1910)
Hajj TE, Masroua A, Martin J, Descotes G, Bull. Soc. Chim. Fr., 5, 855 (1987)
Cottier L, Descotes G, Lewkowski J, Skowronski R, Polish J. Chem., 68, 693 (1994)
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Blanksma JJ, Rec. Trav. Chim., 29, 403 (1910)
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Wasserscheid P, Welton T, Ionic Liquids in Synthesis, Wiley-VCH (2007)
Olivier-Bourbigou H, Magna L, J. Mol. Catal. A: Chem., 182-183, 419 (2002)
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Aki SNVK, Brennecke JF, Samanta A, Chem. Commun., 413 (2001)
Mascal M, Nikitin EB, Green Chem., 12, 370 (2010)

[Referenced By]

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[1] Bicker M, Kaiser D, Ott L, Vogel H, J. Supercrit. Fluids, 36(2), 118 (2005)

[2] Lichtenthaler FW, Cuny E, Martin D, Ro¨nninger S, in: Lichtenthaler FW (Ed.), Carbohydrates as Organic Raw Materials, VCH, Weinheim/NewYork, 214 (1991)

[3] British Petroleum Co., Process for production of furfural and 5-(hydroxymethyl)-furfural and corresponding hydrogenated derivatives, FR2556344 14, 1985. June.

[4] Gandini A, ACS Symp. Ser., 433, 195 (1990)

[5] Matsumoto I, Nakagawa K, Horiuchi K, Jpn. Kokai., 73, 763 (1973)

[6] Timko JM, Cram DJ, J. Am. Chem. Soc., 96, 7159 (1974)

[7] Hirai H, J. Macromol. Sci. Chem., A21, 1165 (1984)

[8] Gandini A, Belgacem MN, Prog. Polym. Sci., 22, 1203 (1997)

[9] Moreau C, Belgacem MN, Gandini A, Top. Catal., 27, 11 (2004)

[10] Faury A, Gaset A, Gorrichon JP, Inf. Chim., 214, 203 (1981)

[11] Schiavo V, Descotes G, Mentech J, Bull. Soc. Chim. Fr., 704 (1991)

[12] Luijkx GCA, Huck NPM, Bekkum HV, Rantwijk FV, Maat L, Heterocycles., 77, 1037 (2009)

[13] Chidambaram M, Bell AT, Green Chem., 12, 1253 (2010)

[14] Furanix Technologies B.V., 5-Substituted 2-(alkoxymethyl)furans, WO2009/30509, March 12 (2009)

[15] Battelle Memorial Institute, Hydroxymethylfurfural reduction methods and methods of producing furandimethanol, US2007/287845, December 13 (2007)

[16] Moye CJ, Rev. Pure Appl. Chem., 14, 161 (1964)

[17] Finan PA, J. Chem. Soc., 3917 (1963)

[18] Cottier L, Descotes G, Soro Y, Synth. Commun., 33, 4285 (2004)

[19] Goswami S, Dey S, Jana S, Tetrahedron., 64, 6358 (2008)

[20] Blanksma JJ, Chem. Zentralbl., 81, 539 (1910)

[21] Hajj TE, Masroua A, Martin J, Descotes G, Bull. Soc. Chim. Fr., 5, 855 (1987)

[22] Cottier L, Descotes G, Lewkowski J, Skowronski R, Polish J. Chem., 68, 693 (1994)

[23] Solvay S, Saladino R, Farina A, 2010. Process for the oxidation of alcohol and/or aldehyde groups, WO2010/7139, January 21.

[24] Kiermayer J, Chemiker-Zeitung, Chem. Apparatur., 19, 1004 (1895)

[25] Reichstein T, Helv. Chim. Acta., 9, 1066 (1926)

[26] Lew BW, Atlas Chem. Ind., 1968. Method of producing dehydromucic acid, US3326944, June 20, 1967; Chem. Abstr. 68 (1968), P49434n.

[27] Bekkum HV, Carbohydrates as Organic Raw Materials III, VCH, Weinham (1994)

[28] Vinke P, Ph.D. Thesis, Technical University in Delft, Delft (1991)

[29] Blanksma JJ, Rec. Trav. Chim., 29, 403 (1910)

[30] Middendorp JA, Rec. Trav. Chim., 38, 42 (1919)

[31] Wasserscheid P, Welton T, Ionic Liquids in Synthesis, Wiley-VCH (2007)

[32] Olivier-Bourbigou H, Magna L, J. Mol. Catal. A: Chem., 182-183, 419 (2002)

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

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

[35] Fang D, Jiao CM, Zhang HB, Ji BH, J. Ind. Eng. Chem., 16(2), 233 (2010)

[36] Chen W, Yin H, Zhang Y, Lu Z, Wang A, Shen Y, Jiang T, Yu L, J. Ind. Eng. Chem., 16(5), 800 (2010)

[37] Susan MA, Kaneko T, Noda A, Watanabe M, J. Am. Chem. Soc., 127(13), 4976 (2005)

[38] Suarez PAZ, Dullius JEL, Einloft S, Souza RFD, Dupont J, Polyhedron., 15, 1217 (1996)

[39] Min G, Yim T, Lee H, Huh D, Lee E, Mun J, Oh S, Kim YG, Bull. Korean Chem.Soc., 27, 847 (2006)

[40] Sato T, Maruo T, Marukane S, Takagi K, J. Power Sources, 138(1-2), 253 (2004)

[41] Yim T, Lee H, Kim H, Mun J, Kim S, Oh S, Kim YG, Bull. Korean Chem. Soc., 28, 1567 (2007)

[42] Turner JH, Rebers P, Barrick PL, Cotton RH, Anal. Chem., 26, 898 (1954)

[43] Olsson K, Pernemalm PA, Popoff T, Theander O, Acta Chem. Scand., Ser. B: Org.Chem. Biochem., 31, 469 (1977)

[44] The reaction was found to be first order with base and second order with aldehyde, whereas it is second order with both base and aldehyde at higher base concentrations J. Hine, Physical Organic Chemistry, Mcgraw-Hill, New York, 259 (1956)

[45] Lachowicz DR, Gritter RJ, J. Org. Chem., 28, 106 (1953)

[46] Aki SNVK, Brennecke JF, Samanta A, Chem. Commun., 413 (2001)

[47] Mascal M, Nikitin EB, Green Chem., 12, 370 (2010)