Selective oxidation of HMF to DFF using Ru/γ-alumina catalyst in moderate boiling solvents toward industrial production

Churchil A. Antonyraj; Jaewon Jeong; Bora Kim; Seunghan Shin; Sangyong Kim; Kwan-Young Lee; Jin Ku Cho

Journal of Industrial and Engineering Chemistry, Vol.19, No.3, 1056-1059, May, 2013

DOI10.1016/j.jiec.2012.12.002 Export Citation

Selective oxidation of HMF to DFF using Ru/γ-alumina catalyst in moderate boiling solvents toward industrial production

Churchil A. Antonyraj¹, Jaewon Jeong¹, Bora Kim^{1, 2}, Seunghan Shin¹, Sangyong Kim¹, Kwan-Young Lee², and Jin Ku Cho^{1, †}

¹Green Process and Materials R&D Group, Korea Institute of Industrial Technology (KITECH), 35-3 Hongcheon-Ri, Ipchang-Myeon, Seobuk-Gu, Cheonan-Si, Chungnam 330-825, South Korea
²Department of Chemical and Biological Engineering, Korea University, 5-1, Anam-dong, Seongbuk-ku, Seoul 136-713, South Korea

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Selective oxidation of 5-hydroxymethyl-2-furfural (HMF) to 2,5-diformylfuran (DFF) toward industrial production was studied over Ru supported γ-alumina catalyst using molecular oxygen as an oxidant. From the solvents screening, considering recyclability after reaction, toluene was found to be the best solvent and gave maximum conversion of 99% with 97% DFF selectivity at 130 ℃ and 40 psi O2 pressure. Catalyst was washed with NaOH solution of pH = 12 to remove the adsorbed polymer impurities and then reused up to 5 cycles. The product could be purified by simple evaporation of the solvent, which could add advantage for industrial process.

Keywords:Biomass;Ruthenium;γ-Alumina;Selective oxidation;5-Hydroxymethyl-2-furfural (HMF);2,5-Diformylfuran (DFF)

[References]

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Gorbanev YY, Klitgaard SK, Woodley JM, Christensen CH, Riisager A, Chem-SusChem., 2, 672 (2009)
Gupta NK, Nishimura S, Takagaki A, Ebitani K, Green Chemistry., 13, 824 (2011)
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[Referenced By]

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[3] Chheda JN, Huber GW, Dumesic JA, Angewandte Chemie International Edition., 46, 7164 (2007)

[4] Climent MJ, Corma A, Iborra S, Green Chemistry., 13, 520 (2011)

[5] Rosatella AA, Simeonov SP, Frade RFM, Afonso CAM, Green Chemistry., 13, 754 (2011)

[6] Lilga MA, Hallen RT, Gray M, Topics in Catalysis., 53, 1264 (2010)

[7] Alamillo R, Tucker M, Chia M, Paga´ n-Torres Y, Dumesic J, Green Chemistry., 14, 1413 (2012)

[8] Balakrishnan M, Sacia ER, Bell AT, Green Chemistry., 14, 1626 (2012)

[9] Du Z, Ma J, Wang F, Liu J, Xu J, Green Chemistry., 13, 554 (2011)

[10] Maldonado GMG, Assary RS, Dumesic J, Curtiss LA, Energy Environmental Science., 5, 6981 (2012)

[11] Gandini A, Belgacem NM, Polymer International., 47, 267 (1998)

[12] del Poeta M, Schell WA, Dykstra CC, Jones S, Tidwell RR, Czarny A, Bajic M, Kumar A, Boykin D, Perfect JR, Antimicrobial Agents and Chemotherapy., 42, 2495 (1998)

[13] Hopkins KT, Wilson WD, Bendan BC, McCurdy DR, Hall JE, Tidwell RR, Kumar A, Bajic M, Boykin DW, Journal of Medicinal Chemistry., 41, 3872 (1998)

[14] Amarasekara AS, LaToya DG, Williams D, European Polymer Journal., 45, 595 (2009)

[15] Weissermel K, Arpe HJ, Industrial Organic Chemistry, VC-Wiley, Weinheim, 225 (1997)

[16] Halliday GA, Young RJ, Grushin VV, Organic Letters., 5, 2003 (2003)

[17] Grushin VV, Herron N, Halliday GA, US 6,706,900 B2 (2004)

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

[19] Takagaki A, Takahashi M, Nishimura S, Ebitani K, ACS Catalysis., 1, 1562 (2011)

[20] Partenheimer A, Grushin VV, Advanced Synthesis & Catalysis., 343, 102 (2001)

[21] Vinke P, de Wit D, de Goede TJW, Van Bekkum H, New Developments in Selective Oxidation by Heterogeneous Catalysis, Elsevier, New York (1989)

[22] Verdeguer P, Merat N, Gasset A, Journal of Molecular Catalysis., 85, 327 (1993)

[23] Gorbanev YY, Klitgaard SK, Woodley JM, Christensen CH, Riisager A, Chem-SusChem., 2, 672 (2009)

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

[25] Amarasekara AS, Green D, McMillan E, Catalysis Communications., 9, 286 (2008)

[26] Navarro OC, Canos AC, Chornet SI, Topics in Catalysis., 52, 304 (2009)

[27] Rachiero GP, Demirci UB, Miele P, Catal. Today, 170(1), 85 (2011)