Synthesis of 2, 5 Dimethyl Furan from Renewable Lignocellulosic Biomass

Neha Sharma; Lekha Charan Meher; Krishna Chandra; Mitesh Mittal; Sanjai Kumar Dwivedi; Madhu Bala

doi:10.14429/dlsj.4.12641

Neha Sharma DRDO-Defence Institute of Bio-Energy Research, Haldwani – 500 011, India
Lekha Charan Meher DRDO-Defence Institute of Bio-Energy Research, Haldwani – 500 011, India
Krishna Chandra DRDO-Defence Institute of Bio-Energy Research, Haldwani – 500 011, India
Mitesh Mittal DRDO-Defence Institute of Bio-Energy Research, Haldwani – 500 011, India
Sanjai Kumar Dwivedi DRDO-Defence Research Laboratory, Tejpur - 784 001, India
Madhu Bala DRDO-Defence Institute of Bio-Energy Research, Haldwani – 500 011, India

DOI: https://doi.org/10.14429/dlsj.4.12641

Keywords: Bio-fuel, Lignocellulose, Hydroxymethyl furfural, Cellulose., 2,5-Dimethylfuran, Catalysts

Abstract

Renewable biomass resources could reduce the dependency on the fossil fuels by conversion of its lignocellulose into bio-fuels and other valuable chemicals. Depolymerisation of lignocellulose, hydrolysis of cellulose to monomer glucose and its subsequent dehydration results 5-hydroxymethyl furfural (HMF). HMF is an important platform chemical for fuels and various other applications. The hydrogenation of HMF results 2, 5-dimethylfuran (DMF), which may be a biofuel with 40 per cent greater energy density than that of ethanol. The homogeneous catalytic method is preferred for lignocellulosic biomass conversion to cellulose, its hydrolysis and further dehydration to HMF. The Cu-Ru/C and related catalysts are preferred for hydrogenation of HMD to 2, 5-dimethylfuran. This review is an attempt to summarise the current research and developments in the field of lignocellulose derived HMF and further conversion to DMF as a potential biofuel.

Author Biographies

Neha Sharma, DRDO-Defence Institute of Bio-Energy Research, Haldwani – 500 011, India

Mrs Neha Sharma did MSc (Pharmaceutical Chemistry) from Banasthali University, in 2011. Currently working as Senior Research Fellow in DRDO-Defence Institute of Bio-Energy Research, Haldwani. Her current research interest is synthesis of bio-lubricant form Camelina sativa oil

Lekha Charan Meher, DRDO-Defence Institute of Bio-Energy Research, Haldwani – 500 011, India

Dr Lekha Charan Meher, received his MSc (Chemistry) from Sambalpur University, in 2002 and PhD from IIT Delhi, in 2007. Currently working as Scientist ‘D’ in DRDO-Defence Institute of Bio-Energy Research, Project Site, Secunderabad. He has worked on the first generation biofuels and development of heterogeneous catalyst for vegetable oil transesterification. He has leaded the group for quantification of extractives and the depolymerisation of extractive free biomass from Camelina and Jatropha to cellulose, hemicellulose and lignin by alkali method and state of the art review of lignocellulose to HMF and further hydrogenation to DMF.

Krishna Chandra, DRDO-Defence Institute of Bio-Energy Research, Haldwani – 500 011, India

Mr Krishna Chandra did MSc (Environmental Science) from Kuvempu University. Currently working as Technical Officer ‘A’ in DRDO-Defence Institute of Bio-Energy Research, Haldwani. His current research interests include brief research on bio-fuels cropping system such as Jatropha and Camelina.

Mitesh Mittal, DRDO-Defence Institute of Bio-Energy Research, Haldwani – 500 011, India

Mr Mitesh Mittal presently serving as Officer-in-Charge, DRDO-Defence Institute of Bio-Energy Research, Project Site Secunderabad. He is Lieutenant Colonel in the Indian Army. He has filed 01 x Patent in Indian Patent Office, published 14 research publications in journals. He has been awarded with ‘Member of National Academy of Veterinary Sciences (India)’.

Sanjai Kumar Dwivedi, DRDO-Defence Research Laboratory, Tejpur - 784 001, India

Dr Sanjai Kumar Dwivedi did his PhD in Horticulture, Presently working as Director, DRDO-Defence Research Laboratory, Tezpur (Assam). He was worked as Scientist F and Associate Director at DRDO-Defence Institute of Bio-Energy Research, Haldwani, where he was engaged in development, demonstration & transfer of agro technologies for development of border areas in the Central Himalayan zone. He successfully implemented the low cost greenhouse technology, soil less (Hydroponic) cultivation of crops, utilisation of local plant resources for defence purposes, locals in remote and border areas of Uttarakhand.

Madhu Bala, DRDO-Defence Institute of Bio-Energy Research, Haldwani – 500 011, India

Dr Madhu Bala, MSc, PhD, FABMS, FISRB, is currently serving as Director, DRDO-Defence Institute of Bio-Energy Research, Haldwani. She has 100 research publications, 54 intellectual property rights (IPR/ patents) to her credit. She has submitted 80 novel sequences to NCBI Gene Bank. She has co-authored three books. The current focus of her research is to develop radiation countermeasures for human use against lethal doses of ionising radiation.

References

References:

Rosatella AA, Simeonov SP, Frade RFM, Afonso CAM. 5-Hydroxymethylfurfural (HMF) as a building block platform: Biological properties synthesis and synthetic applications. Green Chem 2011; 13: 754–93.

Weingarten R, Conner Jr WC, Huber GW. Production of levulinic acid from cellulose byhydrothermal decomposition combined withaqueous phase dehydration with a solid acid. Catalyst Energy Environ Sci 2012; 5: 7559–74.

Leshknov YR, Barrett CJ, Liu ZY, Dumesic JA. Production of dimethylfuran for liquid fuels and biomass-derived carbohydrates. Nature letter 2007; 447: 982-85.

Kuster BFM. 5-Hydroxymethylfurfural (HMF) a review focusing on its manufacture. Starch. 1990; 42: 314–21.

Cukalovic A, Stevens CV. Production of biobased HMF derivatives by reductive amination.

Green Chem 2010; 12: 1201–06.

Moreau C, Durand R, Razigade S, Duhamet J, Faugeras P, Rivalier P, Ros P, Avignon G. Dehydration of fructose 5-hydroxymethyl furfural over H-mordenites. Appl Catal 1996; 145: 211-24.

Yan HP, Yang Y, Tong DM, Xiang X, Hu CW. New and future development in catalysis: catalytic biomass conversion. Catal Commun 2009; 10: 1558–63.

Zhang YT, Du HB, Qian XH, Chen EYX. Ionic liquid- water mixtures: enhanced K-w for efficient cellulosic biomass conversion. Energy Fuels 2010; 24: 2410–17.

Musau RM, Munavu RM. The preparation of 5-hydroxylmethyl -2- furaldehyde (HMF) from D-fructose in the presence of DMSO. Biomass 1987; 13: 67–74.

Takagaki A, Ohara M, Nishimura S, Ebitani K. New and future development in catalysis: catalytic biomass conversion. Catal Commun 2009; 41: 6276–78.

Chheda JN, Roman-Leshkov Y, Dumesic JA. Production of 5-hydroxymethylfurfural and furfural by dehydration of biomass-derived mono-saccharides and poly-saccharides. Green Chem 2007; 9: 342–50.

Hu SQ, Zhang ZF, Zhou YX, Song JL, Fan HL, Han BX. Direct conversion of inulin to 5-hydroxymethylfurfural in biorenewableionic liquids. Green Chem 2009; 11: 873–77.

Liu B, Zhang Z, Huang K. Cellulose sulfuric acid as a bio-supported and recyclable solid acid catalyst for the synthesis of 5-hydrxyfurfural and 5-ethoxymethyl furfural from fructose Cellulose. 2013; 20(4): 2081–89.

Kuster BFM, Temmink HMG. The dehydration of D-fructose (formation of 5-hydroxymethyl-2-furaldehyde and levulinic acid): Part IV. The influence of pH and weak-acid anions on the dehydration of D-fructose. Carbohydr Res 1977; 54: 185–91.

de Souza RL, Yu H, Rataboul F, Essayem N. 5-Hydroxymethylfurfural (5-HMF) Production from Hexoses: Limits of Heterogeneous Catalysis in Hydrothermal Conditions and Potential of Concentrated Aqueous Organic Acids as Reactive Solvent System Challenges. 2012; 3: 212–32.

Forsyth SA, Pringle JM, MacFarlane DR. Ionic liquids—an overview. Aust J Chem 2004; 57: 113–19.

Rosatella AA, Branco LC, Afonso CAM. Studies on the dissolution of carbohydrates in ionic liquids and extraction from aqueous phase. Green Chem 2009; 11: 1406–13.

Pinkert A, Marsh KN, Pang SS, Staiger MP. Ionic liquids and their interaction with cellulose. Chem Rev 2009; 109: 6712–28.

Wang H, Gurau G, Rogers RD. Ionic liquid processing of cellulose. Chem Soc Rev 2012; 41: 1519–37.