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Conversion of plant biomass into organic molecules of interest as fuels, polymers and value-added products

We have developed a process for converting sugars, cellulose, or waste biomass (agricultural, municipal, forestry) into 5-(chloromethyl)furfural (CMF) and levulinic acid(LA) in combined yields >80% of the theoretical.  

   

CMF has been established as an important renewable platform molecule, that can be converted into a broad portfolio of products ranging from biofuels to renewable monomers to agrochemicals and pharmaceuticals, some examples of which are shown below.

   

Levulinic acid can be produced directly from CMF in one high-yielding step, providing synthetic access to an even wider range of derivatives, as shown below. We are currently further exploring the potential of these biomass-derived platform molecules to unlock key renewable chemistry markets.

   

 

Lead references:

"Direct, High-Yield Conversion of Cellulose into Biofuel."  M. Mascal, E. B. Nikitin, Angewandte Chem. Int. Ed. 2008, 47, 7924.

"Towards the Efficient, Total Glycan Utilization of Biomass."  M. Mascal, E. B. Nikitin, ChemSusChem 2009, 2, 423.

"Dramatic Advancements in the Saccharide to 5-Chloromethylfurfural Conversion Reaction."  M. Mascal, E. B. Nikitin, ChemSusChem 2009, 2, 859

"High-Yield Conversion of Plant Biomass Into the Key Value-Added Feedstocks 5-(Hydroxymethyl) furfural, Levulinic acid, and Levulinic Esters via 5-(Chloromethyl)furfural" M. Mascal, E. B. Nikitin, Green Chemistry, Green Chemistry 2010,12, 30.

"Co-processing of Carbohydrates and Lipids in Oil Crops to Produce a Hybrid Biodiesel." M. Mascal and E. B. Nikitin, Energy & Fuels 2010,24, 2170.

"Comment on Processes for the Direct Conversion of Cellulose or Cellulosic Biomass into Levulinate Esters." M. Mascal, E. B. Nikitin, ChemSusChem 2010, 3, 1349.

"Synthesis of the natural herbicide δ-aminolevulinic acid from cellulose-derived 5-(chloromethyl) furfural." M. Mascal, S. Dutta, Green Chemistry 2011,13, 40.

"Synthesis of Ranitidine (Zantac) from Cellulose-Derived 5-(Chloromethyl)furfural," M. Mascal and S. Dutta, Green. Chem. 2011, 13, 3101.

"Concise Photochemical Synthesis of the Antimalarial Indole Alkaloid Decursivine."M. Mascal, K. Modes, A. Durmus, Angewandte Chem. Int. Ed. 2011, 50, 4445.

"Advanced Distillation Curve Analysis on Ethyl Levulinate as a Diesel Fuel Oxygenate and a Hybrid Biodiesel Fuel" B. C. Windom, T. M. Lovestead, M. Mascal, E. B. Nikitin, T. J. Bruno, Energy & Fuels, 2011, 25, 1878.

"Chemicals From Biobutanol: Technologies and Markets." M. Mascal, Biofuels, Bioprod. Bioref. 2012, 6, 483."

 

"The Angelica Lactone Dimer as a Renewable Feedstock for Hydrodeoxygenation: Simple, High-Yield Synthesis of Branched C7 ‒ C10 Gasoline Hydrocarbons" M. Mascal, S. Dutta, I. Gandarias, Angew. Chem. Int. Ed. 2014, 53, 1854.

"Synthesis of the Insecticide Prothrin and Its Analogues from Biomass Derived 5-(Chloromethyl)furfural" F. Chang, S. Dutta, J. J. Becnel, A. S. Estep, M. Mascal, J. Agric. Food Chem. 2014, 62, 476.

"Novel Pathways to 2,5-Dimethylfuran via Biomass-Derived 5-(Chloromethyl)furfural." S. Dutta, M. Mascal, ChemSusChem 2014, 7, 3028.

 

"Chemical-Catalytic Approaches to the Production of Furfurals and Levulinates from Biomass." M. Mascal, S. Dutta, Top. Curr. Chem. 2014, 353, 41.

 

"Top Chemical Opportunities from Carbohydrate Biomass: A Chemist’s View of the Biorefinery." M. Dusselier, M. Mascal, B. F. Sels, Top. Curr. Chem. 2014, 353, 1.

 

"Production of 5-(Chloromethyl)furan-2-carbonyl Chloride and Furan-2,5-dicarbonyl Chloride from Biomass-derived 5-(Chloromethyl)furfural (CMF)." S. Dutta, L. Wu, M. Mascal, Green Chem. 2015, 17, in press.

 

"Efficient, Metal-free Production of Succinic Acid by Oxidation of Biomass-derived Levulinic Acid with Hydrogen Peroxide." S. Dutta, L. Wu, M. Mascal, Green Chem. 2015, 17, 2335.

 

"Efficient, Chemical-Catalytic Approach to the Production of 3-Hydroxypropanoic Acid by Oxidation of Biomass-Derived Levulinic Acid With Hydrogen Peroxide." L. Wu; S. Dutta; M. Mascal ChemSusChem 2015, 8, 1157.

 

"Platform Molecules." T. J. Farmer, M. Mascal, In Introduction to Chemicals from Biomass, 2nd Edition, 2015, J. H. Clark, F. Deswarte, Eds., John Wiley & Sons, Chichester, pp. 89-143.

"5-(Chloromethyl)furfural is the New HMF: Functionally Equivalent But More Practical in Terms of its Production From Biomass." M. Mascal, ChemSusChem 2015, 8, 3391.

"Synthesis of Anti-inflammatory Furan Fatty Acids From Biomass-derived 5-(Chloromethyl) furfural." F. Chang, W.- H. Hsu, M. Mascal, Sustainable Chem. Pharm. 2015, 1, 14.

"Processed Lignin as a Byproduct of the Generation of 5-(Chloromethyl)furfural From Biomass: A Promising New Mesoporous Material." V. L. Budarin, J. H. Clark, J. Henschen, T. J. Farmer, D. J. Macquarrie, M. Mascal, G. K. Nagaraja, T. H. M. Petchey, ChemSusChem 2015, 8, 4172.

"Experimental Studies Towards Optimization of the Production of 5-(Chloromethyl)furfural (CMF) from Glucose in a Two-Phase Reactor." D. R. Lane, M. Mascal, P. Stroeve, Renewable Energy 2016, 85, 994.

"Electrochemical Coupling of Biomass-Derived Acids: New C8 Platforms for Renewable Polymers and Fuels." L. Wu, M. Mascal, T. J. Farmer, S. P. Arnaud, M.-A. Wong Chang, ChemSusChem 2017, 10, 166.

 

 

 

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