Novel Compounds and Methods for Upgrading Biomass to Produce Premium Biofuels
At A Glance
Researchers at Colorado State University have patented new methods for the direct umpolung self-condensation of 5-hydroxymethylfurfural (HMF) by organocatalysis, thereby upgrading the readily available substrate into 5,5′-di(hydroxymethyl) furoin (DHMF). While many efficient catalyst systems have been developed for conversion of plant biomass resources into HMF, this patent provides methods to convert such nonfood biomass directly into DHMF by a simple process. Additionally, the patent provides highly effective new methods for upgrading other biomass furaldehydes and related compounds to liquid fuels. These methods include the organocatalytic self-condensation (umpolung) of biomass furaldehydes into (C8-C12) furoin intermediates, followed by hydrogenation, etherification or esterification into oxygenated biodiesel, or hydrodeoxygenation by metal-acid tandem catalysis into premium hydrocarbon fuels.
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While alternative fuels from biological sources are currently in use, these first-generation biofuels are derived from edible crops that divert from the global food supply resulting in higher food costs and global food shortages. It is widely recognized that the future of biofuels is in the conversion of inedible sources of biomass (e.g., sawdust, straws, grasses, forest wastes, and other plant matter – collectively referred to as lignocellulosic biomass or plant biomass). The global supply of such naturally renewable biomass is enormous and inexpensive.
It is well known within the biofuel industry that biorefining of value-added chemicals is an essential component to any successful operation. Analogous to oil refining within the petroleum industry, biorefining allows for the production of chemical feedstocks and an array of value-added products that nicely complement biofuel production.
HMF (5’-hydroxymethylfurfural) has been identified as a key and versatile biorefining building block for sustainable chemicals, materials, and liquid fuels. The HMF pathway is highly desirable as the conversion of cellulose to HMF can be achieved through chemical, biological, and hydrothermal pathways.
Nevertheless, several challenges and opportunities exist with the HMF chemical pathway. Methods suitable for the industrial scale conversion of cellulose to HMF have not been developed. Furthermore, although the easiest accessible biofuel from HMF (dimethylfuran, DMF) is twice as energy dense as ethanol, it is still only a six carbon (C6) fuel and therefore, not as energy dense as higher carbon forms of fuel, such as jet fuel or (bio)diesel. Upgrading of HMF to a higher carbon fuel without the use of additional carbon sources is a particularly difficult challenge for which no industrially acceptable solutions exist.
Accordingly, new methods are needed for upgrading HMF into useful intermediates and products.
- Rapid, high yield conversion process
- Nontoxic catalyst operates efficiently under industrially-preferred conditions
- Compatible with known biomass-to-HMF processes
- Potential one-pot biofuel synthesis
- Reduces biofuel production costs and steps by eliminating additional carbon-rich chemicals
- Jet fuel and kerosene (C12) generation
- Chemicals for synthetic chemistry
Zang, H.; Chen, E.Y.X. “Organocatalytic Upgrading of Furfural and 5-Hydroxymethyl Furfural to C10 and C12 Furoins with Quantitative Yield and Atom-Efficiency.” Int. J. Mol. Sci. 2015, 16, 7143-7158.
Liu, D.; Chen, E. Y.-X.* “Organocatalysis in Biorefining for Biomass Conversion and Upgrading”, Green Chem. 2014, 16, 964-981
Liu, D.; Zhang, Y.; Chen, E. Y.-X*. “Organocatalytic Upgrading of the Key Biorefining Building Block by a Catalytic Ionic Liquid and N-heterocyclic Carbenes”, Green Chem. 2012, 14, 2738-2746
Last updated: May 2020