Biomass conversion to fuels and chemicals

Beckham, Gregg T.; Johnson, Christopher W.; Vardon, Derek R.; Franden, Mary Ann

Biomass conversion to fuels and chemicals

Patent · Tue Jul 10 04:00:00 EDT 2018

OSTI ID:1462998

Beckham, Gregg T.; Johnson, Christopher W.; Vardon, Derek R.; Franden, Mary Ann

This disclosure relates to compositions and methods for converting biomass to various chemical intermediates and final products including fuels. Aspects include the depolymerization of lignin, cellulose, and hemicellulose to a wide slate of depolymerization compounds that can be subsequently metabolized by genetically modified bacterium, and converted to cis,cis-muconic acid. Other aspects include the use of monometallic catalysts for converting the cis,cis-muconic acid to commodity chemicals and fuels, for example adipic acid and/or nylon.

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Research Organization:: National Renewable Energy Laboratory (NREL), Golden, CO (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: AC36-08GO28308

Assignee:: Alliance for Sustainable Energy, LLC (Golden, CO)

Patent Number(s):: 10,017,792

Application Number:: 14/804,161

OSTI ID:: 1462998

Country of Publication:: United States

Language:: English

References (70)

Can ionic liquids dissolve wood? Processing and analysis of lignocellulosic materials with 1-n-butyl-3-methylimidazolium chloride Fort, Diego A.; Remsing, Richard C.; Swatloski, Richard P. Green Chemistry, Vol. 9, Issue 1, p. 63-69 https://doi.org/10.1039/B607614A	journal	January 2007
Engineering plant cell walls: tuning lignin monomer composition for deconstructable biofuel feedstocks or resilient biomaterials Ciesielski, Peter N.; Resch, Michael G.; Hewetson, Barron Green Chemistry, Vol. 16, Issue 5, p. 2627-2635 https://doi.org/10.1039/c3gc42422g	journal	January 2014
Microbial degradation of aromatic compounds — from one strategy to four Fuchs, Georg; Boll, Matthias; Heider, Johann Nature Reviews Microbiology, Vol. 9, Issue 11, p. 803-816 https://doi.org/10.1038/nrmicro2652	journal	October 2011
Genomic analysis of the aromatic catabolic pathways from Pseudomonas putida KT2440 Jimenez, Jose Ignacio; Minambres, Baltasar; Garcia, Jose Luis Environmental Microbiology, Vol. 4, Issue 12, p. 824-841 https://doi.org/10.1046/j.1462-2920.2002.00370.x	journal	December 2002
Small mobilizable multi-purpose cloning vectors derived from the Escherichia coli plasmids pK18 and pK19: selection of defined deletions in the chromosome of Corynebacterium glutamicum Schäfer, Andreas; Tauch, Andreas; Jäger, Wolfgang Gene, Vol. 145, Issue 1, p. 69-73 https://doi.org/10.1016/0378-1119(94)90324-7	journal	July 1994
Cleavage and hydrodeoxygenation (HDO) of C–O bonds relevant to lignin conversion using Pd/Zn synergistic catalysis Parsell, Trenton H.; Owen, Benjamin C.; Klein, Ian Chem. Sci., Vol. 4, Issue 2, p. 806-813 https://doi.org/10.1039/C2SC21657D	journal	January 2013
Biochemistry of coenzyme B₁₂-dependent glycerol and diol dehydratases and organization of the encoding genes Daniel, Rolf; Bobik, Thomas A.; Gottschalk, Gerhard FEMS Microbiology Reviews, Vol. 22, Issue 5, p. 553-566 https://doi.org/10.1111/j.1574-6976.1998.tb00387.x	journal	December 1998
A Mechanistic Investigation of Acid-Catalyzed Cleavage of Aryl-Ether Linkages: Implications for Lignin Depolymerization in Acidic Environments Sturgeon, Matthew R.; Kim, Seonah; Lawrence, Kelsey ACS Sustainable Chemistry & Engineering, Vol. 2, Issue 3, p. 472-485 https://doi.org/10.1021/sc400384w	journal	November 2013
Deconstruction of Lignocellulosic Biomass to Fuels and Chemicals Chundawat, Shishir P. S.; Beckham, Gregg T.; Himmel, Michael E. Annual Review of Chemical and Biomolecular Engineering, Vol. 2, Issue 1, p. 121-145 https://doi.org/10.1146/annurev-chembioeng-061010-114205	journal	July 2011
Effective hydrodeoxygenation of biomass-derived oxygenates into unsaturated hydrocarbons by MoO₃ using low H₂ pressures Prasomsri, Teerawit; Nimmanwudipong, Tarit; Román-Leshkov, Yuriy Energy & Environmental Science, Vol. 6, Issue 6, p. 1732-1738 https://doi.org/10.1039/c3ee24360e	journal	January 2013
Gas-liquid chromatographic separation of hydroxy monocarboxylic acids and dicarboxylic acids on a fused-silica capillary column Alén, Raimo; Niemelä, Klaus; Sjöström, Eero Journal of Chromatography A, Vol. 301, p. 273-276 https://doi.org/10.1016/S0021-9673(01)89197-4	journal	January 1984
Environmentally compatible synthesis of adipic acid from D-glucose Draths, Karen M.; Frost, John W. Journal of the American Chemical Society, Vol. 116, Issue 1, p. 399-400 https://doi.org/10.1021/ja00080a057	journal	January 1994
Succinic Acid: A New Platform Chemical for Biobased Polymers from Renewable Resources Bechthold, I.; Bretz, K.; Kabasci, S. Chemical Engineering & Technology, Vol. 31, Issue 5, p. 647-654 https://doi.org/10.1002/ceat.200800063	journal	May 2008
The β-Ketoadipate Pathway And The Biology Of Self-Identity Harwood, Caroline S.; Parales, Rebecca E. Annual Review of Microbiology, Vol. 50, Issue 1, p. 553-590 https://doi.org/10.1146/annurev.micro.50.1.553	journal	October 1996
Advances in modifying lignin for enhanced biofuel production Simmons, Blake A.; Loqué, Dominique; Ralph, John Current Opinion in Plant Biology, Vol. 13, Issue 3, p. 312-319 https://doi.org/10.1016/j.pbi.2010.03.001	journal	June 2010
Supported Iron Nanoparticles as Catalysts for Sustainable Production of Lower Olefins Torres Galvis, H. M.; Bitter, J. H.; Khare, C. B. Science, Vol. 335, Issue 6070, p. 835-838 https://doi.org/10.1126/science.1215614	journal	February 2012
Direct Catalytic Conversion of Cellulose into Ethylene Glycol Using Nickel-Promoted Tungsten Carbide Catalysts Ji, Na; Zhang, Tao; Zheng, Mingyuan Angewandte Chemie, Vol. 120, Issue 44, p. 8638-8641 https://doi.org/10.1002/ange.200803233	journal	October 2008
Properties of an inducible uptake system for beta-ketoadipate in Pseudomonas putida. Ornston, L. N.; Parke, D. Journal of Bacteriology, Vol. 125, Issue 2 https://doi.org/10.1128/JB.125.2.475-488.1976	journal	January 1976
δ-Aminolevulinic Acid Dehydratase Genotype and Lead Toxicity: A HuGE Review Kelada, Samir N.; Shelton, Erin; Kaufmann, Rachel B. American Journal of Epidemiology, Vol. 154, Issue 1, p. 1-13 https://doi.org/10.1093/aje/154.1.1	journal	July 2001
Regioselective carboxylation of catechol by 3,4-dihydroxybenzoate decarboxylase of Enterobacter cloacae P Yoshida, Toyokazu; Inami, Yuki; Matsui, Tsuyoshi Biotechnology Letters, Vol. 32, Issue 5, p. 701-705 https://doi.org/10.1007/s10529-010-0210-3	journal	February 2010
Automated design of synthetic ribosome binding sites to control protein expression Salis, Howard M.; Mirsky, Ethan A.; Voigt, Christopher A. Nature Biotechnology, Vol. 27, Issue 10, p. 946-950 https://doi.org/10.1038/nbt.1568	journal	October 2009
Occurrence, metabolism, metabolic role, and industrial uses of bacterial polyhydroxyalkanoates. Anderson, A. J.; Dawes, E. A. Microbiological Reviews, Vol. 54, Issue 4 https://doi.org/10.1128/MMBR.54.4.450-472.1990	journal	January 1990
Effect of chemical surface heterogeneity on the adsorption mechanism of dissolved aromatics on activated carbon Franz, Marcus; Arafat, Hassan A.; Pinto, Neville G. Carbon, Vol. 38, Issue 13, p. 1807-1819 https://doi.org/10.1016/S0008-6223(00)00012-9	journal	January 2000
The Pseudomonas putida Crc global regulator controls the hierarchical assimilation of amino acids in a complete medium: Evidence from proteomic and genomic analyses Moreno, Renata; Martínez-Gomariz, Montserrat; Yuste, Luis PROTEOMICS, Vol. 9, Issue 11, p. 2910-2928 https://doi.org/10.1002/pmic.200800918	journal	June 2009
The tac promoter: a functional hybrid derived from the trp and lac promoters de Boer, H. A.; Comstock, L. J.; Vasser, M. Proceedings of the National Academy of Sciences, Vol. 80, Issue 1, p. 21-25 https://doi.org/10.1073/pnas.80.1.21	journal	January 1983
Lignin Valorization: Improving Lignin Processing in the Biorefinery Ragauskas, A. J.; Beckham, G. T.; Biddy, M. J. Science, Vol. 344, Issue 6185, p. 1246843-1246843 https://doi.org/10.1126/science.1246843	journal	May 2014
Complete nucleotide sequence and polypeptide analysis of multicomponent phenol hydroxylase from Pseudomonas sp. strain CF600. Nordlund, I.; Powlowski, J.; Shingler, V. Journal of Bacteriology, Vol. 172, Issue 12, p. 6826-6833 https://doi.org/10.1128/jb.172.12.6826-6833.1990	journal	December 1990
The Pseudomonas putida Crc Global Regulator Controls the Expression of Genes from Several Chromosomal Catabolic Pathways for Aromatic Compounds Morales, G.; Linares, J. F.; Beloso, A. Journal of Bacteriology, Vol. 186, Issue 5, p. 1337-1344 https://doi.org/10.1128/JB.186.5.1337-1344.2004	journal	February 2004
Advancing the Frontiers in Nanocatalysis, Biointerfaces, and Renewable Energy Conversion by Innovations of Surface Techniques Somorjai, Gabor A.; Frei, Heinz; Park, Jeong Y. Journal of the American Chemical Society, Vol. 131, Issue 46, p. 16589-16605 https://doi.org/10.1021/ja9061954	journal	November 2009
Compositional Analysis of Lignocellulosic Feedstocks. 1. Review and Description of Methods Sluiter, Justin B.; Ruiz, Raymond O.; Scarlata, Christopher J. Journal of Agricultural and Food Chemistry, Vol. 58, Issue 16, p. 9043-9053 https://doi.org/10.1021/jf1008023	journal	August 2010
Emerging catalytic processes for the production of adipic acid Van de Vyver, Stijn; Román-Leshkov, Yuriy Catalysis Science & Technology, Vol. 3, Issue 6, p. 1465-1479 https://doi.org/10.1039/C3CY20728E	journal	January 2013
Process Design and Economics for the Conversion of Lignocellulosic Biomass to Hydrocarbons: Dilute-Acid and Enzymatic Deconstruction of Biomass to Sugars and Biological Conversion of Sugars to Hydrocarbons Davis, R.; Tao, L.; Tan, E. C. D. https://doi.org/10.2172/1107470 NREL/TP-5100-60223	report	October 2013
Complete genome sequence and comparative analysis of the metabolically versatile Pseudomonas putida KT2440 Nelson, K. E.; Weinel, C.; Paulsen, I. T. Environmental Microbiology, Vol. 4, Issue 12, p. 799-808 https://doi.org/10.1046/j.1462-2920.2002.00366.x	journal	December 2002
Adsorption of phenolic compounds by activated carbon—a critical review Dąbrowski, A.; Podkościelny, P.; Hubicki, Z. Chemosphere, Vol. 58, Issue 8, p. 1049-1070 https://doi.org/10.1016/j.chemosphere.2004.09.067	journal	February 2005
Generation of a catR deficient mutant of P. putida KT2440 that produces cis, cis-muconate from benzoate at high rate and yield van Duuren, J. B. J. H.; Wijte, D.; Leprince, A. Journal of Biotechnology, Vol. 156, Issue 3, p. 163-172 https://doi.org/10.1016/j.jbiotec.2011.08.030	journal	December 2011
Sugar hydrogenation over a Ru/C catalyst Sifontes Herrera, Víctor A.; Oladele, Oluwamuyiwa; Kordás, Krisztián Journal of Chemical Technology & Biotechnology, Vol. 86, Issue 5, p. 658-668 https://doi.org/10.1002/jctb.2565	journal	January 2011
Intensified crystallization in complex media: Heuristics for crystallization of platform chemicals Urbanus, J.; Roelands, C. P. M.; Verdoes, D. Chemical Engineering Science, Vol. 77, p. 18-25 https://doi.org/10.1016/j.ces.2012.02.019	journal	July 2012
Chemical properties of catechols and their molecular modes of toxic action in cells, from microorganisms to mammals. Minireview Schweigert, Nina; Zehnder, Alexander J. B.; Eggen, Rik I. L. Environmental Microbiology, Vol. 3, Issue 2, p. 81-91 https://doi.org/10.1046/j.1462-2920.2001.00176.x	journal	February 2001
Microbial synthesis of cis,cis-muconic acid by Sphingobacterium sp. GCG generated from effluent of a styrene monomer (SM) production plant Wu, Chun-Ming; Lee, Tsung-Huei; Lee, Sung-Nung Enzyme and Microbial Technology, Vol. 35, Issue 6-7, p. 598-604 https://doi.org/10.1016/j.enzmictec.2004.08.012	journal	December 2004
Toward biotechnological production of adipic acid and precursors from biorenewables Polen, Tino; Spelberg, Markus; Bott, Michael Journal of Biotechnology, Vol. 167, Issue 2, p. 75-84 https://doi.org/10.1016/j.jbiotec.2012.07.008	journal	August 2013
A Tetrahydrofolate-Dependent O-Demethylase, LigM, Is Crucial for Catabolism of Vanillate and Syringate in Sphingomonas paucimobilis SYK-6 Abe, T.; Masai, E.; Miyauchi, K. Journal of Bacteriology, Vol. 187, Issue 6, p. 2030-2037 https://doi.org/10.1128/JB.187.6.2030-2037.2005	journal	March 2005
PHAs Produced by Pseudomonas putida and Pseudomonas oleovorans Grown with n-Alkanoic Acids Containing Aromatic Groups Kim, Do Young; Rhee, Young Ha Macromolecules, Vol. 32, Issue 19, p. 6058-6064 https://doi.org/10.1021/ma982033t	journal	September 1999
Bimetallic catalysts for upgrading of biomass to fuels and chemicals Alonso, David Martin; Wettstein, Stephanie G.; Dumesic, James A. Chemical Society Reviews, Vol. 41, Issue 24, p. 8075-8098 https://doi.org/10.1039/c2cs35188a	journal	January 2012
Lignin Pyrolysis Components and Upgrading—Technology Review Mu, Wei; Ben, Haoxi; Ragauskas, Art BioEnergy Research, Vol. 6, Issue 4, p. 1183-1204 https://doi.org/10.1007/s12155-013-9314-7	journal	February 2013
Biomass Recalcitrance: Engineering Plants and Enzymes for Biofuels Production Himmel, M. E.; Ding, S.-Y.; Johnson, D. K. Science, Vol. 315, Issue 5813, p. 804-807 https://doi.org/10.1126/science.1137016	journal	February 2007
Purification and Characterization of Pyrocatechase from the Catechol-assimilating Yeast Candida maltosa Gomi, Komakazu; Horiguchi, Sadayuki Agricultural and Biological Chemistry, Vol. 52, Issue 2 https://doi.org/10.1080/00021369.1988.10868673	journal	February 1988
Alkaline Pretreatment of Corn Stover: Bench-Scale Fractionation and Stream Characterization Karp, Eric M.; Donohoe, Bryon S.; O’Brien, Marykate H. ACS Sustainable Chemistry & Engineering, Vol. 2, Issue 6, p. 1481-1491 https://doi.org/10.1021/sc500126u	journal	May 2014
The complete genome sequence of Pseudomonas putida KT2440 is finally available Nelson, Karen E. Environmental Microbiology, Vol. 4, Issue 12 https://doi.org/10.1046/j.1462-2920.2002.00367.x	journal	December 2002
Lignin modification improves fermentable sugar yields for biofuel production Chen, Fang; Dixon, Richard A. Nature Biotechnology, Vol. 25, Issue 7, p. 759-761 https://doi.org/10.1038/nbt1316	journal	June 2007
Solvent fractionation of renewable woody feedstocks: Organosolv generation of biorefinery process streams for the production of biobased chemicals Bozell, Joseph J.; Black, Stuart K.; Myers, Michele Biomass and Bioenergy, Vol. 35, Issue 10, p. 4197-4208 https://doi.org/10.1016/j.biombioe.2011.07.006	journal	October 2011
Development of a broad-host-range sacB-based vector for unmarked allelic exchange Marx, Christopher J. BMC Research Notes, Vol. 1, Article No. 1 https://doi.org/10.1186/1756-0500-1-1	journal	January 2008
The translational repressor Crc controls the Pseudomonas putida benzoate and alkane catabolic pathways using a multi‐tier regulation strategy Hernández-Arranz, Sofía; Moreno, Renata; Rojo, Fernando Environmental Microbiology, Vol. 15, Issue 1, p. 227-241 https://doi.org/10.1111/j.1462-2920.2012.02863.x	journal	August 2012
Disruption of Mediator rescues the stunted growth of a lignin-deficient Arabidopsis mutant Bonawitz, Nicholas D.; Kim, Jeong Im; Tobimatsu, Yuki Nature, Vol. 509, Issue 7500, p. 376-380 https://doi.org/10.1038/nature13084	journal	March 2014
Biosynthesis of cis, cis-Muconic Acid and Its Aromatic Precursors, Catechol and Protocatechuic Acid, from Renewable Feedstocks by Saccharomyces cerevisiae Weber, Christian; Brückner, Christine; Weinreb, Sheila Applied and Environmental Microbiology, Vol. 78, Issue 23, p. 8421-8430 https://doi.org/10.1128/AEM.01983-12	journal	September 2012
Palladium catalysts on activated carbon supports Gurrath, M.; Kuretzky, T.; Boehm, H. P. Carbon, Vol. 38, Issue 8, p. 1241-1255 https://doi.org/10.1016/S0008-6223(00)00026-9	journal	January 2000
Experimental criterion for the absence of artifacts in the measurement of rates of heterogeneous catalytic reactions Madon, Rostam J.; Boudart, Michel Industrial & Engineering Chemistry Fundamentals, Vol. 21, Issue 4, p. 438-447 https://doi.org/10.1021/i100008a022	journal	November 1982
Hydrophobic Nanocellulose Aerogels as Floating, Sustainable, Reusable, and Recyclable Oil Absorbents Korhonen, Juuso T.; Kettunen, Marjo; Ras, Robin H. A. ACS Applied Materials & Interfaces, Vol. 3, Issue 6, p. 1813-1816 https://doi.org/10.1021/am200475b	journal	May 2011
Hydrothermal catalytic processing of saturated and unsaturated fatty acids to hydrocarbons with glycerol for in situ hydrogen production Vardon, Derek R.; Sharma, Brajendra K.; Jaramillo, Humberto Green Chemistry, Vol. 16, Issue 3, p. 1507-1520 https://doi.org/10.1039/c3gc41798k	journal	January 2014
Lignin valorization through integrated biological funneling and chemical catalysis Linger, J. G.; Vardon, D. R.; Guarnieri, M. T. Proceedings of the National Academy of Sciences, Vol. 111, Issue 33, p. 12013-12018 https://doi.org/10.1073/pnas.1410657111	journal	August 2014
Disassembly and reassembly of polyhydroxyalkanoates: Recycling through abiotic depolymerization and biotic repolymerization Myung, Jaewook; Strong, Nathaniel I.; Galega, Wakuna M. Bioresource Technology, Vol. 170, p. 167-174 https://doi.org/10.1016/j.biortech.2014.07.105	journal	October 2014
DO-stat fed-batch production of cis, cis-muconic acid from benzoic acid by Pseudomonas putida BM014 Bang, Sang-Gu; Choi, Cha Yong Journal of Fermentation and Bioengineering, Vol. 79, Issue 4, p. 381-383 https://doi.org/10.1016/0922-338X(95)94001-8	journal	January 1995
Acquisition of a deliberately introduced phenol degradation operon, pheBA, by different indigenous Pseudomonas species. Peters, M.; Heinaru, E.; Talpsep, E. Applied and environmental microbiology, Vol. 63, Issue 12 https://doi.org/10.1128/AEM.63.12.4899-4906.1997	journal	January 1997
Microbial synthesis of cis,cis-muconic acid from benzoate by Sphingobacterium sp. mutants Wu, Chun-Ming; Wu, Chang-Chan; Su, Chien-Chou Biochemical Engineering Journal, Vol. 29, Issue 1-2, p. 35-40 https://doi.org/10.1016/j.bej.2005.02.034	journal	April 2006
Purification and characterization of pyrocatechase from the catecholassimilating yeast Candida maltosa. Gomi, Komakazu; Horiguchi, Sadayuki Agricultural and Biological Chemistry, Vol. 52, Issue 2, p. 585-587 https://doi.org/10.1271/bbb1961.52.585	journal	January 1988
Review of Pt-Based Bimetallic Catalysis: From Model Surfaces to Supported Catalysts Yu, Weiting; Porosoff, Marc D.; Chen, Jingguang G. Chemical Reviews, Vol. 112, Issue 11, p. 5780-5817 https://doi.org/10.1021/cr300096b	journal	August 2012
Benzene-Free Synthesis of Adipic Acid Niu, W.; Draths, K. M.; Frost, J. W. Biotechnology Progress, Vol. 18, Issue 2, p. 201-211 https://doi.org/10.1021/bp010179x	journal	April 2002
Radical catalysis of B12 enzymes: structure, mechanism, inactivation, and reactivation of diol and glycerol dehydratases Toraya, T. Cellular and Molecular Life Sciences (CMLS), Vol. 57, Issue 1, p. 106-127 https://doi.org/10.1007/s000180050502	journal	January 2000
Chemical transformations of succinic acid recovered from fermentation broths by a novel direct vacuum distillation-crystallisation method Luque, Rafael; Lin, Carol S. K.; Du, Chenyu Green Chemistry, Vol. 11, Issue 2, p. 193-200 https://doi.org/10.1039/B813409J	journal	January 2009
The Catalytic Valorization of Lignin for the Production of Renewable Chemicals Zakzeski, Joseph; Bruijnincx, Pieter C. A.; Jongerius, Anna L. Chemical Reviews, Vol. 110, Issue 6, p. 3552-3599 https://doi.org/10.1021/cr900354u	journal	June 2010
One step recovery of succinic acid from fermentation broths by crystallization Li, Qiang; Wang, Dan; Wu, Yong Separation and Purification Technology, Vol. 72, Issue 3, p. 294-300 https://doi.org/10.1016/j.seppur.2010.02.021	journal	May 2010

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