Biomass conversion to fuels and chemicals
Abstract
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.
- Inventors:
- Issue Date:
- Research Org.:
- National Renewable Energy Lab. (NREL), Golden, CO (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1462998
- Patent Number(s):
- 10017792
- Application Number:
- 14/804,161
- Assignee:
- Alliance for Sustainable Energy, LLC (Golden, CO)
- Patent Classifications (CPCs):
-
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
C - CHEMISTRY C12 - BIOCHEMISTRY C12Y - ENZYMES
- DOE Contract Number:
- AC36-08GO28308
- Resource Type:
- Patent
- Resource Relation:
- Patent File Date: 2015 Jul 20
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 09 BIOMASS FUELS
Citation Formats
Beckham, Gregg T., Johnson, Christopher W., Vardon, Derek R., and Franden, Mary Ann. Biomass conversion to fuels and chemicals. United States: N. p., 2018.
Web.
Beckham, Gregg T., Johnson, Christopher W., Vardon, Derek R., & Franden, Mary Ann. Biomass conversion to fuels and chemicals. United States.
Beckham, Gregg T., Johnson, Christopher W., Vardon, Derek R., and Franden, Mary Ann. Tue .
"Biomass conversion to fuels and chemicals". United States. https://www.osti.gov/servlets/purl/1462998.
@article{osti_1462998,
title = {Biomass conversion to fuels and chemicals},
author = {Beckham, Gregg T. and Johnson, Christopher W. and Vardon, Derek R. and Franden, Mary Ann},
abstractNote = {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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2018},
month = {7}
}
Works referenced in this record:
Biocatalysts with enhanced inhibitor tolerance
patent, December 2015
- Yang, Shihui; Linger, Jeffrey; Franden, Mary Ann
- US Patent Document 9,206,445
Adsorption of phenolic compounds by activated carbon—a critical review
journal, February 2005
- Dąbrowski, A.; Podkościelny, P.; Hubicki, Z.
- Chemosphere, Vol. 58, Issue 8, p. 1049-1070
Disassembly and reassembly of polyhydroxyalkanoates: Recycling through abiotic depolymerization and biotic repolymerization
journal, October 2014
- Myung, Jaewook; Strong, Nathaniel I.; Galega, Wakuna M.
- Bioresource Technology, Vol. 170, p. 167-174
Microbial synthesis of cis,cis-muconic acid from benzoate by Sphingobacterium sp. mutants
journal, April 2006
- Wu, Chun-Ming; Wu, Chang-Chan; Su, Chien-Chou
- Biochemical Engineering Journal, Vol. 29, Issue 1-2, p. 35-40
The Pseudomonas putida Crc global regulator controls the hierarchical assimilation of amino acids in a complete medium: Evidence from proteomic and genomic analyses
journal, June 2009
- Moreno, Renata; Martínez-Gomariz, Montserrat; Yuste, Luis
- PROTEOMICS, Vol. 9, Issue 11, p. 2910-2928
Acquisition of a deliberately introduced phenol degradation operon, pheBA, by different indigenous Pseudomonas species.
journal, January 1997
- Peters, M.; Heinaru, E.; Talpsep, E.
- Applied and environmental microbiology, Vol. 63, Issue 12
Purification and Characterization of Pyrocatechase from the Catechol-assimilating Yeast Candida maltosa
journal, February 1988
- Gomi, Komakazu; Horiguchi, Sadayuki
- Agricultural and Biological Chemistry, Vol. 52, Issue 2
Radical catalysis of B12 enzymes: structure, mechanism, inactivation, and reactivation of diol and glycerol dehydratases
journal, January 2000
- Toraya, T.
- Cellular and Molecular Life Sciences (CMLS), Vol. 57, Issue 1, p. 106-127
Advancing the Frontiers in Nanocatalysis, Biointerfaces, and Renewable Energy Conversion by Innovations of Surface Techniques
journal, November 2009
- Somorjai, Gabor A.; Frei, Heinz; Park, Jeong Y.
- Journal of the American Chemical Society, Vol. 131, Issue 46, p. 16589-16605
Toward biotechnological production of adipic acid and precursors from biorenewables
journal, August 2013
- Polen, Tino; Spelberg, Markus; Bott, Michael
- Journal of Biotechnology, Vol. 167, Issue 2, p. 75-84
Effect of chemical surface heterogeneity on the adsorption mechanism of dissolved aromatics on activated carbon
journal, January 2000
- Franz, Marcus; Arafat, Hassan A.; Pinto, Neville G.
- Carbon, Vol. 38, Issue 13, p. 1807-1819
Development of a broad-host-range sacB-based vector for unmarked allelic exchange
journal, January 2008
- Marx, Christopher J.
- BMC Research Notes, Vol. 1, Article No. 1
Lignin modification improves fermentable sugar yields for biofuel production
journal, June 2007
- Chen, Fang; Dixon, Richard A.
- Nature Biotechnology, Vol. 25, Issue 7, p. 759-761
δ-Aminolevulinic Acid Dehydratase Genotype and Lead Toxicity: A HuGE Review
journal, July 2001
- Kelada, Samir N.; Shelton, Erin; Kaufmann, Rachel B.
- American Journal of Epidemiology, Vol. 154, Issue 1, p. 1-13
Process for production of sugars and optionally cellulose and lignin from lignocellulosic raw materials
patent, May 1985
- Sinner, Michael; Dietrichs, Hans-Hermann; Puls, Jurgen
- US Patent Document 4,520,105
Pretreatment and Fractionation of Lignocellulosic Biomass
patent-application, September 2014
- Paripati, Praveen; Dadi, Anantharam Prasad
- US Patent Application 13/841707; 20140273104
Hydrothermal catalytic processing of saturated and unsaturated fatty acids to hydrocarbons with glycerol for in situ hydrogen production
journal, January 2014
- Vardon, Derek R.; Sharma, Brajendra K.; Jaramillo, Humberto
- Green Chemistry, Vol. 16, Issue 3, p. 1507-1520
Deconstruction of Lignocellulosic Biomass to Fuels and Chemicals
journal, July 2011
- Chundawat, Shishir P. S.; Beckham, Gregg T.; Himmel, Michael E.
- Annual Review of Chemical and Biomolecular Engineering, Vol. 2, Issue 1, p. 121-145
Sugar hydrogenation over a Ru/C catalyst
journal, January 2011
- Sifontes Herrera, Víctor A.; Oladele, Oluwamuyiwa; Kordás, Krisztián
- Journal of Chemical Technology & Biotechnology, Vol. 86, Issue 5, p. 658-668
Pulping of lignocellulose with aqueous alcohol and alkaline earth metal salt catalyst
patent, June 1986
- Chang, Pei-Ching; Paszner, Laszlo
- US Patent Document 4,594,130
The translational repressor Crc controls the Pseudomonas putida benzoate and alkane catabolic pathways using a multi‐tier regulation strategy
journal, August 2012
- Hernández-Arranz, Sofía; Moreno, Renata; Rojo, Fernando
- Environmental Microbiology, Vol. 15, Issue 1, p. 227-241
Environmentally compatible synthesis of adipic acid from D-glucose
journal, January 1994
- Draths, Karen M.; Frost, John W.
- Journal of the American Chemical Society, Vol. 116, Issue 1, p. 399-400
Lignin valorization through integrated biological funneling and chemical catalysis
journal, August 2014
- Linger, J. G.; Vardon, D. R.; Guarnieri, M. T.
- Proceedings of the National Academy of Sciences, Vol. 111, Issue 33, p. 12013-12018
Effective hydrodeoxygenation of biomass-derived oxygenates into unsaturated hydrocarbons by MoO3 using low H2 pressures
journal, January 2013
- Prasomsri, Teerawit; Nimmanwudipong, Tarit; Román-Leshkov, Yuriy
- Energy & Environmental Science, Vol. 6, Issue 6, p. 1732-1738
Compositional Analysis of Lignocellulosic Feedstocks. 1. Review and Description of Methods
journal, August 2010
- Sluiter, Justin B.; Ruiz, Raymond O.; Scarlata, Christopher J.
- Journal of Agricultural and Food Chemistry, Vol. 58, Issue 16, p. 9043-9053
Intensified crystallization in complex media: Heuristics for crystallization of platform chemicals
journal, July 2012
- Urbanus, J.; Roelands, C. P. M.; Verdoes, D.
- Chemical Engineering Science, Vol. 77, p. 18-25
Microorganisms having multiple compatible degradative energy-generating plasmids and preparation thereof
patent, March 1981
- Chakrabarty, Ananda
- US Patent Document 4,259,444
Disruption of Mediator rescues the stunted growth of a lignin-deficient Arabidopsis mutant
journal, March 2014
- Bonawitz, Nicholas D.; Kim, Jeong Im; Tobimatsu, Yuki
- Nature, Vol. 509, Issue 7500, p. 376-380
Regioselective carboxylation of catechol by 3,4-dihydroxybenzoate decarboxylase of Enterobacter cloacae P
journal, February 2010
- Yoshida, Toyokazu; Inami, Yuki; Matsui, Tsuyoshi
- Biotechnology Letters, Vol. 32, Issue 5, p. 701-705
The complete genome sequence of Pseudomonas putida KT2440 is finally available
journal, December 2002
- Nelson, Karen E.
- Environmental Microbiology, Vol. 4, Issue 12
Synthesis of adipic acid from biomass-derived carbon sources
patent, January 1996
- Frost, John; Draths, Karen
- US Patent Document 5,487,987
Biosynthesis of cis, cis-Muconic Acid and Its Aromatic Precursors, Catechol and Protocatechuic Acid, from Renewable Feedstocks by Saccharomyces cerevisiae
journal, September 2012
- Weber, Christian; Brückner, Christine; Weinreb, Sheila
- Applied and Environmental Microbiology, Vol. 78, Issue 23, p. 8421-8430
Process for the production of muconic acid
patent, March 1988
- Maxwell, Peter
- US Patent Document 4,731,328
One step recovery of succinic acid from fermentation broths by crystallization
journal, May 2010
- Li, Qiang; Wang, Dan; Wu, Yong
- Separation and Purification Technology, Vol. 72, Issue 3, p. 294-300
The Pseudomonas putida Crc Global Regulator Controls the Expression of Genes from Several Chromosomal Catabolic Pathways for Aromatic Compounds
journal, February 2004
- Morales, G.; Linares, J. F.; Beloso, A.
- Journal of Bacteriology, Vol. 186, Issue 5, p. 1337-1344
Alkaline Pretreatment of Corn Stover: Bench-Scale Fractionation and Stream Characterization
journal, May 2014
- Karp, Eric M.; Donohoe, Bryon S.; O’Brien, Marykate H.
- ACS Sustainable Chemistry & Engineering, Vol. 2, Issue 6, p. 1481-1491
Lignin Valorization: Improving Lignin Processing in the Biorefinery
journal, May 2014
- Ragauskas, A. J.; Beckham, G. T.; Biddy, M. J.
- Science, Vol. 344, Issue 6185, p. 1246843-1246843
A Mechanistic Investigation of Acid-Catalyzed Cleavage of Aryl-Ether Linkages: Implications for Lignin Depolymerization in Acidic Environments
journal, November 2013
- Sturgeon, Matthew R.; Kim, Seonah; Lawrence, Kelsey
- ACS Sustainable Chemistry & Engineering, Vol. 2, Issue 3, p. 472-485
Biological synthesis of difunctional alkanes from carbohydrate feedstocks
patent, March 2012
- Baynes, Brian; Geremia, John
- US Patent Document 8,133,704
Emerging catalytic processes for the production of adipic acid
journal, January 2013
- Van de Vyver, Stijn; Román-Leshkov, Yuriy
- Catalysis Science & Technology, Vol. 3, Issue 6, p. 1465-1479
Benzene-Free Synthesis of Adipic Acid
journal, April 2002
- Niu, W.; Draths, K. M.; Frost, J. W.
- Biotechnology Progress, Vol. 18, Issue 2, p. 201-211
Bimetallic catalysts for upgrading of biomass to fuels and chemicals
journal, January 2012
- Alonso, David Martin; Wettstein, Stephanie G.; Dumesic, James A.
- Chemical Society Reviews, Vol. 41, Issue 24, p. 8075-8098
Can ionic liquids dissolve wood? Processing and analysis of lignocellulosic materials with 1-n-butyl-3-methylimidazolium chloride
journal, January 2007
- Fort, Diego A.; Remsing, Richard C.; Swatloski, Richard P.
- Green Chemistry, Vol. 9, Issue 1, p. 63-69
Plasmid, transformants and process for production of 3- carboxymuconolactone
patent, July 2012
- Mase, Kohei; Shimo, Toshihisa; Ohara, Naoki
- US Patent Document 8,211,683
Generation of a catR deficient mutant of P. putida KT2440 that produces cis, cis-muconate from benzoate at high rate and yield
journal, December 2011
- van Duuren, J. B. J. H.; Wijte, D.; Leprince, A.
- Journal of Biotechnology, Vol. 156, Issue 3, p. 163-172
Review of Pt-Based Bimetallic Catalysis: From Model Surfaces to Supported Catalysts
journal, August 2012
- Yu, Weiting; Porosoff, Marc D.; Chen, Jingguang G.
- Chemical Reviews, Vol. 112, Issue 11, p. 5780-5817
Chemical transformations of succinic acid recovered from fermentation broths by a novel direct vacuum distillation-crystallisation method
journal, January 2009
- Luque, Rafael; Lin, Carol S. K.; Du, Chenyu
- Green Chemistry, Vol. 11, Issue 2, p. 193-200
Method of separating lignocellulosic material into lignin, cellulose and dissolved sugars
patent, March 1998
- Black, Stuart; Hames, Bonnie; Myers, Michele
- US Patent Document 5,730,837
Biochemistry of coenzyme B12-dependent glycerol and diol dehydratases and organization of the encoding genes
journal, December 1998
- Daniel, Rolf; Bobik, Thomas A.; Gottschalk, Gerhard
- FEMS Microbiology Reviews, Vol. 22, Issue 5, p. 553-566
DO-stat fed-batch production of cis, cis-muconic acid from benzoic acid by Pseudomonas putida BM014
journal, January 1995
- Bang, Sang-Gu; Choi, Cha Yong
- Journal of Fermentation and Bioengineering, Vol. 79, Issue 4, p. 381-383
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
report, October 2013
- Davis, R.; Tao, L.; Tan, E. C. D.
- NREL/TP-5100-60223
Genomic analysis of the aromatic catabolic pathways from Pseudomonas putida KT2440
journal, December 2002
- Jimenez, Jose Ignacio; Minambres, Baltasar; Garcia, Jose Luis
- Environmental Microbiology, Vol. 4, Issue 12, p. 824-841
Lignin Pyrolysis Components and Upgrading—Technology Review
journal, February 2013
- Mu, Wei; Ben, Haoxi; Ragauskas, Art
- BioEnergy Research, Vol. 6, Issue 4, p. 1183-1204
Microbial synthesis of cis,cis-muconic acid by Sphingobacterium sp. GCG generated from effluent of a styrene monomer (SM) production plant
journal, December 2004
- Wu, Chun-Ming; Lee, Tsung-Huei; Lee, Sung-Nung
- Enzyme and Microbial Technology, Vol. 35, Issue 6-7, p. 598-604
Properties of an inducible uptake system for beta-ketoadipate in Pseudomonas putida.
journal, January 1976
- Ornston, L. N.; Parke, D.
- Journal of Bacteriology, Vol. 125, Issue 2
Hydrophobic Nanocellulose Aerogels as Floating, Sustainable, Reusable, and Recyclable Oil Absorbents
journal, May 2011
- Korhonen, Juuso T.; Kettunen, Marjo; Ras, Robin H. A.
- ACS Applied Materials & Interfaces, Vol. 3, Issue 6, p. 1813-1816
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
journal, July 1994
- Schäfer, Andreas; Tauch, Andreas; Jäger, Wolfgang
- Gene, Vol. 145, Issue 1, p. 69-73
Succinic Acid: A New Platform Chemical for Biobased Polymers from Renewable Resources
journal, May 2008
- Bechthold, I.; Bretz, K.; Kabasci, S.
- Chemical Engineering & Technology, Vol. 31, Issue 5, p. 647-654
Microbial degradation of aromatic compounds — from one strategy to four
journal, October 2011
- Fuchs, Georg; Boll, Matthias; Heider, Johann
- Nature Reviews Microbiology, Vol. 9, Issue 11, p. 803-816
A Tetrahydrofolate-Dependent O-Demethylase, LigM, Is Crucial for Catabolism of Vanillate and Syringate in Sphingomonas paucimobilis SYK-6
journal, March 2005
- Abe, T.; Masai, E.; Miyauchi, K.
- Journal of Bacteriology, Vol. 187, Issue 6, p. 2030-2037
Solvent fractionation of renewable woody feedstocks: Organosolv generation of biorefinery process streams for the production of biobased chemicals
journal, October 2011
- Bozell, Joseph J.; Black, Stuart K.; Myers, Michele
- Biomass and Bioenergy, Vol. 35, Issue 10, p. 4197-4208
Advances in modifying lignin for enhanced biofuel production
journal, June 2010
- Simmons, Blake A.; Loqué, Dominique; Ralph, John
- Current Opinion in Plant Biology, Vol. 13, Issue 3, p. 312-319
Biomass Recalcitrance: Engineering Plants and Enzymes for Biofuels Production
journal, February 2007
- Himmel, M. E.; Ding, S.-Y.; Johnson, D. K.
- Science, Vol. 315, Issue 5813, p. 804-807
Direct Catalytic Conversion of Cellulose into Ethylene Glycol Using Nickel-Promoted Tungsten Carbide Catalysts
journal, October 2008
- Ji, Na; Zhang, Tao; Zheng, Mingyuan
- Angewandte Chemie, Vol. 120, Issue 44, p. 8638-8641
Experimental criterion for the absence of artifacts in the measurement of rates of heterogeneous catalytic reactions
journal, November 1982
- Madon, Rostam J.; Boudart, Michel
- Industrial & Engineering Chemistry Fundamentals, Vol. 21, Issue 4, p. 438-447
Gas-liquid chromatographic separation of hydroxy monocarboxylic acids and dicarboxylic acids on a fused-silica capillary column
journal, January 1984
- Alén, Raimo; Niemelä, Klaus; Sjöström, Eero
- Journal of Chromatography A, Vol. 301, p. 273-276
Chemical properties of catechols and their molecular modes of toxic action in cells, from microorganisms to mammals. Minireview
journal, February 2001
- Schweigert, Nina; Zehnder, Alexander J. B.; Eggen, Rik I. L.
- Environmental Microbiology, Vol. 3, Issue 2, p. 81-91
The Catalytic Valorization of Lignin for the Production of Renewable Chemicals
journal, June 2010
- Zakzeski, Joseph; Bruijnincx, Pieter C. A.; Jongerius, Anna L.
- Chemical Reviews, Vol. 110, Issue 6, p. 3552-3599
Complete genome sequence and comparative analysis of the metabolically versatile Pseudomonas putida KT2440
journal, December 2002
- Nelson, K. E.; Weinel, C.; Paulsen, I. T.
- Environmental Microbiology, Vol. 4, Issue 12, p. 799-808
Purification and characterization of pyrocatechase from the catecholassimilating yeast Candida maltosa.
journal, January 1988
- Gomi, Komakazu; Horiguchi, Sadayuki
- Agricultural and Biological Chemistry, Vol. 52, Issue 2, p. 585-587
Palladium catalysts on activated carbon supports
journal, January 2000
- Gurrath, M.; Kuretzky, T.; Boehm, H. P.
- Carbon, Vol. 38, Issue 8, p. 1241-1255
The β-Ketoadipate Pathway And The Biology Of Self-Identity
journal, October 1996
- Harwood, Caroline S.; Parales, Rebecca E.
- Annual Review of Microbiology, Vol. 50, Issue 1, p. 553-590
Automated design of synthetic ribosome binding sites to control protein expression
journal, October 2009
- Salis, Howard M.; Mirsky, Ethan A.; Voigt, Christopher A.
- Nature Biotechnology, Vol. 27, Issue 10, p. 946-950
Cleavage and hydrodeoxygenation (HDO) of C–O bonds relevant to lignin conversion using Pd/Zn synergistic catalysis
journal, January 2013
- Parsell, Trenton H.; Owen, Benjamin C.; Klein, Ian
- Chem. Sci., Vol. 4, Issue 2, p. 806-813
Engineering plant cell walls: tuning lignin monomer composition for deconstructable biofuel feedstocks or resilient biomaterials
journal, January 2014
- Ciesielski, Peter N.; Resch, Michael G.; Hewetson, Barron
- Green Chemistry, Vol. 16, Issue 5, p. 2627-2635
Continuous fermentation process and bioconversion-product recovery
patent, October 1984
- Hsieh, Jih-Han
- US Patent Document 4,480,034
Complete nucleotide sequence and polypeptide analysis of multicomponent phenol hydroxylase from Pseudomonas sp. strain CF600.
journal, December 1990
- Nordlund, I.; Powlowski, J.; Shingler, V.
- Journal of Bacteriology, Vol. 172, Issue 12, p. 6826-6833
PHAs Produced by Pseudomonas putida and Pseudomonas oleovorans Grown with n-Alkanoic Acids Containing Aromatic Groups
journal, September 1999
- Kim, Do Young; Rhee, Young Ha
- Macromolecules, Vol. 32, Issue 19, p. 6058-6064
The tac promoter: a functional hybrid derived from the trp and lac promoters
journal, January 1983
- de Boer, H. A.; Comstock, L. J.; Vasser, M.
- Proceedings of the National Academy of Sciences, Vol. 80, Issue 1, p. 21-25
Supported Iron Nanoparticles as Catalysts for Sustainable Production of Lower Olefins
journal, February 2012
- Torres Galvis, H. M.; Bitter, J. H.; Khare, C. B.
- Science, Vol. 335, Issue 6070, p. 835-838
Occurrence, metabolism, metabolic role, and industrial uses of bacterial polyhydroxyalkanoates.
journal, January 1990
- Anderson, A. J.; Dawes, E. A.
- Microbiological Reviews, Vol. 54, Issue 4