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Biological Conversion of Glycerol: A New Path to Renewable Chemicals and Fuels Ramon Gonzalez Department of Chemical & Biomolecular Engineering, Department of Bioengineering, Rice University

Renewable Chemicals and Fuels Linking PetroChemical and BioBased Industries Biobased Industry

Petrochemical Industry Crude oil and natural gas

Plant biomass and wastes

Hydrocarbons

Sugars, oils, etc.

Feedstocks and intermediates Fuels: Gasoline, diesel

Chemicals Materials

• National energy security • Climate protection • Sustainability • Economic growth Biofuels:

Fuels Bulk and Specialty Chemicals

Ethanol, biodiesel

Chemicals Bio-based Materials

Fuels & Chemicals from Biorenewables Challenges

Feedstock Engineering

Feedstock Deconstruction

Microbial Fermentation

Plant Biotechnology

Pretreatment and Hydrolysis

Biocatalysis

Recovery Distillation Extraction

Metabolic Engineering (MetEng) and Metabolic Evolution (MetEvo) STRAIN CONSTRUCTION Genetic engineering (gene/pathways “knockins” & “knockouts”); Mutagenesis & Selection

MetEng/MetEvo Cycle

DESIGN Integration (systems biology), Target Identification

STRAIN CHARACTERIZATION Tubes, Flask & Bioreactors

ANALYSIS Fermentation Profiling, Functional genomics

Fluxomics

Proteomics Transcriptomics

Metrics: Concentrations (g/L), Yields (g/g), Rates (g/L/h)

Oleochemical and Biodiesel Industries Glycerol/Glycerin as Inevitable Byproduct

Yazdani and Gonzalez (2007). Curr. Opin Biotechnol. 18: 213-219.

Biodiesel and Crude Glycerol US Production & Prices

Yazdani and Gonzalez (2007) Curr. Opin Biotechnol. 18: 213-219.

Solution? The Use of Anaerobic Fermentation of Glycerol as a Platform to Produce Reduced Chemicals and Fuels

Yazdani and Gonzalez (2007) Curr. Opin Biotechnol. 18: 213-219.

Why Anaerobic Fermentation of Glycerol? Relative and Absolute Reasons • Abundant: The production of biodiesel in the U.S. increased by 10-fold in the last two years: in million gallons, from 25 (2004) to 250 (2006). Each gallon of biodiesel inevitably generates 0.75 lb of glycerol. • Inexpensive. • Renewable/Green. • New Uses/Applications Needed. • Lower Capital/Operational Costs of Anaerobic Fermentations. • Highly Reduced State of Carbon (outperform sugars: see next slide).

Glycerol vs Sugars Redox Balance

Dharmadi, Murarka, Gonzalez. Biotechnol. Bioeng., 2006: 94: 821-829. Gonzalez et al. (MS in Review); Murarka et al. App. Environ. Microbiol., 2008: 74 (4); Yazdani & Gonzalez. (2007) Curr. Opin. Biotechnol. 18: 213-219.

Current State of Knowledge on Glycerol Metabolism in Enterobacteriaceae Established model for glycerol fermentation: Glycerol-fermenting species such as Klebsiella and Citrobacter utilize a two-branch pathway; the reductive, 1,3-PDO-producing branch acts as a sink for the reducing equivalents generated in the oxidative branch.

Respiratory metabolism of glycerol: Metabolism of glycerol in species such as E. coli, which do not synthesize 1,3-PDO, takes place through a respiratory pathway that requires an external electron acceptor. Gonzalez et al. (MS in Review); Murarka et al. App. Environ. Microbiol., 2008: 74 (4); Yazdani & Gonzalez. (2007) Curr. Opin. Biotechnol. 18: 213-219.

Our Findings: E. coli Ferments Glycerol in the Absence of Electron Acceptors For nearly 80 years, researchers had believed that the metabolism of glycerol in E. coli was restricted to respiratory conditions: i.e., the presence of an external electron acceptor. • Quastel JH, Stephenson M (1925). Biochem J. 19:660. • Quastel JH, Stephenson M, Whetham MD (1925). Biochem J. 14:304. • Lin EC (1976). Annu Rev Microbiol. 30:535-78. • Booth I (2005). In Neidhardt FC et al., (ed.), E. coli and Salmonella: cellular and molecular biology, Web Edition. ASM Press, Washington, DC. Available at www.ecosal.org.

Glycerol

µ =0.041 h-1

Growth

Ethanol Other Products

Dharmadi, Murarka, Gonzalez. Biotechnol. Bioeng., 2006: 94: 821-829. Gonzalez et al. (MS in Review); Murarka et al. App. Environ. Microbiol., 2008: 74 (4); Yazdani & Gonzalez. (2007) Curr. Opin. Biotechnol. 18: 213-219.

Can we Change the Biodiesel Industry with Glycerol Fermentation? Feedstock and Operating Costs for B100 Component/Kind of Cost

Cost in $/gal. biodiesel (12/06)

Soy Oil

2.381

Methanol

0.202

Processing Costs

0.211

(Feedstock + Operating) Costs

2.794

B100 Market Price

2.750

Byproduct (Glycerin) Credit

0.021 (@0.025 $/lb)

“Byproduct Ethanol-H2/Formic credit” 0.150-0.250 “Byproduct Succinic Acid Credit”

0.600-1.000

Co-production of Ethanol-Formic Strain SY04 (pZSKLMgldA) Growth

Glycerol

EtOH Formic Byproducts

Product yields: ~ 95% (mol EtOH or formate/mol glycerol) Specific Rates: ~ 30 mmol product/gCell/h

Yazdani and Gonzalez (MS in Review)

Co-Production of: (1) EtOH-Formic or (2) EtOH-H2 Data represents close to maximum theoretical yield for all products

SY03 (pZSKLMgldA) Strain 2

SY04 (pZSKLMgldA)

Formate or Hydrogen can never be co-produced along with ethanol if sugars are used instead of glycerol. The use of glycerol results in more energy- and carbon-efficient processes. Dharmadi, Murarka, Gonzalez. Biotechnol. Bioeng., 2006: 94: 821-829. Gonzalez et al. (MS in Review); Murarka et al. App. Environ. Microbiol., 2008: 74 (4); Yazdani & Gonzalez. (2007) Curr. Opin. Biotechnol. 18: 213-219.

Ethanol-Formic and Ethanol-H2 from Glycerol * Feedstock cost is “net” for cornethanol (include revenue from coproducts) but not for glycerol-derived ethanol (does not include revenue from co-products H2 and formic acid) Capital cost significantly lower than in corn-ethanol plant. Yazdani and Gonzalez (2007) Curr. Opin Biotechnol. 18: 213-219.

Can we Change the Biodiesel Industry with Glycerol Fermentation? Feedstock and Operating Costs for B100 Component/Kind of Cost

Cost in $/gal. biodiesel (12/06)

Soy Oil

2.381

Methanol

0.202

Processing Costs

0.211

(Feedstock + Operating) Costs

2.794

B100 Market Price

2.750

Byproduct (Glycerin) Credit

0.021 (@0.025 $/lb)

“Byproduct Ethanol-H2/Formic credit” 0.150-0.250 “Byproduct Succinic Acid Credit”

0.600-1.000

Acknowledgements Graduate Students:

Postdoc:

Y. Dharmadi A. Gupta G. Durnin

S. Yazdani

A. Murarka J. Clomburg

USDA - National Research Initiative of the USDA Cooperative State Research, Education and Extension Service (2005-3550415222/16698) NSF- Division of Chemical, Bioengineering, Environmental, and Transport Systems (CBET-0601549)