Natural Oil Polythiols and Polyols– A Life Cycle Comparison Thomas A. Upshaw, William J. Young, Eric J. Netemeyer Chevron Phillips Chemical Co., LP World Adhesive Conference & EXPO April 22, 2008 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Adhesives and Sealants Council World Adhesive Conference 2008 Outline Product, properties, applications summary Study objectives Modeling tools and information sources Modeled systems and assumptions Mercaptanized soybean oil (MSO) Petrochemical (flexible polyether) polyol Castor oil LCA Methodology Impact results and BEES ratings Conclusions 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Soy Polythiol – MSO (Polymercaptan 358) 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Potential Application Areas for Soy Polythiols Benefits: High biobased content Adhesion Hydrophobicity Weathering/UV stability Antioxidant properties Chemical & corrosion resistance Higher refractive index Applications Adhesives Sealants Coatings Technologies Polyurethanes Epoxy resins Free radical/UV systems 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Adhesives and Sealants Council World Adhesive Conference 2008 Objectives Develop a soy polythiol life cycle inventory (LCI) platform for product life cycle assessment through the product manufacturing stage Compare life cycle environmental impacts using updated castor and petrochemical (polyether) polyol LCI data 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Life Cycle Modeling Tools SimaPro 7.0 software, using SimaPro 7.0 database and U.S. LCI database BEES (Building for Environmental and Economic Sustainability) impact model software NIST sponsored & EPA supported Methodology used by USDA BioPreferred program Conducted in accordance with ISO 14040:1997(E) standard TRACI (Tool for the Reduction and Assessment of Chemical and other Environmental Impacts) – EPA life cycle impact assessment method 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Adhesives and Sealants Council World Adhesive Conference 2008 Data Sources Soybean data Agriculture data from U.S. LCI database Processing data from NREL LCA report on biodiesel 1998 Soy Polythiol – Chevron Phillips Chemical Co. Process inputs estimated from commercial production facility, assuming conventional H2S process technology Petroleum (flexible polyether) polyol U.S. LCI database data Castor oil Purdue University article and various internet sources Incomplete process data supplemented by analogous data on other seed oils in U.S. LCI database 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Petro Polyol System Boundaries Process energy Air emissions Upstream mat’ls & energy production Water effluents Raw matls production, transport Waste Process energy Polyol production (avg plant data) Air emissions Water effluents Raw matls production, transport Waste Transportation to the customer Truck transport Polyol delivered to the customer 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Petro Polyol Assumptions Consolidated proprietary information for 5 North American plants, 2003-5 data Polyether polyol, glycerin-initiated, 3500 mol wt (on average) KOH-catalyzed, solvent, water-washed 7.6 to 1 wt ratio PO/EO 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Adhesives and Sealants Council World Adhesive Conference 2008 MSO System Boundaries Upstream Materials Soybean production Process energy Air emissions Water effluents Soy oil production & refining Matls production, transport Waste Process energy MSO production Air emissions Matls production, transport Transportation to the customer Truck transport MSO delivered to the customer 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

MSO Polythiol Assumptions Designed process based on existing plant capabilities at Borger TX facility: UV reactor Estimated stoichiometric excess of H2S Stripping and recycle of H2S Known reaction conditions from lab/pilot work Conventional energy sources (nat. gas) 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Castor Oil System Boundaries Upstream Materials Castor beans production Process energy Air emissions Matls production, transport Water effluents Castor oil production & refining Waste Truck transport Transportation from India to the customer Barge transport Castor oil delivered to the customer 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Castor Oil Assumptions Complete data were not available Significant uncertainty, need better data Analogous LCI data for other seed oils were used (adjusted for 45-55% castor oil yield) Irrigation water assumed similar to soy process Since rapid growth and modernization of castor agriculture is projected based on drive for growing biodiesel production, mechanized production and irrigation were assumed 8200 mile barge transport from India to U.S. market assumed before distribution 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Adhesives and Sealants Council World Adhesive Conference 2008 LCA Methodology LCAs built in SimaPro 7.0 software Impact methods and weighting – BEES 4.0 (NIST) Life Cycle Inventory – quantified listing of inflows and outflows per 1000 lbs of product Converted to equivalent units per 1000 lbs and combined into LCIA impact categories Normalized to unitless dimensions corresponding to fraction of total U.S. impact per year per capita Overall BEES environmental score: sum of normalized impacts weighted by importance 2006 BEES Stakeholder Panel 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Adhesives and Sealants Council World Adhesive Conference 2008 Impact Comparison 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Adhesives and Sealants Council World Adhesive Conference 2008 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Adhesives and Sealants Council World Adhesive Conference 2008 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Adhesives and Sealants Council World Adhesive Conference 2008 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Adhesives and Sealants Council World Adhesive Conference 2008 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Adhesives and Sealants Council World Adhesive Conference 2008 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

BEES weighting factors 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Adhesives and Sealants Council World Adhesive Conference 2008 Weighted BEES Scores Caveats: Weighting factors are subjective and change based on the emphasis of the stakeholders and society’s relative concern about each impact factor. Weighted results change as LCI database data updates occur. ISO standard does not recommend using single score comparisons. 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Adhesives and Sealants Council World Adhesive Conference 2008 Conclusions Global warming potential of MSO and castor oil are significantly lower than the petroleum-based polyol due to the crop oil raw material source. Future use of renewable energy for MSO production would result in a significant reduction in global warming potential (GWP) and fossil fuel consumption. Next generation process technology currently under development is expected to significantly reduce fossil fuel consumption, GWP and SOx generation (i.e., criteria air pollutant and acidification impacts). Castor oil is comparable to MSO by weighted BEES score, but further analysis with better life cycle input data is needed Castor score was expected to be lower since the oil is not further chemically converted, but suffered from the use of the solvent extraction process and (probably high) estimated fertilizer use 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Adhesives and Sealants Council World Adhesive Conference 2008 Acknowledgements Adhesives and Sealants Council Jim Pollack, OmniTech International Ltd. Anne Landfield Greig, Four Elements Consulting, LLC Chevron Phillips Chemical Company, LP 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008

Backup slides

Adhesives and Sealants Council World Adhesive Conference 2008 Data Sources Soybean data Agriculture data from U.S. LCI database (data updated 2003 by NIST/USDA Biobased Advisory Group) Processing data from NREL LCA report on biodiesel 1998 Soy Polythiol – Chevron Phillips Chemical Co. Process inputs estimated from commercial production facility, assuming conventional H2S process technology Petroleum (flexible polyether) polyol U.S. LCI database (Plastics Industry LCI Study 2003-5) Castor oil Purdue University article Incomplete data supplemented by analogy to other seed oils: Corn production module of U.S. LCI database (Fertilizers, energy) Sunflower seed data (herbicides, pesticides) Soybean data for irrigation 4/22/2008 Adhesives and Sealants Council World Adhesive Conference 2008