Abstract
Renewable and bio-based transportation fuel sources can lower the life-cycle greenhouse gas emissions from vehicles. We present an initial assessment of ethyl 3-ethoxybutyrate (EEB) as a biofuel in terms of its performance as a fuel oxygenate and its persistence in the environment. EEB can be produced from ethanol and poly-3-hydroxybutyrate, a bacterial storage polymer that can be produced from non-food biomass and other organic feedstocks. Physicochemical properties of EEB and fuel-relevant properties of EEB-gasoline blends were measured, emissions of criteria pollutants from EEB as a gasoline additive in a production vehicle were evaluated, and fate and persistence of EEB in the environment were estimated. EEB solubility in water was 25.8 g/L, its Kow was 1.8, and its Henry’s Law constant was 1.04 × 10−5 atm-m3/mole. The anti-knock index values for 5 and 20 % v/v EEB-gasoline blends were 91.6 and 91.9, respectively. Reductions in fuel economy were consistent with the level of oxygenation, and criteria emissions were met by the vehicle operated over the urban dynamometer driving cycle (FTP 75). Predicted environmental persistence ranged from 15 to 30 days which indicates that EEB is not likely to be a persistent organic pollutant. In combination, these results suggest a high potential for the use of EEB as a renewable fuel source.
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References
Aakko-Saksa PT, Rantanen-Kolehmainen L, Skyttä E (2014) Ethanol, isobutanol, and biohydrocarbons as gasoline components in relation to gaseous emissions and particulate matter. Environ Sci Technol 48:10489–10496
Aastveit KA, Bjørnland HC, Thorsrud LA (2014) What drives oil prices? Emerging versus developed economies. J Appl Econ. doi:10.1002/jae.2406
Aceves S, Glaser R, Richardson J (1997) Assessment of California reformulated gasoline impact on vehicle fuel economy. Department of Energy UCRL-ID-126551
Aguilera RF (2014) Production costs of global conventional and unconventional petroleum. Energ Policy 64:134–140
Amine M, Zahran MAH, Awad EN, El-Zein SM, Barakat Y (2013) Volatility criteria and specifications of some gasoline-ester blends. Inter J Mod Org Chem 2:226–250
Ang BW, Choong WL, Ng TS (2015) Energy security: definitions, dimensions and indexes. Renew Sust Energ Rev 42:1077–1093
Bunce MP, Storey JME, Edmonds JW, et al. (2015) Ethyl 3-ethoxybutyrate, a new component of the transportation renewable fuel portfolio. Fuel 161:262–268
Cashin P, Mohaddes K, Raissi M, Raissi M (2014) The differential effects of oil demand and supply shocks on the global economy. Energy Econ 44:113–134
da Silva R, Cataluna R, Weber de Menezes E, Samios D, Sartori Piatnicki CM (2005) Effect of additives on the antiknock properties and Reid vapor pressure of gasoline. Fuel 84:951–959
Dabbagh HA, Ghobadi F, Ehsani MR, Moradmand M (2013) The influence of ester additives on the properties of gasoline. Fuel 104:216–223
Davis SJ, Caldeira K, Matthews HD (2010) Future CO2 emissions and climate change from existing energy infrastructure. Science 329:1330–1333
Energy Independence and Security Act of 2007 (2007) Public Law 110–140. Code of Federal Regulations
Ha Y, Kwon J-H (2010) Determination of 1-octanol-air partition coefficient using gaseous diffusion in the air boundary layer. Environ Sci Technol 44:3041–3046
Hochhauser AM, Benson JD, Burns VR, Gorse RA Jr, Koehl WJ, Painter LJ, Reuter RM, Rutherford JA (1993) Fuel composition effects on automotive fuel economy-auto/oil air quality improvement research program. SAE Tech. Paper 930138
Johnson BE, Stovell C, Matthews R, Kirwan J, Ng H, Larsen R (2000) Effects of fuel parameters on FTP emissions of a 1998 Toyota with a direct injection spark ignition engine. SAE Tech. Paper 2000–01-1907
Karavalakis G, Short D, Russell RL, Jung H, Johnson KC, Asa-Awuku A, Durbin TD (2014) Assessing the impacts of ethanol and isobutanol on gaseous and particulate emissions from flexible fuel vehicles. Environ Sci Technol 48:14016–14024
Kavanaugh M, Chowdhury Z, Kommineni S, et al. (2003) Removal of MTBE with advanced oxidation processes. IWA Publishing, London
Kilian L (2014) Oil price shocks: causes and consequences. Ann Rev Resour Econ 6:133–154
Kirchstetter TW, Singer BC, Harley RA, Kendall GR, Traverse M (1999) Impact of California reformulated gasoline on motor vehicle emissions. 1. Mass emission rates. Environ Sci Technol 33:318–328
Knoll K, West B, Huff S, Thomas J, Orban J, Cooper C (2009) Effects of mid-level ethanol blends on conventional vehicle emissions. SAE Tech. Paper 2009–01-2723
Lee WS, Chua ASM, Yeoh HK, Ngoh GC (2014) A review of the production and applications of waste-derived volatile fatty acids. Chem Eng J 235:83–99
Masum BM, Masjuki HH, Kalam MA, Fattah IMR, Palash SM, Abedin MJ (2013) Effect of ethanol–gasoline blend on NO x emission in SI engine. Renew Sust Energ Rev 24:209–222
McMurry ZA, Smoot JC (2013) Process for producing a renewable biofuel from waste water treatment plants. U.S. Patent No. 8377151
Mohrig JR, Fu SS, King RW, Warnet R, Gustafson G (1990) Stereochemistry of nucleophilic conjugate addition. Addition of ethanol-d and 2-methyl-2-propanethiol-d to ethyl crotonate. J Am Chem Soc 112:3665–3667
Office of Ground Water and Drinking Water (OGWDW) (2008) MTBE. In: Regulatory determinations support document for selected contaminants from the second drinking water contaminant candidate list (CCL 2). U.S. EPA, Washington, D.C.
Oh C, Cha G (2013) Influence of oxygenate content on particulate matter emission in gasoline direct injection engine. Int J Automot Technol 14:829–836
Organization for Economic Co-operation and Development (OECD) (1995a) Test No. 105: Water solubility. In: OECD guidelines for the testing of chemicals, section 1. OECD Publishing, Paris
Organization for Economic Co-operation and Development (OECD) (1995b) Test No. 107: Partition coefficient (n-octanol/water), shake flask method. In: OECD guidelines for the testing of chemicals, section 1. OECD Publishing, Paris
Panel on Alternative Liquid Transportation Fuels (PALTF) (2009) Liquid transportation fuels from coal and biomass: technological status, costs, and environmental impacts. The National Academies Press, Washington, D.C.
Ratcliff MA, Luecke J, Williams A, et al. (2013) Impact of higher alcohols blended in gasoline on light-duty vehicle exhaust emissions. Environ Sci Technol 47:13865–13872
Scheringer M, MacLeod M, Wegmann F (2009) The OECD P OV and LRTP screening tool, version 2.2 user’s manual. www.oecd.org/dataoecd/36/38/45373514.pdf
Schifter I, Diaz L, Vera M, Guzman E, Lopez-Salinas E (2004) Fuel formulation and vehicle exhaust emissions in Mexico. Fuel 83:2065–2074
Serafim LS, Lemos PC, Albuquerque MGE, Reis MAM (2008) Strategies for PHA production by mixed cultures and renewable waste materials. Appl Microbiol Biotechnol 81:615–628
Storey JME, Lewis SA, Norman K, Barone TL (2010) Ethanol blend effects on direct injection spark-ignition gasoline vehicle particulate matter emissions. SAE Int J Fuels Lubr 3:650–659
United States Energy Information Administration (U.S. EIA) (2014) International energy outlook 2014: world petroleum and other liquid fuels. DOE/EIA-0484
United States Environmental Protection Agency (U.S. EPA) (2008) Estimation programs Interface Suite™ for Microsoft® Windows, v 4.00. U.S. EPA, Washington, D.C.
Verschueren K (1996) Handbook of environmental data on organic chemicals, 3rd edn. Van Nostrand Reinhold, New York
Wang SY, Wang Z, Liu MM, Xu Y, Zhang XJ, Chen G-Q (2010) Properties of a new gasoline oxygenate blend component: 3-hydroxybutyrate methyl ester produced from bacterial poly-3-hydroxybutyrate. Biomass Bioenergy 34:1216–1222
Wegmann F, Cavin L, MacLeod M, Scheringer M, Hungerbühler K (2009) The OECD software tool for screening chemicals for persistence and long-range transport potential. Environ Model Softw 24:228–237
West BH, Sluder CS, Knoll K, Orban JE, Feng J (2012) Intermediate ethanol blends catalyst durability program. ORNL/TM-2011/234
Won D, Corsi RL, Rynes M (2000) New indoor carpet as an adsorptive reservoir for volatile organic compounds. Environ Sci Technol 34:4193–4198
Zhang X, Luo R, Wang Z, Deng Y, Chen G-Q (2009) Application of (R)-3-hydroxyalkanoate methyl esters derived from microbial polyhydroxyalkanoates as novel biofuels. Biomacromolecules 10:707–711
Acknowledgments
We thank J. Brown for technical assistance provided during EEB synthesis and purification and the FEERC technical support staff for assistance provided during vehicle testing. C/e- Solutions, Inc. received financial support from the National Science Foundation (grant no. IIP-1013100). The sponsor had no involvement in the design, execution, or publication of the work reported here. C/e- Solutions, Inc. personnel were involved in all aspects of the work.
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Dr. Smoot and Mr. McMurry are holders of U.S. Patent No. 7641706 and U.S. Patent No. 8377151.
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Storey, J.M.E., Bunce, M.P., Clarke, E.M. et al. Pollutant emissions and environmental assessment of ethyl 3-ethoxybutyrate, a potential renewable fuel. Environ Sci Pollut Res 23, 18575–18584 (2016). https://doi.org/10.1007/s11356-016-7052-z
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DOI: https://doi.org/10.1007/s11356-016-7052-z