Amines have lower sooting tendencies than analogous alkanes, alcohols, and ethers

Montgomery, Matthew J.; Zhu, Junqing; Pfefferle, Lisa D.; McEnally, Charles S.

doi:10.1016/j.combustflame.2021.01.016

Amines have lower sooting tendencies than analogous alkanes, alcohols, and ethers

Journal Article · Fri Jan 22 00:00:00 EST 2021 · Combustion and Flame

DOI:https://doi.org/10.1016/j.combustflame.2021.01.016· OSTI ID:1763715

^[1]; Zhu, Junqing ^[2]; Pfefferle, Lisa D. ^[2]; McEnally, Charles S. ^[2]

Yale Univ., New Haven, CT (United States); Yale University
Yale Univ., New Haven, CT (United States)

While the sooting tendencies of regular hydrocarbons, oxygenates, and complex fuel mixtures have been well-studied, far less research has been devoted to analyzing the influence of fuel-nitrogen on soot formation. The effect of nitrogen on soot formation becomes relevant for diesel fuels with nitrogen-containing additives, as well as biomass or biomass-derived fuels, which can contain up to 30% nitrogen-containing compounds by dry weight. To begin closing these gaps in the literature, the sooting tendencies of 14 C4 and C6 amines were measured. Sooting tendencies were quantified by re-scaling relative soot concentrations measured in fuel-doped methane flames into Yield Sooting Indices (YSI). The relative soot concentrations were measured with line-of-sight spectral radiance, and validation experiments confirmed that the presence of nitrogen in the test compounds did not interfere with this diagnostic. All of these amines had lower sooting tendencies than the structurally analogous hydrocarbons and oxygenates. The sooting tendencies of amine isomers with the same chemical formula varied significantly. Secondary amines with linear substituents were found to offer the lowest sooting propensity, while primary amines with branched substituents were observed to yield the largest sooting tendencies. In conclusion, the relationship between sooting propensity and chemical structure of the amines hints at the complex nature of soot formation, and highlights an interesting and unexplored area of combustion chemistry for further studies.

View Accepted Manuscript (DOE)

Research Organization:: Yale Univ., New Haven, CT (United States)

Sponsoring Organization:: National Science Foundation (NSF); USDOE; USDOE Office of Energy Efficiency and Renewable Energy (EERE), Transportation Office. Vehicle Technologies Office

Grant/Contract Number:: EE0007983

OSTI ID:: 1763715

Alternate ID(s):: OSTI ID: 1775653

Journal Information:: Combustion and Flame, Journal Name: Combustion and Flame Vol. 227; ISSN 0010-2180

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (44)

Biofuel Combustion Chemistry: From Ethanol to Biodiesel Kohse-Höinghaus, Katharina; Oßwald, Patrick; Cool, Terrill A. Angewandte Chemie International Edition, Vol. 49, Issue 21 https://doi.org/10.1002/anie.200905335	journal	May 2010
Bounding the role of black carbon in the climate system: A scientific assessment: BLACK CARBON IN THE CLIMATE SYSTEM Bond, T. C.; Doherty, S. J.; Fahey, D. W. Journal of Geophysical Research: Atmospheres, Vol. 118, Issue 11 https://doi.org/10.1002/jgrd.50171	journal	June 2013
The prediction of laminar jet diffusion flame sizes: Part I. Theoretical model Roper, F. G. Combustion and Flame, Vol. 29 https://doi.org/10.1016/0010-2180(77)90112-2	journal	January 1977
Effect of molecular structure on incipient soot formation Calcote, H. F.; Manos, D. M. Combustion and Flame, Vol. 49, Issue 1-3 https://doi.org/10.1016/0010-2180(83)90172-4	journal	January 1983
Some effects of molecular structure of single hydrocarbons on sooting tendency Ladommatos, Nicos; Rubenstein, Paul; Bennett, Paul Fuel, Vol. 75, Issue 2 https://doi.org/10.1016/0016-2361(94)00251-7	journal	January 1996
Nitrogen functionality in coals and coal-tar pitch determined by X-ray photoelectron spectroscopy Buckley, Alan N. Fuel Processing Technology, Vol. 38, Issue 3 https://doi.org/10.1016/0378-3820(94)90046-9	journal	June 1994
Two-stage ignition in HCCI combustion and HCCI control by fuels and additives Tanaka, S. Combustion and Flame, Vol. 132, Issue 1-2 https://doi.org/10.1016/S0010-2180(02)00457-1	journal	January 2003
Ignition of alkyl nitrate/oxygen/argon mixtures in shock waves and comparisons with alkanes and amines Toland, Adrian; Simmie, John M. Combustion and Flame, Vol. 132, Issue 3 https://doi.org/10.1016/S0010-2180(02)00504-7	journal	February 2003
Simultaneous measurements of soot volume fraction and particle size / microstructure in flames using a thermophoretic sampling technique Köylü, Ü. Ö.; McEnally, C. S.; Rosner, D. E. Combustion and Flame, Vol. 110, Issue 4 https://doi.org/10.1016/S0010-2180(97)00089-8	journal	September 1997
Biomass production, total protein, chlorophylls, lipids and fatty acids of freshwater green and blue-green algae under different nitrogen regimes Piorreck, Margret; Baasch, Klaus-Hinnerk; Pohl, Peter Phytochemistry, Vol. 23, Issue 2 https://doi.org/10.1016/S0031-9422(00)80304-0	journal	January 1984
Global, regional, and national comparative risk assessment of 84 behavioural, environmental and occupational, and metabolic risks or clusters of risks for 195 countries and territories, 1990–2017: a systematic analysis for the Global Burden of Disease Study 2017 Stanaway, Jeffrey D.; Afshin, Ashkan; Gakidou, Emmanuela The Lancet, Vol. 392, Issue 10159 https://doi.org/10.1016/S0140-6736(18)32225-6	journal	November 2018
Molecular composition of organic fine particulate matter in Houston, TX Fraser, M. P.; Yue, Z. W.; Tropp, R. J. Atmospheric Environment, Vol. 36, Issue 38 https://doi.org/10.1016/S1352-2310(02)00725-2	journal	December 2002
Seasonal trends in PM2.5 source contributions in Beijing, China Zheng, Mei; Salmon, Lynn G.; Schauer, James J. Atmospheric Environment, Vol. 39, Issue 22 https://doi.org/10.1016/j.atmosenv.2005.03.036	journal	July 2005
Global biomass fuel resources Parikka, Matti Biomass and Bioenergy, Vol. 27, Issue 6 https://doi.org/10.1016/j.biombioe.2003.07.005	journal	December 2004
Protein extraction from biomass in a bioethanol refinery – Possible dietary applications: Use as animal feed and potential extension to human consumption Chiesa, Simone; Gnansounou, Edgard Bioresource Technology, Vol. 102, Issue 2 https://doi.org/10.1016/j.biortech.2010.07.125	journal	January 2011
Bio-oil and bio-char from low temperature pyrolysis of spent grains using activated alumina Sanna, Aimaro; Li, Sujing; Linforth, Rob Bioresource Technology, Vol. 102, Issue 22 https://doi.org/10.1016/j.biortech.2011.08.092	journal	November 2011
Quantitative analysis of nitrogen containing compounds in microalgae based bio-oils using comprehensive two-dimensional gas-chromatography coupled to nitrogen chemiluminescence detector and time of flight mass spectrometer Toraman, Hilal E.; Franz, Kristina; Ronsse, Frederik Journal of Chromatography A, Vol. 1460 https://doi.org/10.1016/j.chroma.2016.07.009	journal	August 2016
Improved sooting tendency measurements for aromatic hydrocarbons and their implications for naphthalene formation pathways Mcenally, C.; Pfefferle, L. Combustion and Flame, Vol. 148, Issue 4 https://doi.org/10.1016/j.combustflame.2006.11.003	journal	March 2007
Structural group analysis for soot reduction tendency of oxygenated fuels Pepiotdesjardins, P.; Pitsch, H.; Malhotra, R. Combustion and Flame, Vol. 154, Issue 1-2 https://doi.org/10.1016/j.combustflame.2008.03.017	journal	July 2008
Sooting characteristics of surrogates for jet fuels Mensch, Amy; Santoro, Robert J.; Litzinger, Thomas A. Combustion and Flame, Vol. 157, Issue 6 https://doi.org/10.1016/j.combustflame.2010.02.008	journal	June 2010
Combustion chemistry and fuel-nitrogen conversion in a laminar premixed flame of morpholine as a model biofuel Lucassen, Arnas; Labbe, Nicole; Westmoreland, Phillip R. Combustion and Flame, Vol. 158, Issue 9 https://doi.org/10.1016/j.combustflame.2011.02.010	journal	September 2011
Fuel-nitrogen conversion in the combustion of small amines using dimethylamine and ethylamine as biomass-related model fuels Lucassen, Arnas; Zhang, Kuiwen; Warkentin, Julia Combustion and Flame, Vol. 159, Issue 7 https://doi.org/10.1016/j.combustflame.2012.02.024	journal	July 2012
Group additivity in soot formation for the example of C-5 oxygenated hydrocarbon fuels Barrientos, Eduardo J.; Lapuerta, Magín; Boehman, André L. Combustion and Flame, Vol. 160, Issue 8 https://doi.org/10.1016/j.combustflame.2013.02.024	journal	August 2013
Shock tube study of ethylamine pyrolysis and oxidation Li, Sijie; Davidson, David F.; Hanson, Ronald K. Combustion and Flame, Vol. 161, Issue 10 https://doi.org/10.1016/j.combustflame.2014.04.002	journal	October 2014
Sooting tendencies of unsaturated esters in nonpremixed flames Das, Dhrubajyoti D.; McEnally, Charles S.; Pfefferle, Lisa D. Combustion and Flame, Vol. 162, Issue 4 https://doi.org/10.1016/j.combustflame.2014.11.012	journal	April 2015
Measuring and predicting sooting tendencies of oxygenates, alkanes, alkenes, cycloalkanes, and aromatics on a unified scale Das, Dhrubajyoti D.; St. John, Peter C.; McEnally, Charles S. Combustion and Flame, Vol. 190 https://doi.org/10.1016/j.combustflame.2017.12.005	journal	April 2018
Compositional analysis of bio-oil derived from pyrolysis of seaweed Wang, Shuang; Wang, Qian; Jiang, Xiumin Energy Conversion and Management, Vol. 68 https://doi.org/10.1016/j.enconman.2013.01.014	journal	April 2013
An overview of the chemical composition of biomass Vassilev, Stanislav V.; Baxter, David; Andersen, Lars K. Fuel, Vol. 89, Issue 5 https://doi.org/10.1016/j.fuel.2009.10.022	journal	May 2010
Combustion characteristics of different biomass fuels Demirbas, A. Progress in Energy and Combustion Science, Vol. 30, Issue 2 https://doi.org/10.1016/j.pecs.2003.10.004	journal	January 2004
Flame structure studies of premixed ammonia/hydrogen/oxygen/argon flames: Experimental and numerical investigation Duynslaegher, C.; Jeanmart, H.; Vandooren, J. Proceedings of the Combustion Institute, Vol. 32, Issue 1 https://doi.org/10.1016/j.proci.2008.06.036	journal	January 2009
Sooting tendencies of co-optima test gasolines and their surrogates McEnally, Charles S.; Xuan, Yuan; St. John, Peter C. Proceedings of the Combustion Institute, Vol. 37, Issue 1 https://doi.org/10.1016/j.proci.2018.05.071	journal	January 2019
Analyzing the robustness of the yield sooting index as a measure of sooting tendency Montgomery, Matthew J.; Das, Dhrubajyoti D.; McEnally, Charles S. Proceedings of the Combustion Institute, Vol. 37, Issue 1 https://doi.org/10.1016/j.proci.2018.06.105	journal	January 2019
Effect of ammonia addition on suppressing soot formation in methane co-flow diffusion flames Montgomery, Matthew J.; Kwon, Hyunguk; Dreyer, Jochen A. H. Proceedings of the Combustion Institute https://doi.org/10.1016/j.proci.2020.06.094	journal	August 2020
Why Combustions Are Always Exothermic, Yielding About 418 kJ per Mole of O ₂ Schmidt-Rohr, Klaus Journal of Chemical Education, Vol. 92, Issue 12 https://doi.org/10.1021/acs.jchemed.5b00333	journal	September 2015
Novel Micropyrolyis Index (MPI) to Estimate the Sooting Tendency of Fuels Crossley, Steven P.; Alvarez, Walter E.; Resasco, Daniel E. Energy & Fuels, Vol. 22, Issue 4 https://doi.org/10.1021/ef800058y	journal	July 2008
Sooting Tendencies of Oxygenated Hydrocarbons in Laboratory-Scale Flames McEnally, Charles S.; Pfefferle, Lisa D. Environmental Science & Technology, Vol. 45, Issue 6 https://doi.org/10.1021/es103733q	journal	March 2011
Relation of Smoke Point to Molecular Structure Hunt, Russell A. Industrial & Engineering Chemistry, Vol. 45, Issue 3 https://doi.org/10.1021/ie50519a039	journal	March 1953
Chemical Kinetic Modeling Study of the Effects of Oxygenated Hydrocarbons on Soot Emissions from Diesel Engines ^† Westbrook, Charles K.; Pitz, William J.; Curran, Henry J. The Journal of Physical Chemistry A, Vol. 110, Issue 21 https://doi.org/10.1021/jp056362g	journal	June 2006
Characterization and utilization of aqueous products from hydrothermal conversion of biomass for bio-oil and hydro-char production: a review Usman, Muhammad; Chen, Huihui; Chen, Kaifei Green Chemistry, Vol. 21, Issue 7 https://doi.org/10.1039/C8GC03957G	journal	January 2019
Distributions of carbon and nitrogen in the products from hydrothermal liquefaction of low-lipid microalgae Yu, Guo; Zhang, Yuanhui; Schideman, Lance Energy & Environmental Science, Vol. 4, Issue 11 https://doi.org/10.1039/c1ee01541a	journal	January 2011
Fuel Additive Effects on Soot Across a Suite of Laboratory Devices, Part 2: Nitroalkanes Litzinger, T.; Colket, M.; Kahandawala, M. Combustion Science and Technology, Vol. 183, Issue 8 https://doi.org/10.1080/00102202.2010.539293	journal	April 2011
An Improved Method of Smoke Point Normalization Li, Liming; Sunderland, Peter B. Combustion Science and Technology, Vol. 184, Issue 6 https://doi.org/10.1080/00102202.2012.670333	journal	June 2012
The conversion of chicken manure to bio-oil by fast pyrolysis. III. Analyses of chicken manure, bio-oils and char by Py-FIMS and Py-FDMS Schnitzer, Morris I.; Monreal, Carlos M.; Jandl, Gerald Journal of Environmental Science and Health, Part B, Vol. 43, Issue 1 https://doi.org/10.1080/03601230701735185	journal	December 2007
Yale Coflow Burner Information and CAD Drawings Gau, Jeffrey; Das, Dhrubajyoti; McEnally, Charles figshare https://doi.org/10.6084/m9.figshare.5005007.v1	dataset	January 2017

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Amines
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Nonpremixed flame
Soot
Sooting tendency

Amines have lower sooting tendencies than analogous alkanes, alcohols, and ethers

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References (44)

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