Analysis of Oxygenated Compounds in Hydrotreated Biomass Fast Pyrolysis Oil Distillate Fractions
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- Marylou Gregory
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1 Supporting Information for: Analysis of Oxygenated s in Hydrotreated Biomass Fast Pyrolysis Oil Distillate Fractions Earl D. Christensen, * Gina Chupka, * Jon Luecke, * Tricia Smurthwaite, Teresa L. Alleman, * Kristiina Iisa, * James A. Franz, Douglas C. Elliott, Robert L. McCormick * * National Renewable Energy Laboratory, Golden, CO, USA 80401, Pacific Northwest National Laboratory, Richland, WA USA Table S-1: GC Parameters for Restek Rtx-1701 Column (Cat# 12026) Injection Port Temperature 250 C Injection Volume 1.0 µl Initial Oven Temperature 50 C Initial Hold Time Oven Ramp Rate 1 min 7 C/min Final Oven Temperature 250 C Final Hold Time Helium Carrier Flow Rate 5 min 1 ml/min Split Ratio 50:1 Detector Transfer Line 250 C
2 Table S-2: GC Parameters for Agilent DB-1 Column (Cat# ) Injection Port Temperature 300 C Injection Volume 1.0 µl Initial Oven Temperature 50 C Initial Hold Time Oven Ramp Rate 1 min 7 C/min Final Oven Temperature 350 C Final Hold Time Helium Carrier Flow Rate 5 min 1 ml/min Split Ratio 50:1 Detector Transfer Line 300 C
3 Table S-3: Acid and Phenol Standard s for Volatile Acid Analysis Name Formic Acid 8.86 Acetic Acid 9.43 Propionic Acid Isobutyric Acid Butyric Acid Isovaleric Acid Valeric Acid Methyl Pentanoic Acid Hexanoic Acid Phenol Heptanoic Acid o-cresol m-cresol p-cresol Ethyl Phenol 54.69
4 Table S-4: Mobile Phase Gradient for HPLC Carbonyl Analysis Mobile Phase: A. 18 MΩ DI Water B. HPLC Grade Acetonitrile Time % A % B (min) End End
5 Table S-5: Carbonyl Standard s Name Time (min) Formaldehyde 4.66 Acetaldehyde 5.68 Acrolein 6.74 Acetone 6.96 Propionaldehyde 7.18 Crotonaldehyde 8.06 Methacrolein 8.42 Butyraldehyde 8.66 Methyl-ethyl-ketone 8.92 Isovaleraldehyde / Benzaldehyde (Co-elute) 9.95 Valeraldehyde Cyclohexanone o,m,p-tolualdehyde (Co-elute) Hexaldehyde ,5-Dimethylbenzaldehyde 11.43
6 Table S-6: HT-138 Lights Tentatively Identified s by GC-MS Tentatively Identified Time (min) Acetic acid acid 1-Butanol alcohol Pentane, 3-methyl alkane Hexane alkane Cyclopentane, methyl alkane Cyclohexane alkane Cyclohexane, methyl alkane Cyclopentane, ethyl alkane Octane alkane Cyclopentane, 1-ethyl-2- methyl alkane Cyclohexane, 1,2-dimethyl alkane Cyclohexane, 1,3-dimethyl-, trans alkane Cyclooctane alkane Cyclopentane, propyl alkane Cyclohexane, 1,2-dimethyl-, trans alkane Cyclohexane, ethyl alkane Octane, 3-methyl alkane Nonane alkane Cyclohexane, 1-ethyl-4- methyl-, cis alkane cis-1-ethyl-3-methylcyclohexane alkane Cyclohexane, (1- methylethyl) alkane Bicyclo[3.3.1]nonane alkane Cyclohexane, propyl alkane Cyclohexane, 1-ethyl-2- methyl-, cis alkane 1H-Indene, octahydro-, trans alkane Cyclohexane, 1-methyl-2- propyl alkane Decane alkane 1H-Indene, octahydro-, cis alkane Cyclohexane, 1,1-dimethyl alkane Cyclohexane, butyl alkane Naphthalene, decahydro-, trans alkane
7 Tentatively Identified Time (min) Benzene aromatic Toluene aromatic Ethylbenzene aromatic Benzene, 1,3-dimethyl aromatic Benzene, 1,2-dimethyl aromatic Benzene, propyl aromatic Benzene, 1-ethyl-2-methyl aromatic Indane aromatic Butanoic acid, methyl ester ester Butanoic acid, ethyl ester ester Acetic acid, butyl ester ester Pentanoic acid, methyl ester ester Butanoic acid, hexyl ester ester Acetic acid, pentyl ester ester Hexanoic acid, methyl ester ester 2H-Pyran, tetrahydro ether Furan, tetrahydro-2-methyl furan Furan, tetrahydro-2,5- dimethyl furan Furan, 2-butyltetrahydro furan 2-Pentanone ketone 3-Hexanone ketone 2-Hexanone ketone Cyclopentanone ketone Cyclopentanone, 2-methyl ketone Cyclopentanone, 3-methyl ketone Cyclopentanone, 2,5- dimethyl ketone Cyclopentanone, 2,3- dimethyl ketone Cyclohexanone ketone Cyclohexanone, 2-methyl ketone Cyclohexanone, 3-methyl ketone 3,7-Dimethyl-octa-1,6-diene olefin Cyclohexene, 1-butyl olefin Unidentified Peaks 14.0 undetermined
8 Table S-7: HT-138 Naphtha Tentatively Identified s by GC-MS Tentatively Identified Acetic acid acid 1-Butanol alcohol 1-Pentanol alcohol Cyclohexanol alcohol Octane alkane Cyclopentane, propyl alkane Cyclohexane, ethyl alkane Nonane alkane Cyclohexane, 1-ethyl-4- methyl-, cis alkane Cyclohexane, (1- methylethyl) alkane Bicyclo[3.3.1]nonane alkane Cyclohexane, propyl alkane 1H-Indene, octahydro-, trans alkane Cyclohexane, 1-methyl-2- propyl alkane Decane alkane Cyclohexane, 1-isopropyl-3- methyl-, (E) alkane 1H-Indene, octahydro-, cis alkane Cyclohexane, 1,1-dimethyl alkane Cyclohexane, butyl alkane Bicyclo[4.1.0]heptane, 3,7,7-trimethyl alkane Naphthalene, decahydro-, trans alkane Cyclopentane, butyl alkane Naphthalene, decahydro alkane trans-decalin, 2-methyl alkane Cyclohexane, pentyl alkane cis-decalin, 2-syn-methyl alkane Decalin, syn-1-methyl, cis alkane Dodecane alkane Toluene aromatic Ethylbenzene aromatic p-xylene aromatic Benzene, 1,2-dimethyl aromatic Benzene, propyl aromatic Benzene, 1-ethyl-2-methyl aromatic
9 Tentatively Identified Benzene, 1,2,4-trimethyl aromatic Benzene, 1,2,3-trimethyl aromatic Benzene, (1-methylpropyl) aromatic Indane aromatic Benzene, butyl aromatic 2,4-Dimethylstyrene aromatic 1-Phenyl-1-butene aromatic Benzene, (2-methyl-2- propenyl) aromatic 1H-Indene, 2,3-dihydro-4- methyl aromatic tetrahydro aromatic 1H-Indene, 2,3-dihydro-1,6- dimethyl aromatic n-propyl acetate ester Butanoic acid, methyl ester ester Butanoic acid, ethyl ester ester Acetic acid, butyl ester ester Pentanoic acid, methyl ester ester Butanoic acid, hexyl ester ester Pentanoic acid, ethyl ester ester Propanoic acid, butyl ester ester Acetic acid, pentyl ester ester Hexanoic acid, methyl ester ester Pentanoic acid, propyl ester ester 2-Hexanone ketone Cyclopentanone ketone Cyclopentanone, 2-methyl ketone Cyclopentanone, 3-methyl ketone Cyclopentanone, 2,5- dimethyl ketone Cyclopentanone, 2,4- dimethyl ketone Cyclohexanone ketone Cyclopentanone, 2-ethyl ketone 4-Octanone ketone Cyclohexanone, 2-methyl ketone Cyclohexanone, 3-methyl ketone Cyclohexanone, 4-methyl ketone 3,7-Dimethyl-octa-1,6-diene olefin Cyclohexene, 1-butyl olefin Phenol phenol Phenol, 2-methyl phenol Phenol, 3-methyl phenol
10 Tentatively Identified Unidentified Peaks 19.3 undetermined Table S-8: HT-138 Jet Tentatively Identified s by GC-MS Tentatively Identified Cyclohexanol alcohol 2,4-Pentadien-1-ol, 3- propyl-, (2Z) alcohol Cyclohexane, propyl alkane Cyclohexane, butyl alkane Naphthalene, decahydro-, trans alkane Cyclopentane, butyl alkane Naphthalene, decahydro-, cis alkane Cyclohexane, pentyl alkane Dodecane alkane Cyclopentylcyclohexane alkane Cyclohexane, (4- methylpentyl) alkane Cyclopentane, 1-methyl-3- (2-methylpropyl) alkane 1,1'-Bicyclohexyl alkane Benzene, propyl aromatic Benzene, 1-ethyl-2-methyl aromatic Benzene, 1-methyl-3- propyl aromatic Indane aromatic Benzene, butyl aromatic Benzene, 1-methyl-2- propyl aromatic 2,4-Dimethylstyrene aromatic 1-Phenyl-1-butene aromatic 1H-Indene, 2,3-dihydro-5- methyl aromatic tetrahydro aromatic 1H-Indene, 2,3-dihydro-1,6- dimethyl aromatic 1H-Indene, 2,3-dihydro-1,2- dimethyl aromatic 1H-Indene, 2,3-dihydro-1,3- dimethyl aromatic tetrahydro-2-methyl aromatic Benzene, (1-methyl-1- butenyl) aromatic
11 Tentatively Identified 1H-Indene, 2,3-dihydro-4,7- dimethyl aromatic tetrahydro-6-methyl aromatic Naphthalene, 5-ethyl- 1,2,3,4-tetrahydro aromatic tetrahydro-5-methyl aromatic Benzene, 1-(1- methylethenyl)-2-(1- methylethyl) aromatic Benzene, 1-(1- methylethenyl)-3-(1- methylethyl) aromatic Acenaphthylene, 1,2,2a,3,4,5-hexahydro aromatic tetrahydro-6,7-dimethyl aromatic Naphthalene, 2,7-dimethyl aromatic Benzene, (2- cyclohexylethyl) aromatic Pentanoic acid, propyl ester ester Benzene, 1-methoxy-4-(1- methylpropyl) ether Cyclopentanone, 2-methyl ketone Cyclohexanone ketone Cyclohexanone, 2-methyl ketone Cyclohexanone, 3-methyl ketone Cyclohexanone, 4-methyl ketone 1-(4-Hydroxymethylphenyl) ethanone ketone Phenol phenol Phenol, 2-methoxy phenol Phenol, 2-methyl phenol Phenol, 2,3-dimethyl phenol Phenol, 4-methyl phenol Phenol, 3-methyl phenol Phenol, 2-methoxy-4- methyl phenol Phenol, 2-ethyl phenol Phenol, 2,4-dimethyl phenol Phenol, 2-ethyl-6-methyl phenol Phenol, 2,4,6-trimethyl phenol Phenol, 3,5-dimethyl phenol Phenol, 4-ethyl phenol Phenol, 3-ethyl phenol Phenol, 3,4-dimethyl phenol
12 Tentatively Identified Phenol, 2-ethyl-4-methyl phenol Phenol, 2-ethyl-6-methyl phenol Phenol, 4-ethyl-2-methoxy phenol Phenol, 2-ethyl-5-methyl phenol Phenol, 2-ethyl-6-methyl phenol Phenol, 5-methyl-2-(1- methylethyl)-, acetate phenol Phenol, 3,4,5-trimethyl phenol Phenol, 4-propyl phenol 2-Methyl-6-propylphenol phenol Phenol, 4-(1-methylpropyl) phenol Phenol, 3,5-diethyl phenol Unidentified Peaks 30.9 undetermined
13 Table S-9: HT-138 Diesel Tentatively Identified s by GC-MS Tentatively Identified 1-Cyclohexene-1-methanol alcohol Benzenemethanol,.alpha.- propyl alcohol 2-Methyl-1-phenyl-1-pentanol alcohol Dodecane alkane Tridecane alkane Tetradecane alkane Hexadecane alkane tetrahydro aromatic Naphthalene,1,2,3,4-tetrahydro- 5-methyl aromatic Naphthalene, 5-ethyl-1,2,3,4- tetrahydro aromatic Acenaphthylene, 1,2,2a,3,4,5- hexahydro aromatic tetrahydro-1,5-dimethyl aromatic Bibenzyl aromatic Benzene, (2-cyclohexylethyl) aromatic Benzene, 1-pentynyl aromatic Benzene, [(tetramethylcyclopropylidene) methyl] aromatic Phenanthrene, 1,2,3,4,5,6,7,8- octahydro aromatic 1,2,3,4,5,6,7,8-Octahydro-1- methylphenanthrene aromatic 1,3-Benzodioxole, 5-propyl ether Ethanone, 1-(2-hydroxy-5- methylphenyl) ketone 1-Propanone, 1-(3- methoxyphenyl) ketone 2-Cyclohexen-1-one, 4-methyl- 4-phenyl ketone Phenol, 3-methyl phenol Phenol, 2,4-dimethyl phenol Phenol, 4-ethyl phenol Phenol, 2-ethyl phenol Phenol, 3-ethyl phenol Phenol, 3,4,5-trimethyl phenol Phenol, 4-ethyl-3-methyl phenol Phenol, 3-propyl phenol
14 Tentatively Identified Phenol, 2,4,5-trimethyl phenol Phenol, 3-(1-methylethyl) phenol Phenol, 2-ethyl-4,5-dimethyl phenol 2-Methyl-6-propylphenol phenol Phenol, 4-(1-methylpropyl) phenol Phenol, 4-ethyl-2-methoxy phenol Phenol, 3-methoxy-2-methyl phenol Unidentified Peaks 66.0 undetermined
15 Table S-10: HT-138 Gasoil Tentatively Identified s by GC-MS Tentatively Identified 6-Chrysenol alcohol Cyclohexane, decyl alkane Pyrene, 4-methyl aromatic 1,2,3,4-Tetrahydro-1- phenyl-1,2,3- methanonaphthalene aromatic Pyrene, 1-methyl aromatic 1,4-dimethyl-2-phenyl- Naphthalene aromatic 8,9,10,11- Tetrahydrobenz[A]anthrace ne aromatic Benzo[c]phenanthrene, 1- methyl aromatic Benzo[c]phenanthrene, 5,8- dimethyl aromatic Chrysene, 5-ethyl aromatic 7,8,9,10,11,12- Hexahydrobenzo[A]pyrene aromatic Z,Z-4,16-Octadecadien-1-ol acetate ester 9,10-Anthracenedione, 2- methyl ketone 9,10-Anthracenedione, 2,3- dimethyl ketone Unidentified Peaks 79.0 undetermined
16 Table S-11: HT-109 Lights Tentatively Identified s by GC-MS Tentatively Identified Butane alkane Butane, 2-methyl alkane Pentane alkane Pentane, 2-methyl alkane Pentane, 3-methyl alkane Hexane alkane Cyclopentane, methyl alkane Hexane, 2-methyl alkane Cyclohexane alkane Cyclohexane, methyl alkane Cyclopentane, ethyl alkane Hexane, 2,3-dimethyl alkane Heptane, 3-methyl alkane Cyclopentane, 1,2,4- trimethyl alkane Cyclohexane, 1,4-dimethyl alkane Cyclopentane, 1-ethyl-3- methyl alkane Cyclopentane, 1-ethyl-2- methyl alkane Cyclohexane, 1,3-dimethyl-, trans alkane Cyclooctane alkane Cyclopentane, propyl alkane Cyclohexane, ethyl alkane Cyclopentane, 2-ethylidene- 1,1-dimethyl alkane Octane, 4-methyl alkane Octane, 3-methyl alkane Nonane alkane Cyclohexane, 1-ethyl-2- methyl alkane Octane, 3-methyl alkane Benzene aromatic Toluene aromatic Ethylbenzene aromatic Benzene, 1,3-dimethyl aromatic Benzene, 1,2-dimethyl aromatic Benzene, propyl aromatic 3-Hexene, (E) olefin Cyclopentene, 3-methyl olefin
17 Tentatively Identified Cyclopentene, 4-methyl olefin 2-Hexene, 2-methyl olefin Cyclopentene, 1,5-dimethyl olefin Cyclohexene, 4-methyl olefin Cyclopentene, 1-ethyl olefin Cyclohexene, 1-methyl olefin Cyclopentene, 1,2,3- trimethyl olefin 2-Ethyl-3- methylcyclopentene olefin Cyclohexene, 1-ethyl olefin 1-Methyl-2- methylenecyclohexane olefin 3-Octyne, 2-methyl olefin Cyclohexene, 4-propyl olefin Phenol phenol Unidentified Peaks 13.7 undetermined
18 Table S-12: HT-109 Naphtha Tentatively Identified s by GC-MS Tentatively Identified Hexane alkane Cyclopentane, methyl alkane Cyclohexane alkane Cyclohexane, methyl alkane Cyclopentane, ethyl alkane Cyclopentane,1-ethyl-3- methyl alkane Cyclopentane, 1-ethyl-2- methyl alkane Cyclohexane, 1,4-dimethyl alkane Cyclooctane alkane Cyclopentane, propyl alkane Cyclohexane, ethyl alkane Octane, 4-methyl alkane Octane, 3-methyl alkane Nonane alkane Cyclohexane, 1-ethyl-2- methyl alkane Cyclohexane, propyl alkane Octane, 4-ethyl alkane Nonane, 3-methyl alkane Cyclopentane, (2- methylbutyl) alkane Cyclooctane, 1,2-dimethyl alkane Decane alkane Cyclopentane, pentyl alkane Bicycloheptane, 3,7,7- trimethyl alkane Spiro[4.5]decane alkane 1-Methyldecahydro- Naphthalene alkane Cyclohexane, pentyl alkane Benzene aromatic Toluene aromatic Ethylbenzene aromatic Benzene, 1,3-dimethyl aromatic Benzene, 1,2-dimethyl aromatic Benzene, propyl aromatic 1H-Indene, octahydro-, cis aromatic Benzene, 1-ethyl-2-methyl aromatic
19 Tentatively Identified 1H-Indene, 2,3,4,5,6,7- hexahydro aromatic Benzene, 1,2,4-trimethyl aromatic Benzene, 1,2,3-trimethyl aromatic Benzene, (1-methylpropyl) aromatic Benzene, 1-ethenyl-2- methyl aromatic Benzene, butyl aromatic Benzene, 1-methyl-2- propyl aromatic Naphthalene, decahydro-2- methyl aromatic Benzene, 1-ethyl-2,4- dimethyl aromatic 2,4-Dimethylstyrene aromatic 1-Phenyl-1-butene aromatic 1H-Indene, 2,3-dihydro-5- methyl aromatic 3-Phenylbut-1-ene aromatic tetrahydro aromatic Cyclopentene, 4-methyl olefin Cyclohexene, 1-methyl olefin Cyclopentnene, 1,5- dimethyl olefin Cyclopentene, 1-ethyl olefin Cyclohexene, 1-methyl olefin Cyclohexane, ethenyl olefin Cyclooctene, 3-methyl olefin Cyclohexene, 3-(2- methylpropyl) olefin Cyclohexene, 1-butyl olefin Cyclohexene, 4-methyl-1- (1-methylethyl) olefin Cyclododecene, 1-methyl olefin Phenol phenol Phenol, 2-methyl phenol Phenol, 2,6-dimethyl phenol Phenol, 4-methyl phenol Phenol, 3-methyl phenol Phenol, 2-ethyl phenol Phenol, 2,4-dimethyl phenol Phenol, 3-ethyl phenol Phenol, 3-propyl phenol Unidentified Peaks 32.4 undetermined
20 Table S-13: HT-109 Jet Tentatively Identified s by GC-MS Tentatively Identified 6-Methyl-4-indanol alcohol 1H-Inden-5-ol, 2,3-dihydro alcohol Propanal, 2-methyl-3- phenyl aldehyde Dodecane alkane 2,4-Dimethylstyrene aromatic tetrahydro aromatic 1H-Indene, 2,3-dihydro-1,3- dimethyl aromatic 1H-Indene, 2,3-dihydro-1,2- dimethyl aromatic 1H-Indene, 2,3-dihydro-2,2- dimethyl aromatic tetrahydro-2-methyl aromatic 2-Ethyl-2,3-dihydro-1Hindene aromatic Octane, 3-methyl aromatic Benzene, (1-methyl-1- butenyl) aromatic Naphthalene, 6-ethyl- 1,2,3,4-tetrahydro aromatic tetrahydro-6-methyl aromatic tetrahydro-1,8-dimethyl aromatic 1H-Indene, 2,3-dihydro- 1,1,3-trimethyl aromatic Naphthalene, 2-ethyl- 1,2,3,4-tetrahydro aromatic Naphthalene, 1-methyl aromatic tetrahydro-5,7-dimethyl aromatic Naphthalene, 1,6-dimethyl aromatic Naphthalene, 1,3-dimethyl aromatic Naphthalene, 2,7-dimethyl aromatic Naphthalene, 2,3-dimethyl aromatic Naphthalene, 1,2-dimethyl aromatic Naphthalene, 1,6,7- trimethyl aromatic Benzene, hexamethyl aromatic Naphthalene, 1,4,6- trimethyl aromatic
21 Tentatively Identified Benzene, 1,2-diethyl-3,4- dimethyl aromatic 1,1'-Biphenyl, 2-methyl aromatic Benzene, 1-ethoxy-4-ethyl ether Benzene, 1-methoxy-4-(1- methylpropyl) ether 1,3-Benzodioxole, 5-propyl ether Benzene, 2-methoxy-4- methyl-1-(1-methylethyl) ether Benzene, 1-methoxy-4-(1- methylethyl) ether Ethanone, 1-(2,5- dimethylphenyl) ketone 4-Hydroxy-3- methylacetophenone ketone Ethanone, 1-(4- ethylphenyl) ketone 1,3-Cyclopentadiene, 5,5- dimethyl-2-propyl olefin 6-tert-Butyl-2,4- dimethylphenol phenol Phenol phenol Phenol, 2-methyl phenol Phenol, 2,6-dimethyl phenol Phenol, 4-methyl phenol Phenol, 3-methyl phenol Phenol, 2-ethyl phenol Phenol, 2,4-dimethyl phenol Phenol, 2-(1-methylethyl) phenol Phenol, 2,4,6-trimethyl phenol Phenol, 3,5-dimethyl phenol Phenol, 4-ethyl phenol Phenol, 3-ethyl phenol Phenol, 2,3,6-trimethyl phenol Phenol, 2,3,5-trimethyl phenol Phenol, 4-(1-methylpropyl) phenol Phenol, 2-ethyl-5-methyl phenol Phenol, 2-ethyl-6-methyl phenol Phenol, 3-(1-methylethyl) phenol Phenol, 2-methyl-5-(1- methylethyl) phenol Phenol, 3,4,5-trimethyl phenol Phenol, 3,4,5-trimethyl phenol Phenol, 3-ethyl-5-methyl phenol 2-Methyl-6-propylphenol phenol 3,4-Diethylphenol phenol
22 Tentatively Identified Phenol, 2-(1-methylpropyl) phenol 2-Methyl-6-propylphenol phenol Phenol, 2-ethyl-4,5- dimethyl phenol Phenol, diethyl phenol Phenol, 3,5-diethyl phenol 2-Ethyl-5-n-propylphenol phenol Phenol, 2-pentyl phenol Phenol, 3-propyl phenol Unidentified Peaks 16.1 undetermined
23 Table S-14: HT-109 Diesel Tentatively Identified s by GC-MS Tentatively Identified 5,8,11,14-Eicosatetraynoic acid acid Benzenebutanal, 2-methoxygamma, 4-dimethyl aldehyde Tridecane alkane Tetradecane alkane Hexadecane alkane Benzene, 1,2-diethyl-2,3- dimethyl aromatic Benzene, 1,2,4-triethyl-5- methyl aromatic Naphthalene, 1,4,6- trimethyl aromatic Benzene, ethylpentamethyl aromatic Benzene, ethylpentamethyl aromatic 1,1'-Biphenyl, 2-methyl aromatic Octane, 3-methyl aromatic 3,3'- Dimethylbiphenyl aromatic 1,1'-Biphenyl-3,4'-dimethyl aromatic 4,4'-Dimethylbiphenyl aromatic Phenanthrene, 1,2,3,4- tetrahydro aromatic Isopropylbiphenyl aromatic Phenanthrene aromatic Tricyclooct-3-ene, exo-6- methyl-7-phenyl aromatic Benzene, 1-methyl-3-[(4- methylphenyl)methyl] aromatic Phenanthrene, 9-methyl aromatic 1,1'-Biphenyl, 3,4-diethyl aromatic Benzene, 1-(1-butenyl)-4- methoxy-, trans ether Benzene, 1-ethyl-4- methoxy ether 1-Propanone, 1-(2,4- dimethylphenyl) ketone 1-(2,3,4,5- Tetramethylphenyl)ethanone ketone 2,2-Dimethyl-1- acenaphthenone ketone Unidentified Peaks 71.3 undetermined
24 Table S-15: HT-109 Gasoil Tentatively Identified s by GC-MS Tentatively Identified Nonadecane alkane Eicosane alkane Heptadecane, 2,6,10,15- tetramethyl alkane Pentacosane alkane Heptacosane alkane Pyrene, 4-methyl aromatic 4b,5,6,12- Tetrahydrochrysene aromatic 1,4-dimethyl-2-phenyl- Naphthalene aromatic Benzo[c]phenanthrene, 1- methyl aromatic Chrysene, 5-ethyl aromatic Unidentified Peaks 90.3 undetermined
25 Table S-16: HT-140 Lights Tentatively Identified s by GC-MS Tentatively Identified Pentane alkane Cyclopentane alkane Hexane alkane Cyclopentane, methyl alkane Hexane, 2-methyl alkane Cyclohexane alkane Cyclohexane, methyl alkane Cyclopentane, ethyl alkane Heptane, 2-methyl alkane Heptane, 4-methyl alkane Heptane, 3-methyl alkane Cyclohexane, 1,2-dimethyl alkane Octane alkane Cyclopentane, 1-ethyl-2- methyl alkane Cyclohexane, 1,4-dimethyl alkane Cyclopentane, propyl alkane Cyclohexane, ethyl alkane Heptane, 2,4-dimethyl alkane Nonane alkane Cyclohexane, propyl alkane Benzene aromatic Toluene aromatic Ethylbenzene aromatic Benzene, 1,3-dimethyl aromatic Benzene, propyl aromatic Unidentified Peaks 6.3 undetermined
26 Table S-17: HT-140 Naphtha Tentatively Identified s by GC-MS Tentatively Identified Hexane alkane Cyclopentane, methyl alkane Hexane, 2-methyl alkane Cyclohexane alkane Cyclohexane, methyl alkane Cyclopentane, ethyl alkane Heptane, 2-methyl alkane Heptane, 4-methyl alkane Heptane, 3-methyl alkane Hexane, 3-ethyl alkane Cyclohexane, 1,2-dimethyl alkane Hexane, 2,4-dimethyl alkane Cyclopentane, 1-ethyl-2- methyl alkane Cyclohexane, 1,2-dimethyl-, trans alkane Cyclohexane, 1,4-dimethyl alkane Cyclopentane, 1-ethyl-2- methyl-, cis alkane Cyclopentane, propyl alkane Cyclohexane, ethyl alkane Heptane, 2,4-dimethyl alkane Octane, 3-methyl alkane Cyclopentane, 1-methyl-2- propyl alkane Nonane alkane Cyclohexane, 1-ethyl-4- methyl-, trans alkane Cyclohexane, (1- methylethyl) alkane Cyclohexane, propyl alkane Nonane, 3-methyl alkane 1H-Indene, octahydro-, trans alkane Cyclohexane, 1-methyl-2- propyl alkane Decane alkane 1H-Indene, octahydro-, cis alkane Cyclohexane, butyl alkane Benzene aromatic Toluene aromatic Ethylbenzene aromatic
27 Tentatively Identified Benzene, 1,3-dimethyl aromatic Benzene, 1,2-dimethyl aromatic Benzene, propyl aromatic Benzene, 1-ethyl-2-methyl aromatic Indane aromatic Unidentified Peaks 9.1 undetermined
28 Table S-18: HT-140 Jet Tentatively Identified s by GC-MS Tentatively Identified Cyclohexane, methyl alkane Octane alkane Cyclopentane, propyl alkane Cyclohexane, ethyl alkane Nonane alkane Cyclohexane, 1-ethyl-4- methyl-, trans alkane Cyclohexane, propyl alkane Nonane, 3-methyl alkane 1H-Indene, octahydro-, trans alkane Cyclohexane, 1-methyl-2- propyl alkane Decane alkane 1H-Indene, octahydro-, cis alkane Cyclohexane, butyl alkane Naphthalene, decahydro-, trans alkane Undecane alkane Cyclooctane, butyl alkane Naphthalene, decahydro alkane trans-decalin, 2-methyl alkane Cyclohexane, pentyl alkane Dodecane alkane Cyclopentylcyclohexane alkane Cyclohexane, hexyl alkane 1,1'-Bicyclohexyl alkane Heptylcyclohexane alkane Cyclohexane, 1,1'-(1,2- ethanediyl)bis alkane Toluene aromatic Ethylbenzene aromatic Benzene, 1,3-dimethyl aromatic Benzene, 1,2-dimethyl aromatic Benzene, propyl aromatic Benzene, 1-ethyl-2-methyl aromatic Benzene, 1,2,3-trimethyl aromatic Benzene, 1-methyl-3- propyl aromatic Indane aromatic Benzene, butyl aromatic
29 Tentatively Identified Benzene, 1-methyl-2- propyl aromatic 1-Phenyl-1-butene aromatic Benzene, 1-methyl-4-(1- methylpropyl) aromatic Benzene, 4-ethyl-1,2- dimethyl aromatic Benzene, (2-methyl-1- butenyl) aromatic 1H-Indene, 2,3-dihydro-5- methyl aromatic Benzene, pentyl aromatic 1H-Indene, 2,3-dihydro-4- methyl aromatic tetrahydro aromatic 1H-Indene, 2,3-dihydro-1,6- dimethyl aromatic 1H-Indene, 2,3-dihydro-1,3- dimethyl aromatic Naphthalene, 1-ethyl- 1,2,3,4-tetrahydro aromatic tetrahydro-2-methyl aromatic tetrahydro-1-methyl aromatic 2-Ethyl-2,3-dihydro-1Hindene aromatic Benzene, hexyl aromatic tetrahydro-6-methyl aromatic Naphthalene, 5-ethyl- 1,2,3,4-tetrahydro aromatic tetrahydro-5-methyl aromatic tetrahydro-1,4-dimethyl aromatic Benzene, 1-(1- methylethenyl)-3-(1- methylethyl) aromatic tetrahydro-1,5-dimethyl aromatic Naphthalene, 2-ethyl- 1,2,3,4-tetrahydro aromatic Naphthalene, 2-methyl aromatic tetrahydro-1,8-dimethyl aromatic tetrahydro-6,7-dimethyl aromatic (1,4-Dimethylpent-2- enyl)benzene aromatic
30 Tentatively Identified Benzene, (2- cyclohexylethyl) aromatic Cyclohexene, 1-butyl olefin Phenol, 2-methyl phenol Phenol, 2-ethyl-6-methyl phenol Phenol, 2-ethyl-6-methyl phenol Unidentified Peaks 26.0 undetermined
31 Table S-19: HT-140 Diesel Tentatively Identified s by GC-MS Tentatively Identified Hexadecane alkane Cyclohexane, 1,1'- methylenebis alkane Cyclohexane, 1,1'-(1,2- ethanediyl)bis alkane Tetradecane alkane Cyclohexane, 1,1'-(1,3- propanediyl)bis alkane Tridecane alkane Heptylcyclohexane alkane Benzene, 1,2-bis(1-buten-3- yl) aromatic Phenanthrene, 1,2,3,4,5,6,7,8-octahydro aromatic Bi-1,3,5-cycloheptatrien-1- yl aromatic Phenanthrene, 1,2,3,4- tetrahydro aromatic Anthracene, 9-ethenyl aromatic Benzene, 1-pentynyl aromatic Benzene, (3- cyclopentylpropyl) aromatic Pyrene, 1,2,3a,4,5- hexahydro aromatic Fluoranthene aromatic 1,4,9-Decatriene, 1-phenyl-, (E,E) aromatic Phenanthrene, 9,10-dihydro- 1-methyl aromatic Benzene, 1-cyclopenten-1- yl aromatic 5,6,7,8-Tetrahydro-1-phenyl Naphthalene aromatic Cyclohexane, 2-propenyl olefin 1,4-Cyclohexadiene, 3- ethenyl-1,2-dimethyl olefin Unidentified Peaks 76.5 undetermined
32 Table S-20: HT-140 Gasoil Tentatively Identified s by GC-MS Tentatively Identified Hexadecane alkane Docosane alkane Eicosane alkane Heneicosane alkane Heptadecane, 2,6,10,15- tetramethyl alkane Tetracosane alkane 1,4,9-Decatriene, 1-phenyl-, (E,E) aromatic Phenanthrene, 1,2,3,4,5,6,7,8-octahydro aromatic Fluoranthene aromatic Pyrene, 4-methyl aromatic Benzo[c]phenanthrene, 1- methyl aromatic Unidentified Peaks 86.7 undetermined
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