Charles S. McEnally* and Lisa D. Pfefferle. Department of Chemical Engineering and Center for Combustion Studies, Yale University, New Haven
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1 Supporting Information for Sooting tendencies of oxygenated hydrocarbons in laboratory-scale flames Charles S. McEnally* and Lisa D. Pfefferle Department of Chemical Engineering and Center for Combustion Studies, Yale University, New Haven CT * phone: , fax: Supporting Information Summary Number of Pages: 17 Number of Figures: 1 Number of Tables: 2 1
2 Figure S1. Diagram showing the experimental apparatus. Table S1. Yield Sooting Indices measured for regular and oxygenated hydrocarbons and scaled such that YSI(n-hexane) = 0.0 and YSI(benzene) = Name (synonym) Formula CAS # a YSI b Linear Alkanes n-pentane C 5 H n-hexane C 6 H c 2-methylpentane C 6 H methylpentane C 6 H ,2-dimethylbutane C 6 H
3 2,3-dimethylbutane C 6 H n-heptane C 7 H methylhexane C 7 H methylhexane C 7 H ,2-dimethylpentane C 7 H ,3-dimethylpentane C 7 H ,4-dimethylpentane C 7 H ,3-dimethylpentane C 7 H ,2,3-trimethylbutane C 7 H n-octane C 8 H methylheptane C 8 H methylheptane C 8 H methylheptane C 8 H ,2-dimethylhexane C 8 H ,4-dimethylhexane C 8 H ,5-dimethylhexane C 8 H ,4-dimethylhexane C 8 H ,2,4-trimethylpentane (isooctane) C 8 H ,3,4-trimethylpentane C 8 H n-nonane C 9 H ,3-dimethylheptane C 9 H n-decane C 10 H n-undecane C 11 H n-dodecane C 12 H ,2,4,6,6-pentamethylheptane (isododecane) C 12 H Cyclic Alkanes cyclopentane C 5 H cyclohexane C 6 H
4 methylcyclopentane C 6 H cycloheptane C 7 H methylcyclohexane C 7 H ethylcyclopentane C 7 H cyclooctane C 8 H ethylcyclohexane C 8 H ,1-dimethylcyclohexane C 8 H cis 1,2-dimethylcyclohexane C 8 H ,3-dimethylcyclohexane d C 8 H ,4-dimethylcyclohexane C 8 H propylcyclohexane C 9 H isopropylcyclohexane C 9 H ,2,4-trimethylcyclohexane C 9 H butylcyclohexane C 10 H Alkenes cis 2-pentene C 5 H methyl-2-butene C 5 H hexene C 6 H cis 2-hexene C 6 H trans 2-hexene C 6 H trans 3-hexene C 6 H methyl-1-pentene C 6 H methyl-1-pentene C 6 H methyl-1-pentene C 6 H methyl-2-pentene C 6 H methyl-2-pentene C 6 H cis 4-methyl-2-pentene C 6 H ethyl-1-butene C 6 H
5 2,3-dimethyl-1-butene C 6 H ,3-dimethyl-2-butene C 6 H ,3-dimethyl-1-butene C 6 H heptene C 7 H cis 2-heptene C 7 H trans 3-heptene C 7 H methyl-1-hexene C 7 H methyl-1-hexene C 7 H ethyl-2-pentene C 7 H ,4-dimethyl-1-pentene C 7 H ,3,3-trimethyl-1-butene C 7 H octene C 8 H trans 2-octene C 8 H trans 3-octene C 8 H trans 4-octene C 8 H methyl-1-heptene C 8 H methyl-2-heptene C 8 H ,3,4-trimethyl-2-pentene C 8 H ,4,4-trimethyl-1-pentene C 8 H ,4,4-trimethyl-2-pentene C 8 H nonene C 9 H decene C 10 H dodecene C 12 H Cyclic Alkenes cyclopentene C 5 H cyclohexene C 6 H methylcyclopentene C 6 H cycloheptene C 7 H
6 Alkynes and Alkadienes 1-pentyne C 5 H pentyne C 5 H methyl-1,5-hexadiene C 7 H octyne C 8 H Alcohols methanol CH 4 O ethanol C 2 H 6 O propanol C 3 H 8 O propanol C 3 H 8 O butanol C 4 H 10 O butanol C 4 H 10 O (R)-2-butanol C 4 H 10 O (S)-2-butanol C 4 H 10 O methyl-1-propanol C 4 H 10 O tert-butanol C 4 H 10 O pentanol C 5 H 12 O pentanol C 5 H 12 O pentanol C 5 H 12 O methyl-1-butanol C 5 H 12 O methyl-2-butanol C 5 H 12 O
7 3-methyl-1-butanol C 5 H 12 O methyl-2-butanol C 5 H 12 O hexanol C 6 H 14 O hexanol C 6 H 14 O hexanol C 6 H 14 O methyl-1-pentanol C 6 H 14 O methyl-2-pentanol C 6 H 14 O methyl-1-pentanol C 6 H 14 O methyl-2-pentanol C 6 H 14 O methyl-1-pentanol C 6 H 14 O methyl-2-pentanol C 6 H 14 O ethyl-1-butanol C 6 H 14 O ,3-dimethyl-2-butanol C 6 H 14 O ,3-dimethyl-1-butanol C 6 H 14 O ,3-dimethyl-2-butanol C 6 H 14 O cyclohexanol C 6 H 12 O heptanol C 7 H 16 O heptanol C 7 H 16 O heptanol C 7 H 16 O
8 heptanol C 7 H 16 O methyl-2-hexanol C 7 H 16 O methyl-2-hexanol C 7 H 16 O ethyl-3-pentanol C 7 H 16 O ,2-dimethyl-3-pentanol C 7 H 16 O ,4-dimethyl-3-pentanol C 7 H 16 O octanol C 8 H 18 O octanol C 8 H 18 O octanol C 8 H 18 O octanol C 8 H 18 O ethyl-1-hexanol C 8 H 18 O propyl-1-pentanol C 8 H 18 O ,4,4-trimethyl-1-pentanol C 8 H 18 O Ethers methyl propyl ether C 4 H 10 O diethyl ether C 4 H 10 O methyl butyl ether C 5 H 12 O methyl sec-butyl ether C 5 H 12 O
9 -2.8 methyl tert-butyl ether C 5 H 12 O dipropyl ether C 6 H 14 O diisopropyl ether C 6 H 14 O methyl tert-amyl ether C 6 H 14 O tert-butyl ethyl ether C 6 H 14 O methyl cyclopentyl ether C 6 H 12 O dibutyl ether C 8 H 18 O sec-butyl ether C 8 H 18 O isoamyl ether C 10 H 22 O Alkanones 2-propanone (acetone) C 3 H 6 O butanone C 4 H 8 O pentanone C 5 H 10 O pentanone C 5 H 10 O methyl-2-butanone C 5 H 10 O hexanone C 6 H 12 O hexanone C 6 H 12 O methyl-3-pentanone C 6 H 12 O methyl-2-pentanone C 6 H 12 O
10 4-methyl-2-pentanone C 6 H 12 O ,3-dimethyl-2-butanone C 6 H 12 O cyclohexanone C 6 H 10 O heptanone C 7 H 14 O heptanone C 7 H 14 O heptanone C 7 H 14 O methyl-3-hexanone C 7 H 14 O ,4-dimethyl-3-pentanone C 7 H 14 O ,4-dimethyl-2-pentanone C 7 H 14 O octanone C 8 H 16 O octanone C 8 H 16 O methyl-3-heptanone C 8 H 16 O nonanone C 9 H 18 O nonanone C 9 H 18 O nonanone C 9 H 18 O ,6-dimethyl-4-heptanone C 9 H 18 O ,2,4,4-tetramethyl-3-pentanone C 9 H 18 O decanone C 10 H 20 O decanone C 10 H 20 O
11 Aldehydes propanal (propionaldehyde) C 3 H 6 O butanal C 4 H 8 O isobutanal C 4 H 8 O pentanal C 5 H 10 O methylbutanal C 5 H 10 O methylbutanal C 5 H 10 O ,2-dimethylpropanal C 5 H 10 O hexanal C 6 H 12 O methylpentanal C 6 H 12 O ethylbutanal C 6 H 12 O ,3-dimethylbutanal C 6 H 12 O heptanal C 7 H 14 O octanal C 8 H 16 O ethylhexanal C 8 H 16 O nonanal C 9 H 18 O ,5,5-trimethylhexanal C 9 H 18 O decanal C 10 H 20 O butylhexanal C 10 H 20 O Cyclic Ethers 11
12 1,3-dioxolane C 3 H 6 O tetrahydrofuran (oxolane) C 4 H 8 O ,2-epoxybutane C 4 H 8 O tetrahydropyran (oxane) C 5 H 10 O methoxytetrahydropyran C 6 H 12 O Esters and Carboxylic Acids ethyl formate C 3 H 6 O methyl acetate C 3 H 6 O propyl formate C 4 H 8 O isopropyl formate C 4 H 8 O ethyl acetate C 4 H 8 O methyl propionate C 4 H 8 O butyric acid C 4 H 8 O isobutyric acid C 4 H 8 O butyl formate C 5 H 10 O isobutyl formate C 5 H 10 O tert-butyl formate C 5 H 10 O propyl acetate C 5 H 10 O isopropyl acetate C 5 H 10 O ethyl propionate C 5 H 10 O methyl butyrate C 5 H 10 O methyl isobutyrate C 5 H 10 O
13 pentyl formate (amyl formate) C 6 H 12 O isopentyl formate (isoamyl formate) C 6 H 12 O butyl acetate C 6 H 12 O isobutyl acetate C 6 H 12 O sec-butyl acetate C 6 H 12 O tert-butyl acetate C 6 H 12 O propyl propionate C 6 H 12 O ethyl butyrate C 6 H 12 O ethyl isobutyrate C 6 H 12 O methyl pentanoate (methyl valerate) C 6 H 12 O methyl isopentanoate (methyl isovalerate) C 6 H 12 O methyl 2-methylbutyrate C 6 H 12 O methyl trimethylacetate C 6 H 12 O ethylbutyric acid C 6 H 12 O ,2-dimethylbutyric acid C 6 H 12 O pentyl acetate C 7 H 14 O isopentyl acetate C 7 H 14 O butyl propionate C 7 H 14 O isobutyl propionate C 7 H 14 O tert-butyl propionate C 7 H 14 O propyl butyrate C 7 H 14 O isopropyl butyrate C 7 H 14 O ethyl pentanoate (ethyl valerate) C 7 H 14 O ethyl isopentanoate (ethyl isovalerate ) C 7 H 14 O ethyl 2-methylbutyrate C 7 H 14 O methyl hexanoate C 7 H 14 O methyl heptanoate C 8 H 16 O methyl octanoate C 9 H 18 O
14 Other Multi-Oxygen Compounds 1,2-ethanediol (ethylene glycol) C 2 H 6 O ,2-propanediol C 3 H 8 O dimethyl carbonate C 3 H 6 O dimethoxymethane (formaldehyde dimethyl acetal) C 3 H 8 O ,1-dimethoxyethane (acetaldehyde dimethyl acetal) C 4 H 10 O ,2-dimethoxyethane C 4 H 10 O methoxy-2-propanol C 4 H 10 O methoxy-1-propanol C 4 H 10 O ethoxyethanol C 4 H 10 O trimethoxymethane C 4 H 10 O hydroxy-methylpropionate C 4 H 8 O ,2-dimethoxypropane C 5 H 12 O methoxy-2-butanol C 5 H 12 O ,2-dimethoxypropane C 5 H 12 O isopropoxyethanol C 5 H 12 O diethoxymethane C 5 H 12 O (2-methoxyethoxy)-ethanol (diethylene glycol methyl ether) C 5 H 12 O ,1,1-trimethoxyethane C 5 H 12 O diethyl carbonate C 5 H 10 O ,1-dimethoxy-2-propanone C 5 H 10 O tetramethoxymethane (tetramethylorthocarbonate) C 5 H 12 O butoxyethanol C 6 H 14 O methoxy-2-(2-methoxyethoxy)ethane (diglyme) C 6 H 14 O ,1-diethoxyethane (acetal) C 6 H 14 O methoxy-3-methyl-1-butanol C 6 H 14 O
15 1-propoxy-2-propanol (propylene glycol propyl ether) C 6 H 14 O ,2-diethoxyethane (ethylene glycol diethyl ether) C 6 H 14 O butoxy-2-propanol (propylene glycol butyl ether) C 7 H 16 O tert-butoxy-2-propanol C 7 H 16 O ,1-diethoxypropane (propionaldehyde diethyl acetal) C 7 H 16 O dipropyl carbonate C 7 H 14 O a molecular identifier assigned by the American Chemical Society b uncertainty = ±2 c YSI = 0.0 by definition d test compounds are mixtures of geometric isomers, unless a specific isomer is listed Table S2. Maximum carbon mass in aromatic species (M c ) calculated for the test flames using the method of Reference 11. Name YSI M C (mg/mole) Linear Alkanes n-pentane n-hexane methylpentane methylpentane ,3-dimethylbutane n-heptane methylhexane methylhexane ,3-dimethylpentane
16 2,4-dimethylpentane n-octane methylheptane methylheptane methylheptane ,4-dimethylhexane ,5-dimethylhexane ,4-dimethylhexane ,3,4-trimethylpentane n-nonane ,3-dimethylheptane n-decane n-undecane n-dodecane Alcohols methanol ethanol propanol propanol butanol butanol methyl-1-propanol tert-butanol pentanol pentanol pentanol methyl-1-butanol methyl-2-butanol
17 3-methyl-1-butanol methyl-2-butanol hexanol hexanol hexanol methyl-1-pentanol methyl-1-pentanol methyl-1-pentanol ethyl-1-butanol methyl-2-pentanol methyl-2-pentanol methyl-2-pentanol ,3-dimethyl-2-butanol heptanol heptanol heptanol heptanol methyl-2-hexanol ethyl-3-pentanol methyl-2-hexanol ,4-dimethyl-3-pentanol octanol octanol octanol octanol ethyl-1-hexanol propyl-1-pentanol Ethers 17
18 methyl propyl ether diethyl ether methyl butyl ether methyl sec-butyl ether methyl tert-butyl ether dipropyl ether diisopropyl ether methyl tert-amyl ether ethyl tert-butyl ether dibutyl ether sec-butyl ether isoamyl ether Center Esters propyl acetate butyl acetate propyl propionate pentyl acetate isopentyl acetate butyl propionate propyl butyrate Non-6-Center Esters and Carboxylic Acids methyl acetate ethyl acetate methyl propionate isopropyl acetate ethyl propionate methyl butyrate
19 methyl isobutyrate isobutyl acetate ethyl butyrate ethyl isobutyrate methyl pentanoate methyl isopentanoate isobutyl propionate tert-butyl propionate isopropyl butyrate ethyl pentanoate ethyl isopentanoate ethyl 2methylbutyrate methyl hexanoate methyl heptanoate methyl octanoate Other Multi-Oxygen Compounds 1,2-ethanediol ,2-propanediol ,2-dimethoxyethane methoxy-2-propanol methoxy-1-propanol ethoxyethanol methoxy-2-butanol ,2-dimethoxypropane isopropoxyethanol (2-methoxyethoxy)-ethanol butoxyethanol methoxy-2-(2-methoxyethoxy)ethane
20 3-methoxy-3-methyl-1-butanol propoxy-2-propanol ,2-diethoxyethane butoxy-2-propanol tert-butoxy-2-propanol
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