Experimental investigation of the low temperature oxidation of the five isomers of hexane
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1 Experimental investigation of the low temperature oxidation of the five isomers of hexane Zhandong WANG 1,, Olivier HERBINET 1, Zhanjun Cheng, Benoit HUSSON 1, René Fournet 1, Fei QI, Frédérique BATTIN-LECLERC 1 1 Laboratoire Réactions et Génie des Procédés, Nancy Université, CNRS UPR 339, BP 51, 1 rue Grandville, 5 Nancy, France National Synchrotron Radiation Laboratory, University of Science and Technology of China, Hefei, Anhui 39, P. R. China. Supplemental data I. Comparison of GC and SVUV PIMS data for n-hexane, -methyl-pentane and,-dimethyl-butane. II. Mass spectra of cyclic ethers which were not in databases. III. Structures of the parent cations obtained from the ionization of ketohydroperoxydes and diones.
2 I. Comparison of GC and SVUV PIMS data for n-hexane, -methyl-pentane and,- dimethyl-butane. 1. Comparison for n-hexane 5x n-hexane 8 Oxygen 8 Figure S1: Comparison of mole fraction profiles obtained using gas chromatography () and SVUV-PIMS ( ) for n-hexane and oxygen (fuel inlet mole fraction of.). The signals recorded at 11 ev for m/z 86 and at 16.6 ev for m/z 3 were used for the quantification of n-hexane and oxygen, respectively.
3 5x Carbon Monoxide from the signal at 16.6 ev for m/z 8) 1x Carbon Dioxide from the signal at 16.6 ev for m/z ) x Methanol from the signal at 11 ev for m/z 3) 1x Acetaldehyde from the signal at 1.5 ev for m/z ) x Acetic Acid from the signal at 11 ev for m/z 6) 8x1-6 6 Propanoic Acid from the signal at 11 ev for m/z 7) Figure S: Comparison of mole fraction profiles obtained using gas chromatography () and SVUV-PIMS ( ) for oxygenated reaction products (fuel inlet mole fraction of.).
4 1.x x Methane from the signal at 16.6 ev for m/z 16) Propene from the signal at 1 ev for m/z ) 8 1x x Ethylene from the signal at 11 ev for m/z 8) Butene isomers from the signal at 1.5 ev for m/z 56) Figure S3: Comparison of mole fraction profiles obtained using gas chromatography () and SVUV-PIMS ( ) for small hydrocarbon reaction products (fuel inlet mole fraction of.).
5 . Comparison for -methyl-pentane 5x methyl-pentane Oxygen Figure S: Comparison of mole fraction profiles obtained using gas chromatography () and SVUV-PIMS ( ) for 3-methyl-pentane and oxygen (fuel inlet mole fraction of.). The signals recorded at 11 ev for m/z 86 and at 16.6 ev for m/z 3 were used for the quantification of -methyl-pentane and oxygen, respectively.
6 5x Carbon Monoxide from the signal at 16.6 ev for m/z 8) x Carbon Dioxide from the signal at 16.6 ev for m/z ) x Methanol from the signal at 11 ev for m/z 3) x Acetaldehyde from the signal at 1.5 ev for m/z ) Figure S5: Comparison of mole fraction profiles obtained using gas chromatography () and SVUV-PIMS ( ) for oxygenated reaction products (-methyl-pentane inlet mole fraction of.).
7 5x x Methane from the signal at 16.6 ev for m/z 16) Propene from the signal at 1 ev for m/z ) x x Ethylene from the signal at 11 ev for m/z 8) Iso-butene from the signal at 1.5 ev for m/z 56) Figure S6: Comparison of mole fraction profiles obtained using gas chromatography () and SVUV-PIMS ( ) for small hydrocarbon reaction products (-methyl-pentane inlet mole fraction of.).
8 3. Comparison for,-dimethyl-butane 5x ,-dimethyl-butane Oxygen Figure S7: Comparison of mole fraction profiles obtained using gas chromatography () and SVUV-PIMS ( ) for,-dimethyl-butane and oxygen (fuel inlet mole fraction of.). The signals recorded at 11 ev for m/z 86 and at 16.6 ev for m/z 3 were used for the quantification of,-dimethyl-butane and oxygen, respectively.
9 5x Carbon Monoxide from the signal at 16.6 ev for m/z 8) x Carbon Dioxide from the signal at 16.6 ev for m/z ) x Methanol from the signal at 11 ev for m/z 3).x Acetaldehyde from the signal at 1.5 ev for m/z ) Figure S8: Comparison of mole fraction profiles obtained using gas chromatography () and SVUV-PIMS ( ) for oxygenated reaction products (,-dimethyl-butane inlet mole fraction of.).
10 8x1-3 6 Methane from the signal at 16.6 ev for m/z 16) 8x1-3 6 Ethylene from the signal at 11 ev for m/z 8) x Propene from the signal at 1 ev for m/z ) Figure S9: Comparison of mole fraction profiles obtained using gas chromatography () and SVUV-PIMS ( ) for small hydrocarbon reaction products (,-dimethyl-butane inlet mole fraction of.). It was not possible to quantify iso-butene from the SVUV-PIMS data because the signal of iso-butene is masked by the large signal of the fragment at m/z 56 coming from the decomposition of the fuel molecular ion.
11 II. Mass spectra of cyclic ethers which were not in databases. 5x1 3 Relative Intensity 3 1 -ethyl-tetrahydrofuran O 6 m/z Figure S1: Mass spectrum of -ethyl-tetrahydrofuran (detected in the oxidation of n-hexane). Relative Intensity 16x ethyl,-methyl-oxetane O 6 m/z Figure S11: Mass spectrum of -ethyl,-methyl-oxetane (detected in the oxidation of n-hexane).
12 Relative Intensity propyl-oxetane O 6 m/z Figure S1: Mass spectrum of 3-propyl-oxetane (detected in the oxidation of -methyl-pentane). 1x1 3 Relative Intensity ,3-dimethyl-tetrahydrofuran O 6 m/z Figure S13: Mass spectrum of,3-dimethyl-tetrahydrofuran (detected in the oxidation of 3-methyl-pentane).
13 Relative Intensity methyl-tetrahydropyran O m/z Figure S1: Mass spectrum of -methyl-tetrahydrofuran (detected in the oxidation of 3-methyl-pentane). Relative Intensity 6x ,3-methyl,ethyl-oxetane O 6 m/z Figure S15: Mass spectrum of 3,3-methyl,ethyl-oxetane (detected in the oxidation of,-dimethyl-butane).
14 6x1 3 Relative Intensity 5 3 1,3,3-trimethyl-oxetane O 6 m/z Figure S16: Mass spectrum of,3,3-trimethyl-oxetane (detected in the oxidation of,-dimethyl-butane). 5x1 3 Relative Intensity 3 1 3,3-dimethyl-tetrahydrofuran O 6 m/z Figure S17: Mass spectrum of 3,3-dimethyl-tetrahydrofuran (detected in the oxidation of,-dimethylbutane).
15 III. Structures of the parent cations obtained from the ionization of ketohydroperoxydes and diones. Table S1: Structures of the parent cation and calculated ionization energies of ketohydroperoxides detected during the oxidation of hexane isomers. Name Structure of the parent cation Calculated ionization energy (ev) From n-hexane -hydroperoxyhexan--one 9. 5-hydroperoxyhexan-3-one hydroperoxyhexan-3-one hydroperoxyhexanal 9.9 -methyl- -hydroperoxypentan--one From -methyl-pentane methyl- 3-hydroperoxypentanal methyl- 1-hydroperoxypentan-3-one methyl-3-hydroperoxypentanal 9.1
16 -methyl-1-hydroperoxy pentan-3- one 9.36 From 3-methyl-pentane 3-methyl-3-hydroperoxy pentanal methyl--hydroperoxy pentan-- one ethyl-3-hydroperoxybutanal 9. 3-(hydroperoxymethyl)pentan--one 9.6 -(hydroperoxymethyl)-- methylbutanal From,-dimethyl-butane 9.1,-dimethyl-3-hydroperoxybutanal ,3-dimethyl--hydroperoxybutanone 9.33
17 Table S: Structures and calculated ionization energies of diones detected during the oxidation of hexane isomers. Name Structure of the parent cation Calculated ionization energy (ev) From n-hexane,-hexadione oxo-hexanal 9.37 From -methyl-pentane -methyl-3-oxo-pentanal 9.6 -methyl-3-oxo-pentanal 9.6 From 3-methyl-pentane 3-methyl-,-pentadione ethyl-3-oxobutanal 9.3 From,-dimethyl-butane -ethyl-methylpropanedial 9.31,-dimethyl-3-oxobutanal 9.13
18
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