KiOR Compositional Profile for CAS# 1267611

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GC/MS Summary for BioOil Study: PQ‐ Characterization API 18.34 Analyst / Reviewer: DH / BADAM Direct Oxygen (wt. %): Density (g/cm 3 ): LIMS I.D.: O103231559 GC/MS Quant. Compounds BioOil OXYGEN CAS bp (C) C H O mw wt. % % F ld h d 50 00 0 21 1 2 1 30 026 Formaldehyde ‐ ‐ ‐ 21 1 2 1 30.026 0.00 Acetaldehyde 75 ‐ 07 ‐ 0 20.2 2 4 1 44.05 0.00

Cyclohexane 110 ‐ 82 ‐ 7 80.74 6 12 0 84.16 5.30 0.00 Methyl Vinyl Ketone 78 ‐ 94 ‐4 81.4 4 6 1 70.09 0.00 Butanal 123 ‐ 72 ‐ 8 74.8 4 8 1 72.11 0.00 2 ‐ Butanone 78 ‐ 93 ‐ 3 79.64 4 8 1 72.11 0.00 2,5 ‐ Dihydrofuran 1708 ‐ 29 ‐ 8 67.4 4 6 1 70.0898 0.00 Acetic Acid 64 ‐ 19 ‐ 7 118.1 2 4 2 60.05 0.00

Benzene 71 ‐43 ‐ 2 80.1 6 6 0 78.11 0.74 0.00 Benzene 2 80.1 6 6 0 78.11 Methyl Cyclohexane 108 ‐ 87 ‐ 2 101 7 14 0 98.18 4.57 0.00 1 ‐ hydroxy‐ 2 ‐ propanone 116 ‐ 09 ‐ 6 145 ‐ 146 3 6 2 74.09 0.00 Propanoic Acid 79 ‐ 09 ‐4 141 3 6 2 74.08 0.00 Toluene 108 ‐ 88 ‐ 3 110.6 7 8 0 92.14 4.11 0.00 Ethyl Cyclohexane 1678 ‐ 91 ‐ 7 130 ‐ 132 8 16 0 112.21 2.32 0.00 2 ‐ Cyclopenten ‐ 1 ‐ one 930 ‐ 30 ‐ 3 5 6 1 82.1 0.00 Furfural 98 ‐ 01 ‐ 1 96.08 5 4 2 96.08 0.00 Ethylbenzene 100 ‐41 ‐4 136 8 10 0 106.167 2.34 0.00 (p+m) Xylene 106 42 3 138 8 10 0 106 16 3 65 0 00 ‐ ‐ . . . 108 ‐ 38 ‐ 3 139 8 10 0 106.16 0.00 Styrene 100 ‐42 ‐ 5 145 8 8 0 104.15 0.00 o ‐Xylene 95 ‐47 ‐ 6 144 8 10 0 106.16 0.68 0.00 Isopropylbenzene (Cumene) 98 ‐ 82 ‐ 8 152 9 12 0 120.19 0.16 0.00 Propyl Cyclohexane 1678 ‐ 92 ‐ 8 155 9 18 0 126.24 0.77 0.00

n ‐ Propylbenzene 98 ‐ 82 ‐ 8 152 9 12 0 120.19 0.48 0.00

3 ‐ Ethyltoluene 620 ‐ 14 ‐4 158 ‐ 159 9 12 0 120.19 1.02 0.00 4 ‐ Ethyltoluene 622 ‐ 96 ‐ 8 162 9 12 0 120.19 1.41 0.00 y 1,3,5 ‐Trimethylbenzene 108 ‐ 67 ‐ 8 164.7 9 12 0 120.19 0.00 2 ‐ Ethyltoluene 611 ‐ 14 ‐ 3 164‐ 165 9 12 0 120.19 0.27 0.00 Phenol 108 ‐ 95 ‐ 2 181 9 6 1 94.11 0.44 0.07 1,2,4‐Trimethylbenzene 95 ‐ 63 ‐ 6 169 ‐ 171 9 12 0 120.19 0.59 0.00 Benzofuran 271 ‐ 89 ‐ 6 173 8 6 1 118.1 0.01 0.00 Isobutyl Benzene 538 ‐ 93 ‐ 2 170 10 14 0 134.22 0.02 0.00 1,2,3 ‐Trimethylbenzene 526 ‐ 73 ‐ 8 175 ‐ 176 9 12 0 120.19 0.15 0.00 Indane 496 ‐ 11 ‐ 7 176.5 9 10 0 118.176 2.59 0.00 Indene 95 ‐ 13 ‐ 6 175 185 9 8 0 116 16 0 00 ‐ . . 2 ‐ Methylphenol (o ‐ cresol) 95 ‐48 ‐ 7 191.5 7 8 1 108.14 1.49 0.22 4 ‐ Methylphenol (p ‐ cresol) 106 ‐44 ‐ 5 201.8 7 8 1 108.14 0.22 0.03 3 ‐ Methylpheol (m ‐ cresol) 108 ‐ 39 ‐4 202.8 7 8 1 108.14 0.00 7 ‐ Methylbenzofuran 17059 ‐ 52 ‐ 8 196.1 9 8 1 132.16 0.00 2 ‐ Methylbenzofuran 4265 ‐ 25 ‐ 2 197 ‐ 198 9 8 1 132.16 0.02 0.00 2 ‐ Ethylphenol 90 ‐ 00 ‐ 6 195 ‐ 197 8 10 1 122.16 0.83 0.11 2,5 ‐ Dimethylphenol 95 ‐ 87 ‐4 212 8 10 1 122.16 1.01 0.13 1 ‐ Methylindene 767 ‐ 59 ‐ 9 199 10 10 0 130.19 0.00 2 ‐ Methylindene 2177 ‐47 ‐ 1 205.6 10 10 0 130.19 0.00

3 ‐ Ethylphenol 620 ‐ 17 ‐ 7 8 10 1 122.16 0.13 0.02 4 ‐ Ethylphenol 123 ‐ 07 ‐ 9 218 8 10 1 122.16 0.09 0.01 2,3 ‐ Dimethylphenol 526 ‐ 75 ‐ 0 217 8 10 1 122.16 0.00 3,4‐ Dimethylphenol 96 ‐ 65 ‐ 8 227 8 10 1 122.16 0.00 1,2 ‐ Benzenediol (catechol) 120 ‐ 80 ‐ 9 245 6 6 2 110.11 0.00 5 ‐ (Hydroxymethyl) furfural 67 ‐47 ‐ 0 6 6 3 126.11 0.00 1 ‐ Indanol 697 ‐ 64 ‐ 3 9 10 1 134.18 0.00 3 ‐ Methyl ‐ 1,2 ‐ benzenediol 488 ‐ 17 241 7 8 2 124.14 0.00 benzenediol ‐ 5 1,4‐ Benzenediol (hydroquinone) 123 ‐ 31 ‐ 9 285 6 6 2 110.11 0.00 1,3 ‐ Benzenediol (Resorcinol) 108 ‐46 ‐ 3 6 6 2 110.11 0.00

david.strobel Page 1 4/11/2011KiOR Compositional Profile for CAS# 1267611

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GC/MS Summary for BioOil Study: PQ‐ Characterization API 18.34 Analyst / Reviewer: DH / BADAM Direct Oxygen (wt. %): Density (g/cm 3 ): LIMS I.D.: O103231559 GC/MS Quant. Compounds BioOil OXYGEN CAS bp (C) C H O mw wt. % % 4 M hl 1 2 b di l 8 251 7 8 2 124 14

‐ ety ‐ , ‐ enzenediol 452 ‐ 86 ‐ 8 251 7 8 2 124.14 0.00 Decahydronaphthalene (trans ‐ ) 493 ‐ 02 ‐ 7 185 10 18 0 138.25 0.30 0.00

Decahydronaphthalene (cis ‐ ) 493 ‐ 01 ‐ 6 193 10 18 0 138.25 0.03 0.00 Tetrahydronaphthalene 119 ‐ 64 ‐ 2 207 10 12 0 132.2 1.41 0.00 Naphthalene 91 ‐ 20 ‐ 3 218 10 8 0 128.17 0.09 0.00 2 ‐ Methylnaphthalene 91 ‐ 57 ‐ 6 241 ‐ 242 11 10 0 142.2 0.05 0.00 1 ‐ Methylnaphthalene 90 ‐ 12 ‐ 0 240 ‐ 243 11 10 0 142.2 0.02 0.00 Eugenol 97 ‐ 53 ‐ 0 254 10 12 2 164.2 0.00 2 ‐ Eth y lna p hthalene ‐ ‐ 251 ‐ 252 12 12 0 156.22 0.00

ylnaphthalene 939 27 5 252 12 12 0 156.22 0.01 2,6 ‐ Dimethylnaphthalene 581 ‐42 ‐ 0 262 12 12 0 156.22 0.00 2,7 ‐ Dimethylnaphthalene 582 ‐ 16 ‐ 1 263 12 12 0 156.22 0.00 1 ‐ Naphthalenol 90 ‐ 15 ‐ 3 278 ‐ 280 10 8 1 144.17 0.00 2 ‐ Naphthalenol 135 ‐ 19 ‐ 3 285 ‐ 286 10 8 1 144.17 0.00 Acenaphthylene 208 ‐ 96 ‐ 8 280 12 8 0 152.19 0.00 Levoglucosan 498 ‐ 07 ‐ 7 6 10 5 162.14 0.00 Acenaphthene 83 ‐ 32 ‐ 9 279 12 10 0 154.21 0.00 Fluorene 86 ‐ 73 ‐ 7 298 13 10 0 166.22 0.07 0.00 Phenanthrene 85 01 8 340 14 10 0 178 23 0 02 0 00 Ph enant h rene ‐ ‐ . . .

Anthracene 120 ‐ 12 ‐ 7 340 14 10 0 178.23 0.00 Fluoranthene 206 ‐44 ‐ 0 384 16 10 0 202.25 0.00 Pyrene 129 ‐ 00 ‐ 0 404 16 10 0 202.25 0.01 0.00 Benz[a]anthracene 56 ‐ 55 ‐ 3 437.6 18 12 0 228.29 0.00 Chrysene 218 ‐ 01 ‐ 9 448 18 12 0 228.29 0.00 Benzo[b]fluoranthene 205 ‐ 99 ‐ 2 20 12 0 252.31 0.00 Benzo[k]fluoranthene 207 ‐ 08 ‐ 9 480 20 12 0 252.31 0.00 Benzo[a]pyrene 50 ‐ 32 ‐ 8 495 20 12 0 252.31 0.00 [ ]py Indeno[123 ‐ cd]pyrene 193 ‐ 39 ‐ 5 497.1 22 12 0 276.33 0.00 Dibenz[a,h]anthracene 53 ‐ 70 ‐ 3 524 22 14 0 278.35 0.00 Benzo[ghi]perylene 191 ‐ 24 ‐ 2 > 500 22 12 0 276.33 0.00 GC/MS Semi ‐ Quant. Compounds CAS bp (C) C H O mw wt. % 2 ‐ Methylbenzaldehyde 529 ‐ 20 ‐4 199 8 8 1 120.06 0.00 2,3 ‐ Dihydrobenzofuran 496 ‐ 16 ‐ 2 188 8 8 1 120.06 0.00 2 yl thylphenol 1687 9 12 1 136 09 0 07 0 01

‐ Eth ‐ 5 ‐ meth y l p h eno l

‐ 61 ‐ 2 . . . 2,2' ‐ Bifuran 5905 ‐ 00 ‐ 0 8 6 2 134.04 0.00 1H ‐ Indenol 56631 ‐ 57 ‐ 3 9 8 1 132.06 0.00 1,3 ‐ Dimethylindene 2177 ‐48 ‐ 2 11 12 0 144.09 0.00 Retene 483 ‐ 65 ‐ 8 390 18 18 0 234.34 0.03 0.00

david.strobel Page 2 4/11/2011