Table S1 the Relative Content of Bio-Oil Before Or After Upgrading

Table S1 The relative content of bio-oil before or after upgrading

bio-oil / case 1 / case 2 / case 3 / case 4 / case 5 / case 6
RT./min / Compounds / Relative content/%
acids / 5.54 / 0.72 / 0.1 / 0.52 / 0.1 / 0.48 / 0.09
1.93 / Acetic acid / 4.75 / 0.72 / 0.1 / 0.52 / 0.1 / 0.48 / 0.1
40.684 / Benzoic acid, 3,5-dimethyl- / 0.36
43.147 / Benzeneacetic acid, 4-hydroxy-3-methoxy- / 0.43
Aldehydes and ketones / 17.01 / 5.87 / 7.29 / 7.23 / 9.17 / 4.39 / 9.6
1.511 / Acetaldehyde, hydroxy- / 1.8
2.337 / 2-Propanone, 1-hydroxy- / 4.01 / 2.47 / 0.86 / 2.29 / 0.82 / 1.52 / 0.53
5.426 / Formamide, N,N-dimethyl- / 9.14 / 2.14 / 0.79 / 3.13 / 1.31 / 1.58 / 0.92
10.154 / 2-Butanone / 1.2 / 1.33 / 0.98
20.41 / 2-(5-Methyl-furan-2-yl)-propionaldehyde / 0.12 / 0.38 / 0.21
20.681 / 1,2-Cyclopentanedione, 3-methyl- / 0.79 / 0.52 / 0.27 / 0.67 / 0.32 / 0.67 / 0.35
29.259 / 2-Furancarboxaldehyde, 5-(hydroxymethyl)- / 0.47
32.523 / 2-Methoxyphenylacetone / 0.4 / 0.62 / 0.55
33.826 / 2-Methoxyphenylacetone / 1.36 / 1.59 / 1.05
34.365 / 5-Methyl-2(2-oxo-4-heptyl)furan / 0.81
35.302 / Vanillin / 1.27 / 0.74 / 0.32 / 0.67 / 0.22 / 0.62 / 0.26
40.413 / 2-Acetyl-1-tetralone / 1.97 / 2.58 / 3.94
esters / 8.23 / 14.87 / 11.91 / 15.08 / 30.64 / 22.12
1.248 / Formic acid, ethyl ester / 2.91 / 0.86
1.294 / Acetic acid, methyl ester / 3.59 / 1.43 / 0.09
1.793 / Ethyl Acetate / 5.71 / 2.04 / 0.18 / 0.05
1.958 / Propanoic acid, methyl ester / 0.64 / 0.22 / 0.29
2.377 / Acetic acid, butyl ester
3.457 / Butanoic acid, methyl ester / 0.08
3.484 / Formic acid, butyl ester / 7.94 / 3.39
7.195 / Acetic acid, butyl ester / 10.13 / 4.2
14.433 / Methyl-2-methoxy-4-methylpent-2-enoate / 0.61 / 0.73 / 1.01
16.084 / ethyl-2-methoxy-4-methylpent-2-enoate / 0.49 / 0.44 / 1.52
18.375 / Acetic acid, butoxyhydroxy-, butyl ester / 2.55 / 0.81
18.894 / Levulinic acid, methyl ester / 0.94 / 0.53
19.869 / Lactic acid, butyl ester / 0.42
22.516 / Levulinic acid, ethyl ester / 1 / 0.57
24.545 / Butanoic acid, 3-hydroxy-, methyl ester / 0.94
25.981 / 3-Acetoxy-2(1H)-pyridone / 0.29
26.224 / Octanoic acid, 6,6-dimethoxy-, methyl ester / 1.22
26.365 / 2,4-Hexadienedioic acid, dimethyl ester / 0.49
29.682 / Butanedioic acid, diethyl ester / 1.16 / 0.45
30.15 / 2-Isobutoxyethyl acetate / 0.43
30.347 / Levulinic acid, butyl ester / 1.28 / 0.71
30.727 / Butanoic acid, 2-butoxy-1-methyl-2-oxoethyl ester / 1.13 / 0.33
32.337 / Octanoic acid, 3-pentadecyl ester / 1.63 / 0.6
34.793 / Malonic acid, butyl 2-methylpentyl ester / 1.04 / 0.51
35.975 / Cyclopentanepropanoic acid, 2-methyl-3-oxo-, methyl ester, trans-(.+-.)- / 0.5
36.532 / Butanedioic acid, dibutyl ester / 1.25 / 0.96
36.628 / Orthoformic acid, tri-sec-butyl ester / 0.41
37.256 / Butanoic acid, 1-methylpropyl ester / 2.47 / 0.91
38.627 / 2-Cyclopentene-1-carboxylic acid, 1,2,3-trimethyl-, ethyl ester / 1.3 / 1.41 / 0.94
40.328 / 2,2-Dimethylpropionic acid,
cyclopentyl ester / 1.66
44.962 / Acetic acid, 1-methyl-4-oxo-bicyclo [3.1.0]hex-6-ylmethyl ester / 1.07 / 0.91
45.194 / 4,5-Dihydrooxazole-4-carboxylic acid, 4-ethyl-5-methyl-2-phenyl-, methyl ester / 6.71 / 7.34 / 6.23
48.33 / 3-Cyclopentylpropionic acid, 3-methylphenyl ester / 0.61 / 0.59
alcohols / 16.66 / 9.03 / 2.91 / 8.29 / 2.64 / 8.69 / 3.52
3.395 / 1,2-Ethanediol / 9.28 / 8.5 / 2.91 / 8.29 / 2.64 / 8.69 / 3.52
3.633 / Glycerin / 6.6 / 0.53
42.635 / Cyclohexanol, 3-methyl- / 0.78
ethers / 4.23 / 13.87 / 36.67 / 16.25 / 36.74 / 13.75 / 37.81
1.213 / Ethyl ether / 0.63 / 0.22
1.256 / Methane, dimethoxy- / 0.81 / 0.09
1.468 / 1,3,5-Trioxane / 3.18
1.593 / Paraldehyde / 0.91 / 0.08 / 0.41 / 0.32
1.634 / Ethane, 1,1-dimethoxy- / 0.36
2.399 / Furan, tetrahydro-2-methyl- / 0.27 / 0.36
2.491 / Acetic acid, ethoxy- / 0.76
3.697 / Ethane, 1,1-diethoxy- / 0.35
5.914 / 2-Propanone, 1,1-dimethoxy- / 0.74
6.12 / Glycolaldehyde dimethyl acetal / 0.59 / 0.12
6.627 / Ethane, 1,1,2-trimethoxy- / 4.2 / 0.54
12.206 / Furan, tetrahydro-2,5-dimethoxy- / 1.21 / 0.25
12.685 / 2,2'-Bi-1,3-dioxolane / 0.66 / 1.46
14.512 / Ethanol, 2,2-diethoxy- / 0.23
15.263 / Ethyl orthoformate / 0.87
15.597 / Ethane, 1,1,2,2-tetramethoxy- / 1.19 / 0.16
16.153 / 3,3-Diethoxy-1-propanol / 0.51
17.456 / 2-Furanmethanethiol, 5-methyl- / 0.18 / 0.56
17.911 / 2-Propanone, 1,1-dimethoxy- / 0.39
19.312 / Ethoxyacetaldehydediethylacetal / 3.57 / 0.31 / 0.71 / 0.17
20.097 / 2-Furanmethanol, tetrahydro- / 0.62 / 0.12
20.245 / Furan, 2,5-diethoxytetrahydro- / 1.52 / 0.16
20.304 / 1,4-Dioxane, 2,3-dimethoxy- / 0.49 / 0.08
21.303 / Ethane, 1,1,2,2-tetramethoxy- / 0.36
21.47 / 2,2'-Bi-1,3-dioxolane / 0.8
21.487 / 1,3-Dioxolane-2-methanol, 2,4-dimethyl- / 0.2
21.593 / Hexanal dimethyl acetal / 4.7
22.335 / Methane, dibutoxy- / 4.69 / 0.95
23.093 / 1,1,3-Trimethoxypropane / 0.35
23.707 / Methoxyacetaldehyde diethyl acetal / 0.29 / 0.12
24.051 / Butane, 1,1'-[ethylidenebis(oxy)]bis- / 0.63
24.172 / Benzofuran, 2-methyl- / 0.21 / 0.37 / 0.23
24.308 / 1,3-Diethoxy-2-propanol / 0.26
25.462 / N,N-Dimethylformamide di-n-butylacetal / 1.26
25.525 / 2,2'-Trimethylenebis-1,3-dioxolane / 0.99 / 1.08 / 1.06
25.566 / 1,3-Dioxolane-2-methanol / 0.25
25.797 / 4-Methoxypyridine-N-oxide
26.06 / Ethane, 1,1,2,2-tetraethoxy- / 0.33
26.22 / Hexanal dimethyl acetal / 1.18 / 1.38
26.433 / 1,1,3-Trimethoxypropane / 1.07
26.601 / cis-3-Hexenal diethyl acetal / 0.67 / 3.59
26.816 / 4-Methoxycarbonylbutyl-1-methyl-2-methoxycarbonylethyl ether / 0.51
26.986 / 2-Butanone, 4-(5-methyl-2-furanyl)- / 0.23 / 0.24 / 0.33
27.165 / 3,3-Diethoxy-1-propanol / 0.81
27.405 / 1,1-Dimethoxy-2-phenylpropane / 0.14
27.594 / Ethene, (2-methoxyethoxy)- / 0.4
28.014 / dl-Glyceraldehyde diethylacetal / 0.44
28.2 / 2-tert-Butoxytetrahydrofuran / 0.78
28.506 / Benzofuran, 4,7-dimethyl- / 1.18 / 0.89 / 0.93
29.134 / Furan, 2,5-dimethyl- / 0.14 / 0.21
29.343 / Furan, 2-(2-furanylmethyl)-5-methyl- / 0.16 / 0.18 / 0.16
29.679 / Benzene, 1-(2,2-dimethoxyethyl)-4-methoxy-
29.93 / 1,3-Dioxolane, 2-(6-heptynyl)- / 0.24 / 0.37 / 0.34
30.386 / Methoxyacetaldehyde diethyl acetal / 0.55
31.143 / Furan, 2,2'-methylenebis[5-methyl- / 4.1 / 4.95 / 5.43
31.24 / Isobutyl ether / 1.49
31.486 / Diglycerol / 0.57
32.244 / 2,2'-Ethylidenebis(5-methylfuran) / 17.04 / 16.72 / 17.28
34.266 / 1-Butanol, 4-butoxy- / 1.58
34.549 / 2-Pentanone, 5,5-diethoxy- / 0.3 / 1.12 / 0.41
36.78 / Butane, 1,1'-[methylenebis(oxy)]bis- / 0.36
37.958 / 6-(5-Methyl-furan-2-yl)-hexan-2-one / 5.15 / 4.84 / 4.06
39.101 / p-Dioxane, 2,3-bis(tert-butyloxy)- / 1.17 / 4.06
39.483 / 2,2'-Isopropylidenebis(5-methylfuran) / 0.42 / 0.46 / 0.34
44.983 / 5-Methyl-2(2-oxo-4-heptyl)furan / 0.86
Phenols / 20.58 / 14.08 / 4.5 / 15.5 / 6.1 / 13.93 / 5.88
18.851 / Phenol / 0.63 / 0.42 / 0.18 / 0.57 / 0.23
22.245 / Phenol, 2-methyl- / 0.41 / 0.43 / 0.12 / 0.42 / 0.14
23.188 / Phenol, 4-methyl- / 0.79 / 0.77 / 0.18 / 0.61 / 0.22 / 0.43 / 0.2
23.488 / Phenol, 2-methoxy- / 1.02 / 0.31 / 1.03 / 0.35 / 0.54 / 0.26
26.188 / Phenol, 2,5-dimethyl- / 0.67 / 0.5 / 0.18 / 0.33
26.97 / Phenol, 2-ethyl- / 0.23
27.828 / Phenol, 2-methoxy-4-methyl- / 0.8 / 0.69 / 0.23 / 0.65 / 0.29 / 0.65 / 0.24
28.331 / 1,2-Benzenediol / 4.77 / 4.05 / 1.51 / 3.58 / 1.39 / 2.97 / 1.45
29.683 / Benzene, 1-ethyl-4-methoxy- / 0.23
30.589 / 1,2-Benzenediol, 3-methyl- / 0.92 / 0.69 / 0.31 / 0.66 / 0.29 / 0.98 / 0.6
31.662 / 1,2-Benzenediol, 4-methyl- / 3.29 / 2.19 / 0.97 / 2.11 / 0.96 / 2.16 / 1.02
32.379 / 2-Methoxy-4-vinylphenol / 0.72
33.178 / p-Butoxytoluene / 0.14
33.714 / Phenol, 2,6-dimethoxy- / 0.52 / 0.29 / 0.18 / 0.58 / 0.26 / 0.7 / 0.18
33.808 / 2,5-Dimethylhydroquinone / 0.29
33.916 / Phenol, 2-methoxy-4-(2-propenyl)- / 0.35 / 0.44 / 0.38
34.907 / 1,3-Benzenediol, 4-ethyl- / 2.23 / 1.64 / 1.42 / 0.51 / 1.27 / 0.78
36.973 / Phenol, 4-ethyl-2-methoxy- / 0.33 / 0.43 / 0.59
37.013 / Phenol, 2-methoxy-4-(1-propenyl)- / 0.75
37.906 / 1,3-Benzenediol, 4-propyl- / 0.79 / 0.75 / 0.68 / 0.51
38.181 / Ethanone, 1-(4-hydroxy-3-methoxyphenyl)- / 0.6 / 0.22 / 1.86 / 0.9 / 1.01
39.632 / 2-Propanone, 1-(4-hydroxy-3-methoxyphenyl)- / 0.73 / 0.46 / 0.35
43.139 / Methyl-(2-hydoxy-3-ethoxy-benzyl)ether / 0.5 / 0.7
43.514 / Benzaldehyde, 4-hydroxy-3,5-dimethoxy- / 0.41 / 0.35 / 0.31
45.568 / 2-Propenal, 3-(4-hydroxy-3-methoxyphenyl)- / 1.01 / 0.63
sugars / 35.24 / 47.68 / 14.4 / 38.82 / 18.5 / 27.79 / 9.05
31.369 / .alpha.-L-Galactopyranoside, methyl 6-deoxy- / 1.18
32.689 / .beta.-d-Mannofuranoside, methyl / 0.23 / 1.2
33.403 / Ethyl .beta.-d-riboside / 0.43 / 0.92
34.114 / .alpha.-D-Glucopyranoside, methyl / 1.28 / 0.48
35.951 / Lactose, .beta.- / 0.41 / 0.16
36.73 / 4-O-Hexopyranosylhexose / 6.17
38.523 / Levoglucosan / 27.79
38.73 / .alpha.-D-Glucopyranose, 4-O-.beta.-D-galactopyranosyl- / 0.38
39.796 / .alpha.-D-Mannofuranoside, 1-O-heptyl- / 1.62 / 0.86
40.656 / .beta.-D-Glucopyranose / 1.39
40.982 / Methyl-.beta.-D-arabinopyranoside / 0.6
41.225 / .alpha.-D-Glucopyranoside, methyl / 46.5 / 14.17
42.41 / Ethyl .alpha.-d-glucopyranoside / 36.83 / 16.04
44.099 / D-Glucose, 4-O-.alpha.-D-glucopyranosyl- / 1.87
47.333 / Octyl-.beta.-D-glucopyranoside / 22.78 / 8.19