## 2 Results and Discussion
### Reactivities of Model Bio-Oil Components
\begin{table}
\begin{tabular}{l c l} \hline
**Olefins** & **PC (\%)** 1  & **Product distributions (GC area \%)** 1  \\ \hline
1,7-Ocadiene & 52.4 & _Skeletal isomers (4.5\%)_: 1,6-ocadiene, 3,5-ocadiene, 2-methyl-1,5-heptadiene, 2,4-dimethyl-1,5-hexadiene, 3-methyl-1,5-heptadiene, _etc._ \\  & & **Cycloelefins (14.2\%)**: bicyclo[4.1.0]heptane, 2-methylbicyclo[2.2.1]heptane, 4-ethyl-1-cyclohexene, cycloococene,1-ethyl-2-methylcyclopentene, 1,6-dimethyl-cyclohexene,ethyldienedicyclohexane, 1,2-dimethyl-1-cyclohexene, _etc._ \\  & & **Alcohols and ethers (8.8\%)**: 1,7-ocenedi, 4-ethylcyclohexanol, 1-ethylcyclohexanol, 2-propyl-tetrahydrofuranbropyran, 2,5-diethyltetrahydrofour-an, 2-propyltetrahydrofuranbropyran, 2-butyl-3-ethyloxirane, _etc._ \\  & & **\(O\)-Alkylates (33.4\%); Mono-C-alkylates (4.1\%); Di-\(C\)-alkylates (10.1\%)** \\ \hline Cyclohexene & 62.0 & **Oligomers (0.2\%)**:1-cyclohexyl-1-cyclohexene, _etc._ \\  & & **Alcohols and ethers(1.4\%):cyclohexanol, di-cyclohexyl ether** \\  & & **\(O\)-Alkylates (2.9\%)**: cyclohexyl phenyl ether \\  & & **Mono-\(C\)-alkylates (33.4\%): \(o\)-cyclohexylphenol, \(p\)-cyclohexylphenol** \\  & & **Di-\(C\)-alkylates (26.8\%); Tri-\(C\)-alkylates (8.3\%):2,4,6-tricyclohexyl-phenol** \\ \hline
1-Octene & 74.5 & **Skeletal isomers (12.1\%)**:2-octene, 3-octene, 4-ocene, 1-octene. \\  & & **Alcohols and ethers (5.1\%):2-octanol, 3-octanol dioctyl ethers, _etc._ \\  & & **\(O\)-Alkylates (48.6\%)**:2-Octyl phenyl ether, 3-Octyl phenyl ether, _etc._ \\  & & **Mono-C-alkylates (14.5\%): \(o\)-ocylphenol, \(p\)-octylphenols, _etc._ \\  & & **Di-\(C\)-alkylates (11.5\%): 2,4-di-octylphenols, 2,6-dicotylphenols, \\ \hline
2,4,4-Trimethyl & 89.9 & **Skeletal isomers (4.7\%): 2,4,4-trimethyl-1-pentene, 3,4,4-trimethyl-2-pentene, _etc._ \\ -pentene & & **Fragments and oligomers (3.8\%): 4,4-dimethyl-2-neopentyl-1-pentene, 2,2,4,6,6-pentamethyl-3-heptene, 2,2,4,4,6,8,8-heptamethyl-nonane, 2,4,4,6,6,8,8-heptamethyl-1-nonene, 2,2,4,6,6- pentamethyl-3-heptene,_etc._ \\  & & **Alcohols and ethers (1.8\%): 2,5,5-trimethyl-2-pentanol** \\  & & **Mono-\(C\)-alkylates (64.2\%): \(p\)-(1,1,3,3-tetramethylbutyl)phenol, \(o\)-\(t\)-butylphenol, _etc._ \\  & & **Di-\(C\)-alkylates (12.1\%): 2,4-di-\(t\)-butylphenol, 2,5-di-\(t\)-butylphenol, 2,6-di-\(t\)-butylphenol, 2-\(t\)-butyl-4-(1,1,3,3-tetramethylbutyl)phenol, _etc._ \\  & & **Tri-\(C\)-alkylates (6.7\%): 2,4,6-tri-\(t\)-butylphenol** \\ \hline \end{tabular}
\end{table} 
Table 10: Product distributions and phenol conversions in addition reactions by different olefins in phenol/water at 120 \({}^{\circ}\)C in 3h over the SSA catalyst 1. In addition, intermolecular dehydration of 1-butanol occurred producing dibutyl ether with both Dowex50 WX2 and SSA (Table 11). Also, traces of butyl phenyl ether were formed. Small amounts of _t_-butyl phenols (0.9%) were detected when 2-butanol was used as replacement of 1-butanol over SSA. Under acid catalyzed conditions, 2-butanol was protonated, and then dehydrated generating secondary carbocations. Some isomerization to tertiary carbocations must then occur. Phenol added to these C4 cations generating _O_-_t_-butylated phenol, followed by isomerization of the _t_-butyl phenyl ether to the _thermodynamic C_-_t_-butylated phenol products along with some bis-alkylated phenols formation (Scheme 9). Also, both acetic acid esterification and acetaldehyde acetalation reactions with 1-butanol occurred, generating butyl acetate and 1,1-dibutoxyethane (acetal), respectively, when acetic acid and acetaldehyde were present.