## 2 Results and Discussion
### Reactivities of Model Bio-Oil Components
\begin{table}
\begin{tabular}{c c c c c|c c c c} \hline \hline \multirow{2}{*}{**Catalyst**} & \multirow{2}{*}{\begin{tabular}{c} **1-Butanol** \\ **Conv. (\%)** \\ \end{tabular} } & \multicolumn{3}{c|}{**Selectivity (\%)**} & \multicolumn{3}{c}{**Yield (\%) b**} \\ \cline{3-10}  & & \begin{tabular}{c} **Mono-O-** \\ **octylates** \\ \end{tabular} & \begin{tabular}{c} **Mono-C-** \\ **octylates** \\ \end{tabular} & \begin{tabular}{c} **Di-octylates** \\ \end{tabular} & \begin{tabular}{c} **Octanols** \\ **ethers** \\ \end{tabular} & \begin{tabular}{c} **Dioctyl** \\ **ether** \\ \end{tabular} & \
\begin{tabular}{c} **Dibutyl** \\ **ether** \\ \end{tabular} &
\begin{tabular}{c} _O_-Butylate** \\ \end{tabular} \\ \hline A15 & 60.9 & 84.2 & 14.5 & 1.2 & 6.3 & 2.0 & 11.9 & 0.14 \\ DX2 & 58.7 & 84.8 & 14.1 & 1.0 & 6.9 & 2.1 & 11.9 & 0.61 \\ SSA & 74.8 & 82.3 & 13.8 & 3.9 & 4.8 & 1.9 & 12.4 & 0.1 \\ Cs\({}_{2.5}\)/K10 & 8.2 & 53.4 & 46.6 & 0 & 0.1 & Nd & 0.1 & Nd \\ \hline \hline \end{tabular}  
* Reaction conditions: (solid catalyst, 0.15 g; time: 3 h; 1-octene: phenol: water: 1-butanol (mmol) = 10:10:11.6:3.4; bGC area% of involved compounds _versus_ the sum of the GC area% of all products remained after the reaction.  
\end{table} 
Table 11: Product distributions and 1-butanol conversions in acid-catalyzed 1-octene/ 1-butanol reactions with phenol/water at 120 \({}^{\circ}\)C a. **Scheme 9. ** Acid-catalyzed reactions of model bio-oil components with alcohol. Table 12 summarizes the product compositions of the model bio-oil (phenol/water/acetic acid/acetaldehyde/hydroxyacetone/D-glucose/2-hydroxymethylfuran mixtures) reactions with 1-octene/1-butanol over all five acid catalysts at 120 \({}^{\circ}\)C for 3 h [22]. In addition to alkylated phenols (both _O_-ocylated and _C_-ocylated), octanols, dibutyl ether and dioctyl ether, butyl acetate and various octyl acetates, 1-octene oligomers and isomers mentioned \begin{table}
\begin{tabular}{l c c c c c} \hline \hline \multicolumn{1}{c}{**Products**} & \multicolumn{5}{c}{**Peak area (\%)**} \\ \cline{2-6}  & **Cs\({}_{\text{2.5}}\)/K10** & **A36** & **A15** & **DX2** & **SSA** \\ \hline
**Unreacted** & & & & & \\
1-octene & 48.4 & 54.1 & 26.4 & 20.3 & 4.0 \\
1-butanol & 1.0 & 0.2 & 0.1 & 0.3 & 0.2 \\ phenol & 40.4 & 21.9 & 15.7 & 15.3 & 9.6 \\
1-Dodecane (Internal standard) & 1.4 & 1.4 & 1.5 & 1.8 & 3.0 \\ \hline
**In common** & & & & & \\
1-Octene isomers & 1.0 & 8.5 & 31.1 & 25.3 & 28.9 \\ Phenol octylates & 0.8 & 2.9 & 12.4 & 18.8 & 35.3 \\ Octanols & 0.1 & 2.3 & 2.6 & 3.8 & 1.5 \\ Dioctyl ethers & 0.1 & Nd & 0.1 & 0.3 & 1.3 \\ \({}^{\text{b}}\)1-Octene oligomers and their hydrates & 3.8 & 4.2 & 4.7 & 5.0 & 6.1 \\ Octyl acetates & 0.8 & 0.9 & 1.6 & 6.7 & 4.8 \\
1,1-Dibutoxyethane & 0.3 & 0.1 & 0.1 & 0.1 & 0.1 \\ Dibutyl ether & 1.4 & 0.1 & 0.3 & 0.4 & 2.7 \\ Butyl acetate & 0.3 & 2.9 & 3.0 & 1.7 & 2.3 \\ Butyl levulinate & 0.1 & 0.6 & 0.3 & 0.2 & 0.4 \\ \hline
**Independent** & & & & & \\
2-Hydroxy-3-methylcyclopent-2-enone & 0.1 & Nd & 0.1 & 0.1 & Nd \\
2-(2-Furylmethyl)furan & 0.1 & Nd & Nd & Nd & Nd \\ \hline \hline \multicolumn{6}{l}{\({}^{\text{a}}\) Reaction conditions: (catalyst, 0.15 g; 1-octene: 1-butanol: phenol: water: acetic acid: acetaldehyde: hydroxyacetone: d-glucose: 2-hydroxymethylfuran (g) = 1.35: 0.15: 0.94: 0.15: 0.12: 0.15: 0.15; time: 3 h; nd: not detected); these results were first noted in the preliminary communication of this work found in reference 23; \({}^{\text{b}}\) C8, C16 and C24 olefins and their hydrates.} \\ \end{tabular}
\end{table} 
Table 12: Product compositions of model bio-oil reactions with 1-octene/1-butanol over Cs\({}_{\text{2.5}}\)/K10, A15, A36, DX2 and SSA catalysts at 120 \({}^{\circ}\)C in 3 h \({}^{\text{a}}\). above, 1,1-dibutoxyethane and butyl levulinate were formed over all the catalysts. 1,1-Dibutoxyethane was formed by acetal formation between acetaldehyde and 1-butanol (Scheme 9). Levulinic acid reacted with 1-butanol forming butyl levulinate.