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was increased. P a aB oh o nt a0 c ws wB es s l e tl oe ee h Even when we changed the BA/phenol molar ratio (Figure 6), the highest overall selectivity to HB chieved was not higher than 32%. An excess of phenol, in experiments carried out at a BA/phenol mol tio equal to 0.5 and 0.16, should be kinetically unconducive to an intermolecular transformation of P compared to a Fries-type rearrangement; therefore, we might expect a change in the HBPs compared to a Fries-type rearrangement; therefore, we might expect a change in t p-/o-HBP ratio in the presence of both the inter- and intra-molecular mechanisms -/o-HBP ratio in the presence of both the inter- and intra-molecular mechanisms of PB transformati of PB transformation into HBPs. With experiments carried out using a BA/phenol to HBPs. Wmitohlaerxrpaetiroim≤e1n, thsecpa-r/roie-HdBoPutseulescintigvitayBraAti/opwheansobletmwoeleanr1r.a5taiond≤21.,0,thwehepr-e/oas-HinBP selectivi tio was between 1.5 and 2.0, whereas in the case of the BA/phenol ratio of two, it was lower than 1. the case of the BA/phenol ratio of two, it was lower than 1.0. Figure 6. Effect of the BA/Ph molar ratio on phenol (Ph) and benzoic acid (BA) Figure 6. Effect of the BA/Ph molar ratio on phenol (Ph) and benzoic acid (BA) conversion conversion and selectivity to phenylbenzoate (PB) and hydroxybenzophenones and selectivi(tHyBtPos)p. hCeantaylylbste: nHzYo-7a,terea(PctBio)n atinmde h4 yhd, Tro=x1y9b0enCz. ophenones (HBPs). Catalyst: HY-7, reaction time 4 h, T = 190 °C. In order to gain more information on the reaction network, we conducted some In order to gain more information on the reaction network, we conducted some experiments in whi experiments in which we reacted PB; we observed that the peak conversion of PB was reached with HY-3 (43%), the lowest with HY-100 (6%) and the intermediate e reacted PB; we observed that the peak conversion of PB was reached with HY-3 (43%), the lowe value of 18% for HY-7. These results were in line with the PB selectivity decrease ith HY-100 (6%) and the intermediate value of 18% for HY-7. These results were in line with the P registered in phenol benzoylation experiments, during which PB underwent almost lectivity decnroeacsoensrecguitsitveeretdrainnsfpohrmenaotilobnewnzitohyHlaYti-o1n00e. xSpuerrpimriseingtsl,y,dhuorwinegvwer,hnicohHPBP uwnadserwent almo o consecutive transformation with HY-100. Surprisingly, however, no HBP was formed in the formed in these experiments, with the exception of some traces observed with the most active HY-3 compound. The only products found were phenol and BA. On the xperiments, with the exception of some traces observed with the most active HY-3 compound. The on one hand, this indicates the presence of water in the zeolites (the greater amount roducts found were phenol and BA. On the one hand, this indicates the presence of water in the zeolit being obviously shown with the more hydrophilic zeolite), which are responsible he greater afmorouthnet hbyedinroglyosbisviofutshleyeshteorw, bnuwt oitnhththeeomthoerehahnyd,rothpihsisluicggzesotlsiteh)a,twbohtihchthaere responsib r the hydrolysis of the ester, but on the other hand, this suggests that both the intramolecular Fri intramolecular Fries rearrangement and the intermolecular reaction between two molecules of PB are slowed greatly under these conditions with H-Y catalysts. arrangement and the intermolecular reaction between two molecules of PB are slowed greatly und It can be concluded that with H-Y zeolites, the presence of water (which is ese conditions with H-Y catalysts. generated in situ during phenol benzoylation tests) has a pronounced slowing effect 129 ◦PDF Image | Zeolite Catalysis
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