| Summary: | The work contained in this thesis was intended to study the rearrangement of <i>o</i>-nitrotoluene to anthranil which has previously been shown to occur under a variety of conditions. Flash Vacuum Pyrolysis (FVP) of nitrotoluene over zeolite 13X was carried out. <i>o</i>-Nitrotoluene was found to give conversion to toluene in 5.5% yield with recovery of starting material (12%). FVP of <i>m</i>-nitrotoluene gave recovery of toluene in 8% yield and starting material (7%). FVP of <i>p</i>-nitrotoluene gave only a trace of toluene with mainly recovery of unreacted starting material (12%). FVP of 1-ethyl-2-nitrobenzene over zeolite 13X gave conversion to ethylbenzene in 13% yield and styrene in 4% yield along with recovery of a trace of starting material. FVP of nitrotoluene was also carried out over the zeolites A, Y, ZSM-5 and mordenite as well as alumina and silica. <i>o-</i>Nitrotoluene was found to give conversion to aniline by a combined reduction and dealkylation in yields from 5-41% with unreacted starting material (0-515); <i>o</i>-toluidine and toluene were identified as minor products in several of the pyrolyses. <i>m-</i>Nitrotoluene over alumina gave aniline and <i>m</i>-toluidine. <i>p-</i>Nitrotoluene over zeolite Y alumina gave conversion to aniline and <i>p</i>-toluidine. FVP of 1-ethyl-2-nitrobenzene over these zeolites, silica and alumina gave conversion to aniline and indole in varying amounts; minor products of styrene, 2-vinylaniline and ethylaniline were also observed. FVP of 3-methylanthranil with no catalyst at 700°C gave conversion to 1<i>H</i>-indol-3(2<i>H</i>)-one in 86% yield. FVP of 3-methylanthranil over zeolite mordenite at 500°C gave conversion to 1<i>H-</i>indol-2(2<i>H</i>)-one in 11% yield along with unreacted starting material (6%). FVP of 1<i>H-</i>indol-3(2<i>H</i>)-one over zeolite mordenite at 500°C gave rearrangement to 1<i>H</i>-indol-2(2<i>H</i>)-one in 37% yield. FVP of anthranil over zeolite Y at 500°C gave conversion to aniline in 28% yield.
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