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Title: Catalytic pyrolysis of nitro aromatic compounds
Author: Nicolson, Iain Sinclair
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2003
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The work contained in this thesis was intended to study the rearrangement of o-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. o-Nitrotoluene was found to give conversion to toluene in 5.5% yield with recovery of starting material (12%). FVP of m-nitrotoluene gave recovery of toluene in 8% yield and starting material (7%). FVP of p-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. o-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); o-toluidine and toluene were identified as minor products in several of the pyrolyses. m-Nitrotoluene over alumina gave aniline and m-toluidine. p-Nitrotoluene over zeolite Y alumina gave conversion to aniline and p-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 1H-indol-3(2H)-one in 86% yield. FVP of 3-methylanthranil over zeolite mordenite at 500°C gave conversion to 1H-indol-2(2H)-one in 11% yield along with unreacted starting material (6%). FVP of 1H-indol-3(2H)-one over zeolite mordenite at 500°C gave rearrangement to 1H-indol-2(2H)-one in 37% yield. FVP of anthranil over zeolite Y at 500°C gave conversion to aniline in 28% yield.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available