Catalytic Oxidations of Naphthalene Series

Abstract

Vapor-phase catalytic oxidations were made on commercial naphthalene, practical Tetra-Iin, 95 per cent 2-methylnaphthalene and 70 per cent 1 -methylnaphthalene to yield chiefly phthalic anhydride. Quinone by-products were found in small amounts. The most successful catalyst consists of pure pyrolytic vanadium pentoxide fused on glassy silica gel. A tin-bearing vanadium catalyst was tried with but moderate success.

Production of Benzene Poly(carboxylic acid)s and Small-Molecule Fatty Acids from Lignite by Catalytic Oxidation in NaVO3/H2SO4 Aqueous Solution with Molecular Oxygen

“…Vanadium-based catalysts were widely used in catalytic oxidation reactions because of its excellent catalytic performance. − Shreve et al studied catalytic oxidation of 1-methyl naphthalene and 2-methyl naphthalene to phthalic acid with V 2 O 5 as the catalyst. Using vanadate catalyst, xylene could be oxidized to toluic aldehyde and phthalic anhydride .…”

Oxidative Dealkylation of Alkylaromatic Hydrocarbons. Naphthalene as Product in Vapor-Phase Air Oxidations of Monomethylnaphthalenes and Dimethylnaphthalenes over Vanadia

“…Elution chromatography of a 1.00-gram sample of the reaction product mixture from run No. 7 over chromatographic alumina with eluting solvent mixture ranging from petroleum ether through carbon tetrachloride, chloroform, and finally acetone yielded 23 fractions which were evaporated to dryness in tared flasks. A total of up to 12.3 wt.% pure naphthalene was detected in the product.…”

“…He concluded that naphthalene is not a reaction intermediate in the oxidation of methylnaphthalenes to phthalic anhydride. In the research related below, naphthalene was conclusively detected under reaction conditions which are well known to effect its further oxidation to phthalic anhydride (2,4,72,76,79,23). Naphthalene was first detected and isolated in the recovered hydrocarbon mixture obtained from the fluid-bed oxidation of 2,3-dimethylnaphthalene to phthalic anhydride.…”

“…intermediate in the heterogeneous vapor-phase air oxidation of either monomethylnaphthalenes or dimethylnaphthalenes over vanadia catalyst at reaction conditions which yield phthalic anhydride (4,16,23). However, oxidative dealkylations to parent homologs have been observed for other organic series.…”

Oxidation

“…REACTION KINETICS Performance data on vapor phase catalytic oxidations are reported by McBee, Hass, and Wiseman (148) of ethylene using silver oxide as a catalyst over the temperature range from 225°t o 325°C ., of fatty oils by Faith and Rollins (68), of ethyl alcohol by Michels and Keyes (158), and of ammonia to nitrous oxide using manganese oxide-bismuth oxide as the catalyst by Kobe and Hossman (121). Using a catalyst of vanadium oxide on silica gel, Shreve and Welborn investigated the vapor phase oxidation of naphthalene, Tetralin, 2-methylnaphthalene, and 1-methylnaphthalene with air (211). Kinetic data have been given on the vapor phase oxidation of halogenated hydrocarbons to maleic and fumaric acid, including -butyl chloride, -butyl bromide, n-dichlorobutane, mixed amyl chlorides, dichloropentane, polychloropentanes, and -hexyl chloride, with determination of the effects of temperature, space velocity, feed composition, and catalyst (65).…”