Oxidation of naphthalene

Prepared by the oxidation of naphthalene with sulphuric acid at 270-300 C in the presence of HgSO under these conditions the... 

Manufacture and Processing. Until World War II, phthaUc acid and, later, phthaUc anhydride, were manufactured primarily by Hquid-phase oxidation of suitable feedstocks. The favored method was BASF s oxidation of naphthalene [91-20-3] by sulfuric acid ia the presence of mercury salts to form the anhydride. This process was patented ia 1896. During World War I, a process to make phthaUc anhydride by the oxidation of naphthalene ia the vapor phase over a vanadium and molybdenum oxide catalyst was developed ia the United States (5). Essentially the same process was developed iadependendy ia Germany, with U.S. patents being granted ia 1930 and 1934 (6,7). 

Fixed-Bed Vapor-Phase Oxidation of Naphthalene. A sihca gel or sihcon carbide support is used for catalyst involved in the oxidation of naphthalene. The typical naphthalene oxidation catalyst is a mixture of vanadium oxide and alkali metal sulfate on the siUca support. Some changes, such as the introduction of feed vaporizers, are needed to handle a naphthalene feed (14), but otherwise the equipment is the same. 

Toluene hydrodealkylation to benzene and methane Phthalic anhydride by air oxidation of naphthalene Trickle bed reactor for hydrodesulfurizatiou... 

Phtnalic anhydride is made by oxidation of naphthalene at temperatures of 340 to 380°C (644 to 716°F) controlled by heat exchangers immersed in the bed. At these temperatures the catalyst is stable and need not be regenerated. The excellence of temperature control was a major fac tor for the adoption of this process, but it was obsolesced by 1972. 

Enzymatic oxidation of naphthalene by bacteria proceeds by way of the intermediate ciy-diol shown. Which prochiral faces of C-1 and C-2 of naphthalene are hydroxylated in this process ... 

An alternative route to phthalic anhydride is the partial oxidation of naphthalene. The heat of reaction is — 430 kcal/mol. This reaction can be performed using a promoted V2O5 catalyst on silica, much like that considered in Example 9.1. Suppose In(fik) = 31.6800—19,100/T for the naphthalene oxidation reaction and that the subsequent, complete oxidation of phthalic anhydride follows the kinetics of Problem 9.3. Suppose it is desired to use the same reactor as in Example 9.1 but with a,>, = 53g/ m. Determine values for and T aii that maximize the output of phthalic anhydride from naphthalene. 

Cerniglia CE, DT Gibson, C van Baalen (1980b) Oxidation of naphthalene by cyanobacteria and microalgae. J Gen Microbiol 116 495-500. 

Narro ML, CE Cerniglia, C Van Baalen, DT Gibson (1992) Evidence for an NIH shift in oxidation of naphthalene by the marine cyanobacterium Oscillatoria sp. strain JCM. Appl Environ Microbiol 58 1360-1363. 

Jeffrey AM, HJC Yeh, DM Jerina, TR Patel, JF Davey, DT Gibson (1975) Initial reactions in the oxidation of naphthalene by Pseudomonas putida. Biochemistry 14 575-584. 

Table 5 Oxidation of naphthalene with H2O2 over phthalocyanines ...

I, 4-benzoquinone.4 Other methods that have been employed include the oxidation of naphthalene with hydrogen peroxide,5 the oxidation of 1,4-naphthalenediamine 6 and naphthylamine sulfonic acid 7 and the oxidation of 4-amino-1-naphthol prepared by electrolytic reduction of 1-nitronaphthalene.8... 

Fluidized bed reactors were first employed on a large scale for the catalytic cracking of petroleum fractions, but in recent years they have been employed for an increasingly large variety of reactions, both catalytic and non-catalytic. The catalytic reactions include the partial oxidation of naphthalene to phthalic anhydride and the formation of acrylonitrile from propylene, ammonia, and air. The noncatalytic applications include the roasting of ores and Tie fluorination of uranium oxide. 

PHTHALIC ANHYDRIDE PRODUCTION VIA THE CATALYTIC OXIDATION OF NAPHTHALENE IN A FIXED BED REACTOR... 

Either naphthalene or ortho-xylene is an acceptable starting material for partial oxidation to phthalic anhydride, but current raw materials costs favor the former as a starting material. Both fixed and fluidized bed processes have been used on a commercial scale, but you are to focus your attention on the former. Figure 13.5 is a schematic flow diagram of the proposed process. Most research groups that have studied the catalytic oxidation of naphthalene over vanadium pentoxide agree that the principal reactions are... 

Phthalic Anhydride Production Via the Catalytic Oxidation of Naphthalene in a Fixed Bed Reactor... 

A process, which considered the bio-oxidation of naphthalene compounds using naphthalenes-oxidizing bacteria, was applied for the treatment of gas oil. The quality of the product not only exhibited a sulfur content closed to specifications but also a high lubricity. Description on the used microbial strain was not provided [432],... 

Heyden-Wacker A process for making phthalic anhydride by the catalytic oxidation of naphthalene or o-xylene. Offered by Lurgi. 

Sapper An obsolete process for making phthalic anhydride by oxidizing o-xylene, using a mercury sulfate catalyst. Invented by E. Sapper in 1891 in the course of searching for a commercial route to indigo, and used until the catalytic gas-phase oxidation of naphthalene was introduced in 1925. 

The following model is proposed for the oxidation of naphthalene in a tubular flow reactor with constant wall temperature (Welsenaere Froment, Chem Eng Science 25 1503, 1970) ... 

Pulping additives such as quinoid compounds increase the yield of the pulp mass up to 4% [128]. For commercial application the most promising additives are anthraquinone (AQ) or the more convenient soluble salt of tetrahydroan-thraquinone (THAQ). If AQ or THAQ could be obtained at a price below 2/kg it would find a substantial market as a pulping additive [129], Commercial production of THAQ is now based on the partial thermochemical oxidation of naphthalene. In recent years, however, the lure of the pulp market has promoted several attempts to develop a process for the electrosynthesis of THAQ based on the indirect electrooxidation of naphthalene to naphthaquinone (NQ) with Ce4+, according to the stoichiometry of the reactions 1, 2 and 3. 

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