Hydrodealkylation, industrial

Naphthalene (qv) from coal tar continued to be the feedstock of choice ia both the United States and Germany until the late 1950s, when a shortage of naphthalene coupled with the availabihty of xylenes from a burgeoning petrochemical industry forced many companies to use o-xylene [95-47-6] (8). Air oxidation of 90% pure o-xylene to phthaUc anhydride was commercialized ia 1946 (9,10). An advantage of o-xylene is the theoretical yield to phthaUc anhydride of 1.395 kg/kg. With naphthalene, two of the ten carbon atoms are lost to carbon oxide formation and at most a 1.157-kg/kg yield is possible. Although both are suitable feedstocks, o-xylene is overwhelmingly favored. Coal-tar naphthalene is used ia some cases, eg, where it is readily available from coke operations ia steel mills (see Steel). Naphthalene can be produced by hydrodealkylation of substituted naphthalenes from refinery operations (8), but no refinery-produced napthalene is used as feedstock. Alkyl naphthalenes can be converted directiy to phthaUc anhydride, but at low yields (11,12). 

Raw materials for obtaining benzene, which is needed for the production of alkylbenzenes, are pyrolysis gasoline, a byproduct of the ethylene production in the steam cracking process, and coke oven gas. Reforming gasoline contains only small amounts of benzene. Large amounts of benzene are further produced by hydrodealkylation of toluene, a surplus product in industry. 

A cracking process, the dealkylation of alkylbenzenes, became an established industrial synthesis for aromatics production. Alkylbenzenes (toluene, xylenes, tri-methylbenzenes) and alkylnaphthalenes are converted to benzene and naphthalene, respectively, in this way. The hydrodealkylation of toluene to benzene is the most important reaction, but it is the most expensive of all benzene manufacturing processes. This is due to the use of expensive hydrogen rendering hydrodealkylation too highly dependent on economic conditions. 

As this book serves as an introduction, we do not go into more complex examples whose formulation and solution procedure are out of the scope of this work. For those interested in the topic, we recommend specialized literature on systematic process design and optimization [14,15]. Furthermore, the literature is rich in papers on the design of different facilities of industrial interest such as hydrocarbon separation [16], hydrodealkylation (HDA) production process optimization [4], distillation columns sequence design, heat exchanger networks, power plants and IGCC modeling... 

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