Other alkylnaphthalenes from naphthalene

The alkaline earth salts of sulfonated dinonylnaphthalenes have commercial importance as lube-oil additives. They are produced by Friedel-Crafts alkylation of naphthalene with nonene at 60 to 80 °C using aluminum chloride and concentrating the dinonylnaphthalene by distillation and then sulfonating it with SO3 or oleum at 20 to 40 °C. 

Condensation products from naphthalenesulfonic acids and formaldehyde are also used as additives to improve the flow behavior of concrete. The degree of condensation (n) of these products, with a worldwide production of around 40,000 tpa, ranges from 5 to 8. 

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Uses. The most important commercial use for benzonitrile is the synthesis of benzoguanamine, which is a derivative of melamine and is used in protective coatings and molding resins (see Amino RESINS Cyanamides). Other uses for benzonitrile are as an additive in nickel-plating baths, for separating naphthalene and alkylnaphthalenes from nonaromatics by azeotropic distillation (qv), as a jet-fuel additive, in cotton bleaching baths, as a drying additive for acrylic fibers, and in the removal of titanium tetrachloride and vanadium oxychloride from silicon tetrachloride. 

There are indications that pure naphthalene (a constituent of mothballs, which are, by definition, toxic to moths) and alkylnaphthalenes are from three to 10 times more toxic to test animals than are benzene and alkylbenzenes. In addition, and because of the low water solubility of tricyclic and polycyclic (polynuclear) aromatic hydrocarbons (i.e., those aromatic hydrocarbons heavier than naphthalene), these compounds are generally present at very low concentrations in the water-soluble fraction of oil. Therefore, the results of this smdy and others conclude that the soluble aromatics of crude oil (such as benzene, toluene, ethylbenzene, xylenes, and naphthalenes) produce the majority of its toxic effects in the enviromnent. 

Other smaller volume synthetie base stoeks inelude alkylaromatics, such as alkylbenzenes and alkylnaphthalenes, pol5dsobutylenes, phosphate esters and silicone fluids. Among these synthetie base stocks, with the exception of phosphate esters and silieones, the starting materials are all derived from basie petrochemicals - ethylene, propylene, butenes, higher olefins, benzene, toluene, xylenes, and naphthalenes, as illustrated in Figure 1. 

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