Chlor naphthalenes

Roburites were also manufd in Engl by the Roburite Explosives Co, Ltd, who had the following formulation on the old permitted list AN 88, dinitrobenzene 11 and chlor-naphthalene 1%. The following compn passed the Rotherham test and was on the permitted list AN 61, TNT 16 and Na chloride 23%. Its limit charge was 18 oz, and its power (by swing of BalPend) was 2.86 inches (Ref 4)... 

Chlor Naphthalenes.—Another series of reactions which support the view just discussed, that in naphthalene there are present two nuclei either one of which is a benzene ring, is found in Laurent s work on the chlorine substitution products of naphthalene. When naphthalene is chlorinated it yields different chlor naphthalenes. Two of these are important in this place, viz., a tetra-chlor naphthalene, C10H4CI4 and a penta-chlor naphthalene, C10H3CI5. Now the first one must have all four chlorines linked to one nucleus because on oxidation it yields ortho-phthalic acid, as below. The penta-chlor compound must of necessity have at least one of the chlorines linked to the second nucleus as only four are possible of being linked to one nucleus. Now this compound on oxidation yields not mono-chlor phthalic acid but tetra-chlor phthalic acid. The reactions may be represented as follows ... 

Trinitro-1-Naphthol (2,4,5-Trinitro-1-hydroxy naphthalene). Yellow leaflets or prisms mp 189—90° bp, explds. Sol in hot AcOH, si sol in hot w, ale, benz, eth acetate, xylene cold AcOH. Prepn from 2,4-dinitro-naphthol by nitration, or from 4-chlor-1,3,8-trinitronaphthalene by heating with 0.1 N NaOH in w or ale... 

Trinitro-3-chlor-l-oxy-naphthalene, X,X,X-trinitro-4-chlor-2-oxy-naphthalene). (O2N)3C10H3C1.0H, mw 313.62, N 13.40%, OB to C02 -76.53% crysts from AcOH with 1 mol AcOH as yellow-blue needles, mp M56°... 

Jaward, F M., Barber, J. L., Booij, K., Jones, K. C. Spatial distribution of atmospheric PAHs and PCNs along a north-south Atlantic transect. Environmental Pollution, 132 173-181 (2004). Kannan, K., Imagawa, T., Blankenship, A. L., Giesy, J. P. Isomer-specific analysis and toxic evaluation of polychlorinated naphthalenes in soil, sediment, and biota collected near the site of a former chlor-alkali plant. Environmental Science and Technology, 32 2507-2514 (1998). 

Cyclopropan 1-Chlor-l-(l-chlor-2-methyl)-l-propenyl)-tetramethyl-El7a, 583 [1,2-CI2-3,3-(CH 3) —cyclopropen 4 En] Naphthalene m-4a-(Dich ormethyl)-decahydro- E21a, 1129 (H - CHC12)... 

Trinitro-2-Naphthol (l,6,8-Trinitro-2-hydroxy naphthalene). Light yellow crysts, mp 221°. Prepn from 7-chlor-l,3,8-trinitro-naphthalene by treating with NaOH soln in the presence of acet. Explds on heating Refs 1) Beil 6, (610) 2) E.J. van der... 

Hexa-chlor benzene is formed by the chlorination not only of benzene itself, but also of other more complex hydrocarbons, e.g, naphthalene, anthracene, phenanthrene, di-phenyl methane (but not diphenyl). Penta-chlor benzene is of interest because it was at one time supposed to exist in isomeric forms which is contrary to the Kekule theory. 

In the first case one nucleus remains as a benzene ring in phthalic acid while in the second case it must be the other nucleus which remains as a benzene ring in tetra-chlor phthalic acid. The proof here then is exactly the same as in the case of nitro naphthalene and amino naphthalene, viz., that in naphthalene either nucleus is a benzene ring. 

Substitution Products.— The halogen derivatives of naphthalene include both substitution and addition products. The tetra- and penta-chlor substituted naphthalenes have already been referred to as furnishing proof that in naphthalene there are present two benzene nucleii (p. 771). Other halogen substituted naphthalenes are known but none need be discussed in detail. ... 

Addition Products.—The halogen addition products of naphthalene ,re more easily formed than are the substitution products. The tetra-chlor compound is of special interest and has been referred to. We have stated that naphthalene is oxidized to or//fo-phthalic acid. This oxidation was originally carried out not with naphthalene itself but with naphthalene tetra-chloride, CioHgCU. When naphthalene is treated with chlorine (potassium chlorate, KCIO3 and hydrochloric acid HCl), addition takes place and the tetra-chlor addition product is formed. By the further action of the chlorine, as an oxidizing agent, the tetra-chloride is converted into ortho-phthalic acid. 

Naphthalene to Anthranilic Acid.—Such a cheap source was found in naphthalene which was converted into anthranilic acid, orthoamino benzoic acid, and this by treatment with chlor acetic acid yields phenyl glycine ortho-carboxylic acid. The complete synthesis is as follows Naphthalene is oxidized to or// o-phthalic acid which then yields phthalic anhydride. This with ammonia, as ammonium carbonate, yields phthalimide or phthalamidic acid. 

Other nitro-derivatives of hydrocarhons and of phenols are used in explosive mixtures. Among the former are dinitro-benzene, chlor-dinitro-benzene, dinitro-toluene, di- or tri-nitro-den-vatives of mesitylene, pseudocumene, and xylene, dinitro-naphthalene. Trinitro-naphthalene and tetra-nitro-naphthalene have also been proposed. Of the nitro-phenols, perhaps the most important is tri-nitro-cresol, known as Cresilite in France, where it is added to Melinite. Other nitro-derivatives of the aromatic series will be mentioned in the section on detonators. 

The aromatic polyketones, containing 1,4-naphthalene links were produced in Ref. [363] by the reaction of nucleophylic substitution of l-chlor-4-(4 -chlorbenzoyl)naphthalene with 1) 1,4-hydroquinone, 2) 4,4 -isopropylidenediphenol, 3) phenolphthalein, 4) 4-(4 -hydroxyphenyl) (2H)-phthalasine-l-one, respectively. All polymers are amorphous and dissipate in some organic solvents. The polymers have good thermo-stability and the high glassing temperatures. 

Chlor( ormyl(naphtha]ic anhydrideX a derivative of naphthalene-1,4,5-tricarboxylic acid, ami the acid iteelf were involved in preparing bis(naphthalic anhydrides) containing ester and amide groups (Sch e 26X... 

In the world practice, rawhide and ready leather is widely protected by the following compounds phenylmercury, bromo-acetophenone, n-chlor-/w-creosol, alkyl naphthalene-sulphodiacid, sodium borate, zinc oxide, 2-oxydiphenyl, salicylanihde, and some other. However, a wide application of some biocides is restricted by specific requirements to leather protection biocides must be soluble in fats, thermostable at stuffing temperature and compatible with other components used for leather treatment [15]. 

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