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424 CHEMISTRY AND TECHNOLOGY OF EXPLOSIVES

Later chemical investigations were aimed at establishing the conditions under

which individual nitronaphthalenes could be formed. From the numerous investi-

gations on the subject some of the more important work will be mentioned below.

Piria [10], by reacting naphthalene with nitric acid at room temperature for

5-6 days obtained mononitronaphthalene.

Roussin [11] prepared a mixture of mono- and di-nitronaphthalenes which he

was able to separate by utilizing the fact that the latter is not soluble in carbon

disulphide.

Troost [12] obtained nitro- and dinitro-naphthalenes by successive nitration

of naphthalene. Darmstädter and Wichelhaus [13] found that the dinitronaphthalene

thus obtained was a mixture of the two isomers.

More detailed studies had been carried out by d’Aguiar [14] who checked the

results previously found. He isolated the following naphthalene derivatives :

two dinitronaphthalenes α and β (see p. 427)

three trinitronaphthalenes α,β and so called δ (see p. 431)

and two tetranitronaphthalenes α and β (see p. 434)

Beilstein and Kuhlberg [15] and Beilstein and Kurbatov [16] reinvestigated the

methods of preparation and properties of dinitro derivatives of naphthalene and

obtained a new product, γ− trinitronaphthalene.

The constitution of α−, γ− and δ− trinitronaphthalenes as well as of β−, δ− and

γ− tetranitronaphthalenes has been determined by Will [17]. Friedländer [18]

extended these investigations on β− trinitronaphthalene.

However, Dimroth and Ruck [18a] found that some of Will’s data required

correction: 1,2,5-trinitronaphthalene ( δ according to Will’s annotation) does not

exist and δ− tetranitronaphthalene possesses the structure 1,4,5,8- and not 1,2,5,8,-

as Will suggested.

The conditions under which mono-, di-, tri- and tetra-nitronaphthalenes are

formed were investigated in detail by Patart [19] in extensive experimental work.

By applying similar conditions (temperature and time) for the nitration of naph-

thalene with various nitrating mixtures, Patart determined the compositions of

the products (the number of nitro groups) from the pressures they produced in

a manometric bomb. The pressures, produced by pure substances were known,

viz. :

nitronaphthalene (MNN) 927 kg/cm^2

dinitronaphthalene (DNN) 2296 kg/cm^2

trinitronaphthalene (TNN) 3280 kg/cm^2

tetranitronaphthalene (TetraNN) 3793 kg/cm^2

Similar experiments were carried out with the products of nitration of dinitronaph-

thalene.

Later Sapozhnikov [20] used Patart’s data [19] for his triangular diagram,

representing nitration of naphthalene (Figs. 104). In Fig. 105 and 106 the nitration

curves for naphthalene and dinitronaphthalene are shown (Pascal [21]).

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