urbaf2

436 CHEMISTRY AND TECHNOLOGY OF EXPLOSIVES

Due to difficulties in preparation, tetranitronaphthalenes are not applied as

explosives.

1,3,5,7-Tetranitronaphthalene has been prepared (Chatt and Wynne [35]), by

an indirect method:

(8)

THERMOCHEMICAL PROPERTIES OF NITRONAPHTHALENES

Rinkenbach [36] determined the heats of formation and heats of nitration from

his measurements of heats of combustion of nitronaphthalenes. The heats of com-

bustion of these compounds measured by Badoche [37] are in agreement with the

values reported by Rinkenbach (Table 97).

TABLE 97

HEATS OF COMBUSTION AND FORMATION OF NITRONAPHTHALENES

Nitro derivative

of naphthalene

Heat of combustion

(after Badoche)

at constant volume

kcal/mole

α− Nitronaphthalene

1,5-Dinitronaphthalene

1,8-Dinitronaphthalene

1,3,8-Trinitronaphthalene

1,4,5-Trinitronaphthalene

1190

1152

1154

1118

1121

Hence, the heats of nitration are:

naphthalene to α− nitronaphthalene

α− nitronaphthalene to 1,5-dinitronaphthalene

α− nitronaphthalene to 1,8-dinitronaphthalene

1,8-dinitronaphthalene to 1,3,8-trinitronaphthalene

Heat of formation

(after Rinkenbach)

kcal/mole

-7.15

-5.44

-2.65

+5.7

49.75 kcal/mole

29.67 kcal/mole

31.40 kcal/mole

35.28 kcal/mole