urbaf2

340 CHEMISTRY AND TECHNOLOGY OF EXPLOSIVES

The compound cannot be obtained by direct nitration of trinitrotoluene. It

was first obtained by Holleman [149] from the methyl ether of m- cresol:

(35)

The starting product is nitrated with anhydrous nitric acid (sp. gr. 1.52) to the

trinitro compounds. The methoxy group of the latter, on boiling with ammonia

in methyl alcohol, can be substituted by an amino group.

The trinitro-m-toluidine thus obtained is oxidized in sulphuric acid solution

with potassium persulphate. The yield of this stage of the reaction is about 85%

of theory. The tetranitrotoluene thus prepared may then be recrystallized from

nitric acid of a sp. gr. of 1.40.

Tetranitrotoluene is much more stable than tetranitrobenzene. It is considerably.

more resistant to hydrolytic action of water. At room temperature the presence

of trinitrocresol cannot be detected earlier than 24 hr; at 80°C only 57% of

the product is converted within this period.

Holleman reported the following explosive properties of tetranitrotoluene :

Lead block test

Sensitiveness to impact (2 kg falling

weight)

327 cm^3

50 cm

LITERATURE

1. M. KOSTEVITCH and A. SAPOZHNIKOV in A. G. GORST, ref. [2]; M. KOSTEVITCH, TNT &
   TNB Millard, London, 1919.


2. A. G. GORST, Khimiya i tekhnologiya nitrosoyedinenii, Oborongiz, Moskva, 1940.
   2a. E. Yu. ORLOVA, Khimiya i tekhnologiya brizantnykh vrryvchatykh veshchestv. Oborongiz.
   Moskva, 1960.


3. W. E. GARNER and C. L. ABERNEIXY, Proc. Roy. Soc. A. 99, 213 (1921).


4. F. BENDER AND G. SCHULZ, Ber. 19. 3237 (1886).


5. O. FISCHER and P. HEPP, Ber. 26, 223 (1893).


6. A. G. GREEN and P. F. GRASSLAND, J. Chem. Soc. 89. 1602 (1906).


7. R. PICTET, Compt. rend. 116, 815 (1893).