urbaf2

NITRO DERIVATIVES OF HIGHER BENZENE HOMOLOGUES 413

of water, is dried in tunnel or chamber driers at 60-70°C, until the water content

falls to 0.1%. This operation takes 12-24 hr, depending on the type of drier. The
finished product is a crystalline, slightly yellow powder.

NITRO DERIVATIVES OF OTHER HOMOLOGUES

OF BENZENE

NITRO DERIVATIVES OF MESITYLENE

Trinitromesitylene is of some importance as an explosive due to the fact that

the raw material - mesitylene -is easily obtainable by reacting acetone with sul-

phuric acid (Kane [21]).

However, as Tishchenko [22] reported, the yield of the reaction did not exceed

27% of the theoretical. Ipatiyev [23] found that mesitylene could be obtained in

a yield up to 36% by reacting acetone with hydrogen chloride at a pressure of

100 atm.

Sucharda and H. Kuczynski [24] found that the yield could be increased to 47%

by reacting the two compounds in sealed tubes at 145-195°C.

Cahours [25] obtained trinitromesitylene by treating mesitylene with a mixture

of nitric and sulphuric acids. Repeating these experiments, A. W. Hofmann [26]

obtained dinitromesitylene as well.

Nitration of mesitylene to di- and tri-nitromesitylenes proceeds with great

ease :

m. p. 89°C m. p. 235°C

Dinitromesitylene can be obtained by dissolving mesitylene in fuming nitric

acid, followed by the addition of water which causes dinitromesitylene to precip-

itate. For the preparation of trinitromesitylene by the Blanksma [7] method,

mesitylene is dissolved in sulphuric acid (partial sulphonation taking place), and

the solution is added to nitric acid (sp. gr. 1.52). Trinitromesitylene then precipi-

tates, as white crystals, dissolved by organic solvents only with difficulty. Kholevo

[26a] nitrated mesitylene with the nitrating mixture (27% HNO 3 , 69% H 2 SO 4 ,

4% H 2 O) to yield trinitromesitylene.

The explosive power of trinitromesitylene is rather low - of the order of DNT.

Its sensitiveness to impact, however, is relatively high - of the order of TNX -and

much higher than that of DNT. This can be explained by the presence of the largest

possible number of substituents on the ring.