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2SS FORMA LDEH YDE
base or ?JV :he action of hydrogen chloride on a hot solution in absolute
alcohol-. According to Butierov, it melts at 1SS-1S9°C. By the action
of excess hydrogen chloride, a compound having the composition CeHiaX4.
2HC1 is formed^. This product is believed to be a molecular compound of
hydrogen chloride and the neutral salt. When a solution of hexamethylenetetramine
ir_ cold hydrochloric acid is saturated with hydrogen chloride,
dichloromerhyi ether is obtained 107 .
The sulfate o: hexamethylenetetramine. (CeHiaXOa-HaSO^ is precipitated
by the action of sulfuric acid on hexamethylenetetramine in cold
alcoholic *oh::ion :7 " 8 . It is acid to phenolphthalein but not to methyl
orange.
Salts oi hexamethylenetetramine and many other inorganic acids including
the hydrobromic^, CeH^Xi-HBr, 4 ' 50 , the hydroiodide, CeHisX^-
HP, the phosphates, C5Hi2X4 - HaP04 S7 and SCeH^X^GHaPO^OH^ 50 ^.
the perclilorare. C'eHi*X4 • HCI04 S5 < and the explosive chromates, 2C6H12X4-
HsCrsOr and 2CeHuXV HaC^O!* 17 - 36 , have also been reported.
According to Del^pine 28 and other investigators 17 , a mononitrate of hexamethyleneieiramine
may be obtained by the action of nitric acid on an
aqueous solution of hexamethylenetetramine at 0°C. With more concentrated
acid a dimtrate, C6H12X-2HX"GS (m.p. 165°C), is produced 5 -' 37 .
Hale 5 ' prepared this product in S2 per cent yield by gradual addition of
C.P. nitric acid density = 1.42) to a 25 per cent solution of hexamethylenetetramine
a T G"C\ The precipitated salt may be separated from acid by
filtration Through glass woo] and dried after washing with cold 50 per cent
ethyl aleohoi and ether. It is readily soluble in water at room temperature
but gradually decomposes when the solution is allowed to stand. The
solution is acid and the total combined acid may be determined by titration
with alkali. IT is insoluble in alcohol ether, chloroform, and carbon tetraeiiloride.
With dilute nitric acid, 70 per cent or below, Hale states that the
hydrolysis reaction predominates and little salt formation takes place.
Xitratiort. When treated with concentrated nitric acid (95-100 per cent)
at low temperatures, hexamethylenetetramine is nitrated giving the explosive
cyclonhe, cyciotrimethylenetriuitramine (m.p. 202°C) . 3 - >52 (Cf. Chap.
XX, page 330 , shown below:
/ \ H,
/ \ C
X X / \
\ / \ OsX—N X—XOs
CHS CHsl -f 4HXOs \ j -h3CH,0 4-XH*2CO«
\ / \ H2C CH*
* I \ /
I CHS X
\ CH,/ [
\ I / NO,
X