formaldehyde - Sciencemadness Dot Org

2S6 FORMALDEHYDE
Physiological Properties of Hexamethylenetetramme, Pure hexamethylenetetramine
may be taken internally in small amounts, and is used
in medicine as a urinary antiseptic (page 343). However, it must be
pointed out that toxic action ha.-? been reported in some instances both in
the medical and industrial use of this product. Some persons suffer a skin
rash if they come in contact with hexamethylenetetramine or fumes from
the heated material. It is not entirely clear whether this apparent toxicity
is due to hexamethylenetetramine itself. It is possible that impurities in
the technical material, reaction products formed in industrial use, decomposition
products or hydrolysis products may be responsible. On hydrolysis,
hexamethylenetetramine yields formaldehyde, which would naturally
affect individuals who are sensitive to this aldehyde. However, this is not
the whole story, since in some instances persons who are not sensitive to
formaldehyde itself develop a rash on exposure to hexamethylenetetramine.
In all cases involving toxic symptoms, a physician or dermatologist should
be consulted. In general, methods of treatment involve removal from the
zone of exposure and application of an anti-pruritic.
Chemical Reactions of Hesamethylenetetramine
In general, the reactions of hexamethyleaetetramine fall into two classifications
: Those in which it behaves as a tertiary amine and those in which it
reacts as formaldehyde. Many reactions depend primarily on hydrolysis
to formaldehyde which then behaves in a normal fashion.
Reactions with Inorganic Compoiuids. Hydrolysis and Reduction.
When hexamethylenetetramine is heated with strong acids in aqueous solutions
hydrolysis takes place, with liberation of formaldehyde and formation
of ammonium salts. Reaction is practically quantitative and may be
used for hexamethylenetetramine analysis (page 297):
{CH2)CX4 H- 4EC1 -f- 6H£0 -* 6CH,0 -h 4NH*C1
According to Graymore 48 , a small amount of methj-lamine hydrochloride is
also obtained when hexamethylenetetramine is refluxed for a short time
with excess hydrochloric acid, and larger amounts are obtained with prolonged
refluxing. This is apparently the result of secondary reactions of
the type known to take place when formaldehyde is heated with anmionium
chloride (page 122).
On reduction with zinc dust and hydrochloric acid, hexamethylenetetramine
gives ammonium chloride and trimethylamine hydrochloride as
principal products 25,48 . Varying amounts of methylamine hydrochloride
and in some cases a little dimethylamme hydrochloride were also obtained.
According to Graymore 48 , the reaction mechanism probably involves
formation of trimethylamine and trimethylenetriamine. which then breaks