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HBXAMETH YLEKBTETRAMIXE 291
alcoholic iodine solution on a water solution of hexamethylenetetramine,
whereas the latter is produced when an excess of alcoholic iodine is added to
hexamethylenetetramine in alcohol. Hexamethylenetetramine tetraiodide
Is also formed by the addition of excess iodine-potassium iodide to aqueous
hexamethylenetetramine solution. Scheuble" reports that a hexamethylenehexaniiuehexaiodide
(CeH^Xele) maybe prepared by addition of nitrogen
iodide to hexamethylenetetramine or by the joint reaction of ammonia,
iodine, and hexamethylenetetramine:
C6Hi2X4 + 2XIS -> CftHiaXJi
C6H13X4 + SXHB 4- eis -*• CeHiaNM, + 6XHJ
This product is a violet-red powder which explodes on heating or sudden
shock, but this can be avoided by mixing it with an Inert material such as
talc.
}Iixed halides such as CeHioXJCl 59 are produced by the action of halogen
compounds on hexamethylenetetramine.
Inorganic halides such as phosgene form addition compounds with hexamethylenetetramine.
The phosgene compound has the composition
2C«HisN4-COCls, and melts at 187-190 °C M . A mixture of caustic soda,
phenol, glycerin, and hexamethylenetetramine in water solution was used
in World War I for the neutralization of phosgene {page 334). "With sulfur
chloride, hexamethylenetetramine gives the addition compound 2C6Hi2-
Xi-SsCla 11 -.
Addition Compounds with Inorganic Salts. Hexamethylenetetramine
forms addition compounds with a wide variety of inorganic salts including
salts of alkali metals, alkaline earths, rare earths and metals. Although
many of these compounds tend to conform to the type formula, IM X„- nC&-
HiaXi, in which M stands for a metal ion of valence n, the number of molecules
of combined hexamethylenetetramine per mol of salt is often lower
than this value and several different complexes are often formed with the
same salt.
Lead is reported to be almost unique in not forming compounds of this
type, basic lead nitrate and chloride being the principal products formed
when aqueous hexamethylenetetramine solutions are reacted with lead
nitrate and lead chloride, respectively 38,87 . Complexes are reported with
salts of lithium, sodium, potassium, copper, silver, gold, magnesium, calcium,
strontium, barium, zinc, cadmium, mercury, aluminum, titanium,
lanthanum, cerium, neodymium, yttrium, erbium, thorium, tin, antimony,
bismuth, chromium, molybdenum, tungsten, uranium, manganese, iron,
cobalt, nickel, platinum, and palladium 3 ' 10 .
Illustrative of the metallic salt complexes are the compounds formed with
silver nitrate, mercuric chloride, and the chlorides of tin. When a mod-