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REACTIONS WITH AMINO AND AMIDO COMPOUNDS 215
X solid organic peroxide is formed by the joint reaction of formaldehyde,
urea, and hydrogen peroxide in the presence of acid* 1 .
Diamines, Reactions of formaldehyde with diamides of dibasic organic
acids, such as oxarnide, malonamide and suecinamide, are similar to the
reactions which take place with area. In general, however, these diamides
show much less capacity for rapid polycondensation and resin formation
than urea.
Dimethyloloxamide was prepared by Bougault and Leboucq 9a in connection
with an analytical study of rnethylol derivatives, and is apparently
readily formed by the action of formaldehyde on oxamide.
Malonamide, since it possesses a methylene group activated by two adjacent
earbonyl groupings, is able to react with three mols of ioimaldehyde
and yield compounds which are believed to be polymers of the trimethylene
derivative indicated below 19 :
r CONIOHJ"
/
H3C:C
L CONXHIJB
Resins which apparently correspond to this formula may be obtained by
boiling down mixtures of malonamide and formaldehyde solution in the
presence of either alkaline or acidic catalysts.
By reacting suecinamide with formaldehyde solution in the presence of
potassium carbonate.. Einhorn and Ladisch 32 obtained a dimethyjolsucclnamide
melting at 167 D C, with decomposition.
Resinous products have been obtained by reaction of a wide variety of diand
polyamides and sulfamides with formaldehyde 119 . Polysulfonamides
also give resins on heating with formaldehyde and acids 11 .
Polyureas such as propylene diurea, NHaCONH(CHa)^HCONH2f are
reported to form both mono- and dimethylol derivatives on reaction with
fonnaldehyde solution at pH values of 7.0 to 7.4 1S .
Reactions of the cyclic ureideT hydantoin, with formaldehyde have been
studied by Niemeyer and Eehrend 80 . Monomethylolhydantoin is obtained
by heating hydantoin with formaldehyde solution for a short time.
Its exact structural formula has not been determined; two isomeric possibilities
exist:
0:C
-N—CHaOH
\
CrO or
-NH
HtO—NH
\
Mo nomethylolhydantoin
/
0:C—N-CHjOH