33 2 
Journal of Agricultural Research 
Vol. XXVI, No. 8 
residue was then warmed gently with concentrated hydrochloric acid for 
a few minutes and cooled. On adding the Kreis reagent a brownish-red 
color developed almost immediately, the color deepening somewhat and 
becoming more frankly red on standing. 
The main portion of the chloroform solution was transferred to a 
distilling flask and subjected to vacuum distillation for the removal of 
the chloroform. The residue was a clear, thick, glassy sirup, similar in 
appearance to the oleic acid ozonid described by Harries and Thieme 
( 38 ). It gave off a penetrating odor, strongly suggestive of rancid fat, 
and- liberated iodin from potassium iodid in the presence of dilute acetic 
acid. 
From the above experiment it would appear that neither the ozonid 
itself nor its usual hydrolytic products, i. e., the C 9 saturated aldehydes 
and acids, respond to the Kreis test; but that on contact with concen¬ 
trated hydrochloric acid it may experience a different kind of decompo¬ 
sition with the formation of a compound that yields a red condensation 
product with phloroglucin. A possible connection between the presence 
of active oxygen and the odor of rancid fats is also suggested. 
Examination of the ceeavage products of oeeic acid ozonid.— 
The isolated oleic acid ozonid was hydrolyzed by heating on the steam 
bath for 30 minutes with 75 cc. of water, the heating being continued 
until the ozonid, which is heavier than water, had been completely 
transformed into products lighter than water. The mixture was shaken 
with ether and the aqueous phase drawn off, after which the ethereal 
solution was shaken with an aqueous solution of sodium bicarbonate, 
which, according to Harries and Thieme (38), should remove most of the 
azelaic acid and azelaic half-aldehyde. The study of the sodium bicar¬ 
bonate solution yielded no interesting results and will not be reported. 
The material remaining in the ether was recovered by drying the ether 
solution over anhydrous magnesium sulphate and distilling off the ether 
at a somewhat reduced pressure. The residue was then subjected to 
fractional distillation at a pressure of about 0.5 mm., fractions being 
collected between 8o° and no° C. and between 120° and 150° C. An 
undistilled residue remained. 
The water separated from the cleavage products immediately after 
hydrolysis was examined for peroxid, the presence of which was indi¬ 
cated by an immediate separation of iodin when a few drops of the liquid 
were added to a neutral solution of potassium iodid. The Kreis test was 
not applied until the following day, when a deep gold color with a 
suggestion of pink was obtained with phloroglucin-hydrochloric acid. 
The fraction collected between 8o° and no° C. in the vacuum distilla¬ 
tion, which should have contained the nonylic aldheyde, amounted to 
not over 1 cc. It gave a fairly strong peroxid reaction with potassium 
iodid in the presence of acetic acid, the acetic acid having been added for 
solvent purposes. It also gave a good test for aldehydes with decolor¬ 
ized fuchsin and a good Kreis test. 
The fraction collected between 120° and 150° C. amounted to about 
2 or 3 cc. It was probably composed principally of nonylic acid. It 
gave a positive test for aldehydes with Schiff's reagent, a weak peroxid 
test, and a weak Kreis test. 
From the above-mentioned results it would appear that in the hydroly¬ 
sis of oleic acid ozonid small amounts of products other than C 9 aldehydes 
and acids may be formed, and in particular a compound capable of form- 
