534
I N D U S T R I A L AND ENGINEERING CHEMISTRY
Vol. 17, No. 5
Galones per N/;/hqram
0 DAYS 10 0 HOURS /X2& Figure 9-Curve
20
30
2x240
3x240
40 4x240
50 5x240
60 6x240
70 7x240
80 8x240
90 9x240
100 10x240
Showing Response i n Basal Metabolic Rate to Adrenaline Expressed i n Hours a n d t o Thyroxin Expressed i n Days (Boothby and Sandiford)
present time, but it seems probable that the oxidizing power of adrenaline in the form of its ketone is brought about by the forma-
n
tion of the c-c-x- group. That the two hydroxy1 groups on the benzene ring are involved is also indicated, but a p w ently they are not indispensable. The application of this hypothesis to other substances is very inviting and the reactions of bios described by Eddy and his
co-workers led me to suggest, in discussing Eddy’s paper a t the December, 1924, meeting of the A. A. A. S., that the structural formula agreeing with his empirical formula of C5HllOaN is ~ . ~ y d r o x y ~ ~ y ~ a m ~ n oacid. v a ~ e In r ~ c this compound oxida-
tion of the hydroxyl group to aldehyde
be followed by enoli-
n
zation with the amine group and the formation of the C-C-Xlink. I am a t present testing this hypothesis.
Detection of Diethylphthalate in Perfume’ By Frederick Breithut and P. Max Apfelbaum THECOLLEGE OF THE CITYOF NEWY O R KSEW , YORK,N. Y .
-4LEIGH and Marie2 report that the official test for the detection of diethylphthalate in ethyl nlcohol “has been found by the writers to be unreliable, as a distinct fluorescence will develop with grain alcohol known to be free from diethylphthalate.” ,4s diethylphthalate is one of the denaturants the use of which is permitted in the manufacture of perfumes (Formula 39-B, specially denatured alcohol), the reliability of the test for diethylphthalate is sometimes a matter of importance. This truth was brought forcibly to the writers’ attention in n recent court case. One of the points a t issue was whether or not diethylphthalate was present. Blank tests showed that the official test for diethylphthalate is unreliable. A marked fluorescence develops even when diethylphthalate is absent. These results therefore agree with the*fidings of Raleigh and Marie on this point. By replacing resorcinol with phenol, however, a substitute test was developed which was found to be reliable, not only with grain alcohol alone, but also with perfumes. The following gives the technic of the modified test as the writers used it with perfumes: 1 2
Received March 2, 1925 J . A m . Chem. Soc , 41, 599 (1925)
Ten cubic centimeters of the perfume were treated with a saturated solution of sodium chloride and the resulting mixture was centrifuged to remove the oil layer. The water layer was then placed in a distilling bulb, 5 cc. of sodium hydroxide (10 per cent solution) added, and the mixture distilled. (The distillate was used for other tests.) The residue from this distillation was then evaporated on the steam bath, and finished just to dryness on a hot plate. The dry residue was mixed thoroughly, when cooled, with an equal amount of phenol. A portion of this mixture was treated with five or six drops of concentrated sulfuric acid and kept a t 160” C. for 3 minutes. One cubic centimeter of water was added to the fused mass, which was then made alkaline with dilute sodium hydroxide solution. A pink color, discharged on making the solution acid and re-appearing on making it alkaline again, indicates the presence of phenolphthalein in the mixture, and therefore the presence of diethylphthalate in the original substance.
Blank tests employing all of the reagents used in making this determination, individually and in all possible combinations, gave negative results in all cases. When diethylphthalate itself, or mixtures containing this substance were tested in exactly the same manner, positive results were obtained in all cases. The method is therefore considered reliable and can probably be used in testing for diethylphthalate in mixtures other than perfume.
