248
VOl. 56
COMMIJTNICATIONS T O THB E D I T O R
Two Pyrex tubes were evacuated and filled simultaneously from a reservoir containing a deuterium-hydrogen mixture. The first tube was fitted with a magnetic break a t the lower end and, after filling, was sealed off a t the upper end. The second tube was equipped with a stopcock and was coated on the inside with a layer of "Lubriseal." At the end of twentytwo days mass spectrographic analysis showed the gas in the first tube to contain 2.07% deuterium and that in the second 2.09yo. It is evident, therefore, that an apparatus containing stopcocks may be used in the study of deuterium-hydrogen mixtures without fear of interchange between deuterium and hydrogen from the stopcock grease.
both 1,2-dimethyltetralin and l-methyl-l-ethylindane appear to be formed. As stated in our initial announcements,' these studies are being pursued in various directions, especially with the object in view of preparing synthetically compounds of biological interest. LABORATORIES OF ORGANIC MARSTON TAYLOR BOGFRT CHEMISTRY DAVIDDAVIDSON COLUMBIA UNIVERSITY RICHARD 0. KOHLIN, JR. NEWYORK,N. Y. RECEIVEDDECEMBER 21, 1933 FREEZING POINTS OF MIXTURES OF THE WATERS, "20 AND H220
Sir: We have determined the freezing points and
FRICKCHEMICAL LABORATORY AUSTINJ. GOULD specific gravities a t 25' on 15-cc. portions of PALMERPHYSICAL LABORATORY WALKER BLEAKNEY mixtures of H220 and H1zO using a Beckmann PRINCETON UNIVERSITY SEW JERSEY PRINCETOY, thermometer calibrated by the Bureau of StandRECEIVED DECEMBER 22, 1933 ards, and standard technique. The samples were
prepared by electrolysis of potash solutions using nickel electrodes, followed by repeated distillations from alkaline permanganate to remove carbon dioxide and other impurities which would Sir : lower the freezing point. The freezing points Since our preliminary publications in this field, were independent of the supercooling (1 to 2.8') a numher of articles have been published abroad2 and were constant to within O.00lo for periods which show that these communications of ours of a t least ten minutes. The zero point of the have escaped notice there and which make i t , thermometer was determined repeatedly against seem desirable to us to report the following addithe freezing point of ordinary distilled water using tional results which have been obtained in our precisely the same technique. Slow freezing of 1aboi.atories. This is done in the hope that i t the 39.9yfisample over a period of three hours will save our fellow investigators the time and with continuous stirring, until one-third had money which might otherwise be spent in the separated as ice, produced no change in equiduplication of experiments. librium temperature greater than the experimental Our studies in the tetralin field, for example, error of 0.002'. The specific gravities of the already have shown that 1-methyltetralin can be melted ice and unfrozen liquid, using a 1.3-cc. obtained by the action of sulfuric acid upon any pycnometer, checked to 0.02%. one of the following : PhCHzCH2CHzCH(OH)Me, These observations indicate that the solid PhCH:CHzCHZCH=CHz, PhCHzCHzCH (OH)Approx. 95 CH2Me, or PhCH2CH=CHCH2Me. heavv ...~ component 1-Et hyltetralin has been prepared similarly 100% = sp. g. F. p., SP. gr. 5 from both Ph(CH2)4CH(OH)Meand Ph(CH2)h- 1.11165 OC. 25/25' isp. g. -1) Observer CH=(:HZ. 1.23 0.053 1 ,001376 3 8 . j Washburn, Sniith and Frandseii, B. S. J . I n two of the above compounds, a shift in the Res., 11, 453 (1933) location of the double bond is indicated in con14.7 .632 1.01644 38..'i This investigation nection with the cyclization. 19.1 ,824 1.02135 38,6 This investigation In the case of Ph(CH2)2CMe(OH)CH2Me, 39.9 1.679 1,04456 37.7 This investigation THE SYNTHESIS OF POLYNUCLEAR HYDROCARBONS BY THE CYCLODEHYDRATION OF AROMATIC ALCOHOLS
(1) (a) Bogert, Sclence, [N. S.] 76, 475 (1932): ( b ) 77, 197 (1933);
( c ) 77, 289 (1933). (2) (a) Schlenk and Sergmann, Chemistry & Induslry, 62, 207 (1933); lb) Cook, Hewett, Haslewood, ?f aE., ibid., 62, 949 (1933); ( c ) Ruzirka, E h m a n n , Goldberg and Hosli, Htlv. Chim. .Acta, 16, 833 (1933); (d) Roo, J . Chem. Soc., 1081 (1933); (e) Cook a n d Hewett, ibid., 1098 (1933); ( f ) Fulton and Robinson, i b i d , , 1463 (1933).
30.5
1,670 1,04411
94.6? 3 . 8
1.1056"
37.9 This investigation; redistilled in vacuo 36. Lewis and Macdonald
The terms specific gravity and density are used interchangeably for this value [Lewis and Macdonald, THIS JOURNAL, 55, 30,58 (1933)l. a
