INDUSTRIAL AND ENGINEERING CHEMISTRY
1218
chromogen generally, but the amount was variable. Similar results were obtained with wheat germ oil and cottonseed oil. TABLD IV. DISTILLABILITY OF CHROMOGEN FROM OILS
Oil a-Tooopherol due) (corn oil resiSoybean (crude) Soybean refined) Soybean [refined) Cottonseed (Wesson) Wheat germ (crude)
Tocopherol in Oil before Distn., T Mg. ture, 102.1 107.0
Distillate
180 170 210 240
99.5 43.4 45.7 53.4
Residue
~ ~
~o
in Dist.
59:2
97.5 40.9 43.2 61.1
65:4
86.8 64.5
180 180
44.4 57.0
9:o
50.9 88.3
48.2
180
38.2
13.4
80.0
193.0
180 240
155.2 12.0
5i:4
80.3 6.2
.
0-
~~
-
~
~
~
$
The authors are indebted to Lever Brothers Company for a grant in support of this work. The synthetic tocopherol was kindly furnished by Merck & Company.
Literature Cited (1) Furter, M., and Meyer, R. E., Helv. Chim. Acta, 22, 240 (1939). (2) Hickman, K. C. D., IND. ENG.CHmf., 29, 968 (1937). (3) Ibid., 32, 1451 (1940). (4) Hickman, K. C. D., and Gray, E. LeB., Ibid., 30, 796 (1938). (5) Olcott, H. S., J. B i d . Chem., 110, 695 (1935). (6) Quackenbush, F. W., Gottlieb, H. L., and Steenbook, H., abstracts of papers, Div. Agr. and Food Chem., A. C. S., S t . Louis, 1941. (7) Rawlings, H. W., Oil & Soap, 16,231 (1939). ( 8 ) Riemenschneider, R. W., Swift, C. E., and Sando, C. E., Ibid., 17, 145 (1940). (9) Ungnade, HeE., and Smith, L. I,,J . Org. Chem., 4, 397 (1939). P R ~ ~ ~ N Tbefore E D
the Division of Agricultural and Food Chemistry a t the 1Olst Meeting of the American Chemical Sooiety, St. Louis, Mo. Published with the approval of t h e Director, Wisconsin Agricultural Experiment Station.
F :" -
-
---
-
1LO
4-
-
--
-5
-
9.-
+
/o- 0
-- 6 -
Jaturuted So/ution~ o f 0 &So,
Y
-4
/&p-: e
Le! --*% .
--20- -
-I
27
tocopherols occur naturally in part as the esters. However, upon saponification of the undistillable residue, we have been able to recover only a small percentage of the chromogen in the unsaponifiable fraction. Its true nature must await further experimentation.
Acknowledgment ~ M g . Tooopherol ~ ~ in:
C.
We know very little concerning the nature of this residual chromogen. The color produced with nitric acid was not a pure but it Was not to exclude the presence of tocopherol in some quantity. It is possible that the color was due to tocopherol esters, and that they were sufficiently nonvolatile to resist distillation under the conditions used. Olcott (6) also expressed the view that
25
Vol. 33, No. 10
1
--
0 KC/-
N o 4 -o-o>oc/
/--
0 CSCI
-- -.-
'
OR saturated aqueous solutions of potassium and sodium sulfates and of potassium, sodium, and cesium chloride, Foote, Saxton, and Dixon' presented equations connecting the vapor pressure, p , in mm. of mercury, with the temperature, T, in degrees Kelvin, The equations for the sodium and potassium chloride solutions are, respectively, logp = logp =
--2890'7 T - 4.715 log T + 22.612
- 2995*5 _ _ - 6.680 log T + 0.001024 T f 27.569 T
$1 -
1
-
(2)
The equations for the other solutions are of the form, logp-
e--/o
--84 --8
(1)
- pA+ B
(3)
The line coordinate chart facilitates calculation of vapor pressures, once equations of the form of Equation 3 are d e termined for solutions of sodium and potassium chlorides. Values of A and B are as follow:
9: > 6
-
Satd. Soln.
A
KzSOd
2332.5 2258.0 2306.0 2198.5 2696.6
KC1 NaCl CSCl NaiSOi
-
---
B 9.1881 8.8750 8.9850 8.5621 10.3630
The index line on the chart shows that the vapor pressure
of a saturated aqueous solution of sodium sulfate is 10 mm. of mercury at 15' C. 1 Foote.
(1932).
H. W., Saxton, B., and Dixon, J. K., J . Am, Chem. Soc., 54, 563
