The Chemical Constituents of Piper Methysticum: Or, The Chemical Constituents of the Active Principle of the Ava RootBall, Alice A.
Science
The Chemical Constituents of Piper Methysticum: Or, The Chemical Constituents of the Active Principle of the Ava Root
Ball, Alice A.
Kava plant
Wt. of dish 12.8825 12.8826
Wt. of dish and substance 13.0060 13.1310
Wt. of substance .1235 .2484
Wt. of dish and silver 12.9400 12.9980
Wt. of silver .0575 .1154
Neutralization equiv. 125 125.3
Using the same sample, a neutralization equivalent was obtained by
titration with standard NaOH.
Wt. of substance .0912
N/10 NaOH 7.25cc
Neutralization equiv. 125.8
The above data shows that the sublimate is a mixture. No empirical
formula can be calculated from the combustions, and different samples
give different neutralization equivalents although the duplicate
determinations on the same sample showed good agreement thus
demonstrating the reliability of the methods.
By fractional sublimation it was possible to obtain fractions with
different melting points. The first sublimate melted sharply at 109
degrees. From the last fraction it was possible to separate some
crystals that melt at 200 degrees Centigrade. These might possibly be
p-acetyl-benzoic acid, as its properties of solubility, crystalline
form, its melting point and power of sublimation agree with those of
p-acetyl-benzoic acid.
Those crystals that appeared identical with benzoic acid were placed
in a melting point tube, and some known benzoic acid (from toluol)
was placed in another tube. These two tubes were placed in the same
sulphuric acid container and their melting points taken at the same
time. They melted at the same temperature.
The sublimate had a very pleasant aromatic odor resembling benzoin.
It gave no coloration with ferric chloride, thus eliminating a large
group of aromatic compounds. Some of the crystals were found to be
identical with benzoic acid when examined under the microscope.
The characteristic odor of methyl benzoate was produced when a
small quantity of the crystals were heated with methyl alcohol and
concentrated sulphuric acid. On treating some of the carefully
neutralized product with ferric chloride solution, a flesh colored
precipitate was formed. It agreed closely in its analysis with the
precipitate formed with known benzoic acid.
The filtrate left after the removal of the iron precipitate was
acidified and extracted with ether, and the ether removed by
evaporation. The resulting substance decolorized alkaline permanganate
solution, but did not decolorize bromine water. When the leaflet
needles that melt at 200 degrees were mechanically removed from the
original sublimate, the substance left after precipitating with ferric
chloride melted at 109 degrees. When these crystals were not removed,
the melting point of this material was not definite, but was over a
range of five degrees, from 110 to 115 degrees Centigrade.
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