Meta toluene sulphonic acid and related compounds — John Shaqi
Meta toluene sulphonic acid and related compoundsAllen, C. F. H. (Charles Francis Hitchcock)
Science
Meta toluene sulphonic acid and related compounds
Allen, C. F. H. (Charles Francis Hitchcock)
Organic compounds -- Synthesis; Sulfonic acids
As the brownish powdery substance was mixed with the flat crystals
produced above, a method had to be found to separate them and purify
each. I screened them as much as possible with good results. I
removed the last of the fine powder by dissolving it off with hot
water. Metcalf said that they could be separated by their difference
in specific gravity in fifty per cent alcohol but this method was
unsuccessful. I boiled up the aqueous solution of the powdery substance
with animal charcoal, filtered and evaporated to crystallization.
Square, flat, white crystals were obtained identical in all but color
with those mentioned above. They are soluble with difficulty in cold
water, readily in hot, and insoluble in alcohol. In these properties
and in appearance they compare to the ortho sulphonic acid of para
toluidine as made and described by Parks, (Dissertation, 1892).
Metcalf and Nevile and Winther say that the meta sulphonic acid of
para toluidine forms needles, but I obtained nothing that could in any
way be called needles. This sulphonic acid had no melting point, but
charred and decomposed. A test for elements showed nitrogen and sulphur
to be present. The aqueous solution had a strong acid reaction to
litmus.
In order to see if this might be the desired acid I tried to prepare
an acid chloride with phosphorus pentachloride in the usual way, and
then intended to convert it into the amide and get a melting point
for identification. I used equal weights of the acid and phosphorus
pentachloride. I ground them together at ordinary temperature in
a mortar: no result. I heated it on a water bath: no result. I
heated it on a gauze over a flame: no result except decomposition and
carbonization. However I poured water into the mixture and decomposed
the excess of phosphorus pentachloride, and filtered. A gummy brownish
mass remained which was insoluble in all reagents tried, (methyl
and ethyl alcohol, benzine, petroleum ether, (40-60), water, carbon
tetrachloride, dilute hydrochloric acid, acetone, and acetic acid.)
Ethyl ether extracted a very small amount, just enough to color it
yellow, and leave a yellow color on porcelain on evaporation, but
not enough to make a study of the properties. On shaking up with
concentrated ammonia the mass became very finely divided, but no
solution appeared to take place; on filtering and evaporating to
dryness there was no residue.
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