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
The product or “bake” appears as a hard grayish mass, slightly porous.
It is dug out, pulverized, boiled up in a large evaporating dish,
containing water and a little (10cc.) hydrochloric acid, with animal
charcoal and filtered. The solution should be almost colorless. The
effect of the slight amount of hydrochloric acid was accidental; the
first solutions were always a deep red color due to some of the red
dyestuff seeming to be present, and the longer the solution was boiled
the redder it got. A little acid seems to prevent this entirely. The
solution is evaporated on a water bath until a scum has formed on the
surface when it is allowed to cool and crystallize. It crystallizes in
small almost white needles, which appear to fill the entire liquid;
this is deceptive as on filtering the bulk is considerably reduced.
They fall to a powder when they are dry. If they are colored red or
pink they are washed while still on the filter with water; alcohol does
not remove this color.
The acid as formed has no melting point, but chars and decomposes on
heating. A sample was tested for nitrogen and sulphur with very good
positive results. On fusion with caustic soda and acidification of the
product a positive reaction was obtained on the addition of bromine
water as is customary with phenols.
It was identified as identical with the acid of Nevile and Winther
(loc. cit.) by conversion thru the diazo compound into dinitro ortho
cresol, melting at 85.8 as described under the description of the diazo
compound.
SULPHONATION OF PARA TOLUIDINE
Metcalf, (loc. cit.), gives a method for the preparation of the
sulphonic acids of para toluidine, and states that both the possible
acids are formed, with the meta position (referred to the methyl
group) in good yield. Schultz and Julius, (“Farbestoff Tabellen”,
1894 Edition, Trans, by F. C. Green), and Nevile and Winther, (loc.
cit.), say that the sulphonation of para toluidine gives a mixture of
the sulphonic acids, with the ortho (referred to the methyl group)
sulphonic acid in a much greater yield. As the sulphonation of para
nitro toluene gives (Dissertation, R. S. Norris, BPL. 5976.109) a
ninety-five per cent yield of the ortho sulphonic acid, it would seem
as though the amino compound should give a large yield of the acid
(sulphonic acid group ortho to the methyl group,) and such was found to
be the case.
Public-domain text, read in full here on John Shaqi.
Reviews
Reviews
No reviews yet
Be the first to share your thoughts on this work.
Join the Discussion
Join the discussion
Sign in to leave a comment or review.
Sign InorCreate an account