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 action of methyl, ethyl, and n-propyl alcohols on diazo compounds
has been well studied by the above authors, and it has been shown that
the first two at ordinary pressures give the alkoxy reaction either
in whole or in part; n-propyl alcohol gives the hydrogen reaction
only. Also the first two give the hydrogen reaction in the presence
of zinc dust or sodium carbonate, but in these cases form salts of
the acid. On account of its rarity n-propyl alcohol was not used, but
n-butyl alcohol which is available in large quantities and in a pure
condition was employed. Recent advances in fermentation as applied
to organic chemistry have made this substance easily obtainable as
a byproduct in the production of acetone which was needed in large
amounts during the late war. Its use was found to be successful; it
boils at 117 and so can be easily distilled off after decomposition has
been effected without a great increase in temperature above the boiling
point of water, which increase Griffin (loc. cit.) showed to cause
carbonization. For this reason i-amyl alcohol although available was
not considered,--also higher alcohols because of this fact and because
of their rarity.
Of the four amino toluene sulphonic acids theoretically possible in
which the sulphonic acid group is in the meta position in reference to
the methyl group only two are commonly known, No. 1, and No. 2.
CH_{3} CH_{3} CH_{3} CH_{3}
/ \ / \ / \ / \
/ \ / \ / \ / \
/ \NH_{2} / \ / \NH_{2} / \
| | | | | | | |
| | | | | | | |
HSO_{3} \ / \ / HSO_{3} \ / NH_{2} \ / HSO_{3}
\ / \ / \ / \ /
\ / \ / \ / \ /
NH_{2}
Methods of preparing No. 1 and No. 2 were found but without details, so
a method had to be worked out to obtain them easily and in good yield.
After a little experimenting No. 1, or ortho toluidine sulphonic acid
was readily obtained in good yield and in a fairly pure condition. No.
2, or para toluidine meta sulphonic acid was obtained in only a ten per
cent yield and by means of a much more difficult method of procedure.
The preparation of this acid was undertaken first and consumed a long
time; Griffin did his work starting with this acid and I hoped to get
as far as he did earlier. It was then available in the market as was
the ortho toluidine sulphonic acid, but now neither are available.
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