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
F.C.G. Müller (same as Hubner and Post) made the barium salt of ortho
brom toluene sulphonic acid, and then removed the bromine by treatment
with sodium amalgam. The excess of alkali was removed by sulphuric
acid, the sodium sulphate removed by evaporation and crystallization,
and the residue dried. On treatment with phosphorus pentachloride
an oily toluene sulphonchloride was obtained; this was decomposed
by heating with water, the hydrochloric acid removed by repeated
evaporations, and the syrup thus obtained evaporated to a crystalline
condition. Several salts were made and studied. His amide melted at
90-91. Because this acid differed in properties from the two previously
mentioned, Müller considered it to be the meta toluene sulphonic acid.
About this time F. Gervor (Ann. chem. (Liebig) 169,383), made ortho
diazo toluene sulphonic acid by subjecting ortho toluidine sulphonic
acid to nitrous fumes. This was decomposed with alcohol under
pressure, and a sodium salt of the acid obtained; this was converted
into the chloride and an amide which melted at 148, differing in this
and other properties from the amides of the ortho and para toluene
sulphonic acids previously known.
In 1874 Pechmann (Ibid., 173,195) obtained a quantity of para toluidine
meta sulphonic acid by heating para toluidine with sulphuric acid,
and crystallizing out the para toluidine ortho sulphonic acid and
disulphonic acids, leaving the meta acid in solution because of its
greater solubility. The diazo compound was made by treatment of the
acid in alcoholic suspension with nitrous fumes, and decomposed with
alcohol under pressure. Various salts of the resulting sulphonic
acid were made and studied, also the chloride and amide which melted
"somewhere below 100".
In 1875 Pagel (Ann. chem. (Liebig) 176,297) working on ortho toluidine
sulphonic acid, made a toluene sulphonic acid which resembled Muller’s.
His amide melted at 104.
In 1877 Beckurts (Ber.d.che. Ges. 10, 943), seeking for a good method
of obtaining pure ortho toluene sulphonic acid, heated toluene and
sulphuric acid in the ordinary way, and made the potassium salts of the
resulting acids. By treatment with phosphorus pentachloride he obtained
the acid chlorides which he separated by cooling to -15, and filtering
off the solid para compound. The remaining liquid was transformed into
an amide and purified by fractional crystallization. Two compounds
were obtained with sharp melting points of 153 and 104. From this work
he concluded that the sulphonation of toluene yielded all the three
possible acids.
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