Presented for the Degree
of
Doctor of Philosophy
at the
Johns Hopkins University
by
C. Willard Hayes,
1887.
Contents.
p.
Introduction 3.
I Ortho-sulpho-benzoic acid.
Preparation from toluene and H_{2}SO_{4} 7.
” ” para-nitro-toluene and H_{2}SO_{4} 8.
Oxidation of toluene-o-sodium sulphonate 12.
Preparation of Sulphinide from ” ” 14.
” ” ” by chlorsulphonic acid. 17.
Conversion of sulphinide into o-sulphobenzoic acid. 25.
Analysis of and crystallography of ” ” ” 28.
II Sulphonfluoresceïn--previous attempts 29.
Preparation and purification of s-fluoresceïn 30.
Analyses of ” 34.
Properties of ” 35.
Salts. Ba. and Ca. of ” 37.
Acetyl derivative of ” 41.
Br substitution products of ” 42.
Action of H_{2}SO_{4} on ” 44.
Action of HCl on ” 45.
Reduction of ” 46.
Conclusion. 47.
On Sulphonfluoresceïn and some of its Derivatives.
Introduction.
The close analogy in composition and structure between phthalic acid
and ortho-sulpho-benzoic acid suggests the possibility of obtaining
from the latter, by its action on phenols, substances analogous to
the phthaleïns. If such compounds could be made they would afford
a favorable opportunity of studying the effects produced in the
properties of a compound by the replacement of CO by SO_{2}. It was
with a view to such study that the following discussed work was
undertaken at the suggestion of Prof. Remsen and carried on under his
constant guidance.
Some experiments previously performed by Remsen and Palmer (A.G.)
indicated the possibility of the formation of a fluorescent substance
by the action of ortho-sulpho-benzoic acid on resorcin but they did
not succeed in obtaining any definite crystallized compound from the
reaction.
The chief obstacle to be overcome in the work is the difficulty in
obtaining the o-sulpho-benzoic acid and a large proportion of the
work here described was applied in that direction.
Ortho-sulpho-benzoic acid: Methods for its preparation.