On Sulphonfluoresceïn and Some of Its DerivativesHayes, C. W. (Charles Willard)
Science
On Sulphonfluoresceïn and Some of Its Derivatives
Hayes, C. W. (Charles Willard)
Sulfonefluorescein; Thesis (Ph. D.)
Several attempts had already been made to obtain from the action
of o-sulphobenzoic acid and resorcin a substance analogous to the
fluoresceïn obtained by Baeyer[1] from phthalic anhydride and
resorcin but while a strongly fluorescent substance was easily
obtained, no definite compound could be separated from it. Thus
Palmer obtained, by heating together the above named substances to
160°(?) a solid mass, part soluble in water and part insoluble as a
dark brown amorphous powder. Both parts gave a strong fluorescence
with alkalis. He was unable however to obtain the substance itself or
any derivative in a crystalline form.
[1] Annalin. No. 183. S. 1. No. 202. S. 36 & S. 153.
Berichte. No. IV. S. 457. 555. 658. 662.
” ” VIII. S. 66. 146.
The first experiments in this series gave the same negative results.
The mixture of acid and resorcin was heated in a sulphuric acid
both for several hours to 150°-170°, and as it showed no sign of
solidification the temperature was raised to 200° and then to 235°
where it was kept several hours longer. The black viscous mass
obtained in this way became vitreous on cooling, and in all respects
resembled that described by Palmer. This however is not the normal
course of the reaction as shown later but is probably due to a
decomposition of the normal product produced by too high heating.
An experiment was made with the acid salt of ortho-sulphobenzoic acid.
COOH
╱
C_{6}H_{4}
╲
SO_{2}OK,
resorcin and H_{2}SO_{4} heating the mixture to 150°-170°. A solid
black mass was obtained strongly fluorescent in alkaline solution and
in all other respects like the substance obtained above.
Preparation of Sulphonfluoresceïn.
As the result of a number of experiments the following method of
preparing and purifying the sulphonfluoresceïn was found to give the
best results.
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