On Sulphonfluoresceïn and Some of Its Derivatives — John Shaqi
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.)
Calculated for C_{19}H_{10}Br_{2}O_{6}S = 30·42% Br.
These results, though not conclusive, indicate that under the
given conditions it is the di-bromsulphonfluoresceïn which is
formed. Whether this is due to the presence in the compound of the
SO_{2} group or simply to the greater insolubility of the di-than
of the tetra-brom product cannot be definitely stated. When the
original acetic acid mother liquor was evaporated to dryness, a red
non-crystalline substance remained which more closely resembled rosin
than the crystals. The concentrated alkaline solution had a deep red
color without fluorescence and acted as a red dye stuff. The dilute
alkaline solution showed the characteristic delicate pink of rosin.
Action of H_{2}SO_{4} on S.fluoresceïn.
A test tube in which S.fluoresceïn was being made just at the end
of the reaction broke and allowed the contents to run out into the
sulphuric acid bath, which had a temperature of 175°. On standing
several days the solution deposited a heavy precipitate which was
separated by filtering through glass wool. When dry it formed a light
yellow powder extremely soluble in water, alcohol and ether.
The alkaline solution had an intense green fluorescence with
delicate shades of pink by transmitted light. On account of its
great solubility it was impossible to purify it by crystallization,
hence the Ba salt was made. The substance decomposed BaCO_{3} with
great ease forming an easily soluble salt. When it was attempted to
evaporate the solution of this salt to crystallization the latter
came out in a hard insoluble granular form and on continuous boiling
of the solution turned brown. To avoid this undesirable form it was
converted into the Ca. salt by treatment with H_{2}SO_{4} and then
CaCO_{3}. This also formed a hard granular insoluble mass on boiling
but did not change in color. As there was no guarantee as to its
purity and only a small quantity was obtained it was not analyzed.
Action of HCl on S.fluoresceïn.
Hydrochloric acid does not dissolve S.fluoresceïn but converts it
into a light yellow granular powder. When recrystallized from water
in which it is quite easily soluble it melts partially at 130°
apparently with some decomposition. This compound was not further
studied.
Reduction of S.fluoresceïn.
When treated with zinc dust in a strong alkaline solution
sulphonfluoresceïn is reduced to a colorless substance probably
analogous to fluoresceïn which is formed in the same manner. On
account of its great solubility it could not be obtained in the free
state. It is quickly oxidized to s.fluoresceïn by oxidizing agents
as KMnO_{4} and HNO_{3} and passes back spontaneously on standing in
the air. The latter action is however much slower than in case of
fluoresceïn.
Conclusion.
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