Improvements in the Manufacture of Preparations of Guaiacol and Creosote.
Year: 1896

page_text: PROVISIONAL SPECIFICATION.
Improvements in the Manufacture of Preparations of Guaiacol and
Creosote.
A communication from abroad by LA SOCIÉTÉ CHIMIQUE DES USINES DU
RHÔNE, anciennement GILLIARD P. MONNET ET CARTIER, of Lyons, France,
Manufacturers.
I, GEORGE BELOE ELLIS of the Firm of J. C. Mewburn and Ellis of 55 and
56 Chancery Lane in the County of London, Chartered Patent Agents, do hereby
declare the nature of this invention to be as follows:-
Guaiacol and creosote, have long been employed in medicine for the treatment of
tuberculosis. As however these uncombined phenoloid bodies have a corrosive action
on the mucous membrane and an unpleasant odour and taste, the employment of their
salts or esters has been resorted to.
The esters or compounds of guaiacol and creosote which have hitherto been
employed either contain, as in the oleates, a comparatively small proportion of the
phenol, or else as in the carbonates a medicinally inactive acid radicle is combined
therewith.
The present invention consists in the preparation of new compounds of guaiacol
and creosote with phosphorous acid and with phosphoric acid, useful in medicine and
the arts. These phosphites or phosphates contain a relatively large proportion of the
phenoloid constituent and are distinguished from the phenol esters hitherto prepared
for use, in the treatment of tuberculosis, by the presence of the phosphatic radicle,
which exercises a very serviceable co-effect in the treatment of tuberculosis.
For the preparation of these esters, three molecular parts of guaiacol or creosote are
preferably dissolved in an alcoholic solution of caustic soda or potash, containing the
amount of alkali sufficient to form the salts of guaiacol or creosote, or the corre-
sponding quantities of the potassium or sodium salts of the phenols may be
suspended in absolute alcohol. To the mixture is slowly added one molecular equivalent
of phosphorus trichloride or of phosphorus oxychloride, and the action which takes
place is regulated by cooling with water, so that the mixture does not become warm.
When the whole of the chloride of phosphorus has been added and the reaction is
ended, the mixture is heated to boiling and the alcohol distilled off. Uncombined
guaiacol or creosote may be removed from the resulting mass by extraction with
aqueous alkali. The residual phosphorous or phosphoric acid ester may be purified
by re-crystallisation from or extraction with a suitable solvent.
Guaiacol phosphite may be obtained in the following manner. 1200 grams guaiacol
is dissolved with the corresponding quantity of pure caustic soda in one litre of ethyl
To this mixture is allowed slowly to flow in with constant cooling, 450 grams

page_text: phosphorus trichloride. The product of the reaction after distilling off the alcohol is
recrystallized from alcohol or from another suitable solvent. The guaiacol phosphite
thus obtained
OC.H.OCH,
P
-OCH,OCH
OCH,OCH,
consists of a white crystalline powder with a faint odour of creosote. It is easily
soluble in alcohol, ether, chloroform and fatty oils, but soluble with difficulty in water,
glycerine, benzene and acetone. At 77.5° C. it melts to a pasty mass. It contains
92-25 per cent. guaiacol.
Creosote phosphite may be obtained in a similar manner, and consists of a yellow
syrupy liquid, with a faint odour of creosote, from which guaiacol phosphite
crystallises out. The proportion of creosote present amounts to about 90 per cent.
This ethereal compound is soluble with difficulty in water but easily in alcohol, ether
and chloroform.
For the preparation of guaiacol phosphate the samne method may be employed but
using the corresponding quantity of the oxychloride or pentachloride instead of the
trichloride of phosphorus. Guaiacol phosphate is soluble in alcohol and ether, insoluble
in water; it is a white odourless crystalline powder and when purified by recrystallisa-
tion from alcohol melts at 94° to 95° C.
Creosote phosphate may be prepared in a similar manner. It is easily soluble in
alcohol and ether, insoluble in water. Its consistency varies according to the
composition of the creosote employed.
The above are all given as examples of the preferable and indirect method of
producing the phosphites and phosphates of guaiacol and creosote, namely by the
action of the chlorides of phosphorus upon the sodium or potassium salts of the same
at low temperatures. It is however also possible to prepare these new esters or
compounds by the direct action of the chlorides of phosphorus upon the phenols at
higher temperatures, but the yield is not so satisfactory. For instance, in order to
prepare guaiacol phosphate according to this direct method, 322 parts of guaiacol may
be mixed with 153 parts of phosphorus oxychloride and heated to 200° C. until no
more hydrochloric acid fumes are liberated. The product of the fusion is then
cooled, treated with caustic soda, extracted with ether and finally recrystallised from
alcohol.
Improvements in the Manufacture of Preparations of Guaiacol and
Creosote.
A communication from LA SOCIÉTÉ CHIMIQUE DES USINES DU RHÔNE, anciennement
GILLIARD P. MONNET ET CARTIER, of Lyons, France, Manufacturers.
I, GEORGE BELOE ELLIS of the Firm of J. C. Mewburn and Ellis of 55 and 56 Chancery
Lane, in the County of London, Chartered Patent Agents, do hereby declare the nature

page_text: of the said invention and in what manner the same is to be performed, to be
particularly described and ascertained in and by the following statement:-
Guaiacol and creosote have long been employed in medicine for the treatment of
tuberculosis. As however these uncombined phenoloid bodies have a corrosive action
on the mucous membrane, and an unpleasant odour and taste, the employment of
their salts or esters has been resorted to.
The esters or compounds of guaiacol and creosote which have hitherto been
employed either contain, as in the oleates, a comparatively small proportion of the
phenol, or else, as in the carbonates, a medicinally inactive acid radicle is combined
therewith.
The present invention consists in the preparation of new compounds of guaiacol and
creosote with phosphorous acid useful in medicine and the arts. These phosphites
contain a relatively large proportion of the phenoloid constituent, and are distinguished
from the phenol esters hitherto prepared for use in the treatment of tuberculosis, by
the presence of the phosphitic radicle, which exercises a very serviceable co-effect in
the treatment of tuberculosis.
For the preparation of these esters, three molecular parts of guaiacol or creosote are
preferably dissolved in an alcoholic solution of caustic soda or potash, containing the
amount of alkali sufficient to form the salts of guaiacol or creosote, or the corresponding
quantities of the potassium or sodium salts of the said phenols may be suspended
in absolute alcohol. To the mixture is slowly added one inolecular equivalent of
phosphorus trichloride, and the action which takes place is regulated by cooling with
water, so that the mixture does not become warm. When the whole of the chloride
of phosphorus has been added and the reaction is ended, the mixture is heated to
boiling and the alcohol distilled off. Uncombined guaiacol or creosote may be removed
from the resulting mass by extraction with aqueous alkali. The residual phosphorous
acid ester may be purified by recrystallization from or extraction with a suitable
solvent.
Guaiacol phosphite may be obtained in the following manner. 1200 grams guaiacol
is dissolved with the corresponding quantity of pure caustic soda in one litre of ethyl
alcohol. To this mixture is allowed slowly to flow in with constant cooling, 450 grams
phosphorus trichloride. The product of the reaction after distilling off the alcohol is
recrystallized from alcohol or from another suitable solvent. The guaiacol phosphite
thus obtained,-

page_text: according to this direct method, 372 parts of guaiacol may be mixed with 137 parts
of phosphorus trichloride and heated to 200°C. until no more hydrochloric acid fumes
are liberated. The product of the fusion is then cooled, treated with caustic soda,
extracted with ether, and finally recrystallized from alcohol.
And having now particularly described and ascertained the nature of the said
invention as communicated to me and in what manner the same is to be
performed, I declare that what I claim is :-
1. The preparation of the phosphites of guaiacol and creosote by treatment of the
alkali salts of guaiacol or creosote in alcoholic solution with phosphorus trichloride
and distilling of the alcohol, substantially as described.
2. The preparation of the phosphites of guaiacol and creosote by heating guaiacol
or creosote with phosphorus trichloride at about 200° C. until no more hydrochloric
acid fumes are liberated, and purifying the product, substantially as described.
3. As new products, the phosphites of guaiacol and creosote.
Dated this 3rd day of September 1807
J. C. MEWBURN & ELLIS,
55 and 56 Chancery Lane, London, Chartered Patent Agents.