A Process for the Production of Indifferent (Neutral) Compounds of Alkoxylated Phenols.
Year: 1897

page_text: Date of Application, 25th May, 1897-Accepted, 14th Aug., 1897.
COMPLETE SPECIFICATION.
A Process for the Production of Indifferent (Neutral) Compounds
of Alkoxylated Phenols.
I, LEONHARD LEDERER of 76A Gabelsbergerstrasse Munich in the Empire of
Germany, Doctor of Science, do hereby declare the nature of this invention and
in what manner the same is to be performed to be particularly described and
ascertained in and by the following statement :-
Alkoxylated phenols are, as is well known, extensively used in medicine. When
used internally their caustic properties and their unpleasant taste frequently cause
disorders. These inconvenient secondary effects are produced by the free hydroxyl.
If the hydroxyl is in combination, the phenol-character of the alkoxylated phenols
disappears, and therewith also their caustic action.
For the purpose of increasing the therapeutic usefulness of the alkoxylated
phenols, it is therefore advisable to neutralise the OH-group by the introduction of
radicals. I have discovered a process which is based upon an hitherto completely
unknown property of the alkoxylated phenols. Although these substances are
otherwise analogous in their proporties to phenol, they have quite a special
behaviour as regards potassium carbonate. They have the property of forming
crystallised compounds with potassium carbonate, which property is wholly wanting
in phenol and its homologues.
The compounds of the alkoxylated phenols with potassium carbonate are
permanent in the air, and are partially decomposed by water. They are very
readily transformed, and for this reason they are very suitable for the production of
derivatives of the hydroxylated phenol-ethers in which the bydrogen of the
hydroxyl group is substituted. As will be seen from the following description, the
new process may also be employed with mixtures of alkoxylated phenols such as are
present for example in wood-tar oil, oil of cloves, and similar products, without
previous refining of the alkoxylated phenols being necessary. This is indisputably
of the very greatest technical importance.
I. One part of liquid guajacol of commerce is shaken up with two parts of a strong
solution of potassium carbonate. After removal of the aqueous portion the crystal
cake thereby produced, and which is saturated with oil, is washed with ether or
benzine for the purpose of removing the phenols therefrom, and finally the compound
of potassium carbonate and guajacol is brought into reaction with phosgen. After
having washed the mass of the reaction in water there remains a carbonate of
guajacol.
Instead of isolating the crystalline mass obtained by shaking guajacol with
carbonate of potassium, the same result may be obtained equally well by bringing the
crystalline mass directly into reaction with phosgon. The phenols mixed therewith
are removed either by washing in a dilute solution of alkali, or with steam or water
HODOW

page_text: II. Equal parts of creosote and potassium carbonate are brought into intimate
contact for some time, with an addition of a small quantity of water, and are then
brought into reaction with phosgen. After complete transformation or conversion,
the mass of reaction is washed with a dilute aqueous solution of alkali for the
purpose of removing the phenols that have no value. In the residue there remain
the carbonate ethers of guajacol and of its homologues in the form of a thick oil.
III. Carbonate-of-potassium-of-guajacol is mixed with chlorocarbonic acid ether
in definite proportions. A reaction is at once produced with development of heat
which reaction rather quickly ceases. On shaking with water, the carbonic chloride
of ether of guajacol is extracted in the form of an almost colourless oil.
IV. The crystalline mass saturated with oil obtained by the treatment of liquid
guajacol with a solution of potassium carbonate is shaken up with the proper
quantity of chloride of benzoyl After the reaction is finished, the mixture
produced by the reaction is washe'd in a dilute alkaline solution for the purpose of
removing the phenols that have no value, and any chloride of benzoyl which may be
present in excess is washed so that there remains benzoyl-guajacol.
V. Nine parts of potassium carbonate of guajacol are sprinkled with five parts of
anhydrous acetic acid. The mixture heats at once. After cooling the mixture
produced by the reaction is washed in dilute soda lye and the acetic ether is
separated from the guajacol..
VI. Seven parts of anhydrous benzoic acid and six parts of potassium carbonate of
guajacol are rubbed together. In a short time the mixture becomes of a rather
liquid consistency and remains so even after having been left alone for a long period
of time. From this mixture the benzoyl-guajacol is separated by washing in water
at first in the form of an oil which however soon solidifies into crystals. Teh
procedure is the same when instead of guajacol thero is employed an alkoxylated
phenol of any kind, and when instead of phosgen, there are employed either a
chlorocarbonic acid ether, or acid chlorides, or acid anhydrides.
Having now particularly described and ascertained the nature of my said inven-
tion and in what manner the same is to be performed, I declare that what I
claim is :-
A process for the formation of neutral combinations, of alkoxylated phenols
consisting in causing to react:―
(1) Alkoxylated phenols in the presence of potassium carbonate, either in the
solid state or in solution, or
(2) The compounds of potassium carbonate of the alkoxylated phenols; upon
carbonic chloride of oxygen (phosgen) chlorocarbonic acid & ethers, acid chlorides,
acid anhydrides, or other similar substances, as set forth.
Dated this 25th day of May 1897
Dated this 25th day of May 1897
ROBERT E. PHILLIPS, Assoc. M. Inst. C.E., M. I. Mech. E.,
Consulting Engineer and Patent Agent,
70, Chancery Lane, London, W.C., Associate Agent.