Manufacture of Lactylderivatives of Methylaniline, Ethylaniline, Paraanisidine, and Paraphenetidine.
Year: 1892

page_text: Date of Application, 30th June, 1892
Complete Specification Left, 21st Mar., 1893-Accepted, 6th May, 1893
PROVISIONAL SPECIFICATION.
[Communicated from abroad by the firm of C. F. BOEHRINGER & SÖHNE, of
Waldhof, near Mannheim, Baden, Germany, Manufacturers.]
Manufacture of Lactylderivatives of Methylaniline, Ethylaniline,
Paraanisidine, and Paraphenetidine.
I, CHARLES DENTON ABEL of No. 28 Southampton Buildings in the County
of London, Consulting Engineer and Chartered Patent Agent do hereby declare
the nature of this invention to be as follows:-
The lactylderivatives of methylaniline, ethylaniline, paraanisidine and para-
phenetidine are obtained by heating the lactates of the said aromatic bases to from
130° to 180° C. The heating is continued until the resulting separation of water
is completed, that is to say, until no more aqueous vapour escapes from the fused
mass. These lactylderivatives may also be obtained by heating the said bases with
lactic anhydride or with lactide or with lactic acid esters at the above named
temperatures.
The said lactyl compounds are most advantageously prepared in a manner of
which the following is an example:
27 kilos. paraphenetidine are dissolved in the equivalent quantity of dilute
sulphuric acid of about 20° Bé and are mixed with a hot or cold aqueous solution
of 30 kilos. of calcium lactate (Ca(CHO), + 5 HO),..
To the mixture obtained is added strong alcohol until the whole of the calcium
sulphate has been completely precipitated, that is to say, until a sample-filtrate of
the liquid will not become turbid by the further addition of alcohol. By filtering,
the solution of the lactate of paraphenetidine is separated from the calcium
sulphate, and the alcohol contained in the solution can be regained by distillation.
By evaporation the water of solution is removed and the residue obtained,
consisting of lactate of paraphenetidine, is heated gradually to about 180° C., until
no more aqueous vapour is given off from the fused mass.
The lactyl compound thus obtained, after being cooled to about 100° C., is then
dissolved in boiling water with the addition of some decolorising carbon if
necessary.
From the filtered clear solution the greater portion of the lacto-paraphenetidine
separates in crystalline form. The remainder can be obtained from the solution
by evaporation.
In place of calcium lactate there may of course be used other metallic lactates
in the above process, such for example as zinc lactate.
Also, in place of the sulphate solution of the aromatic base, solutions thereof in
other mineral acids or also in organic acids, as for example oxalic acid, tartaric
acid and the like, may be used.
If the metallic salt obtained by double decomposition is soluble in alcohol, the
lactate of the aromatic base employed can best be separated from the compound by
means of ether, and after distilling off the ether it can be further treated.
The lactylderivatives of the paraanisidine and paraphenetidine are produced by
the described process in almost the theoretical quantities.
In the production of the lactylderivatives of methylaniline and ethylaniline,
there is added to the lactates thereof, before heating, about the same quantity of
the bases contained in the latter in a free state, whereby a more complete formation
of anilide will be obtained.
In this case the excess of base must be driven off from the fused mass by means
of steam after heating.

page_text: The obtained residue, which contains the lactylderivative, is purified by
recrystallisation from hot water as above described.
The lactylderivatives of the said aromatic bases possess very good crystallising
power, and have considerable therapeutic properties.
Lact-methylanilide melts at 87.5° C.
T
11
ABEL & IMRAY,
Agents for the Applicant.
COMPLETE SPECIFICATION.
Manufacture of Lactylderivatives of Methylaniline, Ethylaniline,
Paraanisidine, and Paraphenetidine.
I, CHARLES DENTON ABEL, of No. 28 Southampton Buildings, in the County
of London, Consulting Engineer and Chartered Patent Agent, 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:-
The lactyl derivatives. of methylaniline, ethylaniline, paraanisidine and para-
phenetidine are obtained by heating the lactates of the said aromatic bases to
from 130° to 180° C. The heating is continued until the resulting separation of
water is completed, that is to say, until no more aqueous vapour escapes from the
fused mass. These lactyl-derivatives may also be obtained by heating the said
bases with lactic anhydride or with lactide or with lactic acid esters at the above
named temperatures.
The said lactyl compounds are most advantageously prepared in a manner of
which the following is an example:
27 kilos. paraphenetidine are dissolved in the equivalent quantity of dilute
sulphuric acid of about 20° Bé and are mixed with a hot or cold aqueous solution
of 30 kilos. of calcium lactate (Ca(C₂H₂O3)2 + 5 H₂O).
To the mixture obtained is added strong alcohol until the whole of the calcium
sulphate has been completely precipitated, that is to say, until a sample-filtrate of
the liquid will not become turbid by the further addition of alcohol.
By filtering, the solution of the lactate of paraphenctidine is separated from the
calcium sulphate, and the alcohol contained in the solution can be regained by
distillation.
By evaporation the water of solution is removed and the residue obtained, con-
sisting of lactate of paraphenetidine, is heated gradually to about 180° C., until no
more aqueous vapour is given off from the fused mass.
The lactyl compound thus obtained, after being cooled to about 100° C., is then
dissolved in boiling water with the addition of some decolorising carbon if necessary.
From the filtered clear solution the greater portion of the lacto-paraphenetidine
separates in crystalline form. The remainder can be obtained from the solution by
evaporation.
In place of calcium lactate there may of course be used other metallic lactates in
the above process, such for example as zinc lactate.
Also, in place of the sulphate solution of the aromatic base, solutions thereof in
other mineral acids or also in organic acids, as for example oxalic acid, tartaric
acid and the like, may be used.
If the metallic salt obtained by double decomposition is soluble in alcohol, the
lactate of the aromatic base employed can best be separated from the compound by
ineans of ether, and after distilling off the ether it can be further treated."

page_text: Having now particularly described and ascertained the nature of this inven
tion and in what manner the same is to be performed, I declare that what I
claim is :-
Manufacture of lactyl derivatives of methylaniline, ethylaniline, paraanisidine,.
and paraphenetidine, by heating the said aromatic bases with lactic acid or lactic
anhydride or with lactic acid esters, or by heating the lactates of the said aromatic
bases, obtained by double decomposition of metallic lactates, with mineral or
organic acid salts of the said aromatic bases until the completion of the resulting
separation of water or alcohol or by heating the said aromatic bases with lactide,.
until the fused mass dissolves clear in boiling water, substantially as described.
Dated this 21st day of March 1893.
ABEL & IMRAY,
Agents for the Applicant.