Improvements in the Production of Phenolic Carbonates.
Year: 1897

page_text: Improvements in the Production of Phenolic Carbonates.
A communication from CHEMISOHE FABRIK VON HEYDEN, GESELLSCHAFT MIT
BESCHRAENKTER HAFTUNG, of Radebeul, near Dresden, Saxony, German Empire
Manufacturers.
I, JOHN CLAYTON MEWBURN, 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:-
In the Specification of Patent No. 19074 of 1890 a method of producing the
carbonates of a number of phenolic bodies is described, which method is character-
ized by the action of carbon oxychloride COCI, (phosgen) upon certain phenols or
their salts. My foreign correspondents have now discovered that the practical
carrying out of this method can be modified by allowing the carbon oxychloride to
react not directly with the phenolic substances, but previously with alcohols or other
phenols, and by then heating the resulting chloro-carbonic ester or carbonic ester,
instead of the carbon oxychloride, with the phenolic substances the carbonates of
which it is desired to produce.
For example, guaiacol carbonate is obtained in accordance with the above
mentioned specification by the reaction of guaiacol or guaiacol salts with carbon
oxychloride.
This method can be modified according to this invention by first producing a

page_text: While the method described in the specification before referred to is characterized
by the equation.---

page_text: OCH,OCH,
OCH,
It is obviously unnecessary to isolate the guaiacol-ethyl-carbonate; it is preferable,
rather, to heat the mixture of one equivalent chloro-carbonic alkyl ester with one.
equivalent, or better two equivalents or excess, of guaiacol, preferably substituting a
guaiacol salt for the one equivalent of guaiacol.
Dated this 26th day of October 1897
MIT
A communication from CHEMISCHE FABRIK VON HEYDEN, GESELLSCHAFT
BESCHRAENKTER HAFTUNG, of Radebeul, near Dresden, Saxony, German Empire,
Manufacturers.
I, JOHN CLAYTON MEWBURN, of the Firm of J. C. Mewburn & Ellis, of 55 and
56, Chancery Lane, in the County of London, Chartered Patent Agents, do hereby
declare the nature of this invention, and in what manner the same is to be per-
formed, to be particularly described and ascertained in and by the following state-
ment:-
In the Specification of Patent No. 19074 of 1890 a method of producing the
carbonates of a number of phenolic bodies is described, which method is characterized
by the action of carbon oxychloride COCI, (phosgen) upon certain phenols or their
salts. My foreign correspondents have now discovered that the practical carrying out
of this method can be modified by allowing the carbon oxychloride to react not
directly with the phenolic substances, but previously with alcohols or with other
phenols, and by then heating the resulting chloro-carbonic ester or carbonic ester,
instead of the carbon oxychloride, with the phenolic substances the carbonates of
which it is desired to produce.
For example, guaiacol carbonate is obtained in accordance with the above
mentioned Specification by the reaction of guaiacol or guaiacol salts with carbon
oxy-chloride.
This method can be modified according to this invention by first producing
Cl

page_text: For example, Two equivalents of guaiacol or an excess thereof are heated in an
open vessel with one equivalent of diphenyl carbonate as long as phenol continues to
distill off the temperature being maintained higher than 180° C.
place in accordance with the equation:-
The reaction takes

page_text: Upon further heating, either alone or with excess guaiacol, the guaiacol carbonate
is produced from the intermediately formed ethyl-carbonate of guaiacol, probably in
accordance with the equation.
Two equivalents of guaiacol or an excess of it are heated in an open vessel. At a
temperature of 100° C. or a higher temperature one atom of metallic sodium is added
and at the end of the first reaction one equivalent of chloro-carbonic ethyl-aster is
added. The mixture is heated as long as it has an alkaline reaction. The resulting
product is washed with water and crystallised from alcohol.
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 method of producing the carbonates of phenolic bodies hereinbefore referred
to which consists in causing carbon oxychloride (phosgen) to react first with an
alcohol or with a phenol to produce a chloro-carbonic ester or carbonic ester, and in
then heating said ester with the phenolic body the carbonate of which it is desired to
produce, or a salt thereof, substantially as hereinbefore described.
2. The method of producing the carbonates of phenolic bodies herein before referred
to which consists in heating a chloro-carbonic ester or carbonic ester with the phenolic
body the carbonate of which it is desired to produce, or a salt thereof, substantially
as herein before described..
3. The method of producing guaiacol carbonate or other phenolic carbonate which
consists in heating guaiacol or other phenolic body with a carbonic ester, substantially
as herein before described.
4. The method of producing (guaiacol) carbonate or other phenolic carbonate
which consists in heating guaiacol or other phenolic body or a salt thereof with a
chloro-carbonic ester, if necessary in presence of a hydrochloric acid neutralizing
medium, and further heating the intermediate product either alone or in presence of
excess of the phenolic body substantially as hereinbefore described.
5. The method of producing guaiacol carbonate or other phenolic carbonate which
consists in heating a mixture of a chloro-carbonic ester with a mixture of the said
phenolic body and a salt thereof, substantially as hereinbefore described.
552
10001
J. C. MEWBURN & ELLIS,
55 and 56, Chancery Lane, London, Chartered Patent Agents.