New Process for Producing Carbonic Acid Ethers and Intermediate Products therefrom.
Year: 1898

page_text: PROVISIONAL SPECIFICATION.
[Communicated from abroad by the FARBENFABRIKEN VORMALS FRIEDRICH BAYER & CO.,
of Elberfeld, Germany.]
New Process for Producing Carbonic Acid Ethers and Intermediate
Products therefrom.
I, HENRY EDWARD NEWTON, of the Office for Patents, 6, Bream's Buildings,
Chancery Lane, in the County of London, Patent Agent, do hereby declare the
nature of this invention to be as follows:-
My foreign correspondents have found that, on causing carbon oxychloride, or
phosgene (CO Cl₂), to act on pyridine, a new chlorinated body is readily produced,
which, according to analytical researches, has the formula:
To a solution of 316 parts of pure pyridine, dissolved in 1000 parts of dry benzene,
a solution prepared from 198 parts of carbon oxychloride and 500 parts of benzene is
added, with stirring, the reaction mixture being kept cool. A lemon-yellow pre-
cipitate separates immediately, which is quickly filtered off and dried in vacuo.
is the new chlorinated derivative from pyridine, having the formula above given.
Price 8,71
It

page_text: To the resulting mixture, 6.4 parts of pure methylic alcohol are added, with
continuous stirring and careful cooling. The yellow color of the mixture disappears
by and by, and has changed into white at the end of the reaction. Subsequently,
the mixture is washed first with a small quantity of water, and then with a calcium
chloride solution, which has been rendered slightly acid by the addition of hydro-
chloric acid. The liquid is dried and distilled. Thus, the carbonic acid ether (the
dimethyl carbonate of the formula―
To a mixture prepared from 2.57 parts of pyridine chlorocarbonyl and ten parts of
dry benzene, a solution of 2:48 parts of guaiacol in ten parts of benzene is added, with
stirring and careful cooling.
When the yellow color of the mixture has disappeared, the reaction will be finished.
When this stage is reached, the mixture is washed first with water, and then with a
very dilute hydrochloric acid. Subsequently the benzene is distilled off by means of
steam. Thus, an oil is obtained which quickly changes into a crystalline mass. On
recrystallizing this mass from alcohol, the pure carbonic acid ether (carbonate) of
guaiacol, having the formula-
is obtained.
My foreign correspondents wish it to be understood that they do not intend to
confine themselves to the particulars given in the above specification, as these can be
varied within wide limits, without altering thereby the nature of the present
invention.

page_text: New Process for Producing Carbonic Acid Ethers and Intermediate
Products therefor.
I, HENRY EDWARD NEWTON, of The Office for Patents, 6, Bream's Buildings,
Chancery Lane, in the County of London, Patent Agent, do hereby declare the
nature of this invention and in what manner the same is to be performed, to he
particularly described and ascertained in and by the following statement :-
My foreign correspondents have found that, on causing carbon oxy-chloride or
phosgene (CO C₁₁) to act on pyridine, a new chlorinated body is readily produced,
which, according to analytical researches, has the formula ;-
5

page_text: 25-7 parts of pyridine chlorocarbonyl are mixed with 50 parts of xylene. To the
resulting mixture, 6-4 parts of pure methylic alcohol are added, with continuous
0 stirring and careful cooling. The yellow color of the mixture will have changed into
white at the end of the reaction. Subsequently, the mixture is washed, first, with a
small quantity of water, and then with a calcium chloride solution which has been

page_text: rendered slightly acid by the addition of hydrochloric acid. From the liquid thus
obtained, the pure carbonic acid ether, (the dimethyl carbonate of the formula-
To a mixture prepared from 2.57 parts of pyridine chlorocarbonyl and 10 parts of
dry benzene, a solution of 2.48 parts of guaiacol, in 10 parts of benzene, is added with
stirring and careful cooling.
When the yellow colour of the mixture has disappeared, the reaction will be
finished. When this stage is reached, the mixture is washed first with water, and
then with a very dilute hydrochloric acid. Subsequently, the benzene is distilled off
by means of steam. Thus, an oil is obtained which quickly changes into a crystalline
mass. On recrystallizing this mass from alcohol, the pure carbonic acid ether
(carbonate) of guaiacol, having the formula-
is obtained.
My foreign correspondents wish it to be understood that they do not intend to
confine theinselves to the particulars given in the above specification, as these can be
varied within wide limits, without altering thereby the nature of the present
invention.
Having now particularly described and ascertained the nature of the said inven-
tion and in what manner the same is to be performed (as communicated to me
from abroad), I declare that what I claim is :-
1. The process for producing new "chloro carbonyl" derivatives from bases of the
pyridine series, which process consists in allowing carbon oxychloride (phosgene),
perchlormethylformiate, or hexachlordimethylcarbonate, to act on bases of the
pyridine series, substantially as herein before described.
"
2. The process for producing carbonic acid ethers by causing the "chlorcarbonyls
obtainable according to the foregoing Claim 1, to act on fatty alcohols, phenols, or
acid phenolic ethers, substantially as herein before described.
3. As new articles of manufacture, the new bodies obtainable according to the
processes herein before described and claimed.
Dated this 23rd day of March 1899.