IMPROVEMENTS IN THE PRODUCTION OF CINNAMIC ACID AND OF SUBSTITUTED CINNAMIC ACIDS FROM BENZYLIDENACETONE AND ITS SUBSTITUTION PRODUCTS
Year: 1882

page_text: LETTERS PATENT to John Erskine of 151 St. Vincent Street Glasgow in
the County of Lanark North Britain Solicitor for an Invention of
IMPROVEMENTS IN THE PRODUCTION OF CINNAMIC ACID AND OF SUBSTITUTED
CINNAMIC ACIDS FROM BENZYLIDENACETONE AND ITS SUBSTITUTION PRODUCTS
A communication to him from abroad by the Farbwerke vorm: Meister
Lucius and Brüning of Hoechst-am-Main in the Empire of Germany, a
Company carrying on business as Chemical Manufacturers
PROVISIONAL SPECIFICATION left by the said John Erskine at the Office
of the Commissioners of Patents on the 7th July 1882.
JOHN ERSKINE, of 151 St. Vincent Street Glasgow, in the County of Lanark,
North Britain, Solicitor. "IMPROVEMENTS IN THE PRODUCTION OF CINNAMIC
ACID AND OF SUBSTITUTED CINNAMIC ACIDS FROM BENZYLIDENACETONE AND ITS
SUBSTITUTION PRODUCTS." [A communication to him from abroad by the
Farbwerke vorm: Meister Lucius and Brüning of Hoechst-am-Main in the Empire
of Germany, a company carrying on business as Chemical Manufacturers]
My Invention and Process hereinafter described for the production of Cinnamic
Acid or of Cinnamic Acids substituted in the benzol nucleus, from benzylidenacetone
or from the corresponding substitution products consists in exposing these acetones
to the action of hypochlorites hypobromites or hypoiodites. The formation of
cinnamic acid for example, from benzylidenacetone takes place according to the
equation
5
CH. CH CH 00. CH + 3Na (. Ca=
CH. CHCH. CO. O. Na + CH Ce₂ + 2 Na. O H.
The special method I employ in carrying my Invention into practice is as
follows: I gently heat on a water bath 15 parts of benzylidenacetone with a
solution of 48 parts of bromine dissolved in 650 parts of soda lye of 4°/
When

page_text: the presence of hypobromous acid in the solution can no longer be proved, the
transformation of the acetone into cinnamic acid, as expessed by the above equation
is completed.
When the bromoform generated in the process has separated from the aqueous
solution, I add to it diluted sulphuric acid, collect the separated cinnamic acid and 5
purify the same by recrystallization from water or alcohol.
In the same way I proceed when instead of the benzylidenacetone, its derivatives
substituted in the benzol nucleus, are to be used for the production of substituted
cinnamic acid. By heating for example 20 parts of orthonitro-benzylidenacetone,
obtainable by the method described in the Provisional Specification of Joseph 1
Anthony Dixon, No. 1,453. A.D. 1882, with 800 parts of an aqueous solution of
hypochlorite of sodium of 3%, I obtain nearly the theoretical quantity of
orthonitro-cinnamic acid.

page_text: SPECIFICATION in pursuance of the conditions of the Letters Patent filed
by the said John Erskine in the Great Seal Patent Office on the
23rd December 1882.
JOHN ERSKINE, of 151 St. Vincent Street, Glasgow, in the County of Lanark,
North Britain, Solicitor. "IMPROVEMENTS IN THE PRODUCTION OF CINNAMIC
ACID AND OF SUBSTITUTED CINNAMIC ACIDS FROM BENZYLIDENACETONE AND ITS
SUBSTITUTION PRODUCTS." The said Invention being a communication to me from
abroad by the Farbwerke vorm: Meister, Lucius and Brüning, of Hoechst-am-Main,
in the Empire of Germany, a Company carrying on business as Chemical
Manufacturers.
The Invention and Process hereinafter described for the production of Cinnamic
Acid or of Cinnamic Acids substituted in the benzol nucleus from benzylidenacetone
or from the corresponding substitution products consists in exposing these acetones
to the action of hypochlorites, hypobromites or hypoiodites. The formation of
cinnamic acid, for example, from benzylidenacetone, takes place according to the
CH, OH CH CO CH₂ + „Na O Ce=
CH, CHCH CO O Na+ CH C, + 2 Na O H.
The special method the communicators of this Invention employ in carrying
their Invention into practice is as follows:-They gently heat on a water-bath
15 parts of benzylidenacetone with a solution of 48 parts of bromide dissolved in
650 parts of soda lye of 4%. When the presence of hypobromous acid, in the
solution can no longer be proved, the transformation of the acetone into cinnamic
acid, as expressed by the above equation is completed.
When the bromo form generated in the process has separated from the aqueous
solution, there is added to it diluted sulphuric acid, and the separated cinnamic
acid is collected and purified by recrystallization from water or alcohol.
The same method of procedure is followed when instead of the benzylidenacetone,
its derivatives substituted in the benzol nucleus, are to be used for the production
of substituted cinnamic acid. By heating for example 20 parts of orthonitro-
benzylidenacetone, obtainable by the method described in the Specification of
Joseph Anthony Dixon, No. 1453, A.D. 1882, with 800 parts of an aqueous
solution of hypochlorite of sodium of 3°, there is obtained nearly the theoretical
quantity of orthonitro-cinnamic acid.
Having now described and particularly ascertained the nature of the said
Invention, and the system mode or manner in or under which the same is or may
be used or practically carried into effect it is to be observed in conclusion that
what is considered to be novel and original and therefore claimed as the Invention
secured to the Inventors by the hereinbefore in part recited Letters Patent is :-
The production of cinnamic acid and of cinnamic acids substituted in the benzol
nucleus, from the monobenzylidenacetone and the corresponding substitution
products by means of hypochlorites hypobromites or hypoiodites, all in manner
hereinbefore described or in manner substantially the same
In witness whereof I the said John Erskine have hereunto set my hand
and seal this twenty-second day of December in the year of Our Lord One
thousand eight hundred and eighty two.
TATAY ANGINIA