A Manufacture of Iso Eugenol and of certain of its Derivatives and their Application to the Manufacture of Vanilline.
Year: 1890

page_text: Date of Application, 1st Nov., 1890
Complete Specification Left, 15th July, 1891-Accepted, 15th Aug., 1891
PROVISIONAL SPECIFICATION.
A Manufacture of Iso Eugenol and of certain of its Derivatives and
their Application to the Manufacture of Vanilline.
1, GEORGES DE LAIRE, of 92 Rue St. Charles, Paris, France, Chemist, do
hereby declare the nature of this invention to be as follows:-
:-
CH
-
CH-CH³
When obtained in this manner iso eugenol supposes the previous production of
vanilline and cannot be considered as a material serving for the production of
vanilline.
The endeavours to obtain directly iso eugenol by means of the process which
allows of the transformation of safrol into iso safrol, have not given practical
results, as shewn by the recent publications of Messrs. Ciamician and Eykmann.
The process which constitutes part of the present invention allows of the ready
preparation of iso eugenol by means of eugenol or the essence of cloves, a substance
which is readily obtained in commerce.
Iso eugenol being once obtained by substituting for the hydrogen of its group,
phenylhydroxyle, the radical of an organic acid, acetylic, propionylic, butylic,
valerylic, benzoylic, derivatives are prepared, which by their oxidation give
vanilline.
According to the manner in which is effected the substitution of the radical of the
organic acid for the hydrogen of the phenylhydroxyle group, mono-molecular or
polymerised derivatives are obtained. This observation is essential, because these
two classes of derivatives behave quite differently when they are oxidized.
The polymerised derivatives only give small yields of vanilline; the mono-
molecular derivatives alone should be used for being transformed into this substance
by one of the oxidation processes already known.
This essential point has never before.been indicated, even scientifically.
Thus the benzoylic derivative of iso eugenol prepared by Messrs. Tiedemann and
Kraaz which melts at 159° to 160°, is a polymerised derivative, and not mono-
molecular as is proved by the determination of its mono-molecular weight.
The following is a suitable mode of operating:
TARATION UT 150 MUGAL
500 gr. eugenol
1250 hydrate of potass
"
2500
"
amylic alcohol
are heated to boiling point in an apparatus provided with a cohobator. The
duration of the heating should be from 16 to 24 hours, at the end of which time
the reaction is complete the amylic alcohol is driven off by means of a current of
steam, and the iso eugenol is separated by treating the mass with dilute sulphuric
acid or with hydrochloric acid. The iso eugenol separates and is collected by
decantation; it is washed several times and is purified by distillation; it boils at
from 580 to 2600 (

page_text: ABEL & IMRAY,
Agents for the Applicant.
COMPLETE SPECIFICATION.
A Manufacture of Iso Eugenol and of certain of its Derivatives and
their Application to the Manufacture of Vanilline.
I, GEORGES DE LAIRE, of 92 Rue St. Charles, Paris, France, Chemist, 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 :-
When obtained in this manner iso-eugenol supposes the previous production of
vanilline and cannot be considered as a material serving for the production of
vanilline.
The endeavours to obtain directly iso-eugenol by incans of the process which
allows of the transformation of safrol into iso safrol, have not given practical
results, as shewn by the recent publications of Messrs. Ciamician and Eykmann.
The process which constitutes part of the present invention allows of the ready
preparation of iso-eugenol by means of eugenol or the essence of cloves, a substance
which is readily obtained in commerce.

page_text: Iso-eugenol being once obtained by substituting for the hydrogen of its group,
phenylliydroxyle, the radical of an organic acid, acetylic, propionylic, butylic,
valerylic, benzoylic, derivatives are prepared, which, by their oxidation, give
vanilline.
According to the manner in which is effected the substitution of the radical of
the organic acid for the hydrogen of the phenylhydroxyle group, mono-molecular or
polymerised derivatives are obtained. This observation is essential, because these
two classes of derivatives behave quite differently when they are oxidized.
The polymerised derivatives give only small yields of vanilline; the mono-
molecular derivatives alone should be used for being transformed into this substance
by one of the oxidation processes already known.
This essential point has never before been indicated, even scientifically. Thus
the benzoylic derivative of iso-eugenol prepared by Messrs. Tiedmann and Kraaz
which melts at 159° to 160°, is a polymerised derivative, and not mono-molecular,
as is proved by the determination of its monomolecular weight.
The following is a suitable mode of operating :-

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 :-
1. The manufacture of iso-eugenol on a commercial scale, substantially as herein
described.
2. The process whereby monomolecular or polymerised derivatives of iso-eugenol
may be produced at will by the substitution of an acid radical for the phenyl-
hydroxyle hydrogen of iso-eugenol, substantially as described.
3. The application of the mono-molecular derivatives of iso-eugenol to the many-
facture of vanilline, substantially as described.
Dated this 15th day of July 1891.
ABEL & IMRAY,
Agents for the Applicant.