Improvements in and connected with the Manufacture of Artificial Camphor from Hydrocarbon Oils of the Terpene Series.
Year: 1898

page_text: Improvements in and connected with the Manufacture of Artificial
Camphor from Hydrocarbon Oils of the Terpene Series.
I, JOHN EDWARD TENISON WOODS, of 38, Chantry Road, Brixton, in the County
of Surrey, Engineer and Chemist, do hereby declare the nature of this invention to
be as follows:-
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0.
The object of this invention is to produce camphor from various permanently fluid
hydrocarbon oils of vegitable origin such as terebenes (turpentines) oils of rosemary
lemon peppermint and others which have a composition of Co closely
approximating to that of natural gum camphor the composition of which is C₁H¸¸◊
Attempts have been made from time to time to convert these oils or some of
then turpentine for example into camphor by combining them with the one
equivalent of oxygen wanting, by chemical reaction, without otherwise changing
the constituents of the oil to be acted upon, but the results have been unsatisfactory.
By my present invention any of the terebene or turpentine oils or their homolognes
can be converted into solid camphor of the composition C₁₁O by the processes
now to be described.
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16
Now according to the first part of this invention I expose American turpentine to
a stream of hydrochloric acid gas whereby it becomes converted into crystalline
mono-hydrochloride of terebene C₁H₁H Cl. which substance somewhat resembles
camphor and is well known. I then purify the mono-hydrochloride of terebene by
sublimotion in a current of steam, then boil the sublimed product with acetate of
soda and a free alkali or alkaline carbonate by which treatment the substance looses
its hydrochloric acid and becomes a solid substance (camphene) isomeric of the oil
first used and of the composition C10 H16-
This substance after purification is converted into ordinary camphor C₁H₁O by
heating it with an oxidising re-agent such as an alkaline permanganate chromate or
bichromate, ferrate or chlorate and very dilute sulphuric acid nascent oxygen is liberated
which combines with the camphene Č₁₁ formning ordinary camphor C₁₁O.
10 16
Or I may produce camphene by agitating turpentine with strong sulphuric acid
which form of the substance may also be converted into ordinary camphor by
oxidation by the process herein before specified.
According to the second part of this invention American turpentine is subjected for
a long time to a current of hot air and dry steam, the air and steam being at the same
temperature which causes it to absorb oxygen and becomes converted into camphoric
acid (CHO) and dioxide of hydrogen (H₂O₂).

page_text: equivalents of oxygen it contains with nascent hydrogen produced by the electrolysis
of the water in the solution or by adding zinc or iron and dilute sulphuric acid to
the solution leaving floating in the solution ordinary camphor C₁₁O.
According to the third part of my invention I form camphorie acid by the
oxidation of turpentine oil by blowing hot air through it with dry steam as above
described I then heat the camphoric acid so formed with three equivalents of camphene
produced from turpentine by either of the methods hereinbefore specified and
boiling the mixture with the addition of acetate of soda or formate of soda when
four equivalents or ordinary camphor separate which may be purified by dry heat or 1
in a current of steam thus
T. E. HALFORD,
11, Furnival Street, London, E.C., Agent for Applicant.
Improvements in and connected with the Manufacture of Artificial
Camphor from Hydrocarbon Oils of the Terpene Series.
I, JOHN EDWARD TENISON WOODS, of 38, Chantry Road, Brixton, in the County of
London, Engineer and 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 :-
The object of this invention is to produce camphor from various permanently
fluid hydrocarbon oils of vegetable origin such as terebenes (turpentines) oils of
rosemary, lemon peppermint and others which have a chemical composition of CH 16
closely approximating to that of natural gum camphor the composition of which
is C10H160.
Various attempts have been made from time to time to convert these oils or some
of them, turpentine for example into camphor by combining them with the one
equivalent of oxygen wanting by chemical re-action without otherwise changing the
constituents of the oil under treatment, but the results have hitherto been
unsatisfactory.
My present invention enables any of the terebenes or turpentine oils to be
converted into camphor of the composition C₁H₁O by the processes hereinafter
described.
Now according to this invention I convert the oil into mono-hydrochloride of
terebene or into camphoric acid and add to or subtract therefrom the necessary
quantity of oxygen by the treatment now to be described leaving the resulting
product of the same chemical composition as ordinary gun camphor.
Now according to the first method of carrying out my invention I form crystalline
mono hydrochloride of terebene C₁ H₁H Cl. by exposing American turpentine to a
stream of hydrochloric acid gas this mono-hydrochloride somewhat resembles gum
camphor and is well known.

page_text: 91.
*O*HE+OHO="H+'OHO
According to the third part of this invention I form camphoric acid by the
oxidation of turpentine oil by blowing warm dry air and steam both at a temperature
of about 230° Fahr. through it as above described.
I then add to the camphoric acid so formed three equivalents of camphene produced
from turpentine by either of the methods herein before specified, gradually heat the
samne till fused and subsequently boil the mixture with the addition of fro:n five to
ten per cent. of acetate of soda or formate of soda when four equivalents of ordinary
camphor separate which latter may be purified by sublimation either by dry heat or
in a current of steam thus:-
The acetate of soda or formate of soda used is not decomposed but acts, in
determining this reaction, by catalytic action and also as a carrier.
Having now particularly described and ascertained the nature of my said
invention I declare that what I claim is :-
.
1 The conversion of mono-hydrochloride of terebene into solid camphene by boiling
the mono-hydrochloride with acetate of soda and a free alkali or alkaline carbonate
and the subsequent conversion, after purfication, of the camphene into camphor by
heating it with an oxidising re-agent such as an alkaline permanganate chromate
bichromate ferrate or chlorate and dilute sulphuric acid all substantially as and in the
manner hereinbefore specified.

page_text: 2 The conversion of American turpentine and other terpene oils into camphoric acid
by direct oxidation by the action of a current of warm dry air and steam and the
subsequent reduction of the camphoric acid to camphor by means of nascent hydrogen
all substantially as hereinbefore specified.
3 The conversion of American turpentine and other terpene oils into camphoric
acid by direct oxidation by the action of a current of warm dry air and steam and the
subsequent reduction of the camphoric acid to camphor by boiling it with three
equivalents of solid camphene in the presence of acetate of soda or formate of soda all
substantially as hereinbefore specified.
4 Converting turpentine or terpene oils into camphene by agitation with strong
sulphuric acid substantially as specified.
5 The processes for the production of artificial camphor hereinbefore specified.
Dated this 20th day of March 1899.
T. E. HALFORD,
Agent for Applicant.