Improvements in the Manufacture or Production of Ortho- and Para- oxy-ortho-toluio Acids and Meta Cresol.
Year: 1894

page_text: Date of Application, 30th Aug., 1894
Complete Specification Left, 30th May, 1895-Accepted, 6th July, 1895
Improvements in the Manufacture or Production of Ortho- and Para-
oxy-ortho-toluio Acids and Meta Cresol.
I, GEORGE WILLIAM JOHNSON of 47 Lincoln's Inn Fields in the County of
London, Patent Agent do hereby declare the nature of this invention (which has
been communicated to me from abroad by Kalle & Co. of Biebrich-on-Rhine in the
Empire of Germany, Manufacturers) to be as follows:-
This invention relates to the manufacture or production of ortho- and para-oxy-
ortho-toluic-acids and of meta-cresol as a product of decomposition of the meta-
oxy-ortho-toluic-acids.
According to Armstrong and Wynue (Ber. d. d. chem. Ges. 1891, 24c, 718,
Proceedings of the Chemical Society 1890, 136) a trioxynaphthalene can be
obtained by melting the naphthalene-meta-disulpho acid with alkalies. My
foreign correspondents have found that if this process is performed at a sufficiently
high temperature, ortho-toluic-acid is produced together with acetic acid, one of
the two riugs of the naphthalene nucleus being destroyed.
Deen co
atca to me from abroad oy name & Co. 01 DIEDLICH ne in one
Empire of Germany, Manufacturers) to be as follows :—
This invention relates to the manufacture or production of ortho- and para-oxy-
ortho-toluic-acids and of meta-cresol as a product of decomposition of the meta-
oxy-ortho-toluic-acids.
According to Armstrong and Wynue (Ber. d. d. chem. Ges. 1891, 24c, 718,
Proceedings of the Chemical Society 1890, 136) a trioxynaphthalene can be
obtained by melting the naphthalene-meta-disulpho acid with alkalies. My
foreign correspondents have found that if this process is performed at a sufficiently
high temperature, ortho-toluic-acid is produced together with acetic acid, one of
the two riugs of the naphthalene nucleus being destroyed.
CO,H
00-00-00
OH
+ C₂O₁H₂
Instead of naphthalene meta disulpho-acid, all its derivatives can be employed
which contain in place of a sulpho group a NH, or OH group, that is, the alpha
naphthol-sulpho-acid (1.3) described in German Letters Patent No. 57910
and 64979, the alpha-naphthylamine-sulpho-acid (1.3) of the German Letters
Patent No. 64979, the beta-naphthol-sulpho-acid (2.4) obtained by heating under
pressure the beta naphthylamine-disulpho acid C of the German Letters
Patent 65997, and the beta naphthylamine-sulpho-acid (2.4) derived from the
corresponding naphthol-sulpho-acid.
If however the naphthylene-tri-sulpho-acids, which contain two sulpho groups in
the position 1 and 3 and the other one in the position 5, 6, 7 or 8 be melted with
alkalies, we obtain ortho-oxy-ortho-toluic acid or para oxy-ortho-toluic acid or
meta cresol, the latter being derived from meta oxy-toluic-acids which are inter-
mediately produced but decomposed in the melting process. The reaction takes
place in the same manner, if instead of the naphthalene-tri-sulpho-acids named
such acids are employed as are derived therefrom by substituting one group or
two groups SO,H by one or two groups OH or NH,.

page_text: 3) Meta cresol; by means of :—
a) Naphthalene-trisulpho-acid 1.3.6 of the German Letters Patent No. 38281,
alpha naphthol-trisulpho-acid 1.3.6 of the same Patent, or of
alpha naphthylamine di sulpho-acid 1.3.6 of the German Letters Patent
No. 27346,
meta-cresol being then a derivative of the meta oxy-ortho-toluic acid

page_text: 60 kilogrammes of napththalene trisulpho acid 1.3.5 obtained by treating the
naphthalene di sulpho-acid 1.5 with strong fuming sulphuric acid at a low
temperature are heated with 120 kilogrammes of caustic soda and 90 liters of
water for five hours under pressure at 280° Centigrade. The melt is then poured
into water, the solution is acidulated, boiled until the sulphurous acid has been
expelled and filtered. When the liquid has become cold the ortho-oxy-ortho-
toluic acid crystallizes out.
The melting point was found to be 143° Centigrade in contradiction to the
statements of Jacobsen. By heating with lime, ortho cresol is produced.
The acetyl derivative crystallizes in the shape of shining long needles melting
at 144° Centigrade.

page_text: EXAMPLE III.
PREPARATION OF META CRESOL.
60 kilogrammes of naphthalene trisulpho acid 1.3.6 are heated under pressure
for 5 hours at 280° Centigrade with 120 kilogrammes of caustic soda and 90 liters
of water. The completed melt is then acidulated and the meta cresol thus
produced is separated from a small quantity of ortho-toluic acid by distillation with
steam in the presence of soda.
Dated this 30th do of Anonst 1001
JOHNSONS & WILLCOX,
47 Lincoln's Inn Fields, Agents.
Improvements in the Manufacture or Production of Ortho- and Para-
oxy-ortho-toluic Acids and Meta Cresol.
I GEORGE WILLIAM JOHNSON of 47 Lincoln's Inn Fields in the County of
London, Patent Agent do hereby declare the nature of this invention (which has
been communicated to me from abroad by Kalle & Co. of Biebrich on Rhine in
the Empire of Germany Manufacturers) and in what manner the same is to be
performed to be particularly described and ascertained in and by the following
statement :-
This invention relates to the manufacture or production of ortho- and para-oxy-
ortho-toluic acids and of meta-cresol as a product of decomposition of the meta-
oxy-ortho-toluic-acids.
According to Armstrong and Wynne (Berichte der deutschen chemischen
Gesellschaft 1891, 24c, 718 Proceedings of the Chemical Society 1890, 136) a
trioxynaphthalene can be obtained by melting the naphthalene-meta disulpho-acid
with alkalies. My foreign correspondents have found that, if this process be
performed at a sufficiently high temperature, ortho-toluic-acid is produced together
with acetic acid or products of further decomposition of the latter, one of the two
rings of the naphthalene nucleus being destroyed.
Instead of napthalene-meta-disulpho-acid, all its derivatives can be employed
which contain in place of a sulpho group, a NH, or OH group i.e. the alpha
naphthol sulpho-acid (1.3) described in the Specification of German Letters
Patent No. 57910 and 64979, the alpha naphthylamine-sulpho-acid (1.3) of the
German Letters Patent No. 64979, the beta-naphthol-sulpho-acid (2.4) obtained
by heating under pressure the beta-naphthylamine-disulpho acid C. of the German
Letters Patent 65997, and the beta naphthylamine-sulpho-acid (2.4) derived from
the corresponding naphthol sulpho acid.
If however the naphthalene tri sulpho acids, which contain two sulpho groups in
the position 1 and 3 and the other one in the position 5. 6. 7 or 8 be melted with

page_text: alkalies there are obtained ortho-oxy-ortho-toluic acid or para-oxy-ortho-toluic-acid
or meta cresol, the latter being derived from meta-oxy-toluic-acids which are
intermediately produced but decomposed in the melting process.
The reaction
takes place in the same manner, if instead of the naphthalene-tri-sulpho-acids
named such acids are employed as are derived therefrom by substituting one group
or two groups SO,H by one group or two groups OH or NH.
In this way are obtained
1) Ortho-oxy-ortho-toluic-acid by means of naphthalene-trisulpho-acid 1.3.5,
produced by sulphonation of naphthalene disulpho-acid 1.5, or of beta-naphthyl-
amine-disulpho-acid C. (2.4.8) of the German Letters Patent No. 65997

page_text: or of alpha-naphthol-disulpho acid 1.6.8 produced by heating under pressure the
alpha-naphthylamine trisulpho acid 1.4.6.8

page_text: of water. The completed melt is then acidulated and the meta-cresol thus
produced, is separated from a small quantity of ortho-toluic-acid by distillation
with steam in the presence of soda.
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 :-
I. The manufacture of ortho-oxy-ortho-toluic-acid by melting naphthalene tri-
sulpho acid 1.3.5 or naphthol or naphthylamine disulpho acids or dioxy-naphthalene
or amido naphthol mono sulpho acids, which contain the substituting sulpho oxy or
amido groups in the 1.3.5 position with caustic alkali at a high temperature in
either open or closed vessels.
II. The manufacture of para-oxy-ortho toluic-acid by melting naphthalene
trisulpho acid 1.3.7 or naphthol or naphthylamine disulpho acids or dioxy or
amidonaphthol mono sulpho acids, which contain the substituting sulpho oxy or
amido groups in the 1.3.7 position with caustic alkali at a high temperature in either
open or closed vessels.
III. The manufacture of meta cresol by melting naphthalenetrisulpho acid 1.3.6
or naphthol or naphthylamine disulpho acids or dioxy or amido naphthol mono-
sulpho acids, which contain the substituting sulpho oxy or amido groups in the 1.3.6
position with caustic alkali at a high temperature in either open or closed vessels.
Dated this 30th day of May 1895.
JOHNSONS & WILLCOX,
Agents.