IMPROVEMENTS IN THE PRODUCTION OF CERTAIN SUBSTANCES FOR USE IN OBTAINING COLORING PROVISIONAL SPECIFICATION
Year: 1883

page_text: LETTERS PATENT to Robert Holliday of the firm of Read Holliday & Sons of
Huddersfield in the County of York Manufacturing Chemists and William
Richard Hodgkinson of 29 Pembroke Squaro Kensington in the County of
Middlesex, Professor of Chemistry. for an Invention of IMPROVEMENTS IN THE
PRODUCTION OF CERTAIN SUBSTANCES FOR USE IN OBTAINING COLORING
PROVISIONAL SPECIFICATION left by the said Robert Holliday and William
Richard Hodgkinson at the Ollico of the Commissioners of Patents on the
31st July 1883.
ROBERT HOLLIDAY of the firm of Read Holliday & Sons of Huddersfield in the
County of York Manufacturing Chemists and WILLIAM RICHARD HODGKINSON
of 29. Pembroke Square Kensington in the County of Middlesex Professor of
Chemistry IMPROVEMENTS IN THE PRODUCTION OF CERTAIN SUBSTANCES FOR USE
IN OBTAINING COLORING MATTERS SUITABLE FOR DYEING AND PRINTING.
The improvements relate to the treatment of Fluorines and of a substance
commonly known as Acenapthene
In carrying out our improvements whether by the use of Fluorines or of the
substance commonly known as Acenapthene we convert the substance under
operation first into a mono-sulphonic acid, we then convert such mono-sulphonic
acid into a phenole by fusion thereof with caustic alkali (Potash or soda)
The products obtained are then dissolved in water and neutralised by an acid.
such as sulphuric or hydro chloric acid. The resulting product is partly dissolved
and partly thrown down or precipitated.
The precipitation may then be completed by the addition of any soluble salt such
as chloride of sodium (common salt)
By these means we obtain crude fluorol which if desired may be further purified
by crystalization from the action thereon of water or steam distillation preferably
hot water such fluorol we employ in the production of azo-colors

page_text: The fluorols and their sulpho-acids may be employed in a similar way to
that adopted in the use of napthols or their sulpho-acids for the formation of azo
colors.
From the before mentioned substances viz fluorines and accnapthene we also
obtain fluorylamines by treating the said substance by means of nitric acid or nitric
and sulphuric acids together or in such manner as to form a mono-nitro product
which product is then reduced in the usual manner of reducing such nitro
compounds into their corresponding amido compounds, these reduction products
from the aforesaid nitro-fluorines we term fluorylamines
These fluorylamines may be purified by distillation.
The fluorylamines and their sulpho-acids may be employed for the production
of azo colors in a similar way to the napthylamines and their sulpho acids or
otherwise.

page_text: SPECIFICATION in pursuance of the conditions of the Letters Patent filed by
the said Richard Holliday and William Kichard Hodgkinson in the Patent
Office on the 29th January 1884.
ROBERT HOLLIDAY of the firm of Read, Holliday & Sons of Huddersfield in the
County of York Manufacturing Chemists and WILLIAM RICHARD HODGKINSON
of 29. Pembroke Square Kensington in the County of Middlesex Professor of
Chemistry "IMPROVEMENTS IN THE PRODUCTION OF CERTAIN SUBSTANCES FOR
USE IN OBTAINING COLORING MATTERS SUITABLE FOR DYEING AND PRINTING."
The improvements relate to the treatment of Fluorenes and of a substance
commonly known as Acenapthene
In carrying out our improvements whether by the use of Fluorenes or of the
substance commonly known as Aconapthene we convert the substance under
operation first into a mono-sulphonic acid, we then convert such mono-sulphonic
acid into a phenole by fusion thereof with caustic alkali (Potash or Soda) raising
the temperature until by examining samples from time to time and applying a test
for fluorol its presence is evident
We have named mono-sulphonic acid as the particular example of sulphonic acid
for operation because that gives the best results and although other forms such as
di-sulphonic acid might be submitted to the same reaction the results would not be
so good
The products obtained are then dissolved in water and neutralized by an acid
such as sulphuric or hydrochloric acid. The resulting product is partly dissolved
and partly thrown down or precipitated and at this stage precipitation is practically
complete.
If the precipitation be desired to be completed it may be effected by the addition
of any soluble salt such as chloride of sodium (common salt).
As in most manipulations with sulphuric acid it will be found that the sulpho-
nations of these bodies will be effected more slowly when operating with cold
sulphuric acid than when employing heat in aid thereof.
By these means we obtain crudo fluorol which if desired may be further purified
by crystalization from the action thereon of water or steam distillation preferably
hot water such fluoral we employ in the production of azo colors.
The fluorols and their sulpho-acids may be employed in a similar way to
that adopted in the use of napthols or their sulpho-acids for the formation of
azo colors.
The description of Fluorene which we employ is that which is obtained from the
crude produce or fluorene boiling between 270° and 320° C.
From the before mentioned substances, viz, fluorenes and acenapthene we also
obtain fluorylamines by treating the said substance by means of nitric acid or nitric
and sulphuric acid together or in such manner as to form a mono-nitro product
which product is then reduced in the usual manner of reducing such nitro
compounds into their corresponding amido compounds, these reduction products
from the aforesaid nitro-fluorenes we term fluorylamines.
These fluorylamines may be purified by distillation
The fluorylamines and their sulpho acids may be employed for the production
of azo colors in a similar way to the napthylamines and their sulpho acids or
otherwise.
As an example of the treatment of Fluorene to obtain Fluorylamine and when
operating on Fluorene of a description having a inelting point of say between 90°
to 110° C and treating the same with ordinary commercial nitric acid of about 1.3

page_text: :
specific gravity at about the temperature of boiling water we have found a mono-
nitro-fluorene of good marketable quality to be produced.
The relative proportions of the fluorene and nitric acid under the circumstances
stated would be in about their molicular proportions.
The reductions of these nitro fluorenes having been effected in the usual manner
they then constitute the products which we call fluorylamines
In the caso of an operator adopting for treatment the body known as
Acenapthene he will find that the conditions above given for Fluorene will apply
equally well
What we claim as our invention is
1. The production of Fluorol from Fluorene or acenapthene by converting the
'fluorene into mono sulphonate and then into a phenole by fusion as set forth..
2. The production of Fluorylamines by treating fluorenes or acenapthene by means
of nitric acid or a mixture of nitric acid and sulphuric acid or in other suitable
manner to produce nitro compounds therefrom and the reduction of those nitro
compounds into their corresponding amido compounds for uso in obtaining coloring
matters for dyeing and printing substantially as set forth
:
In witness whereof we the said Robert Holliday and William Richard Hodgkinson
have hereunto set our hands and seals this twenty eighth day of January in the
year of our Lord One thousand eight hundred and eighty four.
RUBE
(12.8.)
WILLIAM RICHARD HODGKINSON (LS.)