Year: 1894

page_text: Date of Application, 16th June, 1894
Complete Specification Left, 18th Mar., 1895-Accepted, 27th Apr., 1895
4
I, OLIVER IMRAY, of No. 28 Southampton Buildings, Chancery Lane, in the
County of London, Chartered Patent Agent, do hereby declare the nature of this
invention to be as follows:-
-
My correspondents have found that the alkylesters of paraoxyphenylurea can be
easily made from paraoxyphenylurea, whereas all the methods known up to the
present time start from the alkyl ethers of paraamidophenol. The present
invention consists in the treatment of paraoxyphenylurea with alkyl halogenides
and caustic alkalies or their substitutes such as the alkaline earths, ammonia, oxide
of lead, alkaline carbonates &c.
The manufacture may for example be carried out in the following manner.
1) 680 grammes of paraoxyphenylurea are dissolved in 2.5 litres of alcohol and
the solution is mixed with 300 grammes of caustic potash dissolved in 1 litre of
water, after which 900 grammes of ethyl iodide are added. After boiling for two
hours the greater part of the alcohol is distilled off, and, on cooling, the para-
ethoxyphenylurea crystallises out.
2) 15 parts by weight of paraoxyphenylurea are heated with 100 parts by
weight of water, 7 parts by weight of potash, 60 parts by weight of alcohol and
11 parts by weight of ethylbromide, in a closed vessel under pressure to a
temperature of from 60 to 75° C. for five hours. On cooling, the greater part of
the ethylated urea crystallises out.
By distilling off the alcohol from the mother liquor, a further quantity of
paraphenetolurea is obtained.
3) 15 parts by weight of p-oxyphenylurea are heated with 100 parts by weight
of water, 16 parts by weight of crystallised barium hydrate, 60 parts by weight of
alcohol and 11 parts by weight of ethyl bromide for five hours in a vessel with an
inverted condenser.
The isolation of the p-phenetolcarbamide formed is effected according to
Example 2.
Instead of ethylbromide, ethylchloride and ethyliodide may be employed.
By employing the methylhalogenides in place of the ethyl compounds p-anisolurea
is obtained.
Dated this 16th day of June 1894.
ABEL & IMRAY,
Agents for the Applicant.

page_text: COMPLETE SPECIFICATION.
Improved Manufacture of Para-methoxy and Para-ethoxy-
phenylurea.
†, OLIVER IMRAY, of No. 28, Southampton Buildings, Chancery Lane, in the
County of London, Chartered Patent Agent, 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 :-
My correspondents have found that the alkylesters of paraoxyphenylurea can be
easily made from paraoxyphenylurea, whereas all the methods known up to the
present time start from the alkyl ethers of paraamidophenol. The present
invention consists in the treatment of paraoxyphenylurea with alkyl halogenides
and caustic alkalies or their substitutes such as the alkaline earths, ammonia, oxide
of lead, alkaline carbonates &c.
The manufacture may for example be carried out in the following manner.
1) 680 grammes of paraoxyphenylurea are dissolved in 2-5 litres of alcohol and
the solution is mixed with 300 grammes of caustic potash dissolved in 1 litre of
water, after which 900 grammes of ethyl iodide are added. After boiling for two
hours the greater part of the alcohol is distilled off, and, on cooling, the para-
ethoxy-phenylurea crystallises out.
2) 15 parts by weight of paraoxyphenylurea are heated with 100 parts by
weight of water, 7 parts by weight of potash, 60 parts by weight of alcohol and
11 parts by weight of ethylbromide, in a closed vessel under pressure to a
temperature of from 60 to 75° C. for five hours. On cooling, the greater part of
the ethylated urea crystallises out.
By distilling off the alcohol from the mother liquor, a further quantity of
paraphenetolurea is obtained.
3) 15 parts by weight of p-oxyphenylurea are heated with 100 parts by weight
of water, 16 parts by weight of crystallised barium hydrate, 60 parts by weight of
alcohol and 11 parts by weight of ethyl bromide for five hours in a vessel with an
inverted condenser.
The isolation of the p-phenetolcarbamide formed is effected according to
Example 2.
Instead of ethylbromide, ethylchloride and ethyliodide may be employed.
By employing the methylhalogenides in place of the ethyl compounds p-anisolurea
is obtained.
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 :-
The herein described manufacture of p-methoxy and p-ethoxyphenylurea, by
treating para-oxyphenylurea in alcoholic solution or aqueous alcoholic solution
with the equivalent quantity of caustic alkalies or their substitutes, such as the
alkaline earths, ammonia, oxide of lead, or alkali carbonates and with the halogen
compounds of methyl and ethyl.
Dated this 18th day of March 1895.
ABEL & IMRAY,
Agents for the Applicant.