GB480551A - Process for the preparation of nitro and amino derivatives and of dyestuffs desired therefrom - Google Patents

Process for the preparation of nitro and amino derivatives and of dyestuffs desired therefrom

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Publication number
GB480551A
GB480551A GB6517/37A GB651737A GB480551A GB 480551 A GB480551 A GB 480551A GB 6517/37 A GB6517/37 A GB 6517/37A GB 651737 A GB651737 A GB 651737A GB 480551 A GB480551 A GB 480551A
Authority
GB
United Kingdom
Prior art keywords
benzoylamino
nitro
ether
chloro
amino
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB6517/37A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kuhlmann SA
Original Assignee
Kuhlmann SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kuhlmann SA filed Critical Kuhlmann SA
Publication of GB480551A publication Critical patent/GB480551A/en
Expired legal-status Critical Current

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Abstract

Nitro compounds of the general formula <FORM:0480551/IV/1> where R is any hydrocarbon radicle and R1 and R2 are aromatic radicles, substituted or not, are manufactured by condensing a nitro-halogen compound of the general formula <FORM:0480551/IV/2> with a salt, preferably an alkali salt, of a phenolic compound, preferably in the presence of an excess of free phenol. The corresponding amino compounds are manufactured by reducing the nitro compounds. In examples: (1) caustic potash is heated with excess of phenol until the water formed is removed, and the product is heated with 2-benzoylamino-4-chloro-5-nitrodiphenyl ether; the product is reduced to the diphenyl ether of 2-benzoylamino-5-aminohydroquinone, which may be diazotized; (2) p-cresol is used in place of the phenol in (1), producing 2-amino-3-(41-methyl)-phenoxy - 5 - benzoylamino - 6 - phenoxy-benzene. Samples have been furnished under Sect. 2 (5) of: (A) 2-nitro-5-acetylaminohydroquinone diphenyl ether, prepared by acetylating 2-amino 4-chlorodiphenyl ether, nitrating the product and condensing the nitro derivative with potassium phenolate in the presence of excess of phenol; (B) the corresponding amine, prepared by reduction of the nitro compound with zinc powder and glacial acetic acid; (C) and (D) 2 - acetylamino - 5 - nitro - and - 5 - amino - 1 - (41 - methyl) - phenoxy - 4 - phenoxybenzene, prepared analogously to (A) and (B) by starting from 4 - methyl - 21 - amino - 41 - chlorodiphenyl ether. Nitro-halogen compounds of the general formula given above are obtainable by acylating the corresponding aminohalogendiphenyl ethers and nitrating the products, e.g. by the action of nitric acid, alone or in the presence of a solvent, e.g. chlorobenzene or acetic acid. For example, 2 - benzoylamino - 4 - chloro - 5 - nitrodiphenyl ether is prepared by benzoylating 2-amino-4-chlorodiphenyl ether and treating the product with nitric acid in the presence of glacial acetic acid. Azo dyes, forming upon the material.-Cotton is dyed by coupling on the fibre the diazo compounds of the amines described above, other than those in which R is a cyclic radicle at least partially hydrogenated, with arylamides of 2 : 3-hydroxynaphthoic or acetoacetic acid. In an example, cotton is padded with 2 : 3-hydroxynaphthoic a -naphthylamide and a reddish violet dyeing is developed with diazotized 2 - benzoylamino - 5 - aminohydroquinone diphenyl ether. A table gives the shades obtained by using as coupling component the anilide, m-nitranilide, 5-chloro-o-toluidide, b -naphthylamide, o- and p-anisidide, o-toluidide, p-chloro-o-anisidide and 4 : 6-dimethoxy - 5 - chloranilide of 2 : 3-hydroxynaphthoic acid, and diacetoacetyl-o-tolidine. Specifications 17279/13 and 303,838 [both in Class 15 (ii)], are referred to. The Specification as open to inspection under Sect. 91 comprises the manufacture of the dyestuffs in substance or on vegetable fibres in general, using any coupling components of substantive character. It contains also additional examples describing the production of 2 - benzoylamino - 4 - o - tolyloxy - 5 - nitrodiphenyl ether, and its 21 - chloro-derivative, 21 - chloro - 2 - benzoylamino - 4 - phenoxy - 5 - nitrodiphenyl ether, 2 - benzoylamino - 4 - o - chlorophenoxy-5-nitrodiphenyl ether and its 21-chloro-derivative, and the corresponding amines. A table gives the shades obtained by diazotizing these amines and also 2-benzoylamino - 4 - tolyloxy - 5 - aminodiphenyl ether, and coupling with the components specified above, and with b - hydroxynaphthoylamino - 3 - chloro - 4 : 6 - dimethoxybenzene. This subject-matter does not appear in the Specification as accepted.
GB6517/37A 1936-03-05 1937-03-05 Process for the preparation of nitro and amino derivatives and of dyestuffs desired therefrom Expired GB480551A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR480551X 1936-03-05

Publications (1)

Publication Number Publication Date
GB480551A true GB480551A (en) 1938-02-24

Family

ID=8903476

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6517/37A Expired GB480551A (en) 1936-03-05 1937-03-05 Process for the preparation of nitro and amino derivatives and of dyestuffs desired therefrom

Country Status (1)

Country Link
GB (1) GB480551A (en)

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