GB626661A - An improved method of introducing an amino group into the nucleus of an aromatic compound - Google Patents
An improved method of introducing an amino group into the nucleus of an aromatic compoundInfo
- Publication number
- GB626661A GB626661A GB2638846A GB2638846A GB626661A GB 626661 A GB626661 A GB 626661A GB 2638846 A GB2638846 A GB 2638846A GB 2638846 A GB2638846 A GB 2638846A GB 626661 A GB626661 A GB 626661A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxylamine
- sulphate
- acid
- compounds
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/503—Amino-hydroxy-anthraquinones; Ethers and esters thereof unsubstituted amino-hydroxy anthraquinone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/02—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of hydrogen atoms by amino groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/22—Dyes with unsubstituted amino groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Aromatic compounds in sulphuric acid solution are nuclearly aminated by heating with hydroxylamine, a salt thereof, or a salt of hydroxylamine disulphonic acid with a metal compound wholly dissolved in the sulphuric acid as catalyst. Preferably the quantity of sulphuric acid should be about ten times the weight of the aromatic compound used and the temperature below 100 DEG C. Metal compounds instanced are those of vanadium, molybdenum, titanium and iron and the metal may occur in the anion or kation, e.g. vanadyl sulphate or ammonium vanadate. Mixtures of the metal compounds with thorium, zirconium or mercury compounds may be used and at low temperatures vanadium compounds are the most effective. The products are dyes or dyestuffs intermediates and for a list of compounds treated and illustrative examples see the Group IV (c) abridgment. Specifications 204,241, 279,205, 280,652, [all in Class 2 (iii)], 348,159 and 564,610 are referred to. Reference has been directed by the Comptroller to Specification 585,560.ALSO:Aromatic compounds in sulphuric acid solution are nuclearly aminated by heating with hydroxylamine, a salt thereof, or a salt of hydroxylamine disulphonic acid with a metal compound wholly dissolved in the sulphuric acid as catalyst. Preferably the quantity of sulphuric acid should be about ten times the weight of the aromatic compound used and the temperature below 100 DEG C. Metal compounds instanced are those of vanadium, molybdenum, titanium and iron, and the metal may occur in the anion or cation, e.g. vanadyl sulphate or ammonium vanadate. Mixtures of the metal compounds with thorium, zirconium or mercury compounds may be used and at low temperatures vanadium compounds are the most effective. In examples: (1) the effect of different times of heating, temperatures, proportions of sulphuric acid and catalyst, e.g. vanadyl sulphate, ammonium vanadate, ferrous sulphate, molybdenic acid and titanium dioxide, is shown on the reaction of anthraquinone with hydroxylamine sulphate or an equimolar quantity of an alkali metal salt of hydroxylamine disulphonic acid. The main products are a - and b -amino-anthraquinone, high temperatures favouring the production of the former. The use of ferrous sulphate results in smaller yields; (2) benzene with hydroxylamine sulphate and 9a) ferrous sulphate yields mixed metanilic, orthanilic and sulphanilic acids and with (b) vanadyl sulphate mainly metanilic acid with some mixed meta-diamino-benzene-sulphonic acids including 1,3-diamino-benzene-5-sulphonic acid. Naphthalene with hydroxylamine and vanadyl sulphates yields mixed naphthylamine sulphonic acids at 100 DEG C., which are converted to quinono-imide compounds at higher temperatures. Anthracene and phenanthrene with hydroxylamine sulphate and molybdenic acid at 100 DEG C. give mixtures of amino-anthracene- or amino-phenanthrenesulphonic acids respectively, which at higher temperatures are converted to quinonoid compounds; (3) benzanthrone with vanadyl sulphate and hydroxylamine sulphate or an equivalent quantity of potassium hydroxylamine di-sulphonate yields 3-amino-benzanthrone which on fusion with potassium hydroxide gives a black dyestuff. Similarly benzo-phenone yields mixed amino-benzophenones, mainly the metaamino-isomer with some of the para, which on coupling with the anilide of 2,3-b -hydroxynaphthoic acid give an orange dye; (4) alizarin, anthrarufine, sulphonated anthrarufine, and (6) azobenzene with vanadyl and hydroxylamine sulphates yield mainly a -amino-alizarin, a reddish-blue mordant dyestuff, a reddish-blue acid dyestuff and mixed amino-azo-benzenes respectively; (5) dibenzanthrone, isodibenzanthrone, flavanthrone, indanthrone and tetrabromindigo with vanadyl sulphate or molybdenic acid and varying molar proportions of hydroxylamine used as its sulphate or alkali metal disulphonate gives the correspondingly aminated but not sulphonated dyestuff which, except for that derived from tetra-bromindigo, is fast to chlorine after treatment with chlorine water or hypochlorite; (7) nitrobenzene and (8) dimethylaniline with molybdenic acid or vanadyl sulphate and hydroxylamine sulphate yield ortho-nitraniline and some nitro-diamino derivatives and mixed amino-dimethylanilines with the ortho-isomer predominating respectively. The mixed amino-dimethylanilines form a brown azo dyestuff with b -naphthol. It is also stated that amino groups may be introduced into a -nitro-naphthalene, a -chloro-1-nitroanthraquinone, 1,5- or 1,8-dinitro-anthraquinone, 1-nitro-anthraquinone-a -sulphonic acid, into azo dyes obtained on diazotization of nitroanilines, nitrotoluidines, and o-, m-, and p-nitro-anisidine, and into triphenylmethane and sulphur dyes such as dehydro-thio-p-toluidine or its sulphonic acid. Specifications 204,241, 279,205, 280,652, [all in Class 2 (iii)], 348,159 and 564,610 are referred to. Reference has been directed by the Comptroller to Specification 585,560.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2638846A GB626661A (en) | 1946-09-02 | 1946-09-02 | An improved method of introducing an amino group into the nucleus of an aromatic compound |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2638846A GB626661A (en) | 1946-09-02 | 1946-09-02 | An improved method of introducing an amino group into the nucleus of an aromatic compound |
Publications (1)
Publication Number | Publication Date |
---|---|
GB626661A true GB626661A (en) | 1949-07-19 |
Family
ID=10242851
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2638846A Expired GB626661A (en) | 1946-09-02 | 1946-09-02 | An improved method of introducing an amino group into the nucleus of an aromatic compound |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB626661A (en) |
-
1946
- 1946-09-02 GB GB2638846A patent/GB626661A/en not_active Expired
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