Aniline Yellow

Nitro-l-diazo-2-naphthol-4-sulfonic acid prefers the 2-position in spite of the nitro group, and increasing alkalinity favors ortho coupling with diazophenols. 1-Naphthalenesulfamic acid [24344-19-2] (ArNHSO H) and N-nitro-1-naphthylamine [4323-69-7] (ArNHNO ) couple exclusively in the para position. The substitution of resorcinol [108-46-3] and y -phenylenediamine [108-45-2] is compHcated and has been discussed (29,30). The first azo dyes from aniline, eg. Aniline Yellow [60-09-3] (19) (Cl Solvent Yellow 1 Cl 11000) were manufactured in 1861 and Bismark Brown [10114-58-6] (20) (Cl Basic Brown 1 Cl 21000) appeared in 1863. The reaction is as follows ... 

Colouring Matters.—In Italy butter may be coloured, but not with certain prohibited colouring matters, such as Martius yellow, Victoria yellow and metanil yellow. As a rule annatto is used, but sometimes also saffron or turmeric, and rarely carotin coal-tar colours (aniline yellow, butter yellow) are also employed. 

Other suitable diazo components are 4-nitroaniline (orange), 2,6-dichloro-4-(N,N-dimethylsulfamoy 1 )ani 1 ine (orange), 4-aminobenzophenone (yellow), 2,4,6-trichloro aniline (yellow), 2,4,6-tribromoaniline (yellow), 2,6-dibromo-4- nitro aniline (yellow-brown) [30], and 2-cyano-5- chloroaniline (orange). 

SYNS AAB AMINOAZOBENZENE p-AiMINOAZOBENZENE 4-AMINOAZOBENZENE 4-AMINO-l,l -AZOBENZENE p-AMINOAZOBENZOL 4-AMINOAZOBENZOL p-AMINODIPHENYLIMIDE . NILINE YELLOW 4-BENZENEAZOANILINE BRASILAZINA oil yellow G CERES YELLOW R C.I. 11000 C.I. SOLVENT BLUE 7 C.L SOLVENT YELLOW 1 FAST SPIRIT YELLOW AAB OIL SOLUBLE ANILINE YELLOW OIL YELLOW AAB ORGANOL YELLOW PARAPHENOLAZO ANILINE 4-(PHENYLAZO)ANILINE 4-(PHENYLAZO)BENZEN-AMINE p-PHENYLAZOPHENYLAMINE SOLVENT YELLOW 1 SUDAN YELLOW R USAF EK-1375... 

Aniline Yellow.—It is a dye known as aniline yellow and is of especial interest in being first azo dye used (1863), though it was first prepared by Griess in 1859, by the reaction just described (p. 570). At present it is not used as a dye to any extent. The hydrochloride salt is a beautiful violet colored substance which dissolves slightly in hot acids to a red colored solution. 

Bismarck Brown.—The dis-azo compound obtained meta-diamino benzene dis-azo benzene meta-di-amino benzene is a dye known as Bismark brown, though the dye is probably a mixture of the dis-azo compound and tri-amino azo benzene. With the exception of aniline yellow or amino azo benzene it was the first azo dye to be made. It was first prepared by Martins in 1864, and first made as a dye in 1866. 

Martius, by now a partner in the AGFA firm of Berlin, obtained a sample of chrysoidine (18) and handed it over to his consultant, A.W. Hofmann (Figure 11), for scientific investigation. In January 1877, Hofmann published details of the constitutions, as well as the methods of preparation, for 18, phenylene brown (15) and the related aniline yellow (16), much to the chagrin of Caro and his colleagues33-36. Soon it was shown that phenylene, or Bismarck brown (15), was in fact a bisazo compound 15a (Scheme 6). 

The amidoazobenzene hydrochloride came into the market formerly, as a yellow dye, under tire name of Aniline Yellow. At present, it is scarcely used, but there is prepared from it, by heating with sulphuric acid, a mono- or di-sulphonic acid, which in the form of its alkali salts finds application as a dye under the name of Acid Yellow, or Fast Yellow. As already mentioned under the dis-azo dyes, from the diazo-compound of this dye, Biebrich Scarlet may be made-by combination with /3-naphthol. Finally, the amidoazobenzene is still used for the preparation of the Induline dyes. 

Tropeolin 00 (also called orange IV, aniline yellow, or diphenyl orange) Schultz No. 97. Sodium salt of diphenylaminoazo-p-benzenesulfonic acid,... 

C.. Solvenf Yellow I p-(pheny[aZo)amline p-aminodiphen -ylimide aniline yellow C,. 11000. C12H,.Nj mol wt... 

Many colored compounds cannot be used as dyes on account of the fact that the color which they impart to wool or silk is readily removed by washing with water. In most cases, however, such compounds can be converted into dyes by introducing into them acidic or basic groups. Azobenzene, C6H5N=NC6H5, for example, is a bright-red compound, but does not possess the properties of a dye. The amino derivative of azobenzene, however, is a dye which is known as aniline yellow. 

Aniline Yellow, C6H5.N2.C6H4NH2.HCl, is the simplest azo-dye. As the color is fugitive it is not now used as a dye. It forms, however, the starting point in the preparation of other dyes, as it can be diazotized and coupled with amines or phenols. 

Butter Yellow, C6H5.N2.C6H4N(CH3)2, is the dimethyl derivative of aniline yellow. It is chiefly used for coloring butter and oils. 

Antimonic acid, HSbOg -1- 2H2O, has replaced arsenic acid in the manufacture of aniline yellow and aniline red. 

Aniline violet. See Basic violet 3 Aniline yellow. See p-Phenylazoaniline Anilinium chloride. See Aniline hydrochloride Anilinoacetic acid. See N-Phenyl glycine p-Anilinoaniline. See N-Phenyl-p-phenylenediamine... 

Aminoazobenzol p-Aminoazobenzol p-Aminodiphenylimide Aniline, p-(phenylazo) Aniline yellow... 

The diazo-compounds form the starting point of numerous organic compounds, including the azo-dyes, the first representative of which (amino-azobenzene hydrochloride, aniline yellow ) was prepared and shown to be a dye by Mene. What was called aniline yellow is the oxalate of aminoazo-benzene (CeH5 N N-CeH4 NH2), introduced as a dye by Simpson, Maule, and Nicholson in 1863 its constitution was established by C. A. Martius and Griess, and the isomeric change of diazoaminobenzene into aminoazobenzene was explained by Kekule. ... 

Peter Griess, a student of August Wilhelm v. Hofmann, living in England, discovered diazotization in 1857. In 1861, the first azo-dye, aniline yellow (Solvent Yellow 1) appeared on the market in England a further milestone in the development of azo-dyes was Congo red, a substantive dye discovered by Paul Bottiger in 1884. 

Azo compounds have the general formula R -N=N-R, where R and R are alkyl or aryl groups. Aromatic azo compounds are generally strongly colored and many are easily prepared via a so-called diazo coupling reaction, in which a diazonium cation is coupled with a relatively active (i.e., highly nucleophilic) arene such as a phenol or aniline. The dye called aniline yellow, for example, is prepared as follows ... 

Synonyms 4-(phenylazo)benzenamine C.I. Solvent Yellow 1 p-aminodiphenylimide Solvent Yellow 1 Aniline yellow C.I. 11000 p-(Phenylazo)aniline 4-amino-i,i -azobenzene p-aminoazobenzol 4-benzeneazoaniline paraphenolazo aniline p-phenylazopheny-lamine AAB aminoazobenzene Brasilazina Oil Yellow G Cellitazol R Ceres Yellow R C.I. Solvent Blue 7 fast Spirit Yellow fast Spirit Yellow AAB fat yellow AAB induline r oil-soluble Aniline Yellow oil yellow AAB Oil Yellow AN Oil Yellow B Oil Yellow R Organol Yellow Organol Yellow 2A Somalia Yellow 2G Stearix Brown 4R Sudan Yellow R Sudan Yellow RA 4-(phenylazo)-benzamine Uses as a dye for lacquer, varnish, wax products, oil stains and styrene resins in insecticides used as an intermediate in the manufacture of Acid Yellow, diazo dyes and indulines Cross para groups of compounds A... 

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