KIMIA ORGANIKKELOMPOK ANILINE YELLOW

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ANILINE YELLOW

Aniline Yellow is a yellow azo dye and an aromatic amine. It is a derivate of azobenzene. It has the appearance of an orange powder. It is a carcinogen.

Aniline Yellow was the first azo dye. It was first produced in 1861 by C. Mene. The second azo dye was Bismarck Brown in 1863. Aniline Yellow was commercialized in 1864 as the first commercial azo dye, a year after Aniline Black. It is manufactured from aniline.

Aniline Yellow

Molecular formula• C6H5N=NC6H4NH2

Anilin yellow / 25 grams

ANILINE YELLOWIUPAC NAME4-PHENYLDIAZENYLANILINE

Other namespara-aminoazobenzene, 4-phenylazoaniline, AAB, Brasilazina oil Yellow G, Ceres Yellow, Fast spirit Yellow, Induline R, Oil Yellow AAB, Oil Yellow AN, Oil Yellow B, Oil Yellow 2G, Oil Yellow R, Organol Yellow, Organol Yellow 2A, Solvent Yellow, Somalia Yellow 2G, Stearix Brown 4R, Sudan Yellow R, Sudan Yellow RA

UsesAniline Yellow is used

in microscopy for vital staining,

in pyrotechnics for yellow colored smokes, in yellow pigments and inks including inks forinkjet printers.

It is also used in insecticides, lacquers, varnishes, waxes, oil stains, and styrene resins.

It is also an intermediate in synthesis of other dyes, e.g. chrysoidine, indulines, Solid Yellow, and Acid Yellow.

Toxic Oil SyndromeAniline Yellow was involved in the 1981 Spanish Toxic Oil Syndrome (TOS). A Madrid-based company imported denaturated rapeseed oil, dyed by aniline yellow to mark it as unsuitable for human consumption, to be used as a fuel in steel mills. However, the company distilled the oil to remove the dye, and sold it as a much more valuable olive oil for cooking. The result was a rash of pneumonia-type illnesses, with a second stage with lesions, weight loss, paralysis, and muscle wasting.The net result was over 20,000 sick and 400 dead. The chemistry of the poisonous reaction is still subject of a debate.

AZO COUPLING

An azo coupling is an organic reaction between a diazonium compound and another aromatic compound that produces an azo compound. In this electrophilic aromatic substitution reaction, the aryldiazonium cation is theelectrophile and the activated arene is a nucleophile. In most cases, including the examples below, the diazonium compound is also aromatic.

Uses of the Reaction The product will absorb longer wavelengths of

light (specifically they absorb in the visible region) than the reactants because of increased conjugation. Consequently, aromatic azo compounds tend to be brightly colored due to the extended conjugated systems. Many are used as dyes (see azo dye). Important azo dyes include methyl red andpigment red 170.

Azo coupling is also used to produce prontosil and other sulfa drugs.

Examples of Coupling Reactions

Many procedures have been described. The related dye called aniline yellow is

produced from the reaction of aniline and the diazonium salt.

Aniline Yellow (amino Azobenzene) as a Dye

This is another azodye and has little value as a dye. This is because it is sensitive to acids. This is the simplest basic azo dye. This can be obtained by coupling benzene diazomium chloride with aniline.

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