Aniline Yellow


Aniline Yellow
Aniline Yellow
Identifiers
CAS number 60-09-3 YesY
PubChem 6051
ChemSpider 5828 YesY
EC number 200-453-6
KEGG C19187 YesY
ChEBI CHEBI:233869 YesY
ChEMBL CHEMBL83761 YesY
Jmol-3D images Image 1
Properties
Molecular formula C6H5N=NC6H4NH2
Molar mass 197.24 g/mol
Melting point

123-126 °C

Boiling point

> 360 °C

Hazards
Main hazards Highly toxic
Cancer suspect agent
NFPA 704
NFPA 704.svg
2
0
1
 YesY Yellow (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.[1]

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.

Uses

Aniline Yellow is used in microscopy for vital staining,[2] in pyrotechnics for yellow colored smokes, in yellow pigments and inks including inks for inkjet 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 syndrome

Aniline 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.[3]

References


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