Aniline Yellow

Aniline Yellow is a yellow azo dye and an aromatic amine. It is a derivative of azobenzene. It has the appearance of an orange powder. 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
Names
Preferred IUPAC name
4-(Phenyldiazenyl)aniline
Other names
para-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
C.I. 11000
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.412
EC Number
  • 200-453-6
KEGG
UNII
Properties
C6H5N=NC6H4NH2
Molar mass 197.24 g/mol
Melting point 123 to 126 °C (253 to 259 °F; 396 to 399 K)
Boiling point > 360 °C (680 °F; 633 K)
-118.3·10−6 cm3/mol
Hazards
Main hazards Highly toxic
Cancer suspect agent
NFPA 704 (fire diamond)
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelHealth code 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
0
1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Uses

Aniline Yellow is used in microscopy for vital staining,[1] 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.[2]

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References
  1. http://www.microscopy-uk.org.uk/mag/artfeb00/rhvital.html
  2. "Archived copy". Archived from the original on 2007-03-12. Retrieved 2006-02-02.CS1 maint: archived copy as title (link)
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