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
Skeletal formula
Ball-and-stick model
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
  • InChI=1S/C12H11N3/c13-10-6-8-12(9-7-10)15-14-11-4-2-1-3-5-11/h1-9H,13H2/b15-14+ checkY
    Key: QPQKUYVSJWQSDY-CCEZHUSRSA-N checkY
  • InChI=1/C12H11N3/c13-10-6-8-12(9-7-10)15-14-11-4-2-1-3-5-11/h1-9H,13H2/b15-14+
    Key: QPQKUYVSJWQSDY-CCEZHUSRBB
  • N(=N/c1ccc(N)cc1)\c2ccccc2
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
Occupational safety and health (OHS/OSH):
Main hazards
 Highly toxic
Cancer suspect agent
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
0
2
1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
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 initially implicated in the 1981 Spanish Toxic Oil Syndrome (TOS), although further study suggested the cause was likely contaminated tomatoes.[2]

The initial theory of the incident proposed that 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. At the time, rapeseed oil was not legal for import for cooking use in Spain. However, the company (or smaller merchants) was accused of distilling the oil to remove the dye and selling it to households, possibly as much more valuable olive oil for cooking. Patients presented with 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 debate; later forensic evidence suggests that organophosphate poisoning from locally-grown vegetables may be a more likely cause of the symptoms.[3][4]


References
  1. "Vital staining for protozoa".
  2. "The Spanish cooking oil scandal". TheGuardian.com. 24 August 2001.
  3. "FSE Editorial". Archived from the original on 2007-03-12. Retrieved 2006-02-02.
  4. Woffinden, Bob (24 August 2001). "Cover-up". The Guardian. Retrieved 28 March 2023.
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