Aromatic amine

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An aromatic amine is an amine with an aromatic substituent—that is -NH2, -NH- or nitrogen group(s) attached to an aromatic hydrocarbon, whose structure usually contains one or more benzene rings. Aniline is the simplest example.

Aromatic amines, when protonated, usually have lower pKas (are more acidic) than their non-aromatic analogs. This is due to the delocalization of the lone pair of electrons from the nitrogen into the ring.

Representative anilines
Aromatic amine CAS number Properties Uses
Aniline Aniline 62-53-3
o-Toluidine o-toluidine 95-53-4
2,4,6-Trimethylaniline 2,4,6-Trimethylaniline.svg 88-05-1
Anisidine Anisidine 90-04-0
3-Trifluoromethylaniline 3-trifluoromethylaniline 98-16-8 Intermediate for herbicides, metabolite
N-Methylaniline N-methylaniline 100-61-8

The general population is exposed to aromatic amines through the diet (e.g. pesticides), pharmaceuticals (e.g. prilocain), hair dyes, smoking, and diesel engine exhaust, as well as through occupational exposure at the workplace (e.g. rubber, textiles, dye industries).[1]

Aromatic amines in textiles[edit]

Since August 2012, the new standard EN 14362-1:2012 Textiles - Methods for determination of certain aromatic amines derived from azo colorants - Part 1: Detection of the use of certain azo colorants accessible with and without extracting the fibres is effective. It had been officially approved by the European Committee for Standardization (CEN) and supersedes the test standards EN 14362-1: 2003 and EN 14362-2: 2003.

The standard describes a procedure to detect EU banned aromatic amines derived from azo colorants in textile fibres, including natural, man-made, regenerated, and blended fibres. The standard is also relevant for all coloured textiles, e.g. dyed, printed, and coated textiles.[2]

See also[edit]

References[edit]

  1. ^ Exposure to Aromatic Amines - Overview on Chemistry Presentation by A. Seidel (2009), Retrieved 09/24/2012
  2. ^ New European Standard for Aromatic Amines Derived from Azo Colorants SGS SafeGuard Bulletin, Retrieved 09/24/2012