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Azo compound

Azo compounds are compounds bearing the functional group R−N=N−R′, in which R and R′ can be either aryl or alkyl. IUPAC defines azo compounds as: "Derivatives of diazene (diimide), HN=NH, wherein both hydrogens are substituted by hydrocarbyl groups, e.g. PhN=NPh azobenzene or diphenyldiazene." The more stable derivatives contain two aryl groups. The N=N group is called an azo group. The name azo comes from azote, the French name for nitrogen that is derived from the Greek (a-, "not") + (zōē, life). Many textile and leather articles are dyed with azo dyes and pigments.

Aryl azo compounds

Aryl azo compounds are usually stable, crystalline species. Azobenzene is the prototypical aromatic azo compound. It exists mainly as the trans isomer, but upon illumination, converts to the cis isomer. Aromatic azo compounds can be synthesized by azo coupling, which entails an electrophilic substitution reaction where an aryl diazonium cation is attacked by another aryl ring, especially those substituted with electron-donating groups: + Ar′H → ArN=NAr′ + H+ Since diazonium salts are often unstable near room temperature, the azo coupling reactions are typically conducted near ice temperatures. The oxidation of hydrazines (R−NH−NH−R′) also gives azo compounds. Azo dyes are also prepared by the condensation of nitroaromatics with anilines followed by reduction of the resulting azoxy intermediate: ArNO2 + Ar′NH2 → ArN(O)=NAr′ + H2O ArN(O)=NAr′ + C6H12O6 → ArN=NAr′ + C6H10O6 + H2O For textile dying, a typical nitro coupling partner would be disodium 4,4′-dinitrostilbene-2,2′-disulfonate. Typical aniline partners are shown below.Klaus Hunger, Peter Mischke, Wolfgang Rieper, Roderich Raue, Klaus Kunde, Aloys Engel: "Azo Dyes" in Ullmann’s Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim.. As a consequence of п- delocalization, aryl azo compounds have vivid colors, especially reds, oranges, and yellows. Therefore, they are used as dyes, and are commonly known as azo dyes, an example of which is Disperse Orange 1. Some azo compounds, e.g., methyl orange, are used as acid-base indicators due to the different colors of their acid and salt forms. Most DVD-R/ +R and some CD-R discs use blue azo dye as the recording layer. The commercial success of azo dyes motivated the development of azo compounds in general.

Alkyl azo compounds

Aliphatic azo compounds (R and/or R′ = aliphatic) are less commonly encountered than the aryl azo compounds. A commercially important alkyl azo compound is azobisisobutyronitrile (AIBN), which is widely used as an initiator in free-radical polymerizations and other radical-induced reactions. It achieves this initiation by decomposition, eliminating a molecule of nitrogen gas to form two 2-cyanoprop-2-yl radicals: For instance a mixture of styrene and maleic anhydride in toluene will react if heated, forming the copolymer upon addition of AIBN. A simple dialkyl diazo compound is diethyldiazene, EtN=NEt. Because of their instability, aliphatic azo compounds pose the risk of explosion. AIBN is produced by converting acetone cyanohydrin to the hydrazine derivative followed by oxidation:Jean-Pierre Schirmann, Paul Bourdauducq: "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. . 2 (CH3)2C(CN)OH + N2H4 → (CH3)2C(CN)2N2H2 + 2 H2O (CH3)2C(CN)2N2H2 + Cl2 → (CH3)2C(CN)2N2 + 2 HCl

Safety and regulation

Many azo pigments are non-toxic, although some, such as dinitroaniline orange, ortho-nitroaniline orange, or pigment orange 1, 2, and 5 have been found to be mutagenic. Likewise, several case studies have linked azo pigments with basal cell carcinoma.

European regulation

Certain azo dyes can break down under reductive conditions to release any of a group of defined aromatic amines. Consumer goods which contain listed aromatic amines originating from azo dyes were prohibited from manufacture and sale in European Union countries in September 2003. As only a small number of dyes contained an equally small number of amines, relatively few products were affected. European Ban on Certain Azo Dyes , Dr. A. Püntener and Dr. C. Page, Quality and Environment, TFL

See also

References

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This article based upon the http://en.wikipedia.org/wiki/Azo_compound, the free encyclopaedia Wikipedia and is licensed under the GNU Free Documentation License.
Further informations available on the list of authors and history: http://en.wikipedia.org/w/index.php?title=Azo_compound&action=history
presented by: Ingo Malchow, Mirower Bogen 22, 17235 Neustrelitz, Germany