Disodium 4,4'-dinitrostilbene-2,2'-disulfonate

Disodium 4,4'-dinitrostilbene-2,2'-disulfonate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.020.956
Properties
C14H8N2Na2O10S2
Molar mass 474.335
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Disodium 4,4′-dinitrostilbene-2,2′-disulfonate is an organic compound with the formula (O2NC6H3(SO3Na)CH)2 This salt is a common precursor to a variety of textile dyes and optical brighteners

Preparation and reactions

In the laboratory disodium 4,4′-dinitrostilbene-2,2′-disulfonate is obtained by sulfonation of 4-nitrotoluene giving the intermediate product, 4-nitrotoluene-2-sulfonic acid, with oxidation using sodium hypochlorite yielding the disodium salt of 4,4′-dinitrostilbene-2,2′-disulfonic acid.[1] The oxidative couple of the toluene intermediate to the stilbene dimer was originally developed by Arthur Green and André Wahl in the late nineteenth century.[2][3] Improvements to the process with higher yields have been developed, using air oxidation in liquid ammonia.[4] The product is useful as its reaction with aniline derivatives results in the formation of azo dyes. Commercially important dyes derived from this compound include Direct Red 76, Direct Brown 78, and Direct Orange 40.[5] Reduction gives 4,4′-diamino-2,2′-stilbenedisulfonic acid, which is a common optical brightener.

References

  1. ↑ Cumming, William M.; Hopper, I. Vance; Wheeler, T. Sherlock (1926). "Preparation 294.—Dinitro-Stilbene-Disulphonic Acid (Na salt)". Systematic Organic Chemistry: Modern Methods of Preparation and Estimation. New York: D. Van Nostrand Company. p. 314.
  2. ↑ Green, Arthur G.; Wahl, André R. (1897). "Ueber die Oxydation von Paranitrotoluolsulfosäure" [On the oxidation of para-nitrotoluenesulfonic acid]. Ber. Dtsch. Chem. Ges. (in German). 30 (3): 3097–3101. doi:10.1002/cber.189703003128.
  3. ↑ Green, Arthur G.; Wahl, André R. (1898). "Ueber die Oxydation der Paranitrotoluolsulfosäure" [On the oxidation of para-nitrotoluenesulfonic acid]. Ber. Dtsch. Chem. Ges. (in German). 31 (1): 1078–1080. doi:10.1002/cber.189803101195.
  4. ↑ US patent 5041632, Guglielmetti, Leonardo, "Process for the preparation of 4,4'-dinitrostilbene-2,2-disulfonic acid", published 1991-08-20, issued 1991-08-20, assigned to Ciba-Geigy Corporation
  5. ↑ Hunger, Klaus; Mischke, Peter; Rieper, Wolfgang; Raue, Roderich; Kunde, Klaus; Engel, Aloys (2005). "Azo Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_245.
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