Chemistry:Acid Red 29

From HandWiki
Acid Red 29
Names
Other names
  • Chromotrope 2R
  • Disodium 4,5-dihydroxy-3-phenylazonaphthalene-2,7-disulphonate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 224-085-0
Properties
C16H10N2Na2O8S2
Molar mass 468.36 g·mol−1
Hazards
GHS pictograms GHS07: Harmful
GHS Signal word Warning
H315, H319, H335
PP261Script error: No such module "Preview warning".Category:GHS errors, PP264Script error: No such module "Preview warning".Category:GHS errors, PP264+P265Script error: No such module "Preview warning".Category:GHS errors, PP271Script error: No such module "Preview warning".Category:GHS errors, PP280Script error: No such module "Preview warning".Category:GHS errors, PP302+P352Script error: No such module "Preview warning".Category:GHS errors, PP304+P340Script error: No such module "Preview warning".Category:GHS errors, PP305+P351+P338Script error: No such module "Preview warning".Category:GHS errors, PP319Script error: No such module "Preview warning".Category:GHS errors, PP321Script error: No such module "Preview warning".Category:GHS errors, PP332+P317Script error: No such module "Preview warning".Category:GHS errors, PP337+P317Script error: No such module "Preview warning".Category:GHS errors, PP362+P364Script error: No such module "Preview warning".Category:GHS errors, PP403+P233Script error: No such module "Preview warning".Category:GHS errors, PP405Script error: No such module "Preview warning".Category:GHS errors, PP501Script error: No such module "Preview warning".Category:GHS errors
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Color Index Acid Red 29 is a chemical compound belonging to the class of azo dyes and the application group of acid dyes. It is the simplest chromotropic dye and was originally used to dye wool.[2]

Synthesis

Acid Red 29 is synthesized via the diazotization of aniline using sodium nitrite and hydrochloric acid, followed by the azo coupling of the resulting diazonium salt with chromotropic acid.[2][3]

Use

Acid Red 29 is used to dye wool a bluish-red hue.[4] Treatment with chromium salts, such as potassium dichromate, produces a distinct color change from red to violet.[5]

Acid Red 29 is used in histological staining—such as the Gömöri trichrome stain—in combination with aniline blue and hematoxylin.[6]

Acid Red 29 is used in the complexometric titration of thorium.[7]

History

The production of this dye was patented by Hoechst in 1890.

As with other chromotropic acid-based dyes, the patent literature describes its primary application as wool printing.[3]

References

  1. ↑ PubChem. "Disodium 4,5-dihydroxy-3-phenylazonaphthalene-2,7-disulphonate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/20172. 
  2. ↑ 2.0 2.1 Gustav Schultz, Paul Julius (1897), Tabellarische Übersicht der im Handel befindlichen künstlichen organischen Farbstoffe (3 ed.), Berlin: B.Gaertner's Verlagsbuchhandlung, pp. 10, https://archive.org/details/b21980408/page/10/mode/2up?view=theater 
  3. ↑ 3.0 3.1 "Verfahren zur Darstellung von Azofarbstoffen aus einer neuen Dioxynaphthalindisulfonsäure" DE patent 69095, published 1894-05-16
  4. ↑ P. Heermann, ed. (1930), Enzyklopädie der textilchemischen Technologie, Berlin, Heidelberg: Springer-Verlag, pp. 479, doi:10.1007/978-3-642-94236-5, https://books.google.com/books?id=mz_PBgAAQBAJ&pg=PA479 
  5. ↑ Erich Rosenhauer, Werner Wirth, Rudolf Königer (1928), "Über Chromierfarbstoffe der Azoreihe: Die Chromierfärbung von Chromotrop 2R", Sitzungsberichte der Physikalisch-Medizinischen Sozietät zu Erlangen 60: 9–14, https://www.zobodat.at/pdf/Sitzber-physik-med-Soc-Erlangen_60_0009-0014.pdf 
  6. ↑ Gudrun Lang (2006), Histotechnik, Wien, New York: Springer, pp. 199, ISBN 3-211-33141-7, https://books.google.com/books?id=FulU0tG7kaQC&pg=PA199 
  7. ↑ Edmund Bishop, ed. (1972), Indicators, Oxford: Pergamon Press, pp. 255, https://books.google.com/books?id=vnj9BAAAQBAJ&pg=PA255