Pigment Yellow 83

Last updated
Pigment Yellow 83
PigmentYell83correctTaut.svg
Names
Other names
Enceprint Yellow 1780, Homapol Yellow PO-227
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.024.491 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 226-939-8
PubChem CID
UNII
  • InChI=1S/C36H32Cl4N6O8/c1-17(47)33(35(49)41-27-15-29(51-3)23(39)13-31(27)53-5)45-43-25-9-7-19(11-21(25)37)20-8-10-26(22(38)12-20)44-46-34(18(2)48)36(50)42-28-16-30(52-4)24(40)14-32(28)54-6/h7-16,33-34H,1-6H3,(H,41,49)(H,42,50)/b45-43+,46-44+
    Key: NKXPXRNUMARIMZ-MWOVFPFUSA-N
  • COc1cc(Cl)c(OC)cc1NC(=O)C(C(=O)C)/N=Nc2ccc(cc2Cl)-c3cc(Cl)c(cc3)/N=N/C(C(=O)C)C(=O)Nc4cc(OC)c(Cl)cc4OC
Properties
C36H32Cl4N6O8
Molar mass 818.49 g·mol−1
AppearanceYellow solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Color Index Pigment Yellow 83 is an organic compound that is classified as a diarylide pigment. It is used as a yellow colorant.

Contents

Production

The compound is produced industrially from three components: Treatment of 2,5-dimethoxy-4-chloroaniline with diketene gives an acetoacetylated aniline. This compound is then coupled to the bisdiazonium salt obtained from 3,3'-dichlorobenzidine. [1]

Properties

Pigment Yellow 83 is a slightly flammable yellow solid that is practically insoluble in water. It decomposes when heated above 300 °C. [2] It exhibits a crystal structure belonging to the space group P21/c or space group Pc. [3]

As confirmed by X-ray crystallography, the compound exists as a bis(keto-hydrazide) tautomer, not a true diazo compound. [4]

Use

Pigment Yellow 83 is used, for example, as a reddish-yellow pigment in printing inks and plastics. [5] [6]

References

  1. ↑ K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi : 10.1002/14356007.a20_371
  2. ↑ Recordof Pigment Yellow 83 in the GESTIS Substance Database of the Institute for Occupational Safety and Health Error in template * unknown parameter name (Template:GESTIS): "Abruf"
  3. ↑ Martin U. Schmidt, Robert E. Dinnebier, Holger Kalkhof: Crystal Engineering on Industrial Diaryl Pigments Using Lattice Energy Minimizations and X-ray Powder Diffraction. In: The Journal of Physical Chemistry B. 111, 2007, S. 9722, doi : 10.1021/jp071731p.
  4. ↑ Barrow, Michael J.; Christie, Robert M.; Badcock, Tracey D. (2003). "The crystal and molecular structure of C.I. Pigment Yellow 83, a superior performance Diarylide Yellow pigment". Dyes and Pigments. 57 (2): 99–106. doi:10.1016/S0143-7208(02)00117-1.
  5. ↑ Werner Baumann, Thomas Rothardt (2013), [ , p. 585, at Google Books Druckerei-chemikalien Daten und Fakten zum Umweltschutz 2., erweiterte und überarbeitete Auflage], Springer-Verlag, p. 585, ISBN   978-3-642-58474-9 {{citation}}: Check |url= value (help)
  6. ↑ Willy Herbst, Klaus Hunger (2009), [ , p. 261, at Google Books Industrielle Organische Pigmente Herstellung, Eigenschaften, Anwendung], John Wiley & Sons, p. 261, ISBN   3-527-62496-1 {{citation}}: Check |url= value (help)
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