Chemistry:Pigment Yellow 13
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3D model (JSmol)
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| Properties | |
| C36H34Cl2N6O4 | |
| Molar mass | 685.61 g·mol−1 |
| Appearance | yellow solid |
| Density | 1.35 g/cm3[1] |
| Hazards | |
| H413 | |
| P273, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Pigment Yellow 13 is an organic compound and an azo compound. It is a widely used yellow pigment. It is also classified as a diarylide pigment, being derived from 3,3'-dichlorobenzidine.
Production and characterization
Pigment Yellow 13 is produced industrially by tetrazotization of 3,3′-dichlorobenzidine, followed by azo coupling with acetoacetylated Xylidine.[2]
Properties
Pigment Yellow 13 is a combustible, low-flammability yellow solid that is practically insoluble in water. It decomposes upon heating above 330 °C.[3] The crystal structure consists of a layered arrangement with space group P-1 (space group no. 2).[2]
Pigment Yellow 13 is closely related to Pigment Yellow 12, wherein the two xylyl groups are replaced by phenyl and to Pigment Yellow 14 where the xylyl groups are replaced by o-tolyl.[4] It is often depicted as an azo (-N=N-) structure, but according to X-ray crystallography closely related compounds exist as the keto-hydrazide tautomers.[1]
Use
Pigment Yellow 13 is used as a pigment, primarily in offset printing.[5][6]
References
- ↑ 1.0 1.1 Barrow, M. (2002). "The crystal and molecular structures of three diarylide yellow pigments, C. I. Pigments Yellow 13, 14 and 63". Dyes and Pigments 55 (2–3): 79–89. doi:10.1016/S0143-7208(02)00068-2.
- ↑ 2.0 2.1 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.
- ↑ Record of Pigment Yellow 13 in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ↑ K. Hunger; W. Herbst (2012). "Pigments, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a20_371. ISBN 978-3-527-30673-2.
- ↑ Werner Baumann, Thomas Rothardt (2013), Druckerei-chemikalien Daten und Fakten zum Umweltschutz 2., erweiterte und überarbeitete Auflage, Springer-Verlag, pp. 186, ISBN 978-3-642-58474-9, https://books.google.com/books?id=Ps8jBgAAQBAJ&pg=PA186
- ↑ Werner Baumann, Monika Ismeier (2013), Kautschuk und Gummi Daten und Fakten zum Umweltschutz, Springer-Verlag, pp. 1628, ISBN 978-3-642-58916-4, https://books.google.com/books?id=zReaBwAAQBAJ&pg=PA1628
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