Chemistry:Pigment Yellow 14
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3D model (JSmol)
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| Properties | |
| C34H30Cl2N6O4 | |
| Molar mass | 657.55 g·mol−1 |
| Appearance | yellow solid |
| Density | 1.41 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 14 is an organic compound classified as an azo compound. It is a commercial yellow pigment. It is also classified as a diarylide pigment, being derived from 3,3'-dichlorobenzidine.
Production
Pigment Yellow 14 is produced industrially by tetrazotization of 3,3'-dichlorobenzidine, followed by azo coupling with acetoacetylated o-Toluidine.[2]
Properties
Pigment Yellow 14 is a sparingly flammable, yellow, odorless solid that is practically insoluble in water. It decomposes when heated above 308 °C.[3] It has a crystal structure with the space group P1.[2]
Pigment Yellow 14 is closely related to Pigment Yellow 13, wherein the two xylyl groups are replaced by an ortho 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 14 is used as a pigment (for example in packaging and textile printing).[5]
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 14 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.
- ↑ Willy Herbst, Klaus Hunger (2009), Industrielle Organische Pigmente Herstellung, Eigenschaften, Anwendung, John Wiley & Sons, pp. 257, ISBN 3-527-62496-1, https://books.google.com/books?id=zP0JXdYsWP0C&pg=PA257
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