Arylide yellow

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Arylide yellowHow to read this color infobox
About these coordinates     Color coordinates
Hex triplet #E9D66B
sRGBB  (rgb) (233, 214, 107)
CMYKH   (c, m, y, k) (0, 8, 54, 9)
HSV       (h, s, v) (51°, 54%, 91%)
Source [1] [2]
B: Normalized to [0–255] (byte)
H: Normalized to [0–100] (hundred)

Arylide yellow, also known as Hansa Yellow and Monoazo yellow, are a family of organic compounds used as pigments. They are primarily in artistic oil paints and watercolors. These pigments are usually semi-transparent yellows and yellow-greens. Related organic pigments are the diarylide pigments. Overall, these pigments have partially displaced cadmium yellow in the marketplace.

Production[edit]

The compound is obtained by azo coupling of aniline and acetoacetanilide or their derivatives. The class of compounds was discovered in Germany in 1909.[1]

Synthesis of Hansa Yellow Pigments, R and R' represent a variety of substituents.

Examples[edit]

Members of this class include:

  • Pigment Yellow 6 (CAS # 2512-29-0), derived from 4-chloro-2-nitroaniline (diazonium precursor) and aniline (acetoacetanilide precursor) to produce medium yellows.
  • Pigment Yellow 3 (CAS # 6486-23-3), derived from 4-chloro-2-nitroaniline (diazonium precursor) and 2-chloroaniline (acetoacetanilide precursor) to produce greenish-yellows.
  • Pigment Yellow 16 derived from 2,4-dichloroaniline (diazonium precursor) and o-tolidine (acetoacetanilide precursor) to produce medium-yellows.
  • Pigment Yellow 74 (CAS # 6358-31-2), derived from 2-methoxy-4-nitroaniline (diazonium precursor) and 2-methoxyaniline (acetoacetanilide precursor) to produce greenish-yellows.

Pigment Yellow 16

Maimeri, an Italian paint manufacturer, combines arylide yellow with yellow iron oxide and zinc oxide to create their version of Naples yellow light.

See also[edit]

References[edit]

  1. ^ K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a20_371