Dibromoanthanthrone

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Structural formula
Structural formula of dibromoanthanthrone (Vat Orange 3, Pigment Red 168)
General
Surname Dibromoanthanthrone
other names
  • 4,10-dibromonaphtho [7,8,1,2,3- nopqr ] tetraphen-6,12-dione ( IUPAC )
  • 4,10-dibromoanthanthrone
  • 4,10-dibromo-dibenzo [ def , mno ] chrysen-6,12-dione
  • CI Vat Red 3
  • CI Pigment Red 168
  • CI 59300
Molecular formula C 22 H 8 Br 2 O 2
External identifiers / databases
CAS number 4378-61-4
EC number 224-481-3
ECHA InfoCard 100.022.257
PubChem 78084
ChemSpider 70462
Wikidata Q25939343
properties
Molar mass 464.12 g mol −1
Physical state

firmly

Melting point

400 ° C

solubility
  • Easily soluble in some organic solvents
  • practically insoluble in water (<= 10.8 µg / l at 24 ° C)
safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dibromoanthanthrone is an orange-red, synthetic, organic colorant . It is structurally derived from the anthanthrone or anthanthrone .

It was only produced in 1913 as a vat dye ( CI Vat Orange 3, CI 59300) and later also used as a pigment (CI Pigment Red 168).

Extraction and presentation

To produce dibromoanthanthrone, 1-aminonaphthalene is reacted with phosgene and aluminum chloride to give naphthostyril , which can be saponified to give 1-aminonaphthalene-8-carboxylic acid . The dimerization to 1,1'-dinaphthyl-8,8'-dicarboxylic acid takes place by diazotization and subsequent boiling in the presence of copper powder . Without intermediate isolation, 4,10-dibromoanthanthrone is obtained from this with sulfuric acid and subsequent bromination .

use

Dibromoanthanthrone is one of the most lightfast and weatherproof organic pigments. It is used in high-quality paints for pure scarlet tones and in very low concentrations for nuance, in mixed systems and in high-quality architectural colors for pastel tones. The pigment is of secondary importance for printing inks; it is only used in special printing inks for poster printing and sheet metal printing. Its more yellowish 4,10-dichloro derivative is irrelevant as a pigment.

Individual evidence

  1. ↑ a b c data sheet VAT ORANGE 3 (CI 59300) from Sigma-Aldrich , accessed on July 21, 2016 ( PDF ).
  2. ↑ a b Werner Baumann, Thomas Rothardt: Printing chemicals: data and facts on environmental protection 2nd, expanded and revised edition . Springer-Verlag, 1999, ISBN 978-3-642-58474-9 , pp. 1277 ( limited preview in Google Book search).
  3. ↑ Registration dossier on 4,10-dibromodibenzo [def, mno] chrysene-6,12-dione (section Water solubility ) at the European Chemicals Agency (ECHA), accessed on July 21, 2017.
  4. ↑ Willy Herbst, Klaus Hunger: Industrial organic pigments: production, properties, application ; VCH 1995, ISBN 978-3-527-62496-6 , p. 527 ( limited preview in the Google book search).
  5. ↑ Nicholas Eastaugh et al. (2004) The Pigment Compendium: A Dictionary of Historical Pigments , ISBN 978-0-7506-5749-5 , p. 301 ( limited preview in the Google book search).
  6. ^ Lynn A. Bente: Dyes for the mass coloration of plastics In: Geoffrey Pritchard: Plastics Additives: An AZ reference . Springer – Science + Business Media, 1998. ISBN 978-94-011-5862-6 , p. 223 ( limited preview in Google book search).
  7. ↑ a b Entry on anthanthrone pigments. In: Römpp Online . Georg Thieme Verlag, accessed on July 21, 2016.