Naphthoquinone series — Part I

Brazanquinone vat dyes from 2∶3-dichloro-1∶4-naphthoquinone: Part I constitution of “iso-dinaphthalene oxide”
  • B. Suryanarayana
  • B. D. Tilak


Brazanquinone vat dyes have been prepared by the condensation of 2∶3-dichloro-1∶4-naphthoquinone (I) with α- and β-naphthols and their bromo derivatives and by the condensation with Naphtol AS. Reaction of 1-bromo-2-naphthol with (I) in pyridine gave a halogenonaphthoquinone together with a halogen-free naphthoquinone which proved to be identical with the reaction product (A) obtained from (I) and β-naphthol in pyridine. The 1-position in β-naphthol is thus involved in the condensation with (I) and (A) is therefore constituted as the furan derivative, 1∶2-benzobrazanquinone (V). Constitution of “iso-dinaphthalene oxide” as dinaphtho-(2′∶3′∶2∶3-) (1″∶2″∶4∶5) furan (VI) (follows from its conversion to (V) by oxidation and conversely by its synthesis from (V) by zinc dust distillation. The condensation product of (I) with Naphtol AS is likewise the furan derivative 1∶2-brazanquinone-4-carboxyanilide (VIII) since it is also formed from 1-bromo-2-hydroxy-3-naphthanilide by loss of bromine.

Introduction of bromine in (V) and 3∶4-benzobrazanquinone and the introduction of the carboxyanilide group in (V) leads to more substantive dyes. The dyes give yellow and orange yellow shades. Fastness properties of the dyes have been determined.


Betaine Naphthoquinone Fastness Property Sodium Ethoxide Furan Derivative 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Terhost and FlixInd. Eng. Chem., 1943,35, 1255.CrossRefGoogle Scholar
  2. 2.
    Ullmann and EttischBer., 1921,54 B, 259.Google Scholar
  3. 3.
    GhoshJ.C.S., 1915, 1595.Google Scholar
  4. 4.
    KostaneckiBer., 1903,36, 2193.Google Scholar
  5. 5.
    Graebe and LiebermannIbid.,, 1899,32, 924.Google Scholar
  6. 6.
    EistertIbid.,, 1947,80, 47.CrossRefGoogle Scholar
  7. 7.
    BIOS, 987, 125;FIAT.,1313, III, 35.Google Scholar
  8. 8.
    Clemo and SpenceJ.C.S., 1928, 2813.Google Scholar
  9. 9.
    Clemo and CockburnIbid. J.C.S., 1931, 1265.Google Scholar
  10. 10.
    Buu HoiIbid., J.C.S., 1952, 489.Google Scholar
  11. 11.
    Jadhav and RaoProc. Ind. Acad. Sci., 1946,23 A, 215.Google Scholar
  12. 12.
    See following and subsequent papers.Google Scholar
  13. 13.
    Fieser and BrownJ.A.C.S., 1949,71, 3609.CrossRefGoogle Scholar
  14. 14.
    — and DesreuxIbid.,, 1938,60, 2260.Google Scholar
  15. 15.
    VogelA Text-Book of Practical Organic Chemistry (Longmans), 1951, p. 905.Google Scholar
  16. 16.
    Koelsch and KushrerOrganic Synthesis, 1940,20, 18.Google Scholar
  17. 17.
    J. Soc. Dyers and Col., 1940,56, 273.Google Scholar
  18. 18.
    Fastness Assessment of Textile Dyestuffs, Imperial Chemical Industries Ltd., London, p. 47.Google Scholar

Copyright information

© Indian Academy of Sciences 1953

Authors and Affiliations

  • B. Suryanarayana
    • 1
  • B. D. Tilak
    • 1
  1. 1.Department of Chemical TechnologyUniversity of BombayBombay 19

Personalised recommendations