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Encyclopedia Britannica



NAPHTHOLS, or HYDROXYNAPHTHALENES, C10H70H

This article appears in Volume V19, Page 168 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: NAN-NEW
NAPHTHOLS, or HYDROXYNAPHTHALENES, C10H70H , the naphthalene homologues of the phenols. The hydroxyl group is more reactive than in the phenols, the naphthols being converted into naphthylamines by the action of ammonia, and forming
ethers
  and esters much more readily.
a-Naphthol may be prepared by fusing sodium-a-naphthalene sulphonate with
caustic
  soda; by
heating
  a-naphthylamine sulphate with water to 200 C. (
English
  Patent 14301 (1892)); and by
heating
  phenyl isocrotonic acid (R. Fittig and H. Erdmann, Ann. 1885, 227, p. 242): C6H6CH:CHCH2CO2H = C1oH70H+H20. It forms colourless needles which melt at 94 C.; and is readily soluble in alcohol, ether, chloroform, and
caustic
  alkalis. It is volatile in steam. With ferric chloride it gives a dark-blue precipitate of a-dinaphthol, HOC10HsCIOHsOH. Alkaline potassium permanganate oxidizes it to phenyl-glyoxyl-ortho-carboxylic acid, H02CCsH4CO CO2H. It is reduced by sodium in boiling amyl alcohol solution to " aromatic " tetrahydro-a-naphthol (reduction occurring in the ring which does not contain the hydroxyl group). When heated with hydrazine hydrate at 16o C. it gives a-naphthyl hydrazine, CIOH7NHNH2 (L.
Hoffmann
 , Ber., 1898, 31, P. 2909). Nitric acid converts it into nitro-compounds, which are occasion-ally used for dyeing
silk
  and wool.
Martius
  yellow, C1oH6(NO2)2ONaH20, the sodium salt of 2.4 dinitro-a-naphthol (for notation see NAPHTHALENE), is prepared by the action of nitric acid on a-naphthol-2.4-disulphonic acid. It forms orange-yellow plates and dyes wool a golden yellow (from an acid bath). Naphthol yellow S., C1oH4(ONa)(NO2)2SO3Na, prepared by the action of nitric acid on a-naphthol-2.4.7-trisulphonic acid, is an orange-yellow powder which dyes wool and
silk
  yellow (from an acid bath).
Numerous mono-, di- and trisulphonic acids of a-naphthol are employed in the preparation of azo dyes. The most important is Nevile and Winther's acid, C10H6(OH)(SO3H)(1.4), formed when diazotized naphthionic acid (a-naphthylamine-4-sulphonic acid) is boiled with dilute sulphuric acid (Nevile and Winther, Ber., 188o, 13, p. 1949), or when sodium naphthionate is heated with concentrated caustic soda solution under pressure at 240260 C. (German patent 46307 (1888)). It melts at 17o C., and is readily soluble in water. With ferric chloride it gives a blue coloration.
(3-Naphthol, C10H2OH, prepared by fusing sodium (3-naphthalene sulphonate with caustic soda, crystallizes in plates which melt at 122 C. With ferric chloride it gives a green colouration, and after a time a white flocculent precipitate of a dinaphthol. With sodium in boiling amyl alcohol solution it gives a mixture of alicyclic and aromatic tetrahydro-(3-naphthols (E. Bamberger, Ber., 1890, 23, p. 197). When heated with ammonium formate to 15o C. it forms /3-naphthylamine. With nitrosodimethylaniline hydrochloride it forms Meldola's Blue (dimethylaminonaphthophenoxazonium chloride), C18H15N20C1 (R. Meldola, Ber., 1879, 12, p. 2065).
The $-naphthol sulphonic acids find extensive application in the colour industry. The most important members are shown in the table:
or naphthoquinone-
oximes
 , C1oH6(OH)(NO) or C1oHs(: NOH) : O. Two are known, namely 4-nitroso-a-naphthol or
s


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