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C NAPHTHALENE

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Originally appearing in Volume V19, Page 168 of the 1911 Encyclopedia Britannica.
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NAPHTHALENE  ,oH8, a See also:hydrocarbon discovered in the " carbolic " and " heavy oil " fractions of the See also:coal-See also:tar distillate (see COAL-TAR) in 1819 by A . See also:Garden . It is a product of the See also:action of See also:heat on many organic compounds, being formed when the vapours of See also:ether, camphor, acetic See also:acid, See also:ethylene, See also:acetylene,, &c., are passed through a red-hot See also:tube (M . See also:Berthelot, Jahresb., 1851), or when See also:petroleum is led through a red-hot tube packed with See also:charcoal (A . Letny, Ber., 1878, II, p . 1210) . It may be synthesized by passing the vapour of phenyl butylene bromide over heated soda See also:lime (B . Aronheim, See also:Ann., 1874, 171, p . 219); and by the action of ortho-xylylene bromide on See also:sodium ethane tetracarboxylic ester, the resulting tetra-hydronaphthalene tetracarboxylic ester being hydrolysed and heated, when it yields hydronaphthalene dicarboxylic acid, the See also:silver See also:salt of which decomposes on See also:distillation into See also:naphthalene and other products (A. v . See also:Baeyer and W . H . See also:Perkin, junr., Ber., 1884, 17, P .

451): See also:

C6H4<CH2Br+Na•C(CO2R)2 C6Ha ~•CHCH2•C2•C(CO(CO22RH)2 )2 CioH8 C6H9`CHCH22•CH H•C0CO22HH C6H4`See also:CH2•C(See also:CO2H)2 " Nape," the back of the See also:neck, is of doubtful origin; it may be a variant of " knap," a knob or protuberance . It is a colourless solid, which melts at 8o° C., and boils at 218° C . It crystallizes in the See also:monoclinic See also:system; it is to be noted that a- and /3-naphthol assume almost identical forms, so that these three compounds have been called isomorphous . It is insoluble in See also:water, but is readily soluble in See also:alcohol, and ether . It has a characteristic See also:smell, and is very volatile, distilling readily in a current of See also:steam . It acts as a weak antiseptic . It is used for enriching coal See also:gas, as a See also:vermin killer, in the manufacture of certain See also:azo dyes, and in the preparation of See also:phthalic acid (q.v.) . When passed through a red-hot tube packed with See also:carbon it yields f3/3-dinaphthyl, (C10H7)2 . It forms a crystalline See also:compound with picric acid . It readily forms addition products with See also:chlorine and with See also:hydrogen; the dichloride, CIOH8C12, is obtained as a yellow liquid by acting with hydrochloric acid and See also:potassium chlorate; the solid tetrachloride, Clo Ha C14, results when chlorine is passed into naphthalene dissolved in See also:chloroform . Numerous hydrides are known; heated with red See also:phosphorus and hydriodic acid the hydrocarbon yields mixtures of hydrides of See also:composition Clotho to C1oH2o . Sodium in boiling See also:ethyl alcohol gives the a-dihydride, CloHlo (E .

See also:

Bamberger, Ber., 1887, 20, p . 1705); and with boiling amyl alcohol the (3-tetrahydride, CIOH12 (E . Bamberger, Ber., 189o, 23, p . 1561) . The a-tetrahydronaphthalene is formed when naphthalene is heated with phosphonium iodide at 170°-190° (A. v . Baeyer) .

End of Article: C NAPHTHALENE
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