Search over 40,000 articles from the original, classic Encyclopedia Britannica, 11th Edition.
|
See also:XANTHONE (dibenzo-y-pyrone, or diphenylene ketone See also:oxide) , C13HiO2, in organic See also:chemistry, a heterocyclic See also:compound containing the See also:ring See also:system shown below . It is obtained by the oxidation of xanthene (methylene diphenylene See also:oxide) with chromic See also:acid; by the See also:action of See also:phosphorus oxycliloride on disodium salicylate; by See also:heating 2.2'-dioxybenzophenone with concentrated sulphuric acid; by distilling fluoran with See also:lime; by the oxidation of xanthydrol (R . See also:Meyer, Ber., 1893, 26, p . 1277); by boiling diazotized 2.2'-diaininobenzophenone with See also:water (Heyl., Ber., 1898, 31, p . 3034) ; by heating salol with concentrated sulphuric acid (C . Graebe, See also:Ann., 1889, 254, p . 280), and by heating See also:potassium-ortho=chlorobenzoate with See also:sodium phenolate and a small quantity of See also:copper See also:powder to 180–190° C . (F . See also:Ullmann, Ber., 1905, 38, pp . 729, 2120, 2211) . It crystallizes in needles which melt at 173–174° and See also:boil at 349–350° C., and are volatile in See also:steam . Its See also:solution in concentrated sulphuric acid is of a yellow See also:colour and shows a marked See also:blue See also:fluorescence . The carbonyl See also:group is not ketonic in See also:character since it yields neither an oxime nor See also:hydrazone . When fused with See also:caustic potash it yields phenol and salicylic acid . Mild reducing agents convert it into xanthydrol, the group > CO becoming > CH•OH, whilst a strong reducing See also:agent like hydriodic acid converts it into xanthene, the group> CO becoming> See also:CH2 . Phosphorus pentasulphide at 140–150° C. converts it into xanthion by transformation of > CO to >CS (R . Meyer, Ber., 1900, 33, p . 2580), and this latter compound condenses with See also:hydroxylamine to See also:form See also:xanthone oxime . All four mono-hydroxyxanthones are known, and are prepared by heating salicylic acid with either See also:resorcin, See also:pyrocatechin or hydroquinone; they are yellow crystalline solids, which See also:act as dyestuffs . The 1.7-di,hydroxyxanthone, known as euxanthone, is prepared by heating euxanthic acid with hydrochloric acid or by heating hydrouinone carboxylic acid with l3-resorcylic acid and acetic anhydride (S . Kostanecki, Ber., 1891, 24, p . 3983E C . Graebe, Ann., 1889, 254, p . 298) . It is also obtained from See also:Indian yellow (Graebe, ibid.), formed in the urine of cows fed on See also:mango leaves . It crystallizes in yellow needles which See also:sublime readily . On See also:fusion with caustic potash it decomposes with formation of tetrahydroxy-See also:benzophenone, which then breaks up into resorcin and hydroquinone . The isomeric 1.6-dihydroxyxanthone, isoeuxanthone, is formed when 13-resorcylic acid is heated with acetic anhydride . Gentisein, or 1.3.7-trihydroxyxanthone, is found in the form of its methyl See also:ether (gentisin) in See also:gentian See also:root; it is obtained synthetically by condensing phloroglucin with hydroquinone carboxylic acid . Xanthene, C15H1oO, may be synthesized by condensing phenol with ortho-cresol in the presence of See also:aluminium chloride . Its tetramethyl-diamino derivative, which is formed by condensing formaldehyde with dimethyl-See also:meta-aminophenol and subsequent elimination of water from the resulting See also:diphenyl methane derivative, is the leuco See also:base of pyronine, into which it passes by oxidation . Cl(CHa)2N/\/\ o /\% 8 7/\/CO\, /~//CH\ \/\ /\/~3 5 4 Xanthone . Pyronine . |
|
|
[back] XANTHIPPE |
[next] XANTHUS (mod. Gunuk) |
There are no comments yet for this article.
Do not copy, download, transfer, or otherwise replicate the site content in whole or in part.
Links to articles and home page are encouraged.