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FURFURANE (3r FURANE, C4H40, a colour...

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Originally appearing in Volume V11, Page 357 of the 1911 Encyclopedia Britannica.
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FURFURANE (3r FURANE, C4H40, a colourless liquid boiling at 32° C., found in the See also:distillation products of See also:pine See also:wood. It was first synthetically prepared by H. Limpricht (See also:Ann., 1873, 165, p. 281)  by distilling See also:barium mucate with soda See also:lime, pyromucic See also:acid C4H3O•See also:CO2H being formed, which, on further loss of See also:carbon dioxide, yielded See also:furfurane . A . Henniger (See also:Ann. chim. phys., 1886 [2], 7, p . 220), by distilling erthyrite with formic acid, obtained a dihydrofurfurane C4H6(OH)4+2H2CO2= C4H60+CO+See also:CO2+4H2O, which, on treatment with See also:phosphorus pentachloride, yielded furfurane . Furfurane is insoluble in See also:water and possesses a characteristic See also:smell . It does not react with See also:sodium or with phenylhydrazine, but yields dye-stuffs with See also:isatin and phenan- threnequinone . It reacts violently with hydrochloric acid, producing a See also:brown amorphous substance . Methyl and phenyl derivatives have been prepared by C . Paal (Ber., 1884, 17, p . 915) . Paal prepared acetonyl See also:acetophenone by condensing sodium acetoacetate with phenacylbromide, and this substance on dehydration yields aa'-phenylmethylfurfurane, the acetonyl acetophenone probably reacting in the tautomeric " enolic "See also:form, See also:CH3•CO•CHNa•COOR-I-See also:C6H6•CO•CH2Br = CH3•CO•CH(CH20006H6)•COOR . This ester readily hydrolyses, and the acid formed yields acetonyl acetophenone (by loss of carbon dioxide), which then on de-hydration yields the furfurane derivative, thus CH—CH CH—CH CH3•C<OH HO>C.C6H1=See also:H2O-f-CH3•C< O>C.C6HE .

L . Knorr (Ber., 1889, 22, p . 158) obtained diacetosuccinic ester by condensing sodium acetoacetate with See also:

iodine, and by de-hydrating the ester he prepared aa'-dimethylfurfurane f3,6'-dicarboxylic acid (carbopyrotritaric acid), which on See also:distillation yields aa'-dimethylfurfurane as a liquid boiling at 94° C . Paal also obtained this See also:compound by using monochloracetone in the See also:place of phenacylbromide . By the distillation of mucic acid or isosaccharic acid, furfurane-a-carboxylic acid (pyromucic acid), C4H3O•CO2H, is obtained; it crystallizes in needles or leaflets, and melts at 134° C . Furfurol (furol), C4H3O •CHO, is the aldehyde of pyromucic acid, and is formed on distilling See also:bran, See also:sugar, See also:wood and most carbohydrates with dilute sulphuric acid, or by distilling the pentoses with hydrochloric acid . It is a colourless liquid which boils at 162° C., and is moderately soluble in water; it turns brown on exposure to See also:air and has a characteristic aromatic smell . It shows all the usual properties of an aldehyde, forming a bisulphite compound, an oxime and a See also:hydrazone; whilst it can be reduced to the corresponding furfuryl See also:alcohol by means of sodium See also:amalgam, and oxidized to pyromucic acid by means of See also:silver See also:oxide .

End of Article: FURFURANE (3r FURANE, C4H40, a colourless liquid boiling at 32° C., found in the distillation products of pine wood. It was first synthetically prepared by H. Limpricht (Ann., 1873, 165, p. 281)
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