Synthetic Tannins by Georg Grasser
page 17 of 193 (08%)
page 17 of 193 (08%)
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HO OH ______OH HO{_____}--------CO--------{______}OH COOH OH [Diagonal bond between HO and COOH on left.] The ketone formula was corroborated by Nierenstein, [Footnote: _Ber._ 1905, 38, 3641.] who distilled tannin with zinc dust and obtained diphenylmethane (smell of benzene) and a crystalline product, M.P. 7O -71 C. (M.P. of diphenyl = 71 C.). Konig and Kostanecki [Footnote: _Ibid._, 1906, 39, 4027.] sought to find the constitution of the tannins in the leuco-compounds of the oxyketones, to which catechin belongs. Nierenstein (see above), however, emphasises that the high molecular weight and the optical activity speak against the digallic acid formula, but in favour of this are the following points: (1) the decomposition of tannin with the formation of gallic acid; (2) the decomposition of methylotannin with the formation of di- and trimethyl esters of gallic acid; and (3) the production of diphenylmethane on distillation with zinc dust. The latter reaction especially illustrates the analogous formation of fluorene from compounds of the type-- --CO.O ^ ______ ^ | | | | | | | | V V Nierenstein gave the name "Tannophor" to the mother-substance of tannin, phenylbenzoate, C_6H_5-COO-C_6H_5. |
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