Volume 1

Chemical technology and analysis of oils, fats, and waxes / by J. Lewkowitsch.

  • Julius Lewkowitsch
Date:
1904
Catalogue details

Licence: Attribution-NonCommercial 4.0 International (CC BY-NC 4.0)

Credit: Chemical technology and analysis of oils, fats, and waxes / by J. Lewkowitsch. Source: Wellcome Collection.

    34/454 (page 14)
    Triricinolein, Ricinolein, C3H6(0. C18H8302)8, has been synthesised by heating glycerol with an excess of ricinoleic' acid to 230° C. for six hours, unchanged glycerol and ricinoleic acid being re- moved by water and petroleum ether respectively.1 If, as in Berthelot’s method, pressure and high temperature be employed, condensation products of mono- and diricinolein are formed, the simplest of which is isomeric with triricinolein, and has the formula OH . c17h32 . COO. C}7H32. COO. C3H.(C17H32. COOH),. When triricinolein is heated in a solution of toluene, with or without zinc chloride, it is condensed to several esters, such as that represented by the formula (OH . C17H32. COO)2(C3H5 . C77H32. C0)20, which differ from triricinolein by their sparing solubility in alcohol and petroleum ether. H. Meyer2 describes triricinolein (prepared by heating ricinoleic acid and glycerol in a current of carbonic dioxide to 280°-300° C.) as a colourless oil soluble in 96 per cent alcohol, and in methyl alcohol, miscible with absolute alcohol and glacial acetic acid, sparingly soluble in petroleum ether. It has the specific gravity 0'959-0-984. It is optically active; [a]n = + 5T6°. Unlike castor oil, it does not form ricinelaidin on treating with nitrous acid. On keeping, it is stated by Meyer to undergo polymerisation, the molecule becoming doubled or trebled, as indicated by the increase of the specific gravity to 0-988-l‘009, and the decrease of the iodine number 71’84 to 44-7 (cp. however, “ Castor Oil,” chap. xiv.). Mixed Triglycerides The mixed triglycerides prepared synthetically were obtained by similar methods to those employed in the preparation of simple triglycerides. However, when oleic acid is allowed to act on dis- tearin or dipalmitin in the manner described for the synthesis of glycerides, very considerable quantities of tristearin and tripalmitin are formed, whilst the yield of oleodistearin and oleodipalmitin is small. Evidently a molecular rearrangement takes place, so that in the attempt to synthesise the mixed glycerides, such as oleodistearin,3 a considerable yield of tristearin and smaller quantities of oleo- distearin are obtained. Acetodiformin, C3H5(0 . C2H30)(0 . COH)2, has been obtained by the action of the mixed anhydride of formic and acetic acids, CHo . CO . 0 . CHO,4 on glycerol. It is miscible with alcohol and ether in every proportion. d° = U249. It boils, under a pressure of 27 mm., at 157 C. /3-Acetodibutyrin, C3Hf)(0 . C4H70)(0. C2H30)(0. C4H70), is ob- tained by the interaction of acetodichlorhydrin and sodium butyrate, or by the action of a-dibutyrin on acetyl chloride. 1 Juillard, Journ. Chem. Soc. 1895, Abstracts, i. 500. 2 Journ. Soc. Chem. Jnd. 1897, 633, 684. 3 Kreis and Hafner, Berickte, 1903, 2766. 4 Bihal, Compt. rend. 128, 1460.