An improved process for the synthesis of unsaturated alcohols

Details An improved process for the synthesis of unsaturated alcohols An improved process for the synthesis of unsaturated alcohols

C - Chemistry, Metallurgy

07

C

C07C 29/32 (2006.01) C07C 29/44 (2006.01) C07C 33/025 (2006.01) C07C 33/035 (2006.01)

Patent

CA 2541263

A process of preparing an unsaturated alcohol (olefin alcohol), such as, a homo-allylic mono-alcohol or homo-allylic polyol, involving protecting a hydroxy-substituted unsaturated fatty acid or fatty acid ester, such as methyl ricinoleate, derived from a seed oil, to form a hydroxy-protected unsaturated fatty acid or fatty acid ester; homo-metathesizing or cross-metathesizing the hydroxy-protected unsaturated fatty acid or fatty acid ester to produce a product mixture containing a hydroxy-protected unsaturated metathesis product; and deprotecting the hydroxy-protected unsaturated metathesis product under conditions sufficient to prepare the unsaturated alcohol. Preferably, methyl ricinoleate is converted by cross-metathesis or homo-metathesis into the homo- allylic mono-alcohol 1-decene-4-ol or the homo-allylic polyol 9-octadecene- 7,12-diol, respectively.

L'invention concerne un procédé de préparation d'un alcool insaturé (alcool oléfinique), de type mono-alcool homo-allylique ou polyol homo-allylique, qui consiste à protéger un acide gras ou un ester d'acide gras insaturé substitué par hydroxy, de type ricinoléate de méthyle, dérivé d'une huile de graine, afin que soit formé un acide gras ou un ester d'acide gras insaturé protégé par hydroxy ; à traiter par homo-métathèse ou par métathèse croisée l'acide gras ou l'ester d'acide gras insaturé protégé par hydroxy afin d'obtenir un mélange de produits contenant un produit de métathèse insaturé protégé par hydroxy ; et à annuler la protection du produit de métathèse insaturé protégé par hydroxy dans des conditions suffisantes pour préparer l'alcool insaturé. De préférence, le ricinoléate de méthyle est converti par métathèse croisée ou homo-métathèse en mono-alcool homo-allylique 1-décène-4-ol ou en polyol homo-allylique 9-octadécène-7,12-diol, respectivement.

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