Patent GB-610710-A (GB)
Title: Recovery of monoesters of polyhydric alcohols with fatty acids and of volatile nonsaponifiable matter from fatty oils and waxes
IPC: C11C3/04
Filed: 1945-02-27
Abstract: Monoesters of polyhydric alcohols with fatty acids are recovered from crude mixtures wherein they are contained by co-distilling them with the vapour of a polyhydric alcohol, this vapour being maintained continuously present throughout the distillation either by adding the polyhydric alcohol to the crude mixture being distilled and so producing its vapour in situ or else by passing the vapour of the polyhydric alcohol through the crude mixture with the addition of any heat necessary to maintain distillation, said alcohol being volatile and heat stable under the conditions employed and showing only limited miscibility with the desired product, the co-distilled vapours being condensed and allowed to separate into two layers, the upper of which contains the desired mono-esters.  The crude mixture treated may be an incompletely alcoholysed reaction mixture derived from a fatty oil or wax and a polyhydric alcohol, the products recovered being a mixture of polyhydric alcohol mono-esters of fatty acids and the volatile non-saponifiable matter present in the oil or wax such as the fatty alcohols in the wax esters, ethers such as batyl and selachyl alcohols, hydrocarbons such as squalene, vitamins such as vitamin A from fish liver oils and tocopherols from vegetable oils.  An alcoholysis catalyst is added to the crude mixture to increase the yield of recovered product.  The distillation may be carried out under vacuum and/or with the aid of an inert carrier gas, whilst the polyhydric alcohol condensate may be recycled.  In examples: (1) sperm oil, glycerine and sodium oleate are refluxed together under vacuum and the condensate collected and allowed to separate into two layers, the lower layer of glycerine being returned to the distillation flask and the upper layer containing fatty alcohols and some mono-glycerides removed; in like manner (2) a mixture of palm kernel oil mono-glycerides, obtained by reacting palm kernel oil and glycerine in the presence of sodium glyceroxide, is refluxed with glycerine and a product comprising pure monoglycerides recovered in the upper layer of the condensate; (3) cod liver oil, glycerine containing some sodium in solution and sodium oleate are refluxed together yielding a mixture of monoglycerides and vitamin A alcohol in the product layer; (4) sperm oil and triethanolamine containing some sodium in solution are refluxed together and fatty alcohols are recovered. Other polyhydric alcohols which may be used are ethylene glycol and polyethylene glycol; propylene glycol is less satisfactory.ALSO:Monoesters of polyhydric alcohols with fatty acids are recovered from crude mixtures wherein they are contained by co-distilling them with the vapour of a polyhydric alcohol, this vapour being maintained continuously present throughout the distillation either by adding the polyhydric alcohol to the crude mixture being distilled and so producing its vapour in situ or else by passing the vapour of the polyhydric alcohol through the crude mixture with the addition of any heat necessary to maintain distillation, said alcohol being volatile and heatstable under the conditions employed and showing only limited miscibility with the desired product, the co-distilled vapours being condensed and allowed to separate into two layers, the upper of which contains the desired mono-esters.  The crude mixture treated may be an incompletely alcoholysed reaction mixture derived from a fatty oil or wax and a polyhydric alcohol, the products recovered being a mixture of polyhydric alcohol fatty acid monoesters and the volatile non-saponifiable matter present in the oil or wax such as the fatty alcohols in wax esters, ethers such as batyl and selachyl alcohols, hydrocarbons such as squalene, vitamins such as vitamin A from fish liver oils and tocopherols from vegetable oils.  An alcoholysis catalyst is added to the crude mixture to increase the yield of recovered product.  The distillation may be carried out under vacuum and/or with the aid of an inert carrier gas, whilst the polyhydric alcohol distillate may be recycled. In examples: (1) sperm oil, glycerine and sodium oleate are refluxed together under vacuum and the condensate allowed to separate into two layers, the lower glycerine layer being returned to the distillation flask and the upper layer containing fatty alcohols and some monoglycerides removed; in like manner, (2) a mixture of palm kernel oil monoglycerides, obtained as described in Specification 421,063 from palm kernel oil and glycerine in the presence of sodium glyceroxide is refluxed with glycerine and a product comprising pure palm kernel oil monoglycerides recovered; (3) cod liver oil, glycerine containing some sodium in solution, and sodium oleate are refluxed together yielding a mixture of monoglycerides and volatile non-saponifiable matter including vitamin A alcohol in the product layer; in place of sodium oleate, fatty acid monoglycerides may be added to promote miscibility of the reagents and antioxidants may be added to protect the vitamin; (4) sperm oil and triethanolamine containing some sodium in solution are refluxed together and fatty alcohols are recovered. Other polyhydric alcohols which may be used are ethylene glycol and polyethylene glycols and, less satisfactorily, propylene glycol.