Patent GB-881714-A (GB)
Title: Improved margarine
IPC: A23D7/01
Filed: 1959-02-27
Abstract: Anti-spattering agents for incorporation into margarine (see Group I), consist of a mixed ester of a polyalcohol with 3 or 4 OH groups, of which one is esterified with a fatty acid of 8 to 24 carbon atoms and of which a second may be esterified with a fatty acid of 1 to 24 carbon atoms, and which further is esterified with 1 or 2 molecules of a polycarboxylic acid consisting of tricarballylic acid, aconitic acid, and acylated or non-acylated hydroxy polycarboxylic acids of which one COOH group at least is not esterified and a second may be esterified with a polyol not otherwise esterified, but excluding mixed esters with two acylated hydroxypolycarboxylic acid radicals if the latter contain four or more acyl residues per molecule of mixed ester.  The following general methods for the preparation are described: the triol or tetrol mono-ester, in the absence of or with at most a low proportion of glycerol, is heated with malic acid or citric acid in a proportion of 0.8-1.2 mols. preferably 1 mol., of the acid per mol. of mono-ester, at a temperature between 110 DEG C. and 150 DEG C. for between 10 hours and 15 minutes, and then the resulting mixture is cooled; when the polyol is glycerol, pentaerythritol or sorbitan, the reaction may be conducted at about 130 DEG C. for 1 to 2 hours under reduced pressure and/or while directing a current of inert gas through the reaction mixture.  It is stated that the antispattering property may be lost by heating over long at the reaction temperature.  According to an example, 354g commercial glycerol-mono-oleate (47% glycerol-mono-oleate) and 67g malic acid were stirred under nitrogen and heated to 130 DEG C. until the mixture had become homogenous.  A reduced pressure of 40 mm. was applied and the heating at 130 DEG C. continued for 2 hours.  To this completely dry product were added 205g of acetic acid anhydride and the mixture was heated at 120 DEG C. for one hour, after which the acetic acid and excess acetic acid anhydride were distilled off at reduced pressure.  The product, the malic acid ester of glycerol mono-oleate mono-acetate, showed a hydroxyl value of 5.  Other examples describe the reaction between glycerol mono-oleate and citric acid, glycerol mono-stearate and diacetyltartic acid anhydride, glycerol mono-laurate and acetylcitric acid anhydride, glycerol mono-stearate and citric acid, pentaerythritol mono-stearate and citric acid, glycerol di-stearate and diacetyl tartaric acid anhydride, and glycerol mono-stearate and aconitic acid anhydride. U.S.A. Specification 2,192,907 is referred to.ALSO:The spattering of margarine is reduced or eliminated by adding to the margarine a mixed ester, or a mixture of such esters, of a polyalcohol with 3 or 4 OH groups, of which one is esterified with a fatty acid of 8 to 24 carbon atoms and of which a second may be esterified with a fatty acid of 1 to 24 carbon atoms, and which further is esterified with 1 or 2 molecules of a polycarboxylic acid consisting of tricarballylic acid, aconitic acid, and acylated or non-acylated hydroxypolycarboxylic acids of which one COOH group at least is not esterified and a second may be esterified with a polyol not otherwise esterified, but excluding mixed esters with two acylated hydroxypolycarboxylic acid radicals if the latter contain four or more acyl residues per molecule of mixed ester; one of the hydroxyl groups of the hydroxypolycarboxylic acid may be esterified with a fatty acid having 1 to 24 carbon atoms and a second hydroxyl group may be esterfied.  When only one hydroxyl group of the polyalcohol is esterified by a polycarboxylic acid, Hydroxypolycarboxylic acids specified are malic, citric, tartaric and citraconic acids.  The method of preparing certain of the esters is described (see Group IV(b)).  The ester is preferably incorporated in a proportion of about 0,01-0,3% by weight of the margarine.  Enhanced anti-spattering results from including additionally in the margarine about 30% of phosphatides, such as lecithin, based on the weight of the ester.