Patent GB-926607-A (GB)
Title: Saturated aliphatic carboxylic ester compositions and lubricants consisting of or containing them
Inventor: CRITCHLEY STUART WALTER
IPC: C07C67/08
Filed: 1959-11-10
Abstract: Plasticizers for thermoplastic resins, e.g. polyvinyl chloride, comprise esters prepared from sturated aliphatic polyhydric alcohol with from 5 to 15 carbon atoms, and no hydrogen attached to any carbon atom in the 2-position with respect to a hydroxyl group or a mixture of such alcohols, and a mixture of aliphatic monocarboxylic acids produced by the oxidation of capryl alcohol or methyl hexyl ketone, or a mixture of these two compounds (see Group IV(b)). 1,1,1-trimethylol propane, 2-methyl-2-n-propyl-1,3-propanediol, neopentyl glycol, pentaerythritol and di- and tripentaerythritol are examples of the polyhydric alcohols, and the capryl alcohol or methyl hexyl ketone or the mixtures thereof, obtained as a by-product of the process for the preparation of sebacic acid from ricinoleic or esters thereof such as castor oil, may be oxidized to give a mixture of acids consisting predominantly of those containing 5 to 7 carbon atoms, e.g. caproic and heptanoic acids.  A composition is described comprising, polyvinyl chloride, the hexa-ester derived from dipentaerythritol, and a mixture of aliphatic mono-carboxylic acids obtained from the oxidation of commercial methyl hexyl ketone, basic lead carbonate and dioctyl phthalate which is hot-rolled and milled to sheets.ALSO:The invention comprises ester compositions prepared by completely esterifying a saturated aliphatic polyhydric alcohol with from 5 to 15 carbon atoms, and no hydrogen attached to any carbon atom in the 2-position with respect to a hydroxyl group, or a mixture of such alcohols with the mixture of aliphatic monocarboxylic acids produced by the oxidation of capryl alcohol or methyl hexyl ketone, or a mixture of these two compounds. Preferred polyhydric alcohols are those of general formula <FORM:0926607/IV(a)/1> in which R1 represents an alkyl group with 1 to 4 carbon atoms or a methylol group, R2 an alkyl group with 1 to 4 carbon atoms or a -CH2-OR3 group wherein R3 represents a hydrogen atom or a saturated aliphatic hydrocarbon group with 5 to 10 carbon atoms and containing one or more primary hydroxyl constituents, e.g. 1,1,1-trimethylol propane, 2-methyl-2-n-propyl-1,3-propanediol, neopentyl glycol, pentaerythritol, and di- and tri-pentaerythritol.  The capryl alcohol or methyl hexyl ketone, or the mixtures thereof, obtained as a by-product of the process for the preparation of sebacic acid from ricinoleic acid or esters thereof such as castor oil, may be oxidised, e.g. with nitric acid in the presence of ammonium metavanadate, or with sodium hypochlorite, or air or oxygen, and the resulting mixture of acids consists predominantly of those containing 5 to 7 carbon atoms in the molecule, e.g. caproic and heptanoic acids.  The esterification is performed using stoichiometric proportions, preferably in the presence of a catalyst, e.g. p-toluene sulphonic acid, sodium bisulphate, potassium pyrosulphate, tetra-alkyl titanate, titanium tetrachloride or a molecular sieve catalyst.  The ester products are suitable as lubricants or plasticizers for thermoplastic materials, e.g. polyvinyl chloride.