Patent GB-606407-A (GB)
Title: Improvements in esters and process for making them
IPC: C07C69/24
Filed: 1946-01-15
Abstract: The monohydroxy 1,2 - polyoxypropylene monoalkyl ethers of average molecular weight of at least 496 described in Specification 601,604 are esterified by reaction with a fatty acid or anhydride, halide or ester thereof to give products of improved viscosity index for use as lubricants, in particular in rolling metals, e.g. aluminium, being compatible with resins used in lacquers for metal foils.ALSO:The monohydroxy 1,2-polyoxypropylene monoalkyl ethers of average molecular weight of at least 49.6, described in Specification 601,604, are esterified partially or completely by reacting with a fatty acid or anhydride, halide or ester thereof. The products have an improved viscosity index and are used as lubricating and energy transmission fluids.  They are useful lubricants in rolling metals, e.g. aluminium, being compatible with resins used in lacquers for metal foils, and are plasticizers for cellulose derivatives.  With fatty acids of 9 or more carbon atoms, preferably one mol of the acid is heated with three or four mols of the monohydroxy compound.  With fatty acids of 2-8 carbon atoms, one mol of monohydroxy compound is heated with at least one of acid.  Fatty acids of 2-19 carbon atoms are preferred, p  those from propionic to hexanoic, lauric and recinoleic being specified.  In examples: (1) monohydroxy 1,2-polyoxypropylene monobutyl ether average M.W.684, is heated with about 1/4 molar equivalent of stearic acid, and benzene sulphonic acid, at 160-165 DEG  C. in a stream of CO2.  Borax is added to neutralize, and the product treated with decolorizing carbon and filtered through diatomaceous earth.  Viscosity and load-carrying capacity figures given; (2) a similar monohydroxy compound of higher M.W. is esterified in like manner using 1/3 molar equivalent of acid; (3) 2-ethylbutyric acid is used in approximately equivalent amount, heating at 165-170 DEG  C. and 55 mm.  The product is stripped of volatile material, neutralized, and the ester layer again stripped and filtered; (4) 2-ethyl hexanoic acid is used at 165-170 DEG  C. and 10 mm.; (5) and (6) with acetic anhydride, a temperature rising from 30-110 DEG  C. is used at 85-100 mm., or 100 DEG  C. at atmospheric pressure; (7) and (8) oleic acid or acetyl chloride is the esterifying agent.ALSO:The monohydroxy 1,2 - polyoxypropylene monoalkyl ethers of average molecular weight of at least 496 described in Specification 601,604, as open to inspection under Sect. 91, are esterified partially or completely by reacting with a fatty acid or anhydride, halide or ester thereof.  The products have an improved viscosity index and are used as lubricating and energy transmission fluids.  They are useful lubricants in rolling metals, e.g. aluminium, being compatible with resins used in lacquers for metal foils, and are plasticisers for cellulose derivatives.  With fatty acids of 9 or more carbon atoms, preferably one mol. of the acid is heated with three or four mols. of the monohydroxy compound. With fatty acids of 2-8 carbon atoms, one mol. of monohydroxy compound is heated with at least one of acid.  Fatty acids of 2-19 carbon atoms are preferred, those from propionic to hexanoic, lauric and ricinoleic being specified.  In examples: (1) monohydroxy 1,2-polyoxypropylene monobutyl ether, average M.W. 684, is heated with about 1/4 molar equivalent of stearic acid, and benzene sulphonic acid, at 160-165 DEG  C. in a stream of CO2. Borax is added to neutralize, and the product treated with decolorizing carbon and filtered through diatomaceous earth. Viscosity and load-carrying capacity figures are given; (2) a similar monohydroxy compound of higher M.W. is esterified in like manner using 1/3 molar equivalent of acid; (3) 2-ethylbutyric acid is used in approximately equivalent amount, heating at 165-170 DEG  C. and 55 mm.  The product is stripped of volatile material, neutralized, and the ester layer again stripped and filtered; (4) 2-ethyl hexanoic acid is used at 165-170 DEG  C. and 10 mm.; (5) and (6) with acetic anhydride, a temperature rising from 30-110 DEG  C. is used at 85-100 mm., or 100 DEG  C. at atmospheric pressure; (7) and (8) oleic acid or acetyl chloride is the esterifying agent.