Patent GB-659103-A (GB)
Title: Complex esters
IPC: C08G63/20
Filed: 1948-11-30
Abstract: A complex ester is prepared by esterifying a saturated aliphatic mono-carboxylic acid with an equimolar proportion of a glycol to form a half ester, and esterifying two molar proportions thereof with one of an aliphatic or aromatic dicarboxylic acid.  Esters for use as lubricants may have the formula <FORM:0659103/IV (a)/1> where R1 and R11 are saturated C2-C20 aliphatic hydrocarbon radicals or a series of such C2 or higher radicals linked by one or more ether oxygen and/or thioether sulphur atoms, the total number of C, O, and S atoms being 5-80 and the number of S atoms not more than 2, R2 and R12 are C1-C22 saturated aliphatic hydrocarbon radicals or similar radicals wherein up to 5 of the C atoms are replaced by ether oxygen atoms, there being at least 1 C atom between the carboxyl group and the first O atom, and at least 2 C atoms between each pair of O atoms, or wherein 1 C atom has been replaced by a thioether sulphur atom; R3 is an aliphatic hydrocarbon radical containing up to 30 C atoms or a series of C2 or higher, such radicals linked by 1 or more ether oxygen and/or thioether sulphur atoms, the total number of C, O, and S atoms being 3-80 and the number of S atoms not more than 2, and there being at least 1 C atom between each carboxyl group and the nearest O or S or R3 is an aromatic nucleus containing not more than 2 and preferably 1 aromatic ring with or without aliphatic substituents up to a total of 16 C atoms; and the starting materials are so chosen that the molecular weight of the product is at least 300 and its viscosity at 210 DEG  F. not more than 150 Saybolt seconds.  Preferred glycols are polyethylene glycols HO(CH2CH2O)nCH2CH2OH, where n is 1-26.  Preferred monocarboxylic acids are fatty acids of 2-10 C atoms; preferred dicarboxylic acids are straight-chain paraffinic acids of 6-10 C atoms.  Numerous examples of these are given.  The preparation and properties of esters from valeric, caproic, caprylic, acetic, propionic or butyric acid; ethylene glycol or tri-, tetra- or higher polyglycols or thiodiglycol; and adipic and/or sebacic, thiodipropionic or terephthalic acid are described.  They may be blended with mineral oils, and antioxidants, and other additives incorporated.ALSO:A complex ester is prepared by esterifying a saturated aliphatic monocarboxylic acid with an equimolar proportion of a glycol to form a half ester, and esterifying two molar proportions thereof with one of an aliphatic or aromatic dicarboxylic acid.  Esters for use as lubricants may have the formula R2.COO-R1-OOC-R3-COO.R11 -OOC.R12 where R1 and R11 are saturated C2-C20 aliphatic hydrocarbon radicals or a series of such C2 or higher radicals linked by one or more ether oxygen and/or thioether sulphur atoms, the total number of p  C, O, and S atoms being 5-80 and the number of S atoms not more than 2; R2 and R12 are C1-C22 saturated aliphatic hydrocarbon radicals or similar radicals wherein up to 5 of the C atoms are replaced by ether oxygen atoms, there being at least 1 C atom between the carboxyl group and the first O atom, and at least 2 C atoms between each pair of O atoms, or wherein 1 C atom has been replaced by a thioether sulphur atom; R3 is an aliphatic hydrocarbon radical containing up to 30 C atoms or a series of C2 or higher such radicals linked by 1 or more ether oxygen and/or thioether sulphur atoms, the total number of C, O, and S atoms being 3-80 and the number of S atoms not more than 2, and there being at least 1 C atom between each carboxyl group and the nearest O or S, or R3 is an aromatic nucleus containing not more than 2 and preferably 1 aromatic ring with or without aliphatic substituents up to a total of 16 C atoms; and the starting materials are so chosen that the molecular weight of the product is at least 300 and its viscosity at 210 DEG  F. not more than 150 Saybolt seconds.  Preferred glycols are polyethylene glycols HO(CH2CH2 O)nCH2CH2OH where n is 1-26.  Preferred monocarboxylic acids are fatty acids of 2-10 C atoms; preferred dicarboxylic acids are straight chain paraffinic acids of 6-10 C atoms.  Numerous examples of these are given.  The preparation and properties of esters from valeric, caproic, caprylic, acetic, propionic or butyric acid; ethylene glycol or tri-, tetra- or higher poly-glycols or thiodiglycol; and adipic and/or sebacic, thiodipropionic or terephthalic acid are described. Esterification is effected in toluene with p-toluene sulphonic acid monohydrate as catalyst.  They may be blended with mineral oils, and antioxidants, and other additives incorporated.ALSO:A complex ester is prepared by esterifying a saturated aliphatic monocarboxylic acid with an equimolar proportion of a glycol to form a half ester, and esterifying two molar proportions thereof with one of an aliphatic or aromatic dicarboxylic acid.  Esters for use as lubricants may have the formula R2COO-R1-OOC-R3 -COO.R11-OOC.R12 where R1 and R11 are saturated C2-C20 aliphatic hydrocarbon radicals or a series of such C2 or higher radicals linked by one or more ether oxygen and/or thioether sulphur atoms, the total number of C, O, and S atoms being 5-80 and the number of S atoms not more than 2; R2 and R12 are C1-C22 saturated aliphatic hydrocarbon radicals or similar radicals wherein up to 5 of the C atoms are replaced by ether oxygen atoms, there being at least 1 C atom between the carboxyl group and the first O atom, and at least 2 C atoms between each pair of O atoms, or wherein 1 C atom has been replaced by a thioether sulphur atom; R3 is an aliphatic hydrocarbon radical containing up to 30 C atoms or a series of C2 or higher such radicals linked by 1 or more ether oxygen and/or thioether sulphur atoms, the total number of C, O, and S atoms being 3-80 and the number of S atoms not more than 2, and there being at least 1 C atom between each carboxyl group and the nearest O or S, or R3 is an aromatic nucleus containing not more than 2 and preferably 1 aromatic ring with or without aliphatic substituents up to a total of 16 C atoms; and the starting materials are so chosen that the molecular weight of the product is at least 300 and its viscosity at 210 DEG  F. not more than 150 Saybolt seconds.  Preferred glycols are polyethylene glycols HO(CH2CH2O)nCH2CH2 OH where n is 1-26. Preferred monocarboxylic acids are fatty acids of 2-10 C atoms; preferred dicarboxylic acids are stright chain paraffinic acids of 6-10 C atoms.  Numerous examples of these are given.  The preparation and properties of esters from valeric, caproic, caprylic, acetic, propionic or butyric acid; ethylene glycol or tri-, tetra- or higher polyglycols or thiodiglycol; and adipic and/or sebacic, thiodipropionic or terephthalic acid are described.  They may be blended with mineral oils, and antioxidants, and other additives incorporated.