Patent GB-791187-A (GB)
Title: Amine salts of di oxo-octyl orthophosphates and compositions including the same
IPC: C10M137/08
Filed: 1956-03-28
Abstract: The invention comprises a substantially neutral salt of a primary n-alkyl amine containing 8 to 18 carbon atoms per molecule and di-oxo-octyl acid orthophosphate.  Specified amines are n-dodecyl (lauryl) amine, n-octyl amine, n-decyl amine, n-tetradecyl amine and n-hexadecyl amine.  Also mixtures of the C8-C18 amines may be used, e.g. cocoamine (derived from coconut oil fatty acids and consisting principally of n-dodecylamine).  The di-oxo-octyl orthophosphate is preferably derived from an oxo alcohol formed by hydroformylation and hydrogenation of a mixed C7 olefin obtained by condensing C3 and C4 olefines in the proportion that they normally occur in petroleum refinery gases, i.e. in the proportion that they occur in the refining, e.g. catalytic cracking of heavier petroleum hydrocarbons. The salts may be obtained by adding to the di-oxo-octyl acid orthophosphate an approximately equimolar amount of the primary n-alkyl amine.  The reaction proceeds at room temperature with evolution of heat and the temperature should be maintained below about 200 DEG  F., e.g. by controlling the rate of addition of the amine or by external cooling, or both.  Normally, it is desirable to continue to stir the reaction mixture after amine addition is complete for about the same length of time as is required to add the amine in order to ensure completion of the reaction and the pH of the reaction product should be from about 5.5 to about 7.5 and preferably about 7.  An example is given for the preparation of the cocoamine salt (principally n-dodecyl amine salt) of a di-oxo-octyl acid orthophosphate derived from a C8 oxo alcohol obtained by the hydrogenation of a hydroformylated mixture of heptene isomers obtained by condensing a mixture of C3 and C4 olefines as above.  The di-oxo-octyl acid orthophosphate may be obtained by adding P2O5 to the oxo alcohol in a mol. ratio of about 1 : 4, while maintaining the reaction temperature below about 180 DEG  F.  The amine salt products are stated to be highly resistant to water-leaching and to impart excellent rust and corrosion inhibiting characteristics to various mineral oil compositions (see Group III).ALSO:A mineral oil or synthetic lubricant composition comprises a mineral oil or synthetic lubricant respectively and a minor amount, sufficient to impart corrosion-inhibiting characteristics to the composition, of a substantially neutral salt of a primary C8-C18 n-alkyl amine and di-oxo-octyl acid orthophosphate (see Group IV (b)).  The mineral oil may be a petroleum distillate such as gasoline, a jet engine fuel, a lubricating oil, kerosene, diesel fuel, furnace oil, or a grease composition.  Other conventional additives may also be present in the mineral oil composition, e.g. an anti-rust agent, de-icing agent, detergent, dispersant, anti-knock agent, land scavenger, sludge inhibitor, pour-point depressant, ignition control agent, antioxidant, thickener or viscosity index improver.  Specified amines from which the salt may be derived are n-octyl, n-decyl, n-dodecyl, n-tetradecyl, and n-hexadecyl amines, also mixed C8-C18 n-alkyl amines, e.g. cocoamine (derived from coconut oil fatty acids and consisting principally of n-dodecyl amine).  The di-oxo-octyl and orthophosphate is preferably derived from an oxo alcohol formed from a mixed C7 olefin obtained by condensing C3 and C4 olefines in the proportion that they normally occur in petroleum refinery gases, e.g. in the proportion that they occur in the refining, e.g. catalytic cracking, of heavier petroleum hydrocarbons.  Examples are given to shown the effect of adding a cocoamine salt of a di-n-oxo-octyl acid thiophosphate of the preferred type as a rustinhibitor to (1) a highly paraffinic turbine lubricating oil base; (2) a military grade jet engine fuel which has been previously depolarized with activated alumina; and (3) a commercial 80/87 grade aviation gasoline containing tetraethyl lead, the gasoline being previously depolarized as in (2).  Data are also given to show that the cocoamine salt of the di-oxo-octyl acid orthophosphate is considerably more resistant to water-leaching from a composition thereof in depolarized isoctane than are the neutral cocoamine salts of diisoamyl acid orthophosphate, and 3-methylbutyl, 2-ethylhexyl acid orthophosphate, respectively, from similar compositions.