Patent EA-001335-B1 (EA)
Title: High stability and low metals esters based on 3,5,5-trimethyl-1-hexanol
Inventor: SCHLOSBERG RICHARD H
IPC: C10N40/25
Filed: 1997-01-16
Abstract: 1. A synthetic ester composition exhibiting thermal and oxidative stability which comprises the reaction product of 3,5,5-trimethyl-1-hexanol and an acid or anhydride; wherein said synthetic ester composition exhibits the following properties: a thermal/oxidative stability, measured by HPDSC at 220 DEG C., 3.395 MPa air and 0.5 wt. % dioctyl diphenyl amine, of at least 20 minutes; a metals content of 10 ppm or less metals based on the total synthetic ester composition; an ash content of 15 ppm or less ash based on the total synthetic ester composition; a total acid number of 0.05 mg KOH/g or less; and a volume resistivity of at least about 1.times. x 10<11> ohm cm. 2. The synthetic ester composition according to claim 1 wherein said synthetic ester composition is formed by esterification of said acid or anhydride with excess 3,5,5-trimethyl-1-hexanol and with or without a sulfuric acid, phosphorus acid, sulfonic acid, para-toluene sulfuric acid or titanium, zirconium or tin-based catalyst at a temperature in the range between about 140 DEG to 250 DEG C. and a pressure in the range between about 30 mm Hg to 760 mm Hg. 3. The synthetic ester composition according to claim 2 further comprising the step of adding an adsorbent to said reaction mixture following esterification. 4. The synthetic ester composition according to claim 3 wherein said adsorbent is at least one material selected from the group comprising: alumina, silica gel, activated carbon, zeolites, clay and filter aid. 5. The synthetic ester composition according to claim 2 further comprising the steps of:  addition of water and base to simultaneously neutralize the residual organic and mineral acids and/or hydrolyze said catalyst; removal of said water used in the hydrolysis step by heat and vacuum in a flash step; filtration of solids from said ester mixture containing the bulk of the excess alcohol used in the esterification reaction; removal of excess alcohol by steam stripping or any other distillation method and recycling of said excess alcohol to said reaction mixture; and removing any residual solids from the stripped ester in a final filtration. 6. The synthetic ester composition according to claim 1 further comprising a polyhydroxy compound and wherein said acid or anhydride is a poly acid or anhydride of a polyacid, respectively. 7. The synthetic ester composition according to claim 6 wherein said polyhydroxy compound is represented by the formula R(OH)N wherein R is an alkyl, alkenyl or aralkyl hydrocarbyl group and n is at least 2. 8. The synthetic ester composition according to claim 7 wherein said polyhydroxy compound is selected from the group consisting of: neopentyl glycol, 2,2-dimethylol butane, trimethylol ethane, trimethylol propane, trimethylol butane, monopentaerythritol, technical grade pentaerythritol, dipentaerythritol, ethylene glycol, propylene glycol, 1,4-butanediol and polyalkylene glycols, and blends thereof. 9. A lubricant which is prepared from: at least one synthetic ester composition exhibiting thermal and oxidative stability which comprises the reaction product of: 3,5,5-trimethyl-1-hexanol and an acid or anhydride; and a lubricant additive package; whereby the incorporation of an antioxidant in said lubricant additive package, for the purpose of maintaining oxidative and thermal stability of said lubricant to at least 20 minutes as measured by HPDSC at 220 DEG C., 3.395 MPa air and 0.5 wt. % dioctyl diphenyl amine, can be either reduced or eliminated. 10. The lubricant according to claim 9 wherein said synthetic ester composition exhibits the following additional properties: a metals content of 10 ppm or less metals based on the total synthetic ester composition, an ash content of 15 ppm or less ash based on the total synthetic ester composition, a total acid number of 0.05 mg KOH/g or less, and a volume resistivity of at least about 1.times x 10<11> ohm cm. 11. The lubricant according to claim 9 wherein said synthetic ester composition is formed by esterification of said acid or anhydride with excess 3,5,5-trimethyl-1-hexanol and with or without a sulfuric acid, phosphorus acid, sulfonic acid, para-toluene sulfuric acid or titanium, zirconium or tin-based catalyst at a temperature in the range between about 140 DEG to 250 DEG C. and a pressure in the range between about 30 mm Hg to 760 mm Hg. 12. The lubricant according to claim 11 further comprising the step of adding an adsorbent to said reaction mixture following esterification. 13. The lubricant according to claim 12 wherein said adsorbent is at least one material selected from the group comprising: alumina, silica gel, activated carbon, zeolites, clay and filter aid. 14. The lubricant according to claim 11 further comprising the steps of: addition of water and base to simultaneously neutralize the residual organic and mineral acids and/or hydrolyze said catalyst; removal of said water used in the hydrolysis step by heat and vacuum in a flash step; filtration of solids from said ester mixture containing the bulk of the excess alcohol used in the esterification reaction; removal of excess alcohol by steam stripping or any other distillation method and recycling of said excess alcohol to said reaction mixture; and removing any residual solids from the stripped ester in a final filtration. 15. The lubricant according to claim 9 further comprising a polyhydroxy compound and wherein said acid or anhydride is a polyacid or an anhydride of a polyacid. 16. The lubricant according to claim 15 wherein said polyhydroxy compound is represented by the formula R(OH)n wherein R is an alkyl, alkenyl or aralkyl hydrocarbyl group and n is at least 2. 17. The lubricant according to claim 16 wherein said polyhydroxy compound is selected from the group consisting of: neopentyl glycol, 2,2-dimethylol butane, trimethylol ethane, trimethylol propane, trimethylol butane, monopentaerythritol, technical grade pentaerythritol, dipentaerythritol, ethylene glycol, propylene glycol, 1,4-butanediol and polyalkylene glycols, and blends thereof. 18. The lubricant according to claim 9 wherein said lubricant is a blend of said synthetic ester composition and at least one additional base stock selected from the group consisting of mineral oils, highly refined mineral oils, poly alpha olefins, polyalkylene glycols, phosphate ester, silicone oils, diesters and polyol ester. 19. The lubricant according to claim 9 wherein said additive package comprises at least one additive selected from the group consisting of: viscosity index improvers, corrosion inhibitors, antioxidants, dispersants, lube oil flow improvers, detergents and rust inhibitors, pour point depressants, anti-foaming agents, anti-wear agents, seal swellants, friction modifiers, extreme pressure agents, color stabilizers, demulsifiers, wetting agents, water loss improving agents, bactericides, drill bit lubricants, thickeners or gellants, anti-emulsifying agents, metal deactivators, coupling agents, surfactants, and additive solubilizers. 20. A crankcase lubricating oil formulation which is prepared from: at least one synthetic ester composition which comprises the reaction product of: 3,5,5-trimethyl-1-hexanol and an acid or anhydride; and a lubricant additive package; whereby the incorporation of an antioxidant in said lubricant additive package, for the purpose of maintaining oxidative and thermal stability of said crankcase lubricating oil formulation to at least 20 minutes as measured by HPDSC at 220 DEG C., 3.395 MPa air and 0.5 wt. % dioctyl diphenyl amine, can be either reduced or eliminated. 21. The formulation according to claim 20 wherein said synthetic ester composition exhibits the following properties: a metals content of 10 ppm or less metals based on the total synthetic ester composition, an ash content of 15 ppm or less ash based on the total synthetic ester composition, a total acid number of 0.05 mg KOH/g or less, and a volume resistivity of at least about 1.times. x 10<11> ohm cm. 22. The formulation according to claim 20 wherein said additive package comprises at least one additive selected from the group consisting of: ashless dispersants, metal detergents, corrosion inhibitors, metal dihydrocarbyl dithiophosphates, pour point depressants, anti-foaming agents, anti-wear agents, friction modifiers, and viscosity modifiers. 23. The formulation according to claim 20 further comprising a blend of said synthetic ester composition and at least one additional base stock selected from the group consisting of: mineral oils, highly refined mineral oils, poly alpha olefins, polyalkylene glycols, phosphate ester, silicone oils, diesters and polyol ester. 24. A two-cycle engine oil formulation which is prepared from: at least one synthetic ester composition exhibiting thermal and oxidative stability which comprises the reaction product of: 3,5,5-trimethyl-1-hexanol and an acid or anhydride; and a lubricant additive package; whereby the incorporation of an antioxidant in said lubricant additive package, for the purpose of maintaining oxidative and thermal stability of said two-cycle engine oil formulation to at least 20 minutes as measured by HPDSC at 220 DEG C., 3.395 MPa air and 0.5 wt. % dioctyl diphenyl amine, can be either reduced or eliminated. 25. The formulation according to claim 24 wherein said synthetic ester composition exhibits the following properties: a metals content of 10 ppm or less metals based on the total synthetic ester composition, an ash content of 15 ppm or less ash based on the total synthetic ester composition, a total acid number of 0.05 mg KOH/g or less, and a volume resistivity of at least about 1.times.10@11 ohm cm.wherein said synthetic ester composition exhibits the following properties: a metals content of 10 ppm or less metals based on the total synthetic ester composition, an ash content of 15 ppm or less ash based on the total synthetic ester composition, a total acid number of 0.05 mg KOH/g o