LUBRICATING COMPOSITION CONTAINING 1,3-DIOXOLANE-4-METHANOL COMPOUNDS AS ANTIWEAR ADDITIVES

• US 20120129744A1
• Filed: 11/22/2010
• Published: 05/24/2012
• Est. Priority Date: 11/22/2010
• Status: Active Grant

• Current Assignee: Chevron Oronite Company LLC (Chevron Corp.)
• Original Assignee: Chevron Oronite Company LLC (Chevron Corp.)
• Inventors: McDougall, Patrick J.
• Granted Patent: US 8,349,777 B2
• Time in Patent Office: Days
• US Class Current: 508/307
• CPC Class Codes: C10M 129/20 Cyclic ethers having 4 or more ring atoms, e.g. furans, dioxolanes
• CPC Class Codes: C10M 2203/1025 used as base material
• CPC Class Codes: C10M 2207/044 Cyclic ethers having four or more ring atoms, e.g. furans, dioxolanes
• CPC Class Codes: C10M 2207/281 of (cyclo)aliphatic monocarboxylic acids
• CPC Class Codes: C10M 2207/289 containing free hydroxy groups
• CPC Class Codes: C10M 2215/064 Di- and triaryl amines
• CPC Class Codes: C10M 2215/28 Amides; Imides
• CPC Class Codes: C10M 2219/046 Overbasedsulfonic acid salts
• CPC Class Codes: C10M 2223/045 Metal containing thio derivatives
• CPC Class Codes: C10M 2227/09 Complexes with metals
• CPC Class Codes: C10N 2010/04 Groups 2 or 12
• CPC Class Codes: C10N 2010/12 Groups 6 or 16
• CPC Class Codes: C10N 2020/04 Molecular weight; Molecular weight distribution
• CPC Class Codes: C10N 2030/06 Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
• CPC Class Codes: C10N 2030/52 Base number [TBN]
• CPC Class Codes: C10N 2040/04 Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
• CPC Class Codes: C10N 2040/135 Steam engines or turbines
• CPC Class Codes: C10N 2040/25 Internal-combustion engines
• CPC Class Codes: C10N 2040/251 Alcohol fueled engines
• CPC Class Codes: C10N 2040/252 Diesel engines
• CPC Class Codes: C10N 2040/255 : Gasoline engines
• CPC Class Codes: C10N 2040/26 : Two-strokes or two-cycle engines
• CPC Class Codes: C10N 2060/06 : by epoxydes or oxyalkylation reactions

Abstract

Disclosed are lubricating oil compositions comprising a major amount of an oil of lubricating viscosity; and from 0.05 to 10 weight % based upon the total lubricating oil composition of a 1,3-dioxolane-4-methanol compound of the formula I:

• • wherein:
  • R₁ and R₂ are each independently hydrogen, alkyl or alkenyl, wherein the sum of carbon atoms for R₁ and R₂ is 6 carbon atoms or less.

Claims

1. A lubricating oil composition comprising a major amount of an oil of lubricating viscosity;

and from 0.05 to 10 weight % based upon the total lubricating oil composition of a 1,3-dioxolane-4-methanol compound of the formula I;

2. The lubricating oil composition of claim 1, where R₁ is hydrogen and R₂ is alkyl from 1 to 6 carbon atoms.

3. The lubricating composition of claim 1 wherein the compound of formula I is selected from the group consisting of:

(2-methyl-1,3-dioxolan-4-yl)methanol, (2-ethyl-1,3-dioxolan-4-yl)methanol, (2-propyl-1,3-dioxolan-4-yl)methanol, (2-pentyl-1,3-dioxolan-4-yl)methanol, (2-hexyl-1,3-dioxolan-4-yl)methanol(2-methyl-1,3-dioxolan-4-yl)methanol, (2-sec-butyl)-1,3-dioxolan-4-yl)methanol, (2-pentan-2-yl)-1,3-dioxolan-4-yl)methanol, (2-hexyl-2-yl)-1,3-dioxolan-4-yl)methanol, (2-(3-methylpentan-2-ylpentan-2yl)-1,3-dioxolan-4-yl)methanol, (2-(4-methylpentan-2-ylpentan-2yl)-1,3-dioxolan-4-yl)methanol, (2-isopentyl-1,3-dioxolan-4-yl)methanol, (2-(2,3-dimethylbutyl)-1,3-dioxolan-4-yl)methanol, (2-(3,3-dimethylbutyl)-1,3-dioxolan-4-yl)methanol, and (2-neopentyl-1,3-dioxolan-4-yl)methanol.

4. The lubricating oil composition of claim 1, where R₁ is hydrogen and R₂ is alkenyl from 1 to 6 carbon atoms.

5. The lubricating composition of claim 1 wherein the compound of formula I is selected from the group consisting of:

(2-vinyl-1,3-dioxolan-4-yl)methanol, (2-(prop-1-en-1-yl)-1,3-dioxolan-4-yl)methanol, (2-(but-1-en-1-yl)-1,3-dioxolan-4-yl)methanol, (2-(pent-1-en-1-yl)-1,3-dioxolan-4-yl)methanol, (2-(3-methylbut-1-en-1-yl)-1,3-dioxolan-4-yl)methanol, (2-allyl-1,3-dioxolan-4-yl)methanol, (2-(but-2-en-1-yl)-1,3-dioxolan-4-yl)methanol, (2-(pent-2-en-1-yl)-1,3-dioxolan-4-yl)methanol, (2-(hex-2-en-1-yl)-1,3-dioxolan-4-yl)methanol, (2-(4-methylpent-2-en-1-yl)-1,3-dioxolan-4-yl)methanol, (2-(but-3-en-1-yl)-1,3-dioxolan-4-yl)methanol, (2-(pent-3-en-1-yl)-1,3-dioxolan-4-yl)methanol, (2-(hex-3-en-1-yl)-1,3-dioxolan-4-yl)methanol, (2-(2-methylpent-3-en-1-yl)-1,3-dioxolan-4-yl)methanol, (2-(pent-4-en-1-yl)-1,3-dioxolan-4-yl)methanol, (2-(hex-4-en-1-yl)-1,3-dioxolan-4-yl)methanol, (2-(3-methylpent-4-en-1-yl)-1,3-dioxolan-4-yl)methanol, (2-(2-methylpent-4-en-1-yl)-1,3-dioxolan-4-yl)methanol, and (2-(hex-5-en-1-yl)-1,3-dioxolan-4-yl)methanol.

6. The lubricating oil composition of claim 1, wherein R₁ and R₂ each contain carbon atoms.

7. The lubricating oil composition of claim 6, wherein R₁ and R₂ are alkyl group.

8. The lubricating oil composition of claim 1 wherein the compound of formula I is selected from the group consisting of:

(2,2-dimethyl-1,3-dioxolan-4-yl)methanol, (2-ethyl-2-methyl-1,3-dioxolan-4-yl)methanol, (2-methyl-2-propyl-1,3-dioxolan-4-yl)methanol, (2-butyl-2-methyl-1,3-dioxolan-4-yl)methanol, (2-methyl-2-pentyl-1,3-dioxolan-4-yl)methanol, (2-isopentyl-2-methyl-1,3-dioxolan-4-yl)methanol, (2-methyl-2-(2-methylbutyl)-1,3-dioxolan-4-yl)methanol, (2-isobutyl-2-methyl-1,3-dioxolan-4-yl)methanol, (2-methyl-2-neopentyl-1,3-dioxolan-4-yl)methanol, (2,2-diethyl-1,3-dioxolan-4-yl)methanol, (2-ethyl-2-propyl-1,3-dioxolan-4-yl)methanol, (2-butyl-2-ethyl-1,3-dioxolan-4-yl)methanol, (2-ethyl-2-isobutyl-1,3-dioxolan-4-yl)methanol, and (2-2-dipropyl-1,3-dioxolan-4-yl)methanol.

9. The lubricating oil composition of claim 6, wherein at least one R₁ and R₂ is an alkenyl group.

10. The lubricating oil composition of claim 1 wherein the compound of formula I is selected from the group consisting of:

(1,3-dioxolan-4-yl)methanol containing compounds are selected from the group consisting of;

(2-methyl-2-vinyl-1,3-dioxolan-4-yl)methanol, (2-methyl-2-(prop-1-en-1-yl)-1,3-dioxolan-4-yl)methanol, (2-(but-1-en-1-yl)-2-methyl-1,3-dioxolan-4-yl)methanol, 2-methyl-2-(pent-1-en-1-yl)-1,3-dioxolan-4-yl)methanol, 2-methyl-2-(3methylbut-1-en-1-yl)-1,3-dioxolan-4-yl)methanol, 2-(but-1-en-1-yl)-2-ethyl-1,3-dioxolan-4-yl)methanol, 2-allyl-2methyl-1,3-dioxolan-4-yl)methanol, (2-(but-2-en-1-yl)-2-methyl-1,3-dioxolan-4-yl)methanol, (2-methyl-2-(pent-2-en-1-yl)-2-methyl-1,3-dioxolan-4-yl)methanol, (2-(but-1-en-1-yl)-2-ethyl-1,3-dioxolan-4-yl)methanol, (2-(but-3-en-1-yl)-2-methyl-1,3-dioxolan-4-yl)methanol, (2-methyl-2-(pent-3-en-1-yl)-2-methyl-1,3-dioxolan-4-yl)methanol, (2-methyl-2-(pent-4-en-1-yl)-1,3-dioxolan-4-yl)methanol.

11. The lubricating oil composition of claim 1 wherein the compound of formula I is (1,3-dioxolan-4-yl)methanol.

12. The lubricating oil composition of claim 1 wherein the compound of formula I is from 0.1 wt % to 1.5 wt % based upon the total weight of the lubricating oil composition.

13. The lubricating oil composition of claim 1 further comprising at least one additive selected from dispersants, detergents, antiwear agents, extreme pressure agents, antioxidants, rust inhibitors, corrosion inhibitors, pour point depressants, viscosity index improvers, and friction modifiers.

14. The lubricating oil composition of claim 13 wherein the at least one additive is a metal-containing detergent in an amount from 0.25 to 3 wt % based upon the total amount of the lubricating oil composition.

15. A method for reducing wear on a gear surface or in an internal combustion engine comprising operating said gear or engine with a lubricating oil composition according to any one of the preceding claims.