# US 4,394,277 A · Method for improving fuel economy of internal combustion engines using borated sulfur-containing 1,2-alkane diols

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- Number: US 4,394,277 A
- Document ID: US4394277A
- Status: Granted
- Kind: A
- Application number: 06/314,631
- Filed: 1981-10-26
- Granted: 1983-07-19
- Earliest claimed: 1981-10-26
- Assignees: Chevron Research Company
- Inventors: Vernon R. Small, Jr.
- Web page: https://patentgrep.com/patent/US4394277A

## CPC

- C07F 5/04: Esters of boric acids
- C10M 129/10: having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
- C10M 129/95: Esters
- C10M 133/56: Amides; Imides
- C10M 135/10: Sulfonic acids or derivatives thereof
- C10M 137/10: Thio derivatives
- C10M 139/00: Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
- C10M 141/12: at least one of them being an organic compound containing atoms of elements not provided for in groups C10M141/02 - C10M141/10
- C10M 159/22: containing phenol radicals
- C10M 159/24: containing sulfonic radicals
- C10M 2207/023: having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M 2207/026: with tertiary alkyl groups
- C10M 2207/027: Neutral salts thereof
- C10M 2207/028: Overbased salts thereof
- C10M 2207/262: derived from hydroxy substituted aromatic acids, e.g. salicylates
- C10M 2207/287: Partial esters
- C10M 2207/289: containing free hydroxy groups
- C10M 2207/34: Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
- C10M 2209/00: Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M 2209/02: Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M 2209/084: Acrylate; Methacrylate
- C10M 2209/10: Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M 2215/04: having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M 2215/042: containing hydroxy groups; Alkoxylated derivatives thereof
- C10M 2215/26: Amines
- C10M 2215/28: Amides; Imides
- C10M 2217/00: Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M 2217/02: Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
- C10M 2217/04: Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M 2217/046: Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
- C10M 2217/06: Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
- C10M 2219/02: Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
- C10M 2219/044: Sulfonic acids, Derivatives thereof, e.g. neutral salts
- C10M 2219/046: Overbased sulfonic acid salts
- C10M 2219/089: Overbased salts
- C10M 2223/045: Metal containing thio derivatives
- C10M 2227/00: Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M 2227/06: Organic compounds derived from inorganic acids or metal salts
- C10M 2227/061: Esters derived from boron
- C10M 2227/062: Cyclic esters
- C10M 2227/063: Complexes of boron halides
- C10M 2227/065: derived from Ti or Zr
- C10M 2227/066: derived from Mo or W
- C10N 2010/04: Groups 2 or 12
- C10N 2040/00: Specified use or application for which the lubricating composition is intended
- C10N 2040/25: Internal-combustion engines
- C10N 2040/251: {Alcohol-fuelled engines}
- C10N 2040/255: {Gasoline engines}
- C10N 2040/28: Rotary {engines}
- C10N 2040/30: Refrigerators lubricants {or compressors lubricants}
- C10N 2040/32: Wires, ropes or cables lubricants
- C10N 2040/34: Lubricating-sealants
- C10N 2040/36: Release agents {or mold release agents}
- C10N 2040/38: {Conveyors or chain belts}
- C10N 2040/40: {Generators or electric motors in oil or gas winning field}
- C10N 2040/42: {Flashing oils or marking oils}
- C10N 2040/44: {Super vacuum or supercritical use}
- C10N 2040/50: {Medical uses}
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33)
- C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS

## Abstract

Lubricating oils containing borated sulfur-containing 1,2-alkane diols have been found to reduce fuel consumption in an internal combustion engine.

## Claims

### Claim 1

A borated sulfur-containing 1,2-alkane diol of the formula ##STR8## wherein R is alkyl containing 5 to 30 carbon atoms and m is 1 or 2.

### Claim 2 (depends on 1)

The compound of claim 1 wherein R is alkyl containing 5 to 18 carbon atoms.

### Claim 3 (depends on 1)

The compound of claim 1 wherein R is alkyl containing from 5 to 18 carbon atoms, m is 1.

### Claim 4 (depends on 1)

The compound of claim 1 wherein the borated sulfur-containing 1,2-alkane diol is borated 4-thia-1,2-hexadecane diol, borated 5-thia-1,2-hexadecane diol, borated 5-thia-1,2-heptadecane diol, borated 4-thia-1,2-heptadecane diol or borated 4-thia-1,2-octadecane diol.

### Claim 5 (depends on 4)

The compound of claim 4 wherein the borated sulfur-containing 1,2-alkane diol is borated 4-thia-1,2-hexadecane diol.

### Claim 6

The lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and a minor effective amount of a borated sulfur-containing 1,2-alkane diol friction-reducing additive of the formula ##STR9## wherein R is aklyl containing from 5 to 30 carbon atoms, m is 1 or 2.

### Claim 7 (depends on 1)

The composition of claim 1 containing from about 0.1 to 5% of said additive.

### Claim 8 (depends on 6)

The lubricating oil composition of claim 6 where R is alkyl containing 5 to 18 carbon atoms.

### Claim 9 (depends on 6)

The lubricating oil composition of claim 6 wherein R is alkyl containing from 5 to 18 carbon atoms, m is 1.

### Claim 10 (depends on 6)

The lubricating oil composition of claim 6 wherein the borated sulfur-containing 1,2-alkane diol additive is borated 4-thia-1,2-hexadecane diol, borated 5-thia-1,2-hexadecane diol, borated 5-thia-1,2-heptadecane diol, borated 4-thia-1,2-heptadecane diol, or borated 4-thia-1,2-octadecane diol.

### Claim 11 (depends on 10)

The lubricating oil composition of claim 10 wherein the borated sulfur-containing 1,2-alkane diol additive is borated 4-thia-1,2-hexadecane diol.

### Claim 12

The lubricating oil composition formulated for use in the crankcase of an internal combustion engine in order to improve the fuel comsumption of said engine comprising
(a) a major amount of an oil of lubricating viscosity; and
(b) an effective amount of each of the following:
1. from 1%-20% of an ankenyl succinimide or alkenyl succinate or mixtures thereof,
2. from 0.1%-4% of a Group II metal salt of a dihydrocarbyl dithiophosphoric acid,
3. from 0.3%-10% of a neutral or overbased alkali or alkaline earth metal hydrocarbyl sulfonate or mixtures thereof,
4. from 0.3%-27% of a neutral or overbased alkali or alkaline earth metal alkylated phenate, or mixtures thereof, and
5. from 0.1%-5% of a borated sulfur-containing 1,2-alkane diol friction modifying agent of the formula: ##STR10## wherein R is alkyl containing from 5 to 30 carbon atoms, m is 1 or 2.

### Claim 13 (depends on 12)

The lubricating oil composition of claim 12 wherein R is alkyl containing 5 to 18 carbon atoms.

### Claim 14 (depends on 12)

The lubricating oil composition according to claim 12 wherein in the borated sulfur-containing 1,2-alkane diol, R is alkyl from 5 to 18 carbon atoms, m is 1.

### Claim 15 (depends on 12)

The lubricating oil composition of claim 12 wherein the borated sulfur-containing 1,2-alkane diol friction reducing additive is borated 4-thia-1,2-hexadecane diol, borated 5-thia-1,2-hexadecane diol, borated 5-thia-1,2-heptadecane diol, borated 4-thia-1,2-heptadecane diol, or borated 5-thia-1,2-octadecane diol.

### Claim 16 (depends on 12)

The lubricating oil composition according to claim 12 wherein
(1) said alkenyl succinimide is a polyisobutenyl succinimide of a polyalkylene polyamine, and said alkenyl succinate is a polyisobutenyl succinate of a polyhydric alcohol;
(2) said metal salt of the dihydrocarbyl dithiophosphoric acid is zinc dialkyl dithiophosphate wherein the alkyl group contains from 4 to 12 carbon atoms;
(3) said metal of the neutral or overbased alkali or alkaline earth metal sulfonate is calcium, magnesium or barium or mixtures thereof;
(4) said metal of the neutral or overbased alkali or alkaline earth metal phenate is calcium, magnesium or barium;
(5) said R group of the borated sulfur-containing 1,2-alkane diol is alkyl containing from 5 to 30 carbon atoms, and m is 1.

### Claim 17 (depends on 16)

The lubricating oil composition according to claim 16 wherein
(1) said alkenyl succinimide is a polyisobutenyl succinimide of triethylenetetramine or polyisobutenyl succinimide of tetraethylenepentamine, and said alkenyl succinate is a polyisobutenyl succinate of pentaerythritol;
(2) said metal salt of the dihydrocarbyl dithiophosphoric acid is zinc O,O-di(2-ethylhexyl)dithiophosphate, zinc O,O-di(isobutyl/mixed primary hexyl)dithiophosphate, or zinc O,O-di(sec-butyl/mixed secondary hexyl)dithiophosphate;
(3) said metal salt of the sulfonate is an overbased magnesium or calcium hydrocarbyl sulfonate;
(4) said metal salt of the phenate is an overbased sulfurized calcium or magnesium monoalkylated phenate,
(5) said R group of the borated sulfur-containing 1,2-alkane diol is an alkyl containing from 5 to 18 carbon atoms.

### Claim 18 (depends on 16)

The lubricating oil composition according to claim 16 wherein the borated sulfur-containing 1,2-alkane diol additive is borated 4-thia-1,2-hexadecane diol.

### Claim 19 (depends on 1, 12)

A method for reducing the fuel consumption of an internal combustion engine by treating the moving surfaces thereof with a composition according to any one of claim 1 or 12.