# US 4,394,276 A · Method for improving fuel economy of internal combustion engines using sulfur-containing alkanediols

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- Number: US 4,394,276 A
- Document ID: US4394276A
- Status: Granted
- Kind: A
- Application number: 06/314,630
- 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/US4394276A

## CPC

- C10M 141/10: at least one of them being an organic phosphorus-containing compound
- C10M 129/10: having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
- C10M 133/52: having a carbon chain of 30 or more atoms
- C10M 135/10: Sulfonic acids or derivatives thereof
- C10M 135/24: containing hydroxy groups; Derivatives thereof
- C10M 135/30: containing hydroxy groups; Derivatives thereof
- C10M 137/10: Thio derivatives
- C10M 2205/00: Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M 2205/06: containing conjugated dienes
- 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 2207/289: containing free hydroxy groups
- C10M 2209/084: Acrylate; Methacrylate
- C10M 2215/04: having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M 2215/042: containing hydroxy groups; Alkoxylated derivatives thereof
- C10M 2215/086: Imides [having hydrocarbon substituents containing less than thirty carbon atoms]
- C10M 2215/22: Heterocyclic nitrogen compounds
- C10M 2215/221: Six-membered rings containing nitrogen and carbon only
- C10M 2215/225: the rings containing both nitrogen and oxygen
- C10M 2215/226: Morpholines
- C10M 2215/24: having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M 2215/26: Amines
- C10M 2215/28: Amides; Imides
- C10M 2215/30: Heterocyclic compounds
- 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 2219/044: Sulfonic acids, Derivatives thereof, e.g. neutral salts
- C10M 2219/046: Overbased sulfonic acid salts
- C10M 2219/084: containing hydroxy groups; Derivatives thereof
- C10M 2219/087: containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M 2219/088: Neutral salts
- C10M 2219/089: Overbased salts
- C10M 2223/045: Metal containing thio derivatives
- C10N 2010/04: Groups 2 or 12
- C10N 2040/25: Internal-combustion engines
- C10N 2040/251: {Alcohol-fuelled engines}
- C10N 2040/255: {Gasoline engines}
- C10N 2040/28: Rotary {engines}
- 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 sulfur-containing alkane diols have been found to reduce fuel consumption in an internal combustion engine.

## Claims

### Claim 1

A lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and a minor effective amount of a sulfur-containing alkane diol fricton-reducing additive of the formula ##STR6## wherein R is alkyl containing from 5 to 30 carbon atoms, m is 1 or 2 and n is 0 or 1.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

The lubricating oil composition of claim 1 wherein R is alkyl containing from 5 to 30 carbon atoms, m is 1 and n is 0.

### Claim 4 (depends on 1, 3)

The lubricating oil composition of claim 1 or 3 where R is alkyl containing 5 to 18 carbon atoms.

### Claim 5 (depends on 1)

The lubricating oil composition of claim 1 wherein the sulfur-containing alkane diol additive is 4-thia-1,2-hexadecane diol, 5-thia-1,2-heptadecane diol, 5-thia-1,3-heptadecane diol, or 6-thia-1,3-octadecane diol.

### Claim 6 (depends on 5)

The lubricating oil compositon of claim 5 wherein the sulfur-containing alkane diol additive is 4-thia-1,2-hexadecane diol.

### Claim 7

A lubricating oil composition formulated for use in the crankcase of an internal combustion engine in order to improve the fuel consumption 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 alkenyl succinimide or alkenyl succinate, or mixture 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 0.2%-27% of a neutral or overbased alkali or alkaline earth metal alkylated phenate, or mixtures thereof, and
(5) from 0.1%-5% of sulfur-containing alkane diol friction modifying agent of the formula ##STR7## wherein R is alkyl containing from 5 to 30 carbon atoms, R.sup.1 is hydrogen or alkyl containing from 1 to 4 carbon atoms, m is 1 or 4 and n is 0 or 1.

### Claim 8 (depends on 7)

The lubricating oil composition according to claim 7 wherein in the sulfur-containing alkane diol, R is alkyl from 5 to 30 carbon atoms, m is 1, and n is 0.

### Claim 9 (depends on 7, 8)

The lubricating oil composition of claim 7 or 8 wherein R is alkyl containing 5 to 18 carbon atoms.

### Claim 10 (depends on 7)

The lubricating oil composition of claim 7 wherein the sulfur-containing alkane diol friction reducing additive is 4-thia-1,2-hexadecane diol, 5-thia-1,2-heptadecane diol, 5-thia-1,3-heptadecane diol, or 6-thia-1,3-octadecane diol.

### Claim 11 (depends on 7)

The lubricating oil composition according to claim 7 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 sulfur-containing alkane diol is alkyl containing from 5 to 30 carbon atoms, m is 1 and n is 0.

### Claim 12 (depends on 11)

The lubricating oil composition according to claim 11 wherein
(1) said alkenyl succinimide is a polyisobutenyl succinimide of triethylenetetramine or polyisobutenyl succinimide of tetraethylenepentamine, and said alkenyl succinate s a polyisobutenyl succinate of pentaerythritol;
(2) said metal salt of the dihydrocarbyl dithiophosphoric acid is zinc 0,0-di(2-ethylhexyl)dithiophosphate, zinc 0,0-di(isobutyl/mixed primary hexyl)dithiophosphate, or zinc 0,0-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 sulfur-containing alkane diol is an alkyl containing from 5 to 18 carbon atoms.

### Claim 13 (depends on 12)

The lubricating oil composition according to claim 12 wherein the sulfur-containing alkane diol additive is 4-thia-1,2-hexadecane diol.

### Claim 14 (depends on 1, 7)

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 7.