# US 4,380,498 A · Sulfurized, transesterified oil additives and their use in a lubricating oil and a fuel

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- Number: US 4,380,498 A
- Document ID: US4380498A
- Status: Granted
- Kind: A
- Application number: 06/291,544
- Filed: 1981-08-10
- Granted: 1983-04-19
- Earliest claimed: 1981-08-10
- Assignees: Ferro Corporation
- Inventors: Karl P. Kammann, Jr.; Marvin J. Den Herder; Terrence L. Wagner
- Web page: https://patentgrep.com/patent/US4380498A

## CPC

- C07C 323/00: Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C10L 1/2493: {compounds of uncertain formula; reactions of organic compounds (hydrocarbons, acids, esters) with sulfur or sulfur containing compounds}
- C10M 135/06: Esters, e.g. fats
- C10M 2219/024: of esters, e.g. fats
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- 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)

## Abstract

Improved lubricant additive compositions, derived from fatty oils, comprise triglycerides which have been transesterified with polybasic carboxylic acids prior to sulfurization. Such additive compositions possess improved solubility in oils and impart improved lubrication properties to both lubricant and fuel compositions.

## Claims

### Claim 1

A sulfurized, triglyceride additive composition comprising a sulfurized, transesterified triglyceride wherein the total acid component of the triglyceride includes from about 5 to about 50 mole % polybasic carboxylic acids.

### Claim 2 (depends on 1)

The composition of claim 1 wherein the polybasic carboxylic acids comprise dibasic acids having from about 3 to about 36 carbon atoms per molecule.

### Claim 3 (depends on 2)

The composition of claim 2 wherein the dibasic acids comprise unsaturated acids having from about 21 to about 36 carbon atoms.

### Claim 4 (depends on 3)

The composition of claim 3 wherein the unsaturated dibasic acids comprise dimerized linoleic acid.

### Claim 5 (depends on 3)

The composition of claim 3 wherein the unsaturated dibasic acids comprise the dimerized product of linoleic and acrylic acids.

### Claim 6 (depends on 1)

The composition of claim 1 wherein the polybasic carboxylic acids comprise a mixture of dibasic and tribasic acids having from about 3 to about 54 carbon atoms per molecule.

### Claim 7 (depends on 6)

The composition of claim 6 wherein the mixture of dibasic and tribasic acids comprises unsaturated acids having from about 21 to about 54 carbon atoms.

### Claim 8 (depends on 7)

The composition of claim 7 wherein the mixture of unsaturated dibasic and tribasic acids comprises dimers and trimers of linoleic acid.

### Claim 9 (depends on 1)

The composition of claim 1, additionally comprising a solubilization agent.

### Claim 10 (depends on 9)

The composition of claim 9 wherein the solubilization agent is selected from the group consisting of triglycerides, olefins, esters of unsaturated carboxylic acids, and mixtures thereof.

### Claim 11 (depends on 10)

The composition of claim 10 wherein the solubilization agent is a triglyceride.

### Claim 12 (depends on 10)

The composition of claim 10 wherein the solubilization agent is an olefin.

### Claim 13 (depends on 12)

The composition of claim 12 wherein the olefin contains from about 8 to about 20 carbon atoms, alone or in mixtures thereof.

### Claim 14 (depends on 10)

The composition of claim 10 wherein the solubilization agent is an ester of an unsaturated carboxylic acid.

### Claim 15 (depends on 9)

The composition of claim 9 wherein the solubilization agent is present in an amount within the range from about 5 wt. % to about 70 wt. %, based on the sulfurized, transesterified triglyceride.

### Claim 16 (depends on 15)

The composition of claim 15 wherein the solubilization agent is present in an amount within the range from about 5 wt. % to about 55 wt. %, based on the sulfurized, transesterified triglyceride.

### Claim 17 (depends on 1)

The composition of claim 1 wherein bound sulfur is present in an amount within the range from about 2 wt. % to about 10 wt. %, based on the sulfurized, transesterified triglyceride.

### Claim 18

A process for preparing a sulfurized, transesterified triglyceride additive composition, comprising the steps of:
(1) transesterifying one or more triglycerides with one or more organic polybasic acids, or esters thereof, to yield a transesterified triglyceride wherein the total acid component comprises from about 5 mole % to about 50 mole % polybasic carboxylic acids; and
(2) sulfurizing the transesterified triglyceride product mixture of step 1 with elemental sulfur to incorporate bound sulfur in an amount within the range from about 2 wt. % to about 10 wt. %, based upon the transesterified triglyceride product mixture.

### Claim 19 (depends on 18)

The process of claim 18, wherein said polybasic carboxylic acids comprise dibasic acids having from about 3 to about 36 carbon atoms per molecule.

### Claim 20 (depends on 19)

The process of claim 19, wherein said dibasic acids comprise unsaturated acids having from about 21 to about 36 carbon atoms.

### Claim 21 (depends on 20)

The process of claim 20, wherein said unsaturated dibasic acids comprise dimerized linoleic acid.

### Claim 22 (depends on 20)

The process of claim 20, wherein said unsaturated dibasic acids comprise the dimerized product of linoleic and acrylic acids.

### Claim 23 (depends on 18)

The process of claim 18, wherein said polybasic carboxylic acids comprise a mixture of dibasic and tribasic acids having from about 3 to about 54 carbon atoms per molecule.

### Claim 24 (depends on 23)

The process of claim 23, wherein said mixture of dibasic and tribasic acids comprises unsaturated acids having from about 21 to about 54 carbon atoms.

### Claim 25 (depends on 24)

The process of claim 24, wherein said mixture of unsaturated dibasic and tribasic acids comprises dimers and trimers of linoleic acid.

### Claim 26 (depends on 18)

The process of claim 18, additionally comprising the step of esterifying free acids in the transesterification reaction product with an alcohol component prior to the sulfurization step.

### Claim 27 (depends on 26)

The process of claim 26 wherein said alcohol component for esterification comprises branched chain aliphatic primary alcohols.

### Claim 28 (depends on 18)

The process of claim 18, additionally comprising the step of blending said transesterification reaction product with a compound selected from the group consisting of triglycerides, esterified fatty acids, .alpha.-olefins and mixtures thereof, prior to the sulfurization step.

### Claim 29 (depends on 18)

The process of claim 18, wherein said transesterification step is carried out in the presence of a transesterification catalyst.

### Claim 30 (depends on 18)

The process of claim 18, wherein said transesterification catalyst is selected from the group consisting of tetrabutyl titanate, zinc acetate, sodium carbonate, sodium sulfate, stannous oxalate, p-toluenesulfonic acid, methanesulfonic acid, sulfuric acid, butylchlorotin dihydroxide, and phosphoric acid.

### Claim 31 (depends on 29)

The process of claim 29, wherein said transesterification catalyst is present in an amount within the range from about 0.01 to about 1 wt. %, based on the triglycerides.

### Claim 32 (depends on 31)

The process of claim 31, wherein said catalyst is present in an amount within the range from about 0.03 to about 0.5 wt. %.

### Claim 33 (depends on 30)

The process of claim 30 wherein said catalyst is p-toluenesulfonic acid.

### Claim 34 (depends on 30)

The process of claim 30, wherein said catalyst is methanesulfonic acid.

### Claim 35

A lubricating oil composition, comprising:
(1) a refined base oil, having lubricating oil viscosity and volatility properties; and
(2) a minor amount, from about 0.05 to about 15 wt. % of the lubricating oil composition, of a sulfurized, triglyceride additive composition, comprising a sulfurized, transesterified triglyceride wherein the total acid component of the triglyceride includes from about 5 to about 50 mole % polybasic carboxylic acids.

### Claim 36 (depends on 35)

The lubricating oil composition of claim 35 wherein the sulfurized triglyceride additive composition is present in an amount within the range from about 0.5 to about 5 wt. % of the lubricating oil composition.

### Claim 37

A fuel composition, comprising:
(1) a blended base fuel, having suitable volatility and combustion properties; and
(2) a minor amount, from about 0.0005 to about 0.1 wt. % of the fuel composition, of a sulfurized triglyceride additive composition, comprising a sulfurized, transesterified triglyceride wherein the total acid component of the triglyceride includes from about 5 to about 50 mole % polybasic carboxylic acids.

### Claim 38 (depends on 37)

The fuel composition of claim 37 wherein the blended base fuel is a gasoline fuel, for use in a spark-ignition internal combustion engine.

### Claim 39 (depends on 37)

The fuel composition of claim 37 wherein the blended base fuel is a diesel fuel, for use in a compression-ignition internal combustion engine.

### Claim 40 (depends on 37)

The fuel composition of claim 37 wherein the blended base fuel is a heating oil, for use in an oil-fired burner assembly.

### Claim 41 (depends on 37)

The fuel composition of claim 37 wherein the sulfurized triglyceride additive composition is present in an amount within the range from about 0.0015 to about 0.05 wt. % of the fuel composition.