# US 4,397,749 A · Oil-soluble metal thiolate-succinimide complexes

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- Number: US 4,397,749 A
- Document ID: US4397749A
- Status: Granted
- Kind: A
- Application number: 06/344,140
- Filed: 1982-01-29
- Granted: 1983-08-09
- Earliest claimed: 1982-01-29
- Assignees: Chevron Research Company
- Inventors: Michael A. Shippey
- Web page: https://patentgrep.com/patent/US4397749A

## CPC

- C07F 11/005: {compounds without a metal-carbon linkage}
- C07F 15/025: {without a metal-carbon linkage}
- C07F 15/045: {without a metal-carbon linkage}
- C07F 15/065: {without a metal-carbon linkage}
- C10M 159/18: Complexes with metals
- C10M 2205/026: Butene
- C10M 2207/08: Aldehydes; Ketones
- C10M 2207/09: Metal enolates, i.e. keto-enol metal complexes
- C10M 2207/34: Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
- C10M 2211/08: Halogenated waxes
- C10M 2219/02: Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
- C10M 2219/022: of hydrocarbons, e.g. olefines
- C10M 2219/024: of esters, e.g. fats
- C10M 2219/062: having carbon-to-sulfur double bonds
- C10M 2219/068: Thiocarbamate metal salts
- C10M 2219/09: Heterocyclic compounds containing no sulfur, selenium or tellurium compounds in the ring
- C10M 2223/04: Phosphate esters
- C10M 2223/042: Metal salts thereof
- C10M 2227/09: Complexes with metals
- C10N 2010/02: Groups 1 or 11
- C10N 2010/04: Groups 2 or 12
- C10N 2010/08: Groups 4 or 14
- C10N 2010/10: Groups 5 or 15
- C10N 2010/12: Groups 6 or 16
- C10N 2010/14: Group 7
- C10N 2010/16: Groups 8, 9, or 10
- C10N 2040/00: Specified use or application for which the lubricating composition is intended
- C10N 2040/08: Hydraulic fluids, e.g. brake-fluids
- 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

Oil-insoluble metal thiolates prepared by reacting an acyloin, phosphorus pentasulfide and a heavy metal salt are rendered oil soluble when combined with alkenyl or alkyl mono- or bis-succinimides. The complexes are effective as anti-oxidants and anti-wear inhibitors in lubricating oils.

## Claims

### Claim 1

A process for preparing an oil-soluble metal thiolate-succinimide complex which comprises reacting (a) an alkyl or alkenyl mono- or bis-succinimide with (b) an oil-insoluble metal thiolate prepared by reacting
(1) an acyloin of the formula: ##STR11## wherein R.sup.1 and R.sup.2 are the same or different and each is H, alkyl containing 1 to 30 carbon atoms, aryl containing 6 to 10 carbon atoms, alkaryl containing 7 to 30 carbon atoms, aralkyl containing 7 to 30 carbon atoms, or together R.sup.1 and R.sup.2 are alkylene and form a cyclic ring containing 4 to 6 carbon atoms which includes the carbon atoms to which they are attached, with phosphorus pentasulfide in an inert solvent at a temperature of from 25.degree. C. to 180.degree. C.;
wherein the mole ratio of acyloin to phosphorus pentasulfide is at least 1 to 2; and
(2) reacting the product from (1) with a reactive water-soluble, ionizable compound of a heavy metal in an aqueous solution whereby the final product (b) has a thiolato ligend of the formula: ##STR12## to metal ratio of from 0.5:1 to 1.5:1, and wherein the weight ratio of (a) to (b) is in the range of from 2:1 to 10:1.

### Claim 2 (depends on 1)

The process of claim 1 wherein in component (a) the succinimide has the formula: ##STR13## wherein X is ##STR14## where R is hydrogen or alkyl of 1 to 5 carbon atoms or a group of the formula: ##STR15## wherein R.sup.3 is an alkyl or alkenyl group containing from about 20 to 300 carbon atoms; U is alkylene containing 1 to 8 carbon atoms; n is an integer of from 1 to 9; and
in component (b) the acyloin has the formula: ##STR16## wherein R.sup.1 and R.sup.2 are the same or different and each is H, alkyl containing 1 to 30 carbon atoms, aryl containing 6 to 10 carbon atoms, alkaryl containing 7 to 30 carbon atoms, aralkyl containing 7 to 30 carbon atoms, or together R.sup.1 and R.sup.2 are alkylene and form a cyclic ring containing 4 to 6 carbon atoms which includes the carbon atoms to which they are attached; and the metal is selected from the group consisting of Co, Cr, Cu, W, Ni, Fe, V, Ti and Mo;
wherein the weight ratio of (a) to (b) is in the range of from 2:1 to 10:1.

### Claim 3 (depends on 2)

The process of claim 2 wherein in component (a) the succinimide has the formula: ##STR17## wherein U is ethylene; R is hydrogen; n is an integer of from 1 to 4; X is NH.sub.2 or a group of the formula: ##STR18## wherein R.sup.3 is polyisobutylene; and in component (b) the metal is molybdenum and the acyloin has the formula: ##STR19## wherein R.sup.1 and R.sup.2 are the same or different and each is hydrogen, alkyl containing 1 to 30 carbon atoms or phenyl.

### Claim 4 (depends on 3)

The process of claim 3 wherein in component (a), R.sup.3 is polyisobutenyl; U is ethylene; X is NH.sub.2 ; and n is 3 or 4; and in component (b), R.sup.1 and R.sup.2 are hydrogen, methyl or phenyl.

### Claim 5 (depends on 1, 2, 3)

A lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor proportion sufficient to inhibit oxidation and corrosion, of an oil-soluble metal thiolate-succinimide complex prepared according to the process of any one of claims 1, 2, 3, or 4.

### Claim 6 (depends on 1)

A lubricating oil concentrate comprising 10% to 90% by weight of a lubricating oil and from about 90% to 10% by weight of an oil-soluble metal thiolate-succinimide complex prepared according to claim 1.

### Claim 7 (depends on 1, 2, 3)

A composition comprising the complex prepared according to the process of any one of claims 1, 2, 3, or 4.