US4645610A
Expired / Lapsed
US
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Method for the preparation of olefin polysulfides, the products obtained and their utilization as lubricant additives
Assignee: IFP Energies nouvelles
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Filing: 1985-04-19
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Granted: 1987-02-24
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Expires: 2005-04-19
Abstract
Abstract A method for the preparation of olefin polysulfides that can be used in particular as extreme pressure additives for lubricants is described. This method comprises: (1) reacting sulfur monochloride or dichloride with at least one mono-olefin containing 2 to 5 carbon atoms (in general isobutene) resulting in the formation of an adduct; (2) bringing into contact said adduct, conjointly with a hydrocarbyl halide, with a sulfur compound (for example, alkaline sulfides, hydrosulfides or polysulfides) and, in most cases, elemental sulfur, in an aqueous or aqueous-alcoholic medium; (3) heating the mixture and, after it has settled into two phases, separating the organic phase containing the olefin polysulfide; and if necessary (4) treating the product obtained with a base. The olefin polysulfides obtained contain a high proportion of sulfur, have a satisfactory viscosity and are sufficiently soluble in mineral oils as well as synthetic oils to be used as extreme pressure additives in the formulation of gear oils. Some of these products are also advantageous in the formulation of oils intended to be used in metal work.
Inventors
- 👤 Maurice Born
- 👤 Guy Parc
- 👤 Lucienne Briquet
- 👤 Daniel Paquer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 12:40
CPC Classifications
C; C10; C10M; C10M135/00; C10M135/02; C10M135/04; C07; C07G; C07G99/00; C07G99/002; C07G99/0022; C10M2203/00; C10M2203/06; C10M2205/00; C10M2205/02; C10M2205/028; C10M2207/00; C10M2207/28; C10M2207/281; C10M2207/282; C10M2207/283; C10M2207/286; C10M2207/34; C10M2219/00; C10M2219/02; C10M2219/022; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/042; C10M2223/045
Claims Analysis
Total Claims: 50
Claim 1
Independent Claim
223 words
A method for the preparation of an olefin polysulfide, comprising the following steps: (1) reacting at least one compound chosen from sulfur monochloride or dichloride with at least one mono-olefin containing 2 to 5 carbon atoms, in a proportion of 1.5 to 2.5 moles of mono-olefin per mole of sulfur monochloride and/or dichloride, thereby forming an addition compound or adduct; (2) contacting said addition compound or adduct with at least one hydrocarbyl halide chosen from C 1 to C 12 alkyl, C 5 to C 12 cycloalkyl C 6 to C 12 arylalkyl chlorides, bromides and iodides, the proportion of said hydrocarbyl halide corresponding to 1-70% in gram-atoms of halogen with respect to the number of gram-atoms of halogen in the aggregate formed by said adduct and said hydrocarbyl halide, and with at least one sulfur compound selected from the sulfides, hydrosulfides and polysulfides of alkali metals, ammonium or alkaline-earth metals used in a proportion of about 0.4 to 0.8 mole per gram-atom of halogen contained in the aggregate formed by said adduct and said hydrocarbyl halide, and a proportion of elemental sulfur of 0 to 7 gram-atoms per mole of said sulfur compound, in an aqueous medium; and (3) heating the resultant mixture, separating it into an aqueous phase and an organic phase and recovering resultant olefin polysulfide from the organic phase.
Claim 2
Independent Claim
223 words
A method for the preparation of an olefin polysulfide, comprising the following steps: (1) reacting at least one compound chosen from sulfur monochloride or dichloride with at least one mono-olefin containing 2 to 5 carbon atoms, in a proportion of 1.5 to 2.5 moles of mono-olefin per mole of sulfur monochloride and/or dichloride, thereby forming an addition compound or adduct; (2) contacting said addition compound or adduct with at least one hydrocarbyl halide chosen from C 1 to C 12 alkyl, C 5 to C 12 cycloalkyl C 6 to C 12 arylalkyl chlorides, bromides and iodides, the proportion of said hydrocarbyl halide corresponding to 1-70% in gram-atoms of halogen with respect to the number of gram-atoms of halogen in the aggregate formed by said adduct and said hydrocarbyl halide, and with at least one sulfur compound selected from the sulfides, hydrosulfides and polysulfides of alkali metals, ammonium or alkaline-earth metals used in a proportion of about 0.4 to 0.8 mole per gram-atom of halogen contained in the aggregate formed by said adduct and said hydrocarbyl halide, and a proportion of elemental sulfur of 0 to 7 gram-atoms per mole of said sulfur compound, in an aqueous medium; and (3) heating the resultant mixture, separating it into an aqueous phase and an organic phase and recovering resultant olefin polysulfide from the organic phase.
Claim 3
Dependent Claim
29 words
A method according to claim 1, wherein in step (1), isobutene or a mixture of isobutene with a minor proportion of diisobutene is used as as the aliphatic mono-olefin.
Claim 4
Dependent Claim
34 words
A method according to claim 1 wherein said hydrocarbyl halide is a chloride, bromide or iodide of a methyl, ethyl, isopropyl, n-propyl, tert-butyl, isobutyl, n-butyl, tert-amyl, isoamyl, n-amyl, n-hexyl, 2-ethylhexyl, n-octyl, cyclohexyl or benzyl.
Claim 5
Dependent Claim
34 words
A method according to claim 1, wherein said hydrocarbyl halide is comprised at least partly of a monohalogenated hydrocarbon compound containing at least one alcohol, phenol, carboxylic acid, amine, amide or thiol functional group.
Claim 6
Dependent Claim
19 words
A method according to claim 1, wherein said sulfur compound is sodium sulfide, sodium hydrosulfide or a sodium polysulfide.
Claim 7
Dependent Claim
22 words
A method according to claim 1, wherein the proportion of elemental sulfur is 0.4/1 to 7/1 gram-atoms per mole of sulfur compound.
Claim 8
Dependent Claim
93 words
A method according to claim 1, wherein in step (1), said monoolefin is reacted with said compound at a temperature of 20° to 80° C., for a time sufficient to form said adduct; in step (2) said adduct and said hydrocarbyl halide are added to a medium containing said sulfur compound at a maintained temperature of 20° to 100° C. for a period of 10 minutes to three hours; in step (3), the mixture is heated to a temperature in the 50° C. to the reflux temperature range, for 3 to 10 hours.
Claim 9
Dependent Claim
26 words
A method according to claim 1, further comprising a step (4) in which the organic phase separated in step (3) is treated with a basic compound.
Claim 10
Dependent Claim
35 words
A method according to claim 1, wherein, from step (2), the operations are effected continuously, the reagents used in step (2) being brought into contact in a parallel flow and according to a multiple-contact method.
Claim 11
Dependent Claim
44 words
A method according to claim 1, wherein the proportion of hydrocarbyl halide used in step (2) is 2 to 40% in gram-atoms of halogen with respect to the number of gram-atoms of halogen of the aggregate formed by said adduct and said hydrocarbyl halide.
Claim 12
Dependent Claim
26 words
A method according to claim 10, wherein the proportion of elemental sulfur used in step (2) is 0.4/1 to 3.3./1 gram-atoms per mole of sulfur compound.
Claim 13
Dependent Claim
46 words
A method according to claim 1, wherein the proportion of hydrocarbyl halide used in step (2) is about 40 to 70% of in gram-atoms of halogen with respect to the number of gram-atoms of halogen in the aggregate formed by said adduct and said hydrocarbyl halide.
Claim 14
Dependent Claim
26 words
A method according to claim 12, wherein the proportion of elemental sulfur used in step (2) is 3.3./1 to 7/1 gram-atoms per mole of sulfur compound.
Claim 15
Dependent Claim
11 words
An olefin polysulfide obtained by a method according to claim 1.
Claim 16
Dependent Claim
32 words
An olefin polysulfide according to claim 14, having a sulfur content ranging up to about 45-65% by weight and a kinematic viscosity at 100° C. of 4 to 20 mm 2 /s.
Claim 17
Dependent Claim
31 words
An olefin polysulfide according to claim 14, having sulfur content of about 60 to 65% by weight and a kinematic viscosity at 100° C. of 4 to 15 m 2 /s.
Claim 18
Dependent Claim
34 words
A lubricating composition comprising a major proportion of a mineral or synthetic lubricating oil and a minor proportion, sufficient to improve its extreme-pressure properties, of at least one olefin polysulfide according to claim 15.
Claim 19
Dependent Claim
32 words
A lubricating composition comprising a major proportion of a mineral lubricating oil and a minor proportion, sufficient to improve its extreme-pressure properties, of at least one olefin polysulfide according to claim 16.
Claim 20
Dependent Claim
11 words
An olefin polysulfide obtained by a process according to claim 3.
Claim 21
Dependent Claim
11 words
An olefin polysulfide obtained by a process according to claim 4.
Claim 22
Dependent Claim
11 words
An olefin polysulfide obtained by a process according to claim 5.
Claim 23
Dependent Claim
11 words
An olefin polysulfide obtained by a process according to claim 6.
Claim 24
Dependent Claim
11 words
An olefin polysulfide obtained by a process according to claim 7.
Claim 25
Dependent Claim
11 words
An olefin polysulfide obtained by a process according to claim 8.
Claim 26
Dependent Claim
11 words
An olefin polysulfide obtained by a process according to claim 9.
Claim 27
Dependent Claim
11 words
An olefin polysulfide obtained by a process according to claim 10.
Claim 28
Dependent Claim
11 words
An olefin polysulfide obtained by a process according to claim 11.
Claim 29
Dependent Claim
11 words
An olefin polysulfide obtained by a process according to claim 12.
Claim 30
Dependent Claim
11 words
An olefin polysulfide obtained by a process according to claim 13.
Claim 31
Dependent Claim
34 words
A lubricating composition comprising a major proportion of a mineral or synthetic lubricating oil and a minor proportion, sufficient to improve its extreme-pressure properties, of at least one olefin polysulfide according to claim 14.
Claim 32
Dependent Claim
34 words
A lubricating composition comprising a major proportion of a mineral or synthetic lubricating oil and a minor proportion, sufficient to improve its extreme-pressure properties, of at least one olefin polysulfide according to claim 19.
Claim 33
Dependent Claim
34 words
A lubricating composition comprising a major proportion of a mineral or synthetic lubricating oil and a minor proportion, sufficient to improve its extreme-pressure properties, of at least one olefin polysulfide according to claim 20.
Claim 34
Dependent Claim
34 words
A lubricating composition comprising a major proportion of a mineral or synthetic lubricating oil and a minor proportion, sufficient to improve its extreme-pressure properties, of at least one olefin polysulfide according to claim 21.
Claim 35
Dependent Claim
34 words
A lubricating composition comprising a major proportion of a mineral or synthetic lubricating oil and a minor proportion, sufficient to improve its extreme-pressure properties, of at least one olefin polysulfide according to claim 22.
Claim 36
Dependent Claim
34 words
A lubricating composition comprising a major proportion of a mineral or synthetic lubricating oil and a minor proportion, sufficient to improve its extreme-pressure properties, of at least one olefin polysulfide according to claim 23.
Claim 37
Dependent Claim
34 words
A lubricating composition comprising a major proportion of a mineral or synthetic lubricating oil and a minor proportion, sufficient to improve its extreme-pressure properties, of at least one olefin polysulfide according to claim 24.
Claim 38
Dependent Claim
34 words
A lubricating composition comprising a major proportion of a mineral or synthetic lubricating oil and a minor proportion, sufficient to improve its extreme-pressure properties, of at least one olefin polysulfide according to claim 25.
Claim 39
Dependent Claim
34 words
A lubricating composition comprising a major proportion of a mineral of synthetic lubricating oil and a minor proportion, sufficient to improve its extreme-pressure properties, of at least one olefin polysulfide according to claim 26.
Claim 40
Dependent Claim
34 words
A lubricating composition comprising a major proportion of a mineral or synthetic lubricating oil and a minor proportion, sufficient to improve its extreme-pressure properties, of at least one olefin polysulfide according to claim 27.
Claim 41
Dependent Claim
34 words
A lubricating composition comprising a major proportion of a mineral or synthetic lubricating oil and a minor proportion, sufficient to improve its extreme-pressure properties, of at least one olefin polysulfide according to claim 28.
Claim 42
Dependent Claim
32 words
A lubricating composition comprising a major proportion of a mineral lubricating oil and a minor proportion, sufficient to improve its extreme-pressure properties, of at least one olefin polysulfide according to claim 29.
Claim 43
Dependent Claim
28 words
A method according to claim 7, wherein in step (2) said adduct and said hydrocarbyl halide are added to a medium containing said sulfur compound and elemental sulfur.
Claim 44
Dependent Claim
11 words
An olefin polysulfide obtained by a process according to claim 42.
Claim 45
Dependent Claim
34 words
A lubricating composition comprising a major proportion of a mineral or synthetic lubricating oil and a minor proportion, sufficient to improve its extreme-pressure properties, of at least one olefin polysulfide according to claim 43.
Claim 46
Dependent Claim
25 words
A method according to claim 1, wherein the aqueous medium in step (2) consists essentially of a mixture of water and a lower aliphatic alcohol.
Claim 47
Dependent Claim
20 words
A method according to claim 45, wherein said lower aliphatic alcohol is methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol or tert-butanol.
Claim 48
Dependent Claim
25 words
A method according to claim 45, wherein said lower aliphatic alcohol is present in an amount of 2-60% by weight with respect to the water.
Claim 49
Dependent Claim
11 words
An olefin polysulfide obtained by a process according to claim 45.
Claim 50
Dependent Claim
34 words
A lubricating composition comprising a major proportion of a mineral or synthetic lubricating oil and a minor proportion, sufficient to improve its extreme-pressure properties, of at least one olefin polysulfide according to claim 48.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1990-02-23 | 1990-08-25 | 1991-02-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-02-23 | 1994-08-25 | 1995-02-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-02-23 | 1998-08-25 | 1999-02-24 | $7700.00 | Window Closed / Lapsed |