EP0271368B1 - Compositions d'oléfines polysulfurées, leur préparation et leur utilisation comme additifs pour lubrifiants - Google Patents

Compositions d'oléfines polysulfurées, leur préparation et leur utilisation comme additifs pour lubrifiants Download PDF

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Publication number
EP0271368B1
EP0271368B1 EP87402252A EP87402252A EP0271368B1 EP 0271368 B1 EP0271368 B1 EP 0271368B1 EP 87402252 A EP87402252 A EP 87402252A EP 87402252 A EP87402252 A EP 87402252A EP 0271368 B1 EP0271368 B1 EP 0271368B1
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Prior art keywords
composition according
polysulfide
aliphatic
proportion
radical
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German (de)
English (en)
French (fr)
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EP0271368A1 (fr
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Maurice Born
Lucienne Briquet
Jacques Lallement
Guy Parc
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IFP Energies nouvelles
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/02—Sulfurised compounds
    • C10M135/04—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/02—Bearings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/241—Manufacturing joint-less pipes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/242—Hot working
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/243—Cold working
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/245—Soft metals, e.g. aluminum
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/246—Iron or steel
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/247—Stainless steel

Definitions

  • the invention relates to the field of organic sulfur additives used in particular to improve the extreme pressure properties of lubricants; it relates more particularly to new products of the polysulphurized olefin type, their preparation and their use as additives for mineral or synthetic lubricants.
  • JI is indicated in the single example that the product has a sulfur content of 49% by mass and a viscosity at 37.8 ° C (100 ° F) of 8.6 mm 2 / s (cSt).
  • the products thus prepared are polysulphurized olefins, which can have a sulfur content generally ranging up to approximately 45-65% by mass. Their kinematic viscosity at 100 ° C varies according to their sulfur content. It can be around 4 to 20 mm 2 / s. Their halogen content (mainly chlorine) is generally less than about 1% by mass and more often than about 0.6% by mass.
  • PAO hydrogenated polyalphaolefins
  • United States patent US-A-3 873 454 describes an extreme pressure additive for lubricants obtained by reaction of isobutylene and a sulfur halide to form an "adduct", followed by the reaction of said "adduct" with an alkaline mercaptate, in an inert medium to form the compound of formula:
  • the alkaline mercaptate used can be sodium, potassium, lithium or calcium mercaptate.
  • the reaction medium is generally a lower alcohol (C 1 to C 4 ).
  • the desired compound (which has a sulfur content of about 53%) is obtained with a yield of about 45% by weight, the remaining 55% consisting of a mixture of sulfides and unsaturated polysulfides.
  • the desired compound is finally obtained in the form of a solid, which is separated and purified.
  • the monoolefin is used more particularly in an amount of 1.5 to 2.5 moles per mole of mono- and / or sulfur dichloride. It is generally introduced into the liquid mono- and / or dichloride at 20-80 ° C, more specifically at 30-50 ° C.
  • the adduct, or "adduct”, obtained at the end of step (1) consists of a mixture of sulfur compounds in which the average proportion of sulfur can be approximately 1 to 2 gram atoms per mole , depending on whether sulfur dichloride, sulfur monochloride or a mixture of the two is used at the start.
  • the proportion of chlorine is approximately 2 gram atoms per mole of product.
  • the mercaptate polysulphides of general formula R 3- S x M used in step (2) can be more particularly prepared by reaction, preferably in alcoholic medium, of at least one mercaptan of general formula R 3 SH with a mineral base MOH, R 3 and M being defined as above, then with elemental sulfur in a suitable proportion so that the average value of x in the formula of the product obtained is approximately 1.2 to 7.
  • mercaptans of formula R 3 SH which can advantageously be used to prepare mercaptate-polysulphides
  • the reaction between the mercaptan and the mineral base is generally carried out at a temperature of 20 to 100 ° C.
  • the alcoholic medium can comprise at least one aliphatic monoalcohol containing, for example, from 1 to 5 carbon atoms. Most often methanol is used. In general, 200 to 400 ml of aliphatic monoalcohol are used per mole of mercaptan involved.
  • the product obtained is a sodium mercaptate, potassium or ammonium of formula R 3- SM (M representing Na, K or NH 4 ).
  • the mercaptate thus formed is reacted with elemental sulfur, brought into play in a proportion ranging for example from about 0.2 to 10 gram atoms per mole of mercaptate. This reaction can be carried out at a temperature of 20-100 ° C.
  • step (2) where the mercaptate-polysulfide of formula R 3 S X M is reacted, preferably in an alcoholic medium, with "adduct" obtained at the end of step (1 ), said "adduct” is generally added to the alcoholic solution of said mercaptate-polysulfide in a proportion such that said mercaptate-polysulfide represents a molar excess of about 0.1 to 70% relative to the stoichiometry of 2 moles per mole of said "adduct", the reaction medium being maintained for example at a temperature ranging from -10 ° C. to the reflux temperature of the alcoholic solvent involved.
  • a polysulphurized olefin composition is obtained which can then be treated, in a step (3), with an alkaline aqueous solution, more particularly an aqueous solution of soda or potassium hydroxide having example a concentration of about 1 to 50% by mass.
  • an alkaline aqueous solution more particularly an aqueous solution of soda or potassium hydroxide having example a concentration of about 1 to 50% by mass.
  • the amount of alkaline solution used can for example be from 0.1 to 5 times the mass amount of crude polysulphurized olefin to be treated.
  • the polysulfurized olefin compositions of the invention may have a sulfur content of about 25 to 60% by mass; their chlorine content is generally less than 0.1% by mass, most often less than 0.05% by mass. They can advantageously be used as extreme pressure additives for lubricating oils.
  • a first application of the polysulfurized olefin compositions of the invention relates more particularly to the formulation of oils intended for the lubrication of gears.
  • the base oils can be of mineral or synthetic origin.
  • Synthetic oils include in particular oligomers of olefins such as triene, tetra- and pentamer of decene-1 obtained by oligomerization in the presence of LEWIS acids.
  • Other ⁇ -olefins can of course be used, for example Ce to C 14 ⁇ -olefins.
  • alkylbenzenes such as mono and dialkylbenzenes, or alternatively synthetic esters originating from mono- or polycarboxylic acids (such as sebacic acid, fatty acids, etc.) and monoalcohols or polyols, (such as 2-ethyl hexanol, trimethylol-propane, etc.).
  • mono- or polycarboxylic acids such as sebacic acid, fatty acids, etc.
  • monoalcohols or polyols such as 2-ethyl hexanol, trimethylol-propane, etc.
  • the polysulphurized olefins considered can then be added to the lubricating oils at concentrations ranging for example from 0.5 to 10% by mass.
  • additives can be used in combination with phosphorus additives, such as metallic dialkyl- or diaryldithiophosphates, phosphites and organic phosphates.
  • antioxidants such as antioxidants, anti-rust agents, copper passivators, anti-foam agents, friction reducers, in the usual proportions.
  • a second application of the polysulphurized olefin compositions of the invention as extreme pressure additives for lubricants relates more particularly to the formulation of oils intended for working with metals (cutting, forming, etc.).
  • the concentration of additive used is generally from 0.1 to 20% and preferably from 0.5 to 5% by mass relative to the lubricating oil.
  • other conventional additives can be added, such as chlorinated paraffins in a proportion corresponding for example to 2-10% by mass of chlorine relative to the lubricating oil.
  • Example 4 is given for comparison.
  • Example 1 The experiment of Example 1 is repeated under the same operating conditions, but this time 76.8 g of sulfur in flower (2.4 gram atoms) is used; the S / mercaptan molar ratio used is then 1/1.
  • Example 1 The experiment of Example 1 was repeated once again, but this time no elemental sulfur was used.
  • Tests have been carried out demonstrating the extreme pressure properties of additives prepared according to some of the preceding examples on the one hand in formulations of the gear oil type and, on the other hand, in formulations of the working oil type metals.
  • Example 3 The extreme pressure properties of the additive obtained in Example 3 are evaluated from a formulation of the metal cutting oil type, using a 4-ball machine according to the ASTM D 2783 procedure.
  • the lubricant formulation used consists of a 100 Neutral Solvent oil containing 3% of chlorine in the form of chlorinated paraffin, and 1% of sulfur in the form of sulfur additive of Example 2; the results obtained are collated in table 2 below.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP87402252A 1986-10-17 1987-10-09 Compositions d'oléfines polysulfurées, leur préparation et leur utilisation comme additifs pour lubrifiants Expired - Lifetime EP0271368B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8614576 1986-10-17
FR8614576A FR2605328B1 (fr) 1986-10-17 1986-10-17 Compositions d'olefines polysulfurees, leur preparation et leur utilisation comme additifs pour lubrifiants.

Publications (2)

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EP0271368A1 EP0271368A1 (fr) 1988-06-15
EP0271368B1 true EP0271368B1 (fr) 1990-05-23

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EP87402252A Expired - Lifetime EP0271368B1 (fr) 1986-10-17 1987-10-09 Compositions d'oléfines polysulfurées, leur préparation et leur utilisation comme additifs pour lubrifiants

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US (1) US4839069A (esLanguage)
EP (1) EP0271368B1 (esLanguage)
JP (1) JP2619654B2 (esLanguage)
CN (1) CN87107001A (esLanguage)
AU (1) AU600983B2 (esLanguage)
BR (1) BR8705541A (esLanguage)
CA (1) CA1299173C (esLanguage)
DE (1) DE3762879D1 (esLanguage)
ES (1) ES2016642B3 (esLanguage)
FR (1) FR2605328B1 (esLanguage)
IN (1) IN168668B (esLanguage)
MX (1) MX172211B (esLanguage)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4730034A (en) * 1987-01-23 1988-03-08 Phillips Petroleum Company Recovering poly(arylene sulfide) oligomers from a poly(arylene sulfide) reaction mixture
DE3861262D1 (de) * 1987-05-27 1991-01-24 Inst Francais Du Petrole Verfahren zur herstellung von polysulfurierten olefin-zusammensetzungen mit hohem schwefel-und sehr niedrigem chlorgehalt.
FR2624133B1 (fr) * 1987-12-02 1990-09-14 Inst Francais Du Petrole Compositions d'olefines polysulfurees, leur preparation et leur utilisation comme additifs pour lubrifiants
FR2627105B3 (fr) * 1988-02-16 1990-06-08 Inst Francais Du Petrole Procede de presulfuration de catalyseur de traitement d'hydrocarbures
US5116523A (en) * 1988-06-23 1992-05-26 Mobil Oil Corporation Sulfide adducts of high viscosity index polyalphaolefins
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AU7986887A (en) 1988-04-21
JP2619654B2 (ja) 1997-06-11
DE3762879D1 (de) 1990-06-28
FR2605328A1 (fr) 1988-04-22
CN87107001A (zh) 1988-04-27
ES2016642B3 (es) 1990-11-16
MX172211B (es) 1993-12-07
EP0271368A1 (fr) 1988-06-15
JPS63110289A (ja) 1988-05-14
CA1299173C (fr) 1992-04-21
US4839069A (en) 1989-06-13
FR2605328B1 (fr) 1989-08-04
IN168668B (esLanguage) 1991-05-18
AU600983B2 (en) 1990-08-30
BR8705541A (pt) 1988-05-24

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