EP0032281B1 - Verfahren zur Herstellung von Hochdruck-Zusätzen für Schmieröl - Google Patents

Verfahren zur Herstellung von Hochdruck-Zusätzen für Schmieröl Download PDF

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Publication number
EP0032281B1
EP0032281B1 EP80300128A EP80300128A EP0032281B1 EP 0032281 B1 EP0032281 B1 EP 0032281B1 EP 80300128 A EP80300128 A EP 80300128A EP 80300128 A EP80300128 A EP 80300128A EP 0032281 B1 EP0032281 B1 EP 0032281B1
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EP
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Prior art keywords
sulfur
sodium sulfide
olefin
gram
reaction
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Expired
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EP80300128A
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English (en)
French (fr)
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EP0032281A1 (de
Inventor
Andrew George Papay
Joseph Peter O'brien
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Edwin Cooper Inc
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Edwin Cooper Inc
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Priority to EP80300128A priority Critical patent/EP0032281B1/de
Priority to DE8080300128T priority patent/DE3067302D1/de
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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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
    • 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • 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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/22—Acids obtained from 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • 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
    • 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
    • C10M2219/024—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats
    • 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
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • 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
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
    • 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
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • 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
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
    • 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
    • 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
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12

Definitions

  • Sulfurized olefins are well-known additives in lubricating oil, cutting oil and the like.
  • U.S. Patent Specification No. 2,249,312 describes such a product.
  • U.S. Patent Specification No. 2,708,199 describes a similar product in which a sulfur halide is reacted with an olefin using a lower alkanol promoter to obtain an intermediate which is reacted with an alkali or alkaline earth metal polysulfide.
  • 3,471,404 describes a product in which sulfur monochloride is reacted with olefin to obtain an intermediate which is reacted with sulfur and alkali metal sulfide at a critical ratio of 1.8 to 2.2 gram moles of metal sulfide per gram mole of sulfur. This material is then typically refluxed for 1 to 24 hours with aqueous alkali metal hydroxide (in general terms, "reacted with an inorganic base").
  • GB-A-1308894 describes a method of sulfohalogenating olefins with a sulfurhalide in the presence of a catalytic quantity of a lower aliphatic alcohol to form a sulfohalogenated organic intermediate and thereafter sulfurising and dehalogenating the intermediate by treatment with an aqueous alkali metal monosulfide solution.
  • an improved sulfurized olefin additive for lubricating oil may be obtained by reacting sulfur monochloride with C a -C 6 aliphatic monoolefin to form an adduct which is then reacted with sulfur and sodium sulfide, using from 0.1 to 0.4 gram atom sulfur per gram mole of sodium sulfide, and then recovered by conventional methods without the need for further treatment with aqueous inorganic base (caustic).
  • the invention provides a process for preparing a sulfurized lubricating oil additive for imparting extreme pressure properties to lubricating oil which process comprises (a) reacting sulfur monochloride with a C 3 -C 6 aliphatic monoolefin to produce an adduct, (b) reacting the adduct produced in (a) with sulfur and sodium sulfide in an aqueous alkanol medium using from 0.1 to 0.4 gram atom of sulfur per gram mole of sodium sulfide, and (c) recovering the additive resulting from (b) without heating with aqueous caustic.
  • a preferred embodiment of this invention is the process consisting essentially of (a) reacting S Z CI 2 with a C a-6 aliphatic monoolefin at 30 to 100°C. to produce an adduct, (b) reacting said adduct with sulfur and Na Z S in an aqueous alkanol medium at a temperature of from 50°C up to reflux using 0.1 to ' . 0.4 gram atom of sulfur per gram mole of Na 2 S and then (c) recovering said additive without "treatment with an inorganic base".
  • Useful olefins are the monoethylenically unsaturated aliphatic hydrocarbons referred to as aliphatic monoolefins containing 3 to 6 carbon atoms. These include 1-butene, 2-butene, isobutene, 1-pentene, 2-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, 1-hexene, 2-hexene, 3-hexene, 2-methyl-1-pentene, 2-methyl-2-pentene, 2-ethyl-2-butene and the like, including mixtures thereof.
  • the olefins are branched-chain olefins such as isobutene, 2-methyl-1-butene, 2-methyl-2-butene, 2-methyl-2-pentene and the like. More preferably the ethylenic double bond adjoins a tertiary carbon atom such as isobutylene, the most preferred olefin.
  • the first stage reaction is preferably conducted by adding the olefin to the sulfur monochloride.
  • the olefin can be added as a gas or liquid. Preferably it is added beneath the surface of the sulfur monochloride as a liquid.
  • olefin is added until the reaction with the sulfur monochloride stops as indicated by loss of exotherm.
  • An amount of from 0.75 to 2.0 gram moles of olefin for each 0.3 to 0.75 gram mole of sulfur monochloride usually suffices.
  • a preferred amount is 1.8 to 2.2 gram moles of olefin per gram mole of sulfur monochloride.
  • the lower alkanol promoter used in the first stage contains from 1 to 4 carbon atoms such as methanol, ethanol, n-propanol, isopropanol, isobutanol, tert-butanol and the like.
  • the most preferred promoter is methanol.
  • the lower alkanol promoter can be added to the sulfur monochloride initially, added to the reaction mixture continuously or periodically during the course of the olefin addition or the alkanol can be mixed with the olefin and added together with the olefin.
  • the preferred modes of addition are to either add the entire amount initially and then add the olefin or to concurrently add both alkanol and olefin.
  • the amount of alkanol promoter is preferably of from 0.001 to 0.3 gram moles for each 0.3 to 0.75 gram mole of sulfur monochloride.
  • the first stage reaction can be conducted at any temperature high enough to cause the reaction to proceed, but not so high as to cause decomposition of the reactants or products.
  • a useful range is 30 to 100°C.
  • a more preferred range is 40 to 75°C and a most preferred range is 50 to 60°C.
  • the first stage reaction should be conducted for a time sufficient to complete the reaction between sulfur monochloride and olefin. This is usually limited by heat removal. Olefin feed rate is preferably controlled to hold the temperature within the desired range. When the sulfur monochloride has been consumed the temperature will drop. External heat may be added to continue the reaction for a further time, but this does not appear to be necessary.
  • the overall time required to complete the reaction depends upon the scale of the process and can vary from a few minutes up to 12 or more hours. The time is not critical.
  • HCI gas is evolved so means should be provided to scrub the vent gas from the reactor to remove HCI prior to releasing it to the atmosphere.
  • adduct from the first stage is reacted with sodium sulfide and sulfur in an aqueous alkanol reaction medium.
  • the second stage is preferably carried out by charging aqueous sodium sulfide, water, alkanol and elemental sulfur flowers to a reactor and then adding the adduct to this at reaction temperature.
  • the sodium sulfide may be obtained from any of a number of sources. For example, it can be made by mixing approximately equal mole amounts of sodium hydrosulfide and sodium hydroxide. If hydrogen sulfide is available, it can be adsorbed in aqueous NaOH to form a solution of sodium sulfide and/or sodium hydrosulfide depending upon the amount of hydrogen sulfide adsorbed. Whatever the source, the resulting solution should be adjusted with either NaOH, NaSH or H 2 S so that the resulting solution consists mainly of sodium sulfide with little or no free sodium hydroxide.
  • the amount of sodium sulfide can vary somewhat. For example, from 0.45 to 0.7 gram mole for each 0.3 to 0.75 gram mole of sulfur monochloride used in the first reaction stage.
  • the amount of sodium sulfide is 0.7 to 2 gram mole per mole of sulfur monochloride and most preferably 0.8 to 1 gram mole per gram mole of sulfur monochloride. What is essential is that from 0.1 to 0.4 gram atom sulfur be used per gram mole of sodium sulfide.
  • the amount of water can vary widely without detrimental effect. Good results can be obtained using 10 to 20 gram moles of water per gram mole of sodium sulfide. This includes water added as such, water in aqueous reactants and water which might be formed by reaction of hydrogen sulfide or sodium hydrosulfide with sodium hydroxide in forming sodium sulfide solution.
  • Alcohol is required in the second stage reaction.
  • these are lower alkanols containing 1 to 4 carbon atoms such as methanol, ethanol, n-propanol, n-butanol, isobutanol, tert-butanol and the like, including mixtures thereof.
  • the preferred alkanol is isopropanol either alone or mixed with other alkanols such as tert-butanol.
  • the amount of alkanol can likewise vary over a wide range.
  • a useful range is 0.1 to 0.5 parts by weight per each part by weight of water.
  • a more preferred range is 0.2 to 0.4 parts by weight alkanol per each part by weight water.
  • Preferred amounts of sulfur and sodium sulfide in the second reaction are 0.05 to 0.18 gram atom of sulfur and 0.45 to 0.7 gram mole of sodium sulfide. It is also preferred that 0.1 to 0.25 gram atom of sulfur be used per gram mole of sodium sulfide.
  • the mixture of sodium sulfide, sulfur and aqueous alkanol is stirred and heated to reaction temperature and then the adduct is added to it.
  • the reaction can be carried out in other ways such as by adding the sodium sulfide, sulfur and aqueous alkanol mixture to the adduct or by mixing everything together and heating the mixture.
  • the preferred second stage reaction temperature is 50°C. up to reflux temperature. A more preferred reaction temperature is 60 to 80°C.
  • the preferred second stage reaction temperature is 50°C. up to reflux temperature. A more preferred reaction temperature is 60 to 80°C.
  • the mixture is preferably heated to reflux for 2 to 8 hours to assure completion of the reaction.
  • an additive made according to the foregoing disclosure needs no further caustic treatment in order to obtain a useful EP additive. Accordingly, the present invention does not contemplate a process in which the product is subsequently heated with aqueous inorganic base (caustic) solution such as is disclosed in U.S. Patent Specification No. 3,471,404.
  • aqueous inorganic base (caustic) solution such as is disclosed in U.S. Patent Specification No. 3,471,404.
  • the product may be recovered by conventional methods such as removing alkanol, water washing and filtering.
  • the sulfurized olefin additive made by the present invention are especially useful in lubricating oil formulations used in gear applications.
  • the base oil may be a mineral oil or a synthetic oil.
  • Useful synthetic oils include olefine oligomers such as decene trimer, tetramer and pentamer made by oligomerizing 1-decene using a BF 3 catalyst.
  • Useful olefin oligomers can be made using other catalysts such as the aluminum alkyl Ziegler catalyst.
  • other olefins can be used such as C, -14 1-otefins.
  • Synthetic alkylbenzenes can also be used such as di-dodecylbenzene and the like.
  • Synthetic ester lubricating oil can also be employed such as the alkyl esters of dicarboxylic acid (e.g., di-2-ethyl-hexylsebacate), fatty acid esters of polyols (e.g., trimethylolpropane, tripelargonate) or complex esters of alkanols, alkane, polyols and carboxylic or polycarboxylic acid.
  • dicarboxylic acid e.g., di-2-ethyl-hexylsebacate
  • fatty acid esters of polyols e.g., trimethylolpropane, tripelargonate
  • complex esters of alkanols, alkane, polyols and carboxylic or polycarboxylic acid e.g., trimethylolpropane, tripelargonate
  • sulfurized olefin is added to an amount sufficient to improve the EP property of the lubricant.
  • An amount of 0.1 to 10.0 weight percent is usually sufficient.
  • Fully formulated gear lubricants include other conventional additives which perform various functions.
  • other additives are corrosion inhibitors for ferrous and non-ferrous metals such as tetrapropenyl succinic acid and bis-(2,5-alkyldithia)-1,3,4-triadiazoles, and antiwear additives such as alkyl or aryl phosphonates, phosphite, thiophosphates, dithiophosphates, and phosphoric acids.
  • antiwear additives such as alkyl or aryl phosphonates, phosphite, thiophosphates, dithiophosphates, and phosphoric acids.
  • zinc dialkyl or diaryl diethiophosphate chlorinated hydrocarbons, sulfurized fatty esters and amines.
  • the tests were conducted in SAE 90 mineral oil. The first was a 4-ball weld test (ASTM D2783) in which a steel ball is rotated in loaded contact with three fixed balls. The maximum load without weld is recorded as the pass load.

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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)

Claims (6)

1. Verfahren zur Herstellung eines sulfurierten Schmieröl-Zusatzes, um Schmieröl extreme Druckeigenschaften zu verleihen, welches (a) eine Umsetzung von Schwefelmonochlorid mit einem C3-C6-aliphatischen Monoolefin zur Herstellung eines Adduktes, (b) Umsetzung des in (a) hergestellten Adduktes mit Schwefel und Natriumsulfid in einem wäßrigen Alkalol-Medium unter Verwendung von 0,1 bis 0,4 Gramm-Atom Schwefel pro Gramm-Mol Natriumsulfid, und (c) Gewinnung des Zusatzes, der sich aus (b) ergibt, ohne Erhitzung mit wäßrigem Alkali, umfaßt.
2. Verfahren nach Anspruch 1, worin das Monoolefin mit Schwefelmonochlorid bei einer Temperatur im Bereich von 30 bis 100°C in (a) umgesetzt wird, wobei die Reaktion von (b) bei einer Temperatur von 50°C bis zur Rückflußtemperatur bewirkt wird.
3. Verfahren nach Anspruch 2, worin das Monoolefin ein verzweigtkettiges Monoolefin ist.
4. Verfahren nach Anspruch 3, worin das Olefin Isobuten ist.
5. Verfahren nach einem der Ansprüche 2 bis 4, worin das Verhältnis von Schwefel zu Natriumsulfid in (b) von 0,1 bis 0,25 Gramm-Atom Schwefel pro Gramm-Mol Natriumsulfid beträgt.
6. Verfahren nach einem der Ansprüche 2 bis 5, worin 0,75 bis 2 Gramm-Mol des Olefins mit 0,3 bis 0,75 Gramm-Mol Schwelfelmonochlorid in (a) umgesetzt werden und das erhaltene Addukt mit 0,45 bis 0,7 Gramm-Mol Natriumsulfid und 0,05 bis 0,18 Gramm-Atom Schwefel in (b) umgesetzt wird.
EP80300128A 1980-01-15 1980-01-15 Verfahren zur Herstellung von Hochdruck-Zusätzen für Schmieröl Expired EP0032281B1 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP80300128A EP0032281B1 (de) 1980-01-15 1980-01-15 Verfahren zur Herstellung von Hochdruck-Zusätzen für Schmieröl
DE8080300128T DE3067302D1 (en) 1980-01-15 1980-01-15 A process for making an extreme pressure lubricating oil additive

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Application Number Priority Date Filing Date Title
EP80300128A EP0032281B1 (de) 1980-01-15 1980-01-15 Verfahren zur Herstellung von Hochdruck-Zusätzen für Schmieröl

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EP0032281A1 EP0032281A1 (de) 1981-07-22
EP0032281B1 true EP0032281B1 (de) 1984-04-04

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3560285D1 (en) * 1984-04-20 1987-07-30 Inst Francais Du Petrole Process for the preparation of polysulfurised olefins, products so obtained and their use as additives for lubricants
FR2571380B2 (fr) * 1984-10-10 1987-01-09 Inst Francais Du Petrole Procede de preparation d'olefines polysulfurees, les produits obtenus et leur utilisation comme additifs pour lubrifiants
FR2588881B1 (fr) * 1985-10-18 1988-01-15 Inst Francais Du Petrole Compositions d'olefines polysulfurees, leur preparation et leur utilisation comme additifs pour lubrifiants
GB8826961D0 (en) * 1988-11-18 1988-12-21 Castrol Ltd Lubricant compositions
CN103923062B (zh) * 2014-03-25 2016-02-10 定远县云森科技有限公司 高压硫化异丁烯的精处理工艺

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DE3067302D1 (en) 1984-05-10

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