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US20020010102A1 - Sulfur-containing organophosphorus compounds - Google Patents

Sulfur-containing organophosphorus compounds Download PDF

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Publication number
US20020010102A1
US20020010102A1 US09/508,535 US50853500A US2002010102A1 US 20020010102 A1 US20020010102 A1 US 20020010102A1 US 50853500 A US50853500 A US 50853500A US 2002010102 A1 US2002010102 A1 US 2002010102A1
Authority
US
United States
Prior art keywords
sulfur
integer
compounds
containing organophosphorus
general formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US09/508,535
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English (en)
Inventor
Hiroaki Koshima
Hitoshi Hata
Noboru Sonoda
Izumi Terada
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Idemitsu Kosan Co Ltd
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of US20020010102A1 publication Critical patent/US20020010102A1/en
Assigned to IDEMITSU KOSAN CO., LTD reassignment IDEMITSU KOSAN CO., LTD ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HATA, HITOSHI, KOSHIMA, HIROAKI, SONODA, NOBORU, TERADA, IZUMI
Abandoned legal-status Critical Current

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Classifications

    • 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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
    • C10M137/105—Thio derivatives not containing metal
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/141—Esters of phosphorous acids
    • C07F9/1411—Esters of phosphorous acids with hydroxyalkyl compounds with further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4075—Esters with hydroxyalkyl 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
    • 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
    • C10M2223/047—Thioderivatives not containing metallic elements
    • 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

Definitions

  • the present invention relates to novel sulfur-containing organophosphorus compounds and a method for producing them, to additives for lubricating oils that contain the sulfur-containing organophosphorus compound, and to lubricating oil compositions comprising the sulfur-containing organophosphorus compound.
  • the invention is to provide novel sulfur-containing organophosphorus compounds and a method for producing them, to provide additives for lubricating oils that contain the sulfur-containing organophosphorus compounds, and to provide lubricating oil compositions containing the additive and capable of satisfying the requirements of extreme-pressure lubricity, wear resistance and frictional characteristics even under severe conditions of high loads such as those imposed on automatic or continuously variable transmissions and the like.
  • the first aspect of the invention is to provide at least one sulfur-containing organophosphorus compound selected from compounds of a general formula (I):
  • R 1 represents a hydrocarbon group having from 6 to 20 carbon atoms
  • R 2 represents a divalent hydrocarbon group having from 1 to 6 carbon atoms
  • n indicates an integer of from 1 to 3
  • R 1 and R 2 have the same meanings as above; p indicates an integer of from 0 to 2, and q indicates an integer of 0 or 1, with the proviso that p and q cannot be 0 at the same time.
  • the second aspect of the invention is to provide a method for producing the sulfur-containing organophosphorus compounds of the first aspect as above, which comprises reacting an alkylthioalkyl alcohol of a general formula (III):
  • R 1 and R 2 have the same meanings as above, with phosphorus trichloride in the absence of a catalyst or in the presence of a base.
  • the third aspect of the invention is to provide additives for lubricating oils, which contain at least one sulfur-containing organophosphorus compound selected from compounds of a general formula (IV):
  • R 1 and R 2 have the same meanings as above;
  • X and Y each represent S (sulfur) or O (oxygen), and either one of X and Y is S;
  • n has the same meaning as above,
  • m indicates an integer of from 0 to 4.
  • X, Y, R 1 , R 2 , p and q have the same meanings as above.
  • the fourth aspect of the invention is to provide lubricating oil compositions comprising an effective amount of the sulfur-containing organophosphorus compound as above.
  • FIG. 1 is the spectral pattern of the reaction product of Production Example 1 of the invention, appearing in phosphorus nuclear magnetic resonance spectrometry of the product; and FIG. 2 is the spectral pattern of the reaction product of Production Example 1, appearing in proton nuclear magnetic resonance spectrometry of the product
  • the first aspect of the invention is to provide at least one sulfur-containing organophosphorus compound selected from compounds of formulae (I) and (II) noted above.
  • R 1 represents a hydrocarbon group having from 6 to 20 carbon atoms, concretely including alkyl groups such as all types of hexyl groups, all types of heptyl groups, all types of octyl groups, all types of nonyl groups, all types of decyl groups, all types of undecyl groups, all types of dodecyl groups, all types of tridecyl groups, all types of tetradecyl groups, all types of pentadecyl groups, all types of hexadecyl groups, all types of heptadecyl groups, all types of octadecyl groups, all types of nonadecyl groups, all types of eicodecyl groups; cycloalkyl groups such as cyclohexyl group, all types of methylcyclohexyl groups, all types of ethylcyclohexyl groups, all types of alkyl groups such as all types of hexy
  • R 2 represents a divalent hydrocarbon group having from 1 to 6 carbon atoms, concretely including divalent aliphatic groups such as methylene group, ethylene group, 1,2-propylene group, 1,3-propylene group, all types of butylene groups, all types of pentylene groups, all types of hexylene groups; alicyclic groups with two bonding sites from alicyclic hydrocarbons such as cyclohexane, methylcyclopentane, etc.; all types of phenylene groups, etc. Of those, preferred are methylene group, ethylene group, and all types of propylene groups.
  • n indicates an integer of from 1 to 3, but is preferably 1 or 2.
  • p indicates an integer of from 0 to 2
  • q indicates an integer of 0 or 1, with the proviso that p and q cannot be 0 at the same time.
  • sulfur-containing organophosphorus compounds of formulae (I) and (II) include tri(octylthioethoxy) phosphite, tri(dodecylthioethoxy) phosphite, tri(hexadecylthioethoxy) phosphite, di(octylthioethoxy) phosphite, di(dodecylthioethoxy) phosphite, di(hexadecylthioethoxy) phosphite, mono(octylthioethoxy) phosphite, mono(dodecylthioethoxy) phosphite, mono(hexadecylthioethoxy) phosphite, octylthioethyl octylthioethylphosphonate, dodecylthioethy
  • the method for producing the sulfur-containing organophosphorus compounds of formulae (I) and (II) is not specifically defined.
  • the compounds may be produced by reacting an alkylthioalkyl alcohol of a general formula (III):
  • R 1 and R 2 have the same meanings as above, with phosphorus trichloride in the absence of a catalyst or in the presence of a base.
  • the amount of the alkylthioalkyl alcohol to be reacted with phosphorus trichloride may fall generally between 0.1 and 5.0 mols, preferably between 1.0 and 3.0 mols, more preferably between 1.5 and 2.5 mols, relative to one mol of phosphorus trichloride.
  • the reaction temperature may fall generally between ⁇ 10 and 100° C., preferably between 0 and 40° C.
  • the base serving as the catalyst includes, for example, triethylamine, pyridine, etc.
  • the reaction may be effected in a solvent such as THF, diethyl ether or the like.
  • the third aspect of the invention is to provide additives for lubricating oils, which contain at least one sulfur-containing organophosphorus compound selected from compounds of a general formula (IV):
  • R 1 and R 2 have the same meanings as above;
  • X and Y each represent S (sulfur) or O (oxygen), and either one of X and Y is S;
  • n has the same meaning as above,
  • m indicates an integer of from 0 to 4.
  • X, Y, R 1 , R 2 , p and q have the same meanings as above.
  • R 1 , R 2 , n, p and q are the same as those in the first aspect of the invention.
  • m is preferably an integer falling between 1 and 4.
  • the third aspect of the invention provides additives for lubricating oils, which contain at least one sulfur-containing organophosphorus compound selected from compounds of a general formula (VI):
  • R 1 , R 2 , Y, p and q have the same meanings as above.
  • the additives for lubricating oils contain at least one sulfur-containing organophosphorus compound selected from compounds of the following general formulae (VIII), (IX), (X), (XI) and (XII):
  • R 1 and R 2 have the same meanings as above.
  • sulfur-containing organophosphorus compounds are used as additives to lubricating oils, (1) they are used as they are, or (2) they are diluted with base oil of lubricating oils, before added to lubricating oils, or (3) they are combined with other additives, which will be mentioned hereinunder, into packages for use in lubricating oils. Therefore, the content of the sulfur-containing organophosphorus compound to be in the additives for lubricating oils may fall generally between 0.1 and 100% by weight.
  • the lubricating oils to which the additives of the third aspect of the invention are added are not specifically defined, including, for example, transmission oils for automatic or continuous variable transmissions, gear oils, engine oils for internal-combustion engines, bearing oils, shock absorber oils, cutting fluids, forming lubricants, rolling oils and other various lubricating oils for industrial use.
  • the fourth aspect of the invention is to provide lubricating oil compositions comprising base oil and an effective amount of at least one sulfur-containing organophosphorus compound as above.
  • the base oil usable is any of mineral oils and synthetic oils.
  • mineral oils include paraffinic mineral oils, naphthenic mineral oils, and mineral, intermediate base crude oils.
  • solvent-purified or hydrogenated light neutral oils, medium-gravity neutral oils, heavy neutral oils, bright stocks, etc.
  • Synthetic oils include, for example, poly- ⁇ -olefins, ⁇ -olefin copolymers, polybutenes, alkylbenzenes, polyolesters, esters of dibasic acids, esters of polyalcohols, polyoxyalkylene glycols, esters of polyoxyalkylene glycols, polyalkylene glycol ethers, cycloalkane compounds, etc.
  • base oils can be used either singly or as combined.
  • mineral oils and synthetic oils can be combined for use in the invention.
  • the effective amount of the sulfur-containing organophosphorus compound to be in the lubricating oil compositions varies, depending on the use of the compositions, but may fall generally between 0.01 and 10% by weight, preferably between 0.1 and 5% by weight of the composition.
  • the lubricating oil compositions of the invention may optionally contain any additional additives which have heretofore been used in ordinary lubricating oil compositions, such as detergent dispersants, antioxidants, rust inhibitors, defoaming agents, viscosity index improvers, pour point depressants, demulsifying agents, other extreme-pressure lubrication improvers, other anti-wear additives, etc., so far as the additional additives do not detract from the object of the invention.
  • additional additives which have heretofore been used in ordinary lubricating oil compositions, such as detergent dispersants, antioxidants, rust inhibitors, defoaming agents, viscosity index improvers, pour point depressants, demulsifying agents, other extreme-pressure lubrication improvers, other anti-wear additives, etc.
  • the lubricating oil compositions of the invention can be used, for example, as lubricating oils for power transmissions, lubricating oils for internal-combustion engines, gear oils, bearing oils, shock absorber oils, and lubricating oils for industrial machines.
  • reaction product was identified as a mixture of compounds of the following formula (XVI) and the above formula (XIII).
  • reaction product was identified as a mixture of compounds of the following formula (XVII) and the above formula (XIII).
  • the mixture was subjected to liquid chromatography (through a reversed-phase column with a solvent of acetonitrile, equipped with a differential refractiometer serving as a detector). The data confirmed that the mixture was comprised of 51% by weight of the compound of formula (XVII) and 49% by weight of the compound of formula (XIII).
  • Ring made of SAE 4620 steel.
  • Block made of SAE 01 steel.
  • the lubricating oil compositions that contain the sulfur-containing organophosphorus compound of the invention satisfy the requirements of extreme-pressure lubrication, wear resistance and frictional characteristics even under severe conditions of high loads such as those imposed on automatic or continuous variable transmissions and the like. Therefore, they have many applications in the field of lubricating oils.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
US09/508,535 1997-10-06 1998-10-05 Sulfur-containing organophosphorus compounds Abandoned US20020010102A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP9-272613 1997-10-06
JP27261397 1997-10-06

Publications (1)

Publication Number Publication Date
US20020010102A1 true US20020010102A1 (en) 2002-01-24

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US09/508,535 Abandoned US20020010102A1 (en) 1997-10-06 1998-10-05 Sulfur-containing organophosphorus compounds

Country Status (4)

Country Link
US (1) US20020010102A1 (fr)
EP (1) EP1022281A4 (fr)
CA (1) CA2294851A1 (fr)
WO (1) WO1999018112A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070105729A1 (en) * 2005-11-09 2007-05-10 Chip Hewette Gear additive composition
US20070142237A1 (en) * 2005-11-09 2007-06-21 Degonia David J Lubricant composition
US20070142249A1 (en) * 2005-11-09 2007-06-21 Degonia David J Composition comprising a sulfur-containing, phosphorus-containing compound, and/or its salt, and uses threof
US20070155632A1 (en) * 2004-03-29 2007-07-05 Idemitsu Kosan Co., Ltd. Lubricating oil composition for continuously variable transmission
US20080319216A1 (en) * 2005-11-09 2008-12-25 Degonia David J Salt of a Sulfur-Containing, Phosphorus-Containing Compound, And Methods Thereof
EP3556831A4 (fr) * 2016-12-14 2020-11-25 Idemitsu Kosan Co., Ltd. Composition d'huile lubrifiante, procédé de lubrification et engrenage
CN112912478A (zh) * 2018-11-06 2021-06-04 引能仕株式会社 润滑油组合物

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3322718A (en) * 1963-08-23 1967-05-30 Nat Distillers Chem Corp Polyolefins stabilized with phosphites, phenols, and benzotriazoles
US3294736A (en) * 1963-08-23 1966-12-27 Nat Distillers Chem Corp Polyolefins stabilized with bisphenols and organic phosphites containing mercapto groups
US3462375A (en) * 1966-10-20 1969-08-19 Nat Distillers Chem Corp Stabilizing composition for olefin polymers containing a hydrocarbon-mercapto-hydrocarbon phosphite,carbon black,and a hindered phenol
US3524909A (en) * 1966-12-27 1970-08-18 Nat Distillers Chem Corp Preparation of hydrocarbon thioalkylene phosphites
CH560227A5 (fr) * 1971-05-12 1975-03-27 Ciba Geigy Ag
JP3742438B2 (ja) * 1994-03-31 2006-02-01 東燃ゼネラル石油株式会社 自動変速機用潤滑油組成物
JP3512231B2 (ja) * 1994-05-10 2004-03-29 東燃ゼネラル石油株式会社 自動変速機用潤滑油組成物

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070155632A1 (en) * 2004-03-29 2007-07-05 Idemitsu Kosan Co., Ltd. Lubricating oil composition for continuously variable transmission
US20070105729A1 (en) * 2005-11-09 2007-05-10 Chip Hewette Gear additive composition
US20070142237A1 (en) * 2005-11-09 2007-06-21 Degonia David J Lubricant composition
US20070142249A1 (en) * 2005-11-09 2007-06-21 Degonia David J Composition comprising a sulfur-containing, phosphorus-containing compound, and/or its salt, and uses threof
US20080319216A1 (en) * 2005-11-09 2008-12-25 Degonia David J Salt of a Sulfur-Containing, Phosphorus-Containing Compound, And Methods Thereof
US7928260B2 (en) 2005-11-09 2011-04-19 Afton Chemical Corporation Salt of a sulfur-containing, phosphorus-containing compound, and methods thereof
US8299003B2 (en) 2005-11-09 2012-10-30 Afton Chemical Corporation Composition comprising a sulfur-containing, phosphorus-containing compound, and/or its salt, and uses thereof
EP3556831A4 (fr) * 2016-12-14 2020-11-25 Idemitsu Kosan Co., Ltd. Composition d'huile lubrifiante, procédé de lubrification et engrenage
CN112912478A (zh) * 2018-11-06 2021-06-04 引能仕株式会社 润滑油组合物
US11555159B2 (en) * 2018-11-06 2023-01-17 Eneos Corporation Lubricating oil composition
US12338408B2 (en) 2018-11-06 2025-06-24 Eneos Corporation Lubricating oil composition

Also Published As

Publication number Publication date
CA2294851A1 (fr) 1999-04-15
EP1022281A1 (fr) 2000-07-26
EP1022281A4 (fr) 2002-02-13
WO1999018112A1 (fr) 1999-04-15

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Owner name: IDEMITSU KOSAN CO., LTD, JAPAN

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:KOSHIMA, HIROAKI;HATA, HITOSHI;SONODA, NOBORU;AND OTHERS;REEL/FRAME:012673/0826

Effective date: 19991110

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION