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WO2008113814A1 - Composés organiques du molybdène, leur utilisation comme modificateurs de frottement et compositions lubrifiantes - Google Patents

Composés organiques du molybdène, leur utilisation comme modificateurs de frottement et compositions lubrifiantes Download PDF

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Publication number
WO2008113814A1
WO2008113814A1 PCT/EP2008/053260 EP2008053260W WO2008113814A1 WO 2008113814 A1 WO2008113814 A1 WO 2008113814A1 EP 2008053260 W EP2008053260 W EP 2008053260W WO 2008113814 A1 WO2008113814 A1 WO 2008113814A1
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WO
WIPO (PCT)
Prior art keywords
molybdenum
friction
organic molybdenum
compounds
xanthate
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.)
Ceased
Application number
PCT/EP2008/053260
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English (en)
Inventor
Eiji Nagatomi
Noriaki Shinoda
Yoshihiko Aihara
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of WO2008113814A1 publication Critical patent/WO2008113814A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C333/14—Dithiocarbamic acids; Derivatives thereof
    • C07C333/16—Salts of dithiocarbamic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
    • C07C329/12—Dithiocarbonic acids; Derivatives thereof
    • C07C329/14—Esters of dithiocarbonic 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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M135/14—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
    • 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
    • C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M135/14—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
    • C10M135/18—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiocarbamic type, e.g. containing the groups
    • 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
    • C10M2207/2805—Esters used as base material
    • 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
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • 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
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066—Thiocarbamic type compounds
    • C10M2219/068—Thiocarbamate metal salts
    • 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
    • C10N2010/12—Groups 6 or 16
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure

Definitions

  • the invention provides novel organic molybdenum compounds, the use thereof as friction-modifiers, and lubricating compositions comprising said compounds.
  • Friction-modifiers (friction-adjusting agents) exist for adjusting the friction characteristics of a lubricant to an appropriate level. Friction-modifiers which reduce friction are used in lubricating compositions such as gear oils and engine oils with a view to reducing fuel costs. Friction-modifiers which raise friction are used for maintaining a certain high friction level in the lubricating compositions which are used in e.g. the wet-type clutch part of an automatic gear box. Many types of such friction-modifiers have been proposed.
  • organic molybdenum compounds are the most typical of these friction-modifiers and, as shown in "Shinban Sekiyu Seihin Tenkasai” (New Edition, Additives for Petroleum Products), by Toshio SAKURAI, Saiwai Shobo Co., published 25 th July, 1986, these organic molybdenum compounds are compounds which have two molybdenum atoms in one molecule as shown in formulae (2) and (3) below.
  • a first object of the present invention is to provide novel compounds which are useful as friction- modifiers for the optimal adjustment of friction and which do not contain phosphorus, and friction-modifiers comprising said compounds .
  • a second object of the present invention is to provide lubricating compositions in which these compounds are used. - -
  • -A is -OR or -NR' ; and each R is independently an alkyl group; and each R' is independently an alkyl group or two R' may, together with the N to which they are attached, form a five- membered or six-membered ring.
  • -A is -OR or -NR' ; and each R is independently an alkyl group; each R' is independently an alkyl group or two R' may, together with the N to which they are attached, form a five-membered or six- membered ring.
  • the invention provides the use of the organic molybdenum compounds as friction-modifiers .
  • the invention provides lubricating compositions which contain the organic molybdenum compounds .
  • the compounds of this invention can be produced, for example, by means of the reactions indicated below.
  • R is, for example, an alkyl group which has from 1 to 30 carbon atoms and R' is, for example, an alkyl group which has from 1 to 30 carbon atoms, or the two R' may, together with the N, form a five-membered or six-membered ring.
  • the alkyl groups which have from 1 to 30 carbon atoms in the aforementioned R or R' may be linear chain or branched alkyl groups.
  • n-hexadecyl, n-pentadecyl, n-octadecyl, n-nonadecyl, n-eicosyl and the like can be cited as examples.
  • -CNR' 2 When the abovementioned -CNR' 2 is a five-membered ring, -CNR' 2 can be represented, for example, by:
  • Z 1 to Z 4 are elements each selected individually from among the group comprising C, 0, N and S, and in the case of C and N among these, adjacent C and N may form a double bond.
  • R 1 to R 4 and R 1' to R 4' are groups each selected individually from among the group comprising hydrogen and the alkyl groups which have from 1 to 30 carbon atoms, but these groups are not present in those cases where the bonding capacity is saturated by Z 1 to Z 4 forming a ring.
  • -CNR' 2 When the abovementioned -CNR' 2 is a six-membered ring, -CNR' 2 can be represented, for example, by:
  • Z 5 to Z 9 are elements each selected individually from among the group comprising C, O, N and S, and in the case of C and N among these, adjacent C and N may form a double bond.
  • R 5 to R 9 and R 5' to R 9' are groups each selected individually from among the group - -
  • substituent groups which can be represented by R 1 to R 9 and R 1' to R 9' on the aforementioned five-membered rings such as a tetrazole ring or six-membered rings such as a morpholine ring.
  • the alkyl groups which have from 1 to 30 carbon atoms may be linear chain or branched groups. Methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, n- _ -
  • Molybdenum ( IV) diethylamino) xanthate
  • Molybdenum ( IV) di-n-propylamine ⁇
  • Molybdenum ( IV) (di-isopropylamino) xanthate
  • Molybdenum ( IV) (di-n-butylamino) xanthate
  • Molybdenum ( IV) (di-sec-butylamino) xanthate
  • Molybdenum ( IV) (di-t-butylamino) xanthate
  • Molybdenum ( IV) (di-n-pentylamino) xanthate
  • Molybdenum ( IV) (di-2-methylbutylamino) xanthate
  • Molybdenum ( IV) (di-n-hexylamino) xanthate
  • Molybdenum ( IV) (di-2-ethylhexylamino) xanthate
  • Molybdenum ( IV) (di-n-octylamino) xanthate
  • Molybdenum ( IV) (di-n-nonylamino) xanthate
  • Molybdenum ( IV) (di-n-decanylamino) xanthate
  • Molybdenum ( IV) (di-n-undecanylamino) xanthate
  • Molybdenum ( IV) (di-n-tridecanylamino) xanthate
  • Molybdenum ( IV) (di-n-tetradecanylamino) xanthate
  • Molybdenum ( IV) (di-n-pentadecanylamino) xanthate
  • Molybdenum ( IV) (di-n-hexadecanylamino) xanthate
  • Molybdenum ( IV) (di-n-heptadecanylamino) xanthate
  • Molybdenum ( IV) (di-n-octadecanylamino) xanthate
  • Molybdenum ( IV) (di-n-nonadecanylamino) xanthate
  • Molybdenum ( IV) (di-n-eicosanylamino) xanthate
  • CNR' 2 for A is a five-membered ring:
  • CNR' 2 for A is a six-membered ring:
  • the compounds of this invention exhibit a low friction coefficient and they can be used as additives for various types of energy-saving lubricating oil.
  • the compounds of this invention are especially suitable for use in fuel-saving engine oils as they are phosphorus-free .
  • the base oil used in the present invention may conveniently comprise mixtures of one or more mineral oils and/or one or more synthetic oils.
  • Mineral oils include liquid petroleum oils and solvent-treated or acid-treated mineral lubricating oil of the paraffinic, naphthenic, or mixed paraffinic/naphthenic type which may be further refined by hydrofinishing processes and/or dewaxing.
  • Suitable base oils for use in the lubricating oil composition of the present invention are Group I, Group - -
  • Group I base oil By “Group I” base oil, “Group II” base oil and “Group III” base oil in the present invention are meant lubricating oil base oils according to the definitions of American Petroleum Institute (API) categories I, II and III. Such API categories are defined in API Publication 1509, 15th Edition, Appendix E, April 2002.
  • API American Petroleum Institute
  • Suitable Fischer-Tropsch derived base oils that may be conveniently used as the base oil in the lubricating oil composition of the present invention are those as for example disclosed in EP 0 776 959, EP 0 668 342, WO 97/21788, WO 00/15736, WO 00/14188, WO 00/14187, WO 00/14183, WO 00/14179, WO 00/08115, WO 99/41332, EP 1 029 029, WO 01/18156 and WO 01/57166.
  • Synthetic oils include hydrocarbon oils such as olefin oligomers (PAOs), dibasic acid esters, polyol esters, and dewaxed waxy raffinate. Synthetic hydrocarbon base oils sold by the Shell Group under the designation "XHVI” (trade mark) may be conveniently used . Examples
  • a mixed solution of 20 ml of refined water and 20 ml of methylene chloride was prepared in a 200 ml flask - _
  • Dihexylamine (5 ml, 45 mmol) was added to a solution where 0.83 g (45 mmol) of sodium hydroxide had been dissolved in 30 ml of water in a 200 ml flask which had been displaced with Ar and the mixture was stirred for 10 minutes and then 13 ml (45 mmol) of carbon disulphide were added and the mixture was stirred for a further 15 minutes and sodium dioctylthiocarbamate which forms the ligand was formed.
  • Methylene chloride (30 ml) was poured into this mother liquor and then 0.93 g (3.4 mmol) of MoCl 5 was added slowly and the mixture was stirred for 30 minutes.
  • Ammonium pyrrolidinethiocarbamate (6 g, 36.6 mmol) and 15 ml of refined water were added to a 100 ml flask which had been displaced with Ar and the mixture was stirred thoroughly and then 15 ml of methylene chloride were poured in, 0.2 g (0.73 mmol) of MoCl 5 were added slowly and the mixture was stirred for 30 minutes.
  • the organic layer obtained was washed several times using 20 ml of refined water and the organic layer was taken and dried with magnesium sulphate. A reddish-brown coloured solid was isolated by means of column chromatography with methylene chloride.
  • Examples 7 to 12 were prepared by adding each of the compounds obtained in Examples 1 to 6 individually to an ester oil (di-isononyl adipic acid) (with a dynamic viscosity at 100 0 C of 3.04 mm 2 /s) in such a way as to provide a molybdenum content of 500 ppm and also adding 5 mass% of a dispersing agent (alkenylsuccininc acid polyalkylene polyimide, trade name Infineum C9266) .
  • a dispersing agent alkenylsuccininc acid polyalkylene polyimide, trade name Infineum C9266
  • the SRV friction coefficient was measured 1000 times in 30 minutes by a computer and so the minimum value among these is the minimum value of the SRV friction coefficient and the average value for the 1000 measured values is the average value of the SRV friction coefficient .
  • Figure 1 is an outline drawing of the operation of the cylinder-on-disc type reciprocating movement tester.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
  • Pyrrole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention porte sur un composé organique du molybdène ayant la formule générale (1) ci-après dans laquelle -A représente -OR ou -NR' ; les R représentent chacun indépendamment un groupe alkyle ; et les R' représentent chacun indépendamment un groupe alkyle ou deux R' peuvent, conjointement avec le N, former un noyau à cinq chaînons ou à six chaînons, éventuellement substitué. De plus, la présente invention porte sur des compositions lubrifiantes comprenant une huile de base et un composé organique du molybdène selon la présente invention.
PCT/EP2008/053260 2007-03-22 2008-03-19 Composés organiques du molybdène, leur utilisation comme modificateurs de frottement et compositions lubrifiantes Ceased WO2008113814A1 (fr)

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JP2007-074662 2007-03-22
JP2007074662 2007-03-22

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2233554A1 (fr) 2009-03-27 2010-09-29 Infineum International Limited Compositions d'huile lubrifiante
WO2013050426A1 (fr) 2011-10-04 2013-04-11 Universitetet I Oslo Inhibiteurs d'anhydrase carbonique

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7206710B2 (ja) * 2018-09-04 2023-01-18 東ソー株式会社 ジチオカルバミン酸化合物、有機モリブデン錯体、及び潤滑油組成物

Citations (2)

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Publication number Priority date Publication date Assignee Title
WO1988005460A1 (fr) * 1987-01-22 1988-07-28 Erasmus Froeschmann Liquide hydraulique lubrifiant, notamment liquide de frein, son procede de fabrication et utilisation
US5126465A (en) * 1991-04-22 1992-06-30 Exxon Research And Engineering Company Method for making Mo4 S4 L6

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JP3778410B2 (ja) * 1999-08-27 2006-05-24 協同油脂株式会社 自動車ステアリング用グリース組成物
JP5108317B2 (ja) * 2007-02-01 2012-12-26 昭和シェル石油株式会社 アルキルキサントゲン酸モリブデン、それよりなる摩擦調整剤およびそれを含む潤滑組成物

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WO1988005460A1 (fr) * 1987-01-22 1988-07-28 Erasmus Froeschmann Liquide hydraulique lubrifiant, notamment liquide de frein, son procede de fabrication et utilisation
US5126465A (en) * 1991-04-22 1992-06-30 Exxon Research And Engineering Company Method for making Mo4 S4 L6

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ADEOGUN A ET AL: "Studies on molybdenum disulfide nanostructures prepared by AACVD using single-source precursors", CHEMICAL VAPOR DEPOSITION, vol. 12, 2006, pages 597 - 599, XP001501964, ISSN: 0948-1907 *
ARAI K ET AL: "Effect of molybdenum dithiocarbamate on friction and wear properties between aluminum alloy and steel", TRIBOLOGY TRANSACTIONS, vol. 43, no. 1, 2000, pages 45 - 50, XP009102246, ISSN: 1040-2004 *
DATABASE REGISTRY [online] 16 November 1984 (1984-11-16), "Tetrakis(1H-pyrrole-1-carbodithioato-S,S') molybdenum", XP002486434, Database accession no. 86261-12-3 *
LOZANO R ET AL: "Eight-coordinate molybdenum(IV) complexes", ANALES DE QUIMICA, SERIE B, QUIMICA INORGANICA Y QUIMICA ANALITICA, vol. 79, no. 1, 1983, pages 41 - 47, XP009102226, ISSN: 0211-1349 *
LOZANO R ET AL: "Oxidative addition of molybdenum(IV) dialkyldithiocarbamates", ANALES DE QUIMICA, SERIE B, QUIMICA INORGANICA Y QUIMICA ANALITICA, vol. 83, no. 3, 1987, pages 253 - 256, XP009102225, ISSN: 0211-1349 *
NIEUWPOORT A ET AL: "Eight-coordinated 1,1-dithio ligand complexes of molybdenum and tungsten", RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS, vol. 95, no. 10, 1976, pages 250 - 254, XP009102227, ISSN: 0165-0513 *
PERKINS P G ET AL: "Molecular orbital study of some eight-coordinate sulphur chelate complexes of molybdenum", INORGANIC CHEMISTRY, vol. 22, no. 7, 1983, pages 1133 - 1136, XP009102218, ISSN: 0020-1669 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2233554A1 (fr) 2009-03-27 2010-09-29 Infineum International Limited Compositions d'huile lubrifiante
US8101558B2 (en) 2009-03-27 2012-01-24 Infineum International Limited Lubricating oil compositions
WO2013050426A1 (fr) 2011-10-04 2013-04-11 Universitetet I Oslo Inhibiteurs d'anhydrase carbonique

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Publication number Publication date
JP2008266303A (ja) 2008-11-06
JP5314297B2 (ja) 2013-10-16

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