EP0168110A1 - Procédé de préparation de salicylates surbasiques sulfurés - Google Patents

Procédé de préparation de salicylates surbasiques sulfurés Download PDF

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Publication number
EP0168110A1
EP0168110A1 EP85201082A EP85201082A EP0168110A1 EP 0168110 A1 EP0168110 A1 EP 0168110A1 EP 85201082 A EP85201082 A EP 85201082A EP 85201082 A EP85201082 A EP 85201082A EP 0168110 A1 EP0168110 A1 EP 0168110A1
Authority
EP
European Patent Office
Prior art keywords
product
metal
aliphatic hydrocarbon
salicylic acid
meq
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.)
Granted
Application number
EP85201082A
Other languages
German (de)
English (en)
Other versions
EP0168110B1 (fr
Inventor
Rudolf Frank Heldeweg
Martin Booth
Eugène Marie Godfried Andre van Kruchten
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 EP0168110A1 publication Critical patent/EP0168110A1/fr
Application granted granted Critical
Publication of EP0168110B1 publication Critical patent/EP0168110B1/fr
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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
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • C10M159/22—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing phenol radicals

Definitions

  • This invention relates to a process for the preparation of sulphurized overbased metal aliphatic hydrocarbon-substituted salicylates by sulphurization of an aliphatic hydrocarbon-substituted salicylic acid or a metal salt thereof, to products thus prepared and to oil compositions containing them.
  • This invention therefore relates to a process for the preparation of sulphurized overbased, metal aliphatic hydrocarbon-substituted salicylates by sulphurization of an aliphatic hydrocarbon-substituted salicylic acid or a metal salt thereof with a sulphur halide, and subsequently by transforming the reaction product into an overbased metal salicylate.
  • the invention furthermore relates to the products thus prepared and to oil compositions containing them.
  • Suitable metals of the overbased metal salicylates are e.g. alkali metals, such as Li, Cs, Na and K, alkaline earth metals, such as Ca, Ba, Sr and Mg, and polyvalent metals, such as Zn and Cr.
  • Suitable aliphatic hydrocarbon-substituted salicylic acids are described in the above-mentioned British patent specifications. Preferred are C 8-30 alkyl salicylic acids.
  • an alkali metal salt in particular the sodium salt, is preferred.
  • the sulphurization with sulphur halide is preferably carried out in a solvent such as aliphatic hydrocarbons, e.g. n-hexane.
  • a solvent such as aliphatic hydrocarbons, e.g. n-hexane.
  • aromatic solvents such as xylene
  • Preferred sulphur halides are sulphur chlorides, such as SCl 2 and S 2 C1 2 .
  • the reaction can be carried out at ambient temperature, although some heating may be applied, e.g. up to 60 °C.
  • the molar ratio of S: substituted salicylic acid or salicylate is e.g. 0.25 to 3 preferably 0.5 to 2.
  • reaction mixture may then be acidified, if necessary, to obtain the free sulphurized acid and filtered if desirable.
  • the product is used for the preparation of the corresponding overbased salicylates which combine good detergency with reduced wear in lubricating oil compositions.
  • the overbasing step can be carried out by reacting the resulting product in a solvent, such as a hydrocarbon solvent, preferably an aromatic hydrocarbon solvent, such as xylene, with a basic metal compound, preferably a hydroxide, and carbon dioxide, as described in e.g. British patent specification 786167.
  • a solvent such as a hydrocarbon solvent, preferably an aromatic hydrocarbon solvent, such as xylene
  • a basic metal compound preferably a hydroxide, and carbon dioxide, as described in e.g. British patent specification 786167.
  • the degree of overbasing is expressed as the basicity index (B.I.), defined as the equivalent ratio of metal: salicylic acid.
  • a light mineral oil may be added and then the hydrocarbon solvent, and any water formed may be removed by distillation.
  • the resulting oil solution of the sulphurized product may be filtered, if desired, and then be added to an oil, such as a lubricating oil or a fuel oil, including gasoline.
  • an oil such as a lubricating oil or a fuel oil, including gasoline.
  • the product Before or after sulphurization the product may be reacted with a boron compound, such as boric acid, as described in the copending British patent application 8330441.
  • a boron compound such as boric acid
  • reaction products of this invention including mixtures thereof can be incorporated in oil compositions, in particular lubricating oil compositions or concentrates or fuels, e.g., automotive crankcase oils, in concentrations within the range of 0.001 to 65, in particular 0.1 to 15 %w based on the weight of the total compositions.
  • the lubricating oils to which the additives of the invention can be added include not only mineral lubricating oils, but synthetic oils also. Synthetic hydrocarbon-lubricating oils may also be employed, as well as non-hydrocarbon synthetic oils including dibasic acid esters such as di-2-ethyl hexyl sebacate, carbonate esters, phosphate esters, halogenated hydrocarbons, polysilicones, polyglycols, glycol esters such as C 13 oxo acid diesters of tetraethylene glycol, etc. Mixtures of these oils, in particular of mineral lubricating oils, including hydrogenated oils, and synthetic lubricating oils, can also be used.
  • additives may also be present, including dyes, pour point depressants, anti-wear, e.g., tricresyl phosphate, zinc dithiophasphates, antioxidants such as phenyl- alpha-naphthyl-amine, bis-phenols such as 4,4'-methylene bis (3,6-di-tert-butylphenol), viscosity index inprovers, such as hydrogenated (co)polymers of conjugated dienes and optionally styrene, ethylene-higher olefin copolymers, polymethylacrylates, polyisobutylene, and the like as well as ashless dispersants, such as reaction products of polyisobutylene, maleic anhydride and amines and/or polyols, or other metal-containing detergents, such as overbased metal salicylates.
  • dyes e.g., tricresyl phosphate, zinc dithiophasphates
  • antioxidants such as pheny
  • Reaction products of amines, formaldehyde and alkyl phenols can also be present.

Landscapes

  • 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)
  • Liquid Carbonaceous Fuels (AREA)
EP85201082A 1984-07-06 1985-07-04 Procédé de préparation de salicylates surbasiques sulfurés Expired EP0168110B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB848417298A GB8417298D0 (en) 1984-07-06 1984-07-06 Preparation of sulphurized overbased salicylates
GB8417298 1984-07-06

Publications (2)

Publication Number Publication Date
EP0168110A1 true EP0168110A1 (fr) 1986-01-15
EP0168110B1 EP0168110B1 (fr) 1988-09-28

Family

ID=10563524

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85201082A Expired EP0168110B1 (fr) 1984-07-06 1985-07-04 Procédé de préparation de salicylates surbasiques sulfurés

Country Status (8)

Country Link
EP (1) EP0168110B1 (fr)
JP (1) JPS6124561A (fr)
BR (1) BR8503202A (fr)
CA (1) CA1255691A (fr)
DE (1) DE3565258D1 (fr)
GB (1) GB8417298D0 (fr)
SG (1) SG6790G (fr)
ZA (1) ZA855047B (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2554825A1 (fr) * 1983-11-15 1985-05-17 Shell Int Research Sel metallique basique borate et composition d'huile lubrifiante le contenant
US4876020A (en) * 1987-06-25 1989-10-24 Shell Oil Company Lubricating oil composition
US6716817B1 (en) 1993-02-19 2004-04-06 Zentaris Ag Method of treatment of female infertility
EP1754699A2 (fr) * 2005-07-29 2007-02-21 Chevron Oronite S.A. Detergent.dispersants métaliques à faible contenance en soufre.
WO2016124291A1 (fr) * 2015-02-06 2016-08-11 Castrol Limited Utilisation d'un détergent à base d'acide salicylique à substitution hydrocarbyle comme inhibiteur de la corrosion par le plomb

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH059522Y2 (fr) * 1986-10-16 1993-03-09

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2311931A (en) * 1941-12-27 1943-02-23 American Cyanamid Co Lubricant
US2319662A (en) * 1941-10-31 1943-05-18 American Cyanamid Co Lubricating oils
US2335017A (en) * 1941-12-31 1943-11-23 Standard Oil Dev Co Lubricating composition
US2336074A (en) * 1942-05-16 1943-12-07 American Cyanamid Co Lubricating oil
GB786167A (en) * 1954-09-27 1957-11-13 Shell Res Ltd Improvements in or relating to the preparation of basic oil-soluble polyvalent metalsalts of organic acids and solutions of said basic salts in oils, and the resultingsalts
GB825315A (en) * 1957-02-18 1959-12-16 Socony Mobil Oil Co Inc Complex carbonated metal salts of alkyl phenol sulphides
GB1194503A (en) * 1965-08-23 1970-06-10 Lubrizol Corp Basic Sulfurised Salicylates and method for their preparation
US3595790A (en) * 1969-10-22 1971-07-27 Lubrizol Corp Oil soluble highly basic metal salts of organic acids
GB1287812A (en) * 1969-03-11 1972-09-06 Lubrizol Corp Basic, sulfurized salicylates and method for their preparation
US4221673A (en) * 1977-01-28 1980-09-09 Exxon Research & Engineering Co. Metal phenates
US4320016A (en) * 1979-09-24 1982-03-16 Texaco Inc. Carbon dioxide-blown overbased calcium alkylphenolate lubricating compositions

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2256441A (en) * 1940-03-08 1941-09-16 Socony Vacuum Oil Co Inc Mineral oil composition and improving agent therefor
JPS60147497A (ja) * 1984-01-09 1985-08-03 Cosmo Co Ltd サリチレ−トを含有する塩基性硫化アルカリ土類金属フエネ−ト型清浄剤の製造方法
JPS60168793A (ja) * 1984-02-13 1985-09-02 Cosmo Co Ltd 塩基性硫化アルカリ土類金属フエネ−ト型清浄剤の製造法

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2319662A (en) * 1941-10-31 1943-05-18 American Cyanamid Co Lubricating oils
US2311931A (en) * 1941-12-27 1943-02-23 American Cyanamid Co Lubricant
US2335017A (en) * 1941-12-31 1943-11-23 Standard Oil Dev Co Lubricating composition
US2336074A (en) * 1942-05-16 1943-12-07 American Cyanamid Co Lubricating oil
GB786167A (en) * 1954-09-27 1957-11-13 Shell Res Ltd Improvements in or relating to the preparation of basic oil-soluble polyvalent metalsalts of organic acids and solutions of said basic salts in oils, and the resultingsalts
GB825315A (en) * 1957-02-18 1959-12-16 Socony Mobil Oil Co Inc Complex carbonated metal salts of alkyl phenol sulphides
GB1194503A (en) * 1965-08-23 1970-06-10 Lubrizol Corp Basic Sulfurised Salicylates and method for their preparation
GB1287812A (en) * 1969-03-11 1972-09-06 Lubrizol Corp Basic, sulfurized salicylates and method for their preparation
US3595790A (en) * 1969-10-22 1971-07-27 Lubrizol Corp Oil soluble highly basic metal salts of organic acids
US4221673A (en) * 1977-01-28 1980-09-09 Exxon Research & Engineering Co. Metal phenates
US4320016A (en) * 1979-09-24 1982-03-16 Texaco Inc. Carbon dioxide-blown overbased calcium alkylphenolate lubricating compositions

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2554825A1 (fr) * 1983-11-15 1985-05-17 Shell Int Research Sel metallique basique borate et composition d'huile lubrifiante le contenant
US4876020A (en) * 1987-06-25 1989-10-24 Shell Oil Company Lubricating oil composition
US6716817B1 (en) 1993-02-19 2004-04-06 Zentaris Ag Method of treatment of female infertility
EP1754699A2 (fr) * 2005-07-29 2007-02-21 Chevron Oronite S.A. Detergent.dispersants métaliques à faible contenance en soufre.
EP1754699A3 (fr) * 2005-07-29 2007-04-25 Chevron Oronite S.A. Detergent.dispersants métaliques à faible contenance en soufre.
EP2295405A1 (fr) 2005-07-29 2011-03-16 Chevron Oronite S.A. Détergent-dispersants métalliques à faible contenance en soufre
EP2316823A1 (fr) 2005-07-29 2011-05-04 Chevron Oronite S.A. Detergent-dispersants métaliques à faible contenance en soufre
US7956022B2 (en) 2005-07-29 2011-06-07 Chevron Oronite Company Llc Low sulfur metal detergent-dispersants
WO2016124291A1 (fr) * 2015-02-06 2016-08-11 Castrol Limited Utilisation d'un détergent à base d'acide salicylique à substitution hydrocarbyle comme inhibiteur de la corrosion par le plomb
US10907111B2 (en) 2015-02-06 2021-02-02 Castrol Limited Use of a hydrocarbyl-substituted salicylic acid detergent as an inhibitor of lead corrosion

Also Published As

Publication number Publication date
JPH0580518B2 (fr) 1993-11-09
JPS6124561A (ja) 1986-02-03
SG6790G (en) 1990-07-13
CA1255691A (fr) 1989-06-13
BR8503202A (pt) 1986-03-25
GB8417298D0 (en) 1984-08-08
EP0168110B1 (fr) 1988-09-28
DE3565258D1 (en) 1988-11-03
ZA855047B (en) 1986-02-26

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