EP3199612A1 - Détergents de métaux - Google Patents

Détergents de métaux Download PDF

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Publication number
EP3199612A1
EP3199612A1 EP16206178.2A EP16206178A EP3199612A1 EP 3199612 A1 EP3199612 A1 EP 3199612A1 EP 16206178 A EP16206178 A EP 16206178A EP 3199612 A1 EP3199612 A1 EP 3199612A1
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EP
European Patent Office
Prior art keywords
detergent
mass
alkyl
organic solvent
unsulfurised
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.)
Withdrawn
Application number
EP16206178.2A
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German (de)
English (en)
Inventor
Dirk Schwaebisch
Jamie Musmacher
Alastair Cant
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.)
Infineum International Ltd
Original Assignee
Infineum International Ltd
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
Priority claimed from US15/006,219 external-priority patent/US9688939B1/en
Priority claimed from EP16155672.5A external-priority patent/EP3205708A1/fr
Application filed by Infineum International Ltd filed Critical Infineum International Ltd
Publication of EP3199612A1 publication Critical patent/EP3199612A1/fr
Withdrawn legal-status Critical Current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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/02—Sulfurised 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
    • C10M177/00—Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
    • 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
    • C10M125/00—Lubricating compositions characterised by the additive being an inorganic material
    • C10M125/06—Sulfur
    • 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
    • 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
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • 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
    • 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/027—Neutral 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/028—Overbased 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
    • 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
    • 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
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/088—Neutral salts
    • 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
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089—Overbased 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
    • C10N2010/04—Groups 2 or 12
    • 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
    • C10N2030/02—Pour-point; Viscosity index
    • 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
    • C10N2030/04—Detergent property or dispersant property
    • 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
    • C10N2030/52—Base number [TBN]
    • 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
    • C10N2040/25—Internal-combustion engines
    • 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions

Definitions

  • This invention relates to a process for preparing sulfurized calcium phenate detergents having a reduced alkylphenol content.
  • Sulfurized calcium alkyl phenate detergents are well-known additive components for internal combustion engine lubricating oil compositions (or lubricants). Unreacted alkylphenol used in their manufacture may be present in the detergents. Such alkylphenols have undesirable properties such as giving rise to corrosion, and certain alkylphenols (e.g. nonylphenol and tetrapropenylphenol) are classified as reproductive toxins.
  • WO 2015/153160 A1 describes preparing an overbased sulfurised alkaline earth metal alkylphenate composition in oil. The composition is heated and subjected to steam stripping followed by filtration. The resulting product is stated to exhibit an improved rate and efficiency of filtration, but further states, without exemplification, that the product may also have a reduced level of free monomeric alkylphenate or alkylphenol (e.g. tetrapropenyl phenol (TPP)) than materials prepared by conventional means without the steam-stripping step.
  • TPP tetrapropenyl phenol
  • US 2014/0142015A describes a method for preparing a salt of a sulfurized alkyl-substituted hydroxyaromatic composition having a reduced content of unsulfurized alkyl-substituted hydroxyaromatic compound and its unsulfurized metal salt.
  • the process involves the addition of an immiscible solvent such as a low molecular weight alcohol (e.g. methanol and ethanol), followed by extraction using a separatory funnel.
  • the solvent needs to be immiscible with the sulfurized alkyl-substituted hydroxyaromatic composition so that separate layers form.
  • One disadvantage of this process is that extra equipment is required in the manufacturing plant (i.e. equipment not previously used in phenate manufacturing plants) to carry out the separation.
  • a solvent not previously used in the manufacturing process needs to be available for use and needs to be stored in a separate storage tank.
  • methanol and ethanol as used in the specific examples in US 2014/0142015 , are toxic solvents.
  • This invention overcomes the problem by adding to the detergent defined proportions of a solvent having a lower boiling point than the alkylphenol as an aid to distillation of the alkylphenol from the detergent without generating species detrimental to the engine.
  • the invention provides a process for preparing sulfurised calcium phenate detergent having a reduced content of unsulfurised alkyl-substituted phenol comprising the steps of:
  • the invention provides a lubricating oil composition
  • a lubricating oil composition comprising an oil of lubricating viscosity in a major amount and a detergent of the second aspect of the invention in a minor amount.
  • the organic solvent is preferably miscible with the sulfurized calcium phenate detergent so that excessive mixing is not required.
  • One advantage of our invention is that distillation is normally used in phenate detergent manufacturing plants so the equipment is readily available.
  • solvents already used in the manufacture of sulfurized calcium phenate detergents can be used as the organic solvent having a boiling point about 100°C, such as, for example, isodecanol.
  • the alkyl groups may be those having 9-100, preferably 9-70, most preferably 9-50, carbon atoms.
  • the art describes preparation of phenate detergents from alkylphenols.
  • the phenates of this invention may, optionally, have been carbonated by reaction with carbon dioxide to give rise to overbased phenates. Specific examples are given in the EXAMPLES section of this specification.
  • organic solvents examples include alkanols and aromatic hydrocarbons. Isodecanol is preferred: it has a boiling point of 220°C, cf 313°C for TPP. It should be noted that the Ca phenate starting material may contain small amounts of organic solvent; amounts given in this specification are those added as in step (B).
  • phenolic functional groups in the product in the product of step (C) may be oxyalkylated such as by reaction with ethylene carbonate, propylene carbonate or butylene carbonate, for example as described in EP-A-2682451 .
  • the oil of lubricating viscosity (sometimes referred to as base oil or lubricating oil) provides a major proportion of the composition and may be any oil suitable for lubricating an internal combustion engine.
  • viscosity may range in viscosity from light distillate mineral oils to heavy lubricating oils. Generally, the viscosity of the oil ranges from 2 to 40 mm 2 /sec, as measured at 100°C.
  • Natural oils include animal oils and vegetable oils (e.g., castor oil, lard oil); liquid petroleum oils and hydrorefined, solvent-treated or acid-treated mineral oils of the paraffinic, naphthenic and mixed paraffinic-naphthenic types. Oils of lubricating viscosity derived from coal or shale also serve as useful base oils.
  • Synthetic lubricating oils include hydrocarbon oils and halo-substituted hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, poly(1-hexenes), poly(1-octenes), poly(1-decenes)); alkybenzenes (e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di(2-ethylhexyl)benzenes); polyphenyls (e.g., biphenyls, terphenyls, alkylated polyphenols); and alkylated diphenyl ethers and alkylated diphenyl sulphides and derivative, analogues and homologues thereof.
  • Alkylene oxide polymers and interpolymers and derivatives thereof where the terminal hydroxyl groups have been modified by esterification, etherification, etc. constitute another class of known synthetic lubricating oils. These may be exemplified by polyoxyalkylene polymers prepared by polymerization of ethylene oxide or propylene oxide, and the alkyl and aryl ethers of polyoxyalkylene polymers (e.g., methyl-polyiso-propylene glycol ether having a molecular weight of 1000 or diphenyl ether of poly-ethylene glycol having a molecular weight of 1000 to 1500); and mono-and polycarboxylic esters thereof, for example, the acetic acid esters, mixed C3-C8 fatty acid esters and C 13 oxo acid diester of tetraethylene glycol.
  • polyoxyalkylene polymers prepared by polymerization of ethylene oxide or propylene oxide
  • alkyl and aryl ethers of polyoxyalkylene polymers e.
  • Another suitable class of synthetic lubricating oils comprises the esters of dicarboxylic acids (e.g., phthalic acid, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkylmalonic acids, alkenyl malonic acids) with a variety of alcohols (e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether, propylene glycol).
  • dicarboxylic acids e.g., phthalic acid, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linole
  • esters includes dibutyl adipate, di(2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, the 2-ethylhexyl diester of linoleic acid dimer, and the complex ester formed by reacting one mole of sebacic acid with two moles oftetraethylene glycol and two moles of 2-ethylhexanoic acid.
  • Esters useful as synthetic oils also include those made from C5 to C12 monocarboxylic acids and polyols and polyol esters such as neopentyl glycol, trimethylolpropane, pentaerythritol, dipentaerythritol and tripentaerythritol.
  • Silicon-based oils such as the polyalkyl-, polyaryl-, polyalkoxy- or polyaryloxysilicone oils and silicate oils comprise another useful class of synthetic lubricants; such oils include tetraethyl silicate, tetraisopropyl silicate, tetra-(2-ethylhexyl)silicate, tetra-(4-methyl-2-ethylhexyl)silicate, tetra-(p-tert-butyl-phenyl) silicate, hexa-(4-methyl-2-ethylhexyl)disiloxane, poly(methyl)siloxanes and poly(methylphenyl)siloxanes.
  • oils include tetraethyl silicate, tetraisopropyl silicate, tetra-(2-ethylhexyl)silicate, tetra-(4-methyl-2-ethylhexy
  • Other synthetic lubricating oils include liquid esters of phosphorus-containing acids (e.g., tricresyl phosphate, trioctyl phosphate, diethyl ester of decylphosphonic acid) and polymeric tetrahydrofurans.
  • Unrefined, refined and re-refined oils can be used in lubricants of the present invention.
  • Unrefined oils are those obtained directly from a natural or synthetic source without further purification treatment.
  • a shale oil obtained directly from retorting operations petroleum oil obtained directly from distillation; or ester oil obtained directly from esterification and used without further treatment, are unrefined oils.
  • Refined oils are similar to unrefined oils except that the oil is further treated in one or more purification steps to improve one or more properties.
  • Many such purification techniques such as distillation, solvent extraction, acid or base extraction, filtration and percolation, are known to those skilled in the art.
  • Re-refined oils are obtained by processes similar to those used to provide refined oils but begin with oil that has already been used in service. Such re-refined oils are also known as reclaimed or reprocessed oils and are often subjected to additional processing using techniques for removing spent additives and oil breakdown products.
  • an oil of lubricating viscosity that may be used in a lubricating oil composition of the present invention, there may be mentioned an oil containing 50 mass % or more of a basestock containing greater than or equal to 90 % saturates and less than or equal to 0.03% sulphur or a mixture thereof. Preferably, it contains 60, such as 70, 80 or 90, mass % or more of said basestock or a mixture thereof.
  • the oil of lubricating viscosity may consist or substantially consist of said basestock or a mixture thereof.
  • Oil of lubricating viscosity may provide 50 mass % or more of the composition. Preferably, it provides 60, such as 70, 80 or 90, mass % or more of the composition.
  • composition may comprise, in addition to the detergent additive of the invention, one or more additive components, different from the additive of the invention, selected from one or more ashless dispersants, detergents, corrosion inhibitors, antioxidants, pour point depressants, antiwear agents, friction modifiers, demulsifiers, antifoaming agents and viscosity modifiers.
  • additive components different from the additive of the invention, selected from one or more ashless dispersants, detergents, corrosion inhibitors, antioxidants, pour point depressants, antiwear agents, friction modifiers, demulsifiers, antifoaming agents and viscosity modifiers.
  • the detergent additives of the invention may be used in lubricants for a range of internal combustion engines (spark-ignited or compression ignited) such as motor vehicle engines and marine engines. Of the latter, there may be mentioned two-stroke marine diesel cross-head engines and marine trunk piston engines.
  • Example 1 (of the invention) reduced the %TPP of the Ca phenate starting material and also gave rise to a considerably lower viscosity product than the reference example.
  • the viscosity measurement for the Reference Example is an order of magnitude too high for it to be useable.

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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)
  • Inorganic Chemistry (AREA)
  • Lubricants (AREA)
  • Detergent Compositions (AREA)
EP16206178.2A 2016-01-26 2016-12-22 Détergents de métaux Withdrawn EP3199612A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US15/006,219 US9688939B1 (en) 2016-01-26 2016-01-26 Metal detergents
EP16155672.5A EP3205708A1 (fr) 2016-02-15 2016-02-15 Détergents de métaux

Publications (1)

Publication Number Publication Date
EP3199612A1 true EP3199612A1 (fr) 2017-08-02

Family

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EP16206178.2A Withdrawn EP3199612A1 (fr) 2016-01-26 2016-12-22 Détergents de métaux

Country Status (6)

Country Link
EP (1) EP3199612A1 (fr)
JP (1) JP2017133004A (fr)
KR (1) KR20170089418A (fr)
CN (1) CN106995738B (fr)
CA (1) CA2956229A1 (fr)
SG (1) SG10201700610YA (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20210141959A (ko) * 2019-03-19 2021-11-23 셰브런 오로나이트 컴퍼니 엘엘씨 낮은 tpp 페네이트 생성을 위한 증류 방법

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US5024773A (en) * 1986-10-21 1991-06-18 Chevron Research Company Methods for preparing, group II metal overbased sulfurized alkylphenols
US5320762A (en) * 1993-03-12 1994-06-14 Chevron Research And Technology Company Low viscosity Group II metal overbased sulfurized C12 to C22 alkylphenate compositions
USRE35461E (en) * 1982-05-14 1997-02-25 Exxon Research And Engineering Company Lubricating oil additives
US6429178B1 (en) * 1996-05-31 2002-08-06 Infineum Usa L.P. Calcium overbased metal-containing detergents
EP2065367A1 (fr) * 2007-11-29 2009-06-03 Chevron Oronite Company LLC Compositions de phénate d'alkyle métalliques sulfurisées dotées d'une faible teneur en phénol d'alkyle
US8198255B2 (en) 2008-05-16 2012-06-12 The Board Of Regents Of The University Of Oklahoma SiRNA-mediated inhibition of doublecortin and Ca2+/calmodulin-dependent kinase-like-1
US8580717B2 (en) * 2009-11-24 2013-11-12 Chevron Oronite Company Llc Process for making an overbased, sulfurized salt of an alkylated hydroxyaromatic compound
EP2682451A1 (fr) 2012-07-06 2014-01-08 Infineum International Limited Modification de détergent
US20140142347A1 (en) * 2012-11-20 2014-05-22 Chevron Oronite Company Llc Process for preparing a salt of a sulfurized alkyl-substituted hydroxyaromatic composition
US20140142015A1 (en) 2012-11-20 2014-05-22 Chevron Oronite Company Llc Solvent extraction for preparing a salt of a sulfurized alkyl-substituted hydroxyaromatic composition
WO2015153160A1 (fr) 2014-04-04 2015-10-08 The Lubrizol Corporation Procédé de préparation d'un dodécylphénate soufré d'un métal alcalinoterreux

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US4744921A (en) * 1986-10-21 1988-05-17 Chevron Research Company Methods for preparing, group II metal overbased sulfurized alkylphenols
JPH051295A (ja) * 1991-06-27 1993-01-08 Idemitsu Kosan Co Ltd 過塩基性硫化アルカリ土類金属フエネートの製造方法
US7163911B2 (en) * 2003-05-22 2007-01-16 Chevron Oronite Company Llc Carboxylated detergent-dispersant additive for lubricating oils
EP2674474B1 (fr) * 2012-06-13 2015-09-09 Infineum International Limited Préparation d'un détergent phénate
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JP2017133004A (ja) 2017-08-03
CN106995738A (zh) 2017-08-01
KR20170089418A (ko) 2017-08-03

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