EP0565624A1 - Lubricant adducts and their preparation - Google Patents
Lubricant adducts and their preparationInfo
- Publication number
- EP0565624A1 EP0565624A1 EP92904012A EP92904012A EP0565624A1 EP 0565624 A1 EP0565624 A1 EP 0565624A1 EP 92904012 A EP92904012 A EP 92904012A EP 92904012 A EP92904012 A EP 92904012A EP 0565624 A1 EP0565624 A1 EP 0565624A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- adduct
- lubricant
- fuel
- catalyst
- compound
- 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- Withdrawn
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
- C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/12—Polycyclic non-condensed hydrocarbons
- C07C15/16—Polycyclic non-condensed hydrocarbons containing at least two phenyl groups linked by one single acyclic carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/275—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings having all ether-oxygen atoms bound to carbon atoms of six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
- C07D327/08—[b,e]-condensed with two six-membered carbocyclic rings
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/16—Hydrocarbons
- C10L1/1608—Well defined compounds, e.g. hexane, benzene
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/16—Hydrocarbons
- C10L1/1691—Hydrocarbons petroleum waxes, mineral waxes; paraffines; alkylation products; Friedel-Crafts condensation products; petroleum resins; modified waxes (oxidised)
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
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- C10L1/18—Organic compounds containing oxygen
- C10L1/1817—Compounds of uncertain formula; reaction products where mixtures of compounds are obtained
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- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
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- C10L1/14—Organic compounds
- C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
- C10L1/2406—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides
- C10L1/2412—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides sulfur bond to an aromatic radical
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
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- C10L1/2443—Organic compounds containing sulfur, selenium and/or tellurium heterocyclic compounds
- C10L1/245—Organic compounds containing sulfur, selenium and/or tellurium heterocyclic compounds only sulfur as hetero atom
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- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
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- C10L1/2443—Organic compounds containing sulfur, selenium and/or tellurium heterocyclic compounds
- C10L1/2456—Organic compounds containing sulfur, selenium and/or tellurium heterocyclic compounds sulfur with oxygen and/or nitrogen in the ring, e.g. thiazoles
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- 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/02—Well-defined hydrocarbons
- C10M105/06—Well-defined hydrocarbons aromatic
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/18—Ethers, e.g. epoxides
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/72—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing sulfur, selenium or tellurium
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M127/00—Lubricating compositions characterised by the additive being a non- macromolecular hydrocarbon
- C10M127/06—Alkylated aromatic hydrocarbons
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/16—Ethers
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- 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
- C10M135/20—Thiols; Sulfides; Polysulfides
- C10M135/28—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to a carbon atom of a six-membered aromatic ring
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- 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
- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
- C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
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- 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
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- 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
- C10M2203/06—Well-defined aromatic compounds
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- 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
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
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- 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
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—Amides; Imides
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- 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
- C10M2219/003—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions used as base material
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- 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
- C10M2219/021—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds used as base material
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- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/0406—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides used as base material
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- C10M2219/046—Overbasedsulfonic acid salts
- C10M2219/0463—Overbasedsulfonic acid salts used as base material
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- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/061—Thio-acids; Thiocyanates; Derivatives thereof used as base material
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- 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
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- C10M2223/045—Metal containing thio derivatives
Definitions
- an adduct preparable by catalytically reacting : i) at least one compound comprising at least
- unfused, polynuclear, aromatic compound which may contain at least one chalcogen atom.
- the hydrocarbyl substituent of i) may be aliphatic or cyclic (including aromatic and alicyclic) and may be linear or branched.
- the hydrocarbyl substituent comprises an adduct according to claim 1 wherein the hydrocarbyl substituent comprises a C 3 to C 500 alkyl, alkenyl or alkynyl group, a C 7 to C 500 aralkyl or alkaryl group or a C 6 to C 500 aryl group.
- the hydrocarbyl substituent comprises from 6 to 50 carbon atoms; for example, from 8 to 18 carbon atoms.
- compound i) comprises an alpha olefin. Where compound i) comprises a heteroatom this may be S,N,O,P and/or F.
- compound ii) preferably has the general formula :
- X represents an oxygen or sulphur atom or a
- Y represents a sulphur atom or two hydrogen atoms attached to different aromatic rings.
- compound ii) comprises an adduct according to claim 7 wherein ii) comprises diphenyl ether, diphenyl sulphide, diphenylmethane or phenoxathiin.
- the adducts of this invention prepared over zeolite catalysts have a higher VI at a given viscosity.
- substituent and, optionally, at least one heteroatom; with ii) a substituted or unsubstituted, fused or unfused, polynuclear, aromatic compound which may contain at least one chalcogen atom at a temperature from ambient to 350°C; a molar ratio of i) : ii) from 0.5:1.0 to 10.0:1.0; and a ratio of catalyst : ii) from 1g : 1 mol, preferably 5g:1 mol, to 100 g: 1 mol.
- This invention also provides a high temperature stable lubricant fluid comprising an adduct as herein described.
- the invention further provides a fuel composition comprising an adduct as herein described and a liquid hydrocarbon or oxygenated fuel.
- This invention in a further aspect, provides for the use of an adduct as herein described in a high temperature stable lubricant fluid or a fuel composition for its improved antiwear, high and law temperature antioxidant, antispalling,
- adducts may be by means of a thermal or catalytic addition reaction.
- the exact mechanism of the reaction is not important to the purposes of this invention, so long as the hydrocarbyl substituent becomes attached to the compound (ii) described herein.
- One preferred method of reaction between compound i) and compound ii) is the combination of these reactants in the presence of specific zeolite catalysts; for example Octacat USY and MCM-22. Additional catalysts which could be used
- the catalyst can be used at levels from 1 gram/mole of compound ii) to 100 grams/mole of compound ii), preferably from 5 g/mole of compound ii) to 50 grams/mole of compound ii) and most preferably from 10 to 30 grams catalyst/mole of compound ii).
- the molar ratio of compound i) to compound ii) is from 0.5:1.0 to 10.0:1.0 and preferably from 1.0:1.0 to 4.0:1.0.
- the adducts of this invention can be prepared by reaction in the presence of MCI. and other Lewis acids or in the presence of Bronsted acids, as described in G. A. Olah's "Friedel-Crafts and Related Reactions", Vol. I, 1963,
- detergents and dispersants include sulfonates, phenates, and polymeric succinimides. These can be either metallic or non-metallic. Metallic detergents can be calcium or magnesium derived and can be neutral or overbased.
- the adducts of this invention can be used alone or in combination with other synthetic and/or mineral oil fluids.
- oils of lubricating viscosity When used in combination with other synthetic and/or mineral oil fluids oils of lubricating viscosity may be used.
- mineral oils, both paraffinic, naphthenic and mixtures thereof, employed as the lubricant, or grease vehicle may be of any suitable lubricating viscosity range, as for example, from 45 SSU at 100oF to 6000 SSU at 100oF and preferably, from 50 to 250 SSU at 210oF. These oils may preferably have viscosity indexes up to 95. The average molecular weights of these oils may be from 250 to 800.
- the lubricating oil is generally employed in an amount sufficient to balance the total grease composition, after accounting for the desired quantity of the thickening agent, and other additive components to be included in the grease
- thickening or gelling agents may include any of the conventional metal salts or soaps which are dispersed in the lubricating vehicle in grease-forming quantities in an amount to impart to the resulting grease composition the desired consistency.
- Other thickening agents that may be employed in the grease formulation may comprise non-soap thickeners, such as surface-modified clays and silicas, aryl ureas, calcium complexes and similar materials.
- Typical synthetic oils include polyisobutylene, polybutenes, hydrogenated polydecenes, polypropylene glycol, polyethylene glycol, trimethylpropane esters, neopentyl and pentaerythritol esters, di(2-ethylhexyl) sebacate, di(2-ethylhexyl) adipate, dibutyl phthalate, fluorcarbons, silicate esters, silanes, esters of phosphorus-containing acids, liquid ureas, ferrocene derivatives, hydrogenated synthetic oils, chain-type polyphenyls, siloxanes and silicones (polysiloxanes), alkyl-substituted diphenyl ethers typified by a butyl-substituted bis(p-phenoxy phenyl) ether, phenoxy phenylethers.
- the adducts of the invention When used as additives the adducts of the invention have the ability to improve both the thermal and oxidative stability as well as the additive solubility of the oleagenous materials, i.e., synthetic and/or mineral oil fluids with which they have been blended.
- Lubricant compositions in accordance with the invention may comprise from less than about 1 to about 100% of the adducts of the invention and/or from less than about 100% to about 1% of a synthetic or mineral oil of lubricating viscosity or grease prepared therefrom and from 0.001 to 20 wt% of additive material based on the total weight of the composition.
- Fuel compositions of the invention comprising the adducts herein described include both hydrocarbon fuels, including gasoline, naphtha and diesel fuels or alcoholic fuels or mixtures of alcoholic and hydrocarbon fuels. Fuel compositions can contain 10 to 1,000 pounds of additive per 1,000 barrels of fuel or, more preferably, 25 to 250 pounds per 1,000 barrels of fuel.
- thermocouple and reflux condenser The mixture was then heated to 200oC, with stirring, for six hours. After cooling to room temperature, the mixture was filtered to remove catalyst and vacuum distilled to 170oC at 0.5-1.5 mmBg to remove unreacted starting materials.
- Tetradecene alkylated diphenyl ether hexadecene alkylated phenoxathin and both tetradecene and hexadecene alkylated diphenyl sulfide were compared with polyolefin base stock in a Four-Ball Wear test. The results show that at higher load, both the alkyl diphenyl ether and sulfides and alkyl phenoxathin produced less wear than the other base stock, without any adverse effect on coefficient of friction (f).
- V [15,5 D3 - 0.001033L] D ⁇ 103 mm3
- L is
- K VH
- Load-carrying properties were measured using ASTM D2596 at both room temperature and 100oC.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Lubricants (AREA)
Abstract
Des éthers diphényliques alkylés, des méthanes diphényliques alkylés, des phénoxathines alkylées ainsi que des sulfures diphényliques alkylés constituent des fluides lubrifiants stables à température élevée présentant d'excellentes propriétés viscométriques à basse température ainsi qu'une excellente solubilité d'additifs. Ces additifs peuvent être utilisés comme lubrifiants ou ils peuvent être mélangés à d'autres fluides lubrifiants ou des compositions de carburants.Alkylated diphenyl ethers, alkylated diphenyl methanes, alkylated phenoxathines as well as alkylated diphenyl sulphides constitute lubricating fluids stable at high temperature having excellent viscometric properties at low temperature as well as excellent solubility of additives. These additives can be used as lubricants or they can be mixed with other lubricating fluids or fuel compositions.
Description
Claims
Applications Claiming Priority (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US686454 | 1984-12-26 | ||
US63742591A | 1991-01-04 | 1991-01-04 | |
US68645491A | 1991-04-17 | 1991-04-17 | |
US68645391A | 1991-04-17 | 1991-04-17 | |
US68645291A | 1991-04-17 | 1991-04-17 | |
US686452 | 1991-04-17 | ||
US686453 | 1991-04-17 | ||
US637425 | 2000-08-11 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0565624A1 true EP0565624A1 (en) | 1993-10-20 |
EP0565624A4 EP0565624A4 (en) | 1995-12-27 |
Family
ID=27505219
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP92904012A Withdrawn EP0565624A4 (en) | 1991-01-04 | 1992-01-03 | Lubricant adducts and their preparation |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0565624A4 (en) |
JP (1) | JPH06504289A (en) |
CA (1) | CA2098995A1 (en) |
WO (1) | WO1992012222A1 (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3964471B2 (en) | 1995-06-16 | 2007-08-22 | 東燃ゼネラル石油株式会社 | Heat resistant lubricating oil composition |
JP5994082B2 (en) * | 2012-10-31 | 2016-09-21 | 株式会社Moresco | Alkylated diphenyl ether compound and lubricating oil containing the compound |
CN104395274B (en) * | 2012-10-31 | 2017-12-05 | 株式会社Moresco | Alkylated diphenyl ethers compound and the lubricating oils containing the compound |
US9637424B1 (en) | 2014-12-16 | 2017-05-02 | Exxonmobil Research And Engineering Company | High octane gasoline and process for making same |
US9637423B1 (en) | 2014-12-16 | 2017-05-02 | Exxonmobil Research And Engineering Company | Integrated process for making high-octane gasoline |
US10023533B2 (en) | 2014-12-16 | 2018-07-17 | Exxonmobil Research And Engineering Company | Process to produce paraffinic hydrocarbon fluids from light paraffins |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0377305A1 (en) * | 1989-01-06 | 1990-07-11 | Mobil Oil Corporation | Novel alkylaromatic lubricant fluids |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2221819A (en) * | 1939-05-10 | 1940-11-19 | Dow Chemical Co | Hydrocarbon substituted phenothioxine compounds |
US2277833A (en) * | 1940-06-15 | 1942-03-31 | Dow Chemical Co | Higher alkyl substituted phenothioxins |
US2282686A (en) * | 1940-08-26 | 1942-05-12 | Shell Dev | Antioxidant |
US3240703A (en) * | 1961-12-27 | 1966-03-15 | Universal Oil Prod Co | Stabilization of organic substances |
GB1093945A (en) * | 1963-11-12 | 1967-12-06 | Monsanto Chemicals | Thermally stable alkyldiaryl sulphides and their use as functional fluids |
US4330302A (en) * | 1973-11-21 | 1982-05-18 | Exxon Research & Engineering Co. | High thermal stability liquid hydrocarbons and methods for producing them |
JPS5822515B2 (en) * | 1978-11-27 | 1983-05-09 | 株式会社松村石油研究所 | Lubricating oil for chains used at high temperatures |
US4395372A (en) * | 1982-08-09 | 1983-07-26 | Shell Oil Company | Alkylation process |
US4891448A (en) * | 1987-11-23 | 1990-01-02 | The Dow Chemical Company | Alkylation of polycyclic aromatic compounds to alkylates enriched in the para-substituted isomers |
US5034563A (en) * | 1990-04-06 | 1991-07-23 | Mobil Oil Corporation | Naphthalene alkylation process |
-
1992
- 1992-01-03 EP EP92904012A patent/EP0565624A4/en not_active Withdrawn
- 1992-01-03 WO PCT/US1992/000035 patent/WO1992012222A1/en not_active Application Discontinuation
- 1992-01-03 CA CA 2098995 patent/CA2098995A1/en not_active Abandoned
- 1992-01-03 JP JP4504440A patent/JPH06504289A/en active Pending
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0377305A1 (en) * | 1989-01-06 | 1990-07-11 | Mobil Oil Corporation | Novel alkylaromatic lubricant fluids |
Non-Patent Citations (1)
Title |
---|
See also references of WO9212222A1 * |
Also Published As
Publication number | Publication date |
---|---|
CA2098995A1 (en) | 1992-07-05 |
JPH06504289A (en) | 1994-05-19 |
EP0565624A4 (en) | 1995-12-27 |
WO1992012222A1 (en) | 1992-07-23 |
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