+

WO2018144301A1 - Mélanges à température de transition basse et huiles lubrifiantes contenant ceux-ci - Google Patents

Mélanges à température de transition basse et huiles lubrifiantes contenant ceux-ci Download PDF

Info

Publication number
WO2018144301A1
WO2018144301A1 PCT/US2018/015143 US2018015143W WO2018144301A1 WO 2018144301 A1 WO2018144301 A1 WO 2018144301A1 US 2018015143 W US2018015143 W US 2018015143W WO 2018144301 A1 WO2018144301 A1 WO 2018144301A1
Authority
WO
WIPO (PCT)
Prior art keywords
component
composition
diol
cst
range
Prior art date
Application number
PCT/US2018/015143
Other languages
English (en)
Inventor
Abhimanyu O. Patil
Satish Bodige
Thilina N. GUNASEKARA
Original Assignee
Exxonmobil Chemical Patents Inc.
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 Exxonmobil Chemical Patents Inc. filed Critical Exxonmobil Chemical Patents Inc.
Publication of WO2018144301A1 publication Critical patent/WO2018144301A1/fr

Links

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
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/06—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
    • 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
    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • C10M111/02—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a non-macromolecular organic compound
    • 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
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02—Water
    • 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
    • C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
    • C10M2207/0225—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups 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
    • 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
    • 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
    • C10M2207/0235—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • C10M2215/0425—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof used as base material
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; 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
    • C10N2030/02—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
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • 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
    • C10N2030/54—Fuel economy
    • 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

Definitions

  • the present invention relates to organic low-transition-temperature eutectic mixtures (LTTMs) and lubricant oils containing the same.
  • LTTMs organic low-transition-temperature eutectic mixtures
  • lubricant oils containing the same.
  • the present invention relates to LTTMs comprising a eutectic mixture of a quaternary amine and a polyol and lubricant base oils and lubricant formulations containing the same.
  • a major challenge in engine oil formulation is simultaneously achieving wear control, and friction reduction, while also maintaining fuel economy performance, over a broad temperature range.
  • Lubricant-related wear control is highly desirable due to increasing use of low viscosity engine oils for improved fuel efficiency. As governmental regulations for vehicle fuel consumption and carbon emissions become more stringent, use of low viscosity engine oils to meet the regulatory standards is becoming more prevalent. At the same time, lubricants need to provide a substantial level of wear protection and friction reduction due to the formation of thinner lubricant films during engine operation. As such, use of antiwear additives and friction modifiers in a lubricant formulation is the typical method for achieving wear control and friction reduction. Due to limitations of using high levels of antiwear and friction modifier additives such as catalyst poisoning and deposit formation, it is highly desirable to find alternative methods for achieving excellent wear control and friction reduction without poisoning the catalyst.
  • Developing more effective additive package in combination with balancing lubricant viscosity has proven to be a successful and cost-effective route to improving engine efficiency and durability.
  • Commercial lubricants are composed of base stock and several categories of additives including anti-wear, friction modifier, viscosity modifier, antioxidant, detergent, dispersant, etc.
  • friction modifiers and anti-wear agents play key role in reducing boundary and mixed friction and wear in engine locations such as the top-ring- reversal region of the piston ring-cylinder liner interface and sliding surfaces in the valve train.
  • an effective anti-wear additive allows using a low viscosity lubricant, consequently reducing elasto-hydrodynamic friction loss.
  • PAOs Polyalpha-olefins
  • VI high viscosity index
  • KV100 low volatility
  • KV100 low volatility
  • lube formulators usually add one or multiple polar co-base stocks.
  • Ester or alkylated naphthalene (AN) is usually present at 1 to 50 wt% levels in many finished lubricant formulations to increase the fluid polarity which improves the solubility of polar additives and sludge.
  • Ionic liquids have been an active area of research at various universities, government labs and companies. Ionic liquids are effective lube additives but can have disadvantages such as toxicity, high cost, limited range of available raw materials, and difficulties in achieving a high purity.
  • U.S. Patent Publication No. 2016/0122676 Al describes low transition temperature mixtures or deep eutectic solvents and processes for preparation thereof.
  • Various low transition temperature mixtures are described, including mixtures of choline chloride with malic acid or lactic acid.
  • low-transition-temperature liquid containing a eutectic mixture of a quaternary amine and a polyol can be advantageously used as a lubricating oil base stock given its low glass transition temperature, high viscosity index, low traction coefficient, and kinematic viscosity at the normal use temperatures of lubricants.
  • a composition comprising a eutectic mixture.
  • the mixture can include a first component comprising a quaternary amine having at most 6 carbon atoms per molecule.
  • the mixture can further include a second component comprising a polyol having at least two alcoholic hydroxyl functional groups per molecule.
  • a molar ratio of the first component to the second component in the mixture can be in a range from 1 : 1 to 1:9.
  • the composition can further exhibit a glass transition temperature of no higher than -70°C, a viscosity index of at least 60, and a kinematic viscosity at 100°C in a range from 2.0 to 40 cSt.
  • the eutectic mixture can exhibit a low transition temperature.
  • a composition comprising a eutectic mixture based on a quaternary amine as a first component and a glycol as a second component.
  • the quaternary amine has at most 6 carbon atoms per molecule.
  • the glycol is preferably ethylene glycol.
  • a molar ratio of the first component to the second component in the mixture can range from 1 :2 to 1 :6.
  • the composition can exhibit a glass transition temperature of no higher than -110°C, a viscosity index of at least 90, and a kinematic viscosity at 100°C in a range from 2.0 to 6.0 cSt.
  • a lubricating oil can include a primary lubricating oil base stock and a secondary lubricant component.
  • the secondary lubricant component has a composition capable of forming a eutectic mixture if not added into the lubricating oil.
  • the eutectic mixture can include a first component comprising a quaternary amine comprising at most 6 carbon atoms per molecule and a second component comprising a polyol comprising at least two alcoholic hydroxyl functional groups per molecule.
  • the eutectic mixture can be an equilibrium phase between the first component and the second component.
  • a molar ratio of the first component to the second component in the eutectic mixture can range from 1 : 1 to 1 :9.
  • the eutectic mixture can exhibit a glass transition temperature of no higher than -70°C, a viscosity index of at least 60, and a kinematic viscosity at 100°C in a range from 2.0 to 40 cSt.
  • FIG. 1 shows portions of a NMR spectra of the LTTM of Example 1.
  • FIG. 2 shows a differential scanning calorimetry ("DSC") diagram of the LTTM of Example 1.
  • FIG. 3 shows a DSC diagram of the LTTM of Example 3.
  • FIG. 4 shows a DSC diagram of the LTTM of Example 5.
  • FIG. 5 shows a DSC diagram of the LTTM of Example 6.
  • FIG. 6 shows a DSC diagram of the LTTM of Example 8.
  • FIG. 7 shows a DSC diagram of the LTTM of Example 10.
  • FIG. 8 shows a DSC diagram of the LTTM of Example 12.
  • FIG. 9 shows traction curves of the LTTM of Example 16 comprising choline chloride and ethylene glycol at a molar ratio of 1 :2 at a series of temperatures.
  • FIGs. 10 and 11 schematically show the interaction of the components in the comparative ionic liquid of Example 18 and the comparative LTTM of Example 19, respectively.
  • FIG. 12 shows Fourier Transform Infrared ("FTIR") spectra and DSC diagrams of the ionic liquid of comparative Example 18 and a comparative LTTM of comparative Example 19, respectively.
  • FTIR Fourier Transform Infrared
  • FIG. 13 shows DSC diagrams of an ionic liquid and an LTTM based on choline chloride and lactic acid, respectively.
  • LTTM low-transition-temperature material
  • DSC differential scanning calorimetry
  • choline chloride also abbreviated as "CC" means a compound having a structure corresponding to the following general formula:
  • Betaine as used in the present disclosure has the following structure:
  • a polyol refers to an organic compound comprising at least two alcoholic hydroxyl (-OH) groups per molecule which can be represented by the formula HO- R-OH, where the two hydroxyls are alcoholic (i.e., not a part of a carboxylic acid group), and the linking moiety -R- can be a -CR ⁇ -CR 2 !!- moiety or a -CR ⁇ -Rs-CR 2 !!- moiety, wherein: R 1 and R 2 can be, independently at each occurrence, a hydrogen, a saturated or unsaturated, substituted or unsubstituted, linear or cyclic aliphatic hydrocarbyl group, or a substituted or unsubstituted aromatic hydrocarbyl group, or alternatively, one or more of the R 1 , R 2 and the intermediate atoms and moieties in between may, taken together, form a cyclic moiety that is saturated or unsaturated, aliphatic or aromatic, with or
  • R 4 is a linear, branched, or cyclic, saturated or unsaturated, substituted or unsubstituted, hydrocarbyl group.
  • An aliphatic polyol herein refers to a polyol containing at least two alcoholic hydroxyl groups directly connected to carbon atom(s) that do not form part of an aromatic structure.
  • An aromatic polyol herein refers to a polyol containing at least two alcoholic hydroxyl groups, at least one of which is directly connected to a carbon atom that forms part of one or more aromatic structure(s).
  • aromatic polyols include, but are not limited to: 1,2-benzenediol (catechol), 1,3-benzenediol (resorcinol), 1,4-dihydroxybenzene (hydroquinone), benzene- 1, 2,3 -triol, benzene-l,2,4-triol; benzene- 1, 2,5 -triol, benzene-1,3,5- triol, and the like.
  • An "analogue" of an aromatic polyol is an aromatic polyol comprising, in addition to the basic alcohol structure of the aromatic polyol, one or more aliphatic groups (linear, branched, or cyclic) connected directly to the aromatic structure.
  • a "eutectic mixture” as uwsed herein refers to a mixture comprising two or more compounds which interact with each other to prevent the crystallization of each compound individually, resulting in a system having a melting point or a glass transition temperature lower than the normal melting points of the individual compounds in their pure forms.
  • lubricant refers to a substance that can be introduced between two or more surfaces and lowers the level of friction between two adjacent surfaces moving relative to each other.
  • a lubricant “base stock” is a material, typically a fluid at the operating temperature of the lubricant, used to formulate a lubricant by admixing with other components.
  • base stocks suitable in lubricants include API Group I, Group II, Group III, Group IV, and Group V base stocks.
  • PAOs, particularly hydrogenated PAOs have recently found wide use in lubricant formulations as a Group IV base stock, and are particularly preferred.
  • kinematic viscosity at 100°C (“KV100”) and kinematic viscosity at 40°C (“KV40”) are measured using ASTM D445.
  • Viscosity index (“VI”) is determined according to ASTM D2270. Pour points are determined using ASTM D97.
  • low transition temperature mixtures based on polyols including two or more alcoholic hydroxyl groups per molecule (i.e., a polyol) are provided.
  • the polyol-based LTTMs can provide various beneficial properties, such as high viscosity index values, low glass transition temperatures relative to the phase transition properties of the mixture components, and/or high kinematic viscosities, especially in view of the typically small molecular weight of the mixture components.
  • glycol-based LTTMs such as ethylene glycol-based LTTMs
  • the number of carbon atoms per molecule in the compound including two or more hydroxyl groups can be at most: 6, 5, 4, 3, or 2.
  • the LTTMs also include a quaternary amine that includes at most 6, or at most 5, or at most 4, or at most 3, carbon atoms per molecule, such as choline chloride or betaine.
  • the molar ratio of polyol to quaternary amine in the resulting eutectic mixture can depend on the nature of the respective compounds. Examples of suitable molar ratios of quaternary amine to polyol can range from 1 : 1 to 1 : 10 or from 1 : 1 to 1 :9 or from 1 :2 to 1 :9 or from 1 : 1 to 1 :4 or from 1 :4 to 1 : 10 or from 1 :4 to 1 :9. Examples of particularly useful quaternary amines for the LTTMs, eutectic mixtures and/or base stocks according to the present disclosure are choline chloride ("CC"), betaine, and mixtures and combinations thereof.
  • CC choline chloride
  • betaine betaine
  • the low transition temperature mixtures based on a eutectic mixture of the quaternary amine and the polyol can have beneficial properties for use as a lubricant base stock.
  • the LTTMs can have a VI of at least 60, or at least 80, or at least 100, or at least 120, or at least 140, such as up to 180 or more.
  • the LTTMs can have a KV100 of 2.0 to 40 cSt, or 2.0 to 30 cSt, or 2.0 to 10 cSt, or 2.0 to 6.0 cSt, or 2.0 to 4.0 cSt, or 4.0 to 40 cSt, or 4.0 to 30 cSt, or 4.0 to 6.0 cSt.
  • the LTTMs can have lower glass transition temperatures compared to the melting points and/or glass transition temperatures of the components forming the eutectic mixture.
  • the glass transition temperature of the LTTM can be no higher than: -70°C, -75°C, -80°C, -85°C, -90°C, -95°C, -100°C, -105°C, -110°C, or even -120°C.
  • LTTMs of the present disclosure are mixtures of quaternary amines with glycols (such as ethylene glycol, "EG”) and mixtures of quaternary amines with glycerols (such as 1,2,3-propanetriol).
  • glycols such as ethylene glycol, "EG”
  • glycerols such as 1,2,3-propanetriol
  • glycols include, but are not limited to: ethylene glycol, propylene glycol, propane- 1,2-diol, butane- 1,4-diol, butane-2,3-diol, butane- 1,3-diol, pentane-l,5-diol, pentane- 1,4-diol, pentane-l,3-diol, pentane- 1,2-diol, pentane-2,3-diol, pentane-2,4-diol, hexane- 1,2-diol, hexane- 1,3-diol, hexane- 1,4-diol, hexane-l,5-diol, hexane- 1,6-diol, hexane-2,3-diol, hexane-2,4-diol, hexane- 2,5
  • a particularly useful glycol for the LTTMs of the present disclosure is ethylene glycol due to, among others, its commercial availability and ease of use.
  • the molar ratio of the quaternary amine to ethylene glycol in the LTTMs can range from, e.g., 1:2 to 1:9, or 1 :2 to 1:4.
  • LTTMs made from choline chloride ("CC"), betaine, or mixtures and combinations thereof as the quaternary amine and ethylene glycol can exhibit unusual properties.
  • the VI of a CC/EG LTTM can be at least 90, or at least 100, or at least 110, or at least 120, such as up to 200 or more.
  • the VI of the resulting LTTM can be from 170 to 180.
  • the glass transition temperature of LTTMs made using ethylene glycol can also be low.
  • the glass transition temperature can be no higher than -90°C, or no higher than - 100°C, or no higher than -110°C.
  • the low-transition-temperature mixtures can correspond to mixtures of a quaternary amine with an aromatic polyol, such as catechol, resorcinol, benzene-l,2,3-triol, benzene- 1,2,4-triol; benzene-l,2,5-triol, benzene-l,3,5-triol, and the like.
  • the molar ratio of quaternary amine to aromatic polyols can range from 1 : 1 to 1 :4, or 1: 1 to 1 :2.
  • Such LTTMs can exhibit highly desirable properties.
  • the VI of the LTTM can be at least 60, or at least 80, such as up to 200 or more.
  • the glass transition temperature of LTTMs made using ethylene glycol can also be low.
  • the glass transition temperature can be no higher than -70°C.
  • the LTTMs can also have an unusually high KV100 of at least 20 cSt, or in the range from 20 to 30 cSt.
  • the fluid mixtures corresponding to LTTMs may show (eutectic) melting points (a phase transition) or preferably may show glass transitions instead in DSC diagrams.
  • the molar ratio of quaternary amine to aromatic polyol can range from 1 : 1 to 1 :4, or 1 : 1 to 1 :2, or 1 :2 to 1 :4.
  • Such LTTMs based on aromatic polyol can exhibit highly desirable properties and/or combinations thereof, for example: glass transition temperature no higher than -70°C; KV100 of at least 4.0 cSt, or at least 10 cSt; and VI of at least 70, or at least 80, or at least 90. Formation of LLTMs
  • the LTTMs of the present disclosure are particularly useful as synthetic base stocks and/or as lubricant additives for lubricant compositions.
  • the LTTM of the present disclosure can be anhydrous, while in others the LTTM can remain stable while incorporating 0.1 to 5.0 wt% water, or 0.1 to 3.0 wt%.
  • a method for making a eutectic mixture described above can start with a component that is a liquid at room temperature. Alternatively and additionally, the process can include a step of heating a component having the lowest melting point to the temperature at which it melts. The remaining component or components can then be dissolved in the liquid or melted component.
  • eutectic mixtures which for purposes of the present disclosure means an equilibrium phase between two or more components, which equilibrium phase, or mixture, has different physical characteristics than the individual components.
  • the eutectic mixtures described herein are desirably formed, e.g., in the absence of any additional solvent that dissolves both compounds.
  • the individual components must be compatible, i.e., each compound must form an intermolecular interaction with the other, so that this interaction will counteract the usual forces that tend to arrange the individual components into their individual crystalline forms. Without being bound by any particular theory, it is believed that this result is only obtainable when the components are mixed on the molecular level.
  • the lube acceptable eutectic mixtures of this disclosure can be prepared under various pre-defined conditions.
  • the mixtures of the disclosure can also provide for delivery of potential additives in a controlled fashion or controlled release manner that has limited solubility in lubes. The delivery can be triggered, for example by either heat, moisture, or other solvent.
  • These LTTMs can potentially overcome some of the limitations of ionic liquids such as their potential toxicity, high cost and difficulties in getting fluids in high purity. These mixtures may have the advantage of being inexpensive, and easy to prepare from natural and readily available starting materials.
  • the ionic liquids are ionic compounds while LTTMs are mixtures.
  • ionic liquids In ionic liquids the crystallization can be avoided via the choice of unsymmetrical organic cations and anions; whereas in LTTMs it is hydrogen bonding or van der Waals forces that interfere with the ability of the initial compounds to crystallize.
  • Limitations of ionic liquids include, for example, high cost and difficulties in getting ionic liquid fluids in high purity.
  • LTTMs have advantage of being inexpensive, easy to prepare from natural materials, and readily available starting materials.
  • Illustrative advantages of the LTTMs of this disclosure include, for example, inexpensive and easy preparation, renewable and biodegradable, wide liquid range, good solvation properties, ability to customize properties as a function of constituents nature and ratio and conditions applied, and easy recovery using an anti-solvent.
  • compositions of this disclosure can be prepared by a process that involves providing at least a first component and at least a second component.
  • at least one of first component and the second component can be a solid 20°C.
  • the process further involves heating the first component and/or the second component. If both of the components are solid at room temperature, whichever component has the lowest melting point can be heated to a temperature sufficient to melt the component. In such cases, the remaining component(s) can then be dissolved in the melted component.
  • the heating of the components in a liquid state can provide sufficient molecular mixing to form a eutectic mixture.
  • Process conditions for the preparation of the eutectic mixtures of this disclosure may also vary greatly and any suitable combination of such conditions may be employed herein.
  • the reaction temperature may range from -10°C to 250°C, and preferably from 0°C to 200°C, and more preferably from 25°C to 150°C. Normally the reaction is carried out under ambient pressure and the contact time may vary from a matter of seconds or minutes to a few hours or greater.
  • the reactants can be added to the reaction mixture or combined in any order.
  • the stir time employed can range from 0.5 to 72 hours, preferably from 1 to 36 hours, and more preferably from 2 to 24 hours.
  • compositions formed by the process described above examples include, but are not limited to, analytical gas chromatography, FTIR spectroscopy, nuclear magnetic resonance, thermogravimetric analysis (TGA), inductively coupled plasma mass spectrometry, differential scanning calorimetry (DSC), volatility and viscosity measurements.
  • TGA thermogravimetric analysis
  • DSC differential scanning calorimetry
  • volatility and viscosity measurements are examples of techniques that can be employed to characterize the compositions formed by the process described above.
  • This disclosure provides lubricating oils comprising a component having a composition capable of forming a eutectic mixture described above when not mixed with other components of the oil.
  • the lubricating oils comprise a primary lubricant base stock and a secondary lubricant component having a composition, if not added to the lubricant, capable of forming a eutectic mixture described above.
  • the primary lubricant base stock may constitute, based on the total weight of the lubricant oil, from cl to c2 wt%, where cl and c2 can be, independently, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, as long as cl ⁇ c2.
  • the secondary lubricant component which can be a co-base stock, an additive, or other component, may constitute, based on the total weight of the lubricant oil, from c3 to c4 wt%, where c3 and c4 can be, independently, 0.1, 0.2, 0.4, 0.5, 0.6, 0.8, 1.0, 2.0, 4.0, 5.0, 6.0, 8.0, 10, 15, 20, as long as c3 ⁇ c4.
  • the lubricant oils of the present disclosure are useful as, e.g., automotive engine oils, gear box oils, transmission oils, power-line oils, industrial lubricant oils and greases, industrial gear box oils, wind turbine lubricant oil, and in other applications.
  • the lubricant oil can have excellent solvency and dispersancy characteristics.
  • the lubricating oil base stock can be any oil boiling in the lube oil boiling range, typically from 100°C to 450°C. In the present specification and claims, the terms base oil(s) and base stock(s) are used interchangeably.
  • the lubricant oil of the present disclosure can be formulated by combining a prefabricated eutectic mixture described above with other components such as other base oils, additives, and the like.
  • the pre-fabricated eutectic mixture can be a co-base stock, an additive, or other component of the final lubricant oil composition.
  • the lubricant oil can be formulated by combining the first component, the second component and other optional components of the eutectic mixture at the quantities desirable for making the eutectic mixture with other components of the lubricant oil such as other base oils, additives, and the like.
  • a eutectic mixture of the present disclosure is included in a lubricant oil composition, it has been found that wear control of the lubricated surfaces can be improved, friction can be reduced, and fuel efficiency can be maintained or improved as compared to wear control, friction reduction and fuel efficiency achieved using a lubricating engine oil containing a co-base stock other than the eutectic mixture co-base stock.
  • a wide range of lubricating base oils known in the art can be used in combination with the eutectic mixture in a lubricant oil composition.
  • lubricating base oils that are useful in the present disclosure are natural oils, mineral oils and synthetic oils, and unconventional oils (or mixtures thereof) can be used unrefined, refined, or re-refined (the latter is also known as reclaimed or reprocessed oil).
  • Unrefined oils are those obtained directly from a natural or synthetic source and used without added purification. These include shale oil obtained directly from retorting operations, petroleum oil obtained directly from primary distillation, and ester oil obtained directly from an esterification process.
  • Refined oils are similar to the oils discussed for unrefined oils except refined oils are subjected to one or more purification steps to improve at least one lubricating oil property.
  • One skilled in the art is familiar with many purification processes. These processes include solvent extraction, secondary distillation, acid extraction, base extraction, filtration, and percolation.
  • Re-refined oils are obtained by processes analogous to refined oils but using an oil that has been previously used as a feed stock. Groups I, II, III, IV and V are broad base oil stock categories developed and defined by the American Petroleum Institute (API Publication 1509; www.API.org) to create guidelines for lubricant base oils.
  • Group I base stocks have a VI in the range from 80 to 120 and contain greater than 0.03% sulfur and/or less than 90% saturates.
  • Group II base stocks have a VI in the range from 80 to 120, and contain less than or equal to 0.03% sulfur and greater than or equal to 90% saturates.
  • Group III stocks have a VI greater than 120 and contain less than or equal to 0.03% sulfur and greater than 90% saturates.
  • Group IV includes PAOs.
  • Group V base stock includes base stocks not included in Groups I-IV.
  • Natural oils include animal oils, vegetable oils (castor oil and lard oil, for example), and mineral oils. Animal and vegetable oils possessing favorable thermal oxidative stability can be used. Of the natural oils, mineral oils are preferred. Mineral oils vary widely as to their crude source, for example, as to whether they are paraffinic, naphthenic, or mixed paraffinic-naphthenic. Oils derived from coal or shale are also useful. Natural oils vary also as to the method used for their production and purification, for example, their distillation range and whether they are straight run or cracked, hydrorefined, or solvent extracted.
  • Group II and/or Group III hydroprocessed or hydrocracked base stocks including synthetic oils such as alkyl aromatics and synthetic esters are also well known base stock oils.
  • Synthetic oils include hydrocarbon oil.
  • Hydrocarbon oils include oils such as polymerized and interpolymerized olefins (polybutylenes, poly propylenes, propylene isobutylene copolymers, ethylene-olefin copolymers, and ethylene-alpha-olefin copolymers, for example).
  • PAO base stocks are commonly used synthetic hydrocarbon oil.
  • PAOs derived from Cs, Cio, C12, C14 olefins or mixtures thereof may be utilized. See U.S. Pat. Nos. 4,956,122; 4,827,064; and 4,827,073.
  • the number of average molecular weights of the PAOs can vary from roughly 250 to 10,000, although PAO's may be made in KV100 as high as 1,000 cSt.
  • the PAOs are typically comprised of relatively low molecular weight hydrogenated polymers or oligomers of alpha-olefins which include, but are not limited to, C2 to approximately C32 alpha-olefins with the C8 to Ci6 alpha-olefins, such as 1-octene, 1-decene, 1 -dodecene and the like, being preferred.
  • the preferred polyalpha-olefins are poly-l-octene, poly-l-decene and poly-1- dodecene and mixtures thereof and mixed olefin-derived polyolefins.
  • the dimers of higher olefins in the range of C M to Ci8 may be used to provide low viscosity base stocks of acceptably low volatility.
  • the PAOs may be predominantly trimers and tetramers of the starting olefins, with minor amounts of the higher oligomers, having a viscosity range of 1.5 to 12 cSt.
  • PAO fluids of particular use may include 3.0 cSt, 3.4 cSt, and/or 3.6 cSt and combinations thereof. Mixtures of PAO fluids having a viscosity range of 1.5 to approximately 150 cSt or more may be used if desired.
  • the PAO fluids may be conveniently made by the polymerization of an alpha- olefin in the presence of a polymerization catalyst such as the Friedel-Crafts catalysts including, for example, aluminum trichloride, boron trifluoride or complexes of boron trifluoride with water, alcohols such as ethanol, propanol or butanol, carboxylic acids or esters such as ethyl acetate or ethyl propionate.
  • a polymerization catalyst such as the Friedel-Crafts catalysts including, for example, aluminum trichloride, boron trifluoride or complexes of boron trifluoride with water, alcohols such as ethanol, propanol or butanol, carboxylic acids or esters such as ethyl acetate or ethyl propionate.
  • a polymerization catalyst such as the Friedel-Crafts catalysts including, for example, aluminum trichloride,
  • Other useful lubricant oil base stocks include wax isomerate base stocks and base oils, comprising hydroisomerized waxy stocks (e.g. waxy stocks such as gas oils, slack waxes, fuels hydrocracker bottoms, etc.), hydroisomerized Fischer-Tropsch waxes, Gas-to- Liquids (GTL) base stocks and base oils, and other wax isomerate hydroisomerized base stocks and base oils, or mixtures thereof.
  • hydroisomerized waxy stocks e.g. waxy stocks such as gas oils, slack waxes, fuels hydrocracker bottoms, etc.
  • hydroisomerized Fischer-Tropsch waxes e.g. waxy stocks such as gas oils, slack waxes, fuels hydrocracker bottoms, etc.
  • Fischer-Tropsch waxes the high boiling point residues of Fischer-Tropsch synthesis, are highly paraffinic hydrocarbons with very low sulfur content.
  • the hydroprocessing used for the production of such base stocks may use an amorphous hydrocracking/hydroisomerization catalyst, such as one of the specialized lube hydrocracking (LHDC) catalysts or a crystalline hydrocracking/hydroisomerization catalyst, preferably a zeolitic catalyst.
  • an amorphous hydrocracking/hydroisomerization catalyst such as one of the specialized lube hydrocracking (LHDC) catalysts or a crystalline hydrocracking/hydroisomerization catalyst, preferably a zeolitic catalyst.
  • LHDC specialized lube hydrocracking
  • a zeolitic catalyst preferably ZSM-48 as described in U.S. Pat. No. 5,075,269, the disclosure of which is incorporated herein by reference in its entirety.
  • Processes for making hydrocracked/hydroisomerized distillates and hydrocracked/hydroisomerized waxes are described, for example, in U.S. Pat. Nos.
  • Gas-to-Liquids (GTL) base oils, Fischer-Tropsch wax derived base oils, and other wax-derived hydroisomerized (wax isomerate) base oils be advantageously used in the instant disclosure, and may have useful KVlOO in the range from 3 to 50 cSt, preferably from 3 to 30 cSt, more preferably from 3.5 to 25 cSt, as exemplified by GTL 4 with a KVlOO of approximately 4.0 cSt a VI of approximately 141.
  • Gas-to-Liquids (GTL) base oils may have useful pour points of -20°C or lower, and under some conditions may have advantageous pour points of -25°C or lower, with useful pour points of -30°C to -40°C or lower.
  • Useful compositions of Gas-to-Liquids (GTL) base oils, Fischer-Tropsch wax derived base oils, and wax-derived hydroisomerized base oils are recited in U.S. Pat. Nos. 6,080,301; 6,090,989, and 6,165,949 for example, and are incorporated herein in their entirety by reference.
  • the hydrocarbyl aromatics can be used as a base oil or base oil component and can be any hydrocarbyl molecule that contains at least 5% of its weight derived from an aromatic moiety such as a benzenoid moiety or naphthenoid moiety, or their derivatives.
  • These hydrocarbyl aromatics include alkyl benzenes, alkyl naphthalenes, alkyl diphenyl oxides, alkyl naphthols, alkyl diphenyl sulfides, alkylated bis-phenol A, alkylated thiodiphenol, and the like.
  • the aromatic can be mono-alkylated, dialkylated, polyalkylated, and the like.
  • the aromatic can be mono-or poly-functionalized.
  • the hydrocarbyl groups can also be comprised of mixtures of alkyl groups, alkenyl groups, alkynyl, cycloalkyl groups, cycloalkenyl groups and other related hydrocarbyl groups.
  • the hydrocarbyl groups can range from Ce up to Ceo with a range of Cs to C20 often being preferred. A mixture of hydrocarbyl groups are often preferred, and up to three such substituents may be present.
  • the hydrocarbyl group can optionally contain sulfur, oxygen, and/or nitrogen containing substituents.
  • the aromatic group can also be derived from natural (petroleum) sources, provided at least (roughly) 5% of the molecule is comprised of an above-type aromatic moiety.
  • KVlOO of approximately 3 to 50 cSt are preferred, with KVlOO of approximately 3.4 to 20 cSt often being more preferred for the hydrocarbyl aromatic component.
  • an alkyl naphthalene where the alkyl group is primarily comprised of 1-hexadecene is used.
  • Other alkylates of aromatics can be advantageously used.
  • Naphthalene or methyl naphthalene, for example, can be alkylated with olefins such as octene, decene, dodecene, tetradecene or higher, mixtures of similar olefins, and the like.
  • Useful concentrations of hydrocarbyl aromatic in a lubricant oil composition can be 2% to 25%, preferably 4% to 20%, and more preferably 4% to 15%, depending on the application.
  • Alkylated aromatics such as the hydrocarbyl aromatics of the present disclosure may be produced by well-known Friedel-Crafts alkylation of aromatic compounds. See Friedel-Crafts and Related Reactions, Olah, G. A. (ed.), Inter-science Publishers, New York, 1963.
  • an aromatic compound such as benzene or naphthalene
  • an olefin, alkyl halide or alcohol in the presence of a Friedel-Crafts catalyst. See Friedel- Crafts and Related Reactions, Vol. 2, part 1, chapters 14, 17, and 18, See Olah, G. A. (ed.), Inter-science Publishers, N.Y., 1964.
  • catalysts are known to one skilled in the art.
  • the choice of catalyst depends on the reactivity of the starting materials and product quality requirements.
  • strong acids such as AlCh, BF3, or HF may be used.
  • milder catalysts such as FeCh or SnC are preferred.
  • Newer alkylation technology uses zeolites or solid super acids.
  • Esters comprise a useful base stock. Additive solvency and seal compatibility characteristics may be secured by the use of esters such as the esters of dibasic acids with monoalkanols and the polyol esters of mono-carboxylic acids.
  • Esters of the former type include, for example, the esters of dicarboxylic acids such as phthalic acid, succinic acid, alkyl succinic acid, alkenyl succinic acid, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkyl malonic acid, alkenyl malonic acid, etc., with a variety of alcohols such as butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, etc.
  • dicarboxylic acids such as phthalic acid, succinic acid, alkyl succinic acid, alkenyl succinic acid, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkyl malonic acid, alkenyl malonic acid, etc
  • esters include dibutyl adipate, di(2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, etc.
  • Particularly useful synthetic esters are those which are obtained by reacting one or more polyhydric alcohols, preferably the hindered polyols (such as the neopentyl polyols, e.g., neopentyl glycol, trimethylol ethane, 2-methyl-2-propyl-l,3-propanediol, trimethylol propane, pentaerythritol and dipentaerythritol) with alkanoic acids containing at least 4 carbon atoms, preferably Cs to C30 acids such as saturated straight chain fatty acids including caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid, and behenic acid, or the corresponding branched chain fatty acids or unsaturated fatty acids such as oleic acid, or mixtures of any of these materials.
  • the hindered polyols such as the neopentyl polyols
  • Suitable synthetic ester components include the esters of trimethylol propane, trimethylol butane, trimethylol ethane, pentaerythritol and/or dipentaerythritol with one or more monocarboxylic acids containing from 5 to 10 carbon atoms. These esters are widely available commercially, for example, the Mobil P-41 and P-51 esters of ExxonMobil Chemical Company.
  • esters derived from renewable material such as coconut, palm, rapeseed, soy, sunflower and the like. These esters may be monoesters, di-esters, polyol esters, complex esters, or mixtures thereof. These esters are widely available commercially, for example, the Mobil P-51 ester of ExxonMobil Chemical Company.
  • Engine oil formulations containing renewable esters are included in this disclosure.
  • the renewable content of the ester is typically greater than 70 wt%, preferably more than 80 wt% and most preferably more than 90 wt%.
  • Other useful fluids of lubricating viscosity include non-conventional or unconventional base stocks that have been processed, preferably catalytically, or synthesized to provide high performance lubrication characteristics.
  • Non-conventional or unconventional base stocks ase oils include one or more of a mixture of base stock(s) derived from one or more Gas-to-Liquids (GTL) materials, as well as isomerate/isodewaxate base stock(s) derived from natural wax or waxy feeds, mineral and or non-mineral oil waxy feed stocks such as slack waxes, natural waxes, and waxy stocks such as gas oils, waxy fuels hydrocracker bottoms, waxy raffinate, hydrocrackate, thermal crackates, or other mineral, mineral oil, or even non-petroleum oil derived waxy materials such as waxy materials received from coal liquefaction or shale oil, and mixtures of such base stocks.
  • GTL Gas-to-Liquids
  • GTL materials are materials that are derived via one or more synthesis, combination, transformation, rearrangement, and/or degradation/deconstructive processes from gaseous carbon-containing compounds, hydrogen-containing compounds and/or elements as feed stocks such as hydrogen, carbon dioxide, carbon monoxide, water, methane, ethane, ethylene, acetylene, propane, propylene, propyne, butane, butylenes, and butynes.
  • GTL base stocks and/or base oils are GTL materials of lubricating viscosity that are generally derived from hydrocarbons; for example, waxy synthesized hydrocarbons, that are themselves derived from simpler gaseous carbon-containing compounds, hydrogen- containing compounds and/or elements as feed stocks.
  • GTL base stock(s) and/or base oil(s) include oils boiling in the lube oil boiling range (1) separated/fractionated from synthesized GTL materials such as, for example, by distillation and subsequently subjected to a final wax processing step which involves either or both of a catalytic dewaxing process, or a solvent dewaxing process, to produce lube oils of reduced/low pour point; (2) synthesized wax isomerates, comprising, for example, hydrodewaxed or hydroisomerized cat and/or solvent dewaxed synthesized wax or waxy hydrocarbons; and (3) hydrodewaxed or hydroisomerized cat and/or solvent dewaxed Fischer-Tropsch (F-T) material (i.e., hydrocarbons, waxy hydrocarbons, waxes and possible analogous oxygenates); preferably hydrodewaxed or hydroisomerized/followed by cat and/or solvent dewaxing dewaxed F-T waxy hydrocarbons, or hydrodewaxe
  • GTL base stock(s) and/or base oil(s) derived from GTL materials are characterized typically as having a KVlOO in the range from 2 mm 2 /s to 50 mm 2 /s. They are further characterized typically as having pour points of -5°C to -40°C or lower. They are also characterized typically as having viscosity indices of 80 to 140 or greater.
  • the GTL base stock(s) and/or base oil(s) are typically highly paraffinic (>90% saturates), and may contain mixtures of monocycloparaffins and multicycloparaffins in combination with non-cyclic isoparaffins.
  • the ratio of the naphthenic (i.e., cycloparaffin) content in such combinations varies with the catalyst and temperature used.
  • GTL base stock(s) and/or base oil(s) typically have very low sulfur and nitrogen content, generally containing less than 10 ppm, and more typically less than 5 ppm of each of these elements.
  • the sulfur and nitrogen content of GTL base stock(s) and/or base oil(s) obtained from F-T material, especially F-T wax, is essentially nil.
  • the absence of phosphorous and aromatics make this materially especially suitable for the formulation of low SAP products.
  • GTL base stock and/or base oil and/or wax isomerate base stock and/or base oil is to be understood as embracing individual fractions of such materials of wide viscosity range as recovered in the production process, mixtures of two or more of such fractions, as well as mixtures of one or two or more low viscosity fractions with one, two or more higher viscosity fractions to produce a blend wherein the blend exhibits a target kinematic viscosity.
  • the GTL material, from which the GTL base stock(s) and/or base oil(s) is/are derived is preferably an F-T material (i.e., hydrocarbons, waxy hydrocarbons, wax).
  • Base oils for use in the formulated lubricating oils useful in the present disclosure are any of the variety of oils corresponding to API Group I, Group II, Group III, Group IV, and Group V oils and mixtures thereof, preferably API Group II, Group III, Group IV, and Group V oils and mixtures thereof, more preferably the Group III to Group V base oils due to their exceptional volatility, stability, viscometric and cleanliness features.
  • Minor quantities of Group I stock such as the amount used to dilute additives for blending into formulated lube oil products, can be tolerated but should be kept to a minimum, i.e., amounts only associated with their use as diluent/carrier oil for additives used on an "as-received" basis.
  • Even in regard to the Group II stocks it is preferred that the Group II stock be in the higher quality range associated with that stock, i.e., a Group II stock having a VI in the range of 100 to 120.
  • the base oil constitutes the major component of the engine oil lubricant composition of the present disclosure and typically is present in an amount ranging from -50 to -99 wt%, preferably from 70 to 95 wt% (or 70 to 99 wt%), and more preferably from 80 to 95 wt% (or 80 to 99 wt%), based on the total weight of the composition.
  • the base oil may be selected from any of the synthetic or natural oils typically used as crankcase lubricating oils for spark-ignited and compression-ignited engines.
  • the base oil conveniently has a KV100 in the range from 2.5 to 12 cSt, preferably form 2.5 to 9 cSt. Mixtures of synthetic and natural base oils may be used if desired. Bi-modal mixtures of Group I, II, III, IV, and/or V base stocks may be used if desired.
  • a formulated lubricating oil may additionally contain one or more of the other commonly used lubricating oil performance additives including but not limited to detergents, anti-wear additives, dispersants, viscosity modifiers, corrosion inhibitors, rust inhibitors, metal deactivators, extreme pressure additives, anti-seizure agents, wax modifiers, viscosity modifiers, fluid-loss additives, seal compatibility agents, lubricity agents, anti-staining agents, chromophoric agents, defoamants, demulsifiers, emulsifiers, densifiers, wetting agents, gelling agents, tackiness agents, colorants, and others.
  • the other commonly used lubricating oil performance additives including but not limited to detergents, anti-wear additives, dispersants, viscosity modifiers, corrosion inhibitors, rust inhibitors, metal deactivators, extreme pressure additives, anti-seizure agents, wax modifiers, viscosity modifiers, fluid-loss additives, seal
  • the additives useful in this disclosure do not have to be soluble in the lubricating oils.
  • Insoluble additives such as zinc stearate in oil can be dispersed in the lubricating oils of this disclosure.
  • Typical amounts of such additives useful in the present disclosure are shown in Table 1 below.
  • the additives are shipped from the additive manufacturer as a concentrate, containing one or more additives together, with a certain amount of base oil diluents. Accordingly, the weight amounts in the table below, as well as other amounts mentioned herein, are directed to the amount of active ingredient (that is the non-diluent portion of the ingredient). The weight percentages (wt%) indicated below is based on the total weight of the lubricating oil composition, unless specified to the contrary.
  • additives can be commercially available. These additives may be added independently but are usually pre-combined in packages which can be obtained from suppliers of lubricant oil additives. Additive packages with a variety of ingredients, proportions and characteristics are available and selection of the appropriate package will take the requisite use of the ultimate composition into account.
  • compositions described herein examples include, but are not limited to, analytical gas chromatography (GC), Fourier transform infrared (FTIR) spectroscopy, infrared (IR) spectroscopy, nuclear magnetic resonance (NMR), thermogravimetric analysis (TGA), inductively coupled plasma mass spectrometry, differential scanning calorimetry (DSC), volatility and viscosity measurements.
  • GC analytical gas chromatography
  • FTIR Fourier transform infrared
  • IR infrared
  • NMR nuclear magnetic resonance
  • TGA thermogravimetric analysis
  • DSC differential scanning calorimetry
  • compositions and the lubricant oils of this disclosure are useful in a variety of applications.
  • Illustrative applications include, but are not limited to: performance additives, separation fluids, analytics, syntheses, electrochemistry, engineering fluids, material syntheses, and the like.
  • Illustrative performance additive applications include, for example, plasticizers, dispersing agents, compatibilizers, solubilizers, antistatic agents, gas hydrate inhibitors, enhance oil recovery, heavy hydrocarbon viscosity reducers, and the like.
  • Illustrative separation applications include, for example, gas absorption/storage, extraction, carbon capture, ion containing polymer membranes, and the like.
  • Illustrative analytic applications include, for example, gas chromatography columns, stationary phase for high pressure liquid chromatography, matrices for mass spectra, and the like.
  • Illustrative synthesis applications include, for example, solvents, catalysis, biphasic reactions, manufacture of nanomaterials, and the like.
  • Illustrative electrochemistry applications include, for example, electrolyte in batteries, electrolyte in sensors, metal plating, and the like.
  • Illustrative engineering fluid applications include, for example, lubricants, thermal fluids, energy storage fluids, heat transfer fluids, and the like.
  • Illustrative material synthesis applications include, for example, templates (also called structure-directing agents) in material synthesis and design of novel structures, and the like.
  • CC stands for choline chloride (MW: 139.62, melting point (“mp"): 302°C)
  • EG stands for ethylene glycol (HO-CH2-CH2-OH) (MW 62.07, mp: -13°C).
  • Table 2 shows compositions and properties for a series of inventive LTTM fluids and comparative materials.
  • the molar ratio is that of the first component to the second component.
  • a LTTM was not formed at the specified molar ratio between the first and the second component.
  • the composition further comprises water at about 2 wt%, based on the total weight of the composition of the LTTM. Details of the LTTM fluids in Table 2 are further described in the following examples.
  • a commercial polyalpha-olefin base stock (PA05) is provided as a reference material for the LTTMs with similar KV40, KV100, and VI. Table 2
  • the general procedure for forming LTTMs included mixing the two starting materials in a round-bottom flask using a stirring rod. The mixing was optionally done under nitrogen atmosphere, such as for any starting materials that were hygroscopic. The mixtures were typically heated to 70-100°C until all solids disappeared to make a homogenous solution. The liquid mixture was then cooled to room temperature. All DSC diagrams were obtained at a heating rate of 10°C per minute.
  • Examples 1 - 5 correspond to LTTMs formed from CC and EG in molar ratios of 1 :2, 1 :4, 1 :5, 1 :6, and 1 :9, respectively. It was observed that an LTTM did not form when CC and EG were mixed in a 1 : 1 ratio.
  • the CC/EG LTTMs generally showed high VI values, and in particular, Example 1 shows a VI in the range from 170 to 180, which is exceptionally high. This high VI value is exceptionally high when considering the viscosity of the LTTM in Example 1.
  • Example 15 shows an example of a commercial polyalpha-olefin synthetic base stock having a VI in the range from 130 to 140.
  • the LTTMs of Examples 1 to 5 all had KVlOO in the range from 2.0 to 6.0 cSt and VPs of at least 60.
  • the glass transition temperatures were lower than -110°C.
  • LTTMs To form the LTTMs, 40 mmol (5.58 grams) CC and EG (80 mmol (4.97 grams), 160 mmol (9.94 grams), 200 mmol (12.43 grams), 240 mmol (14.91 grams), and 360 mmol (22.37 grams), respectively) were added to a 50 mL round-bottom flask. The components were heated to 70-80°C while stirring until a homogenous liquid was formed.
  • FIG. 1 shows portions of NMR spectra from the LTTM formed from CC and EG at a molar ratio of the 1 :2 (Example 1).
  • the NMR spectra show the presence of CC and EG, as well as the presence of hydrogen bonding between the components.
  • the downshift of EG peaks (a ) indicates the effect due to hydrogen bond donation.
  • FIG. 2 shows the DSC diagram of the LTTM of Example 1, which indicated a T of -117.19°C.
  • FIG. 3 shows the DSC diagram of the LTTM of Example 3, which indicated a T g of -119.59°C.
  • FIG. 4 shows the DSC diagram of the LTTM of Example 5, which indicated a T g of -118.99°C.
  • some additional peaks are present, including a peak corresponding to a melting point. Without being bound by any particular theory, it is believed that the additional peaks correspond to a non-participating component.
  • Example 6 corresponds to an LTTM formed from CC and propylene glycol (HO- CH2CH2CH2OH) (MW 76.09, mp: -59°C) in a molar ratio of 1 :4.
  • the CC/propylene glycol LTTM showed a VI of at least 70 and a KVlOO in the range from 4.0 to 5.0 cSt.
  • the glass transition temperature was lower than -100°C, as shown in the DSC diagram in FIG. 5.
  • LTTM LTTM
  • 40 mmol (5.58 grams) of CC and 160 mmol (12.17 grams) of propylene glycol were added to a 50 mL round-bottom flask.
  • the components were heated to 70-80°C while stirring until a homogenous liquid was formed.
  • Example 7 corresponds to an LTTM formed from CC and 1,2-hexanediol in a molar ratio of 1 :6.
  • the CC/l,2-hexanediol LTTM showed a VI of at least 90 and a KVlOO in the range from 2.0 to 3.0 cSt.
  • Example 8 corresponds to an LTTM formed from CC and glycerol (MW 92.09, mp: 17.8°C) in a molar ratio of 1 :2.
  • the glass transition temperature was lower than -90°C, as shown in the DSC diagram in FIG. 6.
  • 40 mmol of CC and 80 mmol (7.37 grams) of glycerol were added to a 50 mL round-bottom flask. The components were heated to 70-80°C while stirring until a homogenous liquid was formed.
  • Example 9 3 ml of ethanol was also added to the flask. Instead of heating, the components were stirred without heating for 2 hours. The solvent was then removed by a rotary evaporator. In Example 9, ethanol was used as a solvent during formation of the LTTM.
  • the CC/glycerol LTTMs showed a VI of at least 90 and a KV100 in the range of 10 to 15 cSt.
  • the DSC diagram of this material (not shown) is very similar to that in FIG. 6 in shape and Tg, indicating that the LTTM prepared with and without an ethanol solvent were very similar.
  • Example 10 corresponds to an LTTM formed from CC and catechol (MW 110.11, mp: 100°C) in a molar ratio of 1 : 1.
  • An LTTM was not formed when a molar ratio of 1 :2 was used.
  • the CC/catechol LTTM showed a VI of at least 60 and a KV100 of from 20 to 30 cSt.
  • the glass transition temperature was lower than -70°C, as shown in the DSC diagram in FIG. 7.
  • the DSC diagram showed multiple peaks corresponding to both a glass transition and a melting phase transition.
  • the DSC diagram in FIG. 7 included some other additional features, which are believed to correspond to a non-participating individual component.
  • Example 12 corresponds to an LTTM formed from CC and resorcinol (MW 110.11, mp: 109°C) in a molar ratio of 1 :2.
  • An LTTM was not formed when a molar ratio of 1 : 1 was used, which corresponds to Example 11 in Table 2.
  • the CC/resorcinol LTTM showed a VI of at least 80 and a KV100 in the range from 20 to 30 cSt.
  • the glass transition temperature was lower than -70°C, as shown in the DSC diagram in FIG. 8. Considering the melting point of resorcinol at 109°C, this glass transition temperature of the mixture is exceptionally low.
  • Example 13 a LTTM based on a 1 :2 molar ratio of CC and EG was formed by adding 760 mmol of CC (106.1 grams) and 1520 mmol of EG (94.35 grams) to a 500 mL round-bottom flask. The components were heated to 70-80°C while stirring until a homogenous liquid was formed. This resulted in an LTTM with properties similar to Example 1.
  • Example 14 After making the LTTM in Example 13, 0.02 g of water was added to 1.0 g of the Example 13 LTTM. The resulting LTTM containing 2 wt% water is shown as Example 14. Although the viscosity is modestly reduced, the LTTM otherwise retains its unexpected properties.
  • Example 16 (not shown in Table 2), a still larger scale batch of LTTM based on a 1 :2 molar ratio of CC and EG was made by adding 106.1 g of CC (760.0 mmol) and 94.35 g of EG (1520.0 mmol) into a 500 mL round bottom flask. The components were heated at 70-80°C while stirring until a homogenous liquid was formed. Similar to Examples 1 and 13, the resulting LTTM had a VI of 177, a KV 100 of 5.4 cSt, and a KV40 of 23.5 cSt.
  • FIG. 9 shows traction curves as a function of slide to roll ratio (SRR, expressed in terms of percentage of slide relative to roll) at a series of temperatures.
  • SRR slide to roll ratio
  • the traction test was carried out at a pressure of 0.75 GPa, temperatures of 40, 60, 80, 100, and 120 °C, respectively, at a rolling speed of 2 m/s rolling speed. Results shown as traction coefficient as a function of SRR(%) are provided in FIG. 9.
  • the LTTM fluid of Example 16 showed an unexpectedly low traction coefficient at the measured temperatures. As shown in FIG. 9, the traction coefficient for the LTTM of Example 16 was consistently lower than 0.008 at 40, 60, 80 and even 100°C. The low traction coefficient at such large temperature span renders the fluid particularly useful in lubricating oil compositions, which can translate into substantial energy savings during operation of equipment lubricated by such lubricants.
  • Example 17 Preparation of LTTMs from betaine and EG
  • Example 17 corresponds to an LTTM formed from betaine (MW: 117.15, mp: ⁇ 293°C) and EG in a molar ratio of 1 :4.
  • An LTTM was not formed when a molar ratio of 1 : 1 or 1 :2 was used. Without being bound by any particular theory, this may be due to the higher polarity of betaine relative to CC.
  • the betain/EG LTTM showed a VI of 95 (i.e., at least 90) and a KV100 of 4 to 6 cSt.
  • Examples 18 and 19 correspond to an ionic liquid and a comparative LTTM, respectively, both formed from CC and lactic acid.
  • FIG. 10 schematically shows the components interacting with each other in an ionic liquid formed from lactic acid (MW: 90.08, mp: 16.8°C, boiling point ("bp"): 122°C) and CC
  • FIG. 11 shows the components interacting with each other in the corresponding LTTM at a 1 :2 molar ratio of lactic acid and CC.
  • the LTTM in Example 19 is comparative in that the second component (lactic acid) contains only one alcoholic hydroxyl group per molecule. While lactic acid comprises two hydroxyl groups in each molecule, the other one is not an alcoholic hydroxyl group insofar as it forms part of a carboxylic group.
  • the ionic liquid was formed by conventional methods.
  • For the LTTM 20.0 mmol (2.79 grams) of CC and 40 mmol (3.6 grams) of lactic acid were added to a round-bottom flask and heated to 70-80°C while stirring until a homogenous liquid was formed. The mixture was then cooled to room temperature.
  • FTIR was used to characterize the ionic liquid, the LTTM, and the separate lactic acid component. The FTIR spectra are shown in FIG. 12.
  • the LTTM shows only an acid peak at 1710 cm “1 , which is believed to correspond to the carbonyl peak for the acid group in the lactic acid, while the ionic liquid only shows the lactate peak from choline lactate at 1550 cm "1 for the carbonyl group.
  • FIG. 13 shows the DSC diagrams of the ionic liquid of comparative Example 18 and the LTTM of comparative Example 19.
  • the ionic liquid had a Tg of -68.6°C (curve on the right side at temperatures below about -70°C), while the LTTM had a Tg of -86.6°C (curve on the left side at temperatures below about -70°C).
  • the ionic liquid had a VI of 96, a KVlOO of 32.9 cSt, and a KV40 of 513.74.
  • the LTTM had a VI of 105.7, a KV100 of 9.6 cSt, and a KV40 of 74.8 cSt. While the comparative LTTM of Example 19 shows better performance than the ionic liquid in comparative Example 18, it nonetheless does not have performance as high as the LTTMs formed from ethylene glycol and CC in Examples 1, 13, and 16, above.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

L'invention concerne des mélanges à température de transition basse comprenant un mélange eutectique d'une amine quaternaire et d'un polyol, tel que le glycol. Les mélanges à température de transition basse peuvent présenter diverses propriétés intéressantes, telles qu'un indice de viscosité très avantageux, des températures de transition vitreuse basses et/ou des viscosités cinématiques élevées par rapport au poids moléculaire des composants des mélanges. Les mélanges peuvent être avantageusement utilisés en tant qu'huiles de base associées dans des compositions d'huile lubrifiante.
PCT/US2018/015143 2017-02-06 2018-01-25 Mélanges à température de transition basse et huiles lubrifiantes contenant ceux-ci WO2018144301A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201762455160P 2017-02-06 2017-02-06
US62/455,160 2017-02-06
EP17161742.6 2017-03-20
EP17161742 2017-03-20

Publications (1)

Publication Number Publication Date
WO2018144301A1 true WO2018144301A1 (fr) 2018-08-09

Family

ID=58387715

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2018/015143 WO2018144301A1 (fr) 2017-02-06 2018-01-25 Mélanges à température de transition basse et huiles lubrifiantes contenant ceux-ci

Country Status (1)

Country Link
WO (1) WO2018144301A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114787248A (zh) * 2019-09-30 2022-07-22 日清纺控股株式会社 复合材料
CN114806673A (zh) * 2022-04-28 2022-07-29 江苏大学 胆碱型类离子液体作为润滑剂的应用及润滑剂组合物
CN114854474A (zh) * 2022-04-25 2022-08-05 镇江四联机电科技有限公司 一种低摩擦系数抗磨液压油

Citations (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2817693A (en) 1954-03-29 1957-12-24 Shell Dev Production of oils from waxes
US3382291A (en) 1965-04-23 1968-05-07 Mobil Oil Corp Polymerization of olefins with bf3
US3742082A (en) 1971-11-18 1973-06-26 Mobil Oil Corp Dimerization of olefins with boron trifluoride
US3769363A (en) 1972-03-13 1973-10-30 Mobil Oil Corp Oligomerization of olefins with boron trifluoride
GB1350257A (en) 1970-06-05 1974-04-18 Shell Int Research Process for the preparation of a lubricating oil
US3876720A (en) 1972-07-24 1975-04-08 Gulf Research Development Co Internal olefin
GB1390359A (en) 1971-05-13 1975-04-09 Shell Int Research Process for the preparation of lubricating oil with high viscosity index
GB1429494A (en) 1972-04-06 1976-03-24 Shell Int Research Process for the preparation of a lubricating oil
GB1440230A (en) 1972-08-04 1976-06-23 Shell Int Research Process for the preparation of lubricating oils
US4149178A (en) 1976-10-05 1979-04-10 American Technology Corporation Pattern generating system and method
US4218330A (en) 1978-06-26 1980-08-19 Ethyl Corporation Lubricant
US4239930A (en) 1979-05-17 1980-12-16 Pearsall Chemical Company Continuous oligomerization process
US4367352A (en) 1980-12-22 1983-01-04 Texaco Inc. Oligomerized olefins for lubricant stock
US4413156A (en) 1982-04-26 1983-11-01 Texaco Inc. Manufacture of synthetic lubricant additives from low molecular weight olefins using boron trifluoride catalysts
US4434408A (en) 1980-03-11 1984-02-28 Sony Corporation Oscillator having capacitor charging and discharging controlled by non-saturating switches
US4594172A (en) 1984-04-18 1986-06-10 Shell Oil Company Process for the preparation of hydrocarbons
US4827064A (en) 1986-12-24 1989-05-02 Mobil Oil Corporation High viscosity index synthetic lubricant compositions
US4827073A (en) 1988-01-22 1989-05-02 Mobil Oil Corporation Process for manufacturing olefinic oligomers having lubricating properties
US4897178A (en) 1983-05-02 1990-01-30 Uop Hydrocracking catalyst and hydrocracking process
US4910355A (en) 1988-11-02 1990-03-20 Ethyl Corporation Olefin oligomer functional fluid using internal olefins
US4921594A (en) 1985-06-28 1990-05-01 Chevron Research Company Production of low pour point lubricating oils
US4943672A (en) 1987-12-18 1990-07-24 Exxon Research And Engineering Company Process for the hydroisomerization of Fischer-Tropsch wax to produce lubricating oil (OP-3403)
US4956122A (en) 1982-03-10 1990-09-11 Uniroyal Chemical Company, Inc. Lubricating composition
US4975177A (en) 1985-11-01 1990-12-04 Mobil Oil Corporation High viscosity index lubricants
US5068487A (en) 1990-07-19 1991-11-26 Ethyl Corporation Olefin oligomerization with BF3 alcohol alkoxylate co-catalysts
US5075269A (en) 1988-12-15 1991-12-24 Mobil Oil Corp. Production of high viscosity index lubricating oil stock
EP0464547A1 (fr) 1990-07-05 1992-01-08 Mobil Oil Corporation Production de lubrifiants à haute indice de viscosité
EP0464546A1 (fr) 1990-07-05 1992-01-08 Mobil Oil Corporation Production de lubrifiants à haut indice de viscosité
US6080301A (en) 1998-09-04 2000-06-27 Exxonmobil Research And Engineering Company Premium synthetic lubricant base stock having at least 95% non-cyclic isoparaffins
US6090989A (en) 1997-10-20 2000-07-18 Mobil Oil Corporation Isoparaffinic lube basestock compositions
US6165949A (en) 1998-09-04 2000-12-26 Exxon Research And Engineering Company Premium wear resistant lubricant
US7704930B2 (en) 2002-01-31 2010-04-27 Exxonmobil Research And Engineering Company Mixed TBN detergents and lubricating oil compositions containing such detergents
WO2015159070A1 (fr) * 2014-04-14 2015-10-22 University Of Leicester Tannage de substrats à l'aide de liquides ioniques
US20160122676A1 (en) 2014-11-03 2016-05-05 Exxonmobil Research And Engineering Company Low transition temperature mixtures or deep eutectic solvents and processes for preparation thereof
CN106474873A (zh) * 2016-11-16 2017-03-08 浙江大学 一种从含氨废气中吸收分离氨气的方法

Patent Citations (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2817693A (en) 1954-03-29 1957-12-24 Shell Dev Production of oils from waxes
US3382291A (en) 1965-04-23 1968-05-07 Mobil Oil Corp Polymerization of olefins with bf3
GB1350257A (en) 1970-06-05 1974-04-18 Shell Int Research Process for the preparation of a lubricating oil
GB1390359A (en) 1971-05-13 1975-04-09 Shell Int Research Process for the preparation of lubricating oil with high viscosity index
US3742082A (en) 1971-11-18 1973-06-26 Mobil Oil Corp Dimerization of olefins with boron trifluoride
US3769363A (en) 1972-03-13 1973-10-30 Mobil Oil Corp Oligomerization of olefins with boron trifluoride
GB1429494A (en) 1972-04-06 1976-03-24 Shell Int Research Process for the preparation of a lubricating oil
US3876720A (en) 1972-07-24 1975-04-08 Gulf Research Development Co Internal olefin
GB1440230A (en) 1972-08-04 1976-06-23 Shell Int Research Process for the preparation of lubricating oils
US4149178A (en) 1976-10-05 1979-04-10 American Technology Corporation Pattern generating system and method
US4218330A (en) 1978-06-26 1980-08-19 Ethyl Corporation Lubricant
US4239930A (en) 1979-05-17 1980-12-16 Pearsall Chemical Company Continuous oligomerization process
US4434408A (en) 1980-03-11 1984-02-28 Sony Corporation Oscillator having capacitor charging and discharging controlled by non-saturating switches
US4367352A (en) 1980-12-22 1983-01-04 Texaco Inc. Oligomerized olefins for lubricant stock
US4956122A (en) 1982-03-10 1990-09-11 Uniroyal Chemical Company, Inc. Lubricating composition
US4413156A (en) 1982-04-26 1983-11-01 Texaco Inc. Manufacture of synthetic lubricant additives from low molecular weight olefins using boron trifluoride catalysts
US4897178A (en) 1983-05-02 1990-01-30 Uop Hydrocracking catalyst and hydrocracking process
US4594172A (en) 1984-04-18 1986-06-10 Shell Oil Company Process for the preparation of hydrocarbons
US4921594A (en) 1985-06-28 1990-05-01 Chevron Research Company Production of low pour point lubricating oils
US4975177A (en) 1985-11-01 1990-12-04 Mobil Oil Corporation High viscosity index lubricants
US4827064A (en) 1986-12-24 1989-05-02 Mobil Oil Corporation High viscosity index synthetic lubricant compositions
US4943672A (en) 1987-12-18 1990-07-24 Exxon Research And Engineering Company Process for the hydroisomerization of Fischer-Tropsch wax to produce lubricating oil (OP-3403)
US4827073A (en) 1988-01-22 1989-05-02 Mobil Oil Corporation Process for manufacturing olefinic oligomers having lubricating properties
US4910355A (en) 1988-11-02 1990-03-20 Ethyl Corporation Olefin oligomer functional fluid using internal olefins
US5075269A (en) 1988-12-15 1991-12-24 Mobil Oil Corp. Production of high viscosity index lubricating oil stock
EP0464547A1 (fr) 1990-07-05 1992-01-08 Mobil Oil Corporation Production de lubrifiants à haute indice de viscosité
EP0464546A1 (fr) 1990-07-05 1992-01-08 Mobil Oil Corporation Production de lubrifiants à haut indice de viscosité
US5068487A (en) 1990-07-19 1991-11-26 Ethyl Corporation Olefin oligomerization with BF3 alcohol alkoxylate co-catalysts
US6090989A (en) 1997-10-20 2000-07-18 Mobil Oil Corporation Isoparaffinic lube basestock compositions
US6080301A (en) 1998-09-04 2000-06-27 Exxonmobil Research And Engineering Company Premium synthetic lubricant base stock having at least 95% non-cyclic isoparaffins
US6165949A (en) 1998-09-04 2000-12-26 Exxon Research And Engineering Company Premium wear resistant lubricant
US7704930B2 (en) 2002-01-31 2010-04-27 Exxonmobil Research And Engineering Company Mixed TBN detergents and lubricating oil compositions containing such detergents
WO2015159070A1 (fr) * 2014-04-14 2015-10-22 University Of Leicester Tannage de substrats à l'aide de liquides ioniques
US20160122676A1 (en) 2014-11-03 2016-05-05 Exxonmobil Research And Engineering Company Low transition temperature mixtures or deep eutectic solvents and processes for preparation thereof
WO2016073149A1 (fr) * 2014-11-03 2016-05-12 Exxonmobil Research And Engineering Company Mélanges à faible température de transition ou solvants eutectiques profonds et procédés pour leur préparation
CN106474873A (zh) * 2016-11-16 2017-03-08 浙江大学 一种从含氨废气中吸收分离氨气的方法

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
ANDREW P. ABBOTT ET AL: "Evaluating water miscible deep eutectic solvents (DESs) and ionic liquids as potential lubricants", GREEN CHEMISTRY, vol. 16, no. 9, 1 January 2014 (2014-01-01), GB, pages 4156 - 4161, XP055386348, ISSN: 1463-9262, DOI: 10.1039/C4GC00952E *
F.S. MJALLI ET AL: "Ethaline and Glyceline binary eutectic mixtures: characteristics and intermolecular interactions : Ethaline-Glyceline", ASIA-PACIFIC JOURNAL OF CHEMICAL ENGINEERING JANUARY/FEBRUARY 2007 JOHN WILEY AND SONS LTD; THE ATRIUM GB, vol. 12, no. 2, 7 February 2017 (2017-02-07), US, pages 313 - 320, XP055384146, ISSN: 1932-2135, DOI: 10.1002/apj.2074 *
OLAH, G. A.: "Friedel-Crafts and Related Reactions", 1963, INTER-SCIENCE PUBLISHERS
OLAH, G. A.: "Friedel-Crafts and Related Reactions", vol. 2, part 1 1964, INTER-SCIENCE PUBLISHERS, article "chapters 14, 17, and 18"

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114787248A (zh) * 2019-09-30 2022-07-22 日清纺控股株式会社 复合材料
CN114854474A (zh) * 2022-04-25 2022-08-05 镇江四联机电科技有限公司 一种低摩擦系数抗磨液压油
CN114806673A (zh) * 2022-04-28 2022-07-29 江苏大学 胆碱型类离子液体作为润滑剂的应用及润滑剂组合物
CN114806673B (zh) * 2022-04-28 2023-09-26 江苏大学 胆碱型类离子液体作为润滑剂的应用及润滑剂组合物

Similar Documents

Publication Publication Date Title
US8268760B2 (en) Method for reducing friction/wear of formulated lubricating oils by use of ionic liquids as anti-friction/anti-wear additives
EP2398880B1 (fr) Methode pour controler l'oxidation induce par h2o2 dans formulations lubrifies par utilisation de liquides ioniques comme additives
US8263536B2 (en) Method for the control of deposit formation in formulated lubricating oil by use of ionic liquids as additives
US10793801B2 (en) Low transition temperature mixtures and lubricating oils containing the same
US11066620B2 (en) Lubricant composition
US12215294B2 (en) Lubricant composition
US20150175923A1 (en) Method for improving engine fuel efficiency
JP2020511581A (ja) エンジン燃料効率及びエネルギー効率の改善方法
WO2018144301A1 (fr) Mélanges à température de transition basse et huiles lubrifiantes contenant ceux-ci
US8614174B2 (en) Lubricants having alkyl cyclohexyl 1,2-dicarboxylates
WO2018144166A1 (fr) Huile lubrifiante pour moteur et procédé d'amélioration du rendement de carburant de moteur
US20100216678A1 (en) Lubricant compositions containing glycerol tri-esters
WO2019126751A2 (fr) Additifs pour lubrifiants et leurs procédés d'utilisation
US9617494B2 (en) Method for improving deposit control
US10858610B2 (en) Cold cranking simulator viscosity boosting base stocks and lubricating oil formulations containing the same
US10876062B2 (en) Cold cranking simulator viscosity boosting base stocks and lubricating oil formulations containing the same
WO2018175047A1 (fr) Huiles de base augmentant la viscosité d'un simulateur de démarrage à froid et formulations d'huile lubrifiante les contenant
EP3601504A1 (fr) Huiles de base augmentant la viscosité d'un simulateur de démarrage à froid et formulations d'huile lubrifiante les contenant
US20180273875A1 (en) Cold Cranking Simulator Viscosity Boosting Base Stocks and Lubricating Oil Formulations Containing the Same
EP3601503A1 (fr) Huiles de base augmentant la viscosité d'un simulateur de démarrage à froid et formulations d'huile lubrifiante les contenant
WO2018175046A1 (fr) Huiles de base augmentant la viscosité d'un simulateur de démarrage à froid et formulations d'huile lubrifiante les contenant

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18703885

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 18703885

Country of ref document: EP

Kind code of ref document: A1

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载