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
  • 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
  • C10M105/32—Esters
  • C10M105/38—Esters of polyhydroxy compounds
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • 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
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
  • C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen 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
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
  • C10M2203/102—Aliphatic fractions
  • C10M2203/1025—Aliphatic fractions 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
  • C10M2207/28—Esters
  • C10M2207/283—Esters of polyhydroxy compounds
  • C10M2207/2835—Esters of polyhydroxy compounds 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
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/02—Pour-point; Viscosity index
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/04—Detergent property or dispersant property
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/08—Resistance to extreme temperature
• • 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
  • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
• • 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
  • C10N2030/64—Environmental friendly compositions
• • 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
  • C10N2030/74—Noack Volatility
• • 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 base oil or base oil blends comprising a diester with suitable properties to improve the cold flow properties and lower the volatility of a starting base oil or starting base oil blend.
• the present invention relates to a process for improving a starting base oil or starting base oil blend by replacing portions of a starting base oil or starting base oil blend with a diester with suitable properties to improve the cold flow properties and lower the volatility relative to the starting base oil or starting base oil blend.
• Esters have been used as lubricating oils for over 50 years. They are used in a variety of applications ranging from jet engines, refrigeration and motor oils. In fact, esters were the first synthetic crankcase motor oils in automotive applications. However, esters gave way to polyalphaolefins (PAOs) due to the lower cost of PAOs and their formulation similarities to mineral oils. In full synthetic motor oils, however, esters are almost always used in combination with PAOs to balance the effect on seals, additives solubility, volatility reduction, and energy efficiency improvement by enhanced lubricity. In this aspect, novel diester-based multi-grade engine oil compositions comprising PAOs have been described in commonly-assigned United States Patent Application Serial No. 12/548,191 ; filed August 26, 2009.
• Ester-based lubricants in general, have excellent lubrication properties due to the polarity of the ester molecules of which they are comprised.
• the polar ester groups of such molecules adhere to positively-charged metal surfaces creating protective films which slow down the wear and tear of the metal surfaces.
• Such lubricants are less volatile than the traditional lubricants and tend to have much higher flash points and much lower vapor pressures.
• Ester lubricants are excellent solvents and dispersants, and can readily solvate and disperse the degradation by-products of oils. Therefore, they greatly reduce sludge buildup.
• ester lubricants are stable to thermal and oxidative processes, the ester functionalities give microbes a handle to do their biodegrading more efficiently and more effectively than their mineral oil-based analogues. Therefore, there exists an opportunity to employ an alternative blending component that reduces volatility at a reduced cost and with other advantages not afforded with PAO.
• FT Fischer-Tropsch
• Novel diester-based lubricant compositions and their corresponding syntheses have been described in commonly-assigned United States Patent No. US 7,871,967 B2; issued January 18, 2011.
• the synthetic routes described in this patent application comprise and/or generally proceed through the following sequence of reaction steps: (1) epoxidation of an olefin to form an epoxide; (2) conversion of the epoxide to form a diol; and (3) esterification of the diol to form a diester.
• novel diester-based lubricant compositions and their corresponding syntheses have been described in commonly-assigned United States Patent No. US 7,867,959 B2; issued January 1 1, 201 1.
• the synthetic routes described in this patent application comprise and/or generally proceed through the following sequence of reaction steps: (1) epoxidation of an olefin to form an epoxide; (2) directly esterifying the epoxide with a carboxylic acid to form a diester species.
• the present invention is directed to a base oil blend comprising: a) a diester component, comprising a quantity of at least one diester species of Formula I:
• Ri, R 2 , R 3 and R4 are the same or independently selected from C2 to C 17 hydrocarbon groups; b) a second base oil, and wherein the second base oil is a Group I base oil, Group II base oil or Group III base oil.
• the present invention is directed to a process for improving cold flow properties and lowering Noack in a starting base oil or starting base oil blend, comprising: replacing between about 5 to 60 wt % of a starting base oil or starting base oil blend with an equal quantity of a base oil comprising: a) a diester component, comprising a quantity of at least one diester species of Formula I:
• Ri, R2, R3 and R4 are the same or independently selected from C2 to Ci 7 hydrocarbon groups, and wherein the process affords an upgraded base oil blend.
• Figure 1 is a chart illustrates the Noack and CCS Viscosity of the diesters of the present invention as compared to the current commercial esters as presented in Table 6 and other Group II and III bases oils.
• the present invention is directed to a base oil blend, comprising: a) a diester component, comprising a quantity of at least one diester species of Formula I, wherein Ri, R 2 , R3 and R4 are the same or independently selected from C2 to C17 hydrocarbon groups; b) a second base oil; and wherein the second base oil is a Group I base oil, Group II base oil or Group III base oil.
• the present invention is directed to a base oil blend, wherein the diester component comprises a mixture of isomers where Ri and R2 are different for each isomer.
• the present invention is directed to a base oil blend, further comprising, a third base oil.
• the present invention is directed to a base oil blend, wherein the diester component has a Noack Volatility between about 6 and 10 wt%, a CCS Viscosity at -30°C between about 700 and 2000 cP, a pour point less than about -10°C, a cloud point less than about -10°C, a kinematic viscosity at 100°C between about 2.5 to 6.5 centistokes, and a VI greater than about 110 and a BN Oxidator greater than about 20 hours.
• the diester component has a Noack Volatility between about 6 and 10 wt%, a CCS Viscosity at -30°C between about 700 and 2000 cP, a pour point less than about -10°C, a cloud point less than about -10°C, a kinematic viscosity at 100°C between about 2.5 to 6.5 centistokes, and a VI greater than about 110 and a BN Oxidator greater than about 20 hours.
• the present invention is directed to a base oil blend, wherein the diester component has a Noack Volatility between about 6 and 9 wt%, and a CCS Viscosity at -30°C between about 800 and 1900 cP.
• the present invention is directed to a base oil blend, wherein the diester component has a Noack Volatility between about 6 and 9 wt%, and a CCS Viscosity at -25°C between about 400 and 1250 cP.
• the present invention is directed to a base oil blend, wherein the second base oil is light neutral base oil, medium neutral base oil, Yubase 4, Yubase 6, 150R, 600R, 110RLV, 220R or 100R.
• the present invention is directed to a base oil blend, wherein the third base oil is light neutral base oil, medium neutral base oil, Yubase 4, Yubase 6, 150R, 600R, 1 lORLV, 220R or 100R.
• the present invention is directed to a base oil blend, having: a) a viscosity index between about 110 to 140; b) a Noack volatility of less than about 16 wt %; c) a Pour Point less than about -12° C; and d) a Cloud Point less than about -12° C.
• the present invention is directed to a base oil blend, wherein the kinematic viscosity at a temperature of 100°C is between about 3 to 5.5 centistokes. In some embodiments, the present invention is directed to a base oil blend, wherein the Pour Point and Cloud Point are independently about -20°C or lower.
• the present invention is directed to a base oil blend, wherein the CCS Viscosity at -30°C less than about 4,200 cP.
• the present invention is directed to a base oil blend, wherein the CCS Viscosity at -35°C less than about 3,400 cP.
• the present invention is directed to a base oil blend, wherein the CCS Viscosity at -25°C less than about 2,400 cP.
• the present invention is directed to a base oil blend, wherein the Noack Volatility less than about 15 wt%.
• the present invention is directed to a base oil blend, wherein Ri and R2 of Formula I are selected to have a combined carbon number of from 6 to 16 and R3 and R4 are selected to have a combined carbon number of from 10 to 34.
• the present invention is directed to a base oil blend, wherein Ri and R2 of Formula I are selected to have a combined carbon number of Ci 6 , C14 or C12 and R 3 and R4 are independently selected from the group consisting of C12 and a mixture of C6-C1 0 .
• the present invention is directed to a base oil blend, wherein the diester component is derived from a Cs to Cis olefin and a Ce to C14 carboxylic acid.
• the present invention is directed to a base oil blend, wherein the diester component comprises quantities of at least two different diester isomers.
• the present invention is directed to a base oil blend, wherein the diester component has a molecular mass that is from at least about 340 a.m.u. to at most about 780 a.m.u.
• the present invention is directed to a base oil blend, wherein the diester component is selected from the group consisting of decanoic acid 2-decanoyloxy- 1-hexyl-octyl ester and its isomers, tetradecanoic acid- l -hexyl-2-tetradecanoyloxy-octyl esters and its isomers, dodecanoic acid 2-dodecanoyloxy- l-hexyl-octyl ester and its isomers, hexanoic acid 2-hexanoyloxy- l-hexy-octyl ester and its isomers, octanoic acid 2- octanoyloxy- 1 -hexyl-octyl ester and its isomers, hexanoic acid 2-hexanoyloxy- l-pentyl- heptyl ester and isomers, o
• the present invention is directed to a process for improving cold flow properties and lowering Noack in a starting base oil or starting base oil blend, comprising: replacing between about 5 to 60 wt % of a starting base oil or starting base oil blend with an equal quantity of a base oil comprising: a) a diester component, comprising a quantity of at least one diester species of Formula I:
• Ri, R 2 , R3 and R4 are the same or independently selected from C2 to C17 hydrocarbon groups, and wherein the process affords an upgraded base oil blend.
• the present invention is directed to a process for improving cold flow properties and lowering Noack in a starting base oil or starting base oil blend, wherein improving cold flow properties, further comprises lowering CCS VIS (cold-cranking simulator apparent viscosity) at -25° C, -30°C or -35° C, lowering pour point and lowering Noack.
• improving cold flow properties further comprises lowering CCS VIS (cold-cranking simulator apparent viscosity) at -25° C, -30°C or -35° C, lowering pour point and lowering Noack.
• CCS VIS cold-cranking simulator apparent viscosity
• the present invention is directed to a process for improving cold flow properties and lowering Noack in a starting base oil or starting base oil blend, further comprising a process for lowering CCS Viscosity and lowering Noack in a starting base oil or starting base oil blend, comprising: replacing between about 5 to 60 wt % of a starting base oil or starting base oil blend with an equal quantity of a base oil comprising: a) a diester component, comprising a quantity of at least one diester species of Formula I:
• Ri, R 2 , R3 and R4 are the same or independently selected from C2 to C17 hydrocarbon groups, and wherein the process affords an upgraded base oil blend.
• the present invention is directed to a process for lowering CCS Viscosity and lowering Noack in a starting base oil or starting base oil blend, further comprising a diester component that comprises a mixture of isomers where Ri and R2 are independently different for each isomer.
• the present invention is directed to a process for lowering CCS
• the base oil or base oil blend comprises a Group I base oil, Group II base oil or Group III base oil.
• the present invention is directed to a process for lowering CCS Viscosity and lowering Noack in a starting base oil or starting base oil blend, wherein the upgraded base oil blend comprises at least one of light neutral base oil, medium neutral base oil, Yubase 4, Yubase 6, 150R, 600R, 1 lORLV, 100R and 220R.
• the present invention is directed to a process for lowering CCS Viscosity and lowering Noack in a starting base oil or starting base oil blend, wherein the diester component has a Noack Volatility between 6 and 10 wt%, a pour point less than - 10°C, a cloud point less than -10°C, a kinematic viscosity at 100°C between 2.5 to 6.5 centistokes, a VI greater than 1 10 and a BN Oxidator greater than 20 hours.
• the present invention is directed to a process for lowering CCS Viscosity and lowering Noack in a starting base oil or starting base oil blend, wherein the kinematic viscosity of the upgraded base oil blend at a temperature of 100°C is between 3 to 5.5 centistokes. In some embodiments, the present invention is directed to a process for lowering CCS Viscosity and lowering Noack in a starting base oil or starting base oil blend, wherein the upgraded base oil blend has a Pour Point and Cloud Point are independently -12°C or lower.
• the present invention is directed to a process for lowering CCS Viscosity and lowering Noack in a starting base oil or starting base oil blend, wherein the upgraded base oil blend has a CCS Viscosity at -30°C less than 4,200 cP.
• the present invention is directed to a process for lowering CCS Viscosity and lowering Noack in a starting base oil or starting base oil blend, wherein the upgraded base oil blend has a CCS Viscosity at -35°C less than 3,400 cP.
• the present invention is directed to a process for lowering CCS
• the present invention is directed to a process for lowering CCS Viscosity and lowering Noack in a starting base oil or starting base oil blend, wherein the upgraded base oil blend has a Noack Volatility less than 15 wt%.
• the present invention is directed to a process for lowering CCS Viscosity and lowering Noack in a starting base oil or starting base oil blend, wherein Ri and R2 of Formula I are selected to have a combined carbon number of from 6 to 16 and R 3 and R4 are selected to have a combined carbon number of from 10 to 34.
• the present invention is directed to a process for lowering CCS
• Viscosity and lowering Noack in a starting base oil or starting base oil blend wherein Ri and R2 of Formula I are selected to have a combined carbon number of Ci 6 , C14 or C12 and R 3 and R t are independently selected from the group consisting of C12 and a mixture of C6-C1 0 .
• the present invention is directed to a process for lowering CCS Viscosity and lowering Noack in a starting base oil or starting base oil blend, wherein the diester component is derived from a Cs to Cis olefin and a Ce to C14 carboxylic acid.
• the present invention is directed to a process for lowering CCS Viscosity and lowering Noack in a starting base oil or starting base oil blend, wherein the upgraded base oil blend comprises quantities of at least two different diester isomers.
• the present invention is directed to a process for lowering CCS
• Viscosity and lowering Noack in a starting base oil or starting base oil blend further comprising an upgraded base oil blend with about a 2 to 35% lower Noack Volatility as compared to the starting base oil or starting base oil blend.
• the present invention is directed to a process for lowering CCS Viscosity and lowering Noack in a starting base oil or starting base oil blend, further comprising an upgraded base oil blend with about a 2 to 35% lower CCS Viscosity at -35° or CCS Viscosity at -30° as compared to the starting base oil or starting base oil blend.
• the present invention is directed to a process for lowering CCS Viscosity and lowering Noack in a starting base oil or starting base oil blend, wherein the diester component has a molecular mass that is from at least about 340 a.m.u. to at most about 780 a.m.u.
• the present invention is directed to a process for lowering CCS Viscosity and lowering Noack in a starting base oil or starting base oil blend, wherein the diester component is selected from the group consisting of decanoic acid 2-decanoyloxy-l- hexyl-octyl ester and its isomers, tetradecanoic acid-l-hexyl-2-tetradecanoyloxy-octyl esters and its isomers, dodecanoic acid 2-dodecanoyloxy-l-hexyl-octyl ester and its isomers, hexanoic acid 2-hexanoyloxy-l-hexy-octyl ester and its isomers, octanoic acid 2- octanoyloxy- 1 -hexyl-octyl ester and its isomers, hexanoic acid 2-hexanoyloxy-l
• Group I Base Oil contain less than 90 percent saturates and/or greater than 0.03 percent sulfur and have a viscosity index greater than or equal to 80 and less than 120 using the ASTM methods specified in Table E-l of American Petroleum Institute Publication 1509.
• Group II Base Oil refers to a base oil which contains greater than or equal to 90% saturates and less than or equal to 0.03% sulfur and has a viscosity index greater than or equal to 80 and less than 120 using the ASTM methods specified in Table E-l of American Petroleum Institute Publication 1509.
• Group 11+ Base Oil refers to a Group II base oil having a viscosity index greater than or equal to 1 10 and less than 120.
• Group III Base Oil refers to a base oil which contains greater than or equal to 90% saturates and less than or equal to 0.03% sulfur and has a viscosity index greater than or equal to 120 using the ASTM methods specified in Table E-l of American Petroleum Institute Publication 1509.
• Fischer-Tropsch derived means that the product, fraction, or feed originates from or is produced at some stage by a Fischer-Tropsch process.
• petroleum derived means that the product, fraction, or feed originates from the vapor overhead streams from distilling petroleum crude and the residual fuels that are the non-vaporizable remaining portion.
• a source of the petroleum derived product, fraction, or feed can be from a gas field condensate.
• multi-grade engine oil refers to an engine oil that has viscosity/temperature characteristics which fall within the limits of two different SAE numbers in SAE J300.
• the present invention is directed to the discovery that multi-grade engine oils meeting the specifications under SAE J300 as revised 2009, including the MRV viscosity specifications, may be prepared from Fischer-Tropsch base oils having a defined cycloparaffin functionality when they are blended with a pour point depressing base oil blending component and an additive package.
• light neutral base oil refers to a base oil with a boiling range from about 700°F to about 800°F, a kinematic viscosity at 100°C from 4 cSt to about 5 cSt.
• intermediate neutral base oil refers to a base oil with a boiling range from about 800°F to about 900°F, a kinematic viscosity at 100°C from 5 cSt to about 8 cSt.
• Highly paraffinic wax means a wax having a high content of n-paraffins, generally greater than 40 wt %, but can be greater than 50 wt %, or even greater than 75 wt %, and less than 100 wt % or 99 wt %.
• highly paraffinic waxes include slack waxes, deoiled slack waxes, refined foots oils, waxy lubricant raffinates, n-paraffin waxes, NAO waxes, waxes produced in chemical plant processes, deoiled petroleum derived waxes, microcrystalline waxes, Fischer-Tropsch waxes, and mixtures thereof.
• derived from highly paraffinic wax means that the product, fraction, or feed originates from or is produced at some stage by from a highly paraffinic wax.
• Representative examples include, but are not limited to, benzene, biphenyl, naphthalene, and the like.
• Molecules with cycloparaffinic functionality mean any molecule that is, or contains as one or more substituents, a monocyclic or a fused multicyclic saturated hydrocarbon group.
• the cycloparaffinic group can be optionally substituted with one or more, such as one to three, substituents.
• Representative examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclohexyl, cyclopentyl, cycloheptyl, decahydronaphthalene, octahydropentalene, (pentadecan-6-yl)cyclohexane, 3,7, 10-tricyclohexylpentadecane, decahydro-l-(pentadecan-6- yl)naphthalene, and the like.
• Molecules with monocycloparaffinic functionality mean any molecule that is a monocyclic saturated hydrocarbon group of three to seven ring carbons or any molecule that is substituted with a single monocyclic saturated hydrocarbon group of three to seven ring carbons.
• the cycloparaffinic group can be optionally substituted with one or more, such as one to three, substituents. Representative examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclohexyl, cyclopentyl, cycloheptyl, (pentadecan-6-yl)cyclohexane, and the like.
• Molecules with multicycloparaffinic functionality mean any molecule that is a fused multicyclic saturated hydrocarbon ring group of two or more fused rings, any molecule that is substituted with one or more fused multicyclic saturated hydrocarbon ring groups of two or more fused rings, or any molecule that is substituted with more than one monocyclic saturated hydrocarbon group of three to seven ring carbons.
• the fused multicyclic saturated hydrocarbon ring group often is of two fused rings.
• the cycloparaffinic group can be optionally substituted with one or more, such as one to three, substituents.
• Representative examples include, but are not limited to, decahydronaphthalene, octahydropentalene, 3,7, 10- tricyclohexylpentadecane, decahydro-l-(pentadecan-6-yl)naphthalene, and the like.
• Brookfield Viscosity ASTM D2983-04a is used to determine the low-shear-rate viscosity of automotive fluid lubricants at low temperatures.
• the low-temperature, low-shear- rate viscosity of automatic transmission fluids, gear oils, torque and tractor fluids, and industrial and automotive hydraulic oils are frequently specified by Brookfield viscosities.
• Kinematic viscosity is a measurement of the resistance to flow of a fluid under gravity. Many base oils, lubricant compositions made from them, and the correct operation of equipment depends upon the appropriate viscosity of the fluid being used. Kinematic viscosity is determined by ASTM D445-06. The results are reported in mm 2 /s.
• Viscosity index (VI) is an empirical, unitless number indicating the effect of temperature change on the kinematic viscosity of the oil. Viscosity index is determined by ASTM D2270-04.
• Pour point is a measurement of the temperature at which a sample of base oil will begin to flow under carefully controlled conditions. Pour point can be determined as described in ASTM D5950-02. The results are reported in degrees Celsius. Many commercial base oils have specifications for pour point. When base oils have low pour points, the base oils are also likely to have other good low temperature properties, such as low cloud point, low cold filter plugging point, and low temperature cranking viscosity.
• Noack volatility is usually tested according to ASTM D5800-05 Procedure B.
• a more convenient method for calculating Noack volatility and one which correlates well with ASTM D5800-05 is by using a thermogravimetric analyzer (TGA) test by ASTM D6375-05.
• TGA Noack volatility is used throughout the present disclosure unless otherwise stated.
• the base oils of the lubricant composition as disclosed herein also have excellent viscometric properties under low temperature and high shear, making them very useful in multi-grade engine oils.
• the cold-cranking simulator apparent viscosity (CCS VIS) is a test used to measure the viscometric properties of base oils under low temperature and high shear.
• the test method to determine CCS VIS is ASTM D5293-02. Results are reported in mPa-s.
• CCS VIS has been found to correlate with low temperature engine cranking. Specifications for maximum CCS VIS are defined for automotive engine oils by SAE J300, revised in 2009. The maximum CCS VIS for a 0W SAE Viscosity Grade engine oil is 6200 mPa-s at -35°C.
• the phrase "improving cold flow properties” refers to one or more of lowering CCS VIS (cold-cranking simulator apparent viscosity) at -25° C, -30°C or -35° C, lowering pour point and lowering Noack.
• the Mini-Rotary Viscometer (MRV) test ASTM D4684-07, which is related to the mechanism of pumpability, is a low shear rate measurement.
• Slow sample cooling rate is the method's key feature.
• a sample is pretreated to have a specified thermal history which includes warming, slow cooling, and soaking cycles.
• the MRV measures an apparent yield stress, which, if greater than a threshold value, indicates a potential air-binding pumping failure problem. Above a certain viscosity (currently defined as 60,000 mPa-s by SAE J300 2009), the oil may be subject to pumpability failure by a mechanism called "flow limited" behavior.
• An SAE 0W oil for example, is required to have a maximum viscosity of 60,000 mPa-s at -40°C with no yield stress. This method also measures an apparent viscosity under shear rates of 1 to 50 s "1 .
• High temperature high shear rate viscosity is a measure of a fluid's resistance to flow under conditions resembling highly-loaded journal bearings in fired internal combustion engines, typically 1 million s "1 at 150°C.
• HTHS is a better indication of how an engine operates at high temperature with a given lubricant than the kinematic low shear rate viscosities at 100°C.
• the HTHS value directly correlates to the oil film thickness in a bearing.
• SAE J300 2009 contains the current specifications for HTHS measured by ASTM D4683, ASTM D4741, or ASTM D5481.
• An SAE 20 viscosity grade engine oil for example, is required to have a minimum HTHS of 2.6 mPa-s.
• ASTM D5133-05 is used to measure the low temperature, low shear rate, viscosity/temperature dependence of engine oils.
• the low temperature, low shear viscometric behavior of an engine oil determines whether the oil will flow to the sump inlet screen, then to the oil pump, then to the sites in the engine requiring lubrication in sufficient quantity to prevent engine damage immediately or ultimately after cold temperature starting.
• ASTM D5133-05 the Scanning Brookfield Viscosity technique, measures the Brookfield viscosity of a sample as it is cooled at a constant rate of l°C/hour.
• ASTM D5133-05 is intended to relate to the pumpability of an oil at low temperatures.
• the test reports the gelation point, defined as the temperature at which the sample reaches 30,000 mPa-s.
• the gelation index is also reported, and is defined as the largest rate of change of viscosity increase from -5°C to the lowest test temperature.
• the latest API SM/ILSAC GF-4 specifications for passenger car engine oils require a maximum gelation index of 12.
• “Lubricants,” as defined herein, are substances (usually a fluid under operating conditions) introduced between two moving surfaces so to reduce the friction and wear between them.
• Base oils used as motor oils are generally classified by the American Petroleum Institute as being mineral oils (Group I, II, and III) or synthetic oils (Group IV and V). See American Petroleum Institute (API) Publication Number 1509.
• “Pour point,” as defined herein, represents the lowest temperature at which a fluid will pour or flow. See, e.g., ASTM International Standard Test Methods D 5950-96, D 6892- 03, and D 97.
• Cloud point represents the temperature at which a fluid begins to phase separate due to crystal formation. See, e.g., ASTM Standard Test Methods D 5773-95, D 2500, D 5551, and D 5771.
• R n refers to a hydrocarbon group, wherein the molecules and/or molecular fragments can be linear and/or branched.
• C n As defined herein, "C n ,” where “n” is an integer, describes a hydrocarbon molecule or fragment (e.g., an alkyl group) wherein “n” denotes the number of carbon atoms in the fragment or molecule.
• bio refers to an association with a renewable resource of biological origin, such as resource generally being exclusive of fossil fuels.
• an "upgraded base oil blend” refers to a base oil or base oil blend that has had a portion replaced with a diester herein to afford the upgraded base oil blend having improved cold flow properties and lower Noack compared to the starting base oil or base oil blend.
• Yubase 4 and Yubase 6 are base oils defined as presented in Table 1 shown below.
• This example serves to illustrate the base oil blends with and without the diesters of the present invention with the analytics presented in Table 3 below.
• the diester- free base oil blend was prepared by mixing 82.67 wt% Yubase 4 and 17.33 wt% Yubase 6.
• the base oil component with diester was prepared by mixing 69.7 wt% Yubase 4, 13.8 wt% Yubase 6, and 16.5 wt% diester of Formula I wherein Ri and R2 are combined to have a carbon number of C12 and R3 and R4 are both C12. Both samples were submitted for standard base oil testing, including API gravity, viscosity at 40°C and 100°C, Viscosity Index, pour point, cloud point, Noack volatility, cold cranking viscosity, and Bromine number.
• This example serves to illustrate the base oil blends with the diesters of the present invention, a single comparative without diester and a second comparative with a commercially available ester (i.e., Esterex A51) with the analytics presented in Table 4 below.
• Diester A is a diester of Formula I, wherein Ri and R2 are combined to have a carbon number of C12 and R 3 and R4 are both C12.
• Diester B2 is a diester of Formula I, wherein Ri and R2 are combined to have a carbon number of C 12 and R3 and R4 are both independently C6-C1 0 .
• the examples in Table 3 were prepared in a similar manner as those of Example 1 herein.
• This example serves to illustrate the diesters prepared and their respective properties as presented in Table 5.
• This example serves to illustrate the Noack and CCS Viscosity of the diesters of the present invention as compared to the current commercial esters and other Group II and III bases oils as presented in Table 6 and Figure 1.

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