US20170240832A1 - Engine oils from renewable isoparaffins - Google Patents

Engine oils from renewable isoparaffins Download PDF

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US20170240832A1
US20170240832A1 US15/518,878 US201515518878A US2017240832A1 US 20170240832 A1 US20170240832 A1 US 20170240832A1 US 201515518878 A US201515518878 A US 201515518878A US 2017240832 A1 US2017240832 A1 US 2017240832A1
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engine oil
oil
astm
biobased
base oil
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Hyeok Hahn
Jeffrey Brown
Paula VETTEL
Jason Wells
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Novvi LLC
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Novvi LLC
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    • 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
    • C10M105/02—Well-defined hydrocarbons
    • C10M105/04—Well-defined hydrocarbons aliphatic
    • 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
    • C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • C10M101/02—Petroleum fractions
    • 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
    • C10M105/02—Well-defined hydrocarbons
    • 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
    • C10M109/00—Lubricating compositions characterised by the base-material being a compound of unknown or incompletely defined constitution
    • C10M109/02—Reaction products
    • 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
    • C10M2203/003—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms 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
    • C10N2020/04—Molecular weight; Molecular weight distribution
    • 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
    • C10N2020/081—Biodegradable compounds
    • 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
    • C10N2030/06—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
    • C10N2030/10—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
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • 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
    • C10N2220/021—
    • C10N2230/04—
    • C10N2230/06—
    • C10N2230/10—
    • C10N2230/12—
    • C10N2230/64—
    • C10N2230/74—
    • C10N2240/10—

Definitions

  • the present disclosure generally relates to engine oils.
  • the disclosure relates to biobased engine oils comprising a biobased hydrocarbon such as isoparaffinic hydrocarbon derived from hydrocarbon terpenes such as myrcene, ocimene and farnesene.
  • Crankcase oils commonly referred as an engine oil, constitutes about 40 ⁇ 50% of global lubricant market and is often considered as a focal point for research, development, and marketing effort of lubricant industry.
  • Biobased engine oils while limited in market, have traditionally been based on natural or synthetic ester products (e.g., vegetable oils).
  • Vegetable oils for example, are renewable and biodegradable, but they breakdown and oxidize at high temperatures and are not hydrolytically stable.
  • vegetable oils when incorporated into a passenger car engine oil, vegetable oils are typically blended with synthetic oils at a proportion of about 5-30%.
  • Automotive OEMs national trade associations (such as API and ACEA), and international standardization committee (such as ILSAC) have been playing major role in overseeing the development and implementation of standard engine oil related test methods. They also provide official classifications and labeling program for engine oils (such as ILSAC GF-5, API-SN, ACEA A3/B4, and dexos) in order to provide consumers a guidance for choosing the correct engine oils for their vehicles. These classifications require a series of engine tests and bench top performance tests which are designed to evaluate engine oil's performance in providing desired protection including longevity, corrosion and wear protection, resistance to the formation of sludge and deposits, ability to retain its viscosity in right range, etc.
  • ILSAC international standardization committee
  • ILSAC GF-5 which was approved in January 2010 and became sole basis for issuance of a license to use the API certification mark, requires 5 engine tests (i.e. sequence III, IV, V, VI, and VIII) and series bench tests (i.e. catalyst compatibility, phosphorus content, Noack volatility, high temperature deposit tests, filterability, foaming characteristic, aged oil low temperature viscosity, shear stability, homogeneity, miscibility, ball rust test, emulsion retention, and elastomer compatibility test).
  • engine tests i.e. sequence III, IV, V, VI, and VIII
  • series bench tests i.e. catalyst compatibility, phosphorus content, Noack volatility, high temperature deposit tests, filterability, foaming characteristic, aged oil low temperature viscosity, shear stability, homogeneity, miscibility, ball rust test, emulsion retention, and elastomer compatibility test.
  • Biobased base oil penetration on the engine oil market is currently relatively low, due at least in part to the inherent performance disadvantages of the ester materials that have been used as well as the rules and regulations in the segment.
  • Biobased engine oils have traditionally been based on natural or synthetic ester products. This has allowed the products to be strong in the areas of renewability and biodegradability but weak in some of the classical performance areas of an engine oil as provided by the more typical hydrocarbon base oils. These main limitations are around hydrolytic stability, seal and material compatibility, oxidation stability, cold weather performance, and compatibility with existing non-biobased engine oils.
  • an engine oil offering certain environmental performance characteristics
  • the provision of an engine oil formulated with vegetable oil based base oil the provision of an engine oil comprising a biobased hydrocarbon
  • the provision of clean biodegradable alternative hydrocarbon products which have improved environmental performance and/or physical properties such as better oxidative stability, better cold flow, low volatility, improved separation of oil from water (and air), and improved anti-wear properties.
  • one aspect of the present disclosure is an engine oil comprising a biobased hydrocarbon base oil that meets the requirements of Engine Oil Viscosity Classification (J300 2009-01) set by SAE and has a volatile loss of less than 13% when measured by ASTM D5800-10.
  • an engine oil comprising a biobased base oil, wherein the biobased base oil has greater than 90% saturates as measured by ASTM-D2007-11, less than 0.03% sulfur as measured by ASTM-D1552-08(2014)e1, ASTM D2622-10, ASTM D3120-08, ASTM D4294-10, ASTM D4927-10 or equivalent method, a viscosity index as measured by ASTM D2270-10e1 greater than 120, a renewable carbon content greater than 25% as measured by ASTM-D6866-12, contains a dispersant, a detergent, a corrosion inhibitor, an antioxidant, an antifoaming agent, an antiwear agent, and a friction modifier, and wherein the engine oil has, when determined by ASTM-D7320-13, (a) a kinematic viscosity increase, at 40° C., of no more than 150%, (b) an average weighted piston deposit rating greater than 4.0, and (c) an average cam plus lifter wear of less than 60
  • an engine oil comprising a biobased Group III base oil, wherein the biobased Group III base oil has a renewable carbon content greater than 25% as measured by ASTM-D6866-12, contains a dispersant, a detergent, a corrosion inhibitor, antioxidant, an antifoaming agent, an antiwear agent, and a friction modifier, and wherein the engine oil has, when determined by ASTM-D7320-13, (a) a kinematic viscosity increase, at 40° C., of no more than 150%, (b) an average weighted piston deposit rating greater than 4.0, and (c) an average cam plus lifter wear of less than 60 ⁇ m.
  • Another aspect of the present disclosure is an engine oil comprising a dispersant, a detergent, a corrosion inhibitor, antioxidant, an antifoaming agent, an antiwear agent, a friction modifier, and a biobased base oil, wherein the biobased base oil having the molecular structure:
  • an engine oil comprising a group III base oil, wherein the engine oil does not contain pour point depressant but contains a dispersant, a detergent, a corrosion inhibitor, an antioxidant, an antifoaming agent, an anti-wear agent, and a friction modifier, and wherein the engine oil has, when determined by ASTM-D7320-13, (a) a kinematic viscosity increase, at 40° C., of no more than 150%, (b) an average weighted piston deposit rating greater than 4.0, and (c) an average cam plus lifter wear of less than 60 ⁇ m.
  • an engine oil comprising: (a) at least 50 wt % of a biobased base oil having a weight average molecular weight in the range of 300 to 1500 g/mol and a viscosity index greater than 120; and (b) wherein the engine oil has (i) a cold cranking viscosity less than 6200 cP at ⁇ 35° C. by ASTM D 5293-14, (ii) a low temperature pumping viscosity less than 60000 at ⁇ 40° C. by ASTM D4684-14, and (iii) a kinematic viscosity greater than 3.8cSt at 100° C. by ASTM D445-14E2.
  • an engine oil comprising a biobased base oil, wherein the biobased base oil has greater than 50% of biodegradation in 28 days according to OECD 301B test method, the biobased base oil constitutes at least 50 wt % of the engine oil, and wherein the engine oil has, when determined by ASTM-D7320-13, (a) a kinematic viscosity increase, at 40° C., of no more than 150%, (b) an average weighted piston deposit rating greater than 4.0, and (c) an average cam plus lifter wear of less than 60 ⁇ m.
  • Another aspect of the present disclosure is an engine oil comprising a biobased base oil and an additive package wherein (i) the engine oil and an otherwise identical engine oil comprising the additive package and a Group I, Group II or Group III base oil but no biobased base oil each satisfy the requirements of Engine Oil Viscosity Classification (J300) set by SAE and has a volatile loss of less than 13% when measured by ASTM D5800-10 and (ii) the engine oil even in the absence of additional solubilizer, co-base oil or co-solvent outperforms the otherwise identical engine oil in the Engine Oil Viscosity Classification (J300) and ASTM D5800-10 tests.
  • J300 Engine Oil Viscosity Classification
  • Another aspect of the present disclosure is an engine oil comprising a biobased base oil and at least 0.1 wt % of a dispersant inhibitor, wherein the engine oil is compatible with engine oils formulated using Group I, Group II, or Group III base oil, meets requirements of Engine Oil Viscosity Classification (J300) set by SAE and has a volatile loss of less than 13% when measured by ASTM D5800-10.
  • J300 Engine Oil Viscosity Classification
  • Another aspect of the present disclosure is an engine oil satisfying the performance requirements of Engine Oil Viscosity Classification (J300), wherein the engine oil comprises: (a) 1 to 95 wt % of a biobased hydrocarbon base oil; (b) up to 80 wt % of one or more co-base oils, wherein the co-base oil(s) are selected from Group I, Group II, Group III, Group IV, and Group V base oils and combinations thereof, and (c) up to 30 wt % of one or more additives selected from the group consisting of anti-foaming agents, anti-wear agents, anti-oxidants, demulsifiers, detergents, dispersants, extreme pressure agents, friction modifiers, metal deactivators, pour point depressants, rust and corrosion inhibitors, viscosity modifiers, and combinations thereof.
  • the engine oil comprises: (a) 1 to 95 wt % of a biobased hydrocarbon base oil; (b) up to 80 wt % of one or more co-base oils, wherein the co
  • Another aspect of the present disclosure is an internal combustion engine lubricated by an engine oil, the improvement comprising an engine oil according to any of the preceding paragraphs.
  • Another aspect of the present disclosure is a process for formulating an engine oil, the process comprising combining a biobased base oil with an additive mixture and a viscosity modifier to form a first combination that meets or exceeds the performance requirements of one or more of the following engine oil certification programs: ILSAC GF-5, ILSAC GF-6, API SN, dexos, CJ-4, ACEA-A1, ACEA-A2, ACEA-A3, ACEA-B1, ACEA-B2, ACEA-B3, ACEA-B4, ACEA-E1, ACEA-E2, ACEA-E3, ACEA-E4, and PC-11, wherein
  • the additive mixture comprises two or more additives selected from the group consisting of anti-foaming agents, anti-wear agents, anti-oxidants, demulsifiers, detergents, dispersants, extreme pressure agents, friction modifiers, metal deactivators, pour point depressants, rust and corrosion inhibitors, viscosity modifiers, and combinations thereof, and
  • the additive mixture without variation of the combination of additives or the relative proportions thereof within the additive mixture may alternatively be combined with a non-biobased Group I, a Group II, a Group III or a Group IV base oil, or a combination thereof, and a viscosity modifier to form a second combination that meets or exceeds the performance requirements of one or more of the following engine oil certification programs: ILSAC GF-5, ILSAC GF-6, API SN, dexos, CJ-4, ACEA-A1, ACEA-A2, ACEA-A3, ACEA-B1, ACEA-B2, ACEA-B3, ACEA-B4, ACEA-E1, ACEA-E2, ACEA-E3, ACEA-E4, and PC-11.
  • Another aspect of the present disclosure is an engine oil wherein at least about 25% of the carbon atoms in the biobased base oil originate from renewable carbon sources and the engine oil has a pour point of less than ⁇ 40° C. in the absence of a pour point depressant additive.
  • Another aspect of the present disclosure is an engine oil comprising a biobased hydrocarbon base oil, wherein the amount of biobased base oil in the engine oil is greater than 50% and the biobased base oil has a biodegradable rate in excess of 60% according to by OECD 301B.
  • Another aspect of the present disclosure is an engine oil formulation comprising at least one engine oil additive and a biobased base oil having the molecular structure:
  • Another aspect of the present disclosure is an engine oil that can be mixed with a Group I, a Group II, a Group III or a Group IV base oil, or a combination thereof and used for engine oil top-off and/or during engine oil change where previous engine oil is formulated with a Group I, a Group II, a Group III or a Group IV base oil, or a combination thereof.
  • Another aspect of the present disclosure is an internal combustion engine lubricated by an engine oil as described in any of the preceding paragraphs.
  • Another aspect of the present disclosure is a biobased engine oil that can meet the industry specifications of API SN, ILSAC GF-5 when a biobased base oil is combined with an off-the-shelf additive package and viscosity modifier.
  • FIG. 1 is a plot comparing high temperature high shear viscosity at 150° C. as a function of kinematic viscosity at 100° C. of commercially available, non biobased base oils compared to those of biobased hydrocarbon base oils.
  • FIG. 2 is a plot showing high temperature high shear viscosity at 150° C. as a function of kinematic viscosity at 100° C. of commercially available, non biobased base oils blended with viscosity modifier (VM) commonly used for engine oil formulations compared to those of biobased hydrocarbon base oils with same VM.
  • VM viscosity modifier
  • FIG. 3 is a plot comparing cranking viscosity, at ⁇ 35° C. measured by ASTM-D5293-14, of base oils and their blends as a function of volatile loss measured by ASTM-D5800-10.
  • FIG. 4 is a plot comparing cranking viscosity, at ⁇ 35° C. measured by ASTM-D5293-14, of base oils and their blends as a function of kinematic viscosity at 100° C. measured by ASTM-D445-14E2.
  • FIG. 5 is a plot comparing oxidative stability of engine oils formulated using same additives and different base oils.
  • FIG. 6 is a plot comparing oxidative stability of 0W-20 engine oil formulated using biobased hydrocarbon base oil to commercially available 0W-20 engine oils and 5W-20 engine oil.
  • FIG. 7 is a plot comparing biodegradation curves obtained from biobased base oil, group III base oil, and group IV base oil, with similar kinematic viscosity, using OECD 301B method.
  • “Compatible” or “compatibility” as used herein in connection with engine oil lubricants can be defined as the mixing of different fluids will not result in a loss of solubility and/or the responsiveness of the additive ingredients used in either of the two formulations. The mixing of the two formulations does not diminish effectiveness of the additives to perform as intended. Thus, for example, two engine oil lubricants are compatible when, if mixed in any proportion, the mixture will meet or exceed the performance characteristics possessed by at least one of the two formulations immediately prior to the mixing.
  • biobased base oil is understood to mean any biologically derived oil to be used as a base oil in a engine oil.
  • oils may be made, for non-limiting example, from biological organisms designed to manufacture specific oils, as discussed in PCT Patent Application No. PCT/US2012/024926, published as WO 2012/141784, cited above, but do not include petroleum distilled or processed oils such as for non-limiting example mineral oils.
  • a suitable method to assess materials derived from renewable resources is through ASTM D6866-12, “Standard Test Methods for Determining the Biobased Content of Solid, Liquid, and Gaseous Samples Using Radiocarbon Analysis.” Counts from 14 C in a sample can be compared directly or through secondary standards to SRM 4990C.
  • a measurement of 0% 14 C relative to the appropriate standard indicates carbon originating entirely from fossils (e.g., petroleum based).
  • a measurement of 100% 14 C indicates carbon originating entirely from modern sources. See, e.g., WO 2012/141784, incorporated herein by reference.
  • Base oils and more particularly isoparaffins, derived from biobased hydrocarbon terpenes such as myrcene, ocimene and farnesene, have been described in PCT Patent Application No. PCT/US2012/024926, entitled “Base Oils and Methods for Making the Same,” filed, Feb. 13, 2012 and published as WO 2012/141784 on Oct. 18, 2012, by Nicholas Ohler, et al., and assigned to Amyris, Inc. in Emeryville, Calif.
  • terpenes are capable of being derived from isopentyl pyrophosphate or dimethylallyl pyrophosphate and the term “terpene” encompasses hemiterpenes, monoterpenes, sesquiterpenes, diterpenees, sesterterpenes, triterpenes, tetraterpenes and polyterpenes.
  • a hydrocarbon terpene contains only hydrogen and carbon atoms and no heteroatoms such as oxygen, and in some embodiments has the general formula (C 5 H 8 ) n , where n is 1 or greater.
  • conjugated terpene or “conjugated hydrocarbon terpene” refers to a terpene comprising at least one conjugated diene moiety.
  • the conjugated diene moiety of a conjugated terpene may have any stereochemistry (e.g., cis or trans) and may be part of a longer conjugated segment of a terpene, e.g., the conjugated diene moiety may be part of a conjugated triene moiety.
  • Hydrocarbon terpenes also encompass monoterpenoids, sesquiterpenoids, diterpenoids, triterpenoids, tetraterpenoids, and polyterpenoids that exhibit the same carbon skeleton as the corresponding terpene but have either a lesser or greater number of hydrogen atoms than the corresponding terpene, e.g., terpenoids having 2 fewer, 4 fewer, or 6 fewer hydrogen atoms than the corresponding terpene, or terpenoids having 2-additional 4-additional, or 6-additional hydrogen atoms than the corresponding terpene.
  • conjugated hydrocarbon terpenes include isoprene, myrcene, ⁇ -ocimene, ⁇ -ocimene, ⁇ -farnesene, ⁇ -farnesene, ⁇ -springene, geranylfarnesene, neophytadiene, cis-phyta-1,3-diene, trans-phyta-1,3-diene, isodehydrosqualene, isosqualane precursor I, and isosqualane precursor II.
  • the terms terpene and isoprenoids may be used interchangeably and are a large and varied class of organic molecules that can be produced by a wide variety of plants and some insects.
  • terpenes or isoprenoid compounds can also be made from organic compounds such as sugars by microorganisms, including bioengineered microorganisms, such as yeast. Because terpenes or isoprenoid compounds can be obtained from various renewable sources, they are useful monomers for making eco-friendly and renewable base oils.
  • the conjugated hydrocarbon terpenes are derived from microorganisms using a renewable carbon source, such as a sugar.
  • C15 hydrocarbons containing four double bonds such as BiofeneTM ⁇ -farnesene, commercially available from Amyris, Inc. (Emeryville, Calif.) may be pre-treated to eliminate impurities and then hydrogenated so that three of the four double bonds are reduced to single bonds.
  • the partially hydrogenated intermediate product is then subjected to an oligomerization reaction with a linear alpha olefin (LAO) using a catalyst such as BF 3 or a BF 3 complex.
  • LAO linear alpha olefin
  • a further intermediate product consisting of a mixture of hydrocarbons ranging from C10 to about C75, results.
  • This oligomeric mixture of hydrocarbons is then hydrogenated to reduce the amount of unsaturation.
  • the saturated hydrocarbon mixture is then distilled to obtain the targeted composition and finally blended to meet desirable base oil product specifications (such as kinematic viscosity at 40° C.) for the engine oil.
  • desirable base oil product specifications such as kinematic viscosity at 40° C.
  • Desirable examples of biobased base oil specifications that can be used to produce blends suitable for engine oil formulation for one embodiment are set forth in Table I.
  • a commercially available biobased hydrocarbon base oil (a hydrogenated reaction product between a partially hydrogenated ⁇ -3,7,11-trimethyldodeca-1,3,6,10-tetraene and a linear C8-C16 alpha olefin, hydrogenated) sold under the commercial designation NOVASPEC (Novvi LLC, Emeryville, Calif., United States; (REACH registration number 01-2120031429-59-0000), is used.
  • At least about 20% of the carbon atoms in the base oil comprised by an engine oil originate from renewable carbon sources.
  • at least about 30% of the carbon atoms in the base oil comprised by an engine oil originate from renewable carbon sources.
  • at least about 40% of the carbon atoms in the base oil comprised by an engine oil originate from renewable carbon sources.
  • at least about 50% of the carbon atoms in the base oil comprised by an engine oil originate from renewable carbon sources.
  • at least about 60% of the carbon atoms in the base oil comprised by an engine oil originate from renewable carbon sources.
  • At least about 70% of the carbon atoms in the base oil comprised by an engine oil originate from renewable carbon sources.
  • at least about 80% of the carbon atoms in the base oil comprised by an engine oil originate from renewable carbon sources.
  • at least about 90% of the carbon atoms in the base oil comprised by an engine oil originate from renewable carbon sources.
  • the carbon atoms of the base oil component of the engine oil comprises at least about 95%, at least about 97%, at least about 99%, or about 100% of originate from renewable carbon sources.
  • the origin of carbon atoms in the reaction product adducts may be determined by any suitable method, including but not limited to reaction mechanism combined with analytical results that demonstrate structure and/or molecular weight of adducts, or by carbon dating (e.g., according to ASTM D6866-12 “Standard Test Methods for Determining the Biobased Content of Solid, Liquid, and Gaseous Samples Using Radiocarbon Analysis,” which is incorporated herein by reference in its entirety).
  • a ratio of carbon 14 to carbon 12 isotopes in the biobased base oil can be measured by liquid scintillation counting and/or isotope ratio mass spectroscopy to determine the amount of modern carbon content in the sample.
  • a measurement of no modern carbon content indicates all carbon is derived from fossil fuels.
  • a sample derived from renewable carbon sources will indicate a concomitant amount of modern carbon content, up to 100%.
  • one or more repeating units of biobased hydrocarbon base oil are specific species of partially hydrogenated conjugated hydrocarbon terpenes.
  • Such specific species of partially hydrogenated conjugated terpenes may or may not be produced by a hydrogenation process.
  • a partially hydrogenated hydrocarbon terpene species is prepared by a method that includes one or more steps in addition to or other than catalytic hydrogenation.
  • Non-limiting examples of specific species partially hydrogenated conjugated hydrocarbon terpenes include any of the structures provided herein for dihydrofarnesene, tetrahydrofarnesene, and hexahydrofarnesene; any of the structures provided herein for dihydromyrcene and tetrahydromyrcene; and any of the structures provided herein for dihydroocimene and tetrahydroocimene.
  • One example of a particular species of partially hydrogenated conjugated hydrocarbon terpene that may have utility as a feedstock is a terminal olefin having a saturated hydrocarbon tail with structure (A11):
  • n 1, 2, 3, or 4.
  • a mono-olefinic alpha-olefin having structure A11 may be derived from a conjugated hydrocarbon terpene wherein the conjugated diene is at the 1,3-position of the terpene.
  • Examples include alpha-olefins derived from a 1,3-diene conjugated hydrocarbon terpene (e.g., a C10-C30 conjugated hydrocarbon terpene such as farnesene, myrcene, ocimene, springene, geranylfarnesene, neophytadiene, trans-phyta-1,3-diene, or cz's-phyta-I, 3-diene).
  • Another non-limiting example of an alpha-olefin having the general structure A11 includes 3,7,11-trimethyldodecene having structure A12.
  • a mono-olefinic alpha-olefin having structure A11 may be prepared from the appropriate conjugated hydrocarbon terpene using any suitable method.
  • the mono-olefinic alpha-olefin having structure A11 is produced from primary alcohol of corresponding to the hydrocarbon terpene (e.g., farnesol in the case of farnesene, or geraniol in the case of myrcene).
  • the methods comprise hydrogenating the primary alcohol, forming a carboxylic acid ester or carbamate ester from the hydrogenated alcohol, and pyrolizing the ester (or heating the ester to drive the elimination reaction) to form the alpha-olefin with a saturated hydrocarbon tail, e.g., as described in Smith, L.
  • Alpha-olefins having the general structure A11 from conjugated hydrocarbon terpenes may be prepared via other schemes.
  • the hydrocarbon terpene has a conjugated diene at the 1,3-position, and the conjugated diene can be functionalized with any suitable protecting group known to one of skill in the art in a first step (which may comprise one reaction or more than one reaction).
  • the remaining olefinic bonds can be saturated in a second step (which may comprise one reaction or more than one reaction), and the protecting group can be eliminated to produce an alpha-olefin having the general structure A11 in a third step (which may comprise one reaction or more than one reaction).
  • a hydrocarbon terpene having a 1,3-conjugated diene may be reacted with an amine (e.g., a dialkyl amine such as dimethylamine or diethylamine) in the first step to produce an amine having the formula N(R 1 )(R 2 )(R 3 ), where R 1 and R 2 are alkyl groups such as methyl or ethyl, and R 3 is an unsaturated hydrocarbon originating from the conjugated terpene.
  • an amine e.g., a dialkyl amine such as dimethylamine or diethylamine
  • the resulting amine may be oxidized to the N oxide using hydrogen peroxide (H 2 O 2 ) followed by elimination to the aldehyde using acetic anhydride. Hydrogenation of the aldehyde in the presence of a catalyst may be carried out to saturate any remaining olefinic bonds on the aliphatic tail originating from the hydrocarbon terpene, and the aldehyde functionality may be eliminated to produce an alpha-olefin having structure A11.
  • Scheme I illustrates an example of such a preparation of an alpha-olefin having structure A11 using ⁇ -farnesene as a model compound.
  • the amine N(R 1 )(R 2 )(R 3 ) can be hydrogenated (e.g., using an appropriate catalyst), treated with hydrogen peroxide, and heated to undergo elimination to form an alpha-olefin having structure A11 (e.g., compound A12 if ⁇ -farnesene is used as the starting hydrocarbon terpene).
  • Scheme II illustrates this method using ⁇ -farnesene as a model compound.
  • a hydrogenated primary alcohol corresponding to a hydrocarbon terpene e.g., hydrogenated farnesol or hydrogenated geraniol
  • a hydrogenated primary alcohol corresponding to a hydrocarbon terpene can be dehydrated using basic aluminum oxide (e.g., at a temperature of about 250° C.) to make an alpha-olefin having the general structure A11.
  • basic aluminum oxide e.g., at a temperature of about 250° C.
  • a hot tube reactor e.g., at 250° C.
  • hydrogenated farnesol can be dehydrated using basic aluminum oxide (e.g., in a hot tube reactor at 250° C.) to make compound A12, or an isomer thereof.
  • a mono-olefin having the general structure A13, A15 or A11 may in certain instances be derived from a conjugated hydrocarbon terpene having a 1,3-diene moiety, such as myrcene, farnesene, springene, geranylfarnesene, neophytadiene, trans-phyta-1,3-diene, or cis-phyta-1,3-diene.
  • the conjugated may be functionalized with a protecting group (e.g., via a Diels-Alder reaction) in a first step, exocyclic olefinic bonds hydrogenated in a second step, and the protecting group eliminated in a third step.
  • a conjugated hydrocarbon terpene having a 1,3-diene is reacted with SO 2 in the presence of a catalyst to form a Diels-Alder adduct.
  • the Diels-Alder adduct may be hydrogenated with an appropriate hydrogenation catalyst to saturate exocyclic olefinic bonds.
  • a retro Diels-Alder reaction may be carried out on hydrogenated adduct (e.g., by heating, and in some instances in the presence of an appropriate catalyst) to eliminate the sulfone to form a 1,3-diene.
  • the 1,3-diene can then be selectively hydrogenated using a catalyst known in the art to result in a mono-olefin having structure A11, A13 or A15, or a mixture of two or more of the foregoing.
  • a catalyst known in the art to result in a mono-olefin having structure A11, A13 or A15, or a mixture of two or more of the foregoing.
  • Non-limiting examples of regioselective hydrogenation catalysts for 1,3-dienes are provided in Jong Tae Lee et al, “Regioselective hydrogenation of conjugated dienes catalyzed by hydridopentacyanocobaltate anion using ⁇ -cyclodextrin as the phase transfer agent and lanthanide halides as promoters,” J. Org. Chem., 1990, 55 (6), pp. 1854-1856, in V. M.
  • 13-farnesene can be reacted with SO 2 in the presence of a catalyst to form a Diels-Alder adduct, which is subsequently hydrogenated, and the sulfone eliminated to form a 1,3-diene, which is subsequently selectively hydrogenated using a catalyst known in the art for regioselective hydrogen additions to 1,3-dienes to form 3,7,1 1-trimethyldodec-2-ene, 3,7,11-trimethyldodec-1-ene, or 3-methylene-7,11-dimethyldodecane, or a mixture of any two or more of the foregoing.
  • a terminal olefin of the general structure A14 may be made from a conjugated hydrocarbon terpene having a 1, 3-conjugated diene and at least one additional olefinic bond (e.g., myrcene, farnesene, springene, or geranylfarnesene):
  • a compound having the structure A14 may be derived from an unsaturated primary alcohol corresponding to the relevant hydrocarbon terpene (e.g., farnesol in the case of farnesene, or geraniol in the case of myrcene).
  • the unsaturated primary alcohol may be exposed to a suitable catalyst under suitable reaction conditions to dehydrate the primary alcohol to form the terminal olefin A 14.
  • a stoichiometric deoxygenation-reduction reaction may be conducted to form compounds having structure A14 from a primary alcohol (e.g., farnesol or geraniol) of a hydrocarbon terpene.
  • a primary alcohol e.g., farnesol or geraniol
  • One prophetic example of such a reaction can be conducted according to a procedure described in Dieguez et al, “Weakening C-0 Bonds: Ti(III), a New Reagent for Alcohol Deoxygenation and Carbonyl Coupling Olefination,” J. Am. Chem . Soc. 2010, vol. 132, pp.
  • a mixture of titanocene dichloride ( ⁇ 5 -C 5 H 5 ) 2 TiCl 2 (Cp 2 TiCl 2 ) (3.88 mmol) and Mn dust (2.77 mmol) in strictly deoxygenated tetrahydrofuran (THF) (7 mL) can be heated at reflux under stirring until the red solution turns green. Then, to this mixture can be added a solution of the primary alcohol (e.g., farnesol or geraniol) (1.85 mmol) in strictly deoxygenated THF (4 mL).
  • the primary alcohol e.g., farnesol or geraniol
  • reaction can be quenched with 1N HCI and extracted with tert-butylmethyl ether (t-BuOMe).
  • t-BuOMe tert-butylmethyl ether
  • the organic phase can be washed with brine, filtered and concentrated in vacuo to yield a crude product, which can be purified, e.g., by column chromatography (hexane/t-BuOMe, 8:1) over silica gel column to afford a compound having structure A14 (e.g., 3,7,11-trimethyldodeca-1,6,10-triene if farnesol is used as the starting material).
  • reaction may be conducted to form compounds having structure A14 from a primary alcohol (e.g., farnesol or geraniol) of a hydrocarbon terpene.
  • a primary alcohol e.g., farnesol or geraniol
  • One prophetic example of such a reaction can be conducted according to another procedure described in Dieguez et al, “Weakening C-0 Bonds: Ti(III), a New Reagent for Alcohol Deoxygenation and Carbonyl Coupling Olefination,” J. Am. Chem . Soc. 2010, vol. 132, pp.
  • the resulting crude may be purified, e.g., by column chromatography (hexane/t-BuOMe, 8:1) on silica gel to afford compound having structure A14 (e.g., 3,7,11-trimethyldodeca-1,6,10-triene if farnesol is used as the starting material).
  • column chromatography hexane/t-BuOMe, 8:1
  • silica gel e.g., 3,7,11-trimethyldodeca-1,6,10-triene if farnesol is used as the starting material.
  • An olefinic feedstock as described herein may comprise any useful amount of the particular species (e.g., alpha-olefinic species having structure A11, A12 or A15, mono-olefinic species having structure A13, or unsaturated terminal olefin species having structure A14), made either by a partial hydrogenation route or by another route, e.g., as described herein.
  • an olefinic feedstock comprises at least about 1%, at least about 5%, at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, or at least about 90% species having structure A11, A12, A13, A14, or A15.
  • an olefinic feedstock comprises at least about 1%, at least about 5%, at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, or at least about 90% 3,7,11-trimethyldodec-1-ene.
  • an olefinic feedstock comprises at least about 1%, at least about 5%, at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, or at least about 90% 3-methylene-7,11-dimethyldodecane.
  • an olefinic feedstock comprises at least about 1%, at least about 5%, at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, or at least about 90% 3,7,11-trimethyldodec-2-ene.
  • an olefinic feedstock comprises at least about 1%, at least about 5%, at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, or at least about 90% 3,7,11-trimethyldodeca-1,6,10-triene.
  • an olefinic feedstock comprises at least about 1%, at least about 5%, at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, or at least about 90% 3,7-dimethyloct-1-ene. In certain variations, an olefinic feedstock comprises at least about 1%, at least about 5%, at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, or at least about 90% 3,7-dimethyloct-2-ene.
  • an olefinic feedstock comprises at least about 1%, at least about 5%, at least about 10%, at least about 20%, at least about 30%, at least about 40%, at least about 50%, at least about 60%, at least about 70%, at least about 80%, or at least about 90% 3,7-dimethylocta-1,6-diene.
  • the hydrocarbon terpene feedstock comprising alpha-olefinic species or internal olefinic species of partially hydrogenated hydrocarbon terpenes are suitable for catalytic reaction with one or more alpha-olefins to form a mixture of isoparaffins comprising adducts of the terpene and the one or more alpha-olefins.
  • at least a portion of the mixture of isoparaffins so produced may be used as a base oil.
  • API Group I, II, and III represent base oils which are differentiated by viscosity index, saturate content, and sulfur content.
  • Group III base oils have greater than 90% saturates, less than 0.03% sulfur and have a viscosity index above 120 due to higher degree of refinement than Group II base oils and generally are severely hydrocracked (higher pressure and heat).
  • the biobased base oils of current disclosure belong to API Group III base oil category.
  • Base oils from different groups provide distinguishably different performance of engine oil during engine testing. Therefore, simple and straightforward replacement of one base oil with another base oil comes with risks to proper engine operation.
  • the API base oil interchangeability guidelines (BOI) were developed to ensure that the performance of engine oil products is not adversely affected when different base oils are used interchangeably by engine oil blenders.
  • the API BOI guidelines are based on actual engine test data, using different base oils, for both gasoline and diesel engine oil performance. API BOI guidelines require the least amount of engine testing when the interchange base oil is selected from same API group as the base oil in the original tested engine oil formulation.
  • wt % about 25 weight percent (wt %) up to about 95 wt % of the biobased hydrocarbon base oil may be used.
  • wt % additives namely one or more oxidation inhibitors (anti-oxidants), corrosion and rust inhibitors, viscosity modifiers, pour point depressants, metal deactivators, anti-foaming agents, friction modifiers, extreme pressure additives, anti-wear agents, dispersants, detergents, commercially available engine oil additive packages, and mixtures thereof.
  • a range of typical dosage level and preferred dosage level of such additives are shown in Table III.
  • a blend component comprising one or more additional base oils or liquids may also be used as the base oil or co-base oil to formulate or complete the engine oil, or to adjust the viscosity of the engine oil or some other desired characteristic.
  • additive oils, co-base oils, or liquids may be selected from one or more of the following: microbial oils, castor oil, lard oil, vegetable oils, seed oils, algal oils, mineral oils, highly refined mineral oils, isoparaffinic hydrocarbon fluids, naphthenic oils, silicone fluids, synthetic esters, poly alpha olefins, PAG's, phosphate esters, silicon oils, diesters, polyol esters, polysiloxanes, pentaerythritol esters, alkylated naphthalene, poly(butene) liquids, polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, poly(1-hexenes), poly(1-o
  • dodecylbenzenes dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di(2-ethylhexyl) benzenes), estolides, polyphenols (e.g. biphenyls, terphenyls, alkylated polyphenols), alkylated diphenyl ethers, alkylated diphenyl sulfides and combinations thereof.
  • polyphenols e.g. biphenyls, terphenyls, alkylated polyphenols
  • alkylated diphenyl ethers alkylated diphenyl sulfides and combinations thereof.
  • Another suitable class of co-base oils comprises the esters of dicarboxylic acids (e.g. phthalic acid, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebasic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkylmalonic acids, alkenylmalonic acids) with a variety of alcohols (e.g. butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol mono ether, propylene glycol).
  • dicarboxylic acids e.g. phthalic acid, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebasic acid, fumaric acid, adipic acid, linoleic acid dimer
  • esters include dibutyl adipate, di(2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, the 2-ethylhexyl diester of linoleic acid dimer, and the complex ester formed by reacting one mole of sebacic acid with two moles of tetraethylene glycol and two moles of 2-ethylhex-anoic acid.
  • Esters useful as synthetic oils also include those made from C5 to C12 monocarboxylic acids and polyols, and polyol ethers such as neopentyl glycol, trimethylolpropane, pentaerythritol, dipentaerythritol and tripentaerythritol.
  • Unrefined, refined and re-refined oils can be used as co-base oils in the engine oil compositions of the present disclosure.
  • Unrefined oils are those obtained directly from a natural or synthetic source without further purification treatment.
  • a shale oil obtained directly from retorting operations a petroleum oil obtained directly from distillation or ester oil obtained directly from an esterification process and used without further treatment would be unrefined oil.
  • Refined oils are similar to the unrefined oils except they have been further treated in one or more purification steps to improve one or more properties. Many such purification techniques, such as distillation, solvent extraction, acid or base extraction, filtration and percolation are known to those skilled in the art.
  • Re-refined oils are obtained by processes similar to those used to obtain refined oils, but the processes are applied to refined oils which have been already used in service. Such re-refined oils are also known as reclaimed or reprocessed oils and often are additionally processed by techniques for approval of spent additive and oil breakdown products.
  • co-base oils are gas-to-liquid (“GTL”) base oils, i.e. the base oil may be an oil derived from FischerTropsch synthesized hydrocarbons made from synthesis gas containing H2 and CO using a Fischer-Tropsch catalyst. These hydrocarbons typically require further processing in order to be useful as a base oil. For example, they may, by methods known in the art, be hydroisomerized; hydrocracked and hydroisomerized; dewaxed; or hydroisomerized and dewaxed.
  • GTL gas-to-liquid
  • biobased oils may be used as a base oil in a similar manner, with attention to viscosity as with the biobased hydrocarbon base oil.
  • the engine oil composition comprises an anti-oxidant.
  • Antioxidants are typically free-radical traps, acting as free-radical reaction chain breakers. That is, effective antioxidants may be selected from radical scavengers such as phenolic, aminic antioxidants, or synergistic mixtures of these. Sulfurized phenolic antioxidants and organic phosphites are useful as components of such mixtures. Many antioxidant additives that are known and used in the formulation of lubricant products are suitable for use with the engine oils formulation described in this disclosure.
  • phenolic antioxidants examples include 2,6-di-tert-butylphenol, liquid mixtures of tertiary butylated phenols, 2,6-di-tert-butyl-4-methylphenol, 4,4′-methylenebis(2,6-di-tert-butylphenol), 2,2′-methylenebis(4-methyl6-tert-butylphenol), mixed methylene-bridged polyalkyl phenols, 4,4′-thiobis(2-methyl-6-tert-butylphenol), 4,4′-butylidene-bis(3-methyl-6-tert-butylphenol), 4,4′-isopropylidene-bis(2,6-di-tert-butylphenol), 2,2′-methylene-bis(4-methyl-6-nonylphenol), 2,2′-isobutylidene-bis(4,6-dimethylphenol), 2,6-di-tert-butyl-4-methylphenol, 2,6-di-tert-
  • the antioxidant is an organic phosphonate having at least one direct carbon-to-phosphorus linkage.
  • Diphenylamine-type oxidation inhibitors include, but are not limited to, alkylated diphenylamine, phenyl-alpha-naphthylamine, and alkylated-alpha-naphthylamine.
  • Other types of oxidation inhibitors include metal dithiocarbamate (e.g., zinc dithiocarbamate), and 15-methylenebis(dibutyldithiocarbamate).
  • class of antioxidants suitable for food grade industrial lubricant formulation are also useful in the compressor oil described in current disclosure.
  • antioxidants include, without limitation, butylated hydroxyanisole (BHA), di-butyl-paracresol (BHT), phenyl-a-naphthylamine (PANA), octylated/butylated diphenylamine, tocopherol (vitamin-E), ⁇ -carotene, sterically hindered alkylthiomethylphenol, 2-(1,1-Dimethylethyl)-1,4-benzenediol, l,2-dihydro-2,2,4-trimethylquinoline, ascorbyl palmitate, propyl gallate, high molecular weight phenolic antioxidants, hindered bis-phenolic antioxidant, and mixtures of these.
  • BHA butylated hydroxyanisole
  • BHT di-butyl-paracresol
  • PANA phenyl-a-naphthylamine
  • Metal deactivators/passivator may also be used in addition to or as an alternative to an antioxidant.
  • the list of useful metal deactivators include imidazole, benzimidazole, pyrazole, benzotriazole, tolutriazole, 2-methyl benzimidazole, 3,5-dimethyl pyrazole, and methylene bis-benzotriazole.
  • Commercial examples used in some embodiments of the disclosure include, without limitation, triazole derivative metal deactivators, such as Irgamet® 30 (available from BASF), and tolutriazole derivative metal deactivators, such as Irgamet® 39 (available from BASF)
  • An amount of metal deactivators up to about 100 ppm is used in some embodiments.
  • the metal passivator is food grade and complies with FDA regulations.
  • One of such useful additive is the N-acyl derivative of sarcosine, such as an N-acyl derivative of sarcosine.
  • N-acyl derivative of sarcosine such as an N-acyl derivative of sarcosine.
  • N-methyl-N-(1-oxo-9-octadecenyl) glycine is commercially available from BASF under the trade name SARKOSYLTM O.
  • Another additive is an imidazoline such as Amine OTM, also, commercially available from BASF.
  • the engine oils of the present disclosure comprise a foam inhibitor.
  • foam inhibitors include but are not limited to alkylpolysiloxanes, dimethyl polycyclohexane and polyacrylates.
  • Commercial examples useful foam inhibitors in some embodiments of the disclosure include, without limitation, PC-1344 (Cytec), PC-1844 (Cytec), PC-2544 (Cytec), PC-3144 (Cytec), HiTec2030 (Afton), AC AMH2 (BASF), 889D (Lubrizol), and mixtures thereof.
  • the engine oils of the present disclosure comprise a viscosity modifier/viscosity index improver.
  • Viscosity modifiers are polymeric materials, typical examples of these being hydrogenated styrene-isoprene block copolymers, hydrogenated copolymers of styrene-butadiene, copolymers of ethylene and propylene, acrylic polymers produced by polymerization of acrylate and methacrylate esters, hydrogenated isoprene polymers, polyalkyl styrenes, hydrogenated alkenyl arene conjugated diene copolymers, polyolefins, esters of maleic anhydride-styrene copolymers, and polyisobutylene. These polymeric thickeners are added to bring the viscosity of the base fluid mixture up to the required level of SAE J300 viscosity grade (see, e.g., Table IV).
  • the viscosity modifier/viscosity index improver may be a polymer with linear, radial or star architecture, such as those described in Schober et al., US Patent Application No. 2011/0306529, which is incorporated by reference in its entirety, and in the references cited therein, all of which are incorporated herein in their entirety.
  • Such viscosity modifiers may have a random, tapered, di-block, tri-block, or multi-block architecture and may have weight average molecular weights of about 100,000 to about 800,000 g/mol.
  • 2011/0306529 is prepared from 50 wt % to about 100 wt % of an alkyl methacrylate, wherein the alkyl group has about 10 to about 20 carbon atoms up to about 40 wt % of an alkyl methacrylate, wherein the alkyl group has about 9 carbon atoms; and up to about 10 wt % of a nitrogen-containing monomer.
  • Other examples of viscosity modifiers that are star polymers include isoprene/styrene/isoprene triblock polymers.
  • Examples of commercially available viscosity modifier/viscosity index improver for use in some embodiments of the disclosure include, without limitation, TPC1285 (TPC group), TPC175 (TPC group), TPC1105 (TPC group), TPC1160 (TPC group), SV260 (Infineum), SV261 (Infineum), SV265 (Infineum), V534 (Infineum), 7308 (Lubrizol), 7723 (Lubrizol), 87705 (Lubrizol), HiTec5754 (Afton), HiTec5751 (Afton), HiTec5748 (Afton), HiTec5825A (Afton), Viscoplex 8-100 (Evonik), Viscoplex 8-112 (Evonik), Viscoplex 8-200 (Evonik), Viscoplex 8-219 (Evonik), Viscoplex 8-220 (Evonik), Viscoplex 8-251 (Evonik), Viscoplex 8-310 (Evonik), Viscoplex 8-400 (
  • the engine oils of the present disclosure comprise detergents or dispersants which can be anionic, cationic, zwitterionic or non-ionic.
  • a dispersant is typically an additive whose primary function is to hold solid and liquid contaminations in suspension, thereby passivating them and reducing engine deposits at the same time as reducing sludge depositions.
  • a dispersant maintains in suspension oil-insoluble substances that result from oxidation during use of the lubricant, thus preventing sludge flocculation and precipitation or deposition on metal parts of the engine.
  • Dispersants are usually “ashless”, as mentioned above being non-metallic organic materials that form substantially no ash on combustion, in contrast to metal-containing, and hence ash-forming materials.
  • ashless dispersants may comprise an oil-soluble polymeric backbone.
  • a preferred class of olefin polymers is polybutenes, specifically polyisobutenes (PIE) orpoly-n-butenes, such as may be prepared by polymerization of a C4 refinery stream.
  • Dispersants include, for example, derivatives of long-chain hydrocarbon-substituted carboxylic acids, examples being derivatives of high molecular weight hydrocarbyl-substituted succinic acid.
  • a noteworthy group of dispersants are hydrocarbon-substituted succinim ides, made, for example, by reacting the above acids (or derivatives) with a nitrogen-containing compound, advantageously by a polyalkylene polyamine, such as a polyethylene polyamine.
  • Particularly preferred are the reaction products of polyalkylene polyamines with alkenyl succinic anhydrides, such as described in U.S. Pat. Nos.
  • boration may be accomplished by treating an acyl nitrogen-containing dispersant with a boron compound selected from boron oxide, boron halides, boron acids and esters of boron acids.
  • Lubricant dispersants stabilize contaminants during lubrication cycle resulting in protection against problem such as viscosity increase, wear, and filter plugging.
  • the surfactant or dispersant may be used alone or in combination with other types of surfactants or dispersants. Examples include, but not limited to, metal-containing compounds such as phenates, salicylates, thiophosphonates, and sulfonates. Examples also include, but not limited to, ashless dispersants such as alkyl succinic anhydrides, succinimide dispersants, succinic ester dispersants, and succinic ester-amide dispersants.
  • the dispersant is selected from the group of alkenyl succinim ides, alkenyl succinimides modified with other organic compounds, alkenyl succinimides modified by post-treatment with ethylene carbonate or boric acid, pentaerythritols, phenate-salicylates and their post-treated analogs, alkali metal or mixed alkali metal, alkaline earth metal borates, dispersions of hydrated alkali metal borates, dispersions of alkaline-earth metal borates, polyamide ashless dispersants and the like or mixtures of such dispersants.
  • metallic detergents include an oil-soluble neutral or overbased salt of alkali or alkaline earth metal with one or more of the following acidic substance (or mixtures thereof): a sulfonic acid; a carboxylic acid; a salicylic acid; an alkyl phenol; a sulfurized alkyl phenol; and an organic phosphorus acid characterized by at least one direct carbon-to-phosphorus linkage, such as phosphonate.
  • a detergent is an additive that reduces formation of piston deposits, for example high-temperature varnish and lacquer deposits, in engines; it normally has acid-neutralizing properties and is capable of keeping finely divided solids in suspension.
  • Most detergents are based on metal “soaps”, that is, metal salts of acidic organic compounds.
  • Lubricant detergents are metal salts of organic surfactants giving corrosion protection, deposit prevention, and other formulation enhancement.
  • Detergents generally comprise a polar head with a long hydrophobic tail, the polar head comprising a metal salt of an acidic organic compound.
  • the salts may contain a substantially stoichiometric amount of the metal when they are usually described as normal or neutral salts and would typically have a total base number or TBN (as may be measured by ASTM D2896-11) of from 0 to 80.
  • TBN total base number
  • Large amounts of a metal base can be included by reacting an excess of a metal compound, such as an oxide or hydroxide, with an acidic gas such as 15 carbon dioxide.
  • the resulting overbased detergent comprises neutralized detergent as an outer layer of a metal base (e.g., carbonate) micelle.
  • Such overbased detergents may have a TBN of 150 or greater, typically from 250 to 500 or more.
  • Detergents that may be used include oil-soluble neutral and acids, overbased sulfonates, phenates, sulfurized phenates, iophosphonates, salicylates, and naphthenates and other oil-soluble carboxylates of a metal, particularly the alkali or alkaline earth metals, e.g. sodium, potassium, lithium, calcium and magnesium.
  • a metal particularly the alkali or alkaline earth metals, e.g. sodium, potassium, lithium, calcium and magnesium.
  • the most commonly used metals are calcium and magnesium, which may both be present in detergents used in a lubricant, and mixtures of calcium and/or magnesium with sodium.
  • Particularly convenient metal detergents are neutral and overbased calcium sulfonates and sulfurized phenates having a TBN of from 50 to 450.
  • the engine oils of the present disclosure further comprise at least one rust or corrosion inhibitor.
  • suitable ferrous metal corrosion inhibitors are the metal sulfonates such as calcium petroleum sulfonate, barium dionyl-naphthalene sulfonate and basic barium dioxonylnaphthalene sulfonate, carbonated or non-carbonated.
  • Other examples are selected from thiazoles, triazoles, and thiadiazoles.
  • Examples of such compounds include benzotriazole, tolyltriazole, octyltriazole, decyltriazole, dodecyltriazole, 2-mercapto benzothiazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercapto-5-hydrocarbylthio-1,3,4-thiadiazoles, 2-mercapto-5-hydrocarbyldithio-1,3,4-thiadiazoles, 2,5-bis(hydrocarbylthio)-1,3,4-thiadiazoles, and 2,5-bis(hydrocarbyldithio)-1,3,4-thiadiazoles.
  • Suitable compounds include the 1,3,4-thiadiazoles, a number of which are available as articles of commerce, and also combinations of triazoles such as tolyltriazole with a 1,3,5-thiadiazole such as 2,5-bis(alkyldithio)-1,3,4-thiadiazole.
  • the 1,3,4-thiadiazoles are generally synthesized from hydrazine and carbon disulfide by known procedures. See, for example, U.S. Pat. Nos. 2,765,289; 2,749,311; 2,760,933; 2,850,453; 2,910,439; 3,663,561; 3,862,798; and 3,840,549.
  • the rust or corrosion inhibitors are selected from the group of monocarboxylic acids and polycarboxylic acids.
  • monocarboxylic acids and polycarboxylic acids examples include octanoic acid, decanoic acid and dodecanoic acid.
  • Suitable polycarboxylic acids include dimer and trimer acids produced from acids such as tall oil fatty acids, oleic acid, linoleic acid, or the like.
  • rust inhibitor may comprise alkenyl succinic acid and alkenyl succinic anhydride corrosion inhibitors, for example, tetrapropenylsuccinic acid, tetrapropenylsuccinic anhydride, tetradecenylsuccinic acid, tetradecenylsuccinic anhydride, hexadecenylsuccinic acid, hexadecenylsuccinic anhydride, and the like.
  • half esters of alkenyl succinic acids having 8 to 24 carbon atoms in the alkenyl group with alcohols such as the polyglycols.
  • Suitable rust or corrosion inhibitors include ether amines; acid phosphates; amines; polyethoxylated compounds such as ethoxylated amines, ethoxylated phenols, and ethoxylated alcohols; imidazolines; aminosuccinic acids or derivatives thereof, and the like. Mixtures of such rust or corrosion inhibitors can be used.
  • Other examples of rust inhibitors include a polyethoxylated phenol, neutral calcium sulfonate and basic calcium sulfonate.
  • the engine oils of the present disclosure further comprise at least a friction modifier selected from the group of succinimide, a bis-succinimide, an alkylated fatty amine, an ethoxylated fatty amine, an amide, a glycerol ester, a glycerol mono-oleates, an imidazoline, fatty alcohol, fatty acid, amine, borated ester, other esters, phosphates, phosphites, phosphonates, and mixtures thereof.
  • a friction modifier selected from the group of succinimide, a bis-succinimide, an alkylated fatty amine, an ethoxylated fatty amine, an amide, a glycerol ester, a glycerol mono-oleates, an imidazoline, fatty alcohol, fatty acid, amine, borated ester, other esters, phosphates, phosphites, phosphonates, and mixtures thereof.
  • Extreme pressure/anti-wear agents useful for present disclosure may be selected from library of molecules deemed suitable/preferable by those who are skilled in art of engine oil formulation. Such molecules and compounds can reduce friction and/or wear by forming protective-film layer between two sliding surfaces. Such compounds include oxygen-containing organic compounds with polar head group, organic sulphur compounds which can form reacted films at surfaces, organic phosphorus compounds, organic boron compounds, organic molybdenum compounds, zinc dialkyldithiophosphates (ZDDP), and mixture thereof.
  • the engine oils further comprise at least an extreme pressure/anti-wear agent in the range of from 100 ppm to 1 wt %, based on the total weight of engine oil composition.
  • anti-wear agents include, but are not limited to, phosphates, carbarmates, esters, molybdenum-containing compounds, boron-containing compounds and ashless anti-wear additives such as substituted or unsubstituted thiophosphoric acids, and salts thereof.
  • the anti-wear agents are selected from the group of zinc dialkyl-1-dithiophosphate (primary alkyl, secondary alkyl, and aryl type), diphenyl sulfide, methyl trichlorostearate, chlorinated naphthalene, fluoroalkylpolysiloxane, lead naphthenate, neutralized phosphates, dithiophosphates, and sulfur-free phosphates.
  • the anti-wear agent is selected from the group of a zinc dialkyl dithio phosphate (ZDDP), an alkyl phosphite, a trialkyl phosphite, and amine salts of dialkyl and mono-alkyl phosphoric acid.
  • ZDDP zinc dialkyl dithio phosphate
  • alkyl phosphite alkyl phosphite
  • trialkyl phosphite amine salts of dialkyl and mono-alkyl phosphoric acid.
  • molybdenum-containing compounds that may serve as anti-wear agents include molybdenum dithiocarbamates, trinuclear molybdenum compounds, for example as described in WO1998026030, sulphides of molybdenum and molybdenum dithiophosphate.
  • Boron-containing compounds that may be used as anti-wear agents include borate esters, borated fatty amines, borated epoxides, alkali metal (or mixed alkali metal or alkaline earth metal) borates and borated overbased metal salts.
  • the engine oils of the present disclosure further comprise at least one seal compatibility agent. It is well known those who skilled in the art of engine oil and lubricant formulation that, when major portion of engine oil consists of highly paraffinic base oils, it is necessary to include seal compatibility agents in order to meet the specification. Seal compatibility agents may be selected from, but not limited to, various commercial grade aromatic esters.
  • the engine oils of the present disclosure comprise a pour point depressant.
  • a pour point depressant Such additives are well known.
  • Typical pour point depressant can be selected from C8 to C18 dialkyl fumarate/vinyl acetate copolymers and polyalkylmethacrylates.
  • the additional or additive components to the engine oil are added as a fully formulated additive package designed to meet various regional and global engine oil specifications.
  • Some of the above-mentioned additives can provide a multiplicity of effects; thus for example, a single additive may act as a dispersant as well as an oxidation inhibitor.
  • each additive when the engine oil contains one or more of the above-mentioned additives, each additive is typically blended into the base oil in an amount that enables the additive to provide its desired function. It may be desirable, although not essential, to prepare one or more additive concentrates comprising additives (concentrates containing at least one of above-mentioned additives sometimes being referred to as “additive packages”) to add to the engine oil composition.
  • the final composition may employ from about 0.001 to 20 wt. % of the concentrate, the remainder being the oil of lubricating viscosity.
  • the components can be blended in any order and can be blended as combinations of components.
  • Additives used in formulating the engine oil composition can be blended into the base oil individually or in various sub-combinations to subsequently form the engine oil.
  • all of the components are blended concurrently using an additive concentrate (i.e., additives plus a diluent, such as a group III base oils or group V base oils).
  • an additive concentrate i.e., additives plus a diluent, such as a group III base oils or group V base oils.
  • the engine oil composition is prepared by mixing the base oil with the separate additives or additive package(s) at an appropriate temperature, such as approximately 25 ⁇ 80° C., until homogeneous.
  • the engine oils of the present disclosure can be used in various types of internal combustion engines.
  • High temperature high shear (HTHS) viscosity of engine oils can serve as a fundamental indicator of fuel economy index (FEI) improvement and protection against mechanical wear inside modern day automotive engines.
  • HTHS viscosity may be measured by standardized method such as ASTM-D4683-13 or equivalent.
  • Lower HTHS viscosity tends to improve FEI but can be correlated to less protection against mechanical wear. Therefore, careful balance must be maintained in order to achieve best FEI while providing optimum protection against mechanical wear.
  • FIG. 1 compares HTHS value of base oils that belongs to different API group as a function of kinematic viscosity at 100° C. These base oils are main ingredients of commercial engine oils currently sold in the market.
  • FIG. 2 show same trend obtained from mixture of base oils mentioned above and viscosity modifier commercially used for engine oil formulations.
  • FIG. 2 shows existence of unique relationship between kinematic viscosity at 100° C. and HTHS at 150° C. regardless of identity of commercial engine oil grade hydrocarbon base oils used in blend with VMs. Blend of such VMs with biobased hydrocarbon base oils falls into same unique trend.
  • FIG. 1 plots the HTHS value of different base oils as a function of kinematic viscosity at 100° C.
  • FIG. 3 plots cranking viscosity, (in cP at ⁇ 35° C.), as a function of Noack volatility, measured as % weight loss.
  • the graph shows data of base oils selected from Group II, Group III and Group IV, as well as data for biobased hydrocarbon base oils; the cranking viscosity at subzero temperature was measured using ASTM-D5293-14 and Noack volatility was measured using the procedure of ASTM-D5800-10.
  • Group II base oils and their blends show highest cranking viscosity per given value of % volatile loss while group IV base oils and their blends show lowest cranking viscosity per given value of % volatile loss.
  • Biobased hydrocarbon base oils and Group III base oils show trend set between Group II and Group IV base oils.
  • Typical 0W-grade engine oil formulations that utilize commercially available additive packages require a cranking viscosity value of the base oil blends to be less than or equal to 3000 cP at ⁇ 35° C.
  • Table V shows the advantage of biobased isoparaffinic hydrocarbon base oils over petroleum based isoparaffinic hydrocarbon base oils. At given % volatile loss, 13%, Group II base oil blends have a much higher cranking viscosity, 16,668 cP, than the required 3,000 cP for 0W-grade engine oil formulations while Group IV based base oil blends have the lowest cranking viscosity, 540 cP.
  • the biobased hydrocarbon base oil blend with 13% volatile loss has a cranking viscosity lower than the required 3,000 cP.
  • Petroleum based isoparaffinic hydrocarbon base oils, Group III, with same amount of volatile loss have higher cranking viscosities than the required value for 0W-grade engine oil formulations.
  • the third column of Table V shows % volatile loss of base oil blends with cranking viscosities of 3,000 cP at ⁇ 35° C.
  • the biobased hydrocarbon base oil blend with 3,000 cP of cranking viscosity has a % volatile loss lower than the required 13% while the petroleum based isoparaffinic hydrocarbon base oil, Group III, with the same cranking viscosity has a higher % volatile loss, 14.2%, and exceeds the required 13%.
  • a higher amount of non/low-volatile ingredients i.e. viscosity modifiers and/or higher viscosity grade base oils
  • inclusion of such non-volatile ingredients typically comes with a disadvantages such as increased base kinematic viscosity and/or increased cranking viscosity at lower temperature.
  • Such disadvantages typically limits the range of viscosity grades that can be formulated (i.e. limited in formulating lower viscosity grades or lower winter grades) according to the SAE-J300 specification.
  • FIG. 4 compares cranking viscosity, at ⁇ 35° C., of base oils selected from Group II, Group III and Group IV to cranking viscosity of biobased hydrocarbon base oil as a function of kinematic viscosity at 100° C.; cranking viscosity was measured using the procedure of ASM-D5293-14 and kinematic visclosity was measure using the procedure of ASTM-D445-14E2.
  • cranking viscosity at ⁇ 35° C. ranks Group II>Group III>Group IV (from high value to low value).
  • Biobased hydrocarbon base oils and Group III base oils show trend set between Group II and Group IV base oils.
  • Kinematic viscosity at 100° C. is another important parameter in classifying engine oils (see, e.g., Table IV).
  • the simplest engine oil formulation that consists of an engine oil additive package and a base oil blend typically yields a SAE viscosity grade of between 20 or 30.
  • the addition of a viscosity modifier is necessary in order to formulate a higher viscosity grade engine oil such as grade 40 through 60 with the same base oil blend.
  • Viscosity modifier can easily boost kinematic viscosity with little or no increase on low temperature cranking viscosity. However, such benefit comes with a penalty of lower shear stability and higher formulation cost.
  • a base oil with lower cranking viscosity is preferred over a base oil having a greater cranking viscosity at a given kinematic viscosity at 100° C. and a base oil having a greater kinematic viscosity at 100° C. is preferred over a base oil having a lesser kinematic viscosity at 100° C. at a given cranking viscosity.
  • the second column of Table VI lists the cranking viscosity, at ⁇ 35° C., of base oil blends with a kinematic viscosity, at 100° C., value fixed at 4.7cSt.
  • Base oil blends made with Group II base oils has the highest cranking viscosity, 8438 cP and a base oil blend made with Group IV base oils has the lowest cranking viscosity, 2052 cP.
  • Petroleum based isoparaffinic hydrocarbon base oils, Group III with the same kinematic viscosity (4.7cSt at 100° C.) has a higher cranking viscosity than 3000 cP, the required value for a 0W-grade engine oil formulation. While a biobased hydrocarbon base oil blend with the same kinematic viscosity has a cranking viscosity of 2916 cP, this is lower than the requirement.
  • the last column of Table VI shows the kinematic viscosities at 100° C.
  • the Group IV base oil blend has the highest kinematic viscosity, 5.44cSt and the Group II base oil blend has the lowest kinematic viscosity, 3.46cSt.
  • Such a difference in the kinematic viscosity of the base oil blends typically requires additional 2 ⁇ 3 weight % of viscosity modifier in order to produce a final formulation with same kinematic viscosity.
  • the more viscosity modifier contained in a blend comes at the cost of lower shear stability and increased formulation cost.
  • the biobased hydrocarbon base oil blend with 3,000 cP of cranking viscosity has kinematic viscosity, at 100° C., of 4.74cSt which is higher than the base oil blend made with petroleum based isoparaffinic hydrocarbon, Group III, base oil that has a kinematic viscosity of 4.39cSt at 100° C.
  • kinematic viscosity at 100° C.
  • Table VII shows test results from bench top performance evaluation of exemplary engine oils formulated with biobased hydrocarbon base oils, commercial viscosity modifier, and commercially available engine oil additive packages.
  • Three 10W-30 engine oils have cranking viscosity at ⁇ 25° C. well below 7,000 cP and low temperature pumping viscosity well under 60,000 cP at ⁇ 30° C. which are required by SAE J300 specification.
  • Shear stability of all three examples were measured using ASTM-D6278-12E1 method and all fluids stay-in-grade after extensive shearing process prescribed by method.
  • High shear rate viscosity at 150° C. of all three formulation achieved minimum 3.5 cP as required by specification published under ACEA-A3/B3 and ACEA-A3/B4 which are intended for a use in high performance gasoline and light duty diesel engines and are typically used in newer vehicles.
  • Table VIII compares test results from bench top performance evaluation of exemplary engine oils formulated with biobased hydrocarbon base oils to engine oils formulated with Group II, Group III, and Group IV base oils. To demonstrate the effect of different types of base oil, each was were formulated with same amount of a commercial available viscosity modifier, and commercially available engine oil additive package. All formulations except Exp-EO.BL.6 meet the requirements of 0W-20 viscosity grade engine oil viscometric specifications. The engine oil formulated using Group II base oil, Exp-EO.BL.6 has a cranking viscosity at ⁇ 35° C. higher than the requirement of 6200 cP and therefore can only meet the requirement of 5W-20 viscosity grade.
  • cranking viscosity The influence of a base oil's cranking viscosity on the final formulation of an engine oil is evident.
  • the ranking of cranking viscosities at ⁇ 35° C. of the formulations on Table VIII reflects the same ranking of the cranking viscosities at ⁇ 35° C. seen in FIG.1.
  • Exp-EO.BL.6 formulated with Group II base oil, had the highest cranking viscosity at ⁇ 25° C. to ⁇ 35° C. while Exp-EO.BL.7, formulated with Group IV base oil had the lowest cranking viscosity.
  • Exp-EO.BL.4 formulated with biobased isoparaffinic hydrocarbon base oil, has a lower cranking viscosity than Exp-EO.BL.5, formulated with petroleum based isoparaffinic hydrocarbon base oil (Group III) at all temperatures examined.
  • Exp-EO.BL.6 All formulations, except Exp-EO.BL.6, had volatile loss less than 13%.
  • the ranking of % volatile loss of the formulations reflects a ranking of % volatile loss of the base oils seen in FIG. 3 .
  • Exp-EO.BL.7 formulated with Group IV base oil, had the lowest volatile loss, 9.2%.
  • Exp-EO.BL.4, formulated with a biobased hydrocarbon base oil had the second lowest volatile loss, 11.5%.
  • Exp-EO.BL.5, formulated with a Group III base oil had the second highest volatile loss, 12.4%.
  • 0W-20 engine oils formulated with biobased hydrocarbon base oils are compared to commercially available premium grade 0W-20 engine oils and 5W-20 engine oil in Table IX.
  • 0W-20 engine oil formulated with biobased hydrocarbon base oil of current disclosure compares well with low temperature and high temperature viscometric performance of commercially available premium grade 0W-20 engine oils. Cranking viscosities at low temperatures are a strong function of kinematic viscosity at 100° C. In order to provide a direct comparison each test sample was paired with a reference fluid that had a matching kinematic velocity at 100° C.
  • the 0W-20 engine oil formulated with biobased hydrocarbon base oils of the current disclosure show improved performance over the commercially available engine oils tested. Also, the 0W-20 engine oil formulated with biobased base oil provides less volatile loss than the Group II or Group III based commercial engine oils.
  • Table XI provides a comparison of test results from the bench top performance evaluation of an exemplary 0W-16 grade engine oils formulated with biobased hydrocarbon base oils to engine oil formulated with Group II, Group III, and Group IV base oils.
  • each of the formulations was formulated with same amount of a commercial viscosity modifier, and an engine oil additive package designed for mineral oil based engine oil formulation.
  • Exp-EO.BL.10 (Group III) meets all of the SAE J300 requirements but the volatile loss (Noack) was higher than the 13% limit.
  • Exp-EO.BL.11 (Group II) could not meet the SAE J300 specifications due to a higher than required cranking viscosity at ⁇ 35° C.
  • Exp-EO.BL.12 Group IV met all of the requirements of 0W-16 except the high shear rate viscosity at 150° C. was lower than required, 2.3 mPa-s.
  • Table XII provides a comparison between 0W-12 grade engine oils formulated with biobased hydrocarbon base oils and the same grade engine oils formulated with Group III base oils. All of the listed formulations in Table XII do not use a viscosity modifier as the blend between base oil(s) and the additive package provides the correct viscosities to be qualified as 0W-12 grade engine oil.
  • Exp-EO.BL.15 and Exp-EO.BL.16 are the simplest blends to produce as they have only two ingredients, base oil and additive package. Both formulations may qualify for the proposed 0W-12 grade engine formulation based on the viscometric properties.
  • Exp-EO.BL.15 produced with the biobased isoparaffinic hydrocarbon base oil, shows improved performance over Exp-EO.BL.16, which was produced with Group III base oil (isoparaffinic hydrocarbon base oil produced from petroleum).
  • Exp-EO.BL.15 has lower cranking viscosity, lower volatile loss, and a better fuel economy index based on high shear rate viscosity.
  • the volatile loss of Exp-EO.BL.16 is at a failing level >13% loss while Exp-EO.BL.15 has a passing level ⁇ 13% loss.
  • Exp-EO.BL.14 shows improved volatility (meaning less volatile loss) than Exp-EO.BL.16 while maintaining passing grade viscometric performances.
  • a formulation with matching kinematic viscosities (at 40° C. and 100° C.) using a 7cSt biobased hydrocarbon base oil, Exp-EO.BL.13 also shows improved volatility over Exp-EO.BL.15 while maintaining good passing level viscometric properties.
  • Exp-EO.BL.13 also shows lower cranking viscosity, lower volatile loss, better low temperature pumpability, and better fuel economy index based on high shear rate viscosity than Exp-EO.BL.14.
  • Oxidative stability of an engine oil and its ability to endure harsh condition inside a modern internal combustion engine is another important performance parameter for engine oils.
  • the oxidative stability comparison of engine oils on Table VIII and Table IX were performed in an open-air reactor at an elevated temperature, 167° C., with soluble iron catalyst.
  • FIG. 5 shows the % viscosity increase as a function of time under conditions described above on Exp-EO.BL.4, Exp-EO.BL.5, Exp-EO.BL.6, and Exp-EO.BL.7. In such tests, the sample is typically considered to have failed to maintain its original functionality as an engine oil when viscosity increase is more than 200% from its starting viscosity.
  • Exp-EO.BL.6 engine oil formulated with Group II base oil, shows more than 200% viscosity increase around 480 hrs of aging.
  • FIG. 6 compares the oxidative stability of 0W-20 engine oil formulated with biobased hydrocarbon base oils, Exp-EO.BL.4, to commercially available premium grade 0W-20 engine oils and 5W-20 engine oil using the same conditions described in previous paragraph.
  • Comm-EO.1 is a standard grade 5W-20 engine oil, exhibited more than 200% viscosity increase around 310 hrs of aging.
  • Comm-EO.4 is a premium grade 0W-20 engine oil with advanced fuel economy label it had more than 200% viscosity increase after 510 hrs of aging.
  • Table XIII lists the bench top tests required by American Petroleum Institute (API) on passenger car engine oils for SN and GF-5 specification by International Lubricant Standardization and Approval Committee (ILSAC).
  • API American Petroleum Institute
  • IMSAC International Lubricant Standardization and Approval Committee
  • Table XIV shows the composition and performance of an exemplary 0W-30 engine oil formulated using biobased isoparaffinic hydrocarbon base oils discussed in the current disclosure. Performance was evaluated using a series of engine tests required to be certified for API SN/ILSAC GF-5 engine oil.
  • the engine oil in this example demonstrates great viscometric properties and passes Sequence IIIG with an outstanding viscosity retention result. The same engine oil also passed Sequence IVA and VG with strong performances.
  • the engine oils of this disclosure provide a number of advantages. In some embodiments, they are more biodegradable and have significantly more renewable content than Group I, Group II, Group III, and Group IV petroleum or natural gas derived oils based engine oil. In some embodiments, they have lower toxicity than Group I, Group II, Group III, and Group IV based oil engine oils. In some embodiments, they also demonstrate better hydrolytic stability and oxidation resistance than ester or vegetable oil based engine oils. In some embodiments, the engine oils of this disclosure also have better low temperature performance (lower cranking viscosity at ⁇ 35° C. and lower pour point as measured by ASTM-D5293-14) than esters/vegetable oil engine oils and also than some mineral oil based engine oils.
  • the engine oils of this disclosure also have lower Noack volatility than Group I, Group II, Group III, and IV petroleum or natural gas derived oils based engine oil as determined by ASTM-D5800-10 method B. Additionally, in some embodiments the engine oils of this disclosure provide better seal compatibility than vegetable or ester derived engine oils.
  • PAO poly alpha olefin
  • API The American Petroleum Institute
  • PAO base oil can only achieve less than 35% of biodegradation in 28 days when its kinematic viscosity (at 40° C.) is greater than 31cSt.
  • FIG. 7 compares biodegradability of different types of base oils using the OECD 301B method, which is considered to be part of the environmental performance matrix.
  • base oils with similar kinematic viscosity are compared (31cSt 37cSt at 40° C., noted in FIG. 7 ).
  • Tests were extended to 40 days to prove long term behavior rather than the standard period of 28 days. Slightly greater than 10 days of lag phase was observed from the biodegradation of PAO.
  • PAO showed 22% of biodegradation by 21 days and reached a plateau value, 27% biodegradation, by 25 days.
  • biobased base oils discussed in the test examples comprise a biobased hydrocarbon base oil.
  • biobased base oils not necessarily hydrocarbon based, but synthesized to have favorable properties, would also have the benefits of the biobased hydrocarbon base oil when used in engine oils formulation.
  • the foregoing examples demonstrate that the engine oils disclosed herein provide an engine oil that has superior or competitive properties to engine oils previously available.
  • the present disclosure further includes the following enumerated embodiments.
  • Embodiment 1 An engine oil comprising a biobased hydrocarbon base oil, wherein the engine oil meets the requirements of Engine Oil Viscosity Classification (J300) set by SAE and has a volatile loss of less than 13% when measured by ASTM D5800-10.
  • J300 Engine Oil Viscosity Classification
  • Embodiment 2 The engine oil of Embodiment 1 wherein the biobased hydrocarbon base oil has a molecular weight (weight average) between 300 g/mol and 1500 g/mol.
  • Embodiment 3 The engine oil of Embodiment 1 or 2 wherein at least about 25% of the carbon atoms in the biobased base oil originate from renewable carbon sources as measured by ASTM-D6866-12.
  • Embodiment 4 An engine oil comprising a biobased base oil, wherein the biobased base oil has greater than 90% saturates as measured by ASTM-D2007-11, less than 0.03% sulfur as measured by ASTM-D1552-08(2014)e1, ASTM D2622-10, ASTM D3120-08, ASTM D4294-10, ASTM D4927-10 or equivalent method, a viscosity index as measured by ASTM D2270-10e1 greater than 120, a renewable carbon content greater than 25% as measured by ASTM-D6866-12, contains a dispersant, a detergent, a corrosion inhibitor, an antioxidant, an antifoaming agent, an anti-wear agent, and a friction modifier, and wherein the engine oil has, when determined by ASTM-D7320-13, (a) a kinematic viscosity increase, at 40° C., of no more than 150%, (b) an average weighted piston deposit rating greater than 4.0, and (c) an average cam plus lifter wear of less than 60
  • Embodiment 5 An engine oil comprising a biobased Group III base oil, wherein the biobased Group III base oil has a renewable carbon content greater than 25% as measured by ASTM-D6866-12, contains a dispersant, a detergent, a corrosion inhibitor, antioxidant, an antifoaming agent, an anti-wear agent, and a friction modifier, and wherein the engine oil has, when determined by ASTM-D7320-13, (a) a kinematic viscosity increase, at 40° C., of no more than 150%, (b) an average weighted piston deposit rating greater than 4.0, and (c) an average cam plus lifter wear of less than 60 ⁇ m.
  • ASTM-D7320-13 contains a dispersant, a detergent, a corrosion inhibitor, antioxidant, an antifoaming agent, an anti-wear agent, and a friction modifier, and wherein the engine oil has, when determined by ASTM-D7320-13, (a) a kinematic viscosity increase, at 40° C.
  • Embodiment 6 An engine oil comprising a dispersant, a detergent, a corrosion inhibitor, antioxidant, an antifoaming agent, an antiwear agent, a friction modifier, and a biobased base oil, wherein the biobased base oil having the molecular structure:
  • Embodiment 7 The engine oil of Embodiment 6 wherein the molecular weight of the biobased base oil is in range of 300 g/mol to 800 g/mol.
  • Embodiment 8 The engine oil of Embodiment 6 wherein the molecular weight of the biobased base oil is in range of 390 g/mol to 510 g/mol.
  • Embodiment 9 An engine oil comprising a group III base oil, wherein the engine oil does not contain pour point depressant but contains a dispersant, a detergent, a corrosion inhibitor, an antioxidant, an antifoaming agent, an anti-wear agent, and a friction modifier, and wherein the engine oil has, when determined by ASTM-D7320-13, (a) a kinematic viscosity increase, at 40° C., of no more than 150%, (b) an average weighted piston deposit rating greater than 4.0, and (c) an average cam plus lifter wear of less than 60 ⁇ m.
  • Embodiment 10 An engine oil comprising: (a) at least 50 wt % of a biobased base oil having a weight average molecular weight in the range of 300 to 1500 g/mol and a viscosity index greater than 120; and (b) wherein the engine oil has,
  • Embodiment 11 The engine oil of Embodiment 10 wherein the engine oil has
  • Embodiment 12 The engine oil of Embodiment 10 wherein the engine oil has,
  • Embodiment 13 The engine oil of Embodiment 10 wherein the engine oil has
  • Embodiment 14 The engine oil of Embodiment 10 wherein the engine oil has
  • Embodiment 15 The engine oil of Embodiment 10 wherein the engine oil has
  • Embodiment 16 The engine oil of Embodiment 10 wherein the engine oil has
  • Embodiment 17 The engine oil of any of Embodiments 10-16, wherein the engine oil does not contain a pour point depressant.
  • Embodiment 18 The engine oil of any of Embodiments 10-16, wherein the engine oil does not contain a viscosity index improver or a viscosity modifier.
  • Embodiment 19 The engine oil of any of Embodiments 10-16, wherein the engine oil has less than 13% Noack volatility as measured by ASTM-D5800-10 method B.
  • Embodiment 20 The engine oil of any of the preceding enumerated Embodiments wherein the biobased base oil comprises at least 95% non-cyclic isoparaffins having a molecular structure in which 25-34% of total carbon atoms are contained in the branches and less than half of the total isoparaffin branches contain two or more carbon atoms and the engine oil has a renewable hydrocarbon content greater than 25%, as measured by ASTM-D6866 method.
  • Embodiment 21 The engine oil of any of the preceding enumerated Embodiments wherein the biobased base oil additionally has an average methyl branch index (methyl branches per 100 carbons) of at least 7.
  • Embodiment 22 The engine oil of any of the preceding enumerated Embodiments wherein the biobased base oil additionally has an average methyl branch index (methyl branches per 100 carbons) of at least 8.
  • Embodiment 23 The engine oil of any of the preceding enumerated Embodiments wherein the biobased base oil additionally has an average methyl branch index (methyl branches per 100 carbons) of at least 9.
  • Embodiment 24 The engine oil of any of the preceding enumerated Embodiments wherein the biobased base oil additionally has an average methyl branch index (methyl branches per 100 carbons) of at least 10.
  • Embodiment 25 The engine oil of any of the preceding enumerated Embodiments wherein the biobased base oil additionally has an average methyl branch index (methyl branches per 100 carbons) of at least 11.
  • Embodiment 26 The engine oil of any of the preceding enumerated Embodiments wherein the biobased base oil additionally has an average methyl branch index (methyl branches per 100 carbons) of at least 15.
  • Embodiment 27 The engine oil of any of the preceding enumerated Embodiments wherein the biobased base oil additionally has an average methyl branch index (methyl branches per 100 carbons) of at least 20.
  • Embodiment 28 The engine oil of any of the preceding enumerated Embodiments wherein the biobased base oil additionally has an average methyl branch index (methyl branches per 100 carbons) of at least 22.
  • Embodiment 29 The engine oil of any of the preceding enumerated Embodiments wherein the biobased base oil additionally has an average methyl branch index (methyl branches per 100 carbons) of at least 24.
  • Embodiment 30 The engine oil of any of the preceding enumerated Embodiments wherein the biobased base oil additionally has an average methyl branch index (methyl branches per 100 carbons) of at least 26.
  • Embodiment 31 The engine oil of any of the preceding enumerated Embodiments wherein the biobased base oil additionally has an average methyl branch index (methyl branches per 100 carbons) of at least 27.
  • Embodiment 32 The engine oil of any of the preceding enumerated Embodiments wherein at least 95 wt % of the biobased base oil comprises acyclic isoparaffins and at least 25 wt % of the acyclic isoparaffins are hydrogenated sesquiterpenoid monomer units.
  • Embodiment 33 The engine oil of Embodiment 32 wherein at least 30 wt % of the acyclic isoparaffins are hydrogenated sesquiterpenoid monomer units.
  • Embodiment 34 The engine oil of Embodiment 32 wherein at least 35 wt % of the acyclic isoparaffins are hydrogenated sesquiterpenoid monomer units.
  • Embodiment 35 The engine oil of Embodiment 32 wherein at least 45 wt % of the acyclic isoparaffins are hydrogenated sesquiterpenoid monomer units.
  • Embodiment 36 The engine oil of any of the preceding enumerated Embodiments wherein at least about 40% of the carbon atoms in the biobased base oil originate from renewable carbon sources as measured by ASTM-D6866-12.
  • Embodiment37 The engine oil of any of the preceding enumerated Embodiments wherein at least about 50% of the carbon atoms in the biobased base oil originate from renewable carbon sources as measured by ASTM-D6866-12.
  • Embodiment38 The engine oil of any of the preceding enumerated Embodiments wherein at least about 60% of the carbon atoms in the biobased base oil originate from renewable carbon sources as measured by ASTM-D6866-12.
  • Embodiment39 The engine oil of any of the preceding enumerated Embodiments wherein at least about 70% of the carbon atoms in the biobased base oil originate from renewable carbon sources as measured by ASTM-D6866-12.
  • Embodiment40 The engine oil of any of the preceding enumerated Embodiments wherein at least about 80% of the carbon atoms in the biobased base oil originate from renewable carbon sources as measured by ASTM-D6866-12.
  • Embodiment41 The engine oil of any of the preceding enumerated Embodiments wherein at least about 90% of the carbon atoms in the biobased base oil originate from renewable carbon sources as measured by ASTM-D6866-12.
  • Embodiment42 An engine oil comprising a biobased base oil, wherein the biobased base oil has greater than 50% of biodegradation in 28 days according to OECD 301B test method, the biobased base oil constitutes at least 50 wt % of the engine oil, and wherein the engine oil has, when determined by ASTM-D7320-13, (a) a kinematic viscosity increase, at 40° C., of no more than 150%, (b) an average weighted piston deposit rating greater than 4.0, and (c) an average cam plus lifter wear of less than 60 ⁇ m.
  • Embodiment43 The engine oil of any of the preceding enumerated Embodiments wherein the biobased base oil has greater than 50% of biodegradation in 28 days according to OECD 301B test method.
  • Embodiment44 The engine oil of any of the preceding enumerated Embodiments wherein the biobased base oil has greater than 60% of biodegradation in 28 days according to OECD 301B test method.
  • Embodiment45 The engine oil of any of the preceding enumerated Embodiments wherein the biobased base oil has greater than 70% of biodegradation in 28 days according to OECD 301B test method.
  • Embodiment 46 An engine oil comprising a biobased base oil and an additive package wherein (i) the engine oil and an otherwise identical engine oil comprising the additive package and a Group I, Group II or Group III base oil but no biobased base oil each satisfy the requirements of Engine Oil Viscosity Classification (J300) set by SAE and has a volatile loss of less than 13% when measured by ASTM D5800-10 and (ii) the engine oil even in the absence of additional solubilizer, co-base oil or co-solvent outperforms the otherwise identical engine oil in the Engine Oil Viscosity Classification (J300) and ASTM D5800-10 tests.
  • J300 Engine Oil Viscosity Classification
  • Embodiment 47 An engine oil comprising a biobased base oil and at least 0.1 wt % of an additive package comprising a dispersant, a detergent, a corrosion inhibitor, an antioxidant, an antifoaming agent, an antiwear agent, and a friction modifier, wherein the engine oil is compatible with engine oils formulated using Group I, Group II, or Group III base oil, meets requirements of Engine Oil Viscosity Classification (J300) set by SAE and has a volatile loss of less than 13% when measured by ASTM D5800-10.
  • J300 Engine Oil Viscosity Classification
  • Embodiment 48 An engine oil meeting performance requirements by SAE J300 specification, the engine oil comprising:
  • Embodiment 49 An engine oil according to any preceding enumerated Embodiment, wherein the biobased base oil is characterized by a viscosity index (VI) greater than 120, as measured in accordance with ASTM D2270-10e1, and has a branch ratio of less than 0.41.
  • VI viscosity index
  • Embodiment 50 An engine oil according to any preceding enumerated Embodiment, wherein the biobased base oil is characterized by a viscosity index (VI) greater than 120, as measured in accordance with ASTM D2270-10e1, and greater than 40% of the biobased base oil molecules have more than 3 methyl branch per molecule.
  • VI viscosity index
  • Embodiment51 The engine oil of Embodiment 50 wherein at least 50% of the biobased base oil molecules have more than 3 methyl branch per molecule.
  • Embodiment52 The engine oil of Embodiment 50 wherein at least 60% of the biobased base oil molecules have more than 3 methyl branch per molecule.
  • Embodiment 53 An engine oil according to any preceding enumerated Embodiment, wherein the biobased base oil is characterized by a viscosity index (VI) greater than 120, as measured in accordance with ASTM D2270-10e1, and greater than 25% of the biobased base oil molecules have more than 6 methyl branch per molecule.
  • VI viscosity index
  • Embodiment54 The engine oil of Embodiment 53 wherein at least 30% of the biobased base oil molecules have more than 3 methyl branch per molecule.
  • Embodiment55 The engine oil of Embodiment 53 wherein at least 40% of the biobased base oil molecules have more than 3 methyl branch per molecule.
  • Embodiment56 The engine oil of Embodiment 53 wherein at least 50% of the biobased base oil molecules have more than 3 methyl branch per molecule.
  • Embodiment57 The engine oil of Embodiment 53 wherein at least 60% of the biobased base oil molecules have more than 3 methyl branch per molecule.
  • Embodiment 58 The engine oil according to any preceding enumerated Embodiment wherein the engine oil contains about 2 to 50 wt % of one or more co-base oils selected from Group I, Group II, Group III, Group IV, Group V, and re-refined base oils, and combinations thereof.
  • Embodiment 59 The engine oil according to any preceding enumerated Embodiment wherein the engine oil contains a Group V co-base oil selected from alkylated aromatics, polyalkylene glycols, esters, estolides, and mixtures thereof.
  • a Group V co-base oil selected from alkylated aromatics, polyalkylene glycols, esters, estolides, and mixtures thereof.
  • Embodiment 60 The engine oil according to any preceding enumerated Embodiment wherein the engine oil comprises 5 to 50 wt % of a biobased hydrocarbon base oil and 1 to 50 wt % of one or more co-base oils, wherein the co-base oil(s) are selected from Group I, Group II, Group III, Group IV, and Group V base oils and combinations thereof.
  • Embodiment 61 The engine oil according to any preceding enumerated Embodiment wherein the engine oil comprises 5 to 50 wt % of a biobased hydrocarbon base oil and 1 to 50 wt % of one or more co-base oils, wherein the co-base oil(s) are selected from non biobased Group III base oils and base oil blend has cranking viscosity less than 3000 cP at ⁇ 35° C. as measured by ASTM-D5293-14 and Noack volatility less than 13% as measured by ASTM-D5800-10.
  • Embodiment 62 The engine oil according to any preceding enumerated Embodiment wherein the engine oil comprises 5 to 50 wt % of a biobased hydrocarbon base oil and 1 to 50 wt % of one or more co-base oils, wherein the co-base oil(s) are selected from non biobased Group IV base oils and base oil blend has cranking viscosity less than 3000 cP at ⁇ 35° C. as measured by ASTM-D5293-14 and kinematic viscosity greater than 4cSt at 100° C. as measured by ASTM-D445-14E2, and the engine oil has low temperature pumping viscosity less than 11,000 cP at ⁇ 40° C. as measured by ASTM-D4684-14.
  • Embodiment 63 The engine oil according to any preceding enumerated Embodiment wherein the engine oil comprises 5 to 50 wt % of a biobased hydrocarbon base oil and 1 to 50 wt % of one or more co-base oils, wherein the co-base oil(s) are selected from biobased Group IV base oils and base oil blend has cranking viscosity less than 3000 cP at ⁇ 35° C. as measured by ASTM-D5293-14, and kinematic viscosity greater than 4cSt at 100° C. as measured by ASTM-D445-14E2, wherein the engine oil has low temperature pumping viscosity less than 11,000 cP at -40° C. as measured by ASTM-D4684-14 and has renewable carbon content greater than 50% as measured by ASTM-D6866-12.
  • the co-base oil(s) are selected from biobased Group IV base oils and base oil blend has cranking viscosity less than 3000 cP at ⁇ 35° C. as measured by
  • Embodiment 64 The engine oil according to any preceding enumerated Embodiment wherein the engine oil comprises 5 to 50 wt % of a biobased hydrocarbon base oil and 1 to 50 wt % of one or more co-base oils, wherein the co-base oil(s) are selected from biobased Group V base oils and base oil blend has cranking viscosity less than 3000 cP at ⁇ 35° C. as measured by ASTM-D5293-14, and kinematic viscosity greater than 4cSt at 100° C. as measured by ASTM-D445-14E2, wherein the engine oil has low temperature pumping viscosity less than 60,000 cP at ⁇ 40° C. as measured by ASTM-D4684-14 and has renewable carbon content greater than 50% as measured by ASTM-D6866-12.
  • the co-base oil(s) are selected from biobased Group V base oils and base oil blend has cranking viscosity less than 3000 cP at ⁇ 35° C. as measured by
  • Embodiment 65 The engine oil according to any preceding enumerated Embodiment wherein the engine oil comprises 5 to 50 wt % of a biobased hydrocarbon base oil and 1 to 50 wt % of one or more co-base oils, wherein the co-base oil(s) are selected from estolide base oils and base oil blend has cranking viscosity less than 3000 cP at -35° C. as measured by ASTM-D5293-14, and kinematic viscosity greater than 4cSt at 100° C. as measured by ASTM-D445-14E2, wherein the engine oil has less than 11,000 cP at ⁇ 40° C. as measured by ASTM-D4684-14 and has renewable carbon content greater than 50% as measured by ASTM-D6866-12.
  • the co-base oil(s) are selected from estolide base oils and base oil blend has cranking viscosity less than 3000 cP at -35° C. as measured by ASTM-D5293-14, and
  • Embodiment 66 The engine oil according to Embodiment 63, 64 or 65 wherein the engine oil has a renewable carbon content greater than 60% as measured by ASTM-D6866-12.
  • Embodiment 67 The engine oil according to Embodiment 63, 64 or 65 wherein the engine oil has renewable carbon content greater than 70% as measured by ASTM-D6866-12.
  • Embodiment 68 The engine oil according to Embodiment 63, 64 or 65 wherein the engine oil has renewable carbon content greater than 80% as measured by ASTM-D6866-12.
  • Embodiment 69 The engine oil according to Embodiment 63, 64 or 65 wherein the engine oil has renewable carbon content greater than 90% as measured by ASTM-D6866-12.
  • Embodiment 70 The engine oil according to any preceding enumerated Embodiment wherein the engine oil comprises 5 to 50 wt % of a biobased hydrocarbon base oil and 1 to 50 wt % of one or more co-base oils, wherein the co-base oil(s) are selected from biobased esters and base oil blend has greater than 60% of biodegradability at 28 days as measured by OECD-301B, wherein the engine oil has renewable carbon content greater than 50% as measured by ASTM-D6866-12.
  • Embodiment 71 The engine oil of any preceding enumerated Embodiment, wherein the average molecular weight of the base oil is between about 300 and about 1500 g/mol.
  • Embodiment 72 The engine oil of any preceding enumerated Embodiment, wherein the base oil has a saturate content of at least 90% as determined by ASTM-D2007-11.
  • Embodiment 73 The engine oil of any preceding enumerated
  • Embodiment wherein the engine oil has, when determined by ASTM-D7320-13,
  • Embodiment 74 The engine oil of any preceding enumerated
  • Embodiment 75 The engine oil of any preceding enumerated Embodiment, wherein the engine oil has, when determined by ASTM-D6593-14,
  • Embodiment 76 The engine oil of any preceding enumerated Embodiment, wherein the engine oil has, when determined by ASTM-D7589-14, a total fuel economy index of at least 1.5% and a fuel economy index after 100 hrs aging of at least 0.6%.
  • Embodiment 77 The engine oil of Embodiment 76, wherein the engine oil has, when determined by ASTM-D7589-14,
  • Embodiment 78 The engine oil of Embodiment 76, wherein the engine oil has, when determined by ASTM-D7589-14,
  • Embodiment 79 The engine oil of any preceding enumerated Embodiment, wherein the engine oil has a bearing weight loss value of no more than 26 mg of when measured by ASTM-D6709-14.
  • Embodiment 80 The engine oil of any preceding enumerated Embodiment, wherein the base oil has an aniline point greater than 115° C.
  • Embodiment 81 An engine oil comprising a biobased base oil with renewable carbon content greater than 25% as measured by ASTM-D6866-12, and having a pour point of less than ⁇ 40° C. by ASTM-D97-12 in the absence of a pour point depressant.
  • Embodiment 82 The engine oil of any preceding enumerated Embodiment, wherein the engine oil meets the requirements of ILSAC GF-5.
  • Embodiment 83 The engine oil of any preceding enumerated Embodiment, wherein the engine oil meets the requirements of ILSAC GF-6
  • Embodiment 84 The engine oil of any preceding enumerated Embodiment, wherein the engine oil meets the requirements of API SN.
  • Embodiment 85 The engine oil of any preceding enumerated Embodiment, wherein the engine oil meets the requirements of dexos.
  • Embodiment 86 The engine oil of any preceding enumerated Embodiment, wherein the engine oil meets the requirements of ACEA-A1, ACEA-A2, ACEA-A3, ACEA-B1, ACEA-B2, ACEA-B3, and ACEA-B4.
  • Embodiment 87 The engine oil of any preceding enumerated Embodiment, wherein the engine oil meets the requirements of ACEA-E1, ACEA-E2, ACEA-E3, and ACEA-E4.
  • Embodiment 88 The engine oil of any preceding enumerated Embodiment, wherein the engine oil meets the requirements of PC-11.
  • Embodiment 89 The engine oil of any of Embodiments 81 to 88 wherein the engine oil does not contain a pour point depressant or a viscosity modifier and has less than 13% Noack volatility as measured by ASTM-D5800-10 method B.
  • Embodiment 90 An engine oil comprising a base oil, wherein
  • Embodiment91 The engine oil of Embodiment 90 wherein at least 50% of hydrocarbon molecules comprised by the base oil comprise an odd number of carbon atoms per molecule.
  • Embodiment92 The engine oil of Embodiment 90 wherein at least 60% of hydrocarbon molecules comprised by the base oil comprise an odd number of carbon atoms per molecule.
  • Embodiment93 The engine oil of Embodiment 90 wherein at least 70% of hydrocarbon molecules comprised by the base oil comprise an odd number of carbon atoms per molecule.
  • Embodiment94 The engine oil of Embodiment 90 wherein at least 80% of hydrocarbon molecules comprised by the base oil comprise an odd number of carbon atoms per molecule.
  • Embodiment95 The engine oil of any of Embodiments 90-94 wherein at least 50% of the base oil is biobased hydrocarbon base oil.
  • Embodiment96 The engine oil of any of Embodiments 90-94 wherein at least 60% of the base oil is biobased hydrocarbon base oil.
  • Embodiment97 The engine oil of any of Embodiments 90-94 wherein at least 70% of the base oil is biobased hydrocarbon base oil.
  • Embodiment98 The engine oil of any of Embodiments 90-94 wherein at least 80% of the base oil is biobased hydrocarbon base oil.
  • Embodiment99 The engine oil of any of Embodiments 90-94 wherein at least 90% of the base oil is biobased hydrocarbon base oil.
  • Embodiment100 The engine oil of any of Embodiments 90-94 wherein at least 95% of the base oil is biobased hydrocarbon base oil.
  • Embodiment101 The engine oil of any preceding enumerated Embodiment, wherein the engine oil is biodegradable.
  • Embodiment102 The engine oil of any of the preceding enumerated Embodiments wherein the biobased base oil has greater than 60% of biodegradation in 28 days according to OECD 301B test method.
  • Embodiment103 The engine oil of any of the preceding enumerated Embodiments wherein the biobased base oil has greater than 70% of biodegradation in 28 days according to OECD 301B test method.
  • Embodiment104 The engine oil of any preceding enumerated Embodiment, wherein the base oil comprises a biobased terpene selected from the group consisting of myrcene, ocimene, farnesene, and combinations thereof.
  • the base oil comprises a biobased terpene selected from the group consisting of myrcene, ocimene, farnesene, and combinations thereof.
  • Embodiment105 The engine oil of any preceding enumerated Embodiment, wherein the base oil comprises farnesene.
  • Embodiment106 The engine oil of Embodiment 105 wherein the engine oil does not contain a pour point depressant or a viscosity modifier, and has less than 13% Noack volatility as measured by ASTM-D5800-10 method B.
  • Embodiment107 The engine oil of any of preceding enumerated Embodiment, wherein the engine oil comprises about 50 wt % to about 99 wt % biobased hydrocarbon base oil and from about 0.2 to about 20 wt % of an additive package.
  • Embodiment108 The engine oil of Embodiment 107 wherein the additive package comprises at least one additive selected from the group consisting of anti-foaming agents, anti-wear agents, anti-oxidants, demulsifiers, detergents, dispersants, extreme pressure agents, friction modifiers, metal deactivators, pour point depressants, rust and corrosion inhibitors, viscosity modifiers, and combinations thereof.
  • the additive package comprises at least one additive selected from the group consisting of anti-foaming agents, anti-wear agents, anti-oxidants, demulsifiers, detergents, dispersants, extreme pressure agents, friction modifiers, metal deactivators, pour point depressants, rust and corrosion inhibitors, viscosity modifiers, and combinations thereof.
  • Embodiment109 The engine oil of Embodiment 108 wherein the additive package comprises an anti-wear additive selected from the group consisting of ashless, zinc-free, and zinc-containing, anti-wear additives, and combinations thereof.
  • an anti-wear additive selected from the group consisting of ashless, zinc-free, and zinc-containing, anti-wear additives, and combinations thereof.
  • Embodiment110 The engine oil of any preceding enumerated Embodiment, wherein the engine oil contains between about 0.1 wt % and about 1 wt % of a phenolic anti-oxidant.
  • Embodiment111 The engine oil of any preceding enumerated Embodiment, wherein the engine oil contains up to about 5 wt % of an anti-wear additive.
  • Embodiment112 The engine oil of any preceding enumerated Embodiment wherein the anti-wear additive contains an amine phosphate anti-wear additive and the engine oil further comprises up to about 1 wt % of the anti-wear additive(s).
  • Embodiment113 The engine oil of any preceding enumerated Embodiment, wherein the engine oil contains a viscosity index improver.
  • Embodiment114 The engine oil of any preceding enumerated
  • Embodiment wherein the engine oil contains at least 1 wt % of the viscosity index improver wherein viscosity index improver is selected from polyisobutylene, high molecular weight poly alpha olefin, olefin copolymer, functionalized olefin copolymer, polymethacrylate, polyalkylmethacrylate, copolymers of styrene/isoprene, copolymers of styrene/butadiene, copolymers of isorprene/butadiene, copolymers of isoprene/divinylbenzene, polyisoprene, and polybutadiene with stereoscopic structure of such polymer molecules are selected from star-shaped structure, asterisk shaped structure, linear chain structure, and branched chain structure.
  • viscosity index improver is selected from polyisobutylene, high molecular weight poly alpha olefin, olef
  • Embodiment 115 The engine oil of any preceding enumerated Embodiment wherein the biobased base oil is derived from farnesene.
  • Embodiment 116 The engine oil of any preceding enumerated Embodiment wherein the biobased base oil is derived from sugar.
  • Embodiment 117 In an apparatus comprising an internal combustion engine lubricated by an engine oil, the improvement comprising an engine oil according to any of the preceding enumerated Embodiments.
  • Embodiment 118 A process for formulating an engine oil, the process comprising combining a biobased base oil with an additive mixture and a viscosity modifier to form a first combination that meets or exceeds the performance requirements of one or more of the following engine oil certification programs: ILSAC GF-5, ILSAC GF-6, API SN, dexos, CJ-4, ACEA-A1, ACEA-A2, ACEA-A3, ACEA-B1, ACEA-B2, ACEA-B3, ACEA-B4, ACEA-E1, ACEA-E2, ACEA-E3, ACEA-E4, and PC-11, wherein
  • the additive mixture comprises two or more of additives selected from the group consisting of anti-foaming agents, anti-wear agents, anti-oxidants, demulsifiers, detergents, dispersants, extreme pressure agents, friction modifiers, metal deactivators, pour point depressants, rust and corrosion inhibitors, viscosity modifiers, and combinations thereof, and
  • the additive mixture without variation of the combination of additives or the relative proportions thereof within the additive mixture may alternatively be combined with a non-biobased Group I, a Group II, a Group III or a Group IV base oil, or a combination thereof and a viscosity modifier to form a second combination that meets or exceeds the performance requirements of one or more of the following engine oil certification programs: ILSAC GF-5, ILSAC GF-6, API SN, dexos, CJ-4, ACEA-A1, ACEA-A2, ACEA-A3, ACEA-B1, ACEA-B2, ACEA-B3, ACEA-B4, ACEA-E1, ACEA-E2, ACEA-E3, ACEA-E4, and PC-11

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