Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
  • C10M169/04—Mixtures of base-materials and additives
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/02—Well-defined aliphatic compounds
  • C10M2203/0206—Well-defined aliphatic compounds 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
  • C10M2203/02—Well-defined aliphatic compounds
  • C10M2203/024—Well-defined aliphatic compounds unsaturated
• • 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
  • C10M2203/06—Well-defined aromatic compounds
  • C10M2203/065—Well-defined aromatic compounds 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
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
  • C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
  • C10M2203/106—Naphthenic fractions
  • C10M2203/1065—Naphthenic 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
  • C10M2205/22—Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts
  • C10M2205/223—Alkylation reaction products with aromatic type compounds, e.g. Friedel-crafts used as base material
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/02—Hydroxy compounds
  • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
  • C10M2207/0406—Ethers; Acetals; Ortho-esters; Ortho-carbonates used as base material
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/28—Esters
  • C10M2207/2805—Esters 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
  • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
  • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/1003—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds used as base material
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
  • C10N2020/01—Physico-chemical properties
  • C10N2020/02—Viscosity; Viscosity index
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • 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
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/02—Pour-point; Viscosity index
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/04—Detergent property or dispersant property
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
  • C10N2030/06—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
  • C10N2030/18—Anti-foaming 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
  • C10N2030/24—Emulsion properties
• • 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
  • C10N2030/30—Anti-misting
• • 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
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

• the present disclosure generally relates to hydraulic fluids.
• the disclosure relates to biobased hydraulic fluids comprising a biobased hydrocarbon such as isoparaffinic hydrocarbon derived from hydrocarbon terpenes such as myrcene, ocimene and farnesene.
• a biobased hydrocarbon such as isoparaffinic hydrocarbon derived from hydrocarbon terpenes such as myrcene, ocimene and farnesene.
• Mineral oils from petroleum, natural oils from plants and animals, and synthetic esters such as polyol esters and poly-alpha-olefins (PAOs) are commonly used as base oils for hydraulic fluids and similar lubricants.
• Hydraulic fluids typically consist of 60-100% base oil by weight with the remainder in additives to provide various fluid properties, such as improved low temperature behavior, oxidative stability, demulsibility, and other properties, such as corrosion protection and wear protection. While the commercially available fluids traditionally used have advantages and attractive properties, they also have some disadvantages. For example, and
• a commercially available hydraulic fluid may have poor low temperature fluidity, poor fire resistance, poor thermal oxidative stability, and/or poor biodegradability.
• hydraulic fluids The primary purpose of hydraulic fluids is to maintain lubrication and fluid characteristics while in use within a system so as to maintain appropriate pressure to operate hydraulic actuators (cylinders/motors) or assemblies in machinery on demand.
• hydraulic actuators cylinders/motors
• the fluid In order for appropriate pressures to be maintained within a hydraulic system, the fluid is constantly being run through a pump. The constant pumping action creates a substantial buildup of heat in use, which hydraulic fluid must withstand.
• the operation of the hydraulic actuators and the process of constantly pumping the hydraulic fluid subjects the fluid to constant mechanical stresses. Mechanical sheer forces operate to degrade hydraulic fluids.
• Hydraulic oils are unique lubricants due to their widespread use in all forms of equipment operating in a wide range of environments.
• the pressure in a hydraulic system creates a situation where leaks are common.
• many pieces of hydraulic equipment are operated in environments with environmental sensitivity such as in and around water, mining, agriculture, and food, a more environmentally friendly hydraulic oil is highly desirable to industry.
• the desire for these properties is shown by the growth of the biobased hydraulic oil segment and increasing legislation around the world mandating the use of these products.
• Unfortunately the development of this market has been slow due to the performance limitations of the biobased hydraulic fluids that can meet the renewability and/or biodegradability requirements of the products.
• Biobased hydraulic fluids 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 a hydraulic fluid 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 hydraulic oils.
• Biodegradability can be determined using one or more standardized test procedures and can provide valuable insight in comparing the potential risk of different lubricant products to the environment.
• One such guideline and test method has been set by the Organization for Economic Cooperation and Development (OECD) for degradation and accumulation testing.
• the OECD has indicated that several tests may be used to determine the "ready biodegradability" of organic chemicals.
• aerobic ready biodegradability by the OECD 301 B method tests material over a 28-day period and determines biodegradation of the material by measuring the evolution of carbon dioxide from the microbial oxidation of the material's organic carbon.
• the carbon dioxide produced is trapped in barium hydroxide solution and is quantified by titration of residual hydroxide with standardized hydrogen chloride. To determine the percent
• the amount of carbon dioxide produced microbially from the test material is compared to its theoretical carbon dioxide content (the complete oxidation of the carbon in the test material to CO 2 ).
• Positive controls using sodium benzoate as a reference material, are run to check the viability of the aerobic microorganisms used in the procedure. Blank controls are also run in parallel. Tests, controls, and blanks are run in duplicate.
• isoparaffinic oil based hydraulic fluid has lower biodegradation than other commercially used and environmentally preferred biodegradable hydraulic fluids such as natural and synthetic ester based hydraulic fluids.
• Isoparaffinic oil has great difficulty meeting the industry standard for biodegradability of >60% in the OECD301 B test in 28 day. Also, the production of isoparaffinic oil still depends on depleting natural resources and thus has an adverse impact on carbon neutrality (carbon footprint balance).
• biodegradable hydraulic fluid the provision of a hydraulic fluid comprising a biobased hydrocarbon
• a hydraulic fluid comprising a biobased hydrocarbon
• clean biodegradable alternative hydrocarbon products which have improved environmental performance and/or physical properties such as better oxidative stability, low volatility, improved separation of oil from water (and air), and anti-wear properties.
• one aspect of the present disclosure is a hydraulic fluid comprising a hydrocarbon biobased base oil having an average molecular weight (weight average) between 300 g/mol and 900 g/mol, and an additive package, the additive package comprising an anti-oxidant.
• Another aspect of the present disclosure is a hydraulic fluid comprising a biobased hydrocarbon base oil, the hydraulic fluid having a biodegradable rate in excess of 60% as determined in accordance with OECD 301 B.
• Another aspect of the present disclosure is a hydraulic fluid comprising a biobased base oil, wherein at least about 20% of the carbon atoms in the biobased base oil originate from a renewable carbon source and the hydraulic fluid meets Denison Hydraulics standard HF-0.
• Another aspect of the present disclosure is a hydraulic fluid comprising a biobased base oil wherein at least about 20% of the carbon atoms in the biobased base oil originate from a renewable carbon source and the hydraulic fluid has a TAN ⁇ 2 at 1000 hours as determined in accordance with ASTM D943-04a (2010)e1 .
• Another aspect of the present disclosure is a hydraulic fluid comprising a biobased hydrocarbon base oil, wherein at least about 20% of the carbon atoms in the biobased base oil originate from a renewable carbon source and the hydraulic fluid has a pour point of less than 40 °C.
• Another aspect of the present disclosure is a hydraulic fluid comprising a biobased hydrocarbon base oil, the hydraulic fluid having a biodegradable rate in excess of 60% as determined in accordance with OECD 301 B.
• Another aspect of the present disclosure is a hydraulic fluid comprising a biobased base oil having the molecular structure:
• [B] is biobased hydrocarbon repeating unit
• [P] is non-biobased hydrocarbon repeating unit
• n is greater than 1 , and m is less than 4;
• the stereoscopic arrangement of [B] and [P] repeating unit can be linear, branched, and cyclic.
• the molecular weight is in range of 300 g/mol to 900 g/mol; and the biobased content of the hydraulic fluid is greater than 20%, as measured by ASTM D6866-12.
• Another aspect of the present disclosure is a biobased hydraulic fluid that can be mixed with a Group I, Group II, or Group III hydraulic fluid and used for top off in the field.
• Another aspect of the present disclosure is a formulated hydraulic fluid, said hydraulic fluid having an ISO viscosity grade of 2 to 46,000 and comprising:
• basestocks having a viscosity range of from 3 cSt to 50 cSt, Group II and Group III hydroprocessed basestocks, and a Group IV PAO having a VI of about 130 or less; or
• Another aspect of the present disclosure is a hydraulic fluid
• a base oil having a weight average molecular weight in the range of 400 to 600 g/mol, a viscosity index greater than 120 and less than 140; and (b) an anti-wear hydraulic oil additive package; wherein the hydraulic fluid has (i) an air release by ASTM D 3427-012 of less than 0.8 minutes at 50 °C, and (ii) a Sequence II foam tendency by ASTM D 892-13 of less than 50 ml, and a biodegradability rate of at least 60% as determined by OECD 301 B.
• Another aspect of the present disclosure is a hydraulic fluid comprising a biobased hydrocarbon base oil, the hydraulic fluid being compatible with and suitable for mixing with a Group I, Group II, or Group III hydraulic fluid.
• Another aspect of the present disclosure is an apparatus comprising a pump lubricated by a hydraulic fluid as described in any of the preceding paragraphs.
• Another aspect of the present disclosure is a gear system, circulation lubrication system, hydraulic system, compressor system, vacuum pump, metal working machinery, electrical switch or connector comprising a hydraulic fluid, the improvement comprising a hydraulic fluid according to any preceding paragraph.
• Fig. 1 is a plot comparing biodegradability of different types of base oils using the OECD 301 B method.
• Fig. 2 is a plot showing the percentage biodegradation of hydraulic oil formulated with biobased base oils according to one embodiment of the present disclosure, Exp-Hyd.BL.1 , over a period of 28 days.
• 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, February 13, 2012 and published as WO 2012/141784 on October 18, 2012, by Nicholas Ohler, et al., and assigned to Amyris, Inc. in Emeryville, California. These base oils have been stated to have utility as lubricant base stocks.
• WO 2012/141784 discloses that terpenes are capable of being derived from isopentyl pyrophosphate or dimethylallyl pyrophosphate and the term "terpene” encompasses hemiterpenes, monoterpenes, sesquiterpenes, diterpenees,
• 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 conjuggated hydrocarbon terpene refers to a terpene
• 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
• hydrocarbon terpenes include isoprene, myrcene, a-ocimene, ⁇ -ocimene, a-farnesene, ⁇ -farnesene, ⁇ -springene, geranylfarnesene, neophytadiene, c/s-phyta-1 ,3-diene, trans- phyta-1 ,3-diene, isodehydrosqualene, isosqualane precursor I, and isosqualane precursor II.
• 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.
• 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 hydraulic fluid.
• biobased base oil specifications that can be used to produce blends suitable for hydraulic fluid formulation for one embodiment are set forth in Table III.
• a commercially available biobased hydrocarbon base oil (a partially hydrogenated ⁇ - 3,7,1 1 -trimethyldodeca-1 ,3,6,10-tetraene reaction products with linear C8-C16 alpha- olefin, hydrogenated) sold under the commercial designation NOVASPEC (Novvi LLC, Emeryville, CA, United States; (REACH registration number 01 -2120031429-59-0000)., is used.
• wt % up to about 100 wt % of the biobased hydrocarbon base oil may be used.
• wt% additives namely one or more antioxidants, anti-wear/extreme pressure additives, rust and corrosion inhibitors, metal deactivators, thickeners, viscosity index (VI) improvers, pour point depressants, co-solvents, friction modifiers, foam inhibitors, and/or demulsifiers for a hydraulic fluid formulation.
• a blend component comprising one or more oils or liquids may also be used as the base oil to formulate or complete the hydraulic fluid, or to adjust the viscosity of the fluid or some other desired characteristic.
• Such additive oils or liquids may be selected from one or more of the following: microbial oils, vegetable oils, seed oils, mineral oils, isoparaffinic
• hydrocarbon fluids silicone fluids, synthetic esters, poly alpha-olefins, polysiloxanes, pentaerythritol esters, poly(butane) liquids, and combinations thereof.
• the particular additives and the quantity of each used are selected with desired performances and intended use in mind.
• Other biobased oils may be used as a base oil in a similar manner, with attention to viscosity as with the biobased hydrocarbon base oil.
• biobased base oil is understood to mean any biologically derived oil to be used as a base oil in a hydraulic fluid.
• 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.
• a measurement of >100% C indicates the source of carbon has an age of more than several years. See, e.g., WO 2012/141784, incorporated herein by reference.
• At least about 20% of the carbon atoms in the base oil comprised by a hydraulic fluid originate from renewable carbon sources.
• at least about 30% of the carbon atoms in the base oil comprised by a hydraulic fluid originate from renewable carbon sources.
• at least about 40% of the carbon atoms in the base oil comprised by a hydraulic fluid originate from renewable carbon sources.
• at least about 50% of the carbon atoms in the base oil comprised by a hydraulic fluid originate from renewable carbon sources.
• at least about 60% of the carbon atoms in the base oil comprised by a hydraulic fluid originate from renewable carbon sources.
• At least about 70% of the carbon atoms in the base oil comprised by a hydraulic fluid originate from renewable carbon sources.
• at least about 80% of the carbon atoms in the base oil comprised by a hydraulic fluid originate from renewable carbon sources.
• at least about 90% of the carbon atoms in the base oil comprised by a hydraulic fluid originate from renewable carbon sources.
• the carbon atoms of the base oil component of the hydraulic fluid 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 a biobased hydrocarbon base oil is a 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
• 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.
• a mono-olefinic alpha-olefin having structure A1 1 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,
• an alpha-olefin having the general structure A1 1 includes 3,7,1 1 - trimethyldodecene having structure A12.
• a mono-olefinic alpha-olefin having structure A1 1 may be prepared from the appropriate conjugated hydrocarbon terpene using any suitable method.
• the mono-olefinic alpha-olefin having structure A1 1 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
• the primary alcohol of the corresponding hydrocarbon terpene may be obtained using any suitable method.
• 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 A1 1 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 )(R3), where Ri and R2 are alkyl groups such as methyl or ethyl, and R3 is an unsaturated hydrocarbon originating from the conjugated terpene.
• ⁇ -farnesene R3 is
• the resulting amine may be oxidized to the N-oxide using hydrogen peroxide 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 A1 1 .
• Scheme I illustrates an example of such a preparation of an alpha-olefin having structure A1 1 usin ⁇ -farnesene as a model compound.
• the amine N(R )(R 2 )(R3) can be hydrogenated (e.g., using an appropriate catalyst), treated with peroxide, and heated to undergo elimination to form an alpha-olefin having structure A1 1 (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 A1 1 .
• Any suitable dehydration apparatus can be used, but in some variations, a hot tube reactor (e.g., at 250°C) is used to carry out a dehydration of a primary alcohol.
• 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 A1 1 may in certain instances be derived from a conjugated hydrocarbon terpene having a 1 ,3- diene moiety, such as myrcene, farnesene, springene, geranylfarnesene,
• 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 A1 1 , 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. Frolov et al, "Highly active supported palladium catalysts for selective hydrogenation of conjugated dienes into olefins," Reaction Kinetics and
• ⁇ - 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 l-trimethyldodec-2-ene, 3,7,1 1 - trimethyldodec-1 -ene, or 3-methylene-7,1 1 -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(lll), 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 )2TiCI 2 (Cp 2 TiCI 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 1 N 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., 3,7,1 1 -thmethyldodeca-1 ,6,10-triene if farnesol is used as the starting material).
• reaction may be quenched with t-BuOMe, washed with 1 N HCI, brine, dried, and concentrated under reduced pressure.
• 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., 3,7,1 1 -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 A1 1 , 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.
• alpha-olefinic species having structure A1 1 , A12 or A15 mono-olefinic species having structure A13, or unsaturated terminal olefin species having structure A14
• 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-7,1 1 -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% 3,7,1 1 -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% 3,7,1 1 - 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.
• 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.
• the performance advantages of synthetic hydraulic fluids made with biobased base oils of this disclosure changes the overall concept of hydraulic fluid performance. With the present disclosure, high performance can be obtained while still providing environmental compatibility.
• the hydraulic fluids of this disclosure provide a number of advantages. In some embodiments, they are more biodegradable and have significantly more renewable content than poly-alpha-olefin (PAO) or mineral oil hydraulic fluids. In some embodiments, they have lower toxicity than Group I base oil hydraulic fluids. In some embodiments, they also demonstrate better hydrolytic stability and oxidation resistance than ester or vegetable oil hydraulic fluids. In some embodiments, the hydraulic fluids of this disclosure also have better demulsibility than esters/vegetable oil hydraulic fluids and also than some mineral oil based hydraulic fluids. Additionally, in some
• hydraulic fluids of this disclosure provide better seal compatibility than vegetable or ester derived hydraulic fluids.
• Table IV provides a comparison of one exemplary embodiment of a hydraulic fluid of this disclosure with various lubricants used commercially as hydraulic fluids. Table IV demonstrates that this exemplary embodiment of a renewable hydrocarbon hydraulic fluid (called the “experimental fluid”) provides "best in class" performance. This exemplary embodiment of a renewable hydrocarbon hydraulic fluid meets the most stringent environmental characteristics of renewability and
• the PAO and mineral oil reported in Table IV both provided the classical performance as expected around wet TOST and oxidative stability but did not meet the environmental specifications.
• the exemplary fluid of this disclosure also shows significantly improved oxidation stability than any of the commercial products.
• a hydraulic fluid has a number of desirable characteristics. Among these is appropriate viscosity. Viscosity is a measure of a fluid's resistance to flow and is often a hydraulic fluid's most important characteristic. Viscosity significantly impacts operation of the system which a hydraulic fluid is to lubricate. When a hydraulic fluid has a viscosity that is too low, it does not seal sufficiently, leading to leakage and wear of parts, and the fluid also will not pump efficiently. When a hydraulic fluid has a viscosity that is too high, it can be difficult to pump through the system and may consequently reduce operating efficiency. Hydraulic fluids also preferably retain optimum viscosity during operation in cold or hot temperatures, in order to consistently and effectively transmit power.
• Seal performance is critical to a hydraulic system to contain leaks and maintain performance.
• Base oil chemistry is a key driver for seal performance and the biobased base oils of this disclosure demonstrate equivalent or better performance than the conventional hydrocarbon alternatives.
• Table VI shows a comparison of the biobased base oil of this disclosure in comparison to a PAO with a mix of various ester chemistries. The PAO and the biobased base oil show equivalent seal performance. This is an advantage over typical biobased base oils that have high polarity and can offer induce significant seal swelling.
• the hydraulic fluid compositions of the present disclosure comprise a biobased base oil and one or more additives constituting an "additive package" for the hydraulic fluid formulation.
• the additive package may comprise one or more of the following additives (or a combination of additives from one class, e.g., a combination of anti-oxidants) in the following ranges (as a weight percentage of the hydraulic fluid formulation).
• Oxidation stability is a hydraulic fluid's resistance to heat-induced degradation caused by a chemical reaction with oxygen. Hydraulic fluids should preferably resist oxidation. Additives often help the fluid with this goal, improving the stability and extending the life of the fluid.
• the hydraulic fluid formulation comprises an antioxidant.
• the hydraulic fluid formulation will comprise about 0.01 -5% anti-oxidant.
• the hydraulic fluid may comprise about 0.05-2% anti-oxidant.
• the hydraulic fluid may comprise about 0.1 - 1 % anti-oxidant.
• the anti-oxidant may be a single antioxidant or it may comprise a combination of anti-oxidants. Further, in each of these embodiments, the anti-oxidant(s) may be selected from among phenolic, aminic, sulfur/phosphorous anti-oxidants or combinations thereof.
• antioxidants include without limitation butylated hydroxyanisole, di-butyl-paracresol (BHT), alkylated diphenylamines, 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, and mixtures of these.
• BHT di-butyl-paracresol
• vitamin-E tocopherol
• ⁇ -carotene sterically hindered alkylthiomethylphenol
• 2-(1 ,1 -Dimethylethyl)-1 ,4-benzenediol l,2-dihydro-2,2,4- trimethylquinoline
• ascorbyl palmitate propyl gallate
• Hydraulic fluid for an application in the environmentally sensitive areas requires environmental performance of toxicity and biodegradability in addition to improved oxidation stability requirement.
• Some of the above listed chemistries can meet both requirements along with thiodiethylene bis (3,5-di-tert-butyl-4-hydroxyhydrocinnamate).
• This chemistry is a sterically hindered phenolic antioxidant.
• This chemistry is excellent for inhibiting oxidation and increasing thermal stability for hydrocarbon base oils.
• the preferred chemistry has low toxicity to aquatic fish and plants making it ideal for environmental applications.
• phenolic anti-oxidants are available.
• the chemistry preferably contains no (or at least no detectible) or minimal levels of sulfur or
• phosphorus to meet toxicity specifications for the formulation. This can allow the treat rate to be larger, up to 5%, preferably ⁇ 2%, more preferable, ⁇ 1 %.
• These types of antioxidants can be in liquid form and this is the preferred state for ease of manufacturing.
• octylated/butylated diphenylamine or alkylated phenyl-a-naphthylamine chemistry can be used. This aminic chemistry can be used alone or in combination with the phenolic anti-oxidants for synergistic effects. Depending on the type of amine chemistry the toxicity effects on the overall formulation may vary.
• the treat rate may be ⁇ 0.5% versus the naphthylamine which can treat at higher rates and up to 5%.
• Each of these chemistries contain nitrogen at levels ⁇ 5% but contain no Sulfur or Phosphorous compounds.
• 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
• 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-a-naphthylamine, and alkylated-a-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 hydraulic fluid described in the 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.
• exemplary phenolic anti-oxidants include: 2-t- butyl-4-heptyl phenol; 2-t-butyl-4-octyl phenol; 2-t-butyl-4-dodecyl phenol; 2,6-di-t-butyl- 4-heptyl phenol; 2,6-di-t-butyl-4-dodecyl phenol; 2-methyl-6-di-t-butyl-4-heptyl phenol; and 2-methyl-6-di-t-butyl-4-dodecyl phenol.
• ortho coupled phenols examples include: 2,2'-bis(6t-butyl-4-heptyl phenol); 2,2'-bis(6-t-butyl-4-octyl phenol); and 2,2'-bis(6-t-butyl- 4-dodecyl phenol).
• Sulfur containing phenolics may also be used to advantage in certain embodiments.. The sulfur can be present as either aromatic or aliphatic sulfur within the phenolic antioxidant molecule.
• exemplary aminic anti-oxidants include ⁇ , ⁇ '- dihexyldiphenylamine; p,p'-diheptyldiphenylamine; ⁇ , ⁇ '-dioctyldiphenylamine; p,p'- dinonyldiphenylamine; ⁇ , ⁇ '-didecyldiphenylamine; p,p'-didodecyldiphenylamine;
• octylphenyl- -naphthylamine t-octylphenyl-a-naphthylamine; phenyl-a-naphthylamine; phenyl- -naphthylamine; p-octyl phenyl-a-naphthylamine; 4-octylphenyl-l-octyl- - naphthylamine.
• exemplary sulfur/phosphorous anti-oxidants include n-dodecyl-2-hydroxyethyl sulphide; 1 -(tert-dodecylthio)-2-propanol; dibenzyl sulfide, polysulfides, diaryl sulfides, modified thiols, mercaptobenzimidazoles, thiophene derivatives, xanthogenates, and thioglycols, 2-(4-hydroxy-3,5-di-t-butyl benzyl thiol)acetate, alkylthiocarbamoyl with linear and branched alkyl groups of from 3-30 carbon atoms, alkyl and aryl mono, di, triphosphites with linear or branched alkyl or aryl group from 4-20 carbon atoms, thio and dithiophosphates with linear or branched alkyl or aryl groups from 4-20 carbons,
• the hydraulic fluid formulation comprises an anti- wear/extreme pressure additive.
• the hydraulic fluid formulation may comprise about 0.01 -10% anti-wear/extreme pressure additive.
• the hydraulic fluid may comprise about 0.01 -2% anti-wear/extreme pressure additive.
• the hydraulic fluid may comprise about 0.1 -1 % anti-wear/extreme pressure additive.
• the anti-wear/extreme pressure additive may be a single anti-wear/extreme pressure additive or it may comprise a combination of anti-wear/extreme pressure additives. Further, in each of these embodiments, the anti-wear/extreme pressure additive may be selected from among the following compositions:
• each alkyl group contains about 8 to about 12 carbon atoms.
• alkyl moieties include butyl, sec-butyl, isobutyl, tert-butyl, pentyl, n- hexyl, sec-hexyl, n-octyl, 2-ethylhexyl, decyl and dodecyl;
• a rust inhibitor is an additive that is mixed with a hydraulic fluid base oil to prevent rust in finished hydraulic fluid applications.
• Examples of commercial rust inhibitors are metal sulfonates, alkylamines, alkyl amine phosphates, alkenyl succinic acids, fatty acids, and acid phosphate esters.
• Rust inhibitors are sometimes comprised of one or more active ingredients. Examples of applications where rust inhibitors are needed include: internal combustion engines, turbines, electric and mechanical rotary machinery, hydraulic equipment, gears, and compressors. Rust inhibitors work by interacting with steel surfaces to form a surface film or neutralize acids. Rust inhibitors are effective in some embodiments of the hydraulic fluid when they are used in an amount less than 25 weight percent. In some other embodiments, rush inhibitors are effective in an amount less than 10 weight percent of the total composition. In some other embodiments, rust inhibitors are effective in an amount less than 1 weight percent, e.g., (less than 0.1 %).
• the hydraulic fluid formulation comprises a rust or a corrosion inhibitor additive.
• the hydraulic fluid formulation may comprise about 0.01 -5% rust and/or corrosion inhibitor additive.
• the hydraulic fluid may comprise about 0.01 -2% rust and/or corrosion inhibitor additive.
• the hydraulic fluid may comprise about 0.1 -0.5% rust and/or corrosion inhibitor additive.
• the rust and/or corrosion inhibitor additive may be a single rust and/or corrosion inhibitor additive or it may comprise a combination of rust and/or corrosion inhibitor additives.
• the rust and/or corrosion inhibitor additive may be selected from among the following compositions:
• succinimde derivatives such as the higher alkyl substituted amides of dodecylene succinic acid, higher alkyl substituted amides of dodecenyl succinic acid such as the tetrapropenylsuccinic monoesters (commercially available) and imidazoline succinic anhydride derivatives, e.g. the imidazoline derivatives of tetrapropenyl succinic anhydride;
• the hydraulic fluid formulation comprises a metal deactivator additive.
• the hydraulic fluid formulation may comprise about 0.01 -5% metal deactivator additive.
• the hydraulic fluid may comprise about 0.01 -2% metal deactivator additive.
• the hydraulic fluid may comprise about 0.1 -0.5% metal deactivator additive.
• the metal deactivator additive may be a single metal deactivator additive or it may comprise a combination of metal deactivator additives.
• the rust and/or corrosion inhibitor additive may be selected from among the following compositions: ⁇ , ⁇ -disubstituted aminomethyl-1 ,2,4-triazoles, and the ⁇ , ⁇ -disubstituted amino methyl-benzotriazoles; derivatives of benzotriazoles, benzimidazole, 2-alkyldithiobenzimidazoles, 2-alkyldithiobenzothiazoles, 2-(N,N- dialkyldithio-carbamoyl)benzothiazoles, 2,5-bis(alkyl-dithio)- 1 ,3,4-thiadiazoles, 2,5- bis(N,N-dialkyidithiocarbamoyl)-1 ,3,4-thiadiazoles, and 2-alkyldithio-5-mercapto thiadiazoles.
• the hydraulic fluid formulation comprises a thickener, viscosity index (“VI”) improver or pour point depressant additive.
• the hydraulic fluid formulation may comprise about 0.1 -25% thickener, viscosity index (“VI") improver or pour point depressant additive.
• the hydraulic fluid may comprise about 0.5-20% thickener, viscosity index (“VI") improver or pour point depressant additive.
• the hydraulic fluid may comprise about 1 -15% thickener, viscosity index (“VI") improver or pour point depressant additive.
• the thickener, viscosity index (“VI") improver or pour point depressant additive may be a single thickener, viscosity index (“VI") improver or pour point depressant additive or it may comprise a combination of thickener, viscosity index (“VI”) improver or pour point depressant additives. Further, in each of these embodiments, the thickener, viscosity index (“VI”) improver or pour point depressant additive may be a single thickener, viscosity index (“VI”) improver or pour point depressant additive or it may comprise a combination of thickener, viscosity index (“VI”) improver or pour point depressant additives. Further, in each of these embodiments, the thickener, viscosity index (“VI”) improver or pour point depressant additive may be a single thickener, viscosity index (“VI”) improver or pour point depressant additive or it may comprise a combination of thickener, viscosity index (“VI”) improver or pour point depressant additives
• the thickener, viscosity index (“VI”) improver or pour point depressant additive may be selected from among the following compositions:
• esters of maleic anhydride-styrene copolymers polymethacrylates; polyacrylates; polyacrylamides; condensation products of haloparaffin waxes and aromatic compounds; vinyl carboxylate polymers; and terpolymers of dialkylfumarates, vinyl esters of fatty acids, ethylene-vinyl acetate copolymers, alkyl phenol formaldehyde condensation resins, alkyl vinyl ethers and mixtures thereof.
• Esters can be considered a co-base oil or additive depending on the degree of environmental performance for the target of the formulation. Typically there can be a renewability requirement on the amount of renewable carbon contained in the overall formulation.
• the renewable base oil of the disclosure can vary in its amount of renewable carbon. To add additional renewable carbon fatty acids, esters, glycerine, or other biobased base oils can be considered.
• Trimethylolpropantrioleates Triglycerides, Trimethylolpropane esters, Polyl complex esters, 2-Ethylhexyl Cocoate, methyl esters, saturated trimethylolpropane ester, trimethylolpropane ester of carboxylic acids, saturated monopentaerythritol branched acids, trimethylolpropane, and complex esters of carboxylic acids.
• the hydraulic fluid formulation comprises an ester or cosolvent.
• the hydraulic fluid formulation may comprise about 0.1 -75% ester or cosolvent.
• the hydraulic fluid may comprise about 1 -70% ester or cosolvent.
• the hydraulic fluid may comprise about 3- 20% ester or cosolvent.
• the ester or cosolvent additive may be a single ester or cosolvent or it may comprise a combination of ester or cosolvent.
• the ester or cosolvent may be selected from among the following compositions (and included as a co-base oil or an additive):
• esters made by dehydration of mono-acids, di-acids, tri-acids with alcohols with mono-, di- or multi-alcohols Preferred acids include C4-C30 monobasic acids, more preferably 2-ethylhexanoic acid, isoheptyl, isopentyl, and capric acids, and di-basic acids, more preferably adipic, fumaric, sebacic, azelaic, maleic, phthalic, and terephthalic acids, dimerized and trimerized fatty acids.
• the alcohols can be any of the suitable mono-alcohols or polyols.
• Preferred examples are glycerol, 2-ethylhexanol, iso-tridecanols, neopentyl glycol, trimethylol ethane, 2-methyl-2-propyl- 1 ,3-propanediol, trimethylol propane, pentaerythritol, and dipentaerythritol, ethoxylated, propoxylated and butoxylated alcohols; and.
• the hydraulic fluid formulation comprises a friction modifier additive.
• the hydraulic fluid formulation may comprise about 0.01 -5% friction modifier additive.
• the hydraulic fluid may comprise about 0.05-5% friction modifier additive.
• the hydraulic fluid may comprise about 0.1 -2% friction modifier additive.
• the friction modifier additive may be a single friction modifier additive or it may comprise a combination of friction modifier additives. Further, in each of these embodiments, the friction modifier additive may be selected from among the following compositions:
• aliphatic amines or ethoxylated aliphatic amines aliphatic fatty acid amides, aliphatic carboxylic acids, aliphatic carboxylic esters, aliphatic carboxylic esteramides, aliphatic phosphonates, aliphatic phosphates, aliphatic thiophosphonates, aliphatic
• aliphatic substituted succinimides formed by reacting one or more aliphatic succinic acids or anhydrides with ammonia.
• Molybdenum salts such as carbamate,
• the hydraulic fluid formulation comprises a foam inhibitor additive.
• the hydraulic fluid formulation may comprise about 0.001 -1 % foam inhibitor additive.
• the hydraulic fluid may comprise about 0.005-0.5% foam inhibitor additive.
• the hydraulic fluid may comprise about 0.005-0.2% foam inhibitor additive.
• the friction modifier additive may be a single foam inhibitor additive or it may comprise a combination of foam inhibitor additives.
• the foam inhibitor additive may be selected from among the following compositions:
• the hydraulic fluid formulation comprises a demulsifier additive.
• the hydraulic fluid formulation may comprise about 0.001 -1 % demulsifier additive.
• the hydraulic fluid may comprise about 0.005-0.5% demulsifier additive.
• the hydraulic fluid may comprise about 0.005-0.2% demulsifier additive.
• the demulsifier additive may be a single foam inhibitor additive or it may comprise a combination of demulsifier additives. Further, in each of these
• the demulsifier additive may be selected from among the following compositions: derivatives of propylene oxide, ethylene oxide, polyoxyalkylene alcohols, alkyl amines, amino alcohols, diamines or polyamines reacted sequentially with ethylene oxide or substituted ethylene oxides or mixtures thereof.
• demulsifiers include trialkyl phosphates, polyethylene glycols, polyethylene oxides, polypropylene oxides, (ethylene oxide-propylene oxide) polymers and mixtures thereof.
• Table VII shows that effect of different additive packages containing different anti-oxidant chemistries when varied by treat rate will impart large differences in the disclosures finished hydraulic fluid oxidation performance when measured by the RPVOT.
• all of the disclosure formulas have the same base oil mixture of the biobased base oil of this disclosure in two different grades, 4cSt and 6cSt, along with an ester at 20%.
• Water can react with additives in hydraulic fluids forming oil insoluble material. These insoluble materials will usually precipitate and in doing so may block filters, valves and other components, resulting in decreased flow of the hydraulic fluid in the system. Blockage can eventually result in unplanned downtime. Hydraulic fluids are thus typically designed so they can be filtered without depletion of additives to the fluids.
• the hydraulic fluids of this disclosure typically show excellent filterability results due to the biobased base oil chemistry and achieve values of ⁇ 100 sec when running the Denison Filterability test, TP02100. When tested with and without water the formulations of this disclosure achieve the results shown below in Table VIII.
• water can enter the system as condensation or contamination, and mix with the hydraulic oil. Water can cause rusting of hydraulic components. In addition, water can react with some additives to form chemical species which can be aggressive to metals. Hydraulic fluid formulations typically contain rust and corrosion inhibitors which prevent the interaction of water or other chemical species from attacking metal surfaces.
• Non-limiting examples include calcium sulfonate, N-acyl sarcosine, copper deactivators, fatty acid alkanolamides based on saturated or unsaturated fatty acids typically having 10 to 20 carbon atoms, alcohols typically having 2 to 14 carbon atoms, and aromatic monocarboxylic acids and aliphatic dicarboxylic acids typically having 10 to 12 carbon atoms,
• Tables IX, X and XI show the drastic effect that esters have on hydrolytic stability of a hydraulic oil.
• the biobased base oil was formulated with a 6cSt grade along with a standard additive package, anti-foam agent, and viscosity index improver ("VII") this base formulation was then mixed with an ester at 25%.
• VI viscosity index improver
• Five esters were explored to look at their change in acid number effect when running the D2619 hydrolytic stability test..
• Four of the five ester chemistries resulted in acid numbers that were significantly higher than the passing specification, while the other was improved but still outside of the D2619-09 passing specification for Denison HF-0.
• Ester #1 which showed the best performance in the ASTM D2619-09 test (Table IX), was used in formulations A-F (Table X) and evaluated in accordance with ASTM D943-04a
• Foam In addition to resisting water, hydraulic fluids should also resist foaming. Foam is compressible and has poor lubricating properties and thus can hinder operation of the hydraulic fluid and the system it is in. Foam results from air or other gases becoming entrained in the hydraulic fluid. Air enters a hydraulic system through the reservoir or through air leaks within the system. A hydraulic fluid under high pressure can contain a large volume of dissolved or dispersed air bubbles. When this fluid is depressurized, the air bubbles expand and produce foam. Foam inhibitors typically modify the surface tension on air bubbles so they more easily break up.
• Foam tendency and stability are measured by ASTM D 892-12.
• ASTM D 892-12 measures the foaming characteristics of a hydraulic base oil at 24 °C and 93.5 °C. It provides a means of empirically rating the foaming tendency and stability of the foam.
• the lubricating base oil maintained at a temperature of 24 0 C, is blown with air at a constant rate for 5 minutes then allowed to settle for 10 minutes.
• the volume of foam, in ml is measured at the end of both periods (Sequence I).
• the foaming tendency is provided by the first measurement, the foam stability by the second measurement. The test is repeated using a new portion of the lubricating base oil at 93.5 0 C.
• Sequence II after the foam has collapsed and cooled to 24 °C.
• the lubricating base oil is blown with dry air for 5 minutes, and then settled for 10 minutes.
• the foam tendency and stability are again measured, and reported in ml.
• a good quality hydraulic oil will generally have less than 100 ml foam tendency for each of Sequence I, II, and III; and zero ml foam stability for each of Sequence I, II, III; the lower the foam tendency of a lubricating base oil or hydraulic oil the better.
• Table XII below provides formulations of three example hydraulic fluids tested. It can be seen that the selection of the proper defoamer is critical to meeting the foaming requirements for the hydraulic oil. In the sample formulations, the Defoamer B and C did not yield satisfactory results while Defoamer A meets the hydraulic oil specification and demonstrates the performance of the biobased base oil.
• the hydraulic fluid composition comprises specially formulated additive packages to provide required durability and performance.
• Various characteristics, properties and components which contribute to such characteristics and properties are discussed below.
• a rust inhibitor is an additive that is mixed with a hydraulic fluid base oil to prevent rust in finished hydraulic fluid applications.
• Examples of commercial rust inhibitors are metal sulfonates, alkylamines, alkyl amine phosphates, alkenyl succinic acids, fatty acids, and acid phosphate esters.
• Rust inhibitors are sometimes comprised of one or more active ingredients. Examples of applications where rust inhibitors are needed include: internal combustion engines, turbines, electric and mechanical rotary machinery, hydraulic equipment, gears, and compressors. Rust inhibitors work by interacting with steel surfaces to form a surface film or neutralize acids. Rust inhibitors are effective in some embodiments of the hydraulic fluid when they are used in an amount less than 25 weight percent. In some other embodiments, rush inhibitors are effective in an amount less than 10 weight percent of the total composition. In some other embodiments, rust inhibitors are effective in an amount less than 1 weight percent, e.g., (less than 0.1 %).
• Rust inhibition of lubricating oils or hydraulic oils is determined using ASTM D 665-12.
• ASTM D 665-12 is directed to a test for determining the ability of oil to aid in preventing the rusting of ferrous parts should water become mixed with the oil. In this test a mixture of 300 ml. of the test oil is stirred with 30 ml. of distilled or synthetic seawater at a temperature of 60° C with a cylindrical steel specimen completely immersed therein for 4 hours, although longer and shorter periods of time also may be utilized.
• Air release properties are generally associated with the base oil composition and kinematic viscosity. Air release properties are measured by ASTM D 3427-12.
• the air release test is done by saturating the fluid (normally at 50°C, but other temperatures such as 25° C are also possible) with air bubbles and then measuring the time it takes for the fluid to return to an air content of 0.2%. Air release times are generally longer for Group I base oils than for Group III base oils. Polyol ester, poly-alpha-olefin, and phosphate ester base oils typically have lower air release than conventional mineral oils. Typical air release specifications for hydraulic oils vary from 5 minutes maximum for ISO 32 oils, through 7 minutes maximum for ISO 46 oils, through 17 minutes maximum for ISO 150 oils. Air release values generally increase with viscosity of the base oil.
• Good air release is a critical property for hydraulic fluids. Agitation of hydraulic fluid with air in equipment, such as bearings, couplings, gears, pumps, and oil return lines, may produce a dispersion of finely divided air bubbles in the oil. If the residence time in the hydraulic system reservoir is too short to allow the air bubbles to rise to the oil surface, a mixture of air and oil will circulate through the hydraulic system. This may result in an inability to maintain oil pressure, incomplete oil films in bearings and gears, and poor hydraulic system performance or failure. The inability to maintain oil pressure is especially pronounced with hydraulic systems having centrifugal pumps. Oil having poor air release can cause sponginess and lack of sensitivity of the control of turbine and hydraulic systems.
• Air release is measured by ASTM D 3427-12. Compressed air is blown through the test oil, which has been heated to a temperature of 25 or 50 °C. After the air flow is stopped, the time required for the air entrained in the oil to reduce in volume to 0.2% is recorded under the conditions of the test and at the specified temperature. Air release is mainly a function of the base stock, and oils need to be monitored for this. Additives cannot positively influence air release time.
• the air releases of the hydraulic fluids of the present disclosure are very low, generally less than 2.1 minutes at 50°C as illustrated in Table XIII.
• the anti-wear/extreme pressure additive may be an additive package provided by an additive company or formulated by a lubricant formulator.
• a preferred additive package is an AW hydraulic oil additive package, more preferably one that meets the Denison HF-0 standard. It may be an ashless, zinc-free, or a zinc-based AW hydraulic oil additive package.
• Preferred AW hydraulic oil additive packages designed to meet the Denison HF-0 standard will also meet the AFNOR wet filterability test.
• the Denison HF-0 standard concerns hydraulic oils for use in axial piston pumps and vane pumps in severe duty applications.
• the hydraulic fluids of the present disclosure utilize additives that can meet the Denison HF0 standard along with strict environmental regulations like EcoLabel.
• the anti-wear additive is critical to the environmental performance because it typically contains chemistry that can be harmful for the environment.
• Amine phosphates e.g., IRGALUBE® 349 (Ciba Specialty Chemicals) may be used as a way of providing anti-wear benefits along with
• This type of additive can be utilized in a formulation up to 2.5% and more preferably at 1 %, 0.1 -0.5% and still meet the toxicity and performance requirements of the formulation. It is preferred that this additive chemistry has Nitrogen levels ⁇ 5% more preferably ⁇ 3%. Sulfur is a typical chemistry used in anti- wear/extreme pressure additives, this chemistry provides excellent performance where the environment is not concerned, but when looking for toxicity and biodegradability the sulfur levels should be 0% of the anti-wear/extreme pressure additive. Phosphorus is another common anti-wear/extreme pressure chemistry and the additive should have ⁇ 5% to meet the environmental considerations. In addition this chemistry can be biodegradable benefiting the overall formulation performance. Triphenyl
• TPPT phosphorothionate
• Amine Phosphates phosphorothionate
• the TPPT will contain sulfur and have higher levels of phosphorus, each typical >5%.
• the TPPT anti wear chemistry can only be used at treat rates up to 0.1 % to meet the environmental specifications due to this chemistry. At these low treat levels there is minimal impact to the overall biodegradability of the formulation.
• butylated triphenyl phosphorothionate chemistry can be used at appropriate levels.
• the HF-0 standard specifies high thermal stability, good rust prevention, high hydrolytic stability, good oxidation stability, low foaming, excellent filterability with and without water, and satisfactory performance in proprietary Denison pump tests.
• the HF-0 standard specifies the hydraulic oil have a viscosity index greater than 90, and a minimum aniline point of 100 °C (212 °F.).
• Wet filterability may be measured by the Denison TP 02100 test method or the AFNOR NFE 48-691 standard. For example, only fluids passing AFNOR NFE 48-691 are specified for injection molding hydraulic oils. The latter test measures filtration in the presence of water for an aged oil, which more closely replicates actual operating conditions. The tests measure the times taken to filter initial and subsequent volumes of oil, which are then used to calculate the Index of Filtration (IF). The closer the IF is to one, the lower the tendency to clog filters over time and therefore the more desirable the oil.
• IF Index of Filtration
• the hydraulic oils of this disclosure will have excellent demulsibility. That is, the number of minutes to 3 ml emulsion at 54 0 C. by ASTM D 1401 -12 is preferably less than 30 minutes, more preferably less than 20 minutes.
• One example formulation of the present disclosure yielded results shown in Table XIV.
• PAO poly-alpha-olefin
• API The American Petroleum Institute
• PAO base oil mainly consists of PAO with kinematic viscosity (at 40°C) of about 5.1 cSt.
• PAO base oil can only achieve less than 35% of biodegradation in 28 days when its kinematic viscosity (at 40°C) is greater than 31 cSt.
• Fig. 2 plots the results of percentage biodegradation of hydraulic oil formulated with biobased base oils according to one embodiment of the present disclosure, Exp-Hyd.BL.1 , over a period of 28 days.
• Exp-Hyd.BL.1 comprised of biobased hydrocarbon base oils, showed about 65% biodegradation at 28 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 hydraulic fluids.
• the foregoing examples demonstrate that the hydraulic fluids disclosed herein provide a hydraulic fluid that has superior or competitive properties to fluids previously available.
• Embodiment 1 A hydraulic fluid comprising a biobased hydrocarbon base oil having an average molecular weight (weight average) between 300 g/mol and 900 g/mol, and an additive package, the additive package comprising an anti-oxidant.
• Embodiment 3 A hydraulic fluid comprising a biobased base oil having the molecular structure:
• [P] is non-biobased hydrocarbon repeating unit
• n is greater than 1 , and m is less than 4;
• the stereoscopic arrangement of [B] and [P] repeating unit can be linear, branched, and cyclic.
• the molecular weight is in range of 300 g/mol to 900 g/mol; and the biobased content of the hydraulic fluid is greater than 20%, as measured by ASTM D6866-12.
• Embodiment 4 A hydraulic fluid comprising a biobased base oil, wherein at least about 20% of the carbon atoms in the biobased base oil originate from renewable carbon sources and the hydraulic fluid meets Denison Hydraulics standard HF-0.
• Embodiment 5 A hydraulic fluid comprising a biobased base oil, wherein at least about 20% of the carbon atoms in the biobased base oil originate from renewable carbon sources and the hydraulic fluid has a TAN ⁇ 2 at 1000 hours as determined in accordance with ASTM D943-04a (2010)e1 .
• Embodiment 6 A hydraulic fluid comprising a biobased hydrocarbon base oil, wherein at least about 20% of the carbon atoms in the biobased base oil originate from renewable carbon sources and the hydraulic fluid has a pour point of less than 40 °C.
• Embodiment 7 A hydraulic fluid comprising a biobased hydrocarbon base oil, the hydraulic fluid being compatible with and suitable for mixing with a Group I, Group II, or Group III hydraulic fluid.
• Embodiment 8 A hydraulic fluid having an ISO viscosity grade of 2 to 46,000 and comprising:
• Embodiment 9 The hydraulic fluid of embodiment 8 wherein the hydraulic fluid has an absence of any additional polymeric thickeners and viscosity index improvers.
• Embodiment 10 The hydraulic fluid according to embodiment 8 or 9, wherein the biobased hydrocarbon base oil is characterized by a viscosity index (VI) greater than 160, as measured in accordance with ASTM D2270-10e1 , and a branch ratio of less than 0.41 .
• VI viscosity index
• Embodiment 1 1 .
• Embodiment 12 The hydraulic fluid according to any of embodiments 8 to 1 1 , wherein the second basestock comprises a Group V base-stock selected from alkylated aromatics, polyalkylene glycols, esters, and mixtures thereof.
• Embodiment 13 The hydraulic fluid according to any of embodiments 8 to 12, wherein the hydraulic fluid comprises 5 to 50 wt % of the first basestock and 1 to 50 wt % of the second basestock.
• Embodiment 14 A hydraulic fluid comprising: (a) a base oil having a weight average molecular weight in the range of 400 to 600 g/mol, a viscosity index greater than 120 and less than 140; and (b) an anti-wear hydraulic oil additive package; wherein the hydraulic fluid has (i) an air release by ASTM D 3427-012 of less than 3 minutes at 50 °C, and (ii) a Sequence II foam tendency by ASTM D 892-13 of less than 50 ml, and a biodegradability rate of at least 60% as determined by OECD 301 B.
• Embodiment 15 The hydraulic fluid of embodiment 14, wherein the base oil comprises carbon from a renewable source.
• Embodiment 16 The hydraulic fluid of embodiment 14 or 15, wherein the base oil additionally has an average degree of branching in the molecules less than about 8 alkyl branches per 100 carbon atoms.
• Embodiment 17 The hydraulic fluid of embodiment 14, 15 or 16, wherein the base oil comprises at least 5 weight percent molecules with
• Embodiment 18 The hydraulic fluid of any of the preceding
• the base oil has a T90-T1 -0 boiling range distribution of less than 180 °F.
• Embodiment 19 The hydraulic fluid of any of the preceding
• the average molecular weight of the base oil is between about 500 and about 900 g/mol.
• Embodiment 20 The hydraulic fluid of any of the preceding
• Embodiment 21 The hydraulic fluid of any of the preceding enumerated embodiments, wherein the hydraulic fluid has an air release at 50 °C of less than 2.1 minutes.
• Embodiment 22 The hydraulic fluid of any of the preceding
• hydraulic fluid has an air release at 25 °C of less than 10 minutes.
• Embodiment 23 The hydraulic fluid of any of the preceding
• the base oil has an aniline point between 212 and 300 °F.
• Embodiment 24 The hydraulic fluid of any of the preceding
• Embodiment 25 The hydraulic fluid of any of the preceding
• Embodiment 26 The hydraulic fluid any preceding enumerated embodiment, wherein the hydraulic fluid has a number of minutes to 3 ml emulsion at 54 °C as determined in accordance with ASTM D1401 -12 of less than 30.
• Embodiment 27 The hydraulic fluid of any of the preceding
• Embodiment 28 The hydraulic fluid of any of the preceding
• the hydraulic fluid has an ISO viscosity grade of ISO 22, ISO 32, ISO 46, ISO 68, or ISO 100.
• Embodiment 29 The hydraulic fluid of any of the preceding
• Embodiment 30 The hydraulic fluid of any of embodiments 1 to 29, wherein the hydraulic fluid has an FZG gear wear rating determined in accordance with ASTM D5182-97 (2014) in excess of 1 1 .
• Embodiment 31 The hydraulic fluid of any of the preceding
• hydraulic fluid is biodegradable
• Embodiment 32 The hydraulic fluid of any of embodiments 1 to 30 wherein the hydraulic fluid has a biodegradable rate in excess of 60% according to by OECD 301 B.
• Embodiment 33 The hydraulic fluid of any of the preceding
• the base oil comprises a biobased terpene selected from the group consisting of myrcene, ocimene, farnesene, and combinations thereof.
• Embodiment 34 The hydraulic fluid of any of preceding enumerated embodiment, wherein the hydraulic fluid comprises an additive package.
• Embodiment 35 The hydraulic fluid of any of embodiments 1 to 33 wherein the hydraulic fluid comprises about 0.2 to about 2 wt % of an additive package.
• Embodiment 36 The hydraulic fluid of any of embodiments 1 to 33 wherein the hydraulic fluid comprises about 50 wt % to about 99 wt % biobased hydrocarbon base oil and from about 0.2 to about 2 wt % additive package.
• Embodiment 37 The hydraulic fluid of any of embodiments 34 to 36 wherein the additive package comprises at least one additive selected from the group consisting of anti-oxidants, anti-wear agents, extreme pressure agents, defoamants, detergent dispersant, rust and corrosion inhibitors, and demulsifiers.
• Embodiment 38 The hydraulic fluid of embodiment 37 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.
• Embodiment 39 The hydraulic fluid of any of the preceding
• Embodiment 40 The hydraulic fluid of any of embodiments 1 to 38 wherein the hydraulic fluid comprises less than 0.1 1 wt.% sulfated ash derived from the additive package.
• Embodiment 41 The hydraulic fluid of any of the preceding
• the hydraulic fluid contains between about 0.1 wt% and about 1 wt% of a phenolic anti-oxidant.
• Embodiment 42 The hydraulic fluid of any of the preceding
• Embodiment 43 The hydraulic fluid of embodiment 42 wherein the anti-wear additive contains an amine phosphate anti-wear additive and the hydraulic fluid further comprises up to about 1 wt% of the anti-wear additive(s).
• Embodiment 44 The hydraulic fluid of any of the preceding
• hydraulic fluid contains a viscosity index improver.
• Embodiment 45 The hydraulic fluid of embodiment 44 wherein the hydraulic fluid contains at least 1 wt% of the viscosity index improver.
• Embodiment 46 In an apparatus comprising a pump lubricated by a hydraulic fluid, the improvement comprising a hydraulic fluid according to any of the preceding enumerated embodiments.
• Embodiment 47 In a gear system, circulation lubrication system, hydraulic system, compressor system, vacuum pump, metal working machinery, electrical switch or connector comprising a hydraulic fluid, the improvement comprising a hydraulic fluid according to any preceding enumerated embodiment.

Landscapes

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

Priority Applications (2)

Applications Claiming Priority (2)

Publications (1)

Family

ID=54834448

Family Applications (1)

Country Status (3)

Cited By (4)

Families Citing this family (7)

Citations (6)

Family Cites Families (2)

• 2015
  • 2015-06-12 US US15/318,014 patent/US20170121630A1/en not_active Abandoned
  • 2015-06-12 WO PCT/US2015/035651 patent/WO2015192072A1/en active Application Filing
  • 2015-06-12 EP EP15806655.5A patent/EP3155081A4/de not_active Withdrawn

Patent Citations (6)

Non-Patent Citations (1)

Also Published As

Similar Documents

Legal Events