WO1998010042A1 - Liquides hydrauliques formes a partir d'un melange d'un ester d'alcool complexe avec d'autres huiles de base - Google Patents

Liquides hydrauliques formes a partir d'un melange d'un ester d'alcool complexe avec d'autres huiles de base Download PDF

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Publication number
WO1998010042A1
WO1998010042A1 PCT/US1997/015596 US9715596W WO9810042A1 WO 1998010042 A1 WO1998010042 A1 WO 1998010042A1 US 9715596 W US9715596 W US 9715596W WO 9810042 A1 WO9810042 A1 WO 9810042A1
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Prior art keywords
lubricating oil
alcohol
less
biodegradable
range
Prior art date
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PCT/US1997/015596
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English (en)
Inventor
Caroline B. Duncan
David W. Turner
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Exxon Chemical Patents Inc.
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Publication date
Application filed by Exxon Chemical Patents Inc. filed Critical Exxon Chemical Patents Inc.
Priority to AU43331/97A priority Critical patent/AU4333197A/en
Publication of WO1998010042A1 publication Critical patent/WO1998010042A1/fr

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    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
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    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
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Definitions

  • the present invention relates generally to blends of natural oils and/or hydrocarbon-based lubricant basestocks and/or synthetic lubricant basestocks with high viscosity complex alcohol esters for use as a unique hydraulic fluid that exhibits the following properties: biodegradable, good lubricity, good thermal and oxidative stability, high viscosity and very little or low toxicity.
  • enhanced lubricant basestocks formed by blending: (i) complex alcohol esters; and (ii) at least one other basestock selected from the group consisting of: synthetic oils (e.g., poly alpha olefins (PAO), polyalkylene glycols (PAG), phosphate esters, silicone oils, diesters and polyol esters), hydrocarbon-based oils (e.g., mineral oils and highly refined mineral oils) and natural oils (e.g., rapeseed, canola, and sunflower oils).
  • synthetic oils e.g., poly alpha olefins (PAO), polyalkylene glycols (PAG), phosphate esters, silicone oils, diesters and polyol esters
  • hydrocarbon-based oils e.g., mineral oils and highly refined mineral oils
  • natural oils e.g., rapeseed, canola, and sunflower oils.
  • Biodegradation is considered to have begun when 10% of the theoretical CO 2 has evolved. That is, a readily biodegradable fluid should have at least a 60% yield of CO 2 within 28 days, and this level must be reached within 10 days of biodegradation exceeding 10%. This is known as the "10-Day Window.”
  • the OECD guideline for testing the "ready biodegradability" of chemicals under the Modified Sturm test involves the measurement of the amount of CO 2 produced by the test compound which is measured and expressed as a percent of the theoretical CO 2 (ThCO 2 ) it should have produced calculated from the carbon content of the test compound. Biodegradability is therefore expressed as a percentage of ThCO 2 .
  • the Modified Sturm test is run by spiking a chemically defined liquid medium, essentially free of other organic carbon sources, with the test material and inoculated with sewage micro-organisms. The CO 2 released is trapped as BaCO 3 . After reference to suitable blank controls, the total amount of
  • CO 2 produced by the test compound is determined for the test period and calculated as the percentage of total CO 2 that the test material could have theoretically produced based on carbon composition See G. van der Waal and D. Kenbeek, "Testing, Application, and Future Development of Environmentally Friendly Ester Based Fluids", Journal of Synthetic Lubrication, Nol. 10, Issue No. 1, April 1993, pp. 67-83, which is incorporated herein by reference.
  • rapeseed oil i.e., a triglyceride of fatty acids, e.g., 7 % saturated C ⁇ 2 to C ⁇ 8 acids, 50% oleic acid, 36% linoleic acid and 7% linolenic acid, having the following properties: a viscosity at 40°C of 47.8 cSt, a pour point of 0°C, a flash point of 162°C and a biodegradability of 85% by the Modified Sturm test. Although it has very good biodegradability, its use in biodegradable lubricant applications is limited due to its poor low temperature properties and poor stability.
  • esters synthesized from both linear acids and linear alcohols tend to have poor low temperature properties. Even when synthesized from linear acids and highly branched alcohols, such as polyol esters of linear acids, high viscosity esters with good low temperature properties can be difficult to achieve.
  • pentaerythritol esters of linear acids exhibit poor solubility with dispersants such as polyamides, and trimethylolpropane esters of low molecular weight (i.e., having a carbon number less than 14) linear acids do not provide sufficient lubricity. This lower quality of lubricity is also seen with adipate esters of branched alcohols.
  • Branched synthetic polyol esters have been used extensively in non- biodegradable applications, such as refrigeration lubricant applications, and have proven to be quite effective if 3,5,5 -trimethylhexanoic acid is incorporated into the molecule at 25 molar percent or greater.
  • trimethylhexanoic acid is not biodegradable as determined by the Modified Sturm test (OECD 301B), and the incorporation of 3, 5, 5 -trimethylhexanoic acid, even at 25 molar percent, would drastically lower the biodegradation of the polyol ester due to the quaternary carbons contained therein.
  • trialkyl acetic acids i.e., neo acids
  • neo acids trialkyl acetic acids
  • Polyol esters of all branched acids can be used as refrigeration oils as well. However, they do not rapidly biodegrade as determined by the Modified Sturm Test (OECD 301B) and, therefore, are not desirable for use in biodegradable applications.
  • blends of natural, hydrocarbon- based and/or synthetic lubricant basestocks with high viscosity complex alcohol esters unexpectedly provide a lubricating basestock having the following desirable properties biodegradability, high viscosity, good pour point, good thermal and oxidative stability, low toxicity, excellent lubricity, and seal compatibility
  • complex alcohol esters can be produced which have: reduced cost (approximately half the cost of complex acid esters), high viscosity (greater than 100 cSt at 40°C), good thermal and oxidative stability, good biodegradability, low toxicity, good low temperature properties, and excellent lubricity
  • reduced cost approximately half the cost of complex acid esters
  • high viscosity greater than 100 cSt at 40°C
  • good thermal and oxidative stability good biodegradability
  • low toxicity good low temperature properties
  • excellent lubricity When blended with lower viscosity oils, a wide range of iso grade products can be produced which meet stringent end- use specifications.
  • the present inventors have discovered that when the amount of linear monohydric alcohol exceeds 20% of the total alcohol used, then the pour point is too high, e.g., above -30°C.
  • the present inventors have discovered that the ratio of polybasic acid to polyol is critical in the formation of a complex alcohol ester. That is, if this ratio is too low then a complex alcohol ester contains undesirable amounts of heavies which reduces biodegradability and increases the hydroxyl number of the ester which increases the corrosive nature of the resultant ester which is also undesirable. If, however, the ratio is too high then the resultant complex alcohol ester will have an undesirably low viscosity (reducing its applicability in certain iso grade applications) and poor seal swell characteristics.
  • Other conventional natural, hydrocarbon-based and/or synthetic basestocks may each provide one or more of the desired attributes, e.g., high viscosity, good low temperature properties, biodegradability, lubricity, seal compatibility, low toxicity, and good thermal and oxidative stability, but none appears to be able to meet all of the product attributes by themselves.
  • some synthetic esters are capable of meeting the high viscosity property, but fail the biodegradability, low temperature requirements, or low toxicity requirements.
  • the natural basestocks such as rapeseed oil are capable of meeting the biodegradability and toxicity properties, but fail to meet the required high viscosity, lubricity, and thermal and oxidative stability properties.
  • the blended basestock unexpectedly exhibits enhanced product attributes versus either the complex alcohol ester or other basestock by itself
  • the blended basestocks according to the present invention exhibit the following attributes: excellent lubricity, seal compatibility, biodegradability, no or little toxicity, good low temperature properties, a wide viscosity range to meet various iso grade needs, and/or good thermal and oxidative stability.
  • the hydraulic fluids formed from the blended basestocks of the present invention are capable of being used in environmentally sensitive areas. They are typically boidegradable (>60%) and non-toxic. Most hydraulic fluids used today are comprised of mineral oils and additives. They are not biodegradable and in many cases, because of the additives, are considered toxic. Because of the unique properties of the blended basestocks of the present invention (i.e., very stable, biodegradable, non-toxic, wide iso grade range, excellent lubricating properties), the additives needed to meet the physical demands made on these hydraulic fluids are minimal. In addition to requiring less additives, the requirements of the additives needed is less stringent. Therefore, less toxic additives can replace the more toxic additives and still meet the requirements.
  • blended basestocks of the present invention for instance, have a high level of oxidative stability and anti- oxidants can be eliminated or significantly reduced. These blended basestocks of the present invention have good low temperature properties and additives such as pour point suppressors are not required. Moreover, these blended basestocks lubricate, therefore extreme pressure wear additives can be minimized. ZDDP, for example, is not required to meet lubricity requirements such as four-ball wear and FZG.
  • the blended basestocks according to the present invention do not contain
  • ZDDP rapeseed oil formulations
  • ZDDP is toxic to most aquatic life it is undesirable in hydraulic fluid applications.
  • a hydraulic fluid which comprises: (1) a complex alcohol ester having the reaction product of: a polyhydroxyl compound represented by the general formula: R(OH) n wherein R is any aliphatic or cyclo-aliphatic hydrocarbyl group and n is at least 2, provided that the hydrocarbyl group contains from about 2 to 20 carbon atoms; a polybasic acid or an anhydride of a polybasic acid; and a branched and/or linear monohydric alcohol, provided that the alcohol is added in an amount which is less than 20% excess; (2) at least one additional basestock selected from the group consisting of: natural oils, hydrocarbon-based oils and synthetic oils; and (3) an appropriate hydraulic fluid additive package, wherein the hydraulic fluid exhibits the following properties: excellent lubricity as determined by the FZG pump wear test (DIN 51354); good stability as evidenced by the results of such tests as RBOT (Rotary Bomb Oxidation Test (ASTM No.
  • the biodegradable lubricating oil according to the present invention comprises an add mixture of the following components (A) 10-60 wt % of a complex alcohol ester basestock which comprises the reaction product of an add mixture of the following (1) a polyhydroxyl compound represented by the general formula
  • R(OH) n wherein R is any aliphatic or cyclo-aliphatic hydrocarbyl group and n is at least 2, provided that said hydrocarbyl group contains from about 2 to 20 carbon atoms,
  • the unique complex alcohol ester according to the present invention exhibits the following properties: lubricity, as measured by the coefficient of friction, of less than or equal to 0.1; a pour point of less than or equal to -30°C, preferably -40°C; no volatile organic components; and thermal/oxidative stability as measured by HPDSC at 220°C and 3.445 MPa air of greater than 10 minutes with
  • the complex alcohol ester also exhibits at least one of the properties selected from the group consisting of: (a) a total acid number of less than or equal to about 1.0 mgKOH/gram, (b) a hydroxyl number in the range between about 0 to 50 mgKOH/gram, (c) a metal catalyst content of less than about 25 ppm, (d) a molecular weight in the range between about 275 to 250,000 Daltons, (e) a seal swell equal to about diisotridecyladipate, (f) a viscosity at -25°C of less than or equal to about 100,000 cps, (g) a flash point of greater than about 200°C, (h) aquatic toxicity of greater than about 1,000 ppm, (I) a specific gravity of less than about 1.0, and (j) a viscosity index equal to or greater than about 150.
  • the properties selected from the group consisting of: (a) a total acid number of less than or equal to about 1.0 mgKOH/
  • the additional biodegradable basestock is at least one oil selected from the group consisting of: natural oil and biodegradable synthetic oils.
  • the preferred biodegradable synthetic oil comprises the reaction product of: a branched or linear alcohol having the general formula R(OH) n , wherein R is an aliphatic or cyclo-aliphatic group having from about 2 to 20 carbon atoms and n is at least 2; and mixed acids comprising about 30 to 80 molar % of a linear acid having a carbon number in the range between about C 5 to Cn, and about 20 to 70 molar % of at least one branched acid having a carbon number in the range between about C5 to C, .
  • these hydraulic fluids exhibit excellent lubricity and typically comprise an add mixture of the following components: (A) 2-30 wt.% of a complex alcohol ester basestock which comprises the reaction product of an add mixture of the following: (1) a polyhydroxyl compound represented by the general formula: R(OH) n wherein R is any aliphatic or cyclo-aliphatic hydrocarbyl group and n is at least 2, provided that said hydrocarbyl group contains from about 2 to 20 carbon atoms; (2) a polybasic acid or an anhydride of a polybasic acid, provided that the ratio of equivalents of said polybasic acid to equivalents of alcohol from said polyhydroxyl compound is in the range between about 1.6: 1 to 2: 1 ; and (3) a monohydric alcohol, provided that the ratio of equivalents of said monohydric alcohol to equivalents of said polybasic acid is in the range between about 0.84: 1 to 1.2: 1; wherein said complex alcohol ester exhibits a viscosity in the range between
  • the complex alcohol ester is added primarily for biodegradability, good lubricity, low toxicity and high viscosity, and usually replaces or significantly reduces a metal extreme pressure (EP) wear additive such as one of the ZDDP family.
  • EP metal extreme pressure
  • the complex alcohol ester is added primarily for its high viscosity (greater than 100 cSt at 40°C) and biodegradability (greater than 60% after 28 days as measured by the Modified Sturm test).
  • the over-all additive package can be formulated to minimize environmental impact due to the performance of the basestock blends.
  • This unique blend of complex alcohol ester and biodegradable branched synthetic ester basestocks preferably exhibits at least one of the properties selected from the group consisting of: (a) excellent lubricity as evidenced by the elimination or reduction of toxic extreme pressure wear additives; (b) good stability as evidenced by tests such as RBOT test; (c) good low temperature properties as evidenced by pour points less than -30°C and -25°C Brookfield viscosities of less than 8500 cps; (d) biodegradability of greater than 60% in 28 days as measured by the Modified Sturm test; (e) low toxicity (greater than 1,000 ppm); (f) good seal compatibility; (g) high flash point (greater than 200°C) to reduce volatile organic components (NOC's), and (h) low toxicity.
  • the basestock blend When the lubricating oil is comprised of a complex alcohol ester with a viscosity greater than 100 cSt at 40°C and either a hydrocarbon-based oil or synthetic oil, then the basestock blend preferably exhibits sufficient lubricity to eliminate or significantly reduce the need for toxic extreme pressure wear additives such as ZDDP and other metal containing materials.
  • the complex alcohol ester is preferably added in an amount between about 2 to 30 wt.% and the hydrocarbon-based oil and/or synthetic oils are added in an amount between 70 to 98 wt.%.
  • the basestock blend preferably exhibits at least one of the properties selected from the group consisting of: (a) excellent lubricity as evidenced by the elimination or reduction of toxic extreme pressure wear additives; (b) good stability as evidenced by tests such as RBOT test; (c) good low temperature properties as evidenced by pour points less than -
  • the complex alcohol ester be added in an amount between about 10-60 wt.% and the other biodegradable basestock ester be added in an amount between about 40-90 wt.%
  • the additive package preferably comprises at least one additive selected from the group consisting of: viscosity index improvers, corrosion inhibitors, boundary lubrication agents, demulsifiers, pour point depressants, and antifoaming agents.
  • High viscosity complex alcohol esters provide a unique level of biodegradability in conjunction with effective lubricating properties even at low concentrations (i.e., less than 5 wt.%), especially designed for hydraulic fluid applications.
  • TAN total acid number
  • di-ester content low (i.e., less than 0.7 mgKOH/gram and less than 45 wt.%, respectively), and the esterification catalyst is effectively removed to a level of less than 25 ppm
  • high viscosity complex alcohol esters also provided excellent stability, good seal compatibility, and low toxicity.
  • the present inventors have discovered that these unique high viscosity, low metals/low acid complex alcohol esters, when blended with other natural, hydrocarbon-based and/or synthetic basestocks, result in lubricant basestocks which exhibit biodegradability, excellent lubricity, high viscosity and low toxicity depending upon which additional basestock the complex alcohol ester is blended with and concentration of the complex alcohol ester in the blend.
  • the preferred lubricant according to the present invention is a blend of the described complex alcohol ester composition and at least one additional basestock selected from the group consisting of: natural oils (e.g., rapeseed oil, canola oil and sunflower oil) and/or hydrocarbon-based oils (e.g., mineral oils and highly refined mineral oils and/or synthetic oils (e.g., poly alpha olefins (PAO), polyalkylene glycols (PAG), polyisobutylene (PIB), phosphate esters, silicone oils, diesters, and polyol esters); and a lubricant additive package.
  • natural oils e.g., rapeseed oil, canola oil and sunflower oil
  • hydrocarbon-based oils e.g., mineral oils and highly refined mineral oils and/or synthetic oils (e.g., poly alpha olefins (PAO), polyalkylene glycols (PAG), polyisobutylene (PIB), phosphate esters, silicone oils
  • Blended hydraulic fluids according to the present invention preferably include 2 to 30 wt.% complex alcohol ester and 70 to 98 wt.% of a second basestock selected from natural oils, hydrocarbon-based oils, and/or synthetic oils.
  • a second basestock selected from natural oils, hydrocarbon-based oils, and/or synthetic oils.
  • the complex alcohol ester according to the present invention is blend with a biodegradable synthetic or natural ester basestock, it is preferably added in an amount between about 10 to 60 wt.% and the biodegradable branched synthetic ester basestock is added in an amount between about 40 to 90 wt.%.
  • COMPLEX ALCOHOL ESTERS COMPLEX ALCOHOL ESTERS
  • One preferred complex alcohol ester the reaction product of an add mixture of the following: a polyhydroxyl compound represented by the general formula: R(OH) n wherein R is any aliphatic or cyclo-aliphatic hydrocarbyl group and n is at least 2, provided that the hydrocarbyl group contains from about 2 to 20 carbon atoms; a polybasic acid or an anhydride of a polybasic acid, provided that the ratio of equivalents of the polybasic acid to equivalents of alcohol from the polyhydroxyl compound is in the range between about 1.6: 1 to 2: 1 ; and a monohydric alcohol, provided that the ratio of equivalents of the monohydric alcohol to equivalents of the polybasic acid is in the range between about 0.84: 1 to 1.2: 1 ; wherein the complex alcohol ester exhibits a pour point of less than or equal to -30°C, a viscosity in the range between about 100-700 cSt at 40°C, preferably 100-200 cSt, and having a
  • the present inventors have unexpectedly discovered that if the ratio of polybasic acid to polyol (i.e., polyhydroxyl compound) is too low, then an unacceptable amount of cross-linking occurs which results in very high viscosities, poor low temperature properties, poor biodegradability, and poor compatibility with other basestocks and with additives. If, however, the ratio of polybasic acid to polyol is too high, then an unacceptable amount of polybasic acid ester (e.g., adipate di-ester) is formed resulting in poor seal compatibility and low viscosity which limits the complex alcohol ester's applicability.
  • polybasic acid to polyol i.e., polyhydroxyl compound
  • the present inventors have also discovered that if the ratio of monohydric alcohol to polybasic acid is too low, i.e., less than 0.96 to 1 , then an unacceptably high acid number, sludge concentration, deposits, and corrosion occur. If, however, the ratio of monohydric alcohol to polybasic acid is too high (i.e., 1.2 to 1), then an unacceptable amount of polybasic acid ester is formed resulting in poor seal compatibility and low viscosity which limits the complex alcohol ester's applicability
  • the complex alcohol ester according to the present invention exhibits the following properties lubricity, as measured by the coefficient of friction, of less than or equal to 0 1 , a pour point of less than or equal to -30°C, preferably -40°C, biodegradability of greater than 60%, as measured by the Sturm test (e g , Modified Sturm test), an aquatic toxicity of greater than 1,000 ppm, no volatile organic components, and thermal/oxidative stability as measured by HPDSC at 220°C and 3 445 MPa air of greater than 10 minutes with 0 5 wt % of an antioxidant
  • the ratio of equivalents of the polybasic acid to equivalents of alcohol from the polyhydroxyl compound is in the range between about 1 75 1 to 2 1
  • the polyhydroxyl compound is at least one compound selected from the group consisting of t ⁇ methylolpropane, trimethylolethane and t ⁇ methylolbutane
  • the ratio of equivalents of the polybasic acid to equivalents of alcohol from the polyhydroxyl compound is in the range between about 1 6 1 to 2 1
  • the polyhydroxyl compound is di-pentaeryth ⁇ tol, then the ratio of equivalents of the polybasic acid to equivalents of alcohol from the polyhydroxyl compound is in the range between about 1 83 1 to 2 1
  • the monohydric alcohol may be at least one alcohol selected from the group consisting of branched and linear C5 to Cn alcohol
  • the linear monohydric alcohol is preferably present in an amount between about 0 to 30 mole%, more preferably between about 5 to 20 mole%
  • the monohydnc alcohol is at least one alcohol selected from the group consisting of C 8 to C10 iso-oxo alcohols
  • one highly preferred complex alcohol ester is formed from the reaction product of the admixture of trimethylolpropane, adipic acid and either isodecyl alcohol or 2- ethylhexanol.
  • the unique complex alcohol esters according to the present invention preferably exhibit at least one of the properties selected from the group consisting of: (a) a total acid number of less than or equal to about 1.0 mgKOH/gram, (b) a hydroxyl number in the range between about 0 to 50 mgKOH/gram, (c) a metal catalyst content of less than about 25 ppm, (d) a molecular weight in the range between about 275 to 250,000 Daltons, (e) a seal swell equal to about diisotridecyladipate, (f) a viscosity at -25°C of less than or equal to about 100,000 cps, (g) a flash point of greater than about 200°C, (h) aquatic toxicity of greater than about 1,000 ppm, (i) a specific gravity of less than about 1.0, and (j) viscosity index equal to or greater than about 150.
  • the present inventors have synthesized a composition and a method of production of that composition which provides a high viscosity oil having good low temperature properties, low metals, low acidity, high viscosity index, and acceptable rates of biodegradability as measured by the Modified Sturm test
  • Oxo alcohols are manufactured via a process, whereby propylene and other olefins are oligomerized over a catalyst (e.g., a phosphoric acid on Kieselguhr clay) and then distilled to achieve various unsaturated (olefinic) streams largely comprising a single carbon number. These streams are then reacted under hydroformylation conditions using a cobalt carbonyl catalyst with synthesis gas (carbon monoxide and hydrogen) so as to produce a multi-isomer mix of aldehydes/alcohols. The mix of aldehydes/alcohols is then introduced to a hydrogenation reactor and hydrogenated to a mixture of branched alcohols comprising mostly alcohols of one carbon greater than the number of carbons in the feed olefin stream.
  • a catalyst e.g., a phosphoric acid on Kieselguhr clay
  • synthesis gas carbon monoxide and hydrogen
  • One particularly preferred oxo-alcohol is isodecyl alcohol, prepared from the corresponding C 9 olefin.
  • the alcohol is isodecyl alcohol
  • the polyol is trimethylolpropane
  • the acid is the C 6 diacid, e.g. adipic acid
  • a preferred complex alcohol ester is attained.
  • the present inventors have surprisingly discovered that this complex alcohol ester, wherein the alcohol is a branched oxo- alcohol has a surprisingly high viscosity index of ca. 150 and is surprisingly biodegradable as defined by the Modified Sturm test.
  • This complex alcohol ester can be prepared with a final acidity (TAN) of less than 0.7 mg KOH/gram and with a conversion of the adipic acid of greater than 99%.
  • TAN final acidity
  • a catalyst is required, and further, it is preferable to add the catalyst within a relatively narrow conversion window.
  • the present inventors have discovered that the catalyst can also be added at anytime during the reaction product and removed to an amount of less than 25 ppm and still obtain a final acidity (TAN) of less than 0.7 mg KOH/gram, so long as the esterification reaction is followed by a hydrolysis step wherein water is added in an amount of between about 0.5 to 4 wt.%, based on crude esterification product, more preferably between about 2 to 3 wt. %, at elevated temperatures of between about 100 to 200°C, more preferably between about 125 to 175°C, and most preferably between about 140 to 160°C, and pressures greater than one atmosphere.
  • Such high temperature hydrolysis can successfully remove the catalyst metals to less than 25 ppm without increasing the TAN to greater than 0.7 mgKOH/gram.
  • the low metals and low acid levels achieved by use of this novel high temperature hydrolysis step is completely unexpected.
  • the present inventors have discovered that the actual product is a broad mix of molecular weights of esters and that, if so desired, an amount of diisodecyl adipate can be removed from the higher molecular weight ester via wipefilm evaporation or other separation techniques if desired.
  • the present inventors have also discovered that highly stable complex alcohol esters can be produced that are resistant to viscosity increases during heating. This is accomplished by synthesizing complex alcohol esters with a low hydroxyl number by limiting the ratio of polybasic acid, polyol and monohydric alcohol. These highly stable complex alcohol esters exhibit no increase in viscosity when heated to temperatures above 200°C, while similar esters with high hydroxyl numbers increase in viscosity from 5 to 10% under similar conditions.
  • any C$ to C ⁇ 3 branched and/or linear monohydric alcohol selected from the group consisting of: isopentyl alcohol, n-pentyl alcohol, isohexyl alcohol, n-hexyl alcohol, isoheptyl alcohol, n-heptyl alcohol, iso-octyl alcohol (e.g., 2-ethyl hexanol or iso-octyl alcohol), n-octyl alcohol, iso-nonyl alcohol, n-nonyl alcohol, isodecyl alcohol, and n-decyl alcohol; provided that the amount of linear monohydric alcohol is present in the range between about 0-20 mole %, based on the total amount of monohydric alcohol.
  • Oxo alcohols are manufactured via a process, whereby propyiene and other olefin s are oligomerized over a catalyst (e.g., a phosphoric acid on Kieselguhr clay) and then distilled to achieve various unsaturated (olefinic) streams largely comprising a single carbon number. These streams are then reacted under hydroformylation conditions using a cobalt carbonyl catalyst with synthesis gas (carbon monoxide and hydrogen) so as to produce a multi-isomer mix of aldehydes/alcohols. The mix of aldehydes/alcohols is then introduced to a hydrogenation reactor and hydrogenated to a mixture of branched alcohols comprising mostly alcohols of one carbon greater than the number of carbons in the feed olefin stream.
  • a catalyst e.g., a phosphoric acid on Kieselguhr clay
  • synthesis gas carbon monoxide and hydrogen
  • the branched oxo alcohols are preferably monohydric oxo alcohols which have a carbon number in the range between about C5 to C ⁇ 3 .
  • the most preferred monohydric oxo alcohols according to the present invention include iso-octyl alcohol, e.g., ExxalTM 8 alcohol, formed from the cobalt oxo process and 2- ethylhexanol which is formed from the rhodium oxo process.
  • iso is meant to convey a multiple isomer product made by the oxo process. It is desirable to have a branched oxo alcohol comprising multiple isomers, preferably more than 3 isomers, most preferably more than 5 isomers.
  • Branched oxo alcohols may be produced in the so-called "oxo" process by hydroformylation of commercial branched C 4 to C ⁇ 2 olefin fractions to a corresponding branched C5 to C ⁇ 3 alcohol/aldehyde-containing oxonation product.
  • oxo branched C 4 to C ⁇ 2 olefin fractions
  • branched C5 to C ⁇ 3 alcohol/aldehyde-containing oxonation product it is desirable to form an alcohol/aldehyde intermediate from the oxonation product followed by conversion of the crude oxo alcohol/aldehyde product to an all oxo alcohol product.
  • the production of branched oxo alcohols from the cobalt catalyzed hydroformylation of an olefinic feedstream preferably comprises the following steps: (a) hydroformylating an olefinic feedstream by reaction with carbon monoxide and hydrogen (i.e., synthesis gas) in the presence of a hydroformylation catalyst under reaction conditions that promote the formation of an alcohol/aldehyde-rich crude reaction product;
  • the olefinic feedstream is preferably any C 4 to C ⁇ 2 olefin, more preferably branched C to C9 olefins. Moreover, the olefinic feedstream is preferably a branched olefin, although a linear olefin which is capable of producing all branched oxo alcohols is also contemplated herein.
  • the hydroformylation and subsequent hydrogenation in the presence of an alcohol-forming catalyst is capable of producing branched C5 to C ⁇ 3 alcohols, more preferably branched C « alcohol (i.e., ExxalTM 8), branched C 9 alcohol (i.e., ExxalTM 9), and isodecyl alcohol.
  • Each of the branched oxo C5 to C ⁇ 3 alcohols formed by the oxo process typically comprises, for example, a mixture of branched oxo alcohol isomers, e.g., ExxalTM 8 alcohol comprises a mixture of 3,5-dimethyl hexanol, 4,5-dimethyl hexanol, 3,4-dimethyl hexanol, 5 -methyl heptanol, 4-methyl heptanol and a mixture of other methyl heptanols and dimethyl hexanols.
  • ExxalTM 8 alcohol comprises a mixture of 3,5-dimethyl hexanol, 4,5-dimethyl hexanol, 3,4-dimethyl hexanol, 5 -methyl heptanol, 4-methyl heptanol and a mixture of other methyl heptanols and dimethyl hexanols.
  • any type of catalyst known to one of ordinary skill in the art which is capable of converting oxo aldehydes to oxo alcohols is contemplated by the present invention. It is preferable that the linear monohydric alcohol be present in an amount between about 0 to 30 mole%, preferably between about 5 to 20 mole%.
  • POLYOLS Among the polyols (i.e., polyhydroxyl compounds) which can be reacted with the diacid and monohydric alcohol are those represented by the general formula:
  • R(OH) n wherein R is any aliphatic or cyclo-aliphatic hydrocarbyl group (preferably an alkyl) and n is at least 2.
  • the hydrocarbyl group may contain from about 2 to about 20 or more carbon atoms, and the hydrocarbyl group may also contain substituents such as chlorine, nitrogen and/or oxygen atoms.
  • the polyhydroxyl compounds generally may contain one or more oxya'lkylene groups and, thus, the polyhydroxyl compounds include compounds such as polyetherpolyols.
  • the number of carbon atoms i.e., carbon number, wherein the term carbon number as used throughout this application refers to the total number of carbon atoms in either the acid or alcohol as the case may be
  • number of hydroxy groups i.e., hydroxyl number
  • the following alcohols are particularly useful as polyols: neopentyl glycol, trimethylolethane, trimethylolpropane, trimethylolbutane, mono-pentaerythritol, technical grade pentaerythritol, and di-pentaerythritol.
  • the most preferred alcohols are technical grade (e.g., approximately 88% mono-, 10% di- and 1-2% tri- pentaerythritol) pentaerythritol, monopentaerythritol, di-pentaerythritol, and trimethylolpropane.
  • Selected polybasic or polycarboxylic acids include any C 2 to C ⁇ 2 diacids, e.g., adipic, azelaic, sebacic and dodecanedioic acids.
  • Anhydrides of polybasic acids can be used in place of the polybasic acids, when esters are being formed. These include succinic anhydride, glutaric anhydride ⁇ adipic anhydride, maleic anhydride, phthalic anhydride, nadic anhydride, methyl nadic anhydride, hexahydrophthalic anhydride, and mixed anhydrides of polybasic acids.
  • the lubricating oils contemplated for use with the complex alcohol ester compositions of the present invention include natural oils, synthetic oils and hydrocarbon-based oils of lubricating viscosity and mixtures thereof.
  • the synthetic oils include long chain alkanes such as cetanes and olefin polymers such as oligomers of hexene, octene, decene, and dodecene, etc
  • the other synthetic oils include (1) fully esterified ester oils, with no free hydroxyls, such as pentaerythritol esters of monocarboxylic acids having 2 to 20 carbon atoms, trimethylol propane esters of monocarboxylic acids having 2 to 20 carbon atoms, (2) polyacetals and
  • siloxane fluids are those made from polycarboxylic acids and monohydric alcohols.
  • the basestock blend can be used in the formulation of hydraulic fluids together with selected lubricant additives.
  • the preferred hydraulic fluids are typically formulated using the basestock blend formed according to the present invention together with any conventional hydraulic fluid additive package.
  • the additives listed below are typically used in such amounts so as to provide their normal attendant functions.
  • the additive package may include, but is not limited to, viscosity index improvers, corrosion inhibitors, boundary lubrication agents, demulsifiers, pour point depressants, and antifoaming agents.
  • the hydraulic fluid according to the present invention can employ typically about 90 to 99% basestock blend, with the remainder comprising an additive package.
  • One preferred additional basestock is a biodegradable synthetic ester basestock which comprises the reaction product of: a branched or linear alcohol having the general formula R(OH) n , wherein R is an aliphatic or cyclo-aliphatic group having from about 2 to 20 carbon atoms and n is at least 2; and mixed acids comprising about 30 to 80 molar %, preferably 35 to 55 molar %, of a linear acid having a carbon number in the range between about C 5 to d 2 , preferably between about C 7 to Cio, and about 20 to 70 molar %, preferably 35 to 55 molar %, of at least one branched acid having a carbon number in the range between about C 5 to C [3 ; wherein the ester basestock exhibits the following properties; at least 60% biodegradation in 28 days as measured by the Modified Sturm test; a pour point of less than -25°C; a viscosity of less than 7500 cps at -25°C; and
  • the biodegradable synthetic ester basestock preferably comprises multiple isomers, i.e., at least 3 isomer or more, preferably greater than 3 to 5 isomers.
  • the branched acid is predominantly a doubly branched or an alpha branched acid having an average branching per molecule in the range between about 0.3 to 1.9.
  • the branched acid is at least one acid selected from the group consisting of 2-ethylhexanoic acids, isoheptanoic acids, isooctanoic acids, isononanoic acids, and isodecanoic acids.
  • a preferred dispersant for hydraulic fluid formulations comprises a major amount of at least one oil of lubricating viscosity and a minor amount of a functionalized and derivatized hydrocarbon; wherein functionalization comprises at least one group of the formula -CO-Y-R 3 wherein Y is O or S, R 3 is aryl, substituted hydrocarbyl, and -Y-R 3 has a pKa of 12 or less, wherein at least 50 mole % of the functional groups are attached to a tertiary carbon atom; and wherein said functionalized hydrocarbon is derivatized by a nucleophilic reacta ⁇ t.
  • the nucleophilic reactant is selected from the group consisting of alcohols and amines.
  • DIDA Diisodecyladipate
  • Table 1 compares a variety of complex alcohol esters versus a conventional branched ester to demonstrate the increased biodegradability and thermal and oxidative stability of the complex alcohol esters according to the present invention.
  • OIT denotes oxidation induction time (minutes until decomposition)
  • HPDSC denotes high pressure differential calo ⁇ metry
  • TMP is t ⁇ methylolpropane
  • AA is adipic acid
  • IHA isohexyl alcohol
  • TPE is technical grade pentaerythritol ⁇ so-Ci8 is lsostearate
  • the branched acid ester and the complex alcohol ester formed without st ⁇ pping exhibited undesirable pour points, i e , -20 and -14°C, respectively, and undesirable viscosities at -25°C, i e , 358,000 cps and a solid product, respectively
  • 1770 denotes a 70:30 mixture of n-C and ⁇ -branched C 7 , respectively .
  • DI denotes dispersant additive package.
  • INA denotes isononylalcohol.
  • EXAMPLE 4 Set forth below in Tables 3 and 4 are various blends of hydraulic fluids and their respective percent biodegradation, the iso grade, hydrolytic stability as measured by RBOT (Rotary Bomb Oxidation test, ASTM D2272), FZG (i.e., pump wear test, DIN 51354), and wear scar diameter (4-Ball War Scar Diameter, (40 kg, 75°C, 1200 rpm, 60 minutes) mm.
  • C810 is a mixture of linear C 8 and C] 0 acids.
  • Ck8 is an iso-octyl alcohol form from the cobalt oxo process.
  • AA is adipic acid
  • DIDA is diisodecyl adipate
  • TPE is technical grade pentaerythritol
  • TMP is trimethylo.propane
  • Rapeseed Oil - 32 cSt 118 - 0.40
  • Samples contain 0.9 to 5.0 wt.% Adpack.
  • C810 is a mixture of linear Cg and Ci 0 acids.
  • Ck8 is an iso-octyl alcohol form from the cobalt oxo process.
  • AA is adipic acid
  • IDA isodecyl alcohol
  • DIDA is diisodecyl adipate
  • TPE is technical grade pentaerythritol
  • TMP is trimethylolpropane

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Abstract

La présente invention porte sur un liquide hydraulique préparé à partir des composantes suivantes: (1) une huile lubrifiante comprenant: (a) un ester d'alcool complexe contenant le produit de réaction constitué par: un composé de polyhydroxyle représenté par la formule générale: R(OH)n où R représente tout groupe hydrocarbyle aliphatique ou cyclo-aliphatique et où n est au moins égal à 2, étant entendu que ledit groupe hydrocarbyle contient entre environ 2 et 20 atomes de carbone; (2) un acide polybasique ou un anhydride d'un acide polybasique; et un alcool monohydrique ramifié et/ou linéaire, étant entendu que la quantité de l'alcool ajouté ne dépasse pas 20 %, et où la concentration de l'ester d'acide polybasique est inférieure ou égale à 70 % en poids, en fonction de l'ester d'alcool complexe; et b) au moins une huile de base supplémentaire; et (2) un ensemble d'additifs; où le liquide hydraulique offre une meilleure biodégradabilité, un meilleur pouvoir lubrifiant, une haute viscosité, et/ou présente l'avantage d'être non toxique.
PCT/US1997/015596 1996-09-06 1997-09-05 Liquides hydrauliques formes a partir d'un melange d'un ester d'alcool complexe avec d'autres huiles de base WO1998010042A1 (fr)

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WO2015192072A1 (fr) * 2014-06-12 2015-12-17 Novvi Llc Fluides hydrauliques issus d'isoparaffines renouvelables
EP3098288A4 (fr) * 2014-01-21 2017-03-01 JX Nippon Oil & Energy Corporation Composition de fluide de travail pour une machine de réfrigération et huile pour machine de réfrigération
US11208607B2 (en) 2016-11-09 2021-12-28 Novvi Llc Synthetic oligomer compositions and methods of manufacture
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GB1460665A (en) * 1974-02-11 1977-01-06 Ciba Geigy Ag Transmission device
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WO2000029521A1 (fr) * 1998-11-16 2000-05-25 Exxon Chemical Patents Inc. Compositions et composes complexes solubles d'ester d'alcool
WO2005111179A1 (fr) * 2004-05-13 2005-11-24 Imperial Chemical Industries Plc Formulations antiusure pour automobiles
EP3098288A4 (fr) * 2014-01-21 2017-03-01 JX Nippon Oil & Energy Corporation Composition de fluide de travail pour une machine de réfrigération et huile pour machine de réfrigération
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US11208607B2 (en) 2016-11-09 2021-12-28 Novvi Llc Synthetic oligomer compositions and methods of manufacture
US11332690B2 (en) 2017-07-14 2022-05-17 Novvi Llc Base oils and methods of making the same
US11473028B2 (en) 2017-07-14 2022-10-18 Novvi Llc Base oils and methods of making the same

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