EP0420931A1 - Lubrifiants synthetiques contenant des groupes polaires - Google Patents

Lubrifiants synthetiques contenant des groupes polaires

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Publication number
EP0420931A1
EP0420931A1 EP89907958A EP89907958A EP0420931A1 EP 0420931 A1 EP0420931 A1 EP 0420931A1 EP 89907958 A EP89907958 A EP 89907958A EP 89907958 A EP89907958 A EP 89907958A EP 0420931 A1 EP0420931 A1 EP 0420931A1
Authority
EP
European Patent Office
Prior art keywords
lubricating fluid
olefin
alkyl
adduct
enophile
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP89907958A
Other languages
German (de)
English (en)
Inventor
Catherine Shuihua Hsia Chen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mobil Oil AS
ExxonMobil Oil Corp
Original Assignee
Mobil Oil AS
Mobil Oil Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mobil Oil AS, Mobil Oil Corp filed Critical Mobil Oil AS
Publication of EP0420931A1 publication Critical patent/EP0420931A1/fr
Withdrawn legal-status Critical Current

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    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/22—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/24—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol, aldehyde, ketonic, ether, ketal or acetal radical
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    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
    • C10M107/10—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation containing aliphatic monomer having more than 4 carbon atoms
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    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/22—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
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    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/024—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
    • C10M2217/0245—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/026—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrile group
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/026—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrile group
    • C10M2217/0265—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrile group 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
    • C10M2217/0285—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound

Definitions

  • This invention relates to novel compositions useful as lubricants having polar functional groups.
  • the invention relates to novel lubricant compositions and methods for their preparation from lubricant range olefins and enophiles.
  • the formulation of lubricants typically includes an additive package incorporating a variety of chemicals to improve or protect lubricant properties in application specific situations, particularly internal combustion engine and machinery applications.
  • the more commonly used additives include oxidation inhibitors, rust inhibitors, antiwear agents, pour point depressants, detergent-dispersants, viscosity index (VI) improvers, foam inhibitors and the like.
  • This aspect of the lubricant arts is specifically described in Kirk-Othmer "Encyclopedia of Chemical Technology", 3rd edition, Vol. 14, pp477-526.
  • Lubricants particularly synthetic lubricants of the type of interest in the instant invention, are usually hydrogenated olefins. Due to their hydrocarbon structure they are largely incompatible with polar additives such as antioxidants, antirust and antiwear agents,etc. Accordingly, in order to render the lubricants compatible with the polar additives large amounts of expensive polar organic esters must be added to the formulation.
  • Useful commercial formulations may contain 20% percent or more of such esters as bis-tridecanol adipate for example, solely to provide a fully homogeneous lubricant blend of lubricant and additive.
  • the vulnerability of solubilizing agents to oxidative degradation promoting the formation of tars and gums must be taken into account. Seal swelling properties may be changed. Seal swell measures the ability of a lubricant to swell a seal, thus enhancing its sealing function.
  • Solubilizing agents may effect viscometric properties such as viscosity and viscosity index of the material. When materials deficient in these properties are added in large amounts, the lubricant's effectiveness will be impaired. In view of these complications it is evident that novel approaches are called for in the modification or formulation of lubricants to incorporate additives without compromising properties or adding significantly to the cost of the product.
  • Lubricants in particular synthetic lubricants, are known to contain olefinic unsaturation and it has been determined in the present invention that such unsaturation can be effectively utilized to react with polar groups to add a polar functionality on to the lubricant molecule.
  • the added polar group in the lubricant has sufficient solubilizing character to adequately dissolve additive packages without the addition of solubilizing agents such as adipate esters. It has been discovered in the instant invention that the necessary functionality i.e., functional group, can be added to the lubricant by reacting the lubricant olefinic group with an electronegative enophile.
  • unsaturated C 20 + lubricant range hydrocarbons containing an allylic hydrogen will react thermally or catalytically by addition to an alkene which contains olefinic unsaturation in the alpha,beta position to an electronegative group when the C 20 + unsaturated lubricant has the following structure comprising one or more allylic hydrogens:
  • R 1 , R 2 , R 3 , R 4 and R 5 may be hydrogen,alkyl or alkenyl and at least 17 carbon atoms in total.
  • alpha, beta unsaturated alkenes useful in the present invention include all those having the structure:
  • R 6 , R 7 , R 8 and R 9 are electronegative groups and the remainder hydrogen,alkyl, alkenyl, alkynalkyl, aryl or aralkyl.
  • a polar lubricant liquid which liquid includes the adduct of the above unsaturated lubricant and unsaturated alkene and having the structure:
  • R 8 or R 9 is an electronegative group and the remainder R 6 , R 7 , R 8 and R 9 is an electronegative group or hydrogen, alkyl, alkenyl, alkynalkyl, aryl or aralkyl and R 1 , R 2 , R 3 , R 4 and R 5 is hydrogen, alkyl or alkenyl at least one of which is C 17 + alkyl or alkenyl group.
  • unsaturated C 20 + lubricant molecule contains multiple allylic groups more than one mole of enophile will react with the lubricant to form an adduct containing more than one electronegative group or multiple polar sites. According to the invention, hydrogenation of the olefinic bonds of the adduct yields a polar lubricant with dispersant properties.
  • the formation of the adduct between C 20 + olefinic lubricant and an enophile is accomplished in the present invention by heating the mixture at elevated or by reaction catalyzed by a Lewis acid such as BF3 or A1Cl 3 .
  • the olefinic lubricants useful in the present invention in the formation of adducts with enophiles include unsaturated lubricants having 20 to 5000 carbon atoms where one or more of the unsaturated groups is allylic unsaturation. These include natural lubricants from mineral oil as well as synthetic lubricants containing twenty to five thousand carbon atoms. To be useful in the present invention all such lubricant molecules must contain one or more olefinic group of the following structure:
  • R 1 , R 2 ,R 3 , R 4 and R 5 may be hydrogen, alkyl or alkenyl and at least 17 carbon atoms in total for the sum of carbon atoms in R 1 , R 2 ,R 3 , R 4 and R 5 .
  • the olefinic bond may be in the alpha position, i.e., a vinyl structure where R 1 , and R 2 are hydrogen, or the bond may be an internal olefin where R 1 , R 2 , R 3 , R 4 and/or R 5 is an aliphatic hydrocarbon.
  • lubricants comprise a mixture of molecules usually having a wide range of molecular weights certain molecules may contain more than one olefinic bond, including alpha olefins and internal olefins of allylic structures. It is to be expected then that certain lubricant molecules may be produced according to this invention containing multiple adducts with specific enophiles, following reaction at multiple olefinic sites in the unsaturated lubricant molecule. Methods well known in the lubricant art are employed to produce the unsaturated lubricants required as feedstock in the instant invention.
  • the separation of mineral oil provides C 20 + lubricant basestock having native olefinic unsaturation, or other petroleum fractions may be cracked or dehydrogenated to provide a C 20 + lubricant basestock containing olefinic unsaturation.
  • feedstock in the present invention are the synthetic lubricants, especially those derived from C 3 + olefins or polyalphaolefins.
  • PAO polyalphaolefins
  • the PAO's are prepared by the polymerization of C 6 -C 20 1-alkenes such as 1-decene using typically Lewis acid catalyst such as BF 3 , aluminum chloride or Ziegler- Natta catalysts. Their preparation and properties are described by J. Brennan in Ind. Eng. Chem. Prod. Res. Dev. 1980, 19, pp 2-6. PAO incorporating improved lubricant properties are also described by J. A. Brennan in U.S. Patents 3,382,291, 3,742,082, and 3,769,363, and also in U.S.
  • C 3 -C 5 olefins are oligomerized in contact with an acidic, medium pore, shape selective metallosilicate catalyst such as aluminosilicate.
  • the aluminosilicate catalyst may have its surface dectivated by a surface deactivating agent such as a bulky amine or phosphine.
  • the PAO contains olefinic unsaturation reactive with enophiles.
  • HVI-PAO PAO lubricant compositions, herein referred to as HVI-PAO, exhibiting surprisingly high viscosity indices has been obtained.
  • HVI-PAO lubricants are particularly characterized by low ratio of methyl to methylene groups, i.e., low branch ratios, as further described hereinafter and low pour points below -15°C.
  • HVI-PAO lubricant basestock typically with a viscosity of 3 to 500 mm 2 /s at 100oC and a very high VI greater than 130, are produced from alphaolefins, 1-alkenes, of C 6 to C 20 , either alone or in mixture, over an activated chromium of reduced valence state catalyst supported on silica.
  • the HVI-PAO is further characterized by having a branch ratio of less than 0.19.
  • both PAO and HVI/PAO contain olefinic unsaturation and may be used in the instant invention.
  • branch ratios referred to are defined as the ratios of CH 3 groups to CH 2 groups in the lube oil and are calculated from the weight fractions of methyl groups obtained by infrared methods, published in Analytical Chemistry, Vol. 25, No. 10, p. 1466 (1953).
  • Branch ratio wt fraction of methyl group
  • HVI-PAO The preparation of HVI-PAO is described in the following examples but utilized in the instant invention without the hydrogenation of the oligomerization product:
  • a commercial Cr on silica catalyst which contains 1% Cr on a large pore volume synthetic silica gel is used.
  • the catalyst is first calcined with air at 700°C for 16 hours and reduced with CO at 350 °C for one to two hours.
  • 1.0 part by weight of the activated catalyst is added to 1-decene of 200 parts by weight in a suitable reactor and heated to 185 °C.
  • 1-Decene is continuously fed to the reactor at 2-3.5 parts/minute and 0.5 parts by weight of catalyst is added for every 100 parts of 1-decene feed.
  • the slurry is stirred for 8 hours.
  • the catalyst is filtered and light product boiled below 150 °C at 13 Pa (0.1mm Hg) is stripped.
  • the residual product is hydrogenated with a Ni on Kieselguhr catalyst at 200 °C.
  • the finished product has a viscosity at 100 °C of 18.5 mm 2 /s, VI 165 and pour point of -55 °C.
  • reaction temperature is 185 °C.
  • the finished product has a viscosity at 100°C of 145 mm 2 /s, VI of 214, and a pour point of -40°C.
  • reaction temperature is 100 °C.
  • the finished product has a viscosity at 100°C of 298 mm 2 /s, VI of 246 and a pour point of -32°C.
  • Unsaturated lubricants containing allylic groups obtained from the oligomerization of lower olefins such as C 3 -C 6 olefins in contact with an acidic, shape selective metallosilicate catalyst, such as ZSM-5, are also useful in the present invention. These lubricants generally have a viscosity between 2 and 12mm 2 /s at 100oC.
  • U.S. Patent 4,568,786 describes the oligomerization of propylene to produce a low molecular weight lube olefin which can be reacted according to the present invention to provide the novel adduct disclosed.
  • Other zeolite catalyzed processes producing olefinic lubes useful in the present invention are described in the following U.S.Patents 4,520,221, 4,658,786 both to C.S.H.Chen.
  • alpha,beta unsaturated alkenes useful in the present invention include all those having the structure:
  • R 6 , R 7 , R 8 and R 9 are electronegative groups and the remaining groups are hydrogen, alkyl, alkenyl, aryl or aralkyl.
  • electronegative groups useful in the enophiles of structure (II) include:
  • A is 0, NH, NR where R is alkyl ; -C-Z where Z is H, OH,
  • Enophiles of particular use in the instant invention include maleic anhydride, maleimide, acrylonitrile, styrene, 4-carboethoxy styrene, ethylacrylate, acrylamide, acrolein, methyl vinyl ketone, phenyl vinyl ketone, cinnamyl chloride,
  • novel lubricants of the present invention are prepared according to the well-known “Ene” reaction by reacting the unsaturated lubricants and enophiles described above thermally or in contact with a catalyst to form the unsaturated adduct.
  • the “Ene” reaction is described in "Accounts of Chemical Research",
  • the adduct (III) and the polar saturated lubricant (IV) have the structure:
  • R, through Rr may be hydrogen, alkyl or alkenyl and the sum of carbon atoms in all R 1 through R5 groups totals at least 17, where at least one of R 8 , R 9 is an electronegative group with the remaining groups of R 6 through R 9 being an electronegative group or hydrogen, alkyl, alkenyl, alkynalkyl, aryl or aralkyl.
  • the Ene reaction will produce an adduct containing multiple enophile moieties comprising lubricant molecules of particularly enhanced polarity.
  • the Ene reaction adduct formation between unsaturated lubricant molecules and enophiles may be conducted thermally at temperatures between 100°C and 400°C either neat or in a solvent.
  • the process may be conducted as a batch process or continuous.
  • Lewis acid catalysts are preferred such as BF 3 , AlCl 3 , (CH 3 ) 2 A1Cl, SnCl 4 , C 2 H 5 A1C1 2 and the like.
  • the scope of the present invention includes the further reaction of the polar function of the hydrogenated adducts prepared by the process of the invention to provide further useful products, typically enhancing the properties of the lubricant.
  • the nitrile function of adducts prepared from acrylonitrile may be hydrolyzed to acid or amide or esterified by methods well known in the art.
  • Hydrogenation of the adduct formed between an unsaturated lubricant and maleic anhydride produces the substituted succinic anhydride which may be further reacted with alcohol by known means to yield a diester of the structure (V) from the anhydride (VI):
  • R in (V) and (VI) is hydrogen, alkyl or alkenyl and the total number of carbon atoms in all R groups is at least 17 and, preferably, with at least one R group a lubricant moiety of between
  • R 1 of (V) is C 1 -C 30 alkyl such as methyl, ethyl, 2-hydroxyethyl, propyl, octyl, lauryl and the like.
  • the mixture is heated with stirring to 175 °C whereby the pressure increased to 793 kPa (100 psig) and kept at this temperature for 14 days.
  • Samples are taken periodically during the reaction and analyzed by GC, FTIR, and proton NMR for the overall boiling range and structural changes of the reaction mixture.
  • the GC results show a progressive decrease with time in the relative amounts of maleic anhydride and C 3 0 and a corresponding increase in the amounts of higher boiling materials.
  • Both the FTIR results and the proton NMR results showed progressive reaction between the olefins and maleic anhydride forming the corresponding succinic anhydride adducts.
  • analytical results showed that no significant change took place after 9 days.
  • 227g of the succinic anhydride adducts obtained in Example 4 is hydrogenated at 140°C over a nickel catalyst (Harshaw 5132-P) in a Parr reactor until no more hydrogen is taken up. After filtering off the nickel catalyst, the hydrogenated succinic anhydride adducts are refluxed overnight in excess ethanol over HZSM-5B catalyst as the esterification catalyst. After removing the catalyst and excess ethanol, the product is identified as diethyl succinic esters by IR and is shown to be soluble in a variety of polar organic compounds.
  • the “Ene” reaction was carried out between 305g of the C 3 0 -C 4 0 mixture and 48g of maleic anhydride as described in Example 4, except that the reaction temperature is raised to 190°C. The reaction is essentially complete in 5 days.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

On a mis au point un nouveau fluide lubrifiant polaire comprenant le produit de la réaction d'un énopile et d'hydrocarbure oléfinique C20+ contenant des groupes allyliques. Le produit de la réaction hydrogénée polaire présente d'excellentes propriétés lubrifiantes et la capacité de former des mélanges homogènes avec des additifs. Le produit d'addition est formé par addition thermiquement induite d'énophile à de l'oléfine ou par addition catalysée d'acide Lewis.
EP89907958A 1988-06-23 1989-06-21 Lubrifiants synthetiques contenant des groupes polaires Withdrawn EP0420931A1 (fr)

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US21045288A 1988-06-23 1988-06-23
US210452 1988-06-23

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US5427703A (en) * 1992-07-17 1995-06-27 Shell Oil Company Process for the preparation of polar lubricating base oils

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US3215707A (en) * 1960-06-07 1965-11-02 Lubrizol Corp Lubricant
NL280822A (fr) * 1961-07-11
FR1337544A (fr) * 1961-08-30 1963-09-13 Lubrizol Corp Compositions de fluides hydrauliques
US3412111A (en) * 1965-06-02 1968-11-19 Gulf Research Development Co Process for reacting an olefin with maleic anhydride to obtain an alkenyl succinic anhydride
GB1398000A (en) * 1972-10-20 1975-06-18 Mobil Oil Corp Preparation of alkenyl-succinic anhydrides
GB1483729A (en) * 1973-09-13 1977-08-24 Shell Int Research Process for the preparation of an alkylsuccinic acid or the anhydride thereof
US4396774A (en) * 1982-03-22 1983-08-02 Standard Oil Company (Indiana) Use of a catalyst to inhibit formation of tar during the "ENE" reaction of an ethylenically unsaturated alpha, beta dicarboxylic acid compound and an ethylenically unsaturated hydrocarbon
US4568786A (en) * 1984-04-09 1986-02-04 Mobil Oil Corporation Production of lubricant range hydrocarbons from light olefins

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