US3149178A - Polymerized olefin synthetic lubricants - Google Patents

Polymerized olefin synthetic lubricants Download PDF

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Publication number
US3149178A
US3149178A US123126A US12312661A US3149178A US 3149178 A US3149178 A US 3149178A US 123126 A US123126 A US 123126A US 12312661 A US12312661 A US 12312661A US 3149178 A US3149178 A US 3149178A
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Prior art keywords
oil
dimer
hydrogenated
decene
polymer
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Lyle A Hamilton
Francis M Seger
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ExxonMobil Oil Corp
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Socony Mobil Oil Co Inc
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Priority to NL135909D priority Critical patent/NL135909C/xx
Priority to BE620076D priority patent/BE620076A/xx
Priority to NL280822D priority patent/NL280822A/xx
Priority to US123126A priority patent/US3149178A/en
Application filed by Socony Mobil Oil Co Inc filed Critical Socony Mobil Oil Co Inc
Priority to DE19621468587 priority patent/DE1468587A1/de
Priority to FR903468A priority patent/FR1332257A/fr
Priority to DK309762AA priority patent/DK119322B/da
Priority to GB26655/62A priority patent/GB1011471A/en
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Publication of US3149178A publication Critical patent/US3149178A/en
Priority to FR989500A priority patent/FR88752E/fr
Priority to FR113362A priority patent/FR93371E/fr
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G50/00—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation
    • C10G50/02—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation of hydrocarbon oils for lubricating purposes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G69/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process
    • C10G69/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only
    • C10G69/12—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only including at least one polymerisation or alkylation step
    • C10G69/126—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only including at least one polymerisation or alkylation step polymerisation, e.g. oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/10—Lubricating oil
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • 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
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/066—Arylene diamines
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
    • C10M2219/066—Thiocarbamic type compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • 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
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines

Definitions

  • the lubricant must have a relatively low pour point and a high viscosity index. It must also be responsive to chemical inhibitors and stabilizers.
  • Another object of this invention is to provide improved, novel synthetic lubricants.
  • Another object is to provide hydrogenated, polymerized olefin synthetic lubricants of increased inhibitor response, high Viscosity Index (V.I.), and low pour point.
  • a further object is to provide new hydrogenated, polymerized olefin synthetic lubricants that are thermally stable.
  • a specific object is to provide hydrogenated synthetic lubricants produced from polymerized alpha monoolefins that have low pour points and high V.I.
  • Another specific object is to provide new hydrogenated synthetic lubricants produced from polymerized alpha monoolefins that have been treated to render them thermally stable.
  • a further spe cific object is to provide simple methods for producing the synthetic lubricants of this invention.
  • this invention provides a novel synthetic lubricant having low pour point, high V.I., and good additive response and the method for producing it, which comprises distilling a polymerized normal alpha-monoolefin synthetic lubricant, thereby obtaining a fraction containing dimer and a residual fraction essentially free from dimer; and completely saturating said residual fraction by hydrogenation.
  • the invention further provides a novel thermally stable synthetic lubricant and a method for producing it that comprises distilling a polymerized normal alpha-monoolefin synthetic lubricant, thereby obtaining a fraction containing dimer and a residual fraction essentially free from dimer; completely saturating said residual fraction by hydrogenation; and heating the thus-saturated residual fraction at a temperature varying between about 600 F. and about 700 F., for a period of time varying inversely between about 1 and about 10 hours, with 650 F. for 3 hours being preferred.
  • this invention provides a thermally stable synthetic lubricant and a method for producing it, that comprises distilling a polymerized normal alpha-monoolefin synthetic lubricant, thereby obtaining a fraction containing dimer and a residual fraction essentially free from dimer; heating said residual fraction at a temperature varying between about 600 F. and about 700 F., for a period of time varying inversely between about 1 and about 10 hours; and completely saturating the thus-heated residual fraction by hydrogenation.
  • polymerized normal alpha-monoolefin synthetic lubricant means synthetic lubricants made by polymerizing normal alpha-monoolefins (C to C either thermally or catalytically in the presence of a di-tertiary alkyl peroxide or of a Friedel-Crafts catalyst, including boron tri-fiuoride and aluminum chloride, under mild conditions.
  • C to C normal alpha-monoolefins
  • a Friedel-Crafts catalyst including boron tri-fiuoride and aluminum chloride, under mild conditions.
  • the term excludes polymers produced in the presence of other peroxides, such as diacyl peroxides, which polymers contain structural elements of the peroxy catalyst.
  • the selection of the normal alphamonoolefin monomer is important.
  • the best, and particularly preferred monomer is l-decene.
  • the l-decene can be relatively pure monomer or an olefin or hydrocarbon mixture rich in l-decene. It has also been found, however, that mixtures of normal alpha-monoolefins having between about 6 and about 12 carbon atoms can be used, provided that the mean value of the olefin chain length is about 10 carbon atoms.
  • a mixture of equal parts of l-hexene, 1- octene, l-decene, and l-dodecene produced a satisfactory lubricant in accordance with this invention.
  • the thermally polymerized olefins utilizable herein are described in United States Letters Patent No. 2,500,166.
  • the polymerization is carried out generally at temperatures varying between about 500 F. and about 750 F. for periods of time varying between about 20 hours and about one hour.
  • the polymerization is carried out at temperatures varying between about 600 F. and about 700 F.; the optimum reaction times at the maximum and the minimum reaction temperatures being specified in the respective patent specifications.
  • the olefin reactants are normal alphamonoolefins having between 6 carbon atoms and 12 carbon atoms per molecule.
  • the utilizable olefins are, for example, l-hexene, l-octene, l-nonene, l-decene, and 1- dodecene.
  • the olefin reactant can be substantially pure normal alpha-monoolefins, mixtures of olefins and/or ens-9,1
  • ly-available and especially preferred catalyst is di-tertiary butyl peroxide.
  • the amount of peroxide catalyst used is bteween about 0.01 and about 0.3 mole per mole of normal alpha-monoolefin reactant.
  • the temperature employed is the activation temperature of the peroxide catalyst and varies between about 100 C. (212 F.) and about 200 C. (392 F.). In general, the time of reaction varies between about one hour and about 6 hours.
  • Polymerized normal alpha-monoolefin oils utilizable in the present invention can readily be prepared in the presence of Friedel-Crafts catalysts, under relatively mild conditions. As is well known to those skilled in the art, severe operating conditions, particularly with. some promoted Friedel-Crafts catalysts, induce undeshable side reactions, isomerization, resinificaticn, etc. It is further rec- .ognized that all Friedel-Crafts catalysts are not entirely equivalent in the type of oils produced. To a great extent, the choice of catalyst and of reaction conditions can be made in order to produce polymer lubricants of a desired. viscosity. 7
  • EXAMPLE 2 The polymer oil product of Example 1 was hydrogenated to saturate the olefinic double bonds. genation was carried out by conventional procedures using an Aminco rocking bomb with nickel-on-kieselguhr catalyst (20 g. per g; of. oil). Initial hydrogen pressure was 1500 p.s.i.g. Temperature was held at 300 F. for
  • EXAMPLE 3 Portions of the synthetic lubricants defined in Examples 1 and 2 were blended with known oxidation inhibitors. Each blend was subjected to the Laboratory Oxidation Test (B-IOA). Pertinent data on blends and test results are set forth in Table II.
  • test oil is placed in a 200 x 25 mm, test tube, together with 15.6 sq. in. sandblasted iron wire, 0.78 sq. in. polished copper Wire, 0.87 sq. in. polished aluminum wire and 0.167 sq. in. polished lead surface.
  • the tube is maintained at 325 F. in an aluminum block bath. Dry air is bubbled through the test oil for 24 hours, at a rate of 10 liters per hour.
  • Table II Oil of Example 1 Oil of Example 2 Additives Percent Percent V N.N. 1s. Lead N.N. Vis. Lead Incr. Change, Sludge Loss, Incr. Change, Sludge Loss,
  • Inhibitor 162 (du Pont) is a mixture of monoand di-lorol (C esters of orthophosphoric acid.
  • Acryloid 7-94 is a polymethacrylate V.I. irnprover.
  • OD. 561 is cadmium diamyldithiocarbamate.
  • Agerite Hi Par is a mixture of phenyl-beta-naphthylamine, isopropoxydiphenylamine, and diphenyl paraphenylenediamine.
  • Tricosyl P.A.N. is tricosyl phenyl-alphanaphthylamine.
  • the additive formulations shown are typical of lubricating oil formulations.
  • a hydrogenated synthetic lubricant of low pour point is obtained by removing, by distillation, a fraction of the polymerized normal alphamonoolefin synthetic lubricant containing the dimer. The residue thus obtained is then hydrogenated to saturate olefinic double bonds. The dimer out can be recycled to the polymerization step, dong with fresh monomer feed.
  • the same results can be obtained by first hydrogenating the polymerized olefin synthetic lubricant and then removing the dimer. This me hod, however, is less desirable, because the dimer is now saturated, in this case, and is not available for recycling to the polymerization step. Thus, if there is no use for the saturated dimer, it is a loss to the process.
  • EXAMPLE 4 Using the procedure described in Example 1, 3100 grams (22.14 moles) of l-decene were polymerized using 160 grams (1.10 moles) of di-tertiary-butyl peroxide catalyst. The polymerization was carried out at 150 C. for 5 hours. Unreacted l-decene was removed by distillation. The properties of the polymer oil thus obtained (designated Raw Polymer Oil) are essentially those of Example 1.
  • This polymer oil was subjected to distillation to remove a cut (consisting chiefly of dimer) boiling up to 180 C. under 1 mm. mercury pressure.
  • the residual oil (designated Topped Polymer Oil) had the properties set forth in Table III.
  • the topped polymer oil was saturated by hydrogenation in contact with nickel catalyst.
  • the conditions used were the same as those of Example 2.
  • the product (designated Hydrogenated Topped Polymer Oil) had the properties set forth in Table III.
  • the dimer can be removed either before or after hydrogenation. This point is illustrated by the following example.
  • EXAMPLE 5 A thermal polymer oil was prepared by heating 1337 grams (9.55 moles) of l-decene at a temperature of about 650 F. for 10 hours at maximum pressure p.s.i.g. The product was topped to remove Unreacted l-decene, leaving a polymer oil. This oil was then subjected to distillation at about C. under 3 mm. mercury pressure to remove the decene dimer. The residue (designated Polymer Oil Less Dimer) had the properties set forth in Table IV.
  • This dimer-free polymer oil was hydrogenated over nickel catalyst under the usual conditions described in Example 2.
  • the resultant oil (Dimenfree Hydrogenated Polymer Oil) had the properties set forth in Table IV.
  • the hydrogenated polymer oil was further distilled up to a vapor temperature of 230 C. at l nun. mercury pressure, in order to remove decene dimer.
  • the residual oil (Residual Hydrogenated Polymer Oil) had the properties set forth in Table IV.
  • a reaction vessel was charged with 3000 g. l-decene and placed in a cooling bath. A total of 26 g. AlCl was added in small increments over a period of 95 minutes. During this period of time the temperature of the reaction mixture was 203-6 C. Then, the reaction mixture was filtered to remove solid catalyst. The filtrate was blown with ammonia gas to remove dissolved aluminum compounds and filtered. The blowing operation was repeated. The final filtrate was topped to remove unreacted monomer and subjected to distillation up to 132 C. at 0.5 millimeter mercury pressure to remove dimer. The remaining, residual polymer oil had the properties set forth in Table V.
  • EXAMPLE 7 A reaction vessel was charged with 300 g. of l-decene and 3 g. AlCl were added in one portion. The temperature of the reaction mixture rose from 26" C. to C. in four minutes. A water bath was applied to the reaction vessel to remove heat. After 40 minutes, the temperature was 80 C. The reactants were maintained at 80 C. for one hour. The raw product Was filtered to remove solid catalyst. The filtrate was Washed first with aqueous sodium hydroxide (5%) and then with '2 water and filtered. The product was topped to remove unreacted monomer and then dimer was removed by distilling to a temperature up to 210 C.,under l millimeter mercury pressure. The remaining polymer oil had the properties set forth in Table V.
  • EXAMPLE 8 ing polymer oil was further fractionated into a, fraction boiling at 200-222" C. at l millimeter mercury pressure.
  • the trimer is an excellent synthetic lubricant, as Well as the residual oil product.
  • the properties of the trimer cut and of the residual oil are set forth in Table V.
  • EXAMPLE 9 This example illustrates the preparation of polymer oil from a mixture of l-olefins averaging 10 carbon atoms.
  • a reaction vessel Into a reaction vessel .was placed a charge containing, by weight, 25 percent l-hexene, 25 percent l-octene, 25 percent l-decene, and 25 percent l-dodecene. Over a period of 3 hours 1.4 weight percent of a decanol-BF complex was added in two portions. The reaction temperature was between 5 C. and 29 C. The product was washed and filtered. Then, it was topped to remove monomer and distilled up to 190 C.
  • Example N 6 7 8 9 Product Resid- Resid- Trimer Resid- Trimer Residual ual ual ual K.V. at 210 F., S1. 85 11.86 3.69 G. 83 2. 7 6.40 K.V. at 100 F., cs 290. 8 84. 84 16. 22 42. 30- 11.06 37. 93 V.I 126 128 131 125 102 127 Four Point, F- 55 -65 EXAMPLE 10 A polymer oil, prepared as described in Example 7, was hydrogenated using the procedure of Example 2. Pertinent properties of the hydrogenated polymer oil are set'forth in Table VI.
  • EXAMPLE 11 A composite of trimer and residual. polymer oil, prepared as in Example 8, was hydrogenated using the method of Example 2. Pertinent properties of the hydrogenated polymer oil are set forth in Table VI.
  • EXAMPLE 12 The combined polymer oil of Example 9 was hydrogenated using the procedure described in Example 2. Pertinent properties of the hydrogenated polymer oil are set forth in Table VI. a V i It has been mentioned hereinbefore that the synthetic lubricants produced herein are novel materials. These lubricants possess a plurality of properties not heretofor found in conventional mineral lubricating oils. For the ti? sake of comparison, included in Table VI are properties of two typical mineral lubricating oils. -Eoth oils were prepared from petroleum lube oil stocks by conventional solvent extraction, dewaxing, and percolation methods Oil A is from a paratfinic base stock. Oil B is from a naphthenic (Coastal) base stock.
  • the residual hydrogenated polymer oil products are excellent lubricants for many purposes. They also have excellent response to inhibitors. tionedhereinbefore, however, the requirements of high temperature jet engine lubrication are very severe. In such an application, the aforedescribed synthetic polymer oils are not sufliciently stable. In another embodiment of this invention the hydrogenated residual polymer oils can be rendered stable to high temperature operation by means of a simple thermal treatment.
  • the thermal treatment is carried out by heating the polymer oil at temperatures varying between about 600 F. and about 700 F. for a period of time varying inversely between about 1 hour and about 10 hours.
  • Preferred conditions are treatment at 650 F. for 3 hours.
  • the polymer oil is agitated under nitrogen atmosphere during the thermal treatment. It has been found that the thermal treatment operation can be carried out of any point during the preparation of the final, heatstable synthetic polymer lubricant. Thus, for example, the following sequences of steps will produce stable lubricants:
  • EXAMPLE 13 A raw olefinic polymer oil was prepared from l-decene, as described in Example 1. It was topped to remove dimer. The residual oil was then hydrogenated under the usual conditions (400 F, etc.). This material (Oil A) had the properties set forthin Table VII. A different lot of decene polymer oil was made in the manner of Oil A. It was then thermally treated by heating at about 645 F. for about 3 hours. Gas evolution occurred, agitating the liquid. The resultant oil (Oil B) had the properties given in Table VII. [This oil had been freed of volatile components 'by atmospheric-l-vacuum topp gs As men- Pour Point. F Flash test, Fire test, F Gr. API
  • EXAMPLE 14 A decene trimer oil, produced as in Example 8, was thermally treated by heating at about 650 F. for about 3 hours. The thus-treated oil was hydrogenated using the procedure described in Example 2. Pertinent properties of the hydrogenated treated oil are set forth in Table VH1.
  • EXAMPLE 15 A decene residual polymer oil, produced as in Example 8, was thermally treated by heating at about 650 F. for about 3 hours. The thus-treated oil was hydrogenated using the procedure described in Example 2. Pertinent properties of the hydrogenated treated oil are set forth in Table VIII.
  • EXAMPLE 16 A decene polymer oil, produced as in Example 6, was thermally treated by heating at about 650 F. for about 3 hours. The thus-treated oil was hydrogenated using the procedure described in Example 2. Pertinent properties of the hydrogenated treated oil are set forth in Table VIII.
  • thermal stability of lubricants utilizable in high temperature jet engine lubrication is determined in various ways. Several tentative methods have been employed. One consists of a cyclic exposure to heat as the oil is pumped over a spinning disc at elevated temperature.
  • Room temperature was kept constant by air conditioning to avoid pressure changes from room temperature changes.
  • the spinning disc is rotated at 2500 rpm.
  • the temperature of the disc is held at 525 F.
  • oil is passed over the disc in a thin film, exposed to the high temperature. If the oil is degraded thermally a pressure rise in the manometer system will occur from the gases formed.
  • Oil Pressure rise, mm./hr. Oil A 72 Oil B 2 From the data in Example 17, it will be apparent that extremely heat stable lubricants have been produced by this embodiment of the invention.
  • a process for producing a synthetic lubricant that comprises distilling a liquid polymerized normal alphamonoolefin synthetic lubricant, thereby obtaining a fraction containing dimer and a residual fraction essentially free from dimer, and completely saturating said residual fraction by hydrogenation under catalytic hydrogenation conditions; said normal alpha-monooletin having between about 6 carbon atoms and about 12 carbon atoms and having a mean chain length of about 10 carbon atoms.
  • a process for producing a synthetic lubricant that comprises distilling a liquid polymerized normal alphamonoolefin synthetic lubricant, thereby obtaining a fraction containing dimer and a residual fraction essentially free from dimer, completely saturating said residual fraction by hydrogenation under catalytic hydrogenation conditions, and heating the thus-saturated residual fraction at a temperature varying between about 600 F. and about 700 F., for a period of time varying inversely between about 1 hour and about 10 hours; said normal alphamonoolefin having between about 6 carbon atoms and about 12 carbon atoms and having a mean chain length of about 10 carbon atoms.
  • a process for producing a synthetic lubricant that comprises distilling a liquid polymerized normal alphamonoolefin synthetic lubricant, thereby obtaining a fraction containing dimer and a residual fraction essentially free from dimer, heating said residual fraction at a temperature varying between about 600 F. and about 700 F., for a period of time varying inversely between about 1 hour and about 10 hours, and completely saturating the thus-heated residual fraction by hydrogenation under catalytic hydrogenation conditions; said normal alphamonoolefin having between about 6 carbon atoms and about 12 carbon atoms and having a mean chain length of about 10 carbon atoms.

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US123126A US3149178A (en) 1961-07-11 1961-07-11 Polymerized olefin synthetic lubricants
DE19621468587 DE1468587A1 (de) 1961-07-11 1962-07-10 Verfahren zur Herstellung eines synthetischen Schmiermittels
FR903468A FR1332257A (fr) 1961-07-11 1962-07-10 Lubrifiants synthétiques à base d'oléfines polymérisées
DK309762AA DK119322B (da) 1961-07-11 1962-07-11 Fremgangsmåde til forbedring af egenskaberne af polymeriserede normale α-monoolefin smøremidler.
GB26655/62A GB1011471A (en) 1961-07-11 1962-07-11 Polymerized olefin synthetic lubricants
FR989500A FR88752E (es) 1961-07-11 1964-09-26
FR113362A FR93371E (fr) 1961-07-11 1967-07-06 Lubrifiants synthétiques a base d'oléfines polymérisées.

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FR1332257A (fr) 1963-07-12
GB1011471A (en) 1965-12-01
BE620076A (es)
DE1468587A1 (de) 1970-04-16
NL135909C (es)

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