US3012963A - Hydrogenation of lubricating oils to remove sulfur and saturate aromatics - Google Patents

Hydrogenation of lubricating oils to remove sulfur and saturate aromatics Download PDF

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US3012963A
US3012963A US791074A US79107459A US3012963A US 3012963 A US3012963 A US 3012963A US 791074 A US791074 A US 791074A US 79107459 A US79107459 A US 79107459A US 3012963 A US3012963 A US 3012963A
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oil
oils
hydrogenation
catalyst
nickel
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Raymond C Archibald
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Shell USA Inc
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Shell Oil Co
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Priority to NL125742D priority Critical patent/NL125742C/xx
Priority to NL248007D priority patent/NL248007A/xx
Application filed by Shell Oil Co filed Critical Shell Oil Co
Priority to US791074A priority patent/US3012963A/en
Priority to DE19601470615 priority patent/DE1470615A1/de
Priority to GB3669/60A priority patent/GB897240A/en
Priority to FR817317A priority patent/FR1246671A/fr
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
    • B01J27/04—Sulfides
    • B01J27/043—Sulfides with iron group metals or platinum group metals
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/104—Aromatic fractions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106—Naphthenic fractions
    • 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
    • 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 the hydrotreatment of lubricating oils. More particularly, it relates to the quality improvement of lubricating oils containing polycyclic aroma-tics.
  • the conventional refining of lubricating oils involves several steps, each of which is directed to the removal of certain undesirable components.
  • Some refining methods are chemical but most are merely physical separations of the undesirable components. Among these are distillation, adsorption, solvent extraction, crystallization and solvent precipitation.
  • sulfuric acid treatment ha v heretofore been the most common. All or merely part of these unit operations may be used in processing a given lllbIleating oil stock, depending upon the end use of the finished oil.
  • Residual lubricating oils are usually deasphalted by means of solvent precipitation.
  • the lubricating oil to be deasphalted is mixed with a light liquefied paraffinic hydrocarbon, such as propane.
  • propane a light liquefied paraffinic hydrocarbon
  • the oil and any wax in it remain dissolved in the propane while the higher molecular Weight resins and asphalt are precipitated in the form of a viscous liquid, which is readily separated.
  • the oil from which the asphalt has been removed is then suitable for further treatment to produce residual lubricating oils, i.e., bright stocks.
  • lubricating oil stocks contain wax, which if left in the oil, would interfere with the flow of the finished lubricant at low temperatures. Wax in the finished oil can therefore be tolerated only in low concentrations unless the oil is to be used only under conditions in which low temperatures are not encountered.
  • the most widely used process for dewaxing lubricating oil stocks is solvent dewaxing in which the waxy oil is diluted with a solvent having a low solvency for wax and a high solvency for oil. The mixture of solvent, wax, and oil is then chilled to bring about a phase separation, and the precipitated wax is removed by filtration. The pour point of the dewaxed oil is then determined by the extent to which the wax is removed.
  • Treatment with sulfuric acid may also be used to remove the same components as solvent extraction. Unlike the aforementioned processes which are purely physical separations, treatment with sulfuric acid is also chemical in nature in that part of the undesirable components are converted to insoluble sulfonates which are removed With the acid sludge. However, similarly to the purely physical separations, the undesriable components, whether chemically converted or not, are removed from the oil.
  • most lubricating oilsmust also be treated with clay to improve the clarity and color of the finished oil, and in some cases their oxidation stability.
  • the primary result of clay treatment is to remove suspended solids, Water droplets, and dissolved polar ingredients such as naphthenic acid, phenols, soaps, etc.
  • a very desirable method by which lubricating oil processing losses may be reduced is to convert the undesirable aromatic hydrocarbon components to more desirable napthenic hydrocarbon by means of hydrogenation. By this means, the processing loss during the viscosity-index improving step may be substantially reduced.
  • the hydrogenation of lubricating oils is, of course, well known; for example see Zuidema, The Performance of Lubricating Oils, Reinhold Publishing Company (1952, page 164).
  • hydrogenation of lubricating oils has been practiced only to a limited extent despite the fact it has long been known. This has been due in part to the relatively high cost of hydrogenation and in part to the lack of flexibility of prior hy'drotreating methods to obtain good quality lubricants from a wide range of lubricating oil stocks.
  • Nickel sulfide catalysts have long been well known as hydrogenation catalysts. Their use has been disclosed, inter alia, for the hydrogenation of cracked petroleum residues, phenols, and simple sulfur compounds, and for the cracking of waxes and other hydrocarbons. However, in a large degree because of their high hydrocracking activity under ordinary hydrotreating conditions, the use of nickel sulfides as hydrotreating catalysts has been restricted to mixtures thereof with other catalytically active metals, especially tungsten.
  • nickel sulfide may, under proper operating conditions and within a certain range of atomic ratios of nickel to sulfur, be used for the hydrogenation of lubricating oils without excessive hydrocracking.
  • unsulfided or slightly sulfided nickel catalyst there is very little selectivity for the conversion of polyarornatics to monoaromatics, i.e., complete saturation of the polyaromatics takes place to an excessive degree, and hydrocracking activity is excessive. Therefore, in order to attain the aforementioned selectivity, it is necessary that the ratio of nickel to sulfur be kept low.
  • the degree of sulfiding is too high, i.e., the degree of sulfiding is too high, i.e., the degree of sulfiding is too high, i.e., the degree of sulfiding is too high, i.e., the degree of sulfiding is too high, i.e., the degree of sulfiding is too high, i.e., the
  • nickel-sulfur ratio too low, the activity of the catalyst is impaired. From this, it is apparent that the degree of sulfiding has a pronounced effect on both the activity and selectivity of the catalyst. The reasons for this are not known with certainty. However, it is known that within the practicable operating limits of hydrogenation reactions, and in a hydrogen-hydrogen sulfide environment, the nickel catalyst may exist in the solid state in several stable forms. The following molecular formulae have been reported: NiS NiS, Ni S Ni S and Ni.
  • the Ni S form of the catalyst is the most active form to attain the desired selectivity for this invention. It is therefore preferred that the catalyst contain a major amount of nickel in the form of Ni S Since the presence of nickel in the Ni S form cannot be readily determined, it is necessary to maintain the degree of sulfiding within narrow limits. It has thus been found that the catalyst may be maintained at a satisfactory de 'gree of activity and selectivity if the average atomic ratio of nickel to sulfur is from about 1.3 to about 3.0. At these ratios, the amount of Ni S will generally not be lower than about 30%. However, to obtain both optimum activity and selectivity, it is preferred that the atomic ratio of nickel to sulfur be from about 1.4 to 1.8.
  • Nickel sulfides maybe prepared in a number of ways from finely divided metallic nickel. Nickel can be sulfided with hydrogen sulfide gas to form nickel sulfide and hydrogen.
  • the catalyst may be prepared by reacting carbon bisulfide with finely divided metallic nickel to form nickel sulfides and carbon.
  • a method of preparing the catalyst is the hydrogenation of finely divided higher nickel sulfides prepared as above to the Ni S form, in which case hydrogen sulfide gas is liberated.
  • the stable existence of a particular sulfide in a hydrogenation system such as that encountered in the instant process depends upon the temperature and the composition of the vaporous phase surrounding the sulfide.
  • the molecular state of the stable sulfide depends on the ratio of hydrogen sulfide to hydrogen.
  • the H szH molar ratio of the hydrogen-containing gas must be adjusted to at least about 0.0002 but not more than about 0.02 within the useful temperature range of the process.
  • the catalyst is stable in the Ni S form up to a temperature of about 850 F.
  • the temperature sh uld not be greater than about 800 F.
  • the lower temperature limit of the invention is governed largely by the desired reaction rate, which is related directly to the temperature of the process. Though a temperature as low as 600 F. may be used, at least 650 F. is preferred. From the standpoint of both hydrogenation rate and freedom from hydrocracking, a temperature of from about 650 to about 750 F. is preferred.
  • the invention can therefore be practiced at a pressure of from about 500 to 3,000 psi. or greater. It is preferred, however, to operate within the pressure range of from about 1,200 to 2,200 p.s.i.
  • LHSV liquid hourly space velocity
  • the hydrogen uptake of the treated oil is preferably from to about 500 standard cubic feet per barrel of liquid feed. It is important that the degree of hydrogenation not exceed about 500 s.c.f. per barrel hydrogen uptake since the treated oil may lose much of is lubricating properties. It is even further preferred that the hydrogen uptake of the treated oil not exceed 300 s.c.f. per barrel.
  • Both distillate and residual lubricating oil fractions may be processed according to the invention.
  • the treatment of lubricating oils is most advantageous, however, with respect to lubricant fractions containing a major proportion of polycyclic aromatics.
  • aromaticscontaining fractions are normally obtained from naphthenic-and intermediate base lubricating oil crudes having a U0? characterization factor of from about 11.0 to 12.1.
  • Typical of such crudes which are found in the United States are those from the Gulf Coastal Area, East Texas, West Texas, New Mexico, Mid Continent, and the Four Corners Area.
  • Certain polyaromatics-containing gas oils such as catalytically cracked cycle oil and heavy gas oils may also yield useful lubricant materials when processed according to the invention.
  • the lubricant stock to be treated by the process may be completely unrefined, partially refined, or even completely refined as defined by prior processing schemes. However, the greatest benefit is derived therefrom in the use of unrefined or only partiallymefined oils. In the case of residual lubricating oils,
  • the oil be deasphalted since the highly condensed asphaltic portions therein tend to deposit coke on the catalyst and tend also to promote excessive hydrocracking.
  • Deasphalted oil refers to an oil from which the asphalt and tars have been essentially completely removed.
  • Asphalt and tars as used here, are defined as in 3. Ph. Pfeiffer, The Properties of Asphaltic Bitumen (1950), page 5.
  • the asphaltic constituents are additionally detrimental in that they contain large amounts of metallic contaminants which poison the catalyst.
  • the oil need not be dewaxed or otherwise treated prior to the selective hydrogenation step of the invention.
  • Example I A propane-dewaxed (DW) naphthenic lubricating oil distillate (West Texas Ellenburger) having a viscosity of about 250 Saybolt Universal Seconds (S.U.S.) at 100 F. and is viscosity index [Dean and Davis, Chemical and Metallurgical Engineering, vol. 36, p. 618-9 (1929)] of 91 was selectively hydrogenated over a supported nickel sulfide catalyst having the average composition Ni S The catalyst was supported on alumina. The operating conditions of the hydrogenation reaction were 734 F. and 1500 p.s.i.g. pressure.
  • the oil feed was contacted with the catalyst at a space velocity (LHSV) of about 0.4, and a hydrogen-to-oil mole ratio of 30 to 1 was maintained throughout. Gas was continuously bled from the reaction system and fresh hydrogen added in order to maintain the molar ratio of H 8 to H at 0.001.
  • the VI of the hydrotreated oil was 104, and the net yield was 90% by weight.
  • the aromatics content of the treated and untreated oil were as follows:
  • Example II Another portion of the same dewaxed naphthenic lubricating oil distillate as was used in Example I was extracted in a conventional Duosol solvent extraction system, employing propane and mixed cresols as the duosolvents, to a depth such that the VI of the extracted etfiuent oil was 103.
  • the net yield of raflinate was 79% by
  • the extracted oil was of good color but possessed considerable haze and had poor stability and thus required clay contacting before the oil had satisfactory properties.
  • the oil was therefore contacted with 18 pounds per barrel of clay at a temperature of 450 F. A 3% volume loss was incurred during the contacting step and the net yield of finished oil was 76.5% by Weight, based on the dewaxed starting material.
  • Example III A propane-deasphalted (DA) and dewaxed (DW) residual lubricating oil (New Mexico-Ellenburger) having a VI of B5 was selectively hydrogenated over a. supported nickel sulfide catalyst having the same average composition as in Example I.
  • the temperature of the hydrotreatrnent was 707 F. and the pressure was 1500 p.s.i.
  • the oil feed was contacted with the catalyst at a space velocity of 0.4 and a hydrogen-to-oil mole ratio of 30 to 1 was maintained throughout. Gas was continuously bled from the reaction system and fresh hydrogen added in order to maintain the molar ratio of H 8 to H at 0.001.
  • the VI of the hydrotreated oil was and the net yield was 90% by weight.
  • the aromatics content of the untreated and treated oil were as follows:
  • Example IV The same dewaxed residual lubricating oil as in Exam: ple III was extracted in a conventional Duosol solvent extraction system, employing propane and mixed cresols as the duo-solvents, to a depth such that the VI of the extracted rafiinate oil was 96. The yield of rafiinate was only 66% by weight.
  • the inven tion has great value in providing a method by which satisfactory lubricating oil may be made in larger yields.
  • the advantage of the selective hydrogenation of lubricating oils in the manner of the invention is not limited thereto.
  • the lubricating oils produced according to the invention have certain properties superior to those of conventionally treated lubricating oils. These oils are particularly susceptible to the addition of VI improving agents, as may be seen in the following example:
  • Example V A waxy naphthenic lubricating oil distillate from the Four Corners district of Utah having a viscosity of about 250 S.U.S. at F. was hydrotreated over a Ni S on-alumina catalyst in accordance with the invention.
  • the operating conditions were as follows:
  • the hydrogen consumption was about 250 sci/barrel of feed and the product contained 94.0% by volume of Waxy hydrogenated lubricating oil distillate having a VI'of 85.
  • the V1 improver susceptibility of this relatively low VI oil was then compared with that of a deeply extracted raflinate produced by extraction of the same waxy distillate starting material with furfural to a VI of 100.
  • Add-1 Oopolyruerpf type referred to in 11.8. 2,737,496 (Copolymer of 2-1nethyl-5-vinyl pyridine and lauryl, stearyl, and methyl methacry- 35%1-2: Acryloid 966 (N-vinylpyrrolldone-lauryl methacrylate copoly- From the foregoing, it is clear that the oil which had been selectively hydrogenated according to the invention was almost twice as susceptible to additive VI improvement as the conventionally refined oil. A noteworthy aspect of this unexpected benefit is that it is present not only when the VI of the hydrotreated oil is below that of the extracted oil but also when the VI of the additive containing oil is greater than the extracted oil.
  • high viscosity index oils may be made in high yields from relatively low VI lubricating oil starting materials.
  • Example VI A commercially available pelleted catalyst comprising 40% by Weight of nickel in the form of nickel carbonate, composited with granulated kieselguhr, was ground to pass through a 6-8 mesh standard screen. Twohundredninety-three grams of the ground catalyst were then placed in a cylindrical pressure vessel, having appropriate inlet, outlet, and support means, to form a fixed foraminous bed of granulated nickel catalyst. At operating condi tions of 707 F., 1500 psi. pressure, and a liquid hourly space velocity, (LHSV) of one volume of liquid per volume of catalyst per hour, the following three steps were performed:
  • the sulfided nickel catalysts used in the invention have sutficient mechanical strength that they may be used in the granular or pelleted form in a fixed bed Without a support.
  • the catalyst can be prepared by impregnating or admixing suitable supporting materials with various reducible nickel salts, followed by conventional drying and/ or pelleting procedures. When the catalyst is in the form of such salts, it can be reduced to the metallic form prior to sulfiding if desired.
  • Materials which are suitable as catalyst supports for this invention include various refractory oxides,'which arees's'entially nonreactive with hydrogen sulfide, such as alumina, silica, thoria, zirconia, and titania. Silica and alumina are particularly preferred to be used as catalyst supports in the practice of this invention. Alumina clays of the montmorillonitic type are also useful as supports for the catalyst of the process.
  • the present invention may be used to supplant conventional lubricat'ing oil solvent extraction facilities and in many cases clay contacting facilities as well.
  • the invention may be also used advantageously in cooperation with such conventional refining facilities, eitherin series or in parallel with, leg, solvent extraction and/ or acid treating processes.
  • high viscosity index lubricating oils may be produced at higher yields than were heretofore possible at equivalent quality levels.
  • the invention is equally advantageous whether it is used for treating narrow viscosity range lubricating oil stocks or broad viscosity range stocks. Moreover, the entire lubricating oil fraction of a given crude oil may be processed according to this process without prior separation into narrow viscosity ranges. However, as pointed out hereinbefore, it is preferred to separate and deasphalt the residual lubricating oil portion prior to the selective hydrogenation. After such separation, however, the deasphalted residue and separated distillate may be recombined if desired.
  • the viscosity of the oil undergoes some decrease because of the presence of lower viscosity materials resulting from hydrocracking, which can not be eliminated entirely, and from oxygen and sulfur atom removal, as well as the natural lowering due to conversion of polyaromatics to naphtheno-monoaromatics.
  • the viscosity of the treated oil may be raised substantially by stripping out the light ends under reduced pressure with, for example, steam, nitrogen, or other inert gas.
  • some lubricating oils processed in this manner contain small amounts of higher boil ling non-strippable low viscosity materials.
  • Such higher boiling lowviscosity materials are produced during the hydrotreatment by isomerization and also by hydrocracking of short alkyl side chains. These may best be removed by distillation. It should be noted, however, the lower viscosity, higher-boiling materials removed accordingly are frequently good lubricants and may have viscosity indices as great as or even greater than the bulk of the treated oil. Such oils may advantageously be used as blending agents for higher viscosity oils. The degree of viscosity decrease depends of course on the particular character of each lubricating oil crude from which the oil is derived. Therefore, in some instances where a particular viscosity range is desired it may be preferred to employ a slightly higher viscosity oil as a starting material than would be used for conventional viscosity index-improving refining processes.
  • the lubricating oil to be hydrotreated according to the invention need notbe dcwaxed prior to hydrogenation. Moreover, it is a preferred aspect of the invention that the oil not be dewaxed since even greater overall lubricating oil yields may be obtained.
  • the mechanism by which this further advantage is obtained appears to be that the molecular configurations of the treated oil components are more varied after selective hydrogenation according to the invention because of a small amount of isomerization and mild hydrocracking which take place noncurrently with the hydrogenation. The greater variety in molecular configuration thus creates a higher degree of crystalline heterogeneity which depresses the pour point of the hydrogenated oil.
  • An additional advantage of lubricating oils produced according to the invention is that they have higher peptizing power, which, by maintaining potential sludge-forming materials in solution, contributes to superior oxidation stability.
  • a process for the treatment of essentially asphalt-free petroleum lubricating oils containing polycyclic aromatics to reduce the sulfur content thereof and to convert selectively polycyclic aromatics to incompletely saturated compounds having one aromatic ring per molecule without substantial cracking of the oils which comprises contacting said oils at a temperature of from about 600 to about 800 F.
  • a nickel sulfide catalyst in the presence of a treating gas containing hydrogen sulfide and hydrogen in a ratio of from 0.0002 to 0.02 moles of hydrogen sulfide per mole of hydrogen, the average atomic ratio of nickel to sulfur in said nickel sulfide catalyst being at least 1.3:1 but not more than 3:1, and the consumption of hydrogen being not less than but not more than about 500 standard cubic feet per barrel of lubricating oil treated.

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  • Engineering & Computer Science (AREA)
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US791074A 1959-02-04 1959-02-04 Hydrogenation of lubricating oils to remove sulfur and saturate aromatics Expired - Lifetime US3012963A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
NL125742D NL125742C (en, 2012) 1959-02-04
NL248007D NL248007A (en, 2012) 1959-02-04
US791074A US3012963A (en) 1959-02-04 1959-02-04 Hydrogenation of lubricating oils to remove sulfur and saturate aromatics
DE19601470615 DE1470615A1 (de) 1959-02-04 1960-02-02 Verfahren zur Hydroraffination von Schmieroelfraktionen
GB3669/60A GB897240A (en) 1959-02-04 1960-02-02 A process for the treatment of lubricating oils
FR817317A FR1246671A (fr) 1959-02-04 1960-02-02 Traitement d'hydrogénation des huiles lubrifiantes

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DE (1) DE1470615A1 (en, 2012)
FR (1) FR1246671A (en, 2012)
GB (1) GB897240A (en, 2012)
NL (2) NL248007A (en, 2012)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3132089A (en) * 1960-12-23 1964-05-05 Union Oil Co Hydrocracking process with pre-hydrogenation
US3192153A (en) * 1962-11-06 1965-06-29 Socony Mobil Oil Co Inc Preparation of transformer oils
US3245903A (en) * 1962-04-10 1966-04-12 British Petroleum Co Hydrocatalytic refining of lubricating oils
US3384676A (en) * 1965-01-15 1968-05-21 Universal Oil Prod Co Hydrogenation of para and meta xylene mixtrues
US3520796A (en) * 1968-08-21 1970-07-14 Gulf Research Development Co Making lubricating oils by hydrotreating and dewaxing
US3617475A (en) * 1970-01-15 1971-11-02 Gulf Research Development Co Process for producing lubricating oils with good low temperature hazing properties
US4285807A (en) * 1979-09-04 1981-08-25 Gulf Research & Development Company Lubricating oil hydrotreating process
US4515680A (en) * 1983-05-16 1985-05-07 Ashland Oil, Inc. Naphthenic lube oils
US20050234275A1 (en) * 2004-04-16 2005-10-20 Shifang Luo Reduction of naphthalene concentration in aromatic fluids
US20080300157A1 (en) * 2007-03-30 2008-12-04 Wu Margaret M Lubricating oil compositions having improved low temperature properties

Citations (6)

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Publication number Priority date Publication date Assignee Title
US2673175A (en) * 1954-03-23 Synthetic lubricating oil
US2706167A (en) * 1950-06-16 1955-04-12 Sun Oil Co Process for hydrogenating hydrocarbon oils
US2779711A (en) * 1955-02-28 1957-01-29 Standard Oil Co Refining of lubricating oils
US2779713A (en) * 1955-10-10 1957-01-29 Texas Co Process for improving lubricating oils by hydro-refining in a first stage and then hydrofinishing under milder conditions
US2879223A (en) * 1955-09-21 1959-03-24 Texas Co Method for producing a lubricating oil
US2914470A (en) * 1955-12-05 1959-11-24 Sun Oil Co Hydrorefining of petroleum

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2673175A (en) * 1954-03-23 Synthetic lubricating oil
US2706167A (en) * 1950-06-16 1955-04-12 Sun Oil Co Process for hydrogenating hydrocarbon oils
US2779711A (en) * 1955-02-28 1957-01-29 Standard Oil Co Refining of lubricating oils
US2879223A (en) * 1955-09-21 1959-03-24 Texas Co Method for producing a lubricating oil
US2779713A (en) * 1955-10-10 1957-01-29 Texas Co Process for improving lubricating oils by hydro-refining in a first stage and then hydrofinishing under milder conditions
US2914470A (en) * 1955-12-05 1959-11-24 Sun Oil Co Hydrorefining of petroleum

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3132089A (en) * 1960-12-23 1964-05-05 Union Oil Co Hydrocracking process with pre-hydrogenation
US3245903A (en) * 1962-04-10 1966-04-12 British Petroleum Co Hydrocatalytic refining of lubricating oils
US3192153A (en) * 1962-11-06 1965-06-29 Socony Mobil Oil Co Inc Preparation of transformer oils
US3384676A (en) * 1965-01-15 1968-05-21 Universal Oil Prod Co Hydrogenation of para and meta xylene mixtrues
US3520796A (en) * 1968-08-21 1970-07-14 Gulf Research Development Co Making lubricating oils by hydrotreating and dewaxing
US3617475A (en) * 1970-01-15 1971-11-02 Gulf Research Development Co Process for producing lubricating oils with good low temperature hazing properties
US4285807A (en) * 1979-09-04 1981-08-25 Gulf Research & Development Company Lubricating oil hydrotreating process
US4515680A (en) * 1983-05-16 1985-05-07 Ashland Oil, Inc. Naphthenic lube oils
US20050234275A1 (en) * 2004-04-16 2005-10-20 Shifang Luo Reduction of naphthalene concentration in aromatic fluids
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NL125742C (en, 2012)
GB897240A (en) 1962-05-23
FR1246671A (fr) 1960-11-18
NL248007A (en, 2012)
DE1470615A1 (de) 1969-03-20

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