US3414506A - Lubricating oil by hydrotreating pentane-alcohol-deasphalted short residue - Google Patents

Lubricating oil by hydrotreating pentane-alcohol-deasphalted short residue Download PDF

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US3414506A
US3414506A US388402A US38840264A US3414506A US 3414506 A US3414506 A US 3414506A US 388402 A US388402 A US 388402A US 38840264 A US38840264 A US 38840264A US 3414506 A US3414506 A US 3414506A
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oil
alcohol
lubricating oil
hydrogen
residue
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Campagne Nicolaas Van Lookeren
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Shell USA Inc
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Shell Oil Co
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    • 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
    • C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
    • C10G67/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only
    • C10G67/04—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only including solvent extraction as the refining step in the absence of hydrogen
    • C10G67/0454—Solvent desasphalting
    • C10G67/0463—The hydrotreatment being a hydrorefining
    • 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
    • C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
    • C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
    • C10G21/12—Organic compounds only
    • C10G21/16—Oxygen-containing compounds
    • 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

Definitions

  • This invention relates to a process for the preparation of lubricating oils from asphalt-containing residual petroleum fractions.
  • the residue is rst subjected to a fractional distillation in order to obtain light and medium lubricating oils.
  • the remaining heavy residue is de-asphalted by means of a light hydrocarbon such as propane.
  • the de-asphalted residue is suitable for use as a base lubricating oil.
  • base lubricating oil it is meant an oil which, as such or upon blending with other oil and/or admixture of additives, is ready for sale as a finished lubricating oil.
  • a disadvantage of the conventional process is that the yield of valuable lubricating oil components from a propane treatment is proportionally low, a relativelylarge part of the residue, in many cases 60% by volume or more, being removed as an asphaltic residue. These high losses are generally necessary since de-asphalting to a lower yield of asphal would lead to a lubricating oil which does not meet the requirements of present specifications, especially with regard to the Ramsbottom Carbon Test and the viscosity level.
  • a de-asphalted oil, or oil solution is obtained which, after a catalytic treatment with hydrogen at elevated temperature and pressure, yields a viscous base lubricating oil with an excellent viscosity index.
  • C3+ hydrocarbons it is meant hydrocarbons and mixtures thereof having three or more carbon atoms in the molecule.
  • the process of the invention comprises extracting asphalt-containing petroleum residues with a C3+hydrocar bon-alcohol mixture, separating the resulting liquid asphaltic raffinate phase from the oleaginous extract phase, separating the extract phase into a hydrocarbon-alcohol mixture and a de-asphalted oil, and subjecting the deasphalted oil to a catalytic treatment with hydrogen at elevated temperature and pressure.
  • the relatively large amount of potential lubricating oil components which is removed with the asphalt in the usual treatment withpropane is retained by extracting the residue with a C3+hydrocar bon-alcohol mixture.
  • the ranate is mainly asphaltenes and resins and contains little potential lubricating oil components.
  • the extract, which contains the added components is a complex mixture of relatively high-molecular weight hydrocarbons, partly having a naphthenic and polyaromatic structure and as a rule having relatively high sulfur and nitrogen content.
  • the extract is a suitable lubricating oil stock if it is subjected to a catalytic treatment with hydrogen at elevatedvtemperature and pressure.
  • a catalytic treatment with hydrogen at elevatedvtemperature and pressure.
  • the complex mixture of relatively high-molecular weight naphthenic and polyaromatic compounds are converted into lubricating oil components.
  • removal of sulfur and nitrogen is eifected and ring opening of polyaromatic and naphthenic structures occurs, which results in hydrocarbons with good viscosity properties.
  • Another advantage of the hydrogen treatment is that upgrading of the other oil components occurs at the same tlme.
  • the solvent combination according to the invention has, on the one hand, a solvency for oil which is equal to, or greater than, that of aliphatic hydrocarbons, while on the other hand, it has less solvency for asphaltenes and thus is able to extract deeper into the residue. Also, the separation which is effected in the complex mixture of higher-molecular weight compounds present in the residue is quite different from that obtained with hydrocarbons or alcohols only.
  • the hydrocarbonalcohol mixture causes, for instance, the polar sulfur and nitrogen compounds, which are potential lubricating oil components-with the exception of the highest-molecular weight representatives-to be completely or substantially extracted, whereas the wax content in the extract is relatively low. According to the present invention much higher yields of lubricating oil can therefore be obtained from a given residue; in many cases this yield is twice as high as that obtained by lthe conventional method of deasphalting with propane.
  • Another advantage of the present solvent combination is that as a result of both the choice of hydrocarbons and alcohols and the choice of the hydrocarbon to alcohol ratio the desired yield of oil components from asphaltcontaining residues of different natures can be obtained in a simple way.
  • the C3+ hydrocarbon component preferably consists of one or more aliphatic hydrocarbons with 4-10 carbon atoms in the molecule.
  • technical mixtures such as hydrocarbon oil fractions-for example, light naphtha fractions with boiling ranges of between and 150 C.- may be used.
  • hydrocarbon oil fractions for example, light naphtha fractions with boiling ranges of between and 150 C.- may be used.
  • these mixtures containing minor quantities of other hydrocarbons as long as the mixture as such retains the character of a C3+ hydrocarbon.
  • the invention will be described below using pentane as the solvent.
  • the alcohol component in the solvent combination preferably consists of one or more aliphatic alcohols with 1-4 carbon atoms in the molecule. There is no objection to these alcohols containing other alcohols and/or water as long as the mixture as such retains the character of aliphatic alcohols with 1-4 carbon atoms, preferably not more than 2% by volume of water should be present in the extraction solvent.
  • the amount of alcohol in the solvent mixture can vary over a broad range and in general is about to about 80% by volume.
  • the amount of alcohol to be used in a given situation depends upon the nature of the alcohol and on the hydrocarbon. With, for example, a pentane/ alcohol mixture, the concentration of alcohol is desirably about 15-35% for methanol and 55-80% for butanol.
  • the extraction is carried out with 2-20 parts by volume and preferably 4-10 parts by volume of hydrocarbon/alcohol mixture per part by volume of asphaltcontaining residue.
  • the solvent ratio used in a given situation is determined by, among7 other factors, the type of residue and by the nature and content of the asphalt components. Relatively high solvent ratios, which-for example-may be useful in bringing about a rapid phase separation, may be used without difficulty, considering the low cost of recovering the solvents from the extract phase.
  • the yield of oil components usually shows a relatively large increase if the percentage by volume of the hydrocarbon component in the hydrocarbon-alcohol mixture is increased; to a lesser extent this is also the case if a higher ratio by volume of the hydrocarbon-alcohol mixture on residue is chosen. Higher oil yields may also be obtained by performing the extraction at higher temperatures.
  • asphalt After removal of the hydrocarbon-alcohol components, asphalt is obtained in the form of a hard, brittle product, which, owing to its high asphaltene content, is of better quality than propane asphalt and may be applied, for instance, in the preparation of synthetic asphaltic bitumens.
  • the viscosity of the residue may be effected, for instance, by dissolving a Certain quantity O f pentane and/or one or more other lowviscous hydrocarbons therein.
  • the quantity of pentane, etc. added should preferably not be so large as to bring about precipitation of asphaltenes in the residue.
  • Very suitable is, for example, a dilution of 20-35% by volume of pentane calculated on residue,
  • a correspondingly smaller quantity of pentane or the like may be used, if desired, in the solvent combination.
  • the viscosity may also be lowered by introducing the residue into the extraction solvent at a somewhat elevated temperature, for instance, between and 90 C.
  • the extraction of asphalt-containing residues with the aid of the present hydrocarbon-alcohol mixtures can be effected both batchwise and continuously. It is preferably carried out, however, in a continuously operating, multistage countercurrent extraction system, one of the devices which may be considered for this purpose being a column installed vertically and provided with stationary bafes or a column in which a shaft carrying discs has been rotatably mounted, as is described, for instance, in British patent specification 690,730.
  • residues obtained by direct distillation of crude oils and those originating from thermal or catalytic cracking processes may be used as starting materials. It is recommended, however, to start from residues having parainbase crude oils as their origin. Further, preference is given to so-called short residues, i.e. residues not containing light or medium lubricating oil components.
  • the yield of residual lubricating oil which is obtained from de-asphalted oil treated with hydrogen after removal of light and medium lubricating oil components usually amounts to at least 1.5 times the quantity obtained according to the conventional mode of preparation, its viscosity being equal to, or higher than, that of the conventional oil.
  • the hydrogen treatment is carried out at elevated temperature and pressure with the aid of a hydrogenation catalyst.
  • a hydrogenation catalyst Such catalysts are well known and are available commercially and in general contain as a hydrogenation component one or more elements from the left-hand column of the sixth group (chromium, molybdenum, tungsten) and the eighth group of the Periodic System. These elements are preferably present as the sulfdes and as a rule are supported on a carrier.
  • Carriers for instance, can be natural or synthetic alumina and/ or silica containing materials. Carriers containing silica with alumina can be advantageous, because of their tendency to open polyaromatic and naphthenic ring structures.
  • Silica-alumina cracking catalysts containing about 60-90% silica are suitable carriers. Examples of suitable catalysts are combinations of nickel sulfide and/or cobalt sulfide with molybdenum sulfide and/or tungsten sulfide.
  • the atomic ratio of the metals of the eighth group to those of the left-hand column of the sixth group is, as a rule, between 1:20 and 1:1.
  • the reaction temperature is usually between 370 and 430 C.; temperatures between 380 and 420 C.
  • the hydrogen treatment is usually carried out at a pressure of at least atm. and preferably above atm. In general pressures above about 200 atm, are not used.
  • the hydrogen treatment preferably is effected under so-called trickle conditions.
  • the oil which may be partly liquid and partly in vapor form, passes downwardly over a solid catalyst bed in the presence of hydrogen or a hydrogen-containing gas; the oil flowing in a thin film over the catalyst particles.
  • a hydrogen-containing gas for instance, a mixture of hydrogen and light hydrocarbons, may be used.
  • the gases should preferably contain more than 50% by Volume of hydrogen.
  • Very suitable are, for instance, hydrogen-containing gases obtained from the catalytic reforming of gasoline fractions.
  • the space velocity usually is 0.5-5 kg. and preferably 1-3 kg. of de-asphalted oil per hour per liter of catalyst.
  • the hydrogen2oil ratio is between 100 and 1000 normal liters and preferably between 200 and 500 normal liters of hydrogen per kg. of oil.
  • the same type of catalyst may be used as in the first hydrogen treatment, the difference being, however, that the catalyst is supported on an alumina carrier containing substantially no silica.
  • This treatment which should be looked upon as so-called hydrofining, may be performed at lower temperatures, for example, between 250 C. and 360 C. and preferably between 300 and 350 C. and at the same, or lower, hydrogen pressures, for instance, between 30 and 60 atm., and using 50-200 normal liters of hydrogen per kg. of oil.
  • This second hydrogen treatment may serve, for example, to increase the stability of the oil and/or to improve its color.
  • the lubricating oil is usually subjected to a fractional distillation in vacuo to separate tops and to obtain light and/ or medium lubricating oil distillates and the residual lubricating oil.
  • the fractions obtained may subsequently be extracted according to the conventional method to remove aromatic compounds, etc., after which, if desired, the raflinates are dewaxed.
  • the dewaxing procedure according to the present process may be performed, if desired, before the hydrogen treatment, i.e. immediately after the de-asphalting process. This is advantageous, for example, in those cases in which the same type of hydrocarbonalcohol mixture is used for dewaxing and de-asphalting.
  • the starting material is a residual oil fraction obtained by distillation of an asphaltic crude oil originating from the Middle East. This residual oil fraction was subjected to fractional distillation in order to obtain a' light and a medium lubricating oil fraction.
  • the remaining asphalt-containing residue having a sulfur content of 5.22% w. and a kinematic vicosity of 1284 cs. at 210 F., is diluted with a mixture of 20% w. pentane and 2% methyl alcohol in order to lower viscosity.
  • the diluted residue is introduced to extraction column 1: via line 2.
  • the extraction column is provided with bafes and is equivalent to 6 theoretical stages.
  • the asphalt-containing residue is charged at the ratio of 100 parts by weight per hour.
  • the extraction solvent is continuously introduced near the bottom of the column, via line 3, at a rate of 478 parts by weight/hour.
  • the total composition of the extraction solvent, including the quantity added to the residue to lower the viscosity is 300 parts by weight of pentane, 125 parts by weight of methyl alcohol and 75 parts by weight of isopropanol.
  • the asphalt withdrawn via line 6 has a Ring and Ball temperature of 102 C. and a penetration of 0.1 mm. at 25 C. (ASTM D-5-61).
  • the oil-containing extract phase is removed continuously via line 7 in the form of a clear liquid having a dark-green color.
  • the extract phase is first passed through coalescer 8 filled with polypropylene wool so as to remove any entrained droplets of asphalt-containing raffinate phase and is then charged into stripping column 11 via line 9 and heat exchanger 10.
  • Pentane which is evaporated, is removed via line 12 and, after condensation in cooler 13, is recycled to the process through lines 14 and 15.
  • the bottom temperature of stripping column 11 is 70 C. and the top temperature 33 C.
  • the heterogeneous mixture of de-asphalted oil and alcohols flowing from the bottom of stripping column 11 is cooled to 20 C. and introduced into settling vessel 17 via line 16. At the top of this settler, the separated alcohol mixture is removed and recycled to the process via line 18.
  • the alcohol contains 2% w. of oil.
  • the de-asphalted oil separated in settling vessel 17 is passed via line 19 to stripping column 20 where, at a bottom temperature of 120 C., remaining extraction solvent is removed with the aid of nitrogen and is recycled to the process va cooler 21 and line 22. In this way, 56 parts by weight of de-asphalted oil per hour is obtained, the properties of which have been listed in column 1 of Table I.
  • the de-asphalted oil is then subjected to a catalytic hydrogen treatment by charging it (via line 23) together with hydrogen (via line 24) into the top of reactor 25, which has been provided with a fixed catalyst bed, at a pressure of 175 atm. and a temperature of 410 C.
  • the catalyst is sulded nickel-molybdenum on an alumina carrier.
  • the oil is passed through the reactor 'at a space velocity of 1 kg. of oil per liter of catalyst per hour, a hydrogemoil ratio of 500 normal liters of hydrogen per kg. of oil being used.
  • the effluent from reactor 25 passes through cooler 26 and is introduced into separator 27 for the separation of gaseous components, such as hydrogen and hydrogen sulfide. Oil from the separator is passed via line 28 to distillation column 29 to remove other volatile components. Bottoms from column 29 are passed via line 30 to vacuum fractonating column 31. Properties of the oil after the hydrogen treatment are included in column 2 of Table I.
  • eating oil according to conventional process, starting from sarne asphalt to de-asphalting, hydrogenasphalt-containing residue) asphalt-containing residue) containing residue ation and conventional Working-up Yields, Properties Yields, Properties Yield, Properties Percent w. Percent W. Percent W.
  • Kin. vise. es., 140 F Kin. vise. es., 140 F., 230 15. 5 (Iin. vise. es., 140o F., 160.
  • the lubricating oil distillate fractions are separately extracted in 4 stages in countercurrent extraction with furfural and subsequently dewaxed in order to obtain oils with a viscosity index of 95 or higher and a pour point of -l0 C. or lower.
  • the extraction is performed continuously in extraction column 37 provided with a rotating shaft with discs, a urfural: oil weight ratio of 3.8 being used.
  • the oil fractions collected via lines 33, 34 and 35 are consecutively passed (via line 36) to column 37 near the bottom and are passed counter-currently to the furfural introduced near the top of the extraction column via line 38.
  • the extract phase leaving the extraction column via line 39 is separated in fractionation column 40 into an aromatic extract, which is carried off via line 41, and furfural, which is recirculated to the extraction column via line 38.
  • the rainates leaving extraction column 37 via line 42 are introduced into dewaxing plant 43, a diluent:oil volume ratio of 4 being used.
  • the Wax obtained is carried off via line 44, and the filter oil is charged into distillation column 45.
  • Methylethylketone/ toluene is obtained from the top of column 45 andA is recycled to the dewaxing plant via line 46.
  • residual lubricating oil, light lubricating oil distillate and spindle oil are obtained via lines 47, 48, and 49, respectively.
  • 2.5 parts by weight of hydrogen, as well as the properties of these oils, have been listed in Table Il.
  • the solvent power may be increased by applying the oil diluted with a solvent having a greater solvent power for hydrogen than the oil.
  • Suitable solvents are, for example, aliphatic hydrocarbons with 5-12 carbon atoms in the molecule or mixtures containing these hydrocarbons, such as naphtha and gasoline fractions.
  • a process for extracting lubricating oils and potential lubricating oils from asphalt-containing residues which comprises contacting the residues with a solvent mixture consisting essentially of a C4-C7 aliphatic hydrocarbon and a CVC., alcohol, the concentration of alcohol in the solvent mixture being dependent upon the alcohol carbon number and varying between the range of 15-35 percent by volume for methanol and the range of 55480 percent by volume for butanol, said hydrocarbon having a boiling point lower than said alcohol, separating an asphaltic rainate phase from an oleaginous extract phase, evaporating solvent hydrocarbon from the extract phase which results in the formation of a liquid alcohol phase and a de-asphalted oil phase, and recovering de-asphalted oil.
  • a solvent mixture consisting essentially of a C4-C7 aliphatic hydrocarbon and a CVC., alcohol, the concentration of alcohol in the solvent mixture being dependent upon the alcohol carbon number and varying between the range of 15-35 percent by volume for methanol and the range of 55

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  • Engineering & Computer Science (AREA)
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  • Organic Chemistry (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
US388402A 1963-08-12 1964-08-10 Lubricating oil by hydrotreating pentane-alcohol-deasphalted short residue Expired - Lifetime US3414506A (en)

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Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3514395A (en) * 1968-05-29 1970-05-26 Sun Oil Co Process for producing a high aromatic,low color,uv stable process oil
US3544450A (en) * 1968-09-09 1970-12-01 Universal Oil Prod Co Petroleum crude oil conversion process
US3546098A (en) * 1968-07-24 1970-12-08 Chevron Res Making a lube oil by hydrocracking and solvent extraction
US3617476A (en) * 1969-04-10 1971-11-02 Texaco Inc Lubricating oil processing
US3627675A (en) * 1969-10-16 1971-12-14 Foster Wheeler Corp Solvent deasphalting with two light hydrocarbon solvents
US3658692A (en) * 1969-10-28 1972-04-25 Exxon Research Engineering Co Preparation of white oils with aluminum-alkyl activated iron group metal catalysts
US3779896A (en) * 1971-08-04 1973-12-18 Texaco Inc Lube oil manufacture
US3972807A (en) * 1975-06-25 1976-08-03 Universal Oil Products Company Hydrocarbon deasphalting via solvent extraction
US4085036A (en) * 1976-10-01 1978-04-18 Gulf Research & Development Company Process of hydrodesulfurization and separate solvent extraction of distillate and deasphalted residual lubricating oil fractions
US4414105A (en) * 1980-09-01 1983-11-08 Institut Francais Du Petrole Process for deasphalting an asphaltene containing hydrocarbon charge
US4440633A (en) * 1981-04-30 1984-04-03 Institut Francais Du Petrole Process for solvent deasphalting heavy hydrocarbon fractions
EP0128047A1 (en) * 1983-06-06 1984-12-12 Exxon Research And Engineering Company The selective separation of heavy oil using a mixture of polar and nonpolar solvents
US4514287A (en) * 1982-01-08 1985-04-30 Nippon Oil Co., Ltd. Process for the solvent deasphalting of asphaltene-containing hydrocarbons
US4592831A (en) * 1984-12-12 1986-06-03 Lummus Crest Inc. Solvent for refining of residues
EP0187947A1 (en) * 1984-12-12 1986-07-23 Lummus Crest, Inc. Solvent for refining of residues
US4810367A (en) * 1986-05-15 1989-03-07 Compagnie De Raffinage Et De Distribution Total France Process for deasphalting a heavy hydrocarbon feedstock
US9394495B1 (en) * 2013-09-18 2016-07-19 Thomas George Murray Post hydrotreatment finishing of lubricant distillates
WO2017117161A1 (en) 2015-12-28 2017-07-06 Exxonmobil Research And Engineering Company Fuel components from hydroprocessed deasphalted oils
WO2017117176A1 (en) 2015-12-28 2017-07-06 Exxonmobil Research And Engineering Company Integrated resid deasphalting and gasification
WO2017117178A1 (en) 2015-12-28 2017-07-06 Exxonmobil Research And Engineering Company Bright stock production from deasphalted oil
WO2017218602A2 (en) 2016-06-13 2017-12-21 Murray Extraction Technologies Llc Improvement of properties of hydroprocessed base oils
WO2018125284A1 (en) 2016-12-29 2018-07-05 Exxonmobil Research And Engineering Company Base stocks and lubricant compositions containing same
WO2018125610A1 (en) 2016-12-29 2018-07-05 Exxonmobil Research And Engineering Company Solvent extraction for correction of color and aromatics distribution of heavy neutral base stocks
WO2019005009A1 (en) 2017-06-27 2019-01-03 Exxonmobil Research And Engineering Company COMBUSTIBLE COMPONENTS OF HYDROPOWERED DISASPHALATED OILS
WO2019164776A1 (en) 2018-02-23 2019-08-29 Exxonmobil Research And Engineering Company Removal of polynuclear aromatics from severely hydrotreated base stocks
US10494579B2 (en) 2016-04-26 2019-12-03 Exxonmobil Research And Engineering Company Naphthene-containing distillate stream compositions and uses thereof
US11198825B2 (en) 2019-10-21 2021-12-14 Exxonmobil Research And Engineering Company Monitoring of hydroprocessed fluids by optical spectroscopy

Citations (4)

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US3011972A (en) * 1957-02-25 1961-12-05 Sinclair Refining Co Method for the manufacture of an oxidation stable bright stock
US3053760A (en) * 1960-03-04 1962-09-11 Gulf Research Development Co Preparing bright stocks by hydrogenation
US3078222A (en) * 1960-07-27 1963-02-19 Gulf Research Development Co Preparation of multi-grade lubricating oil by severe hydrogenation and urea adduction
US3228870A (en) * 1964-12-14 1966-01-11 Phillips Petroleum Co Treatment of asphaltic crude oils

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3011972A (en) * 1957-02-25 1961-12-05 Sinclair Refining Co Method for the manufacture of an oxidation stable bright stock
US3053760A (en) * 1960-03-04 1962-09-11 Gulf Research Development Co Preparing bright stocks by hydrogenation
US3078222A (en) * 1960-07-27 1963-02-19 Gulf Research Development Co Preparation of multi-grade lubricating oil by severe hydrogenation and urea adduction
US3228870A (en) * 1964-12-14 1966-01-11 Phillips Petroleum Co Treatment of asphaltic crude oils

Cited By (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3514395A (en) * 1968-05-29 1970-05-26 Sun Oil Co Process for producing a high aromatic,low color,uv stable process oil
US3546098A (en) * 1968-07-24 1970-12-08 Chevron Res Making a lube oil by hydrocracking and solvent extraction
US3544450A (en) * 1968-09-09 1970-12-01 Universal Oil Prod Co Petroleum crude oil conversion process
US3617476A (en) * 1969-04-10 1971-11-02 Texaco Inc Lubricating oil processing
US3627675A (en) * 1969-10-16 1971-12-14 Foster Wheeler Corp Solvent deasphalting with two light hydrocarbon solvents
US3658692A (en) * 1969-10-28 1972-04-25 Exxon Research Engineering Co Preparation of white oils with aluminum-alkyl activated iron group metal catalysts
US3779896A (en) * 1971-08-04 1973-12-18 Texaco Inc Lube oil manufacture
US3972807A (en) * 1975-06-25 1976-08-03 Universal Oil Products Company Hydrocarbon deasphalting via solvent extraction
US4085036A (en) * 1976-10-01 1978-04-18 Gulf Research & Development Company Process of hydrodesulfurization and separate solvent extraction of distillate and deasphalted residual lubricating oil fractions
US4414105A (en) * 1980-09-01 1983-11-08 Institut Francais Du Petrole Process for deasphalting an asphaltene containing hydrocarbon charge
US4440633A (en) * 1981-04-30 1984-04-03 Institut Francais Du Petrole Process for solvent deasphalting heavy hydrocarbon fractions
US4514287A (en) * 1982-01-08 1985-04-30 Nippon Oil Co., Ltd. Process for the solvent deasphalting of asphaltene-containing hydrocarbons
EP0128047A1 (en) * 1983-06-06 1984-12-12 Exxon Research And Engineering Company The selective separation of heavy oil using a mixture of polar and nonpolar solvents
US4592831A (en) * 1984-12-12 1986-06-03 Lummus Crest Inc. Solvent for refining of residues
EP0187947A1 (en) * 1984-12-12 1986-07-23 Lummus Crest, Inc. Solvent for refining of residues
US4810367A (en) * 1986-05-15 1989-03-07 Compagnie De Raffinage Et De Distribution Total France Process for deasphalting a heavy hydrocarbon feedstock
US9394495B1 (en) * 2013-09-18 2016-07-19 Thomas George Murray Post hydrotreatment finishing of lubricant distillates
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