US3847800A - Method for removing sulfur and nitrogen in petroleum oils - Google Patents

Method for removing sulfur and nitrogen in petroleum oils Download PDF

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Publication number
US3847800A
US3847800A US00385894A US38589473A US3847800A US 3847800 A US3847800 A US 3847800A US 00385894 A US00385894 A US 00385894A US 38589473 A US38589473 A US 38589473A US 3847800 A US3847800 A US 3847800A
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oil
nitrogen
oxidizing gas
sulfur
solvent
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E Guth
A Diaz
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KVB Inc
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KVB ENG Inc
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Priority to US00385894A priority Critical patent/US3847800A/en
Priority to GB2156674A priority patent/GB1437569A/en
Priority to DE2424274A priority patent/DE2424274C3/de
Priority to CA200,763A priority patent/CA1046004A/en
Priority to NL7407257A priority patent/NL7407257A/xx
Priority to IN1365/CAL/74A priority patent/IN141762B/en
Priority to JP7863974A priority patent/JPS5337081B2/ja
Priority to IE1506/74A priority patent/IE39619B1/xx
Priority to AU71509/74A priority patent/AU492349B2/en
Priority to FR7425960A priority patent/FR2240280B1/fr
Priority to SU2049070A priority patent/SU508220A3/ru
Priority to BE147170A priority patent/BE818350A/xx
Priority to BR6369/74A priority patent/BR7406369D0/pt
Priority to IT26012/74A priority patent/IT1017927B/it
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Assigned to KVB, INC. reassignment KVB, INC. CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). EFFECTIVE APRIL 10, 1972. Assignors: KVB ENGINEERING, INC. A CA CORP.
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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
    • C10G27/00—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation
    • C10G27/04—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen
    • C10G27/12—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen with oxygen-generating compounds, e.g. per-compounds, chromic acid, chromates
    • 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
    • C10G27/00—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation
    • C10G27/04—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen
    • 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
    • C10G53/00—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes
    • C10G53/02—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only
    • C10G53/14—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only including at least one oxidation step

Definitions

  • the oxidant gas may be 11641546 1/1965 208/36 regenerated by the addition of oxygen and recircu- 2,976,229 3/1961 Brown et al. 208/2 lated.
  • Harder et al 208/276 may be decomposed hydlolysls reacuo 3,294,677 12/1966 Martin et almn 208/224 lute base to separate inorganic sulfate and sulfite, and
  • Prior Art The presently used methodfor performing the function of the present invention involves the useof a high temperature-high pressure process to desulfurize hydrocarbon fuels using hydrogen, and an acid extractionprocess for the removal of basic nitrogen compounds.
  • the old methods have major disadvantages.
  • Hydrogen is a valuable material, made in refineries by pyrolyzing (heating to decompose) l hydrocarbon materials or through combustion to form carbon monoxide which is subsequently reacted catalytically with water athigh temperature. In any case, it is costly to use hydrogen to remove sulfur (as-hydrogen sulfide) from fuels.
  • the reaction of hydrogen is nonselective in that some of the hydrogen will react with-the oil to saturate hydrocarbon molecules (aromatics, olefins) in addition to the desired reactionforminghydrogen sulfide. This means that a large quantity of hydrogen is required to.desul-' furize hydrocarbon fuels.
  • the second disadvantage of the present method for sulfur removal is that it requires a heterogeneous catalyst.
  • the surface of the solid catalyst tends to become fouled, particularly when residual oils are desulfurized, and this makes the oldmethod inefficient or inoperable with some residual fuels.
  • the third disadvantage of the present method'for sulfur removal is that it requires high temperatures and high pressures for desulfurizing fuels.
  • the reaction conditions make it necessary to use expensive equipment for the old process.
  • U.S. Pat. No. 1,968,842 issued to Malisoff proposes to treat the sulfur containing oil with a solution of an alkali in an organic solvent.
  • the alkali reacts with mercaptans in the oil forming sulfur compounds which are more'soluble in the solvent than in the oil.
  • the Malisoff patent is directed specifically to sulfur in the form of mercaptansin the oil and does not deal in any way with the broad range of sulfur and nitrogen compounds susceptible to the method of the present invention.
  • U.S. Pat. No. 3,267,027 issued to Fierce discloses reacting light petroleum distillates with N followed by washing with an aqueous caustic and finally a water wash. The temperature of the reaction is limited to C.
  • This process also is directed primarily to the removal of mercaptans and thus also has limited applicabilit S weetening" of petroleum oils has also been known to applicant as having been proposed by several people, and is a related process. While not considered directly applicable, the most pertinent of these is U.S. Pat. No. 3,224,618 issued to Dimond. Again, the process considers only mercaptans and proposes to convert any mercaptans present in hydrocarbons to disulfrdes by 2]. reacting the mercaptansywith:oxygen'in the presence of an oxide of nitrogen. Theresulting disulfides are not as odorous as the mercaptans and thus the treated oil is considered sweet.
  • the major disadvantage of the old method for nitrogen removal is that it achievesonly partial nitrogen removal. Specifically, it removes only some of the basic nitrogen compounds.
  • thegeneral purpose of the present invention is to provide such'a low cost process.
  • the process is low cost since it is carried out at low pressures and temperatures, that is, the process equipment is inexpensive compared to the equipment required for high pressure, high temperature processes. Further, the process uses only lowcost chemicals (i.-e., oxygen, nitrogen oxides an-methanol, the latter two being recycled) to remove substantially all of the sulfur and nitrogen from the fuels.
  • the process has broad applicability since it can be .used .to'treatliquid petroleum distillates (diesel oil, jet fuel) as well as residual oils.
  • the process makes it possible to upgrade hydrocarbon fractions from initially low value-high sulfur and nitrogen materials to produce'high value-low sulfur and nitrogen materials for use particularly as fuels.
  • the process signifi cantly' increases the quantity of fossil fuels available to use within the current air pollution regulations and makes possible a large future. reduction in the oxidesof sulfur and oxides of nitrogen emissions by fuel users.
  • the present invention is a process based on the selective oxidation of the sulfur and nitrogen compounds in liquid petroleum oil.
  • Petroleum oil is used herein to signify diesel oil, jet fuel, furnace oil, residual oil, crude oil, topped crude oil, and similar hydrocarbon mixtures.
  • Oxygen is used to regenerate the gas phase oxidizers (oxides of nitrogen containing two or more oxygen atoms, e.g., N0 which are recycled.
  • the process can be carried out batch-wise or continuously as desired.
  • a batch of oil can be placed in a vessel and treated with the gas phase.
  • oxidizer to oxidize the sulfur and nitrogen compounds or the oil can be continuously pumped through a-reactor in which the oxidation is accomplished.
  • the oxidizing gas may be passed upward through a vessel while the oil passes downward.
  • the vessel maybe packed with a material (like Berl saddles) which permits the two flows to occur without interference or a large pressure drop.
  • the reacted oil is extracted with a suitable solvent to separate the oxidized sulfur and nitrogen compounds.
  • the extraction can also be carried out continuously or batch-wise. Atthis point, a major fraction of the oil has low sulfur and nitrogen content and is solvent stripped and removed from the process for use.
  • One difficulty which may occur in this process is that some oils may tend to react non selectively during the oxidation step and form undesirable polymers and coke. This problem may be obviated by preheating the feed oil to 300 to 600 F for some time, typically 2 to 20 hours to permit the reactive groups in the oil to combine with parts of the other hydrocarbon molecules and thus become less active.
  • An alternate pretreatment procedure is to react the oil with a reactant such as water, hydrogen, or ammonia to remove the active groups in the oil.
  • the solvent containing dissolved sulfur and nitrogen compound and a fraction of dissolved oil can be separated from its solute either by evaporating the solvent or cooling the mixture to a temperature where the oxidized sulfur and nitrogen compounds have low solubility.
  • the solvent is then recycled through the process.
  • the sulfur and nitrogen may be separated from the solute, for example, by hydrolysis or pyrolysis.
  • the process consumes oxygen and energy and produces a low sulfur, low nitrogen oil having physical properties similar to the feed, a lighter oil fraction (from the solute) and inorganic sulfur as sulfite or sulfate ions and inorganic nitrogen as nitrate and nitrite ions or nitrogen.
  • the process steps are all carried out at near ambient pressure and temperatures below about 300 F so the equipment, tanks, piping, etc., are all inexpensive compared to those needed for a high temperature, high pressure process.
  • FIG. I is a block diagram of the process of the present invention.
  • FIG. 2 is a block diagram of the oxidizing gas recirculating system.
  • FIG. 3 is a block diagram of a first pretreatment step.
  • FIG. 4 is a block diagram of an alternative pretreatment step.
  • Disulfides while not having the objectionable odor of mercaptans, are, unfortunately, not easily separated from the oil and thus the oxidation step contemplated by the method of this invention is intended to oxidize the sulfur compounds into a higher state which exhibits low solubility in oil, but relatively good solubility in some other solvent so that the compounds can be subsequently removed by the process of preferential solubilit 2.
  • a suitable solvent such as methanol, which is immiscible with the oil, but in which the oxidized sulfur and nitrogen compounds readily dissolve.
  • Methanol is not the only possible solvent, but is presently preferred since it embodies the characteristics desired in a suitable solvent. The desired characteristics are as follows:
  • the different densities of the oil and the solvent allow separation of the oil (with reduced sulfur and nitrogen content) from the solvent (in which the sulfur and nitrogen compounds are dissolved) by gravitational settling or centrifuging.
  • the resulting oil has a low sulfur and nitrogen content as is necessary to meet the present stringent requirements for fuels.
  • pretreatment of the oil in some circumstances.
  • one difficulty which may occur in the process is that some oils may tend to react non selectively during the oxidation step and form undesirable polymers and coke.
  • This problem is obviated by preheating the feed oil to 300 to 600 F for some time, typically 2 to 20 hours to permit the reactive groups in the oil to combine with parts of the other hydrocarbon molecules and thus become less active.
  • An alternate pretreatment procedure is to react the oil with a reactant such as water, hydrogen, or ammonia to remove the active groups in the oil.
  • oils which have a high volatility portion can be topped at temperatures up to 800F, at atmospheric pressure, or 1,000F., in vacuum, before processing.
  • the high volatility portion of the oil is low in sulfur.
  • oils having a methanol soluble portion can be treated with methanol first to separate the methanol soluble portion.
  • FIG. 1 a block diagram of one preferred embodiment of the process of this invention is shown in the form of a continuous process.
  • the process can also be a combination of batch and continuous, for example, the pretreatment steps, if utilized, can be done batch-wise while the remainder of the process is continuous. Other combinations of batch and continuous processing are also possible and practical within the spirit of the present invention.
  • the process, as illustrated in FIG. 1, does not include any pretreatment steps, it being assumed that such steps are either unnecessary or already performed on the particular oil being processed.
  • the reactor preferably operates at near atmospheric pressure since this results in simple and relatively inexpensive processing equipment. No particular advantage is to be gained by increasing the pressure of the system, butto some extent a somewhat higher than room temperature can be of advantage. A higher temperature will tend to cause the reaction in which mercaptans become disulfides to proceed further converting the disulfides into sulfoxides. Typical temperatures which are desirable range from about 50 to 350 F. As the temperature increases some undesirable side reactions such as polymerization and coke formation begin to occur. The process temperature should not be so high nor the time of application so long that these side reactions become a problem.
  • the reactor is the vessel which provides contact between the feed oil and the oxidizing gas allowing the reaction to take place. It can take many forms, but in the particular embodiment being described, is a relatively tall cylindrical vessel in which the oil is introduced at the top and the oxidizing gas at the bottom. The oil flows downward due to gravity, flowing over baffles, or other packing which provide a large surface over which the oil can flow. The oil flows in thin layers so that a large surface of oil is presented to the oxidizing gas.
  • a typical reactor 11 may be packed with Berl saddles 12, which occupy about 50 percent of the reactor volume, leaving open spaces through which the oxidizing gas can pass in contact with the oil on the surface of the saddles.
  • reactors to obtain intimate contact between the oil and oxidizing gas may, of course, be used, for example, agitated vessels.
  • the volume of the reactor is a function of the volumetric flow rate of the oil and usually ranges from about 10 to 100 times the hourly oil flow rate.
  • the flow of oil is such that the flowing oil remains in the reactor for up to about minutes at temperatures up to about 350 F., the time and temperature being enough to allow the sulfur and nitrogen compounds in the oil to oxidize as needed to form the compounds which will preferentially dissolve in the solvent used, but not so hot or so long as to cause polymerization or side reactions.
  • the use of too high a temperature tends to cause polymerization of the oil and is thus not desirable, while overlong exposure to the oxidant allows other unwanted side reactions to occur which are also undesirable.
  • the oxidizing gas is comprised of oxides of nitrogen. It can be a single oxide, or a mixture of nitrogen oxides.
  • the oxides which have been found to be useful are N0 N 0 N 0 and N 0
  • a preferred composition of oxidizing gas is l to 9 percent by volume NO N0 1 to 19 percent by volume 0 with the balance N
  • the oxidizing gas is introduced at inlet l3 located near the bottom of the reactor and flows upward through the reactor contacting the oil which is flowing over the surfaces of the Berl saddles 12.
  • the oxidizer flows out through outlet 14. It will be found to be most economical to reconstitute the oxidizer and continuously recycle the gas through the reactor. The procedure for accomplishing this will be discussed below.
  • organic nitrogen compounds present in the oil having one or more carbon bonds e.g., amines, saturated aliphatic compounds or parts of an aromatic ring
  • Typical reactions could be as follows:
  • RN NO R N N0 R NO NO The oxidized compounds formed are soluble in methanol and are thus susceptible to removal from the oil in the process as described below.
  • the oil containing the oxidized sulfur and nitrogen compounds flows out of the bottom of reactor 11 and is pumped by pump 19 to mixer 20 where it is mixed with a solvent, which is preferably methanol, pumped into mixer 20 by pump 21 from solvent storage tank 22.
  • a solvent which is preferably methanol
  • a quantity of solvent about 1 to 5 times the volume of oil insures that substantially all of the soluble components in the oil dissolve in the solvent.
  • the solvent must be selective, that is, one in which the oxidized sulfur and nitrogen compounds are soluble but in which the oil itself is not soluble.
  • Methanol is the presently preferred solvent but other solvents such as methanolwater mixtures, methanol-ethanol-water mixtures, and methanol-inorganic salt (e.g., sodium chloride, potassium chloride and calcium chloride) solutions can be used.
  • the mixer may be a stirred vessel or simply a static mixer in which the flow streamlines are broken up by the shape of the vessel or by obtructions therein. Again the mixing may be done at atmospheric pressure. and the temperature is not criticalbut is preferably between 80 and F, the upper temperature limit being the boiling point of solvent.
  • the mixture flows to separator 23 where the fluid is brought essentially to rest andthe lighter liquid, which in the case of a methanol-diesel oil system is the methanol, rises to the top and the oil sinks to the bottom.
  • the desulfurized and denitrogenated oil flows out of a bottom tap 24 of separator 23 while the solvent carrying the oxidized sulfur and nitrogen compounds in solution is decanted from tap 25 at the top of separator 23.
  • the separator is preferably maintained at 1 atmosphere pressure and between 80 and 150 F., neither condition being critical. Separation of the fluids occurs in about to 30 minutes and a separator vessel with sufficient volume to hold 10 to 30 minutes of flow would be satisfactory.
  • a continuous flow from taps 24 and 25, keeping the line of demarcation between the oil and the methanol solution about in the middle of the vessel allows the separation to take place and prevents contamination of the separator output streams.
  • any residual solvent remaining in the oil leaving tap 24 is removed in holding tank 26 which is maintained at a relatively high temperature, for example, 160 F which causes the solvent to vaporize.
  • the vaporized solvent flows to condenser 27 where it is condensed and is then added to the solvent in solvent tank 22.
  • the solvent stream including the dissolved sulfur and nitrogen compounds, as well as a small fraction of oil (generally 2 to 5 percent of the initial oil volume), flows from separator 23 through outlet 25 to the solvent still 29, which is maintained at a high enough temperature to evaporate the solvent.
  • the solvent vapor is condensed in condenser 27 and the distilled liquid solvent then flows to tank 22 for recycling.
  • the residue of the solvent distillation, containing sulfur and nitrogen compounds, oil, and some amount of solvent is passed through a holding tank 30, maintained at over the boiling point of the solvent, where the last vestiges of solvent are stripped from the liquid and recovered in condenser 27.
  • the high sulfur, high nitrogen oil remaining as the residue can either be used as is, for applications where the high sulfur and nitrogen content is unimportant, or the oil can be further processed in decomposer 31 which subjects the oil to a pressure of l to 5 atmospheres at 150 to 300 F for 5 to 30 minutes in the presence of air and a dilute inorganic base such as sodium hydroxide.
  • decomposer 31 which subjects the oil to a pressure of l to 5 atmospheres at 150 to 300 F for 5 to 30 minutes in the presence of air and a dilute inorganic base such as sodium hydroxide.
  • the ensuing hydrolysis reaction decomposes the oxidized sulfur and nitrogen compounds forming hydrocarbons and sulfite or sulfate compounds and nitrite or nitrate compounds.
  • FIG. 2 shows how this may be accomplished.
  • the reaction in the reactor reduces the N0 to NO while oxidizing the sulfur and nitrogen compounds in the oil.
  • the reaction in the reactor reduces the N0 to NO while oxidizing the sulfur and nitrogen compounds in the oil.
  • the reaction of NO and 0 present to maintain an equilibrium of N0 NO, and 0 as follows:
  • makeup gas is NO and 0 which are reacted as will be presently described to form N0
  • the oxidizing and makeup gases may be any one or more of the higher oxides of nitrogen previously mentioned and in such case it would not be necessary to provide the NO reacting means.
  • Pump 17 circulates the oxidizer in the system.
  • the rate of circulation is not critical, the most desirable rate depending on the temperature of the reactor, the quality of the contact of the oxidant with the oil and the length of time the oil is in contact with the gas.
  • the order of magnitude of the circulation is 10 to 20 moles of oxygen per mole of sulfur and nitrogen removed.
  • NO reactor 18 is a heated vessel maintained at 200 to 450 F. in which the NO and O react forming N0 so that the gas stream entering reactor 11 will be rich in N0 the primary oxidant.
  • NO reactor 18 is preferably of a size which allows the gas to remain in it for l to 3 minutes in order that the desired reaction take place.
  • the gas having the desired composition After leaving NO reactor 18, the gas having the desired composition enters reactor 11 through inlet 13. After exiting through outlet 14, the gas is fed through oil trap 33 and filter 34 before any portion of the gas is vented through bleed 35.
  • the purpose of these units is to help clean up the circulating gas and to prevent oil vapors or solid particles from being vented to the atmosphere. It may be necessary in order to comply with anti-pollution statutes, to further treat the bleed stream 35 before allowing it to escape to the atmosphere.
  • Some oils may tend to react non selectively during the oxidation step and form undesirable polymers and coke.
  • a pretreatment as illustrated in FIGS. 3 or 4 might be found advantageous.
  • a pump 43 drives oil from a reservoir or other source, not shown, into prereactor 40.
  • the prereactor 40 is maintained at an elevated temperature of 300 to 600 F and is of sufficient size to that oil will remain in the prereactor for from 2 to 20 hours.
  • reactive groupsin the oil combine with parts of other hydrocarbon molecules and become less active.
  • the purpose of this step is to reduce undesirable side reactions in the oxidation step which follows. Active groups in the oil, unless disposed of in some manner, may tend to react nonselectively in the oxidation reactor to form undesirable polymers and coke. By pretreating the oil to reduce the activity of these groups, the side reactions can be held to a minimum.
  • FIG. 4 An alternate pretreatment is illustrated in FIG. 4 where that portion of the apparatus used in the pre treatment step only is shown.
  • a pump 41 pumps a suitable reactant, such as water, hydrogen, or ammonia, into prereactor 42.
  • a suitable reactant such as water, hydrogen, or ammonia
  • Prereactor 42 need not be heated but agitation means, not shown, should be supplied to insure good mixing of the feed oil and the reactant.
  • the reactant reacts with the active groups in the feed oil thereby reducing the amount of active material in the oil.
  • topping oils which have a high volatility portion by heating the feed oil to 800 F at atmospheric pressure or 1,000 F in vacuum.
  • the high volatility portion of oil is low in sulfur and removing such portion before processing will increase the efficiency of the process.
  • An oil which contains a methanol solubleportion can be treated with methanol first to separate the soluble portion.
  • the oil is fed to reactor 11 and processed in the manner previously described.
  • Table II the results for a variety of residual oils show that the method removes sulfur and nitrogen from thqssfys s- In treating the high sulfur oil remaining from the residue in Test 41-1 at 250F and one atmosphere for minutes using an equal-volume of 10 percent sodium hydroxide in water with air passingthrough the oil at,
  • Thetreatin g gas was prepared by mixing air and nitrogen oxide (NOT and heating the mix ture to 250F RESIDUAL OIL TESTS Process Conditions Initial Oxidation Oxidizer Extraction Sample Type of Oil Wt. S,Wt. N Time Temp. Conc. Vol. Solv/ Final Removal F Vol.% NO Vol. Oil Wt. S Wt. N S N Batch Reactor Tests lg u ur 2.2 3 hrs. 225 I0 4 1.8 14
US00385894A 1973-08-06 1973-08-06 Method for removing sulfur and nitrogen in petroleum oils Expired - Lifetime US3847800A (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
US00385894A US3847800A (en) 1973-08-06 1973-08-06 Method for removing sulfur and nitrogen in petroleum oils
GB2156674A GB1437569A (en) 1973-08-06 1974-05-15 Method for removing sulphur and nitrogen in petroleum oils
DE2424274A DE2424274C3 (de) 1973-08-06 1974-05-18 Verfahren zur Reduzierung des Gehaltes von Schwefel- und Stickstoffverbindungen in Erdölkohlenwasserstoffgemischen
CA200,763A CA1046004A (en) 1973-08-06 1974-05-24 Method for removing sulfur and nitrogen in petroleum oils
NL7407257A NL7407257A (nl) 1973-08-06 1974-05-30 Werkwijze voor het verwijderen van zwavel en stikstof uit oliefrakties en de inrichting voor het uitvoeren van deze werkwijze.
IN1365/CAL/74A IN141762B (xx) 1973-08-06 1974-06-20
JP7863974A JPS5337081B2 (xx) 1973-08-06 1974-07-09
IE1506/74A IE39619B1 (en) 1973-08-06 1974-07-16 Method for removing sulfur and nitrogen in petroleum oils
AU71509/74A AU492349B2 (en) 1974-07-22 method FOR REMOVING SULFUR AND NITROGEN PETROLEUM OILS
FR7425960A FR2240280B1 (xx) 1973-08-06 1974-07-25
SU2049070A SU508220A3 (ru) 1973-08-06 1974-07-26 Способ очистки нефти и нефт ных фракций от серу-и азотсодержащих соединений
BE147170A BE818350A (fr) 1973-08-06 1974-07-31 Procede pour reduire les concentrations en composes soufres et azotes dans une huile de petrole
BR6369/74A BR7406369D0 (pt) 1973-08-06 1974-08-02 Processo para reduzir as concentracoes de compostos de enxofre e nitrogenio em oleos de petroleo
IT26012/74A IT1017927B (it) 1973-08-06 1974-08-06 Metodo per eliminare zolfo ed azoto da oli di petrolio

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JP (1) JPS5337081B2 (xx)
BE (1) BE818350A (xx)
BR (1) BR7406369D0 (xx)
CA (1) CA1046004A (xx)
DE (1) DE2424274C3 (xx)
FR (1) FR2240280B1 (xx)
GB (1) GB1437569A (xx)
IE (1) IE39619B1 (xx)
IN (1) IN141762B (xx)
IT (1) IT1017927B (xx)
NL (1) NL7407257A (xx)
SU (1) SU508220A3 (xx)

Cited By (36)

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US3919402A (en) * 1973-08-06 1975-11-11 Kvb Inc Petroleum oil desulfurization process
US4382855A (en) * 1981-10-28 1983-05-10 Ashland Oil, Inc. Process for removal of hydroxy- and/or mercapto-substituted hydrocarbons from coal liquids
EP0097055A2 (en) * 1982-06-15 1983-12-28 REI Technologies Inc. Process for purifying hydrocarbonaceous oils
US4643820A (en) * 1986-02-24 1987-02-17 Oxiprocessing Process for enhancing the cetane number of diesel fuel
EP0234878A2 (en) * 1986-02-24 1987-09-02 ENSR Corporation (a Delaware Corporation) Process for upgrading diesel oils
US4711713A (en) * 1986-02-24 1987-12-08 Rei Technologies, Inc. Process for enhancing the cetane number and color of diesel fuel
US4743360A (en) * 1985-10-24 1988-05-10 Labofina, S.A. Process for removing basic nitrogen compounds from gas oils
FR2657620A1 (fr) * 1990-01-30 1991-08-02 Elf France Procede de stabilisation de gazoles issus de craquage catalytique, gazole ainsi obtenu et compositions renfermant ledit gazole stabilise.
CN1062294C (zh) * 1995-09-05 2001-02-21 新疆石油管理局克拉玛依炼油厂 一种石油馏份油氨醇脱酸工艺
US6368495B1 (en) * 1999-06-07 2002-04-09 Uop Llc Removal of sulfur-containing compounds from liquid hydrocarbon streams
US20020148754A1 (en) * 2001-02-08 2002-10-17 Gong William H. Integrated preparation of blending components for refinery transportation fuels
US20020148756A1 (en) * 2001-02-08 2002-10-17 Morris George Ernest Preparation of components for transportation fuels
US20020152673A1 (en) * 2001-02-08 2002-10-24 Huff George A. Transportation fuels
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US20110220550A1 (en) * 2010-03-15 2011-09-15 Abdennour Bourane Mild hydrodesulfurization integrating targeted oxidative desulfurization to produce diesel fuel having an ultra-low level of organosulfur compounds
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US6838060B1 (en) * 1996-09-24 2005-01-04 Institut Francais Dupetrole Process and apparatus for the production of catalytic cracking gasoline with a low sulphur content
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US6544409B2 (en) 2001-05-16 2003-04-08 Petroleo Brasileiro S.A. - Petrobras Process for the catalytic oxidation of sulfur, nitrogen and unsaturated compounds from hydrocarbon streams
US20040108252A1 (en) * 2002-12-10 2004-06-10 Petroleo Brasileiro S.A. - Petrobras Process for the upgrading of raw hydrocarbon streams
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US20040222134A1 (en) * 2003-05-06 2004-11-11 Petroleo Brasileiro S.A. - Petrobras Process for the extractive oxidation of contaminants from raw hydrocarbon streams
US7175755B2 (en) 2003-05-06 2007-02-13 Petroleo Brasileiro S.A.-Petrobras Process for the extractive oxidation of contaminants from raw hydrocarbon streams
US20100025301A1 (en) * 2004-05-31 2010-02-04 Agency For Science, Technology And Research Novel process for removing sulfur from fuels
US8016999B2 (en) 2004-05-31 2011-09-13 Agency For Science, Technology And Research Process for removing sulfur from fuels
US20070227951A1 (en) * 2004-05-31 2007-10-04 Jeyagorwy Thirugnanasampanthar Novel Process for Removing Sulfur from Fuels
US20060131214A1 (en) * 2004-12-21 2006-06-22 Petroleo Brasileiro S.A. - Petrobras Process for the extractive oxidation of contaminants from raw fuel streams catalyzed by iron oxides
EP1674158A1 (en) 2004-12-21 2006-06-28 Petroleo Brasileiro S.A. - PETROBAS A process for the extractive oxidation of contaminants from raw fuel streams catalyzed by iron oxides
US7803270B2 (en) 2004-12-21 2010-09-28 Petroleo Brasileiro S.A. - Petrobras Process for the extractive oxidation of contaminants from raw fuel streams catalyzed by iron oxides
US9023120B2 (en) * 2009-06-19 2015-05-05 Cyuba Enzyme Ltd. Fuel production method, fuel production apparatus, and fuel oil
US20100319241A1 (en) * 2009-06-19 2010-12-23 Cyubu Enzyme Ltd. Fuel production method, fuel production apparatus, and fuel oil
KR101042093B1 (ko) 2009-06-19 2011-06-16 유겐가이샤 추부엔자임 연료 제조 방법 및 연료 제조 장치
US20110220550A1 (en) * 2010-03-15 2011-09-15 Abdennour Bourane Mild hydrodesulfurization integrating targeted oxidative desulfurization to produce diesel fuel having an ultra-low level of organosulfur compounds
US20110220547A1 (en) * 2010-03-15 2011-09-15 Abdennour Bourane Targeted desulfurization process and apparatus integrating oxidative desulfurization and hydrodesulfurization to produce diesel fuel having an ultra-low level of organosulfur compounds
US9644156B2 (en) 2010-03-15 2017-05-09 Saudi Arabian Oil Company Targeted desulfurization apparatus integrating oxidative desulfurization and hydrodesulfurization to produce diesel fuel having an ultra-low level of organosulfur compounds
US9296960B2 (en) 2010-03-15 2016-03-29 Saudi Arabian Oil Company Targeted desulfurization process and apparatus integrating oxidative desulfurization and hydrodesulfurization to produce diesel fuel having an ultra-low level of organosulfur compounds
US20110233110A1 (en) * 2010-03-29 2011-09-29 Omer Refa Koseoglu Integrated hydrotreating and oxidative desulfurization process
US9464241B2 (en) 2010-03-29 2016-10-11 Saudi Arabian Oil Company Hydrotreating unit with integrated oxidative desulfurization
US8658027B2 (en) 2010-03-29 2014-02-25 Saudi Arabian Oil Company Integrated hydrotreating and oxidative desulfurization process
US9290712B2 (en) 2010-09-03 2016-03-22 Her Majesty The Queen In Right Of Canada As Represented By The Minister Of Natural Resources Canada Production of high-cetane diesel product
US9873797B2 (en) 2011-10-24 2018-01-23 Aditya Birla Nuvo Limited Process for the production of carbon black
US8906227B2 (en) 2012-02-02 2014-12-09 Suadi Arabian Oil Company Mild hydrodesulfurization integrating gas phase catalytic oxidation to produce fuels having an ultra-low level of organosulfur compounds
US9410042B2 (en) 2012-03-30 2016-08-09 Aditya Birla Science And Technology Company Ltd. Process for obtaining carbon black powder with reduced sulfur content
CN104919025B (zh) * 2012-11-09 2017-07-28 沙特阿拉伯石油公司 氧化性脱硫方法和使用气态氧化剂增强的进料的系统
CN104919025A (zh) * 2012-11-09 2015-09-16 沙特阿拉伯石油公司 氧化性脱硫方法和使用气态氧化剂增强的进料的系统
WO2014074958A1 (en) * 2012-11-09 2014-05-15 Saudi Arabian Oil Company Oxidative desulfurization process and system using gaseous oxidant-enhanced feed
KR20150105946A (ko) * 2012-11-09 2015-09-18 사우디 아라비안 오일 컴퍼니 가스 산화제-강화 피드를 이용한 산화 탈황 공정 및 시스템
US9719029B2 (en) 2012-11-09 2017-08-01 Saudi Arabian Oil Company Oxidative desulfurization process and system using gaseous oxidant-enhanced feed
KR102187212B1 (ko) 2012-11-09 2020-12-04 사우디 아라비안 오일 컴퍼니 가스 산화제-강화 피드를 이용한 산화 탈황 공정 및 시스템
US8920635B2 (en) 2013-01-14 2014-12-30 Saudi Arabian Oil Company Targeted desulfurization process and apparatus integrating gas phase oxidative desulfurization and hydrodesulfurization to produce diesel fuel having an ultra-low level of organosulfur compounds
CN108239556A (zh) * 2016-12-23 2018-07-03 中国石油天然气股份有限公司 一种分离富集焦化蜡油中碱性及非碱性氮化物的方法
CN108239556B (zh) * 2016-12-23 2020-08-07 中国石油天然气股份有限公司 一种分离富集焦化蜡油中碱性及非碱性氮化物的方法
CN108795483A (zh) * 2017-05-02 2018-11-13 中国石油天然气股份有限公司 一种分离和精制石油馏分中非碱性含氮化合物的方法

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BE818350A (fr) 1974-11-18
DE2424274C3 (de) 1979-10-18
NL7407257A (nl) 1975-02-10
FR2240280B1 (xx) 1979-02-16
SU508220A3 (ru) 1976-03-25
GB1437569A (en) 1976-05-26
IN141762B (xx) 1977-04-16
IE39619B1 (en) 1978-11-22
JPS5039704A (xx) 1975-04-12
DE2424274B2 (de) 1979-03-01
FR2240280A1 (xx) 1975-03-07
JPS5337081B2 (xx) 1978-10-06
CA1046004A (en) 1979-01-09

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