Nitrogen Contaminant Removal Patents (Class 208/254R)
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Patent number: 6162350Abstract: Hydroprocessing of petroleum and chemical feedstocks using bulk Group VIII/Group VIB catalysts. Preferred catalysts include those comprised of Ni--Mo--W.Type: GrantFiled: January 15, 1999Date of Patent: December 19, 2000Assignee: Exxon Research and Engineering CompanyInventors: Stuart L. Soled, Kenneth L. Riley, Gary P. Schleicher
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Patent number: 6160193Abstract: A method for the removal of sulfur and nitrogen containing compounds from petroleum distillates. Sulfur- and nitrogen-containing compounds are oxidized using a selective oxidant to create compounds that can be preferentially extracted from a petroleum distillate due to their increased relative polarity. Oxidation is accomplished by contacting an oxidant with a distillate under optimum conditions for that distillate and continuing the reaction until oxidized sulfur- and nitrogen-containing compounds are confirmed. Extraction is accomplished by contacting oxidized distillate with a non-miscible solvent that is selective for the relatively polar oxidized sulfur- and nitrogen-containing compounds. The oxidized compounds and solvent are separated from the distillate by gravity separation or centrifugation. The distillate is water washed and polished using clay filtration. The extraction solvent is separated from the solvent/oxidized compound mixture by a simple distillation for recycling.Type: GrantFiled: November 23, 1998Date of Patent: December 12, 2000Inventor: Walter Gore
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Patent number: 6107535Abstract: A process for selectively removing nitrogenated and/or sulfurated contaminants from streams prevalently containing hydrocarbons with from 3 to 8 crbon atoms characterized in that it comprises an adsorption step wherein said contaminants are adsorbed by an adsorbent essentially consisting of silica gel at a temperature of between 0 and 150.degree. C. and at a pressure of between 1 and 20 atm and a regeneration step to remove the adsorbed substances by thermal treatment in a stream of insert gas carried out at a temperature of between 100 and 200.degree. C.Type: GrantFiled: October 21, 1998Date of Patent: August 22, 2000Assignee: Snamprogette S.p.A.Inventors: Stefano Rossini, Valerio Piccoli
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Patent number: 6096195Abstract: Described in a process for hydrotreating (HDT) a petroleum feedstock (1) that contains sulfur and nitrogen are the catalytic cracking of the ammonia, produced by the hydrotreating process, in a catalytic cracking furnace (F), the cooling (E2) and separating of the cracking effluent to produce an H.sub.2 S containing gas phase, the extraction of the hydrogen sulfide from said gas phase and from the hydrotreating purge gas in an amine washing unit (20), and the separation (SM) of the hydrogen from the resultant effluent. The recovered hydrogen is recycled to hydrotreating unit (HDT) via a pipe (17).Type: GrantFiled: August 24, 1998Date of Patent: August 1, 2000Assignee: Institut Francais du PetroleInventors: Christian Streicher, Fabrice Lecomte, Christian Busson
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Patent number: 6019887Abstract: An adsorption/desorption process for selectively removing nitriles from a hydrocarbon feedstock includes the steps of: (a) providing a hydrocarbon feedstock having a nitrile content of less than or equal to about 400 ppm; (b) providing an adsorbent for selective removal of nitrile from a hydrocarbon feedstock comprising a substantially homogeneous mixture of a cationic nonacidic zeolite and an inorganic oxide matrix, the zeolite having an accessibility index of between about 0.1 to about 0.4; (c) contacting the feedstock and the adsorbent at nitrile adsorption conditions whereby at least about 80% of the nitrile content is adsorbed by the adsorbent during contact with at least about 200 volumes of the feedstock per volume of the adsorbent so as to provide a used adsorbent having nitrile molecules adsorbed thereon; and (d) contacting the used adsorbent with a desorbent at desorption conditions so as to remove the nitrile molecules and provide a renewed adsorbent.Type: GrantFiled: November 19, 1998Date of Patent: February 1, 2000Assignee: Intevep, S.A.Inventors: Maria M. Ramirez de Agudelo, Julia T. Guerra, Douglaines L Marcano, Zaida Hernandez
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Patent number: 5976359Abstract: Disclosed is a method for reducing the concentration of amines in hydrocarbon fluids and process streams by generating therein a nitrosating agent. The nitrosating agent will react with the amines to form innocuous by-products under refinery process conditions.Type: GrantFiled: May 15, 1998Date of Patent: November 2, 1999Assignee: BetzDearborn Inc.Inventor: Wiley L. Parker
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Patent number: 5955045Abstract: For selectively removing nitrogen oxides from a carrier gas that contains hydrocarbons, the nitrogen oxides are removed by chemisorption on metal oxides, without the occurrence of undesirable secondary reactions. The metal oxides are preferably formed from metals of the 6th to 8th subgroups, whereby manganese dioxide (MnO.sub.2,) is especially preferred as a metal oxide. The process can be conducted with one or more reactor beds, which preferably operate at 10 to 40.degree. C. and are regenerated with nitrogen at a temperature of 130 to 170.degree. C.By removing nitrogen oxides from an olefin-rich gas, for example from the waste gas of an FCC unit, the resultant gas can then be fed to a cryogenic olefin extraction stage without danger of explosion.Such a waste gas contains unsaturated hydrocarbons, hydrogen, carbon monoxide, and oxygen, the oxygen having a concentration preferably between 100 and 5000 mol ppm.Type: GrantFiled: June 13, 1997Date of Patent: September 21, 1999Assignee: Linde AktiengesellschaftInventors: Karl Baur, Hans-Peter Langebach, Hartmut Neumann, Ulrike Wenning
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Patent number: 5858211Abstract: An adsorbent for selective removal of nitrile from a hydrocarbon feedstock includes a substantially homogeneous mixture of a cationic nonacidic zeolite and an inorganic oxide matrix, the zeolite having an accessibility index of between about 0.1 to about 0.4, and the adsorbent being capable, when contacted with a hydrocarbon feedstock containing nitrile and containing dienes in an amount of at least about 1.0% by volume, of adsorbing at least about 80% of the nitrile during contact with at least about 200 volumes of the feedstock per volume of adsorbent.Type: GrantFiled: June 15, 1998Date of Patent: January 12, 1999Assignee: Intevep, S.A.Inventors: Maria Magdalena Ramirez de Agudelo, Julia Guerra, Marisela Gonzalez
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Patent number: 5817229Abstract: A hydrocarbon feedstock is brought into contact with activated carbon at a temperature of about 300.degree. to about 650.degree. C. and a pressure of about 0-1000 psig in the absence of added hydrogen to reduce the content of aromatic, sulfur and nitrogen compounds contained therein and to simultaneously lower the specific gravity thereof.Type: GrantFiled: November 6, 1996Date of Patent: October 6, 1998Assignee: Texaco IncInventors: Chakka Sudhakar, Regis J. Pellet, Mahendra Somabhai Patel
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Patent number: 5770047Abstract: A process for upgrading a nitrogen and sulfur rich heavy naphtha feedstock includes the steps of providing a naphtha feedstock having an initial nitrogen content, an initial sulfur content and an initial octane number; contacting the naphtha feedstock with an acid source so as to provide a reduced nitrogen feedstock having a reduced nitrogen content which is less than the initial nitrogen content; contacting the reduced nitrogen feedstock with a hydroconversion catalyst system under a hydrogen atmosphere, temperature and pressure so as to provide a final product having a final nitrogen content which is less than the initial nitrogen content, a final sulfur content which is less than the initial sulfur content, and having a final octane number which is substantially equal to or greater than the initial octane number of the feedstock, and wherein the final product has an increased isomerized component and substantially no increase in aromatic content with respect to the feedstock.Type: GrantFiled: June 11, 1996Date of Patent: June 23, 1998Assignee: Intevep, S.A.Inventors: Jose Armando Salazar, Luis M. Cabrera, Eusebio Palmisano, Wolfgang J. Garcia, Rodolfo Bruno Solari
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Patent number: 5744686Abstract: This invention relates to a process for the removal of nitrogen compounds from an aromatic hydrocarbon stream comprising the nitrogen compounds by contacting the hydrocarbon stream with a selective adsorbent having an average pore size less than. about 5.5 Angstroms. The selective adsorbent is a molecular sieve selected from the group consisting of pore closed zeolite 4A, zeolite 4A, zeolite 5A, silicalite, F-silicalite, ZSM-5 and mixtures thereof. In one embodiment, the present invention comprises a combination of a fractionation zone and an adsorption zone wherein the feedstream is passed to the fractionation zone to provide a dry bottoms product stream essentially free of the nitrogen compounds and an overhead stream. The overhead stream is condensed to provide an aqueous stream and a hydrocarbon stream. The hydrocarbon stream is passed to an adsorption zone and a treated effluent recovered therefrom is returned to the fractionation zone.Type: GrantFiled: September 20, 1995Date of Patent: April 28, 1998Assignee: UOPInventor: Gregory J. Gajda
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Patent number: 5656152Abstract: A continuous water washing process for removing salts from refinery process streams is disclosed. The salt and salt precursor content of a process stream is determined, and iterative calculations made to ensure an aqueous phase forms downstream of the water injection point with a salt and ion concentration within acceptable limits. Preferably chemical speciation calculations are used to check for corrosive, transient aqueous phases intermediate the point of water injection and the process outlet.Type: GrantFiled: December 5, 1994Date of Patent: August 12, 1997Assignee: Mobil Oil CoporationInventors: Bruce D. McLaughlin, Yiing-Mei Wu
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Patent number: 5656151Abstract: A process for determining if intermittent water injection is the best way to remove deposits such as salts from refinery process streams. A water vapor pressure, P1, at stream conditions and a water vapor pressure, Ps, at saturation conditions in the stream, are used to calculate a ratio P1/Ps. If the ratio is less than 0.1 intermittent water washing is preferred. An optimized intermittent injection procedure, frequency, duration, and constraints, is disclosed. Chemical speciation calculations ensure that all accumulated salts are removed, and that an aqueous phase forms downstream of the water injection point having a salt concentration within acceptable limits.Type: GrantFiled: December 5, 1994Date of Patent: August 12, 1997Assignee: Mobil Oil CorporationInventors: Bruce D. McLaughlin, Yiing-Mei Wu
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Patent number: 5635055Abstract: The yield and quality of products secured from cracking units is increased by the process of subjecting the product stream secured from such cracking unit to a selective aromatics removal process and recycling the recovered aromatics lean (saturates rich) stream to the cracking unit whereby such saturates rich stream is subjected to increased conversion to higher value desired products.Type: GrantFiled: July 19, 1994Date of Patent: June 3, 1997Assignee: Exxon Research & Engineering CompanyInventors: James R. Sweet, Tan-Jen Chen, Charles P. Darnell
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Patent number: 5626742Abstract: The present invention relates to a continuous in-situ process for the removal of organically bound sulfur existing as mercaptans, sulfides and thiophenes comprising the steps of (a) contacting a heavy oil with aqueous sodium hydroxide at a temperature of about 380.degree. C. to about 450.degree. C. for a time sufficient to form sodium sulfide, and (b) steam stripping the sodium sulfide of step (a) at a temperature sufficient to convert said sodium sulfide to sodium hydroxide and recirculating the sodium hydroxide from step (b) back to step (a) and removing hydrogen sulfide and the metals from the organically bound metal complex of the sodium sulfide to convert it back to sodium hydroxide, in which case the sulfur may be recovered as H.sub.2 S rather than the metal sulfide. Optionally, molecular hydrogen may be added in the first step. The present invention is useful in removing organically bound sulfur that has been recognized to be difficult to remove, such as thiophenes.Type: GrantFiled: May 2, 1995Date of Patent: May 6, 1997Assignee: Exxon Reseach & Engineering CompanyInventors: Glen Brons, Ronald D. Myers
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Patent number: 5470457Abstract: Hydrocarbon-containing fluid compositions are provided comprising at least one hydrocarbon fluid, at least one heteroaromatic, and at least one hydrazine additive. The resulting composition has reduced temporal formation of colored materials and/or gummy deposits. Additionally, antioxidant additives are combined with the above composition and provide a further reduction in the formation of colored materials and/or gummy deposits.Type: GrantFiled: June 17, 1994Date of Patent: November 28, 1995Assignee: Phillips Petroleum CompanyInventors: Joseph E. Bares, Byron G. Johnson, Frederick J. Cornforth
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Patent number: 5415785Abstract: A method for reducing cyanide contaminants in refinery waste waters prior to reuse or release into the environment comprising adding to the waters a cyanide reactive scavenger comprising at least one amine-aldehyde reaction product.Type: GrantFiled: October 18, 1993Date of Patent: May 16, 1995Assignee: Nalco Chemical CompanyInventors: Michael L. Braden, Veronica K. Braden, Manian Ramesh, Everett C. Phillips
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Patent number: 5414183Abstract: An improved process is disclosed for the removal of nitrogen compounds from light hydrocarbon streams. Such nitrogen removal enhances the performance of catalytic processes which upgrade light hydrocarbons, especially light olefins, such as isomerization and etherification. The nitrogen-removal process can usefully be combined with steps for removal of sulfur compounds and highly unsaturated compounds in a process combination for upgrading the light hydrocarbons.Type: GrantFiled: December 24, 1992Date of Patent: May 9, 1995Assignee: UOPInventors: Hayim Abrevaya, Suleyman M. Ozmen, Paul T. Barger, Christopher D. Gosling, Thomas A. Verachtert
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Patent number: 5340554Abstract: A refinery catalyst is regenerated by burning off coke in an air stream to give an off-gas: before cryogenic recovery of hydrocarbons from the off-gas, nitrogen oxides (NOx) are removed from the off-gas by contact with a hydrogenation catalyst.Type: GrantFiled: May 21, 1993Date of Patent: August 23, 1994Assignee: Imperial Chemical Indutries PLCInventor: Peter J. H. Carnell
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Patent number: 5308473Abstract: A process and apparatus for fluidized bed regeneration of FCC catalyst are disclosed. Oxides of nitrogen (NO.sub.x) emissions from an FCC regenerator operating in complete CO combustion mode, and hydrothermal catalyst deactivation, are reduced by reducing the average bed temperature. Dilute phase afterburning superheats catalyst entrained in the dilute phase region above the fluidized bed. Cyclone separators recover superheated, entrained catalyst and preferentially recycle this catalyst to the FCC reactor, permitting cooler operation of the dense phase fluidized bed.Type: GrantFiled: September 18, 1992Date of Patent: May 3, 1994Assignee: Mobil Oil CorporationInventors: Catherine L. Markham, Gregory P. Muldowney
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Patent number: 5298153Abstract: An attrition resistant catalytic cracking catalyst is prepared by spray drying an aqueous slurry containing a molecular sieve having cracking activity, a clay such as kaolin, a silica sol and aluminum chlorhydroxide. The resultant catalyst has a high attrition resistance as compared to commercially available cracking catalysts.Type: GrantFiled: October 31, 1990Date of Patent: March 29, 1994Assignee: Union Oil Company of CaliforniaInventor: Julius Scherzer
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Patent number: 5269908Abstract: In a process for the separation of hydrocarbon materials and other materials including ammonia and hydrogen chloride normally associated with the hydrocarbon materials in refining of petroleum, the deposition of ammonium chloride is retarded or prevented by introducing inert gas of higher volatility into the processing operation upstream from where the deposition of ammonium chloride would otherwise occur.Type: GrantFiled: August 27, 1992Date of Patent: December 14, 1993Assignee: Nalco Canada Inc.Inventor: Bordan W. Krupay
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Patent number: 5225159Abstract: A method is provided for treating a sewage sludge-derived oil having a particular chemical composition, to reduce its odor. The method includes the first step of distilling the sewage sludge-derived oil to 150.degree. C. to remove water and volatile organic components, and then the essential step of circulating a gas consisting essentially of carbon dioxide gas therethrough.Type: GrantFiled: December 13, 1991Date of Patent: July 6, 1993Inventors: Henry Sawatzky, Terrance Giddings, Brian Farnand
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Patent number: 5190641Abstract: A method for making a hydrotreating catalyst wherein the catalyst is prepared by mixing a peptized hydrated supporting oxide with a hydrated Group IVB metal oxide gel promoter. The Group VIII metals are mixed in with the Group IVB metal oxide gel promoter. A solution containing a soluble Group VIB metal and a basic compound is added. The catalyst is used for hydrodenitrogenation and Ramsbottom Carbon Residue reduction of a hydrocarbon feedstock.Type: GrantFiled: November 13, 1991Date of Patent: March 2, 1993Assignee: Chevron Research and Technology CompanyInventors: Charles R. Wilson, Kirk R. Gibson
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Patent number: 5190642Abstract: A method of making a hydrotreating catalyst wherein the catalyst is prepared by mixing a peptized alumina support containing soluble Group IVB and Group VIII metal compounds with a solution containing a soluble Group VIB metal compound and a basic compound. The catalyst is used for hydrodenitrogenation and Ramsbottom Carbon Residue reduction of a hydrocarbon feedstock.Type: GrantFiled: November 13, 1991Date of Patent: March 2, 1993Assignee: Chevron Research and Technology CompanyInventors: Charles R. Wilson, Kirk R. Gibson, Chi-Wen Hung
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Patent number: 5180485Abstract: Indole impurities are removed from hydrocarbon-containing fluids by means of a magnesia-containing sorbent material.Type: GrantFiled: September 10, 1991Date of Patent: January 19, 1993Assignee: Phillips Petroleum CompanyInventors: Filippo Pennella, Fan-Nan Lin, Marvin M. Johnson
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Patent number: 5118406Abstract: A catalytic hydrotreating process wherein silicon-containing contaminants contained in a hydrocarbon feedstream are deposited onto a hydrotreating catalyst bed during hydrotreating in a manner providing improved catalyst stability. Hydrotreating catalysts having relatively high activities and low surface areas are located downstream of upstream hydrotreating catalysts having relatively low activities and high surface areas.Type: GrantFiled: April 30, 1991Date of Patent: June 2, 1992Assignee: Union Oil Company of CaliforniaInventors: Peter Kokayeff, Danford E. Clark, Howard D. Simpson
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Patent number: 5098556Abstract: The invention relates to a method for removing RCS from off-spec white mineral oil prepared by catalytic hydrogenation by filtering the off-spec white mineral oil through a bleaching clay, such as a smectite clay, particularly an acid treated montmorillonite clay, such as bentonite or attapulgite.Type: GrantFiled: June 14, 1990Date of Patent: March 24, 1992Assignee: Lyondell Petrochemical CompanyInventors: Caridad Go, Thomas F. Wulfers, Martin P. Grosboll, Frank F. McKay
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Patent number: 5055179Abstract: Heavy crude oils are upgraded thermally in the presence of water and a polyhydroxy metal bentonite in an autoclave, particularly at a temperature of about 200.degree. to about 300.degree. C.Type: GrantFiled: June 13, 1989Date of Patent: October 8, 1991Assignee: Ortech CorporationInventor: J. David Tyrer
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Patent number: 5015364Abstract: A process is disclosed for operating a refinery gas plant such as the unsaturated gas plant of a catalytic hydrocarbon conversion process that results in a reduction of the corrosive effect of acid gases on the gas plant vessels and equipment. The process comprises contacting acidic hydrocarbon feedstreams to an unsaturated gas plant separator zone with lean acid gas absorbing absorbent in an absorbtion zone comprising at least one liquid absorber bed and one vapor absorber bed. The liquid and vapor absorber beds are located upstream of the separator zone. The feedstreams to the gas plant comprise unstabilized, or wild, liquid gasoline and liquid and vapor output streams from the liquid-vapor separator for inter-stage wet gas compressor of the conversion process main fractionator. Accordingly, these feedstreams are deacidified before separation in the USGP deethanizer-absorber, sponge absorber, and debutanizer. This also eliminates the need for deacidification of the gas plant product stream.Type: GrantFiled: June 21, 1989Date of Patent: May 14, 1991Assignee: Mobil Oil CorporationInventor: Mohsen N. Harandi
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Patent number: 5002655Abstract: A process for the recovery of aromatic nitrogen-containing compounds from an oily substance is disclosed which comprises extracting an oily substance containing aromatic nitrogen-containing compounds with a solvent containing water and a lower alkanol.Type: GrantFiled: March 15, 1989Date of Patent: March 26, 1991Assignee: Director-General of Agency of Industrial Science and TechnologyInventors: Koji Ukegawa, Teruo Kondo, Akimitsu Matsumura, Kazumasa Yazu
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Patent number: 4973399Abstract: Emission of noxious nitrogen oxides with the flue gas from the regenerator of a fluid catalytic cracking plant are reduced by incorporating into the circulating inventory of cracking catalyst separate additive particles that contain a copper-loaded zeolite. A particularly effective additive is provided, for example, by treating a ZSM-5 zeolite in a matrix consisting predominantly of titania, zirconia or a mixture thereof with a solution containing both copper and rare earth cations to incorporate both of these elements with the zeolitic composition.Type: GrantFiled: December 21, 1989Date of Patent: November 27, 1990Assignee: Mobil Oil CorporationInventors: Gary J. Green, David S. Shihabi, Tsoung Y. Yan
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Patent number: 4960508Abstract: A process for the removal of basic heterocyclic nitrogen compounds from petroleum oils which comprises:(a) contacting said petroleum oils containing basic heterocyclic nitrogen compounds with an aqueous solution of a first solvent comprising concentrated acid at extraction conditions in a first extract zone,(b) separating the product of step (a) into a raffinate product stream comprising hydrocarbons having a lean content of basic heterocyclic nitrogen compounds and residual acid levels, and a first extract phase comprising hydrocarbons, water and acid having a substantial content of basic heterocyclic nitrogen compounds,(c) flashing said first extract phase to remove bulk first solvent.Type: GrantFiled: January 30, 1989Date of Patent: October 2, 1990Assignee: Shell Oil CompanyInventor: Wayne E. Evans
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Patent number: 4960507Abstract: A process for the removal of basic heterocyclic nitrogen compounds from petroleum oils which comprises:(a) contacting said petroleum oils containing basic heterocyclic nitrogen compounds with an aqueous solution of an acidic solvent at extraction conditions in a first contacting zone,(b) separating the product of step (a) into a raffinate product stream comprising hydrocarbons having a lean content of basic heterocyclic nitrogen compounds and residual acid levels, and a first extract phase comprising hydrocarbons, water and acid having a substantial content of basic heterocyclic nitrogen compounds,(c) contacting said first extract phase with a hydrocarbon solvent which is substantially immiscible with said first extract phase at extraction conditions in a second contacting zone, and(e) separating the product of step (c) into a hydrocarbon recovery stream comprising the immiscible hydrocarbon solvent and oil-derived hydrocarbons having a lean content of basic heterocyclic nitrogen compounds and a second extracType: GrantFiled: October 6, 1989Date of Patent: October 2, 1990Assignee: Shell Oil CompanyInventors: Wayne E. Evans, George C. Blytas
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Patent number: 4923592Abstract: A process for producing a high octane gasoline from a hydrocarbon feedstock in which the feedstock is contacted in the presence of hydrogen under hydrocracking conditions, preferably ammonia-rich hydrocracking conditions, with a hydrocracking catalyst comprising at least one hydrogenation metal component in combination with a cracking component. The preferred cracking components are Y zeolites and the catalyst preferably contains a nickel hydrogenation metal component, particularly in an amount greater than 13 weight percent, calculated as NiO. The catalyst may also contain a Group VIB metal component, such as a molybdenum component, particularly in a mole ratio greater than about 2 to 1, calculated as NiO to Group VIB metal trioxide. It has been found that such a process produces gasoline fractions having substantially increased research and motor octane numbers.Type: GrantFiled: December 5, 1988Date of Patent: May 8, 1990Assignee: Union Oil Company of CaliforniaInventor: Suheil F. Abdo
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Patent number: 4880521Abstract: Hydrocarbon feedstocks containing relatively high levels of nitrogen contaminants are converted by catalytic cracking to products of lower average molecular weight by contacting the feedstock under cracking conditions with a cracking catalyst having a surface area of at least 150 m.sup.2 /gm and comprising greater than about 25 weight percent of a Y zeolite dispersed in a matrix containing a synthetic silica-alumina component in which the weight ratio of silica-to-alumina is preferably equal to or greater than about 0.10.Type: GrantFiled: February 17, 1989Date of Patent: November 14, 1989Assignee: Union Oil Company of CaliforniaInventor: Julius Scherzer
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Patent number: 4810369Abstract: Hydrocarbon feedstocks containing relatively high levels of nitrogen contaminants are converted by catalytic cracking to products of lower average molecular weight by contacting the feedstock under cracking conditions with a cracking catalyst having a surface area of at least 150 m.sup.2 /gm and comprising greater than about 25 weight percent of a rare earth exchanged Y zeolite dispersed in a matrix containing a synthetic silica-alumina component in which the weight ratio of silica-to-alumina is equal to or greater than about 0.5.Type: GrantFiled: May 7, 1987Date of Patent: March 7, 1989Assignee: Union Oil Company of CaliforniaInventor: Julius Scherzer
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Patent number: 4790930Abstract: A process is disclosed for the removal of basic heterocyclic nitrogen compounds from a petroleum crude oil or fraction thereof which comprises first treating the petroleum crude oil or fraction thereof rich in basic heterocyclic nitrogen compounds in a two-phase extraction zone with an extractant consisting essentially of an aqueous solution of a lower carboxylic acid, preferably having between 1 and 15 carbon atoms. The extractant complexes the basic heterocyclic nitrogen compounds to produce a stream of petroleum crude oil or fraction thereof having a smaller content of heterocyclic nitrogen compounds and a stream comprising the lower carboxylic acid extractant with an increased quantity of basic heterocyclic nitrogen compounds. The petroleum crude oil or fraction thereof possessing a reduced quantity of heterocyclic nitrogen compounds is hydrotreated in the presence of hydrogen and a hydrotreating catalyst to further remove the basic heterocyclic nitrogen compounds.Type: GrantFiled: May 29, 1987Date of Patent: December 13, 1988Assignee: Shell Oil CompanyInventors: Ajay M. Madgavkar, Don M. Washecheck
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Patent number: 4749472Abstract: The instant invention discloses a method of removing heterocyclic basic nitrogen compounds from petroleum oils which comprises first enhancing the concentration of the heterocyclic basic nitrogen compounds in a portion of the petroleum oil and then extracting the enhanced portion of the heterocyclic basic nitrogen compounds with a two phase system having an aliphatic carboxylic acid as the extracting agent. In the hydrotreating embodiment of this invention a portion of all of the nitrogen compounds are converted to heterocyclic basic nitrogen compounds and thereby more feasibly extracted. In the distillation embodiment of this invention the nitrogen compounds are actually concentrated and thereby result in a more feasible extraction with the aliphatic carboxylic acid.Type: GrantFiled: March 6, 1987Date of Patent: June 7, 1988Assignee: Shell Oil CompanyInventor: Ajay M. Madgavkar
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Patent number: 4747937Abstract: A process for the removal of hydrogenatable hydrocarbonaceous compounds from a hydrocarbonaceous stream which comprises the steps of: (a) contacting the hydrocarbonaceous stream with an adsorbent to remove at least a portion of the hydrogenatable hydrocarbonaceous compounds from the hydrocarbonaceous stream to provide a hydrocarbonaceous stream having a reduced concentration of hydrogenatable hydrocarbonaceous compounds; (b) contacting spent adsorbent which has accumulated the hydrogenatable hydrocarbonaceous compounds from the hydrocarbonaceous stream with an elution solvent to remove the hydrogenatable hydrocarbonaceous compounds from the spent adsorbent thereby regenerating the adsorbent; (c) recovering at least a portion of the elution solvent from a resulting admixture of elution solvent and hydrogenatable hydrocarbonaceous compounds recovered from step (b) in an elution solvent recovery zone; (d) contacting the hydrogenatable hydrocarbonaceous compounds which were recovered from step (c) in the presenceType: GrantFiled: November 24, 1986Date of Patent: May 31, 1988Assignee: UOP Inc.Inventors: Lee Hilfman, Russell W. Johnson
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Patent number: 4747935Abstract: Hydrocarbon feedstocks containing relatively high levels of nitrogen contaminants are converted by catalytic cracking to products of lower average molecular weight by contacting the feedstock with a mixture of a cracking catalyst and separate particles of a nitrogen scavenger comprising microporous solids selected from the group consisting of acid clays; hydrogen or ammonium exchanged mordenite, clinoptilolite, chabazite and erionite; mineral acids or mineral acid precursors supported on an inorganic, refractory oxide; and Catapal alumina.Type: GrantFiled: March 26, 1986Date of Patent: May 31, 1988Assignee: Union Oil Company of CaliforniaInventor: Julius Scherzer
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Patent number: 4746420Abstract: A process for upgrading diesel oil comprising the steps of:(1) reacting the diesel oil with a nitrogenous treating agent;(2) contacting the diesel oil from step (1) above with(a) a primary solvent selected from the group consisting of organic solvents having a dipole moment of about 1.Type: GrantFiled: February 24, 1986Date of Patent: May 24, 1988Assignee: REI Technologies, Inc.Inventors: Saeed T. Darian, Sayed-Hamid Arabshahi
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Patent number: 4743360Abstract: A process for removing the basic nitrogen compounds from gas oils comprises treating the gas oils with a homogeneous solvent mixture comprising a diluted aqueous acid solution and an alcohol having from 1 to 6 carbon atoms, the volume ratio of alcohol to diluted aqueous acid solution being between 90/10 and 10/90, the volume ratio of solvent mixture to gas oils being between 0.5 and 5.Type: GrantFiled: October 23, 1986Date of Patent: May 10, 1988Assignee: Labofina, S.A.Inventors: Michel Melin, Jacques F. Grootjans, Andre Vanderlinden
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Patent number: 4731174Abstract: Hydrocarbon feedstocks containing relatively high levels of nitrogen contaminants are converted to products of lower average molecular weight by first mixing the feedstock with a dicarboxylic acid such as oxalic acid and then contacting the resultant mixture with a cracking catalyst in a cracking zone under cracking conditions in the substantial absence of added molecular hydrogen. The use of a dicarboxylic acid in lieu of a mineral acid such as sulfuric acid or nitric acid results in less corrosion to FCC unit internals and less emissions of sulfur and nitrogen oxides from the FCC unit regenerator.Type: GrantFiled: June 24, 1987Date of Patent: March 15, 1988Assignee: Union Oil Company of CaliforniaInventors: Mario L. Occelli, Edward J. Aitken
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Patent number: 4708786Abstract: Hydrocarbon feedstocks containing relatively high levels of nitrogen contaminants are converted by catalytic cracking to products of lower average molecular weight by contacting the feedstock with a mixture of a cracking catalyst and separate particles of a nitrogen scavenger. The nitrogen scavenger is a particulate solid acid capable of sorbing pyridine at room temperature and retaining greater than about 5 weight percent of the sorbed pyridine after heating in a vacuum to about 300.degree. C. Examples of the nitrogen scavengers that can be used in the process include amorphous aluminosilicates, nonzeolitic molecular sieves such as pillared clays and delaminated clays, and zeolitic molecular sieves.Type: GrantFiled: March 26, 1986Date of Patent: November 24, 1987Assignee: Union Oil Company of CaliforniaInventor: Mario L. Occelli
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Patent number: 4671865Abstract: The instant invention discloses a method of removing heterocyclic basic nitrogen compounds from petroleum oils which comprises first enhancing the concentration of the heterocyclic basic nitrogen compounds in a portion of the petroleum oil and then extracting the enhanced portion of the heterocyclic basic nitrogen compounds with a two phase system having an aliphatic carboxylic acid as the extracting agent. In the hydrotreating embodiment of this invention a portion of all of the nitrogen compounds are converted to heterocyclic basic nitrogen compounds and thereby more feasibly extracted. In the distillation embodiment of this invention the nitrogen compounds are actually concentrated and thereby result in a more feasible extraction with the aliphatic carboxylic acid.Type: GrantFiled: September 27, 1985Date of Patent: June 9, 1987Assignee: Shell Oil CompanyInventors: Ajay M. Madgavkar, Donald M. Washecheck
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Patent number: 4623444Abstract: A method for reducing the nitrogen content of shale oil is disclosed. The method comprises distilling shale oil to form a distillate containing lighter shale oil compounds and a residue containing heavier compounds. Nitrogen-containing compounds are extracted from the distillate to form a first nitrogen-lean raffinate and a first nitrogen-rich extract. Nitrogen-containing compounds are also extracted from the residue to form a second nitrogen-lean raffinate and a second nitrogen-rich extract. The second nitrogen-lean raffinate is hydro-treated to further reduce its nitrogen content.Type: GrantFiled: June 27, 1985Date of Patent: November 18, 1986Assignee: Occidental Oil Shale, Inc.Inventors: Stanley C. Che, Ajay Madgavkar
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Patent number: 4622129Abstract: A process is disclosed for the manufacture of lubricating base oils from nitrogen-containing distillates and/or deasphalted oils by subjecting them to a catalytic hydrotreatment which may be followed by a dewaxing treatment, wherein distillates and/or deasphalted oils having a nitrogen content which numerically expressed exceeds the value f.multidot.P.sub.H2 .multidot.S.sub.v.sup.-1, wherein f is a constant relating to the viscosity of the final base oil, P.sub.H2 represents the hydrogen partial pressure in bar applied in the catalytic hydrotreatment and S.sub.v represents the weighted hourly space velocity in t/m.sup.3 .multidot.h at which the catalytic hydrotreatment is carried out, are subjected to a preceding solvent extraction.Type: GrantFiled: October 11, 1985Date of Patent: November 11, 1986Assignee: Shell Oil CompanyInventors: Gerhard G. Bayle, Henricus M. J. Bijwaard, Martinus M. P. Janssen
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Patent number: H581Abstract: A process for purifying mineral spirits which have been used to clean Otto uel II propelled torpedoes by heating the mineral spirits to decompose 1,2-propanediol dinitrate and remove hydrogen cyanide and other gaseous decomposition produces, and then distill the mineral spirits from the remaining contaminants.Type: GrantFiled: July 9, 1987Date of Patent: February 7, 1989Assignee: The United States of America as represented by the Secretary of the NavyInventors: Steven L. Collignon, Dennis R. Knudsen
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Patent number: H1368Abstract: A method for improving the long-term color stability of jet fuel and jet fuel blends containing nitrogen compounds, by intimately mixing the jet fuel with a quantity of concentrated sulfuric acid sufficient to remove at least about ninety percent (90%) of said nitrogen compounds during a contact time equal to less than five (5) minutes, separating the jet fuel from the concentrated sulfuric acid, mixing the jet fuel with an aqueous caustic solution to remove residual acid from the jet fuel, separating the jet fuel from the aqueous caustic solution, mixing the jet fuel with water, and separating the jet fuel from the water.Type: GrantFiled: December 11, 1992Date of Patent: November 1, 1994Inventor: Michael C. Fraytet