Organic Acid Patents (Class 208/282)
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Patent number: 8920633Abstract: High energy (e.g., ultrasonic) mixing of a liquid hydrocarbon feedstock and reactants comprised of an oxidation source, catalyst and acid yields a diesel fuel product or additive having substantially increased cetane number. Ultrasonic mixing creates cavitation, which involves the formation and violent collapse of micron-sized bubbles, which greatly increases the reactivity of the reactants. This, in turn, substantially increases the cetane number compared to reactions carried out using conventional mixing processes, such as simple mechanical stirring. Alternatively, an aqueous mixture comprising water and acid can be pretreated with an oxidation source such as ozone and subjected to ultrasonic cavitation prior to reacting the pretreated mixture with a liquid hydrocarbon feedstock.Type: GrantFiled: September 8, 2010Date of Patent: December 30, 2014Assignee: Cetamax Ventures Ltd.Inventors: Kin Meng Chan, Kamalul Arifin Yusof, Shahrul Niza Bin Abdul Rahim, Md Asraff Bin Abdul Karim, Roger Kai Lott
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Patent number: 8894843Abstract: A method of upgrading a heteroatom-containing hydrocarbon feed by removing heteroatom contaminants is disclosed. The method includes contacting the heteroatom-containing hydrocarbon feed with an oxidant and an immiscible acid to oxidize the heteroatoms, contacting the oxidized- heteroatom-containing hydrocarbon feed with caustic and a selectivity promoter, and removing the heteroatom contaminants from the heteroatom-containing hydrocarbon feed. The oxidant may be used in the presence of a catalyst.Type: GrantFiled: June 11, 2012Date of Patent: November 25, 2014Assignee: Auterra, Inc.Inventors: Jonathan P. Rankin, Jennifer L. Vreeland, Kyle E. Litz, Tracey M. Jordan, Mark N. Rossetti, Eric H. Burnett, Trent A. McCaskill
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Patent number: 8685233Abstract: The invention relates to field of processing hydrocarbon feedstock including crude oil, wherein metals such as calcium are removed. In the face of the rising prices of crude oil, refiners are forced to process opportunity crudes such as DOBA, which pose many problems including fouling of equipment due to certain metallic salts, such as calcium napthenate. Calcium, which cannot be removed from crude oil during normal desalting process, poses very serious problems. The invention provides method for removal of calcium, wherein crude oil is mixed, with effective metal removing amount of aqueous extraction solution of an additive comprising a chemical compound selected from a group consisting of metallic acid, maleic anhydride or fumaric acid or salts or derivatives thereof, enabling separation of hydrocarboneous phase and aqueous phase containing metal ions, in crude desalter. Only hydrocarboneous phase devoid of calcium is processed further, thereby preventing fouling of equipment.Type: GrantFiled: August 21, 2007Date of Patent: April 1, 2014Assignee: Dork Ketal Chemicals (I) Private LimitedInventor: Mahesh Subramaniyam
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Patent number: 8672075Abstract: A vehicle assembly is provided for facilitating transportation in a stable vehicle not requiring government licensing. The assembly includes a frame assembly having a left frame coupled to a right frame. The frame assembly has a center frame coupled to and positioned between the left frame and the right frame. A plurality of wheels is coupled to the frame assembly including a left front wheel and a left back wheel coupled to the left frame and a right front wheel and a right back wheel coupled to the right frame. A seat assembly is positioned between the left frame and the right frame. A steering mechanism is coupled to the frame assembly and mechanically coupled to the left front wheel and the right front wheel. A drive system is operationally coupled to at least one of the plurality of wheels.Type: GrantFiled: March 15, 2012Date of Patent: March 18, 2014Inventor: Sean H. Walker
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Publication number: 20130233770Abstract: There is provided an additive and method for removal of calcium from crude oil or its blends containing calcium naphthenate at low pH as well as at high pH. Particularly, there is also provided an additive and method for removal of calcium from crude oil or its blends containing calcium naphthenate under basic or alkaline conditions and at low pH as well as at high pH varying from about 5 to 11.Type: ApplicationFiled: November 14, 2011Publication date: September 12, 2013Applicant: DORF KETAL CHEMICALS (INDIA) PRIVATE LIMITEDInventor: Mahesh Subramaniyam
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Patent number: 8425765Abstract: Solid organic acids may be introduced into hydrocarbon solvents to form dispersions; the dispersions in turn may be introduced into crude oil. A wash water may be added to the crude oil to create an emulsion. The organic acids may transfer metals and/or amines from a hydrocarbon phase into an aqueous phase in an electrostatic desalter which resolves the emulsion into the two phases. Suitable solid organic acids include, but are not necessarily limited to, C2-C4 alpha hydroxyacids, such as, but not necessarily limited to, glycolic acid, malic acid, maleic acid, malonic acid, succinic acid and even sulfamic acid, chloroacetic acid, thiomalic acid, including esters of, polymers of, amine salts of, alkali metal salts of, and/or ammonium salts of all of these acids.Type: GrantFiled: September 9, 2011Date of Patent: April 23, 2013Assignee: Baker Hughes IncorporatedInventors: Lawrence N. Kremer, Jerry J. Weers, Corina Sandu
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Patent number: 8366915Abstract: Methods for reducing calcium deposition along surfaces in contact with the water phase of a resolved water/oil emulsion are disclosed. High calcium crude oil and the like are contacted with a sequestrant to form a sequestered calcium containing complex that partitions to the water phase in the resolved emulsion. A specifically formulated polymeric deposit control agent is added to the water phase to inhibit calcium deposit formation therein and along surfaces in contact with the water phase.Type: GrantFiled: June 26, 2008Date of Patent: February 5, 2013Assignee: General Electric CompanyInventors: Alan E. Goliaszewski, David B. Engel, Roger C. May
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Publication number: 20120285866Abstract: A method of upgrading a heteroatom-containing hydrocarbon feed by removing heteroatom contaminants is disclosed. The method includes contacting the heteroatom-containing hydrocarbon feed with an oxidant to oxidize the heteroatoms, contacting the oxidized-heteroatom-containing hydrocarbon feed with caustic and a selectivity promoter, and removing the heteroatom contaminants from the heteroatom-containing hydrocarbon feed. The oxidant may be used in the presence of a catalyst.Type: ApplicationFiled: July 27, 2012Publication date: November 15, 2012Inventors: Kyle E. Litz, Jennifer L. Vreeland, Jonathan P. Rankin, Mark N. Rossetti, Tracey M. Jordan, Trent A. McCaskill
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Patent number: 8298404Abstract: A reaction system and method for removing heteroatoms from oxidized-heteroatom-containing hydrocarbon streams and products derived therefrom are disclosed. An oxidized-heteroatom-containing hydrocarbon feed is reacted in a reaction system thereby forming non-ionic hydrocarbon products. The products derived therefrom are useful as transportation fuels, lubricants, refinery intermediates, or refinery feeds.Type: GrantFiled: September 22, 2010Date of Patent: October 30, 2012Assignee: Auterra, Inc.Inventors: Kyle E. Litz, Jennifer L. Vreeland, Jonathan P. Rankin, Thomas W. DeLancey, Timothy A. Thompson
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Patent number: 8241490Abstract: A method of upgrading a heteroatom-containing hydrocarbon feed by removing heteroatom contaminants is disclosed. The method includes contacting the heteroatom-containing hydrocarbon feed with an oxidant to oxidize the heteroatoms, contacting the oxidized-heteroatom-containing hydrocarbon feed with caustic and a selectivity promoter, and removing the heteroatom contaminants from the heteroatom-containing hydrocarbon feed. The oxidant may be used in the presence of a catalyst.Type: GrantFiled: October 14, 2010Date of Patent: August 14, 2012Assignee: Auterra, Inc.Inventors: Kyle E. Litz, Jennifer L. Vreeland, Jonathan P. Rankin, Mark N. Rossetti, Tracey M. Jordan
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Patent number: 8197671Abstract: A method of upgrading a heteroatom-containing hydrocarbon feed by removing heteroatom contaminants is disclosed. The method includes contacting the heteroatom-containing hydrocarbon feed with an oxidant and an immiscible acid to oxidize the heteroatoms, contacting the oxidized-heteroatom-containing hydrocarbon feed with caustic and a selectivity promoter, and removing the heteroatom contaminants from the heteroatom-containing hydrocarbon feed. The oxidant may be used in the presence of a catalyst.Type: GrantFiled: December 23, 2010Date of Patent: June 12, 2012Assignee: Auterra, Inc.Inventors: Jonathan P. Rankin, Jennifer L. Vreeland, Kyle E. Litz, Tracey M. Jordan, Mark N. Rossetti, Eric H. Burnett
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Publication number: 20110309001Abstract: The invention relates to a class of novel surfactants that have utility in the recovery and/or extraction of oil.Type: ApplicationFiled: December 2, 2010Publication date: December 22, 2011Inventors: David Soane, Rosa Casado Portilla, John H. Dise, Robert P. Mahoney
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Publication number: 20110192767Abstract: An extraction aid has been found which provides for enhanced contaminate removal, such as metals and amines, from crude oils that uses components that are desirable in desalting processes as the components are water soluble, have low toxicity, are highly biodegradeable and exhibit high thermal stability. According to one embodiment of the invention, an extraction aid that provides enhanced extraction properties is comprised of a blend of acids, particularly water soluble acids. More specifically, a combination of two acids chosen from the group consisting of acetic acid, sulfuric acid, glycolic acid, citric acid and methanesulfonic acid.Type: ApplicationFiled: April 21, 2011Publication date: August 11, 2011Applicant: GENERAL ELECTRIC COMPANYInventors: Alan E. Goliaszewski, Cato R. McDaniel
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Publication number: 20110065612Abstract: The invention relates to a class of novel surfactants that have utility in the recovery and/or extraction of oil.Type: ApplicationFiled: December 10, 2009Publication date: March 17, 2011Inventors: Kristoffer K. Stokes, Michael C. Berg, David Soane, Kevin T. Petersen, John H. Dise, Atul C. Thakrar, Rosa Casado
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Publication number: 20110031164Abstract: A method of upgrading a heteroatom-containing hydrocarbon feed by removing heteroatom contaminants is disclosed. The method includes contacting the heteroatom-containing hydrocarbon feed with an oxidant to oxidize the heteroatoms, contacting the oxidized-heteroatom-containing hydrocarbon feed with caustic and a selectivity promoter, and removing the heteroatom contaminants from the heteroatom-containing hydrocarbon feed. The oxidant may be used in the presence of a catalyst.Type: ApplicationFiled: October 14, 2010Publication date: February 10, 2011Applicant: AUTERRA INC.Inventors: Kyle E. Litz, Jennifer L. Vreeland, Jonathan P. Rankin, Mark N. Rossetti, Tracey M. Jordan
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Patent number: 7857965Abstract: A process for upgrading hydrocarbonaceous oil containing heteroatom-containing compounds where the hydrocarbonaceous oil is contacted with a solvent system that is a mixture of a major portion of a polar solvent having a dipole moment greater than about 1 debye and a minor portion of water to selectively separate the constituents of the carbonaceous oil into a heteroatom-depleted raffinate fraction and heteroatom-enriched extract fraction. The polar solvent and the water-in-solvent system are formulated at a ratio where the water is an antisolvent in an amount to inhibit solubility of heteroatom-containing compounds and the polar solvent in the raffinate, and to inhibit solubility of non-heteroatom-containing compounds in the extract. The ratio of the hydrocarbonaceous oil to the solvent system is such that a coefficient of separation is at least 50%.Type: GrantFiled: April 4, 2005Date of Patent: December 28, 2010Assignee: James W. Bunger and Associates Inc.Inventors: James W. Bunger, Donald E. Cogswell
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Patent number: 7799213Abstract: Reactive phosphorus species can be removed or transferred from a hydrocarbon phase to a water phase in an emulsion breaking process by using a composition that contains water-soluble hydroxyacids. Suitable water-soluble hydroxyacids include, but are not necessarily limited to glycolic acid, gluconic acid, C2-C4 alpha-hydroxy acids, poly-hydroxy carboxylic acids, thioglycolic acid, chloroacetic acid, polymeric forms of the above hydroxyacids, poly-glycolic esters, glycolate ethers, and ammonium salt and alkali metal salts of these hydroxyacids, and mixtures thereof. The composition may optionally include a mineral acid to reduce the pH of the desalter wash water. A solvent may be optionally included in the composition. The invention permits transfer of reactive phosphorus species into the aqueous phase with little or no hydrocarbon phase undercarry into the aqueous phase. The composition is particularly useful in treating crude oil emulsions, and in removing calcium and other metals therefrom.Type: GrantFiled: July 8, 2005Date of Patent: September 21, 2010Assignee: Baker Hughes IncorporatedInventors: Lawrence N. Kremer, Tran M. Nguyen, Jerry J. Weers
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Publication number: 20100147739Abstract: High molecular weight naphthenic tetra-acids are added to a base crude oil to prevent and/or reduce fouling of crude oil refinery equipment. The method includes adding an effective amount of a high molecular weight naphthenic tetra-acid to the base crude oil to form a crude oil mixture and feeding the crude oil mixture to a crude oil refinery component. Particularly, the high molecular weight naphthenic tetra-acids include ARN acids.Type: ApplicationFiled: December 4, 2009Publication date: June 17, 2010Applicant: ExxonMobil Research and Engineering CompanyInventors: Steven W. LEVINE, Glen B. Brons, George A. Lutz, Daniel P. Leta, Clifford C. Walters
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Patent number: 7704376Abstract: The use of water-soluble aromatic polysulfonic acid salts for inhibiting fouling in process equipment used in the thermal treatment of heavy oils.Type: GrantFiled: May 12, 2005Date of Patent: April 27, 2010Assignee: ExxonMobil Research and Engineering CompanyInventors: Ramesh Varadaraj, Michael Siskin, Leo D. Brown, Maa S. Maa
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Patent number: 7594989Abstract: A method for upgrading heavy oils by contacting the heavy oil with a water-soluble aromatic polysulfonic acid salt and then thermally treating the contacted heavy oil. The polysulfonic acid salt can be recovered and recycled from contacting the heavy oil. The polysulfonic acid salt is recovered and recycled. The invention also relates to the upgraded product from the enhanced thermal treatment process.Type: GrantFiled: May 12, 2005Date of Patent: September 29, 2009Assignee: ExxonMobile Research and Engineering CompanyInventors: Ramesh Varadaraj, Leo D. Brown
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Patent number: 7419939Abstract: The invention describes a method for decreasing the viscosity of crude oils and residuum utilizing a combination of thermal and acidic treatment. Further, the invention describes a method for making a water-in-oil emulsion, or a solids-stabilized water-in-oil emulsion with a reduced viscosity. The emulsion can be used in enhanced oil recovery methods, including using the emulsion as a drive fluid to displace hydrocarbons in a subterranean formation, and using the emulsion as a barrier fluid for diverting flow of fluids in the formation.Type: GrantFiled: June 16, 2004Date of Patent: September 2, 2008Assignee: ExxonMobil Upstream Research CompanyInventor: Ramesh Varadaraj
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Patent number: 7117722Abstract: Method to determine the viscosity of a water-in-oil emulsion that will be formed by an oil comprising organic acids when mixed with water comprising: determining the value of the expression: ? ( emul ) = K ? ? ? ( oil ) ? TAN - r ( 1 - ? ) 2.5 wherein ?(oil) is the viscosity the oil, TAN is the total acid number of the oil, ? is a number in the range of 0.1 to 0.8, r is a number in the range of about 0.5 to 2, and K is a number from about 1 to 20, said determined value, ?(emul) being the viscosity of the water-in-oil emulsion. The method is used to prepare water-in-oil emulsions of predetermined viscosity and to improve desalting of oils.Type: GrantFiled: October 12, 2004Date of Patent: October 10, 2006Assignee: ExxonMobil Research and Engineering CompanyInventor: Ramesh Varadaraj
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Patent number: 6875341Abstract: A process for upgrading hydrocarbonaceous oil containing heteroatom-containing compounds where the hydrocarbonaceous oil is contacted with a solvent system that is a mixture of a major portion of a polar solvent having a dipole moment greater than about 1 debye and a minor portion of water to selectively separate the constituents of the carbonaceous oil into a heteroatom-depleted raffinate fraction and heteroatom-enriched extract fraction. The polar solvent and the water-in-solvent system are formulated at a ratio where the water is an antisolvent in an amount to inhibit solubility of heteroatom-containing compounds and the polar solvent in the raffinate, and to inhibit solubility of non-heteroatom-containing compounds in the extract. The ratio of the hydrocarbonaceous oil to the solvent system is such that a coefficient of separation is at least 50%.Type: GrantFiled: May 23, 2000Date of Patent: April 5, 2005Assignee: James W. Bunger and Associates, Inc.Inventors: James W. Bunger, Donald E. Cogswell
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Publication number: 20040232051Abstract: The invention is a low viscosity oil composition derived from crude oils and crude oil residuum comprising dispersed asphaltene salts in a hydrocarbon continuous phase.Type: ApplicationFiled: June 4, 2004Publication date: November 25, 2004Inventor: Ramesh Varadaraj
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Patent number: 6800193Abstract: The invention describes a method for decreasing the viscosity of crude oils and residuum utilizing a combination of thermal and acidic treatment. Further, the invention describes a method for making a water-in-oil emulsion, or a solids-stabilized water-in-oil emulsion with a reduced viscosity. The emulsion can be used in enhanced oil recovery methods, including using the emulsion as a drive fluid to displace hydrocarbons in a subterranean formation, and using the emulsion as a barrier fluid for diverting flow of fluids in the formation.Type: GrantFiled: March 28, 2001Date of Patent: October 5, 2004Assignee: ExxonMobil Upstream Research CompanyInventor: Ramesh Varadaraj
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Patent number: 6673238Abstract: A process for hydrotreating acidic compounds of an acidic petroleum oil is disclosed. The process includes contacting the acidic petroleum oil with a hydrogen donor solvent to thereby produce a treated petroleum oil. The process can further include contacting a fraction or a full-boiling range portion of the treated petroleum oil with a hydrogenation catalyst in the presence of hydrogen and under process conditions sufficient to hydrogenate at least a portion of the hydrocarbons of the fraction or full-boiling range portion; and utilizing at least a portion of the hydrogenated fraction or full-boiling range portion as the hydrogen donor solvent.Type: GrantFiled: November 8, 2001Date of Patent: January 6, 2004Assignee: ConocoPhillips CompanyInventors: Bruce W. Gerhold, Joseph E. Bares, Scott D. Love, Jerry G. Feierabend
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Publication number: 20030132139Abstract: The invention describes a method for decreasing the viscosity of crude oils and residuum utilizing a combination of acid and sonic treatment.Type: ApplicationFiled: January 21, 2003Publication date: July 17, 2003Inventor: Ramesh Varadaraj
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Patent number: 6544411Abstract: The invention describes a method for decreasing the viscosity of crude oils and residuum utilizing a combination of acid and sonic treatment.Type: GrantFiled: March 9, 2001Date of Patent: April 8, 2003Assignee: ExxonMobile Research and Engineering Co.Inventor: Ramesh Varadaraj
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Patent number: 6102379Abstract: A metal spring with embedded constrained layer damping provides effective damping of a supported load. A continuous load bearing tube is provided with an inner diameter and an outer diameter with a plurality of constraining layer tube sections concentric with the load bearing tube and spaced along the load bearing tube. A damping layer of a viscoelastic material contacts facing surfaces of the continuous load bearing tube and the constraining layer tube sections so that shear strains are induced in the viscoelastic material from relative rotation of the load bearing tube and the constraining layer sections to provide damping of an applied load. In one embodiment, the constraining layer tube sections and damping are within the load bearing continuous tube and the continuous tube is sealed at each end to permit use of the spring in a vacuum environment.Type: GrantFiled: November 17, 1997Date of Patent: August 15, 2000Assignee: Hytec, Inc.Inventors: Eric R. Ponslet, William O. Miller
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Patent number: 6048904Abstract: The present invention is an asphaltene dispersant containing an aromatic, a sulfonic acid head, and an alkyl tail containing 16 carbons or more and at least one branch of a methyl or longer alkyl. Preferably, the aromatic is a fused two ring aromatic and the tail is a two, branched alkyl tail of 30 carbons or longer.Type: GrantFiled: December 1, 1998Date of Patent: April 11, 2000Assignee: Exxon Research and Engineering Co.Inventors: Irwin A. Wiehe, Ramesh Varadaraj, Torris G. Jermansen, Raymond J. Kennedy, Cornelius H. Brons
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Patent number: 5925233Abstract: The present invention relates to the use of secondary alkanesulphonic acids as asphaltene dispersing agent in crude oils and products derived therefrom, wherein a chain length of 8 to 22 C atoms is present. The secondary alkanesulfonic acids are employed in an amount of from 1 to 10,000 ppm by volume. The alkanesulfonic acid is preferably formulated as a solution or microemulsion, and can further contain optional alkyl-formaldehyde resin, oxyalkylated amines, or wax-dispersing agents. The alkanesulfonic acids provide reduced precipitate amounts, slow the rate of precipitate formation, form a more finely divided precipitate and reduce the tendency of the precipitate to be deposited on surfaces.Type: GrantFiled: October 14, 1997Date of Patent: July 20, 1999Assignee: Clariant GmbHInventors: Dennis Miller, Axel Vollmer, Michael Feustel
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Patent number: 5282959Abstract: A method of extracting iron species from a liquid hydrocarbon medium comprising adding to the medium a composition comprised of an aminocarboxylic acid, methoxypropylamine and a solvent selected from the group consisting of 2-ethylhexanol, cresylic acid, ethylene glycol and hexylene glycol.Type: GrantFiled: March 16, 1992Date of Patent: February 1, 1994Assignee: Betz Laboratories, Inc.Inventors: Paul V. Roling, Cato R. McDaniel
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Patent number: 5152886Abstract: A process for reducing asphaltene content of crude oil and oil-containing materials to improve rheological properties of crude oils enhancing the water-extractabilities of sulphur and metals contained in them. The process employs the cold cracking effect of a binary acid solution containing, preferably, hydrochloric acid and oleic acid. The process is particularly applicable to the exploitation of heavy and ultra-heavy oil deposits, to oil recovery from oil-containing tar sand, shale or clay and to the cleaning of oil tanks, garments and clogged oil-pipelines.Type: GrantFiled: October 31, 1990Date of Patent: October 6, 1992Assignee: Laboratorios Paris, C.A.Inventor: Lucinda C. Paris-Marcano
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Patent number: 5080779Abstract: Methods of diminishing the content of soluble and insoluble forms of iron from crude are disclosed. Crude and water soluble chelant are mixed prior to addition of wash water. After wash water addition, an emulsion is formed. After resolution of the emulsion, iron laden water phase is separated resulting in decreased iron content in the crude. In a two-step desalting process, water soluble chelant is mixed with crude separated from the resolved emulsion emanating from the first, upstream, desalter. After such mixing, fresh wash water is added, with the so-formed crude/chelant/wash water mixture being fed to the second, downstream, desalter, for resolution. Crude separated from the second desalter has substantially diminished iron content compared to crude fed to the first desalter.Type: GrantFiled: August 1, 1990Date of Patent: January 14, 1992Assignee: Betz Laboratories, Inc.Inventors: Spencer S. Awbrey, Ronald W. Gropp
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Patent number: 4992164Abstract: A method of neutralizing chloride ions present in a hydrocarbon medium during processing in a petroleum refinery. Nitrilotriacetic acid or its salt form is injected into the crude charge upstream of the preheat unit. Chloride levels are reduced in this way without the deleterious effects which result from treatment with the conventionally used NaOH.Type: GrantFiled: March 1, 1990Date of Patent: February 12, 1991Assignee: Betz Laboratories, Inc.Inventors: T. Miles McCullough, James G. Edmondson, Joseph J. Perugini
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Patent number: 4988433Abstract: Monobasic carboxylic acids or salts thereof are used to remove metals, particularly calcium and iron, from hydrocarbonaceous feedstocks. An aqueous solution of the acid is used to extract the metals from the feedstock prior to processing. Acetic acid is the preferred carboxylic acid.Type: GrantFiled: May 30, 1990Date of Patent: January 29, 1991Assignee: Chevron Research CompanyInventors: John G. Reynolds, David C. Kramer
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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: 4853110Abstract: A process for removing arsenic and/or selenium from carbonaceous materials. The arsenic and/or selenium are separated by reaction with a metal oxide and/or metal sulfide which is itself derived from a metal complex, and organometallic compound and/or a metal salt of an organic acid which is soluble in said carbonaceous fluid and which either decomposes to the corresponding metal oxide and/or metal sulfide or which can be converted to the corresponding metal sulfide or metal oxide. The reaction of the metal oxide and/or metal sulfide with the arsenic and/or selenium is accomplished at a temperature within the range from about 300.degree. F. to about 800.degree. F. preferably from about 500.degree. F. to about 750.degree. F., most preferably from about 680.degree. F. to about 750.degree. F. and in either an inert or reducing atmosphere. Preferably, the conversion is accomplished in a reducing atmosphere and in the presence of molecular hydrogen.Type: GrantFiled: October 31, 1986Date of Patent: August 1, 1989Assignee: Exxon Research and Engineering CompanyInventors: Gopal H. Singhal, Daniel F. Ryan
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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: 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: 4711713Abstract: A process for enhancement of the cetane number of a diesel fuel which in one embodiment comprises:(1) treating a diesel oil with a nitrogenous treating agent in a nitrogen amount, equivalent on a 100% nitric acid basis, to about 10 weight percent or less of the diesel oil feed;(2) separating unreacted nitrogenous treating agent from the diesel oil of step (1);(3) treating the diesel oil of step (2) with an inorganic alkali to produce a treated diesel oil; and(4) blending the treated diesel oil of step (3) with an untreated diesel oil to produce a blended diesel fuel such that the added nitrogen content in the blended diesel fuel is(a) about 300 ppm or less of nitrogen added when the diesel oil treated in step (1) is obtained from virgin diesel oil stock; or(b) about 450 ppm or less of nitrogen added when the diesel oil treated in step (1) is obtained from hydrotreated diesel oil stock.Type: GrantFiled: February 9, 1987Date of Patent: December 8, 1987Assignee: REI Technologies, Inc.Inventors: Hossein Zarrineghbal, Charles W. Quinlan
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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: 4605489Abstract: A method for reducing the nitrogen content of shale oil is disclosed. The method comprises selectively extracting nitrogen-containing compounds to form a nitrogen-lean raffinate and a nitrogen-rich extract. The nitrogen-lean raffinate is distilled to form a distillate having a further reduced nitrogen content and a bottoms having a further increased nitrogen content. The bottoms is hydrotreated to remove nitrogen-containing compounds. Extracted shale oil compounds may be combined with the bottoms prior to the hydrotreatment or may be used to generate hydrogen gas for the hydrotreatment. Arsenic-containing compounds are removed from the distillate by extraction.Type: GrantFiled: June 27, 1985Date of Patent: August 12, 1986Assignee: Occidental Oil Shale, Inc.Inventor: Ajay Madgavkar
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Patent number: 4477354Abstract: A method is provided for removing polychlorinated biphenyl compounds (PCB) from oil contaminated therewith comprising the steps of extracting said oil with organic solvent, separating the extract, and distilling the solvent from said extract in the presence of a base.Type: GrantFiled: September 7, 1982Date of Patent: October 16, 1984Assignee: Electric Power Research InstituteInventor: William A. Fessler
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Patent number: 4287051Abstract: A method of denitrogenating viscous oils containing a relatively high content of nitrogenous compounds and of disposing of a resulting high nitrogen content oil stream, characterized by forming a raw oil stream and a first viscous bottoms stream that would not be operably pumpable to a partial oxidation unit without the inclusion of viscosity lowering constituents; extracting the nitrogenous compounds from the raw oil stream with an operable acid solvent to produce a raffinate oil of low nitrogen content oil and an extract stream of low viscosity, high nitrogen content oil; recovering the acid solvent from the extract stream, simultaneously producing a small volume stream of low viscosity, high nitrogen content oil; admixing the low viscosity high nitrogen content oil with the high viscosity bottoms stream to provide a pumpable mixed stream; sending the mixed stream to a partial oxidation unit to produce hydrogen; employing the produced hydrogen for hydrogenation of the raffinate oil at mild conditions; and rType: GrantFiled: November 8, 1979Date of Patent: September 1, 1981Assignee: Atlantic Richfield CompanyInventor: Daniel J. Curtin
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Patent number: 4272361Abstract: A method is disclosed for reducing the nitrogen content of shale oil by removing nitrogen-containing compounds from the shale oil. The shale oil containing nitrogen-containing compounds is extracted with a sufficient amount of selective solvent which is selective toward the nitrogen-containing compounds present in the shale oil. The selective solvent comprises an active solvent for nitrogen-containing compounds and water in an amount sufficient to provide phase separation. The active solvent component of the selective solvent is selected from the group consisting of organic acids, and substituted organic acids, particularly acetic, formic and trichloroacetic acids and mixtures thereof. The selective solvent containing the nitrogen-containing compounds is separated from the reduced nitrogen content shale oil raffinate by phase disengagement.Type: GrantFiled: June 27, 1979Date of Patent: June 9, 1981Assignee: Occidental Research CorporationInventor: Leslie E. Compton
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Patent number: 4271009Abstract: Methods are disclosed for reducing the nitrogen content of shale oil by selectively removing therefrom nitrogen-containing compounds. The nitrogen content of shale oil is reduced by a process comprising lowering the viscosity of the shale oil and then contacting the shale oil with a sufficient amount of a solvent which is selective toward the nitrogen-containing compounds present in the shale oil. The selective solvent is selected from the group consisting of organic acids, and substituted organic acids, particularly acetic, formic and trichloroacetic acids and mixtures thereof. The selective solvent system containing the nitrogen-containing compounds is separated from the reduced nitrogen content shale oil raffinate.Type: GrantFiled: June 27, 1979Date of Patent: June 2, 1981Assignee: Occidental Research CorporationInventors: Carole S. Stover, Leslie E. Compton, Eugene G. Youngerman