Organic Acid Patents (Class 208/282)
  • Patent number: 8920633
    Abstract: 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: Grant
    Filed: September 8, 2010
    Date of Patent: December 30, 2014
    Assignee: Cetamax Ventures Ltd.
    Inventors: Kin Meng Chan, Kamalul Arifin Yusof, Shahrul Niza Bin Abdul Rahim, Md Asraff Bin Abdul Karim, Roger Kai Lott
  • Patent number: 8894843
    Abstract: 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: Grant
    Filed: June 11, 2012
    Date of Patent: November 25, 2014
    Assignee: Auterra, Inc.
    Inventors: Jonathan P. Rankin, Jennifer L. Vreeland, Kyle E. Litz, Tracey M. Jordan, Mark N. Rossetti, Eric H. Burnett, Trent A. McCaskill
  • Patent number: 8685233
    Abstract: 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: Grant
    Filed: August 21, 2007
    Date of Patent: April 1, 2014
    Assignee: Dork Ketal Chemicals (I) Private Limited
    Inventor: Mahesh Subramaniyam
  • Patent number: 8672075
    Abstract: 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: Grant
    Filed: March 15, 2012
    Date of Patent: March 18, 2014
    Inventor: Sean H. Walker
  • Publication number: 20130233770
    Abstract: 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: Application
    Filed: November 14, 2011
    Publication date: September 12, 2013
    Applicant: DORF KETAL CHEMICALS (INDIA) PRIVATE LIMITED
    Inventor: Mahesh Subramaniyam
  • Patent number: 8425765
    Abstract: 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: Grant
    Filed: September 9, 2011
    Date of Patent: April 23, 2013
    Assignee: Baker Hughes Incorporated
    Inventors: Lawrence N. Kremer, Jerry J. Weers, Corina Sandu
  • Patent number: 8366915
    Abstract: 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: Grant
    Filed: June 26, 2008
    Date of Patent: February 5, 2013
    Assignee: General Electric Company
    Inventors: Alan E. Goliaszewski, David B. Engel, Roger C. May
  • Publication number: 20120285866
    Abstract: 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: Application
    Filed: July 27, 2012
    Publication date: November 15, 2012
    Inventors: Kyle E. Litz, Jennifer L. Vreeland, Jonathan P. Rankin, Mark N. Rossetti, Tracey M. Jordan, Trent A. McCaskill
  • Patent number: 8298404
    Abstract: 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: Grant
    Filed: September 22, 2010
    Date of Patent: October 30, 2012
    Assignee: Auterra, Inc.
    Inventors: Kyle E. Litz, Jennifer L. Vreeland, Jonathan P. Rankin, Thomas W. DeLancey, Timothy A. Thompson
  • Patent number: 8241490
    Abstract: 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: Grant
    Filed: October 14, 2010
    Date of Patent: August 14, 2012
    Assignee: Auterra, Inc.
    Inventors: Kyle E. Litz, Jennifer L. Vreeland, Jonathan P. Rankin, Mark N. Rossetti, Tracey M. Jordan
  • Patent number: 8197671
    Abstract: 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: Grant
    Filed: December 23, 2010
    Date of Patent: June 12, 2012
    Assignee: Auterra, Inc.
    Inventors: Jonathan P. Rankin, Jennifer L. Vreeland, Kyle E. Litz, Tracey M. Jordan, Mark N. Rossetti, Eric H. Burnett
  • Publication number: 20110309001
    Abstract: The invention relates to a class of novel surfactants that have utility in the recovery and/or extraction of oil.
    Type: Application
    Filed: December 2, 2010
    Publication date: December 22, 2011
    Inventors: David Soane, Rosa Casado Portilla, John H. Dise, Robert P. Mahoney
  • Publication number: 20110192767
    Abstract: 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: Application
    Filed: April 21, 2011
    Publication date: August 11, 2011
    Applicant: GENERAL ELECTRIC COMPANY
    Inventors: Alan E. Goliaszewski, Cato R. McDaniel
  • Publication number: 20110065612
    Abstract: The invention relates to a class of novel surfactants that have utility in the recovery and/or extraction of oil.
    Type: Application
    Filed: December 10, 2009
    Publication date: March 17, 2011
    Inventors: Kristoffer K. Stokes, Michael C. Berg, David Soane, Kevin T. Petersen, John H. Dise, Atul C. Thakrar, Rosa Casado
  • Publication number: 20110031164
    Abstract: 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: Application
    Filed: October 14, 2010
    Publication date: February 10, 2011
    Applicant: AUTERRA INC.
    Inventors: Kyle E. Litz, Jennifer L. Vreeland, Jonathan P. Rankin, Mark N. Rossetti, Tracey M. Jordan
  • Patent number: 7857965
    Abstract: 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: Grant
    Filed: April 4, 2005
    Date of Patent: December 28, 2010
    Assignee: James W. Bunger and Associates Inc.
    Inventors: James W. Bunger, Donald E. Cogswell
  • Patent number: 7799213
    Abstract: 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: Grant
    Filed: July 8, 2005
    Date of Patent: September 21, 2010
    Assignee: Baker Hughes Incorporated
    Inventors: Lawrence N. Kremer, Tran M. Nguyen, Jerry J. Weers
  • Publication number: 20100147739
    Abstract: 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: Application
    Filed: December 4, 2009
    Publication date: June 17, 2010
    Applicant: ExxonMobil Research and Engineering Company
    Inventors: Steven W. LEVINE, Glen B. Brons, George A. Lutz, Daniel P. Leta, Clifford C. Walters
  • Patent number: 7704376
    Abstract: The use of water-soluble aromatic polysulfonic acid salts for inhibiting fouling in process equipment used in the thermal treatment of heavy oils.
    Type: Grant
    Filed: May 12, 2005
    Date of Patent: April 27, 2010
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Ramesh Varadaraj, Michael Siskin, Leo D. Brown, Maa S. Maa
  • Patent number: 7594989
    Abstract: 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: Grant
    Filed: May 12, 2005
    Date of Patent: September 29, 2009
    Assignee: ExxonMobile Research and Engineering Company
    Inventors: Ramesh Varadaraj, Leo D. Brown
  • Patent number: 7419939
    Abstract: 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: Grant
    Filed: June 16, 2004
    Date of Patent: September 2, 2008
    Assignee: ExxonMobil Upstream Research Company
    Inventor: Ramesh Varadaraj
  • Patent number: 7117722
    Abstract: 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: Grant
    Filed: October 12, 2004
    Date of Patent: October 10, 2006
    Assignee: ExxonMobil Research and Engineering Company
    Inventor: Ramesh Varadaraj
  • Patent number: 6875341
    Abstract: 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: Grant
    Filed: May 23, 2000
    Date of Patent: April 5, 2005
    Assignee: James W. Bunger and Associates, Inc.
    Inventors: James W. Bunger, Donald E. Cogswell
  • Publication number: 20040232051
    Abstract: 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: Application
    Filed: June 4, 2004
    Publication date: November 25, 2004
    Inventor: Ramesh Varadaraj
  • Patent number: 6800193
    Abstract: 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: Grant
    Filed: March 28, 2001
    Date of Patent: October 5, 2004
    Assignee: ExxonMobil Upstream Research Company
    Inventor: Ramesh Varadaraj
  • Patent number: 6673238
    Abstract: 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: Grant
    Filed: November 8, 2001
    Date of Patent: January 6, 2004
    Assignee: ConocoPhillips Company
    Inventors: Bruce W. Gerhold, Joseph E. Bares, Scott D. Love, Jerry G. Feierabend
  • Publication number: 20030132139
    Abstract: The invention describes a method for decreasing the viscosity of crude oils and residuum utilizing a combination of acid and sonic treatment.
    Type: Application
    Filed: January 21, 2003
    Publication date: July 17, 2003
    Inventor: Ramesh Varadaraj
  • Patent number: 6544411
    Abstract: The invention describes a method for decreasing the viscosity of crude oils and residuum utilizing a combination of acid and sonic treatment.
    Type: Grant
    Filed: March 9, 2001
    Date of Patent: April 8, 2003
    Assignee: ExxonMobile Research and Engineering Co.
    Inventor: Ramesh Varadaraj
  • Patent number: 6102379
    Abstract: 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: Grant
    Filed: November 17, 1997
    Date of Patent: August 15, 2000
    Assignee: Hytec, Inc.
    Inventors: Eric R. Ponslet, William O. Miller
  • Patent number: 6048904
    Abstract: 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: Grant
    Filed: December 1, 1998
    Date of Patent: April 11, 2000
    Assignee: Exxon Research and Engineering Co.
    Inventors: Irwin A. Wiehe, Ramesh Varadaraj, Torris G. Jermansen, Raymond J. Kennedy, Cornelius H. Brons
  • Patent number: 5925233
    Abstract: 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: Grant
    Filed: October 14, 1997
    Date of Patent: July 20, 1999
    Assignee: Clariant GmbH
    Inventors: Dennis Miller, Axel Vollmer, Michael Feustel
  • Patent number: 5282959
    Abstract: 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: Grant
    Filed: March 16, 1992
    Date of Patent: February 1, 1994
    Assignee: Betz Laboratories, Inc.
    Inventors: Paul V. Roling, Cato R. McDaniel
  • Patent number: 5152886
    Abstract: 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: Grant
    Filed: October 31, 1990
    Date of Patent: October 6, 1992
    Assignee: Laboratorios Paris, C.A.
    Inventor: Lucinda C. Paris-Marcano
  • Patent number: 5080779
    Abstract: 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: Grant
    Filed: August 1, 1990
    Date of Patent: January 14, 1992
    Assignee: Betz Laboratories, Inc.
    Inventors: Spencer S. Awbrey, Ronald W. Gropp
  • Patent number: 4992164
    Abstract: 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: Grant
    Filed: March 1, 1990
    Date of Patent: February 12, 1991
    Assignee: Betz Laboratories, Inc.
    Inventors: T. Miles McCullough, James G. Edmondson, Joseph J. Perugini
  • Patent number: 4988433
    Abstract: 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: Grant
    Filed: May 30, 1990
    Date of Patent: January 29, 1991
    Assignee: Chevron Research Company
    Inventors: John G. Reynolds, David C. Kramer
  • Patent number: 4960508
    Abstract: 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: Grant
    Filed: January 30, 1989
    Date of Patent: October 2, 1990
    Assignee: Shell Oil Company
    Inventor: Wayne E. Evans
  • Patent number: 4853110
    Abstract: 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: Grant
    Filed: October 31, 1986
    Date of Patent: August 1, 1989
    Assignee: Exxon Research and Engineering Company
    Inventors: Gopal H. Singhal, Daniel F. Ryan
  • Patent number: 4749472
    Abstract: 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: Grant
    Filed: March 6, 1987
    Date of Patent: June 7, 1988
    Assignee: Shell Oil Company
    Inventor: Ajay M. Madgavkar
  • Patent number: 4746420
    Abstract: 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: Grant
    Filed: February 24, 1986
    Date of Patent: May 24, 1988
    Assignee: REI Technologies, Inc.
    Inventors: Saeed T. Darian, Sayed-Hamid Arabshahi
  • Patent number: 4743360
    Abstract: 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: Grant
    Filed: October 23, 1986
    Date of Patent: May 10, 1988
    Assignee: Labofina, S.A.
    Inventors: Michel Melin, Jacques F. Grootjans, Andre Vanderlinden
  • Patent number: 4731174
    Abstract: 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: Grant
    Filed: June 24, 1987
    Date of Patent: March 15, 1988
    Assignee: Union Oil Company of California
    Inventors: Mario L. Occelli, Edward J. Aitken
  • Patent number: 4711713
    Abstract: 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: Grant
    Filed: February 9, 1987
    Date of Patent: December 8, 1987
    Assignee: REI Technologies, Inc.
    Inventors: Hossein Zarrineghbal, Charles W. Quinlan
  • Patent number: 4623444
    Abstract: 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: Grant
    Filed: June 27, 1985
    Date of Patent: November 18, 1986
    Assignee: Occidental Oil Shale, Inc.
    Inventors: Stanley C. Che, Ajay Madgavkar
  • Patent number: 4605489
    Abstract: 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: Grant
    Filed: June 27, 1985
    Date of Patent: August 12, 1986
    Assignee: Occidental Oil Shale, Inc.
    Inventor: Ajay Madgavkar
  • Patent number: 4477354
    Abstract: 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: Grant
    Filed: September 7, 1982
    Date of Patent: October 16, 1984
    Assignee: Electric Power Research Institute
    Inventor: William A. Fessler
  • Patent number: 4287051
    Abstract: 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 r
    Type: Grant
    Filed: November 8, 1979
    Date of Patent: September 1, 1981
    Assignee: Atlantic Richfield Company
    Inventor: Daniel J. Curtin
  • Patent number: 4272361
    Abstract: 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: Grant
    Filed: June 27, 1979
    Date of Patent: June 9, 1981
    Assignee: Occidental Research Corporation
    Inventor: Leslie E. Compton
  • Patent number: 4271009
    Abstract: 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: Grant
    Filed: June 27, 1979
    Date of Patent: June 2, 1981
    Assignee: Occidental Research Corporation
    Inventors: Carole S. Stover, Leslie E. Compton, Eugene G. Youngerman