Patents Represented by Attorney, Agent or Law Firm Linda M. Scuorzo
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Patent number: 5635056Abstract: The present invention relates to a continuous in-situ process for the removal from heavy oils, of organically bound sulfur in the form of mercaptans, sulfides and thiophenes, heteroatoms selected from the group consisting of nitrogen and oxygen and metals selected from the group consisting of nickel, vanadium and iron, comprising the steps of (a) contacting a heavy oil with aqueous sodium hydroxide at a temperature of about 380.degree. to about 450.degree. C. for a time sufficient to form sodium sulfide; (b) contacting said sodium sulfide of step (a) with water and a transition metal for a time and at a temperature sufficient to form transition metal sulfide, sodium hydroxide, hydrogen and impurities; and (c) recirculating said sodium hydroxide from step (b) to step (a) and removing said transition metal sulfide and said impurities, wherein said impurities are iron, vanadium and nickel. Optionally, molecular hydrogen may be added in the first step.Type: GrantFiled: May 2, 1995Date of Patent: June 3, 1997Assignee: Exxon Research and Engineering CompanyInventors: Glen Brons, Ronald D. Myers
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Patent number: 5627225Abstract: This invention provides for novel road paving binder compositions and the method of making them. One embodiment is a road paving binder composition of a storage stable blend of a sulfonated, unhydrogenated random copolymer of styrene and butadiene having a sulfonation level of from 1 to 100 meq S0.sub.3 H/100 g of polymer and a sulfonated asphalt. Another is a method of making a storage stable polymer modified asphalt composition by combining a sulfonated unhydrogenated random styrene butadiene copolymer having a sulfonation level of from about 1 to 100 meq S0.sub.3 H per 100 g of polymer and a sulfonated asphalt at a temperature of at least about 180.degree. C. to produce a storage stable polymer modified asphalt. Yet another is a method of making a storage stable polymer modified asphalt by combining a sulfonated unhydrogenated random styrene and butadiene copolymer having a sulfonation level of from about 1 to 100 meq S0.sub.Type: GrantFiled: October 31, 1995Date of Patent: May 6, 1997Assignee: Exxon Research and Engineering CompanyInventors: Martin L. Gorbaty, Christian G. Lenoble, Nicholas C. Nahas, Dennis G. Peiffer
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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: 5611915Abstract: A process for heteroatom removal-enhancing hydrogenation of highly refractory aromatic ring structures that involves contacting a highly refractory structure having at least one aryl linkage connecting a first heteroaryl moiety and a moiety selected from the group consisting of an aryl moiety and a second heteroaryl moiety with supercritical water having a temperature of from about 400.degree. C. to about 600.degree. C. in the presence of from about 3.4 MPa to about 18.6 MPa of CO to produce lower molecular weight products having decreased aromatic and heteroatom content. The process has utility for producing more valuable lower molecular weight products having a reduced aromatic heteroatom content from starting materials that are highly refractory and widely considered to be difficult to upgrade such as coals and asphaltenes, and model compounds containing the biaryl linkages.Type: GrantFiled: January 5, 1996Date of Patent: March 18, 1997Assignee: Exxon Research and Engineering CompanyInventors: Michael Siskin, David T. Ferrughelli, Alan R. Katritzky, William N. Olmstead
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Patent number: 5600017Abstract: The invention is a process for hydroformylating multicomponent syngas feed streams containing CO, H.sub.2, C.sub.2 to C.sub.5 olefins and mixtures thereof and C.sub.2 to C.sub.5 alkynes and mixtures thereof by contacting the multicomponent syngas feed stream with a solution of an oil soluble rhodium complex catalyst produced by complexing in solution a low valence Rh and an oil soluble triorganophoshorous compound wherein the catalyst has a P/Rh ratio of at least 30, a concentration of Rh in solution from about 1 to about 1000 ppm by weight, a total concentration of coordinatively active P of at least about 0.01 mol/l, and a ratio of [P]/p.sub.co of at least 0.1 mmol/l/kPa, wherein [P] is the total concentration of coordinatively active phosphorous in the solution, and p.sub.co is the partial pressure of CO, to produce the corresponding C.sub.3 to C.sub.6 aldehydes. The process has utility for the hydroformylation of streams that contain olefins and alkynes.Type: GrantFiled: November 28, 1995Date of Patent: February 4, 1997Assignee: Exxon Research and Engineering CompanyInventors: Gabor Kiss, Michael G. Matturro, Harry W. Deckman, Istvan T. Horvath, Anthony M. Dean, Frank Hershkowitz, Raymond A. Cook
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Patent number: 5569404Abstract: The present invention provides for the use of certain oil soluble iodides to enhance the oxidation resistance of lubricating oils and fuels, and for the novel formulated compositions containing these iodides. Oil soluble iodides such as C.sub.16 to C.sub.78 alkyl ammonium as well as oil solubilizable or dispersible iodides such as CoI.sub.2, CuI, KI and NaI in combination with a suitable dispersing agent may be used. Typically a minor amount of additive, from about 40 to about 1000 ppm is used. The additive is effective as an antioxidant in a variety of different types of base and formulated oils.Type: GrantFiled: February 17, 1995Date of Patent: October 29, 1996Assignee: Exxon Research and Engineering CompanyInventors: Manuel A. Francisco, Kenneth D. Rose
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Patent number: 5549744Abstract: The present invention provides for a method of making storage stable road paving binders by blending a minor amount of a polymer having at least one diene monomer with a major amount of asphalt containing at least 0.3% by weight of total nitrogen at an elevated temperature such that the components are sufficiently fluid to blend; treating the asphalt-polymer blend using not more than 250 meq of a sulfonating agent per 100 g of asphalt-polymer blend to introduce the corresponding acid functionality into the blend; maintaining the sulfonated asphalt-polymer blend at a sufficiently elevated temperature and stripping the sulfonated blend with sufficient chemically unreactive gas to remove a major fraction of the acid functionality introduced by sulfonation. The invention also provides for the compositions made by the process. These are useful as binders in road paving applications.Type: GrantFiled: September 8, 1995Date of Patent: August 27, 1996Assignee: Exxon Research and Engineering CompanyInventors: Olga Puzic, Larry J. Evers, Kenneth E. Williamson, Martin L. Gorbaty, Nicholas C. Nahas
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Patent number: 5529684Abstract: The present invention provides for a method of decreasing the metals content of metal containing petroleum streams by forming a mixture of the petroleum fraction containing those metals and an essentially aqueous electrolysis medium, and passing an electric current through the mixture at a voltage, pH and time sufficient to remove the metals such as Ni, V and Fe from the stream (i.e. to produce a petroleum fraction having decreased content of the metals). The cathodic voltage is from 0 V to -3.0 V vs. SCE at a pH of from 6 to 14, preferably 7 to 14, most preferably above 7 to 14.The invention provides a method for enhancing the value of petroleum feeds that traditionally have limited use in refineries due to their Ni and V content.Type: GrantFiled: May 12, 1995Date of Patent: June 25, 1996Assignee: Exxon Research and Engineering CompanyInventors: Mark A. Greaney, Michael C. Kerby, Jr., William N. Olmstead, Irwin A. Wiehe
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Patent number: 5520722Abstract: The invention is a process for the preferential removal of a variable amount of alkynes and multiunsaturates from a gas stream containing at least hydrogen, olefins, alkynes, and multiunsaturates by contacting a gas stream containing H.sub.2, olefins, alkynes and multiunsaturates with a metal complex-containing stream selected from the group consisting of liquids and slurries, at conditions sufficient to form multiunsaturate adducts of the metal complex, by introducing the metal complex stream at a rate sufficient to form stoichiometric adducts of the alkynes and multiunsaturates to be removed, and removing the alkyne and multiunsaturate adducts of the metal complex. The invention has utility for removal of multiunsaturates from multicomponent syngas streams.Type: GrantFiled: January 18, 1995Date of Patent: May 28, 1996Assignee: Exxon Research and Engineering CompanyInventors: Frank Hershkowitz, Gabor Kiss
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Patent number: 5514252Abstract: The present invention provides a method for decreasing the Conradson carbon ("Concarbon") number of petroleum feedstreams by passing an electric current through a mixture of a petroleum stream, typically having a Conradson carbon residue of at least about 0.1% and an aqueous electrolysis medium at a pH and cathodic voltage for a time sufficient to decrease the Conradson carbon number of the petroleum stream. The electrolysis medium contains quaternary carbyl or hydrocarbyl onium salts; inorganic hydroxides such as NaOH or KOH, or mixtures thereof. A cathodic voltage of 0 V to -3.0 V vs. Saturated Calomel Electrode (SCE) and a pH of 6-14, preferably 7 to 14, more preferably above 7 to 14 are used.The invention has utility for converting less economically desirable refinery feeds to feeds that are more valuable.Type: GrantFiled: May 12, 1995Date of Patent: May 7, 1996Assignee: Exxon Research and Engineering CompanyInventors: Michael C. Kerby, Jr., Mark A. Greaney, Carl W. Hudson
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Patent number: 5503643Abstract: The fuel oil-substituted fullerene compositions of the invention are useful for improving the cold flow properties of fuels. Typically the substituted fullerenes have the general formula C.sub.Fn (GRy)x, where C.sub.Fn is a fullerene, n is the number of carbon atoms in the fullerene, x is an integer from 1 up to the maximum number of sites on the fullerene molecule available for adding substituent groups, G is a linking group that may be absent or present, and when present is an oxygen, sulfur, nitrogen, phenol, aniline, Mannich base or diazocarboxylate-derived group, y is an integer determined by the identity of G, and when y equals 1 R is a substituted or unsubstituted hydrocarbyl group and when y equals 2 at most one R may be hydrogen while the remainder are hydrocarbyl groups, and the R group may be the same or different, and wherein when x is greater than 1 the GRy may be the same or different and at most one R may be hydrogen.Type: GrantFiled: June 7, 1995Date of Patent: April 2, 1996Assignee: Exxon Research and Engineering CompanyInventors: George W. Schriver, Abhimanyu O. Patil, David J. Martella, Kenneth Lewtas
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Patent number: 5504262Abstract: The present invention relates to a method for making mixtures of ethanol and methanol by reacting methane, water and an acidic aqueous solution of a electron acceptor, preferably Fe.sub.2 (SO.sub.4).sub.3 or Fe(ClO.sub.4).sub.3, having a pH of less than 3, preferably 1 to 3, more preferably 1 to 2 in the presence of a noble metal catalyst, typically platinum or palladium, having a diameter of at least about 100 .ANG. at a temperature of at least 60.degree. C. to about 100.degree. C. The process is advantageous as it provides a method of making ethanol directly from methanol at low cost and high thermodynamic efficiency.Type: GrantFiled: December 23, 1994Date of Patent: April 2, 1996Assignee: Exxon Research & Engineering Co.Inventors: Thomas H. Vanderspurt, John J. Knarr, Anthony W. Ho
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Patent number: 5493064Abstract: The present invention discloses an alcohol coupling process in which a vaporized mixture of starting alcohols, preferably methanol and ethanol, is reacted with syngas in the presence of a large pore L zeolite, Y zeolite or large port mordenite, to form at least one alcohol coupling product having a greater number of carbon atoms than all of the starting alcohols. The large pore zeolite preferably has a substantial absence of strongly acidic catalytic sites and the reaction preferably produces the product alcohol in the substantial absence of C.sub.6+ oxygenates.Type: GrantFiled: December 13, 1994Date of Patent: February 20, 1996Assignee: Exxon Research and Engineering CompanyInventors: Thomas H. Vanderspurt, Jar-Lin Kao
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Patent number: 5463082Abstract: Stoichiometric and catalytic chemical transformations may be carried out in solution using novel fluorous multiphase systems (FMS). The term "fluorous" is defined as a carbon-fluorine bond rich organic molecule. The FMS consists of a fluorous phase containing a fluorous solvent, typically a fluorocarbon or a fluorohydrocarbon and a reagent or a catalyst containing a sufficient number of fluorous moieties to render it preferentially soluble in the fluorous solvent without impairing the ability of the catalyst or reagent to be effective in the reaction and while maintaining the reaction in a liquid or fluid phase. The nonfluorous solvent may be any suitable organic or nonorganic solvent(s) with limited or no solubility in the fluorous solvent that is effective for dissolving the reactant(s) and most desirably, for separating the resulting product(s). Typically, such solvents have a Hildebrand solubility parameter of at least about 18.0 MPa1/2.Type: GrantFiled: July 8, 1993Date of Patent: October 31, 1995Assignee: Exxon Research and Engineering CompanyInventors: Istvan T. Horvath, Jozsef Rabai
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Patent number: 5462680Abstract: This invention relates to novel compositions of matter comprising free radical adducts of a fullerene with one or more saturated hydrocarbons having a number average molecular weight ranging from about 200 to about ten million. Attachment of saturated hydrocarbons to as many as fourteen sites on the fullerene surface can be achieved via free radical initiated reactions. Fullerenes also add to saturated hydrocarbons with functional groups selected from the group consisting of hydroxy, carboxy, and carboalkoxy radicals in the presence of a free radical initiator. Said radical adducts of substantially saturated hydrocarbons with fullerenes react further with alkylamines and polyamines to produce new compositions. The radical adducts, and their aminated derivatives are useful as dispersants and viscosity modifiers in lubricants.Type: GrantFiled: April 19, 1994Date of Patent: October 31, 1995Assignee: Exxon Research & Engineering Co.Inventors: Stanley J. Brois, Abhimanyu O. Patil, Wolfgang W. Schulz, Chang S. Hsu, Richard T. Garner
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Patent number: 5453561Abstract: The invention concerns a method for reactive separation of mixtures containing hydrocarbons and oxygenated hydrocarbons, by contacting a mixture of hydrocarbons such as C.sub.2 to C.sub.26 hydrocarbons and mixtures thereof and oxygenated hydrocarbons, such as C.sub.2 to C.sub.40 oxygenated hydrocarbons and mixtures thereof to form a mixture of hydrocarbons and lower molecular weight oxygenated hydrocarbons and heating the mixture in water at temperature typically from about and pressure sufficient to cleave the oxygenated hydrocarbons to lower molecular weight products to form a liquid layer containing water soluble reaction products and an organic layer containing primarily hydrocarbons.Type: GrantFiled: January 27, 1994Date of Patent: September 26, 1995Assignee: Exxon Research & Engineering Co.Inventors: Ramzi Y. Saleh, Michael Siskin, Glen B. Brons, Stephen N. Vaughn, Richard H. Schlosberg
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Patent number: 5403964Abstract: The present invention relates to enhanced process for converting certain ethers, such as sec-butyl ether and isopropyl ether to their corresponding reaction products in the presence of water. This may be accomplished by adding a rate enhancing surfactant, such as an anionic or cationic surfactant to a mixture of the ether and water, preferably least about 10.sup.-5 molar surfactant. Under those conditions the reaction shows an increase in reaction rate over the rate of the process wherein surfactant is not used.Type: GrantFiled: January 27, 1994Date of Patent: April 4, 1995Assignee: Exxon Research & Engineering Co.Inventors: Ramzi Y. Saleh, Joel R. Livingston, Jr., Michael Siskin, Glen B. Brons
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Patent number: 5372798Abstract: The invention relates to a composition that is the reaction of a fullerene containing at least one corrannulene ring structure and Y.sub.2 X.sub.2, wherein Y is Se or S, and X is Cl or Br. Generally, these compounds may be represented by the formula C.sup.f.sub.n X.sub.6 Y.sub.2 or more particularly C.sup.f.sub.n X.sub.5 (YYX). In the formula C.sup.f.sub.n more specifically, is a fullerene having at least one corrannulene ring structure. The compositions may be made by reacting fullerenes with Se.sub.2 X.sub.2 or S.sub.2 X.sub.2 wherein X is Cl or Br, preferably in liquid form and preferably heated for a time sufficient to produce the novel compositions. The compositions may be isolated in crystalline form by precipitation with a solvent such as hexane. In crystalline form the compositions may be represented by the generic formula C.sup.f.sub.n X.sub.8 Y.sub.4, or more particularly, C.sup.f.sub.n X.sub.5 (YYX).mY.sub.2 X.sub.2 because in crystalline form the compositions are typically associated with .mY.sub.Type: GrantFiled: March 8, 1994Date of Patent: December 13, 1994Assignee: Exxon Research and Engineering CompanyInventors: Jonathan M. McConnachie, Edward I. Stiefel
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Patent number: 5354916Abstract: The invention relates to a process for selectively producing alkyl halides from alkanes, such as methane and ethane at low temperatures and low pressures. Optional hydrolysis to the corresponding alcohols may follow. The process involves adding an alkane and an added halogen source to an aqueous solution in a homogeneous system in the presence of a transition metal halide containing complex, for a time, under conditions and in effective amounts that will permit the formation of alkyl monohalides.Type: GrantFiled: January 24, 1994Date of Patent: October 11, 1994Assignee: Exxon Research and Engineering CompanyInventors: Istvan T. Horvath, John M. Millar, Raymond A. Cook
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Patent number: 5348994Abstract: Disclosed in this invention are novel road paving binder compositions and the method of making same. The compositions are made by combining an asphalt that contains sulfonate or sulfonic acid groups, a polymer preferably of butyl rubbers, styrene-butadiene linear diblock polymer, styrene-butadiene-styrene linear or radial triblock polymer and EPDM that has been sulfonated, and mixtures thereof, and a basic neutralizing agent that contains cations having a valence from +1 to +3. The amounts of each are effective to allow formation of one continuous phase or two interdispersed phases that do not segregate on standing at elevated temperatures associated with road paving. The amount of polymer is an amount less than 7 wt. % of total polymer-asphalt composition that is sufficient to produce an asphaltic composition having a viscosity at 135.degree. C. in the range of from about 150 cPs to about 2000 cPs or from about 3000 cPs to about 8000 cPs.Type: GrantFiled: April 1, 1993Date of Patent: September 20, 1994Assignee: Exxon Research & Engineering Co.Inventors: Martin L. Gorbaty, Dennis G. Peiffer, Daniel J. McHugh