Organic Acid Or Phenol Contaminant Removal Patents (Class 208/263)
  • Patent number: 4504378
    Abstract: A process for reducing the molecular weight of hydrocarbons using NaAlCl.sub.4 is provided wherein the hydrogen to carbon ratio of the product slate is approximately the same as the feed material, comprising contacting the feed material with a molten salt of NaAlCl.sub.4 having a ratio of aluminum chloride to sodium chloride of at least 1:1, preferably at a temperature of at least 660.degree. F., and at a pressure above atmospheric, preferably from about 50 psia to about 2000 psia, depending upon the product slate desired. According to the present invention, heavy hydrocarbons are converted to a liquid product slate wherein substantially all of the liquid components exhibit a molecular weight lower than the molecular weight range exhibited by the hydrocarbon feedstock.
    Type: Grant
    Filed: February 18, 1983
    Date of Patent: March 12, 1985
    Assignee: Marathon Oil Company
    Inventor: Mark A. Plummer
  • Patent number: 4451356
    Abstract: Phenolic compounds are dehydroxylated in the vapor phase by contacting with a reducing atmosphere substantially comprising hydrogen sulfide as the reducing agent in the presence of a sulfur-tolerant metal sulfide catalyst. The additional presence of hydrogen gas helps to desulfurize the catalyst and maintain catalytic activity. The process is useful in the treatment of phenolic naphtha fractions present in coal liquids, produced by pyrolysis or direct coal liquefaction.
    Type: Grant
    Filed: April 23, 1982
    Date of Patent: May 29, 1984
    Assignee: Exxon Research and Engineering Co.
    Inventors: Wim J.M. Pieters, Gerard M. Prilutski
  • Patent number: 4414102
    Abstract: The nitrogen-containing and oxygen-containing contaminants of a mineral oil are converted to the corresponding sulfur compounds by contacting the oil with a fresh catalyst containing metals from Groups VB, VIB and VIII or a deactivated and metals contaminated hydrodesulfurization catalyst in the presence of hydrogen and hydrogen sulfide under conditions of elevated temperature and pressure.
    Type: Grant
    Filed: May 15, 1981
    Date of Patent: November 8, 1983
    Assignee: Mobil Oil Corporation
    Inventors: Lillian A. Rankel, Leslie R. Rudnick
  • Patent number: 4406780
    Abstract: Properties of phenol-containing hydrocarbonaceous streams are improved by first treating the stream with a C.sub.1 to C.sub.10 alcohol and an acid. If enough alcohol and acid are employed, two liquid phases are formed, an alcohol/acid phase and a hydrocarbonaceous phase. The alcohol/acid phase, which now contains phenols, can be separated and contacted with a C.sub.1 to C.sub.16 olefin or the olefin can be added in situ. In any case, oxygen-alkylation of the phenolic groups occurs.
    Type: Grant
    Filed: August 18, 1981
    Date of Patent: September 27, 1983
    Assignee: Exxon Research and Engineering Co.
    Inventors: Kenneth A. Gould, Robert B. Long
  • Patent number: 4382855
    Abstract: Removal of hydroxy-substituted and/or mercapto-substituted-hydrocarbons from coal liquids which comprises contacting the coal liquids with an aqueous composition containing an alkanolamine, thereby providing a two-phase mixture, and then separating the mixture into an aqueous extract phase and a naphtha rich raffinate phase.
    Type: Grant
    Filed: October 28, 1981
    Date of Patent: May 10, 1983
    Assignee: Ashland Oil, Inc.
    Inventors: Clifford Ward, Charles A. Johnson, III
  • Patent number: 4326949
    Abstract: A method for separating phenols from phenol-containing streams and converting them to ethers by: (a) contacting the phenol-containing stream with a multivalent metal composition capable of forming hydroxy metal phenates with the phenols from the stream; (b) separating the hydroxy metal phenate from the stream; and (c) reacting the hydroxy metal phenate with one or more quaternary Group VA compounds represented by the formula R.sub.3 R'MOR" or R.sub.3 R'MX.
    Type: Grant
    Filed: October 24, 1980
    Date of Patent: April 27, 1982
    Assignee: Exxon Research & Engineering Co.
    Inventor: Richard H. Schlosberg
  • Patent number: 4319981
    Abstract: A process for preparing a liquid fuel composition which comprises liquefying coal, separating a mixture of phenols from said liquefied coal, converting said phenols to the corresponding mixture of anisoles, subjecting at least a portion of the remainder of said liquefied coal to hydrotreatment, subjecting at least a portion of said hydrotreated liquefied coal to reforming to obtain reformate and then combining at least a portion of said anisoles and at least a portion of said reformate to obtain said liquid fuel composition.
    Type: Grant
    Filed: November 12, 1980
    Date of Patent: March 16, 1982
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventor: Gary M. Singerman
  • Patent number: 4299691
    Abstract: Phenols are separated from phenol-containing hydrocarbonaceous streams by use of multivalent metal oxides and/or hydroxides whereupon the resulting hydroxy metal phenate is reacted with one or more alcohols selected from the group consisting of the C.sub.1 to C.sub.10 aliphatic primary alcohols and the C.sub.7 to C.sub.16 arylalkyl primary alcohols.
    Type: Grant
    Filed: November 5, 1980
    Date of Patent: November 10, 1981
    Assignee: Exxon Research & Engineering Co.
    Inventors: Herbert W. Dougherty, Richard H. Schlosberg
  • Patent number: 4293404
    Abstract: The phenolic oxygen and/or the thiol sulfur present in the polycyclic aromatic compounds in a heavy oil, such as vacuum pipestill bottoms, crude oil, reduced crude, residual oil or tar sands oil, can be removed as H.sub.2 O and/or H.sub.2 S by contacting the heavy oil with a hydrogen donor at an elevated temperature in the presence of a specified catalyst.
    Type: Grant
    Filed: July 21, 1980
    Date of Patent: October 6, 1981
    Assignee: Mobil Oil Corporation
    Inventors: Malvina Farcasiu, Darrell D. Whitehurst
  • Patent number: 4277327
    Abstract: Phenol-containing streams are treated by an oxygen-alkylation process to convert substantially all of the phenol groups to ether groups. The oxygen-alkylation process comprises contacting the phenol-containing stream, preferably a coal liquid, with (a) a basic solution comprising one or more oxides or hydroxides of a metal selected from the group consisting of alkali and alkaline-earth metals; and (b) an alkylating agent represented by the formula RX where R is a C.sub.1 to C.sub.18 alkyl, allyl, cycloalkyl, haloalkyl, benzyl or arylalkyl group provided X is located on the alkyl portion of the compound and X is sulfate or a halide selected from the group consisting of chlorine, bromine and iodine.
    Type: Grant
    Filed: November 19, 1979
    Date of Patent: July 7, 1981
    Assignee: Exxon Research & Engineering Co.
    Inventors: Richard H. Schlosberg, Martin L. Gorbaty
  • Patent number: 4277326
    Abstract: Process for improving properties of phenol-containing hydrocarbonaceous streams such as a coal liquid by contacting stream with (a) a multivalent metal composition selected from the group consisting of oxides and/or hydroxides of multivalent metals capable of forming hydroxy metal phenates with the phenols of the stream; and (b) one or more alkylating agents represented by the formula RX where R is a C.sub.1 to C.sub.18 group selected from the group consisting of alkyl, allyl, cycloalkyl, haloalkyl, benzyl, and arylalkyl, provided X is located on the alkyl portions of the alkylating agent and X is sulfate or a halide.
    Type: Grant
    Filed: November 19, 1979
    Date of Patent: July 7, 1981
    Assignee: Exxon Research & Engineering Co.
    Inventors: Richard H. Schlosberg, Charles G. Scouten
  • Patent number: 4256568
    Abstract: Process for removing phenols from phenol-containing streams such as coal liquids by contacting the stream with a multivalent metal composition selected from the group consisting of oxides and/or hydroxides of one or more multivalent metals capable of forming a hydroxy metal phenate with the phenols of the stream; separating the hydroxy metal phenate from the treated stream; and heating the hydroxy metal phenate to its decomposition temperature, thereby forming phenols and oxides of the multivalent metal.
    Type: Grant
    Filed: November 19, 1979
    Date of Patent: March 17, 1981
    Assignee: Exxon Research & Engineering Co.
    Inventors: Richard H. Schlosberg, Charles G. Scouten
  • Patent number: 4199440
    Abstract: An improved process is disclosed for removing trace acidic compounds from liquid hydrocarbons. Traces of acidic compounds, including carboxylic acids, H.sub.2 S, naphthenic acids, et al., are present in most hydrocarbon streams. The presence of these acidic compounds is considered deleterious to accepted product specifications. The trace acidic compounds which interfere are removed via injection of a dilute aqueous alkaline solution into the hydrocarbon stream and passage of this stream through a coalescing bed.
    Type: Grant
    Filed: August 24, 1978
    Date of Patent: April 22, 1980
    Assignee: UOP Inc.
    Inventor: Thomas A. Verachtert
  • Patent number: 4162902
    Abstract: A process for removing phenols from waste water resulting from the gasification or carbonization of coal and containing CO.sub.2, H.sub.2 S and NH.sub.3, comprising mixing the waste water with a low-boiling organic solvent, separating the mixture into a solvent layer and an aqueous layer, stripping off from the aqueous layer under superatmospheric pressure the vapors of CO.sub.2, H.sub.2 S and organic solvent contained therein, then stripping off from the aqueous layer the NH.sub.3 contained therein leaving a refined aqueous product layer suitable for discharge, scrubbing the stripped vapors under superatmospheric pressure with a portion of the cold refined product to remove organic solvent contained therein, condensing part of the solvent and separating it under superatmospheric pressure, and scrubbing the remaining acid gases still containing ammonia and solvent with recirculated cooled raw phenol to remove the ammonia and solvent.
    Type: Grant
    Filed: September 30, 1977
    Date of Patent: July 31, 1979
    Assignee: Metallgesellschaft Aktiengesellschaft
    Inventors: Paul Wiesner, Hans-Martin Stonner
  • Patent number: 4133646
    Abstract: An improved two-stage coal liquefaction process is provided, wherein solvent-boiling range phenolics, produced in the solubilization of the coal feed, are removed wholly or partially from recycle solvent at some point in the process prior to recycle to the first stage to control the level of phenolics in both stages of the process. The two-stage process involves a mild short contact time first stage operation, the removal of inorganic sulfur, ash and coal solids followed by a second stage operation, the severity of which is controlled as a function of the final product desired.
    Type: Grant
    Filed: June 29, 1977
    Date of Patent: January 9, 1979
    Assignee: Electric Power Research Institute, Inc.
    Inventors: Malvina Farcasiu, Thomas O. Mitchell, Darrell Duayne Whitehurst
  • Patent number: 4125452
    Abstract: In a process for the liquefaction of coal in which coal liquids containing phenols and other oxygenated compounds are produced during the liquefaction step and later hydrogenated, oxygenated compounds are removed from at least part of the coal liquids in the naphtha and gas oil boiling range prior to the hydrogenation step and employed as a feed stream for the manufacture of a synthesis gas or for other purposes.
    Type: Grant
    Filed: June 10, 1977
    Date of Patent: November 14, 1978
    Assignee: Exxon Research & Engineering Co.
    Inventor: Edward Effron
  • Patent number: 4070271
    Abstract: A process is disclosed for the catalytic oxidation of mercaptans in a sour petroleum distillate containing difficultly oxidizable mercaptans, catalyst toxins and catalyst toxin precursors.
    Type: Grant
    Filed: March 4, 1977
    Date of Patent: January 24, 1978
    Assignee: UOP Inc.
    Inventors: David H. J. Carlson, Peter Urban
  • Patent number: 4056462
    Abstract: The instant invention relates to a process for separating components from liquid mixtures which comprises emulsifying said liquid mixture in an immiscible liquid which is characterized as a solvent for the components. The emulsion is then contacted with an inert gas whereby the components of the mixture, because of their solubility, permeate into said immiscible liquid, and are stripped therefrom by the inert gas. The components may then be separated from said inert gas stream by condensation and subsequent phase separation or fractionation, by absorption, distillation or by adsorption. In a preferred embodiment of the instant invention the liquid mixture comprises a hydrocarbon which is emulsified in an aqueous surfactant containing liquid. The hydrocarbon containing mixture contains hydrocarbons of different types, as well as hydrocarbons mixed with oxygenated compounds, i.e. alcohols, ketones, acids, and mixtures thereof.
    Type: Grant
    Filed: July 25, 1973
    Date of Patent: November 1, 1977
    Assignee: Exxon Research and Engineering Company
    Inventors: Norman N. Li, Robert P. Cahn
  • Patent number: 4049543
    Abstract: A mixture of petroleum acids can effectively be separated from a petroleum distillate containing such a mixture by adjusting the molecular weight distribution of the petroleum acids in the mixture so that at least 10% of the acids have a molecular weight of less than 260 and at least 50% of the acids have a molecular weight of more than 260, treating the petroleum distillate with an aqueous solution of sodium hydroxide which solution is added with at least 5% of a sodium salt, calculated on the weight of the aqueous solution, at a temperature of at least 85.degree. C in one or more reactors to the formation of a reaction mixture containing three phases and causing said three phases to separate.
    Type: Grant
    Filed: March 19, 1975
    Date of Patent: September 20, 1977
    Assignee: AB Nynas-Petroleum
    Inventor: Carl Arne Bergholm
  • Patent number: 3992156
    Abstract: Improved apparatus for effecting contact between first and second immiscible fluids in order to provide mass transfer therebetween including a conduit having a fiber bundle or a plurality of fiber sub-bundles secured or mounted therein, the fiber bundle or sub-bundles having a plurality of elongated support members positioned within the bundles for alleviating stress from the fibers within the bundle or sub-bundles.
    Type: Grant
    Filed: July 23, 1975
    Date of Patent: November 16, 1976
    Assignee: Merichem Company
    Inventor: Kenyon E. Clonts
  • Patent number: 3979287
    Abstract: A process for recovering a dissolved component in high concentration from liquid streams containing said component in low concentration comprising adsorbing said component on a bed of adsorbent, passing a solution containing a high concentration of said component through said bed to increase the amount of component absorbed on said bed and passing an eluant through the bed to regenerate the adsorbent and produce an eluate having a high concentration of said component.
    Type: Grant
    Filed: July 9, 1975
    Date of Patent: September 7, 1976
    Assignee: Rohm and Haas Company
    Inventors: Pierre Roland Edouard Vulliez-Sermet, Elio Fiorentino
  • Patent number: 3966828
    Abstract: A process for converting mixtures of C.sub.6 to C.sub.30 n-paraffin and n-paraffin by-products to substantially pure n-paraffin which comprises catalytically hydrogenating the mixture at a temperature of from about 600.degree. to 750.degree.F. in the presence of a Group VIII metal on alumina catalyst, and from about 10 to 5,000 parts per million of nitrogen present as ammonia or an organonitrogen compound. The catalyst can additionally contain a Group VIB or VIIB metal.
    Type: Grant
    Filed: December 13, 1974
    Date of Patent: June 29, 1976
    Assignee: Texaco Inc.
    Inventors: Robert M. Suggitt, Walter C. Gates, Jr., Ralph B. Hudson, Jr.
  • Patent number: 3949012
    Abstract: A process for converting mixtures of C.sub.6 to C.sub.30 n-paraffin and n-paraffin by-products to substantially pure n-paraffin which comprises catalytically hydrogenating the mixture at a temperature of from about 600.degree. to 750.degree.F. in the presence of a Group VIII metal on alumina catalyst, and from about 10 to 5,000 parts per million of nitrogen present as ammonia or an organonitrogen compound. The catalyst can additionally contain a Group VIB or VIIB metal.
    Type: Grant
    Filed: December 26, 1973
    Date of Patent: April 6, 1976
    Assignee: Texaco Inc.
    Inventors: Robert M. Suggitt, Walter C. Gates, Jr., Ralph B. Hudson, Jr.