Utilizing Sulfur Trioxide, Oleum, Sulfuric Acid Or Halosulfonic Acid Patents (Class 562/123)
  • Patent number: 10184076
    Abstract: The present invention provides an internal olefin sulfonate composition, comprising water and an internal olefin sulfonate mixture having an average carbon number of at least 20, wherein the internal olefin sulfonate mixture comprises hydroxy sulfonates and alkene sulfonates in a weight ratio of hydroxy sulfonates to alkene sulfonates of at least 3.25. The invention further provides a method of treating a crude oil containing formation.
    Type: Grant
    Filed: March 4, 2014
    Date of Patent: January 22, 2019
    Assignee: SHELL OIL COMPANY
    Inventors: Julian Richard Barnes, James Laurel Buechele, Hendrik Dirkzwager, Willem Johan Louis Genuit, Jeremiah Michael Purcell, Catherine Semien, Carmen Geraldine Reznik
  • Patent number: 9732267
    Abstract: A hydrocarbon recovery composition which comprises a first blend of C24-28 internal olefin sulfonates and an injectable fluid composition comprising the hydrocarbon recovery composition, water and/or brine wherein the hydrocarbon recovery composition is present in an amount of from 0.05 to 1.0 wt % of the total injectable fluid composition can be used for enhanced hydrocarbon recovery from a formation.
    Type: Grant
    Filed: October 13, 2015
    Date of Patent: August 15, 2017
    Assignee: SHELL OIL COMPANY
    Inventors: Julian Richard Barnes, Marten Adriaan Buijse, Marinus Cornelis Hendrikus Grutters, Robert Moene, Reinaldo Conrado Navarrete, Thomas Carl Semple, Andrew Granja Shepherd
  • Patent number: 8993798
    Abstract: The present invention is directed to an isomerized alpha olefin sulfonate and a method of making the same wherein the isomerized alpha olefin sulfonate is derived from sulfonating an isomerized alpha olefin with sulfur trioxide in the presence of air thereby producing an isomerized alpha olefin sulfonic acid, wherein the isomerized alpha olefin is derived from the isomerization of C12-C20 normal alpha olefins; and neutralizing the isomerized alpha olefin sulfonic acid with a source of an alkali metal or ammonium or substituted ammonium ion.
    Type: Grant
    Filed: December 8, 2010
    Date of Patent: March 31, 2015
    Assignee: Chevron Oronite Company LLC
    Inventors: Curtis Bay Campbell, Andrew J. Howes
  • Patent number: 8741807
    Abstract: A compound useful as a plant activator for activating an endogenous defense system of a plant to control disease damage is provided. A compound represented by the formula: (R3)NH—(CH2)4—N(R1)—(CH2)3—NH(R2) (one of R1 and R2 represents a linear C6-18 alkanoyl group or alkenoyl group, the other represents hydrogen atom or a protective group of amino group; and R3 represents hydrogen atom or a protective group of amino group).
    Type: Grant
    Filed: February 23, 2012
    Date of Patent: June 3, 2014
    Assignees: The University of Tokyo, National Institute of Agrobiological Sciences, Riken
    Inventors: Tadao Asami, Masashi Hikosaka, Masaki Mori, Satoru Maeda, Fumio Matsuda, Kazuki Saito
  • Patent number: 8722745
    Abstract: The invention relates to a sulfur-containing compound and the preparation thereof. The invention also relates to the uses of the sulfur-containing compound in inhibiting inducible nitric oxide synthase and/or cyclooxygenase-2 and in treating the diseases associated with inducible nitric oxide synthase and/or cyclooxygenase-2. This invention also describes a series of chemical analogues of the said sulfur-containing compound and the preparation of these compounds.
    Type: Grant
    Filed: February 6, 2013
    Date of Patent: May 13, 2014
    Assignee: National Sun Yat-Sen University
    Inventors: Jyh-Horng Sheu, Chih-Hua Chao, Zhi-Hong Wen
  • Patent number: 8399661
    Abstract: The invention relates to a sulfur-containing compound and the preparation thereof. The invention also relates to the uses of the sulfur-containing compound in inhibiting inducible nitric oxide synthase and/or cyclooxygenase-2 and in treating the diseases associated with inducible nitric oxide synthase and/or cyclooxygenase-2. This invention also describes a series of chemical analogues of the said sulfur-containing compound and the preparation of these compounds.
    Type: Grant
    Filed: July 14, 2008
    Date of Patent: March 19, 2013
    Assignee: National Sun Yat-Sen University
    Inventors: Jyh-Horng Sheu, Chih-Hua Chao, Zhi-Hong Wen
  • Patent number: 8299289
    Abstract: The present invention is directed to an isomerized alpha olefin sulfonate and a method of making the same wherein the isomerized alpha olefin sulfonate is derived from sulfonating an isomerized alpha olefin with sulfur trioxide in the presence of air thereby producing an isomerized alpha olefin sulfonic acid, wherein the isomerized alpha olefin is derived from the isomerization of C12-C40 normal alpha olefins; and neutralizing the isomerized alpha olefin sulfonic acid with a source of a mono-valent cation.
    Type: Grant
    Filed: July 29, 2011
    Date of Patent: October 30, 2012
    Assignee: Chevron Oronite Company LLC
    Inventors: Curtis Bay Campbell, Theresa Ann Denslow
  • Patent number: 8283492
    Abstract: A process for manufacture of hydrofluoroalkanesulfonic acid with at least one hydrogen bonded to the carbon atom adjacent to the carbon atom bonded to the sulfonic acid group comprising: contacting a fluoroolefin with sulfite in an aqueous solution adjusted to about pH 4 to pH 12; removing water from the solution to form a solid; directly treating the solid with oleum; and distilling the hydrofluoroalkanesulfonic acid therefrom. Also a process for manufacture of potassium hydrofluoroalkanesulfonate in high purity is described.
    Type: Grant
    Filed: January 20, 2011
    Date of Patent: October 9, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Christopher P. Junk, Zoe Schnepp
  • Patent number: 8283491
    Abstract: The present invention is directed to an isomerized alpha olefin sulfonate and a method of making the same wherein the isomerized alpha olefin sulfonate is derived from sulfonating an isomerized alpha olefin with sulfur trioxide in the presence of air thereby producing an isomerized alpha olefin sulfonic acid, wherein the isomerized alpha olefin is derived from the isomerization of C12-C40 normal alpha olefins; and neutralizing the isomerized alpha olefin sulfonic acid with a source of a mono-valent cation.
    Type: Grant
    Filed: October 23, 2008
    Date of Patent: October 9, 2012
    Assignee: Chevron Oronite Company LLC
    Inventors: Curtis Bay Campbell, Theresa Ann Denslow
  • Patent number: 8263803
    Abstract: Metallic dihydroxybenzenedisulfonates are prepared, preferably from alkaline metals, from corresponding dihydroxybenzenedisulfonic acids, by reacting the dihydroxybenzenedisulfonic acid present in a sulfuric medium with an adequate amount of a salt including a sulfate or hydrogenosulfate anion.
    Type: Grant
    Filed: June 12, 2007
    Date of Patent: September 11, 2012
    Assignee: Rhodia Operations
    Inventors: Michel Dury, Hervé Bres
  • Patent number: 8242300
    Abstract: The present invention relates to selective partial oxidation of methane in the absence of a solvent such as sulfuric acid or oleum.
    Type: Grant
    Filed: July 1, 2008
    Date of Patent: August 14, 2012
    Assignee: Dow Global Technologies LLC
    Inventors: Michael A. Gonzalez, Daniel R. Henton, David C. Molzahn
  • Publication number: 20110282097
    Abstract: The present invention is directed to an isomerized alpha olefin sulfonate and a method of making the same wherein the isomerized alpha olefin sulfonate is derived from sulfonating an isomerized alpha olefin with sulfur trioxide in the presence of air thereby producing an isomerized alpha olefin sulfonic acid, wherein the isomerized alpha olefin is derived from the isomerization of C12-C40 normal alpha olefins; and neutralizing the isomerized alpha olefin sulfonic acid with a source of a mono-valent cation.
    Type: Application
    Filed: July 29, 2011
    Publication date: November 17, 2011
    Applicant: Chevron Oronite Company LLC
    Inventors: Curtis Bay Campbell, Theresa Ann Denslow
  • Publication number: 20110269989
    Abstract: A method for halogenating, sulfonating, or sulfo-halogenating a feed comprising paraffin, by subjecting a mixture comprising the feed and a reagent selected from the group consisting of sulfonating agents, halogenating agents, and combinations thereof to a shear rate of at least 20,000 s?1 to produce a high-shear treated product; cooling the high shear-treated product by heat exchange with a heat transfer medium, to produce a cooled product; and separating the high shear-treated product into an offgas and a liquid product comprising at least one selected from the group consisting of sulfonated paraffins, halogenated paraffins, and sulfo-halogenated paraffins. A high shear system for the production of halogenated, sulfonated, or sulfo-halogenated paraffin is also provided.
    Type: Application
    Filed: March 2, 2011
    Publication date: November 3, 2011
    Applicant: H R D Corporation
    Inventors: Abbas HASSAN, Krishnan Viswanathan, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
  • Publication number: 20110152571
    Abstract: The present invention is directed to an isomerized alpha olefin sulfonate and a method of making the same wherein the isomerized alpha olefin sulfonate is derived from sulfonating an isomerized alpha olefin with sulfur trioxide in the presence of air thereby producing an isomerized alpha olefin sulfonic acid, wherein the isomerized alpha olefin is derived from the isomerization of C12-C20 normal alpha olefins; and neutralizing the isomerized alpha olefin sulfonic acid with a source of an alkali metal or ammonium or substituted ammonium ion.
    Type: Application
    Filed: December 8, 2010
    Publication date: June 23, 2011
    Inventors: Curtis Bay Campbell, Andrew J. Howes
  • Patent number: 7897807
    Abstract: A process for manufacture of hydrofluoroalkanesulfonic acid with at least one hydrogen bonded to the carbon atom adjacent to the carbon atom bonded to the sulfonic acid group comprising: contacting a fluoroolefin with sulfite in an aqueous solution adjusted to about pH 4 to pH 12; removing water from the solution to form a solid; directly treating the solid with oleum; and distilling the hydrofluoroalkanesulfonic acid therefrom. Also a process for manufacture of potassium hydrofluoroalkanesulfonate in high purity is described.
    Type: Grant
    Filed: February 22, 2010
    Date of Patent: March 1, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Christopher P. Junk, Zoe Schnepp
  • Patent number: 7683209
    Abstract: A process for manufacture of hydrofluoroalkanesulfonic acid with at least one hydrogen bonded to the carbon atom adjacent to the carbon atom bonded to the sulfonic acid group comprising: contacting a fluoroolefin with sulfite in an aqueous solution adjusted to about pH 4 to pH 12; removing water from the solution to form a solid; directly treating the solid with oleum; and distilling the hydrofluoroalkanesulfonic acid therefrom. Also a process for manufacture of potassium hydrofluoroalkanesulfonate in high purity is described.
    Type: Grant
    Filed: June 6, 2006
    Date of Patent: March 23, 2010
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Christopher P. Junk, Zoe Schnepp
  • Patent number: 7579499
    Abstract: Hexafluoroisobutylene and its higher homologs are easily reacted with SO3 to give fluorosulfates of the formula CH2?C(R)CF2OSO2F, wherein R is a linear branched or cyclic fluoroalkyl group comprised of 1 to 10 carbon atoms and may contain ether oxygen. These compounds react under mild conditions with many nucleophiles to give CH2?C(R)CF2X, where X is derived from the nucleophile. This reaction provides a route to many substituted hexafluoroisobutylenes, which copolymerize easily with other fluoro- and hydrocarbon monomers such as vinylidene fluoride and ethylene.
    Type: Grant
    Filed: March 22, 2007
    Date of Patent: August 25, 2009
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Victor Filippovich Cherstkov, Nina Ivanova Delyagina, Viacheslav A. Petrov, Paul R. Resnick
  • Publication number: 20080139840
    Abstract: A process for preparing an alkyl aryl sulphonic acid comprising the steps of: (a) contacting an alkyl aromatic hydrocarbon with a gaseous sulphonating agent to produce (i) a first liquid reaction product comprising an alkyl aryl sulphonic acid and (ii) a gaseous effluent stream; (b) separating the first liquid reaction product from the gaseous effluent stream; (c) purifying the gaseous effluent stream to provide a cleaned gaseous stream and a second liquid reaction product; (d) recycling the second liquid reaction product to the first liquid reaction product produced after separation step (b) to produce a third liquid reaction product comprising alkyl aryl sulphonic acid; wherein the alkyl aromatic hydrocarbon is obtained by contacting an aromatic hydrocarbon with an olefin under alkylating conditions, and wherein said olefin is obtained by dehydrogenation of a Fischer-Tropsch derived paraffinic feedstock.
    Type: Application
    Filed: November 1, 2007
    Publication date: June 12, 2008
    Inventors: Matthew Thomas Anderson, Stacy John Archibald, Hendrik Dirkzwager, Wayne Ashley Thomas
  • Patent number: 7282603
    Abstract: Anhydrous processing to convert methane into oxygenates (such as methanol), liquid fuels, or olefins uses an initiator to create methyl radicals. These radicals combine with sulfur trioxide to form methyl-sulfonate radicals. These radicals attack fresh methane, forming stable methane-sulfonic acid (MSA) while creating new methyl radicals to sustain a chain reaction. This system avoids the use or creation of water, and liquid MSA is an amphoteric solvent that increasing the solubility and reactivity of methane and SO3. MSA from this process can be sold or used as a valuable chemical with no mercaptan or halogen impurities, or it can be heated and cracked to release methanol (a clean fuel, gasoline additive, and chemical feedstock) and sulfur dioxide (which can be oxidized to SO3 and recycled back into the reactor). MSA also can be converted into gasoline, olefins, or other valuable chemicals.
    Type: Grant
    Filed: June 21, 2004
    Date of Patent: October 16, 2007
    Inventor: Alan K. Richards
  • Patent number: 7119226
    Abstract: A process for the facile two-step synthesis of methanol from methane is disclosed. In accordance with the invention, an appropriate combination of initiator and reaction medium is employed to achieve methane conversion in very high selectivity and yield under near-ambient temperature.
    Type: Grant
    Filed: April 13, 2005
    Date of Patent: October 10, 2006
    Assignee: The Penn State Research Foundation
    Inventors: Ayusman Sen, Minren Lin
  • Patent number: 6864388
    Abstract: A process for preparing salts of methallylsulfonic acid in which the reaction mixture produced from the sulfonation is diluted with water and neutralized with a base.
    Type: Grant
    Filed: July 24, 2002
    Date of Patent: March 8, 2005
    Assignee: OXENO Olefinchemie GmbH
    Inventors: Claus York Werninger, Lothar Kerker, Hartmut Steinbeisser, Wilfried Bueschken, Franz-Felix Kuppinger, Peter Ernst Esser
  • Patent number: 6660882
    Abstract: The present invention provides a process for the preparation of highly pure 2-Methyl-2-propene-1-sulfonic acid, sodium salt in high yield, with very low iron content, by the reaction of distilled sulfur trioxide complexed with a Lewis base in a halogentated solvent, the unreacted sulfur trioxide vapors being removed from the reactor before the mixture is treated with liquefied isobutylene, and neutralization by a base with an iron content within the range of 0 to 20 ppm.
    Type: Grant
    Filed: March 18, 2002
    Date of Patent: December 9, 2003
    Assignee: Council of Scientific and Industrial Research
    Inventors: Prashant Purushottam Barve, Sunil Shankar Joshi, Ravindra William Shinde, Shrikant Madhukar Ghike, Milind Yashwant Gupte, Chandrashekhar Narayan Joshi, Raghavendra Venkatrao Naik
  • Patent number: 6060621
    Abstract: The process for the preparation of methanesulfonic acid by reacting sulfite ions within an aqueous system with dimethyl sulfate at an elevated temperature and adding a strong acid subsequently, wherein the molar ratio of sulfite ions to dimethyl sulfate is 1.5 to 2.5:1, preferably 2:1, and the reaction charge is maintained at said elevated temperature for at least 2 h, preferably 4 h.
    Type: Grant
    Filed: October 1, 1998
    Date of Patent: May 9, 2000
    Assignee: Grillo-Werke A.G.
    Inventors: Ingo Biertuempel, Klaus Driemel, Joachim Van De Flierdt, Dieter M.M. Rohe
  • Patent number: 5936106
    Abstract: An process for forming a product which may be in a liquid phase is disclosed wherein a first reactant, preferably a liquid reactant, is directly fed into a reaction zone containing mixing elements and which comprises a first compartment of a reactor. A second reactant, which is maintained at a higher pressure, is fed into a second compartment of the reactor separated from the first compartment by a porous wall. The second reactant passes through this porous wall into the reaction zone to react with the first reactant. The process thereby controls rates of the reactions and the exothermic heats generated by the reactions. Pulsatile flow in one or both reaction compartments improves mixing. An evaporator for a portion of the product improves product quality and permits higher reaction temperatures in the reactor.
    Type: Grant
    Filed: December 6, 1996
    Date of Patent: August 10, 1999
    Assignee: SRI International
    Inventors: William J. Asher, Daryl L. Roberts, Jerry L. Jones, Douglas E. Gottschlich
  • Patent number: 5922903
    Abstract: An arrangement for a falling film type reactor uses corrugated plates to improve the distribution and dispersion of the gaseous reactant into the liquid. Corrugated plates introduce increased turbulence for promoting better distribution and dispersion of the gas. Corrugation angles can be varied to suit the fluid flow properties of the liquid reactant. The reactor arrangement can also include heat transfer channels defined by the corrugated plates in an alternate arrangement of heat transfer channels and gas liquid contacting channels. The corrugations may also be varied to suit the particular heat transfer requirements of the reactions. The corrugated plates are spaced apart in the contacting channels to prevent localized film contact and placed in contact in the heat exchange portion to stabilize the plate elements defining the corrugations.
    Type: Grant
    Filed: November 10, 1997
    Date of Patent: July 13, 1999
    Assignee: UOP LLC
    Inventor: Peter R. Pujado
  • Patent number: 5583240
    Abstract: An exothermic process for forming a product which may be in a liquid phase is disclosed wherein a first reactant, preferably a liquid reactant, is directly fed into a reaction zone containing mixing elements and which comprises a first compartment of a reactor. A second reactant, which is maintained at a higher pressure, is fed into a second compartment of the reactor separated from the first compartment by a porous wall. The second reactant passes through this porous wall into the reaction zone to react with the first reactant. The process thereby controls rates of the reactions and the exothermic heats generated by the reactions. Pulsatile flow in one or both reaction compartments improves mixing. An evaporator for a portion of the product improves product quality and permits higher reaction temperatures in the reactor.
    Type: Grant
    Filed: March 2, 1994
    Date of Patent: December 10, 1996
    Assignee: SRI International
    Inventors: William J. Asher, Daryl L. Roberts, Jerry L. Jones, Douglas E. Gottschlich
  • Patent number: 5488148
    Abstract: A process for sulfonating internal olefins wherein a dilute solution of the internal olefins in an inert hydrocarbon solvent is sulfonated to produce a reaction mixture containing intermediate sulfonated compounds, the intermediate sulfonated compounds in the reaction mixture being neutralized under conditions to form neutralized sulfonated compounds, the neutralized sulfonated compounds in the reaction mixture being hydrolyzed to form a product mixture containing hydroxy alkane sulfonates and alkene sulfonates that are then recovered.
    Type: Grant
    Filed: September 1, 1993
    Date of Patent: January 30, 1996
    Assignee: Vista Chemical Company
    Inventors: Upali Weerasooriya, John Lin, K. Lee Matheson, Donald T. Robertson, Janet L. Watson, LeAnn M. Rowe
  • Patent number: 5445801
    Abstract: Mulitube falling-film reactor for the continuous sulfonation and sulfation of fluid-state organic substances by reaction with gaseous sulphuric anhydride (SO.sub.3), has each tubular element non-permanently fixed to the plates and has a nozzle (10) fitted in a sleeve (20) integral with a reaction tube (23). The nozzle (10) can slide within the sleeve (20) and may be placed at different heights with respect to the latter, forming with the end-piece (14) a cylindrical crown opening (18) of fixed width and variable height. Such arrangement permits to control the delivery of the fluid to be sulfonated. The opposite end of each tube (23) fits into a double-plate seal system.
    Type: Grant
    Filed: May 18, 1993
    Date of Patent: August 29, 1995
    Assignee: Meccaniche Moderne S.r.l. Chemical Plants Division
    Inventor: Carlo Pisoni
  • Patent number: 5189205
    Abstract: A process for preparing isocyanates comprising (a) contacting carbon dioxide and a primary amine in the presence of an aprotic organic solvent and an organic, nitrogenous base to produce the corresponding ammonium carbamate salt, and (b) reacting the ammonium carbamate salt with an electrophilic or oxophilic dehydrating agent to produce the corresponding isocyanate. A second embodiment comprises recovering the ammonium carbamate salt of step (a) prior to reacting the ammonium carbamate salt with an electrophilic or oxophilic dehydrating agent in the presence of an aprotic organic solvent and an organic, nitrogenous base.
    Type: Grant
    Filed: March 16, 1992
    Date of Patent: February 23, 1993
    Assignee: Monsanto Compamy
    Inventors: William D. McGhee, Thomas E. Waldman
  • Patent number: 5117051
    Abstract: Alkanedisulfonic acids, particularly methanedisulfonic acid (methionic acid), can be prepared by reacting the corresponding alkanesulfonic acid with chlorosulfonic acid. The reaction is carried out by heating the reactants with agitation, preferably under substantially anhydrous conditions in the presence of oxygen and at substantially atmospheric pressure. Particularly good yields are obtained using an activated carbon co-catalyst.
    Type: Grant
    Filed: October 15, 1991
    Date of Patent: May 26, 1992
    Assignee: Atochem North America, Inc.
    Inventor: Stanley R. Sandler
  • Patent number: 4973686
    Abstract: The invention relates to the use of selected carboxylic acid esters which are liquid under reaction conditions and correspond to general formula (I)X--COOR.sup.1 (I)in which R.sup.1 is an alkyl radical unbranched in the .alpha.-position and X is hydrogen or a group corresponding to general formula (II) ##STR1## in which R.sup.2, R.sup.3 and R.sup.4 represent fluorine and/or chlorine and one of these substituents may also be hydrogen or one or two of these substituents may also be lower alkyl, as reaction medium for the sulfonation and/or sulfatization or organic components with SO.sub.3 to light-colored reaction products.
    Type: Grant
    Filed: September 2, 1988
    Date of Patent: November 27, 1990
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Josef Kretschmann, Franz-Josef Carduck, Willi Wuest, Hubert Harth, Dirk Springer
  • Patent number: 4925976
    Abstract: A method for sulfonating olefins comprising the steps of mixing (A) internal olefins having 8 to 22 carbon atoms with (B) alpha-olefins having an average carbon atom number, larger by 3 to 7 than that of the internal olefins (A) in a weight ratio of (A)/(B)=95/5 to 5/95, and sulfonating the resultant mixture with a sulfonating agent. Thus, internal olefins can be sulfonated at a high conversion.
    Type: Grant
    Filed: March 26, 1986
    Date of Patent: May 15, 1990
    Assignee: Lion Corporation
    Inventors: Toshimi Terao, Kentaro Kiyama, Kyozo Kitano