Oxidation Of Organic Sulfur Compounds To Sulfonic Acids Patents (Class 562/118)
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Patent number: 12157719Abstract: Haloalkane sulfonic acids and salts thereof are provided. In embodiments, a haloalkane sulfonic acid or salt thereof comprises an alkyl group, at least one sulfonic acid group, and one or more halogens selected from Cl, Br, I, and F, the haloalkane sulfonic acid having a total number of carbon atoms of from 2 to 9, and wherein if at least one F atom is present, the haloalkane sulfonic acid comprises at least one other halogen selected from Cl, Br, and I. Methods of making and using the haloalkane sulfonic acids/salts are also provided.Type: GrantFiled: August 20, 2021Date of Patent: December 3, 2024Assignee: University of KansasInventors: Mark Brandon Shiflett, Rajkumar Kore, Aaron M. Scurto
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Patent number: 11111212Abstract: Oxidized disulfide oil (ODSO) solvent compositions are derived from by-product disulfide oil (DSO) compounds produced as by-products from the generalized mercaptan oxidation (MEROX) processing of a refinery feedstock. The oxidized disulfide oil (ODSO) solvent compositions comprise at least a primary oxidized disulfide oil (ODSO) compound selected from either water soluble or water insoluble oxidized disulfide oil (ODSO) compounds and in some embodiments at least 0.1 ppmw of a secondary oxidized disulfide oil (ODSO) compound that is a water soluble oxidized disulfide oil (ODSO) compound.Type: GrantFiled: August 17, 2020Date of Patent: September 7, 2021Assignee: Saudi Arabian Oil CompanyInventors: Omer Refa Koseoglu, Robert Peter Hodgkins, Adnan Al-Hajji, Hendrik Muller, Nadrah Al-Awani, Frederick Marie Adam, Qasim Saleem
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Patent number: 10927318Abstract: Oxidized disulfide oil (ODSO) compounds, derived from by-product disulfide oil (DSO) compounds from the MEROX process, are effective as lubricity additives for transportation fuels. Significant increases in lubricity of ultra-low sulfur fuels as measured by the WSD test were observed with addition of ODSO compounds in the range of from 0.1 ppmw to 10 ppmw. This use of ODSO compounds as lubricity additives converts an otherwise DSO waste oil product into a valuable commodity that has utility in improving lubricity properties of transportation fuels.Type: GrantFiled: December 5, 2018Date of Patent: February 23, 2021Assignee: Saudi Arabian Oil CompanyInventors: Omer Refa Koseoglu, Robert Peter Hodgkins
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Patent number: 10781168Abstract: Oxidized disulfide oil (ODSO) solvent compositions are derived from by-product disulfide oil (DSO) compounds produced as by-products from the generalized mercaptan oxidation (MEROX) processing of a refinery feedstock. The oxidized disulfide oil (ODSO) solvent compositions comprise at least a primary oxidized disulfide oil (ODSO) compound selected from either water soluble or water insoluble oxidized disulfide oil (ODSO) compounds and in some embodiments at least 0.1 ppmw of a secondary oxidized disulfide oil (ODSO) compound that is a water soluble oxidized disulfide oil (ODSO) compound.Type: GrantFiled: December 5, 2018Date of Patent: September 22, 2020Assignee: SAUDI ARABIAN OIL COMPANYInventors: Omer Refa Koseoglu, Robert Peter Hodgkins, Adnan Al-Hajji, Hendrik Muller, Nadrah Al-Awani, Frederick Marie Adam, Qasim Saleem
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Patent number: 10703715Abstract: The present invention relates to a process for the preparation of an alkanesulfonic acid by oxidation of a sulfur containing starting compound with an oxygen containing fluid, wherein the sulfur containing starting compound is provided in a reaction system, comprising a reaction vessel (1) with an expansion vessel (2) on its top, wherein the reaction vessel and the expansion vessel are connected to allow a flow of a fluid stream from the reaction vessel into the expansion vessel.Type: GrantFiled: September 5, 2018Date of Patent: July 7, 2020Assignee: Evonik Operations GmbHInventors: Benjamin Fonfe, Chiu Kee Cheung, Ali Hartwig
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Patent number: 10023531Abstract: The present invention relates to a process for preparing alkanesulfonic acids from dialkyl disulfides with nitric acid and oxygen.Type: GrantFiled: December 10, 2014Date of Patent: July 17, 2018Assignee: EVONIK DEGUSSA GmbHInventors: Benjamin Fonfe, Harald Jakob, Chuanhua He, Andreas Doerflein, Sebastian Fuss
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Patent number: 8987507Abstract: Disclosed is a method for producing a fluoroalkanesulfonic acid including (1) the step of reacting concentrated sulfuric acid and/or fuming sulfuric acid with a fluoroalkanesulfonate to cause an acid decomposition, thereby obtaining a reaction mixture containing the fluoroalkanesulfonic acid and a sulfur component; and (2) the step of adding an oxidizing agent to the reaction mixture obtained by the above step and then conducting a distillation, thereby obtaining the fluoroalkanesulfonic acid from the reaction mixture. It is possible by this method to efficiently reduce the sulfur component, thereby industrially advantageously obtaining fluoroalkanesulfonic acid of high purity.Type: GrantFiled: August 2, 2012Date of Patent: March 24, 2015Assignee: Central Glass Company, LimitedInventors: Tatsuya Irie, Kenji Isoyama, Tatsuo Miyazaki, Takashi Kashiwaba, Tsutomu Nanmyo
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Publication number: 20110263894Abstract: A process for compressing a hydrogen-sulfide-comprising gas stream, which comprises (i) compressing the hydrogen-sulfide-comprising gas stream in a compressor, (ii) flushing the compressor with a mixture comprising dialkyl polysulfides, dialkyl disulfides and at least one amine; a process for producing sulfur compounds, selected from the group consisting of alkylmercaptans, dialkyl disulfides and alkanesulfonic acids, which comprises the conversion of hydrogen-sulfide-comprising gas streams, wherein the hydrogen-sulfide-comprising gas streams are compressed according to the process comprising steps i) and ii); and also the use of a mixture comprising dialkyl polysulfides, dialkyl disulfides and at least one amine for removing sulfur deposits which occur in the compression of hydrogen-sulfide-comprising gas streams.Type: ApplicationFiled: December 22, 2009Publication date: October 27, 2011Applicant: BASF SEInventors: Andreas Woelfert, Frank Grzonkowski, Harald Jachow, Guenter Renz
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Patent number: 8008425Abstract: A thiophene compound having sulfonyl groups which is represented by the formula [1]. It has high heat resistance and high unsusceptibility to oxidation and can improve solubility and dispersibility in various solvents. [In the formula, R1 and R2 each independently represents hydrogen, halogeno, cyano, etc.; and R3 and R3? each independently represents C1-20 alkyl, C1-20 haloalkyl, phenyl optionally substituted by W, thienyl optionally substituted by W, etc. (W represents chlorine, etc.).Type: GrantFiled: July 11, 2006Date of Patent: August 30, 2011Assignee: Nissan Chemical Industries, Ltd.Inventors: Nobuyuki Kakiuchi, Hitoshi Furusho, Naoki Otani, Tatsuo Okauchi, Naoki Nakaie
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Publication number: 20110172138Abstract: One subject of the invention is a dimethyl disulphide in which the content of biocarbon is at least 1%. Another subject of the invention is processes for preparing this dimethyl disulphide. Yet another subject of the invention is the use of such a dimethyl disulphide for the manufacture of methanesulphonic acid.Type: ApplicationFiled: August 18, 2009Publication date: July 14, 2011Applicant: ARKEMA FRANCEInventors: Christian Forquy, Georges Fremy
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Publication number: 20090127491Abstract: A thiophene compound having sulfonyl groups which is represented by the formula [1]. It has high heat resistance and high unsusceptibility to oxidation and can improve solubility and dispersibility in various solvents. [In the formula, R1 and R2 each independently represents hydrogen, halogeno, cyano, etc.; and R3 and R3? each independently represents C1-20 alkyl, C1-20 haloalkyl, phenyl optionally substituted by W, thienyl optionally substituted by W, etc. (W represents chlorine, etc.).Type: ApplicationFiled: July 11, 2006Publication date: May 21, 2009Applicant: Nissan Chemical Industries, Ltd.Inventors: Nobuyuki Kakiuchi, Hitoshi Furusho, Naoki Otani, Tatsuo Okauchi, Naoki Nakaie
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Patent number: 6927305Abstract: The present invention relates to a process for the production of alkanesulfonic acid. More particularly, the present invention relates to a process for the production of alkanesulfonic acid from alkyl mercaptan effluents generated in chemical industries. The process of the invention comprises the oxidation of the entire alkyl mercaptan generated as an effluent in the chemical industries to serve two concomitant purposes: (1) complete removal of obnoxious odor, and (2) value addition by the production of alkanesulfonic acids selectively in quantitative yields.Type: GrantFiled: March 20, 2003Date of Patent: August 9, 2005Assignee: Council of Scientific and Industrial ResearchInventors: Boyapati Manoranjan Choudary, Kottapalli Koteswara Rao, Mahendar Koosam
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Patent number: 6843978Abstract: The present invention refers to a microporous material formed by oxygen, silicon, germanium, aluminum, boron, gallium, zirconium and/or titanium in its composition, called TIQ-6, to its catalytic applications in oxidation reactions, and to a method of the TIQ-6 material's preparation based on the synthesis of a gel with a titanium and/or zirconium content, its hydrothermal treatment under controlled conditions, and the treatment of the resulting laminar material with a solution of an organic compound containing a proton accepting group. This swollen material is subjected to a specific treatment to obtain a high external area delaminated solid. A material, METIQ-6, similar to the TIQ-6 material, but also having organic groups anchored on its surface incorporated by a post-synthesis process onto the TIQ-6 material is also claimed.Type: GrantFiled: May 24, 2002Date of Patent: January 18, 2005Assignees: Consejo Superior De Investigaciones Cientificas, Universidad Politecnica De ValenciaInventors: Avelino Corma Canós, Vicente Fornes Segui, Urbano Díaz Morales, Marcelo Eduardo Domine
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Patent number: 6531629Abstract: The invention relates to a process for the prepartaion of alkanesulfonic acids, comprising the following steps: (a) oxidation of alkylmercaptans and/or dialkyl disulfides and/or dialkyl polysulfides having from three to nine sulfur atoms with nitric acid to form alkanesulfonic acids, water, nitrogen oxides and other byproducts, (b) regeneration of the nitrogen oxides obtained from step (a) with oxygen to give nitric acid and recycling of the nitric acid to step (a), where steps (a) and (b) are carried out in reaction chambers separate from one another.Type: GrantFiled: May 15, 2001Date of Patent: March 11, 2003Assignee: BASF AktiengesellschaftInventors: Matthias Eiermann, Christian Tragut, Klaus Ebel
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Patent number: 6495714Abstract: A process for preparing alkanesulfonic acids from dialkyl sulfites comprises the following steps: rearrangement of dialkyl sulfite in the presence of a suitable catalyst to form the corresponding alkyl alkanesulfonate and hydrolysis of the resulting alkyl alkanesulfonate to give the corresponding alkanesulfonic acid.Type: GrantFiled: August 3, 2001Date of Patent: December 17, 2002Assignee: BASF AktiengesellschaftInventors: Klaus Halbritter, Hans-Josef Sterzel, Matthias Eiermann, Eva Freudenthaler
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Patent number: 6187169Abstract: A procedure for the generation of organosulfonic acids from solutions of corresponding metal organosulfonate compounds by electrowinning, electrolytically driven hydrolysis or chemically driven hydrolysis is described. Appropriate organosulfonate compounds include the water soluble salts of alkanesulfonic and aromatic sulfonic acids which incorporate metals from Group VIB, VIIB, VIIIB, IB, IIB or VA of the periodic table. The electrowinning and electrolytic techniques described can be applied in divided or undivided cells and can be operated in continuous fashion to provide the greatest efficiency. Hydrolysis based methods can employ either anodic oxidation or oxidation both of which function to oxidize the metal cation(s) present to hydrolytically unstable higher oxidation states.Type: GrantFiled: April 8, 1999Date of Patent: February 13, 2001Assignee: ATOFINA Chemicals, Inc.Inventors: Michael D. Gernon, Nicholas M. Martyak, Martin Nosowitz, Gary S. Smith
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Patent number: 6124497Abstract: A process for preparing alkane sulfonic acids and sulfonyl chlorides by oxidation of alkanethiols or dialkyl disulfides in the presence of nitric acid or nitric oxides as a catalyst and in the presence of bromide as a cocatalyst.Type: GrantFiled: October 22, 1999Date of Patent: September 26, 2000Assignee: Innochem Inc.Inventor: Johnson Chen
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Patent number: 6066760Abstract: A process is disclosed for the efficient production of high purity alkane sulfonic acid and/or alkane sulfonyl chloride product wherein a compound of the formula RSX, where X is hydrogen or --SR.sup.1 and R and R.sup.1 are alkyl radicals is continuously reacted with chlorine in aqueous hydrochloric acid to produce a turbulent evolution of hydrochloride gas, passing the reactants through stationary mixing elements to promote plug-flow, and separately withdrawing a product. Apparatus for this process is also disclosed.Type: GrantFiled: March 31, 1994Date of Patent: May 23, 2000Assignee: Elf Atochem North America, Inc.Inventor: Steven Gabriel Schon
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Patent number: 6060621Abstract: 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: GrantFiled: October 1, 1998Date of Patent: May 9, 2000Assignee: Grillo-Werke A.G.Inventors: Ingo Biertuempel, Klaus Driemel, Joachim Van De Flierdt, Dieter M.M. Rohe
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Patent number: 5912385Abstract: This invention relates to a process for the production of an alkanesulfionic acid such as isethionic acid with a high purity in a high yield and at a low cost by oxidation of a (hydroxy)alkylmercaptan with hydrogen peroxide characterized in that a whole amount beyond a stoichiometric amount of a solution of hydrogen peroxide having a H.sub.2 O.sub.2 concentration of not less than 50% by weight is charged into a reaction vessel, said mercaptan is continuously fed at a temperature of 50.degree. C. or lower, aging is carried out, distillation with boiling is carried out and then the reaction mixture is contacted with an anion exchanger.Type: GrantFiled: January 20, 1998Date of Patent: June 15, 1999Assignee: Tokai Denka Kogyo Kabushiki KaishaInventors: Kazuyoshi Kushibe, Hiromitsu Kobayashi, Hirohisa Nitoh, Hirotsugu Kitamura
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Patent number: 5840972Abstract: A process is disclosed for the preparation of N.sup.G -monoalkyl-L-arginine and related compounds and salts thereof, for example N.sup.G -monomethyl-L-arginine by reacting N-alkylaminoiminomethane sulphonic acid of formula (II) with an amino acid of formula (III).Type: GrantFiled: February 22, 1995Date of Patent: November 24, 1998Assignee: Glaxo Wellcome Inc.Inventors: Rajnikant Patel, Amrik Singh Mahal, Donald Lloyd Winston Burford
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Patent number: 5583253Abstract: A process of preparing purified alkanesulfonic acid from crude aqueous alkanesulfonic acid containing oxidizable impurities wherein the crude material is treated with a sufficient amount of chlorine to convert the oxidizable impurities to alkanesulfonyl chloride and then hydrolyzing said alkanesulfonyl chloride to alkanesulfonic acid by heating.Type: GrantFiled: March 27, 1991Date of Patent: December 10, 1996Inventors: Phyllis A. Henderson, Steven G. Schon, Carl Postuma
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Patent number: 4987250Abstract: Hydroxy sulfonic acids in general and isethionic acid (2-hydroxy ethyl sulfonic acid) in particular can be prepared at 99+% purity and good yields by the selective oxidation of a precursor hydroxy mercaptan with hydrogen peroxide. The resulting product is pure enough to be used directly in the synthesis of sulfo-acrylic esters which are finding considerable use as stabilizers in producing vinylidene chloride copolymers used for FDA approved packaging films.Type: GrantFiled: January 19, 1989Date of Patent: January 22, 1991Assignee: Union Oil Company of CaliforniaInventors: Dennis E. McGee, Ted S. Hallen
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Patent number: 4956494Abstract: Alkanesulfonic acids and alkanesulfonyl chlorides, free of undesirable side products arising from side-chain chlorination, are prepared by oxidation with hydrogen peroxide of the corresponding alkanethiol, dialkyldisulfide or alkyl alkanethiolsulfonate mixed with aqueous hydrochloric acid.Type: GrantFiled: June 15, 1989Date of Patent: September 11, 1990Assignee: Pennwalt CorporationInventors: Altaf Husain, Gregory A. Wheaton
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Patent number: 4895977Abstract: The removal of oxidizable organic impurities which include alkylthiolsulfonate from alkanesulfonic acids by treatment with an ozone containing gas is disclosed. The treated products have improved color and odor and exhibit improved long-term color stability.Type: GrantFiled: December 12, 1988Date of Patent: January 23, 1990Assignee: Pennwalt CorporationInventor: Martin Nosowitz