Oxidation Of Organic Sulfur Compounds To Sulfonic Acids Patents (Class 562/118)
  • Patent number: 12157719
    Abstract: 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: Grant
    Filed: August 20, 2021
    Date of Patent: December 3, 2024
    Assignee: University of Kansas
    Inventors: Mark Brandon Shiflett, Rajkumar Kore, Aaron M. Scurto
  • Patent number: 11111212
    Abstract: 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: Grant
    Filed: August 17, 2020
    Date of Patent: September 7, 2021
    Assignee: Saudi Arabian Oil Company
    Inventors: Omer Refa Koseoglu, Robert Peter Hodgkins, Adnan Al-Hajji, Hendrik Muller, Nadrah Al-Awani, Frederick Marie Adam, Qasim Saleem
  • Patent number: 10927318
    Abstract: 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: Grant
    Filed: December 5, 2018
    Date of Patent: February 23, 2021
    Assignee: Saudi Arabian Oil Company
    Inventors: Omer Refa Koseoglu, Robert Peter Hodgkins
  • Patent number: 10781168
    Abstract: 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: Grant
    Filed: December 5, 2018
    Date of Patent: September 22, 2020
    Assignee: SAUDI ARABIAN OIL COMPANY
    Inventors: Omer Refa Koseoglu, Robert Peter Hodgkins, Adnan Al-Hajji, Hendrik Muller, Nadrah Al-Awani, Frederick Marie Adam, Qasim Saleem
  • Patent number: 10703715
    Abstract: 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: Grant
    Filed: September 5, 2018
    Date of Patent: July 7, 2020
    Assignee: Evonik Operations GmbH
    Inventors: Benjamin Fonfe, Chiu Kee Cheung, Ali Hartwig
  • Patent number: 10023531
    Abstract: The present invention relates to a process for preparing alkanesulfonic acids from dialkyl disulfides with nitric acid and oxygen.
    Type: Grant
    Filed: December 10, 2014
    Date of Patent: July 17, 2018
    Assignee: EVONIK DEGUSSA GmbH
    Inventors: Benjamin Fonfe, Harald Jakob, Chuanhua He, Andreas Doerflein, Sebastian Fuss
  • Patent number: 8987507
    Abstract: 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: Grant
    Filed: August 2, 2012
    Date of Patent: March 24, 2015
    Assignee: Central Glass Company, Limited
    Inventors: Tatsuya Irie, Kenji Isoyama, Tatsuo Miyazaki, Takashi Kashiwaba, Tsutomu Nanmyo
  • Publication number: 20110263894
    Abstract: 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: Application
    Filed: December 22, 2009
    Publication date: October 27, 2011
    Applicant: BASF SE
    Inventors: Andreas Woelfert, Frank Grzonkowski, Harald Jachow, Guenter Renz
  • Patent number: 8008425
    Abstract: 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: Grant
    Filed: July 11, 2006
    Date of Patent: August 30, 2011
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Nobuyuki Kakiuchi, Hitoshi Furusho, Naoki Otani, Tatsuo Okauchi, Naoki Nakaie
  • Publication number: 20110172138
    Abstract: 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: Application
    Filed: August 18, 2009
    Publication date: July 14, 2011
    Applicant: ARKEMA FRANCE
    Inventors: Christian Forquy, Georges Fremy
  • Publication number: 20090127491
    Abstract: 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: Application
    Filed: July 11, 2006
    Publication date: May 21, 2009
    Applicant: Nissan Chemical Industries, Ltd.
    Inventors: Nobuyuki Kakiuchi, Hitoshi Furusho, Naoki Otani, Tatsuo Okauchi, Naoki Nakaie
  • Patent number: 6927305
    Abstract: 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: Grant
    Filed: March 20, 2003
    Date of Patent: August 9, 2005
    Assignee: Council of Scientific and Industrial Research
    Inventors: Boyapati Manoranjan Choudary, Kottapalli Koteswara Rao, Mahendar Koosam
  • Patent number: 6843978
    Abstract: 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: Grant
    Filed: May 24, 2002
    Date of Patent: January 18, 2005
    Assignees: Consejo Superior De Investigaciones Cientificas, Universidad Politecnica De Valencia
    Inventors: Avelino Corma Canós, Vicente Fornes Segui, Urbano Díaz Morales, Marcelo Eduardo Domine
  • Patent number: 6531629
    Abstract: 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: Grant
    Filed: May 15, 2001
    Date of Patent: March 11, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Eiermann, Christian Tragut, Klaus Ebel
  • Patent number: 6495714
    Abstract: 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: Grant
    Filed: August 3, 2001
    Date of Patent: December 17, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Halbritter, Hans-Josef Sterzel, Matthias Eiermann, Eva Freudenthaler
  • Patent number: 6187169
    Abstract: 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: Grant
    Filed: April 8, 1999
    Date of Patent: February 13, 2001
    Assignee: ATOFINA Chemicals, Inc.
    Inventors: Michael D. Gernon, Nicholas M. Martyak, Martin Nosowitz, Gary S. Smith
  • Patent number: 6124497
    Abstract: 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: Grant
    Filed: October 22, 1999
    Date of Patent: September 26, 2000
    Assignee: Innochem Inc.
    Inventor: Johnson Chen
  • Patent number: 6066760
    Abstract: 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: Grant
    Filed: March 31, 1994
    Date of Patent: May 23, 2000
    Assignee: Elf Atochem North America, Inc.
    Inventor: Steven Gabriel Schon
  • 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: 5912385
    Abstract: 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: Grant
    Filed: January 20, 1998
    Date of Patent: June 15, 1999
    Assignee: Tokai Denka Kogyo Kabushiki Kaisha
    Inventors: Kazuyoshi Kushibe, Hiromitsu Kobayashi, Hirohisa Nitoh, Hirotsugu Kitamura
  • Patent number: 5840972
    Abstract: 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: Grant
    Filed: February 22, 1995
    Date of Patent: November 24, 1998
    Assignee: Glaxo Wellcome Inc.
    Inventors: Rajnikant Patel, Amrik Singh Mahal, Donald Lloyd Winston Burford
  • Patent number: 5583253
    Abstract: 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: Grant
    Filed: March 27, 1991
    Date of Patent: December 10, 1996
    Inventors: Phyllis A. Henderson, Steven G. Schon, Carl Postuma
  • Patent number: 4987250
    Abstract: 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: Grant
    Filed: January 19, 1989
    Date of Patent: January 22, 1991
    Assignee: Union Oil Company of California
    Inventors: Dennis E. McGee, Ted S. Hallen
  • Patent number: 4956494
    Abstract: 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: Grant
    Filed: June 15, 1989
    Date of Patent: September 11, 1990
    Assignee: Pennwalt Corporation
    Inventors: Altaf Husain, Gregory A. Wheaton
  • Patent number: 4895977
    Abstract: 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: Grant
    Filed: December 12, 1988
    Date of Patent: January 23, 1990
    Assignee: Pennwalt Corporation
    Inventor: Martin Nosowitz