Sulfur Bonded Directly To Sulfur (e.g., Disulfides, Etc.) Patents (Class 568/21)
  • Patent number: 5403961
    Abstract: A process for preparing a stabilized and deodorized organic polysulfide compound is provided which comprises contacting a crude polysulfide, in the presence of a solvent, optionally further in the presence of a basic compound, with a metal salt of an inorganic acid or a metal salt of an organic acid under conditions sufficient to produce the stabilized and deodorized polysulfide.
    Type: Grant
    Filed: November 22, 1993
    Date of Patent: April 4, 1995
    Assignee: Phillips Petroleum Company
    Inventor: James E. Shaw
  • Patent number: 5403960
    Abstract: A process for preparing, in high yield, a sulfurized olefinic product for use in lubricating oil compositions having a chlorine content of less than about 1000 ppm, a sulfur content of from about 40 to about 50 weight percent and a viscosity at 100.degree. C. of within the range of from about 5 to about 15 cSt.
    Type: Grant
    Filed: September 23, 1993
    Date of Patent: April 4, 1995
    Assignee: Ethyl Petroleum Additives, Inc.
    Inventors: Abbas Kadkhodayan, Paul G. Griffin
  • Patent number: 5349091
    Abstract: Solid waste materials comprising oxidatively-cured, solid polysulfide sealants containing spent oxidant, fillers, plasticizers, and other formulating aids are reverted to a liquid sealant comprising mercaptan-terminated polysulfides by reducing them with a liquid mercaptan-terminated polysulfide at temperatures ranging from about 50.degree. to about 110.degree. C. Upon the addition of fresh curing agent and recuring, the reclaimed sealant has satisfactory tensile strength and elongation properties.
    Type: Grant
    Filed: April 27, 1993
    Date of Patent: September 20, 1994
    Assignee: Morton International, Inc.
    Inventors: Michael J. Hallisy, John R. Gilmore, Steven J. Hobbs, Warren G. Duncan
  • Patent number: 5349076
    Abstract: Disclosed is an improved method of preparation of trifluoromethylthiocopper n a very highly purified state and its application to the synthesis of organic and inorganic compounds containing the trifluoromethylthio moiety. Biological testing has shown that dimethyl(trifluoromethylthio)arsine is one of the most potent lung irritants known.
    Type: Grant
    Filed: September 17, 1993
    Date of Patent: September 20, 1994
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventors: Shekar Munavalli, David I. Rossman
  • Patent number: 5324858
    Abstract: New sulfurized compounds, their preparation and their use are described. They correspond to the general formula: {[R--S.sub.X --(CH.sub.2).sub.n --].sub.z CH.sub.3-z --(CH.sub.2).sub.P --}.sub.2 S.sub.y, in which R represents a monovalent hydrocarbon radical with 1 to 30 carbon atoms, optionally functionalized; x is a number equal to or greater than 1; z is an integer equal to 1 or 2; when z=1, n is an integer from 0 to 3 and p is an integer from 0 to 3, with n+p being an integer from 0 to 3; when z=2, n is an integer from 1 to 3 and p is an integer from 0 to 3; and y is a number equal to or greater than 1, at last one of the numbers x and y being strictly greater than 1. These sulfurized compounds can be used as extreme-pressure and anti-wear additives in lubricating oils, in particular oils for gear systems and oil for working metals.
    Type: Grant
    Filed: October 28, 1992
    Date of Patent: June 28, 1994
    Assignee: Instiut Francais du Petrole
    Inventors: Ourida Aberkane, Maurice Born, Jean Luc Mielzoszynski, Daniel Paquer, Guy Barc
  • Patent number: 5312992
    Abstract: A process for removing sulfur from an organic sulfide containing three or more chemically bound sulfur atoms is disclosed wherein said sulfide is contacted with a defined catalyst at elevated temperature to increase the disproportionation rate and the corresponding sulfide of lower sulfur rank is continuously removed from the reaction zone.
    Type: Grant
    Filed: October 23, 1991
    Date of Patent: May 17, 1994
    Assignee: Elf Atochem North America, Inc.
    Inventors: Roger T. Clark, Michael J. Lindstrom, Glenn T. Carroll, Jeffrey H.-G. Yen
  • Patent number: 5312993
    Abstract: The invention relates to the manufacture of dimethyl disulphide from methyl mercaptan and sulphur. The process according to the invention is characterized in that it comprises:(a) a first reaction zone in which the methyl mercaptan and sulphur are introduced and reacted in the presence of a catalyst,(b) a degassing zone in which the products originating from the first reaction zone are treated to remove at least partially the dissolved hydrogen sulphide, and(c) a second reaction zone in which the products originating from the degassing zone are brought into contact with a catalyst.
    Type: Grant
    Filed: October 29, 1992
    Date of Patent: May 17, 1994
    Assignee: Elf Atochem S.A.
    Inventor: Emmanuel Arretz
  • Patent number: 5294743
    Abstract: The alkyl groups of dialkyl trisulfides are exchanged with the alkyl groups of mercaptans by reacting a tertiary dialkyl trisulfide with an alkyl mercaptan having a greater number of carbon atoms in its alkyl group than said trisulfide in the presence of an acidic or basic type catalyst for a time and a temperature sufficient to produce a dialkyl trisulfide having at least one transferred alkyl group from said mercaptan.
    Type: Grant
    Filed: March 9, 1993
    Date of Patent: March 15, 1994
    Assignee: Elf Atochem North America, Inc.
    Inventor: Stanley R. Sandler
  • Patent number: 5264631
    Abstract: A process is disclosed for the preparation of unsymmetrical dialkyl trisulfides by the reaction of dialkyl trisulfides and olefins in the presence of an acidic-type catalyst whereby alkyl groups are exchanged. Novel mixtures of symmetrical and unsymmetrical dialkyl trisulfides are also disclosed.
    Type: Grant
    Filed: March 9, 1993
    Date of Patent: November 23, 1993
    Assignee: Elf Atochem North America, Inc.
    Inventor: Stanley R. Sandler
  • Patent number: 5250737
    Abstract: A method for preparing an essentially chlorine free additive mixture for oleaginous fluids containing less than 15 wt. % dialkyl higher-polysulfides, the process comprising: a) forming a reaction mass comprising olefin, a sulfur source, and a catalyst; b) heating the reaction mass to a temperature and for a period of time which is sufficient to form a mixture of olefin, alkyl mercaptan, dialkyl disulfide, dialkyl trisulfide and dialkyl higher-polysulfides; and c) refluxing the reaction mass obtained in (b) at a temperature and for a period of time which are sufficient to convert at least a portion of the dialkyl higher-polysulfides to dialkyl trisulfide so as to obtain the additive mixture containing less than 15 wt. % dialkyl higher-polysulfides.
    Type: Grant
    Filed: January 31, 1992
    Date of Patent: October 5, 1993
    Assignee: Ethyl Corporation
    Inventor: Nubar Ozbalik
  • Patent number: 5218147
    Abstract: A process for preparing a stable polysulfide compound, synthesized by reacting a mercaptan with elemental sulfur in the presence of a basic catalyst, having reduced mercaptan sulfur content is provided which comprises contacting the crude polysulfide with an alkylene oxide in the presence of a tetraalkylammonium hydroxide or a basic inorganic catalyst in a solvent.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: June 8, 1993
    Assignee: Phillips Petroleum Company
    Inventor: James E. Shaw
  • Patent number: 5208382
    Abstract: The copper corrosiveness of organic sulfides is reduced by treating them with an alkali metal-containing or alkaline earth metal-containing substance capable of dissolving elemental sulfur (e.g., sodium hydroxide, sodium sulfide, etc.). The process is conducted in the presence of a phase transfer catalyst in an aqueous liquid reaction medium. Experiments have shown that it is possible by use of this process to reduce the copper corrosiveness to a level below that exhibited by a product formed by treating the same initial organic sulfide in the same way but in the absence of a phase transfer catalyst.
    Type: Grant
    Filed: January 29, 1992
    Date of Patent: May 4, 1993
    Assignee: Ethyl Petroleum Additives, Inc.
    Inventors: Edmund F. Perozzi, John F. Sieberth
  • Patent number: 5206439
    Abstract: Product from the reaction of mercaptan with sulfur in the presence of a basic catalyst is treated by contacting with an alcohol-based solution containing an oxidizing agent and an inorganic basic catalyst followed by the recovery of a purified polysulfide product.
    Type: Grant
    Filed: January 27, 1992
    Date of Patent: April 27, 1993
    Assignee: Phillips Petroleum Company
    Inventor: James E. Shaw
  • Patent number: 5174922
    Abstract: The invention provides a process of reducing the copper corrosiveness of dihydrocarbyl polysulfides by treating them with an alkali metal-containing or alkaline earth metal-containing substance capable of dissolving elemental sulfur (e.g., sodium hydroxide, sodium sulfide, etc.). The process is conducted in a liquid reaction medium composed of a mixture of water and at least one water-soluble alcohol. Experiments have shown that it is possible by use of this process to reduce the copper corrosiveness to a level below that exhibited by a product formed by treating the same initial dihydrocarbyl polysulfide in the same way but in a liquid medium composed solely of water.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: December 29, 1992
    Assignee: Ethyl Petroleum Additives, Inc.
    Inventors: Edmund F. Perozzi, Andrew G. Papay
  • Patent number: 5155275
    Abstract: This invention relates to a process for preparing polysulfide product generally containing an average of 3 to 6 sulfur atoms in high yield which degrades minimally over extended time periods. Minimal degradation is accomplished by a unique treatment process wherein chemical species, most notably unreacted mercaptans and catalysts which apparently promote degradation, are selectively removed from the polysulfide crude product.
    Type: Grant
    Filed: August 21, 1991
    Date of Patent: October 13, 1992
    Assignee: Phillips Petroleum Company
    Inventor: James E. Shaw
  • Patent number: 5149879
    Abstract: A lipid peroxidation inhibitor contains a polysulfide compound represented by formula (I) as an active ingredient:R.sup.1 --(S).sub.m --R.sup.2 (I)wherein R.sup.1 and R.sup.2 are same or different hydrocarbon chains having 1 to 16 carbon atoms and m is an integer of 3 to 10. Among compounds (I) are found novel which are:R.sup.3 --(S).sub.n --R.sup.4 (II)wherein R.sup.3 and R.sup.4 are same or different lower alkenyl groups and n is an integer of 6 to 10. Pharmaceutical compositions which contain a polysulfide compound represented by formula (I) as an active ingredient, for preventing and curing diseases of thrombosis, arteiosclerosis, liver troubles, pulmonary edema, skin troubles, eye troubles and aging are also disclosed.
    Type: Grant
    Filed: June 21, 1991
    Date of Patent: September 22, 1992
    Assignee: Wakunaga Seiyaku Kabushiki Kaisha
    Inventors: Shoji Awazu, Toshiharu Horie, Yukihiro Kodera, Shinji Nagae, Hiromichi Matsuura, Yoichi Itakura
  • Patent number: 5104910
    Abstract: Described herein is an isocyanate-reactive compound containing at least one linkage of the formula:--X--X--wherein X is independently in each occurrence --NR--, --S--, or --O--; R is independently in each occurrence hydrogen, C.sub.1-10 alkyl, aryl, or arylene; and at least one N, S, or O atom of the above formula is bonded to an aryl or arylene group. Also disclosed are isocyanate-reactive compositions containing the above compound and flexible polyurethane foams prepared therefrom.
    Type: Grant
    Filed: January 3, 1991
    Date of Patent: April 14, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert B. Turner, Ralph D. Priester, Jr., Stephen R. Burkes
  • Patent number: 5091593
    Abstract: A process for removing sulfur from an organic sulfide containing three or more chemically bound sulfur atoms is disclosed wherein said sulfide is contacted with a defined catalyst at elevated temperature to increase the disproportionation rate and the corresponding sulfide of lower sulfur rank is continuously removed from the reaction zone.
    Type: Grant
    Filed: May 26, 1989
    Date of Patent: February 25, 1992
    Assignee: ATOCHEM North America, Inc.
    Inventors: Michael J. Lindstrom, Glenn T. Carroll, Jeffrey Hsing-Gan Yen, Roger T. Clark
  • Patent number: 5068445
    Abstract: The invention relates to the preparation of organic disulphides and polysulphides by the action of sulphur on a mercaptan or on a polysulphide which is lower in sulphur, in the presence of a basic catalyst.In the process according to the invention, an anion exchange resin is used as catalyst.
    Type: Grant
    Filed: April 3, 1989
    Date of Patent: November 26, 1991
    Assignee: Societe Nationale Elf Aquitaine (Production)
    Inventor: Emmanuel Arretz
  • Patent number: 5051198
    Abstract: The present invention deals with compositions containing sulfur and oxygen which are useful in lubricants and automatic transmission fluids.
    Type: Grant
    Filed: January 4, 1990
    Date of Patent: September 24, 1991
    Assignee: The Lubrizol Corporation
    Inventor: Mary F. Salomon
  • Patent number: 5006271
    Abstract: Sulfurized propylene based lube olefin derivatives are superior lubricating fluids with internal synergistic multifunctional extreme pressure/antiwear and antioxidant properties as well as multifunctional extreme pressure/antiwear additives for both mineral and synthetic lubricating oils as well as fuels.
    Type: Grant
    Filed: December 30, 1988
    Date of Patent: April 9, 1991
    Assignee: Mobil Oil Corporation
    Inventors: Noyes L. Avery, Linda A. Benjamin, Andrew G. Horodysky, Derek A. Law
  • Patent number: 4937385
    Abstract: A process is disclosed for continuously preparing dialkyl disulfides and dialkyl polysulfides by reacting at elevated temperature and in the presence of a solid, particulate catalyst an alkene and hydrogen sulfide in a first reaction zone, and then passing the reactor effluent into a second reaction zone where it is reacted at elevated temperature with molten, elemental sulfur in the presence of a solid, particulate catalyst.
    Type: Grant
    Filed: May 18, 1988
    Date of Patent: June 26, 1990
    Assignee: Pennwalt Corporation
    Inventors: Bernard Buchholz, Edward J. Dzierza, Robert B. Hager
  • Patent number: 4839069
    Abstract: Compositions of olefin polysulfides having an increased solubility in mineral oils and in synthetic oils, particularly of the hydrogenated polyalphaolefin (P.A.O.) type, are disclosed.They are prepared more particularly by reacting a sulfur monochloride with a monoolefin (e.g. isobutene) so as to form an addition product, called an adduct, which is then reacted with an alkali metal or ammonium polysulfide, obtained, for example, by reacting a mercaptan with an alkali hydroxide or ammonia in the presence of elemental sulfur. These compositions of olefin polysulfides can be used as extreme-pressure additives in gear-oils or in metal-working oils.
    Type: Grant
    Filed: October 16, 1987
    Date of Patent: June 13, 1989
    Assignee: Institut Francais du Petrole
    Inventors: Maurice Born, Lucienne Briquet, Jacques Lallement, Guy Parc
  • Patent number: 4827040
    Abstract: The polysulphide is heated with a substance capable of dissolving elemental sulphur. After cooling, the polysulphide reduced to a lower numbver of S atoms is separated from the substance, which can be recovered.An important use consists in converting the polysulphide to the form of dimethyl disulphide, the solvent used for the dissolution of sulphur deposited in conduits, particularly those used for natural gas.
    Type: Grant
    Filed: March 24, 1986
    Date of Patent: May 2, 1989
    Assignee: Societe Nationale Elf Aquitaine (Production)
    Inventors: Yves Labat, Guy Desgrandchamps
  • Patent number: 4804485
    Abstract: A composition, useful for dissolving sulfur, which comprises a major amount of a disulfide or polysulfide and a catalyst comprising one or more polyalkyleneoxyamines or polyamines, and methods for using the composition in a system to prevent sulfur-plugging, are disclosed.
    Type: Grant
    Filed: May 8, 1987
    Date of Patent: February 14, 1989
    Assignee: Pennwalt Corporation
    Inventors: Glenn T. Carroll, Michael J. Lindstrom, William J. Tuszynski
  • Patent number: 4802912
    Abstract: This invention relates to haloalkyl-sulfenoxyl-2, 3-dibromopropane compounds and their use as antidotes for thiocarbamate herbicides.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: February 7, 1989
    Assignee: Stauffer Chemical Co.
    Inventor: Don R. Baker
  • Patent number: 4795576
    Abstract: The disclosed polysulfided olefin compositions can be used in particular as extreme-pressure additives for lubricants. They are prepared by a process comprising the steps of:(1) reacting sulfur monochloride and/or dichloride with at least one monoolefin having 2 to 5 carbon atoms (generally isobutene) to form an "adduct"; (2) contacting said "adduct" jointly with an unsaturated monohalogenated hydrocarbon compound, in a proportion corresponding to a number of halogen gram-atoms from about 1 to 70% of the number of halogen gram-atoms of the assembly "monohalogenated hydrocarbon compound+adduct", with a sulfur compound (e.g. alkaline sulfide, hydrogenosulfide or polysulfide) and, mostly, element sulfur, in a proportion of 0 to 7 gram-atoms per mole of sulfur compound, within an aqueous or hydroalcoholic medium; (3) heating the mixture and, after settling in 2 phases, separating the organic phase containing the polysulfided olefin, and (4) optionally treating the obtained product with a base.
    Type: Grant
    Filed: October 17, 1986
    Date of Patent: January 3, 1989
    Assignee: Institut Francais du Petrole
    Inventors: Maurice Born, Lucienne Briquet, Guy Parc, Daniel Paquer
  • Patent number: 4764297
    Abstract: A process for producing a sulfurized olefin product substantially free of ash containing waste is disclosed. The process involves dehydrohalogenation of an olefin/sulfur halide complex by contacting the complex with a protic solvent in the absence of any metal ion. The process allows for the solvolytic dehydrohalogenation of the complex. The sulfurized olefin product obtained is isolated and may be subjected to further processing to remove any remaining halides. The resulting sulfurized olefin is a useful additive in lubricating oils.
    Type: Grant
    Filed: March 20, 1987
    Date of Patent: August 16, 1988
    Assignee: The Lubrizol Corporation
    Inventors: Roger L. Sowerby, Stephen A. DiBiase
  • Patent number: 4727199
    Abstract: Active-hydrogen compounds, for example, primary and secondary alcohols or diols, are alkoxylated, for example, ethoxylated, using solid anion-bound metal oxide catalysts, such as, zirconium oxysulfate catalyst. Hydrous zicronium oxide is treated with solutions of sulfate phosphate, nitrate or tetrafluoroborate and calcined in air at 300.degree. to 950.degree. C. to produce highly active heterogeneous alkoxylation catalysts. The amorphous catalysts afford narrow molecular weight products. The catalyst can be removed from the product by filtration and reused with no significant loss in activity. Reaction temperatures of 50.degree. to 140.degree. C. are employed for alkoxylation.
    Type: Grant
    Filed: July 10, 1985
    Date of Patent: February 23, 1988
    Assignee: Union Carbide Corporation
    Inventor: Stephen W. King
  • Patent number: 4645610
    Abstract: A method for the preparation of olefin polysulfides that can be used in particular as extreme pressure additives for lubricants is described. This method comprises: (1) reacting sulfur monochloride or dichloride with at least one mono-olefin containing 2 to 5 carbon atoms (in general isobutene) resulting in the formation of an adduct; (2) bringing into contact said adduct, conjointly with a hydrocarbyl halide, with a sulfur compound (for example, alkaline sulfides, hydrosulfides or polysulfides) and, in most cases, elemental sulfur, in an aqueous or aqueous-alcoholic medium; (3) heating the mixture and, after it has settled into two phases, separating the organic phase containing the olefin polysulfide; and if necessary (4) treating the product obtained with a base.The olefin polysulfides obtained contain a high proportion of sulfur, have a satisfactory viscosity and are sufficiently soluble in mineral oils as well as synthetic oils to be used as extreme pressure additives in the formulation of gear oils.
    Type: Grant
    Filed: April 19, 1985
    Date of Patent: February 24, 1987
    Assignee: Institut Francais du Petrole
    Inventors: Maurice Born, Guy Parc, Lucienne Briquet, Daniel Paquer
  • Patent number: 4564709
    Abstract: Dialkyl-trisulfides having a minimum grade of copper-strip corrosivity which are suitable as extreme-pressure additives, are produced at high selectivity by reacting alkyl-mercaptans and sulfur at a quantitative ratio in a range of 0.5 to 1.0 gram atom of sulfur to 1 mol of alkyl-mercaptan in the presence of magnesium oxide as catalyst.
    Type: Grant
    Filed: October 7, 1983
    Date of Patent: January 14, 1986
    Assignee: Pennwalt Corporation
    Inventors: Yuichiro Koyama, Hiroshi Nakazawa, Toshiaki Yamashita, Hitoshi Moriyama
  • Patent number: 4492805
    Abstract: Difficultly flammable polyarylene ether resins containing phosphorus having the structure ##STR1## and methods for making the same.
    Type: Grant
    Filed: January 26, 1983
    Date of Patent: January 8, 1985
    Assignee: Rohm GmbH
    Inventors: Siegmund Besecke, Gunter Schroder, Werner Ude, Winfried Wunderlich
  • Patent number: 4402862
    Abstract: The invention relates to the stabilization against water uptake of hygroscopic salts useful as catalysts by formation of anhydrous adducts with particulate support materials in order to facilitate manipulation and storage. The adducts comprise a particulate support material and a hygroscopic salt of a species of formula R.sup.1 R.sup.2 R.sup.3 R.sup.4 N, R.sup.1 R.sup.2 R.sup.3 R.sup.4 P, R.sup.1 R.sup.2 R.sup.3 R.sup.4 As, wherein R.sup.1 R.sup.4 which may be identical or different represent hydrogen or alkyl or aryl groups, or of Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, Cu.
    Type: Grant
    Filed: May 20, 1982
    Date of Patent: September 6, 1983
    Assignee: National Research Development Corporation
    Inventor: James H. Clark
  • Patent number: 4395415
    Abstract: 4-Nitro-2-trichloromethylbenzenesulfenic acid derivatives of the formula ##STR1## where R.sup.1 is nitroimidazolyl, which is substituted by alkyl, phenyl or benzyl, or R.sup.1 is S-alkyl, which is substituted by an S--S-phenyl radical, itself substituted in the phenyl moiety by nitro and trichloromethyl, or which is substituted by --O--CO--R.sup.2, where R.sup.2 is unsubstituted or substituted alkyl, unsubstituted or phenyl-substituted alkenyl, or unsubstituted or chlorine- or nitro-substituted phenyl, or monoalkylamino or dialkylamino, or unsubstituted or mono-chlorine-substituted or polychlorine-substituted aminophenyl, or R.sup.1 is --S--R.sup.3, where R.sup.3 is unsubstituted or carboxyl-substituted aryl, triazolyl, unsubstituted or alkyl-substituted thiadiazolyl, unsubstituted or alkyl-, cyano- or oxo-substituted pyridyl, or unsubstituted or alkyl-, amino-, hydroxy- or oxo-substituted pyrimidinyl, and fungicides containing these compounds.
    Type: Grant
    Filed: April 21, 1981
    Date of Patent: July 26, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Hagen, Hans Ziegler, Celia J. Mappes, Ernst-Heinrich Pommer
  • Patent number: 4355183
    Abstract: Inhibition of the formation of color bodies and color-forming materials and other contaminants and/or decolorization of discolored sulfur-containing organic compounds containing divalent sulfur by addition of a small amount of oxalic acid.
    Type: Grant
    Filed: August 8, 1979
    Date of Patent: October 19, 1982
    Assignee: Phillips Petroleum Company
    Inventors: Martin E. Nash, Edward E. Huxley
  • Patent number: 4337359
    Abstract: A process for the preparation of a dimethyl polysulphide of the formulaCH.sub.3 --S.sub.x --CH.sub.3in whichx is at least 1, comprising reacting a polysulphide of the formulaM.sub.y S.sub.xin whichM represents an alkali metal atom or alkaline earth metal atom, andy is 1 or 2, with O,O,O-trimethyl thiophosphate of the formula(CH.sub.3 O).sub.3 P.dbd.S.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: June 29, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hermann Arold, Siegbert Humburger, Hans-Joachim Diehr, Helmut Porkert
  • Patent number: 4307031
    Abstract: A method for producing a mixture of a dithiodibenzoate, a dithiocarbonate, and a trithiocarbonate, is disclosed. The method includes diazotizing an amine having the formula ##STR1## where R is hydrogen, or an alkyl group having not more than 4 carbon atoms, and coupling the resulting diazonium with at least 1 gram-mole of carbon disulfide per gram-mole of the diazonium in the presence of a copper catalyst. Under appropriate conditions, which include a reaction temperature in the range of 10.degree.-32.degree. C., sufficient time for full coupling to occur, and dissolving of the CS.sub.2 in a suitable water-miscible solvent such as methanol, coupling to said mixture readily occurs. The coupling products are then dissolved and removed by use of a water-immiscible inert solvent.
    Type: Grant
    Filed: May 19, 1980
    Date of Patent: December 22, 1981
    Assignee: The Sherwin-Williams Company
    Inventor: Lubomir Vacek
  • Patent number: 4245125
    Abstract: Compounds of the formula IA.multidot.m B (I)whereinA is a compound of the formula II or III ##STR1## m is a rational number between 0.1 and 4.0, and B is H.sub.2 O.sub.2, N.sub.2 H.sub.4 or NH.sub.2 OH, andR.sub.1 is an unsubstituted or substituted aliphatic or aromatic hydrocarbon radical which has 3-30 C atoms and which can be interrupted by oxygen or sulfur atoms,R.sub.2 is hydrogen or C.sub.1 -C.sub.30 alkyl,X is --O-- or --SO.sub.2 -- and, in the case where B is N.sub.2 H.sub.4 or NH.sub.2 OH, also --S-- or --SO--,Y is the direct bond, ##STR2## Q is --CH.sub.2, --CH(OH)--CH.sub.2 -- or --CH(CH.sub.2 --OH)--, and n is 1, 2, 3, 4, 5, 6, 7 or 8.
    Type: Grant
    Filed: May 10, 1979
    Date of Patent: January 13, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Hans-Helmut Friedrich
  • Patent number: 4218332
    Abstract: A novel class of compounds has been prepared comprising the tetrasulfides of C.sub.18 hydrocarbons, C.sub.18 fatty acids, and C.sub.18 fatty and alkyl and triglyceride esters. These tetrasulfides are useful as extreme pressure lubricant additives and show potential as replacements for sulfurized sperm whale oil.
    Type: Grant
    Filed: March 20, 1979
    Date of Patent: August 19, 1980
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Arthur W. Schwab, Lyle E. Gast, Harold E. Kenney