Including Producing The Organic Halide Reactant Patents (Class 568/893)
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Patent number: 9102582Abstract: A method of making alcohols involves forming of alcohol esters from liquid alkane halides and a solution of metallic salts of organic acids to produce gaseous alcohol esters for reaction with magnesium or metal hydroxides to form the alcohol and the metal salt of the organic acids. In an improvement method liquid phase alcohol esters instead of gaseous alcohol esters are produced from liquid alkane halides and a solution of metal salts of organic acids whose alkane esters are less soluble in water than that of the alkane halide and treating of the alcohol ester formed with magnesium or metal hydroxides to form the alcohol and the metal salt of the organic acids.Type: GrantFiled: December 19, 2014Date of Patent: August 11, 2015Assignee: Sajet Development LLCInventors: Jorge Miller, Luisa Kling Miller
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Patent number: 8642817Abstract: The present invention includes a method for converting methane to methanol by providing a methane source to provide methane; contacting the methane with chlorine; exposing the methane to a light source to form methyl chloride; converting the methyl chloride with H20 to methanol and hydrochloric acid; converting the hydrochloric acid to chlorine; and purifying the methanol. The chemical cycle can be applied to the synthesis of alkane alcohols higher than methanol where appropriate.Type: GrantFiled: January 4, 2013Date of Patent: February 4, 2014Inventor: Peter J. Lucchesi
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Patent number: 8440868Abstract: An alcohol such as methanol is produced from an alkane such as methane and oxygen in a single step process using a heterogeneous catalyst. The catalyst comprises the chloride salts of copper, potassium, lead and zinc.Type: GrantFiled: March 6, 2012Date of Patent: May 14, 2013Inventor: John E. Stauffer
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Patent number: 8415512Abstract: Improvements in previously disclosed methods of and apparatuses for converting alkanes, alkenes, and aromatics to olefins, alcohols, ethers, and aldehydes includes: safety improvements, use of alternative feedstocks, process simplification, improvements to the halogenation step, improvements to the reproportionation step, improvements to the solid oxide reaction, improvements to solid oxide regeneration, improvements in separations, maintenance, start-up, shut-down, and materials of construction.Type: GrantFiled: October 13, 2010Date of Patent: April 9, 2013Assignee: GRT, Inc.Inventors: Jeffrey H. Sherman, Eric W. McFarland, Michael J. Weiss, Ivan Marc Lorkovic, Leroy E. Laverman, Shouli Sun, Dieter J. Schaefer, Galen D. Stucky, Peter C. Ford, Philip Grosso, Ashley W. Rreed, Michael F. Doherty
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Publication number: 20120259144Abstract: An alcohol such as methanol is produced from an alkane such as methane and oxygen in a single step process using a heterogeneous catalyst. The catalyst comprises the chloride salts of copper, potassium, lead and zinc.Type: ApplicationFiled: March 6, 2012Publication date: October 11, 2012Inventor: John E. STAUFFER
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Publication number: 20120215034Abstract: A method for converting a hydrocarbon feedstock into higher hydrocarbons is provided comprising reacting a hydrocarbon feedstock with a molecular halogen to form alkyl halides; reacting at least a portion of the alkyl halide in the presence of a catalyst to form higher hydrocarbons and a hydrogen halide; and converting at least a portion of the hydrogen halide into the molecular halogen via photoelectrocatalysis. Additional methods are also provided.Type: ApplicationFiled: April 27, 2012Publication date: August 23, 2012Inventor: Eric McFarland
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Patent number: 7838708Abstract: Improvements in previously disclosed methods of and apparatuses for converting alkanes, alkenes, and aromatics to olefins, alcohols, ethers, and aldehydes includes: safety improvements, use of alternative feedstocks, process simplification, improvements to the halogenation step, improvements to the reproportionation step, improvements to the solid oxide reaction, improvements to solid oxide regeneration, improvements in separations, maintenance, start-up, shut-down, and materials of construction.Type: GrantFiled: January 25, 2010Date of Patent: November 23, 2010Assignees: GRT, Inc., The Regents of the University of CaliforniaInventors: Jeffrey H. Sherman, Eric W. McFarland, Michael J. Weiss, Ivan Marc Lorkovic, Leroy E. Laverman, Shouli Sun, Dieter J. Schaefer, Galen D. Stucky, Peter C. Ford, Philip Grosso, Ashley W. Breed, Michael F. Doherty
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Patent number: 7812201Abstract: Methods and catalysts for producing alcohols, ethers, and/or alkenes from alkanes are provided. More particularly, novel caged, or encapsulated, metal oxide catalysts and processes utilizing such catalysts to convert alkanes to alcohols and/or ethers and to convert alcohols and/or ethers to alkenes are provided.Type: GrantFiled: October 1, 2009Date of Patent: October 12, 2010Assignee: Targa Resources, Inc.Inventors: Jorge Miller, Luisa Kling Miller
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Patent number: 7696390Abstract: A process is disclosed for the synthesis of methanol from methane comprising three reaction steps operated in tandem. In the first step methylene chloride is produced by the reaction of methane with oxygen and hydrogen chloride. In the second step, methylene chloride is hydrolyzed to formaldehyde, which is hydrogenated in the third step to provide the product methanol.Type: GrantFiled: June 10, 2008Date of Patent: April 13, 2010Inventor: John E. Stauffer
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Patent number: 7572927Abstract: A method of producing an o-disubstituted aromatic compound, containing: continuously conducting at least the following steps (a) to (d): (a) a step of mono-lithiating one halogen atom of an o-dihaloaromatic compound, using a first microreactor; (b) a step of making the thus-obtained monolithiated product to react with an electrophilic compound, using a second microreactor, to obtain a monosubstituted-monohaloaromatic compound; (c) a step of lithiating the other halogen atom of the o-dihaloaromatic compound, using a third microreactor; and (d) a step of making the thus-obtained lithiated product successively to react with an electrophilic compound, using a forth microreactor.Type: GrantFiled: March 12, 2007Date of Patent: August 11, 2009Assignee: Fujifilm CorporationInventors: Jun-ichi Yoshida, Aiichiro Nagaki, Toshiki Nokami
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Publication number: 20090118552Abstract: In a first sulfation step, 2-perfluoroalkylethyl iodide is brought into contact with fuming sulfuric acid to obtain a reaction mixture comprising 2-perfluoroalkylethyl sulfate and bis(2-perfluoroalkylethyl)sulfate. Then, in a first hydrolysis step, 2-perfluoroalkylethyl sulfate produced in the first sulfation step is hydrolyzed to obtain a reaction mixture comprising 2-perfluoroalkylethyl alcohol. In a second sulfation step, bis(2-perfluoroalkylethyl)sulfate produced in the first sulfation step is brought into contact with fuming sulfuric acid to obtain a reaction mixture comprising 2-perfluoroalkylethyl sulfate. Then, in a second hydrolysis step, 2-perfluoroalkylethyl sulfate produced in the second sulfation step is hydrolyzed to obtain a reaction mixture comprising 2-perfluoroalkylethyl alcohol. According to such procedures, 2-perfluoroalkylethyl alcohol can be obtained in a high yield.Type: ApplicationFiled: October 24, 2008Publication date: May 7, 2009Applicant: DAIKIN INDUSTRIES, LTD.Inventors: Yuuki MATSUDA, Takeomi Hirasaka, Takuya Ichida
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Patent number: 7361794Abstract: In a method of converting alkanes to their corresponding alcohols and ethers a vessel comprises a hollow, unsegregated interior defined first, second, and third zones. In a first embodiment of the invention oxygen reacts with metal bromide in the first zone to provide bromine; bromine reacts with the alkane in the second zone to form alkyl bromide; and the alkyl bromide reacts with metal oxide in the third zone to form the corresponding alcohol and/or ether. Metal bromide from the third zone is transported through the vessel to the first zone and metal oxide from the first zone is recycled to the third zone. A second embodiment of the invention differs from the first embodiment in that metal oxide is transported through the vessel from the first zone to the third zone and metal bromide is recycled from the third zone to the first zone.Type: GrantFiled: February 19, 2003Date of Patent: April 22, 2008Assignee: GRT, Inc.Inventor: Philip Grosso
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Patent number: 7161050Abstract: A reactant selected from the group consisting of alkanes, alkenes, alkynes, dienes, and aromatics is reacted with a halide selected from the group including chlorine, bromine, and iodine to form a first reaction product. The first reaction product is reacted with a solid oxidizer to form a product selected from the group including olefins, alcohols, ethers, and aldehydes, and spent oxidizer. The spent oxidizer is oxidized to form the original solid oxidizer and the second reactant which are recycled.Type: GrantFiled: August 19, 2003Date of Patent: January 9, 2007Assignees: GRT, Inc., The Regents of the University of CaliforniaInventors: Jeffrey H. Sherman, Eric W. McFarland, Michael J. Weiss, Ivan Marc Lorkovic, Leroy E. Laverman, Shouli Sun, Dieter J. Schaefer, Galen Stucky, Peter Ford
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Patent number: 7091387Abstract: This invention provides a process to convert alkanes to primary alcohols of the same carbon number. Carbon numbers of particular interest are C8 to C18.Type: GrantFiled: April 19, 2005Date of Patent: August 15, 2006Assignee: Shell Oil CompanyInventors: Howard Lam-Ho Fong, Lizbeth Olivia Cisneros Trevino, Brendan Dermot Murray, Manuel Luis Cano
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Patent number: 6545191Abstract: The specification discloses a process for the production of ethyl alcohol (ethanol), the process comprising first and second reaction steps operated in tandem. In the first reaction step, ethyl chloride, hydrogen chloride, perchloroethylene and oxygen are reacted in the presence of a catalyst, using ethane as a diluent, to yield reaction products comprising ethyl alcohol and hexachloroethane. Substantially all of the oxygen and hydrogen chloride reactants of this first reaction step are consumed. The ethyl alcohol is isolated from these reaction products. In the second reaction step, the hexachloroethane from the first reaction step is reacted with ethane to produce the ethyl chloride, hydrogen chloride, and perchloroethylene used as reactants in the first reaction step. These reaction products are supplied to the first reaction step, along with any unreacted ethane.Type: GrantFiled: June 13, 2002Date of Patent: April 8, 2003Inventor: John E. Stauffer
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Patent number: 6525230Abstract: In a method of converting alkanes to their corresponding alcohols and ethers a vessel comprises a hollow, unsegregated interior defined first, second, and third zones. In a first embodiment of the invention oxygen reacts with metal bromide in the first zone to provide bromine; bromine reacts with the alkane in the second zone to form alkyl bromide; and the alkyl bromide reacts with metal oxide in the third zone to form the corresponding alcohol and/or ether. Metal bromide from the third zone is transported through the vessel to the first zone and metal oxide from the first zone is recycled to the third zone. A second embodiment of the invention differs from the first embodiment in that metal oxide is transported through the vessel from the first zone to the third zone and metal bromide is recycled from the third zone to the first zone.Type: GrantFiled: April 2, 2002Date of Patent: February 25, 2003Assignee: GRT, Inc.Inventor: Philip Grosso
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Patent number: 6486368Abstract: Alcohols, ethers, and olefins are manufactured from alkanes by mixing an alkane and bromine in a reactor to form alkyl bromide and hydrogen bromide. The alkyl bromide only or the alkyl bromide and the hydrogen bromide are directed into contact with metal oxide to form an alcohol and/or an ether, or an olefin and metal bromide. The metal bromide is oxidized to form original metal oxide and bromine, both of which are recycled.Type: GrantFiled: January 24, 2002Date of Patent: November 26, 2002Assignees: GRT, Inc., The Regents of the University of CaliforniaInventors: Xiao Ping Zhou, Ivan Marc Lorkovic, Jeffrey H. Sherman
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Patent number: 6472572Abstract: Methanol and/or dimethyl ether are manufactured from methane by mixing methane and bromine in a reactor to form methyl bromide and hydrogen bromide. The methyl bromide only or the methyl bromide and the hydrogen bromide are directed into contact with metal oxide to form methanol and/or dimethyl ether and a metal bromide. The metal bromide is oxidized to form original metal oxide catalyst and bromine, both of which are recycled.Type: GrantFiled: June 20, 2001Date of Patent: October 29, 2002Assignees: GRT, Inc., The Regents of the University of CaliforniaInventors: Xiao Ping Zhou, Ivan Marc Lorkovic, Galen D. Stucky, Peter C. Ford, Jeffrey H. Sherman, Philip Grosso
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Patent number: 6465699Abstract: Alcohols, ethers, and olefins are manufactured from alkanes by mixing an alkane and bromine in a reactor to form alkyl bromide and hydrogen bromide. The alkyl bromide is directed into contact with metal oxide to form an alcohol and/or an ether, or an olefin and metal bromide. The metal bromide from the alkyl bromide metal oxide reaction is oxidized to form original metal oxide and bromine, both of which are recycled. The hydrogen bromide is separately directed into contact with metal oxide to form water and metal bromide. The metal bromide from the hydrogen bromide metal oxide is oxidized to form the original metal oxide which is recycled.Type: GrantFiled: March 11, 2002Date of Patent: October 15, 2002Assignees: GRI, Inc., The Regents of the University of CaliforniaInventor: Phil Grosso
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Patent number: 6465696Abstract: Alcohols, ethers, and olefins are manufactured from alkanes by mixing an alkane and bromine in a reactor to form alkyl bromide and hydrogen bromide. The alkyl bromide only or the alkyl bromide and the hydrogen bromide are directed into contact with metal oxide to form an alcohol and/or an ether, or an olefin and metal bromide. The metal bromide is oxidized to form original metal oxide and bromine, both of which are recycled.Type: GrantFiled: September 11, 2001Date of Patent: October 15, 2002Assignees: GRT, Inc., The Regents of the University of CaliforniaInventors: Xiao Ping Zhou, Galen D. Stucky, Jeffrey H. Sherman
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Patent number: 6462243Abstract: Alcohols and/or ethers are synthesized from alkanes by mixing an alkane and bromine in a reactor to form alkyl bromide and hydrogen bromide. The alkyl bromide is directed into contact with metal oxide to form alcohol and/or ether and a metal bromide. The metal bromide is oxidized to metal oxide and bromine, both of which are recycled.Type: GrantFiled: September 11, 2001Date of Patent: October 8, 2002Assignees: GRT, Inc., The Regents of the University of CaliforniaInventors: Xiao Ping Zhou, Ivan Marc Lorkovic, Galen D. Stucky, Peter C. Ford, Jeffrey H. Sherman, Philip Grosso
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Patent number: 6452058Abstract: An oxidative halogenation process involving contacting a reactant hydrocarbon selected from methane, a halogenated C1 hydrocarbon, or a mixture thereof with a source of halogen and, preferably, a source of oxygen in the presence of a rare earth halide or rare earth oxyhalide catalyst, so as to form a halogenated C1 hydrocarbon having a greater number of halogen substituents as compared with the reactant hydrocarbon. Preferably, the product is a monohalogenated methane, more preferably, methyl chloride. The oxidative halogenation process to form methyl halide can be integrated with downstream processes to produce valuable commodity chemicals, for example, methyl alcohol and/or dimethyl ether; light olefins, including ethylene, propylene, and butenes; higher hydrocarbons, including gasolines; vinyl halide monomer, and acetic acid. Hydrogen halide, which is a co-product of these downstream processes, can be recycled to the oxidative halogenation process.Type: GrantFiled: May 21, 2001Date of Patent: September 17, 2002Assignee: Dow Global Technologies Inc.Inventors: Albert E. Schweizer, Mark E. Jones, Daniel A. Hickman
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Patent number: 6388151Abstract: A method for synthesizing tetramethylcyclopentadiene from 2,3-dibromobutane is described. A 2-bromo-2-butene Grignard is reacted with an ethyl formate to produce a 3,5-dimethyl-2,5-heptadiene-4-ol magnesium bromide which is then quenched with acetic acid to produce 3,5-dimethyl-2,5-hepadiene-4-ol.Type: GrantFiled: November 24, 1998Date of Patent: May 14, 2002Assignee: Boulder Scientific CompanyInventors: Jeffrey M. Sullivan, Richard D. Crawford
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Patent number: 6137017Abstract: A process is provided for producing methyl alcohol from natural gas using chlorination technology. The process includes reacting methyl chloride, hydrogen chloride, oxygen and perchloroethylene in a catalytic reactor to give methanol product and hexachloroethane and using the C.sub.2 Cl.sub.6 to chlorinate methane of natural gas feedstock in multiple thermal chlorination reactors, each with a natural gas recycle loop. These reactors are arranged in a cross-flow reactor system whereby a gas purge from the first reactor is fed to the second, and so on if necessary until a last reactor, which is vented to the atmosphere by feeding a purge steam to the catalytic reactor.Type: GrantFiled: July 27, 1999Date of Patent: October 24, 2000Inventor: John E. Stauffer
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Patent number: 5998679Abstract: The present invention is directed to methods for converting lower alkanes and alkenes to the corresponding lower alkanols and diols. In the methods of the present invention, a gaseous halogen, preferably bromine, is produced by decomposing a metal halide in a liquid having a melting point below and a boiling point above the decomposition temperature of the metal halide. The preferred liquid is molten, hydrated ferric chloride maintained at a temperature between about 37-280.degree. C. The lower alkane or alkene is halogenated in a gas phase reaction with the produced halogen. The alkyl halide or alkyl dihalide is contacted with a metal hydroxide, preferably an aqueous solution of ferric hydroxide, to regenerate the metal halide and produce the corresponding lower alkanol or diol. The present invention is particularly efficient for converting methane to methanol using ferric bromide to provide the halogen.Type: GrantFiled: July 26, 1998Date of Patent: December 7, 1999Assignee: JLM Technology, Ltd.Inventor: Jorge Miller
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Patent number: 5854168Abstract: A new catalyst composition is provided for the synthesis of methyl alcohol by a catalytic reaction where methyl chloride, perchloroethylene, hydrogen chloride, and oxygen are converted to methyl alcohol and hexachloroethylene. The catalyst composition is an admixture of an iodine salt with copper chloride enhanced as needed by a chloride of iron, zinc, lead or bismuth or an admixture of an alkali metal bromine salt such as sodium bromide, potassium bromide and cesium bromide substituted for the iodine salt.Type: GrantFiled: November 13, 1997Date of Patent: December 29, 1998Inventor: John E. Stauffer
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Patent number: 5354916Abstract: The invention relates to a process for selectively producing alkyl halides from alkanes, such as methane and ethane at low temperatures and low pressures. Optional hydrolysis to the corresponding alcohols may follow. The process involves adding an alkane and an added halogen source to an aqueous solution in a homogeneous system in the presence of a transition metal halide containing complex, for a time, under conditions and in effective amounts that will permit the formation of alkyl monohalides.Type: GrantFiled: January 24, 1994Date of Patent: October 11, 1994Assignee: Exxon Research and Engineering CompanyInventors: Istvan T. Horvath, John M. Millar, Raymond A. Cook
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Patent number: 5243098Abstract: Lower alkanols are prepared from corresponding alkanes by reacting the lower alkane with a metal halide to produce a lower alkyl halide which, in turn, is reacted with magnesium oxide to form the corresponding lower alkanol. A continuous fluidized-bed system is provided for conducting the necessary reactions.Type: GrantFiled: November 4, 1992Date of Patent: September 7, 1993Assignee: Energia Andina Ltd.Inventors: Jorge P. Miller, Miguel Kling
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Patent number: 5185479Abstract: An improved method of producing methyl alcohol (methanol) from methane is provided using two reaction steps operated in tandem. In the first reaction step two chemical reactions occur simultaneously: a) perchloroethylene (CCl.sub.2 CCl.sub.2) is oxychlorinated with hydrogen chloride and oxygen to obtain hexachlorethane (CCL.sub.3 CCL.sub.3) and water, and b) methyl chloride (CH.sub.3 Cl) is hydrolyzed with water to give methyl alcohol and hydrogen chloride. In the second reaction step methane is chlorinated with hexachlorethane to produce methyl chloride, hydrogen chloride and perchloroethylene. By recycling the methyl chloride, hydrogen chloride, and regenerated perchloroethylene produced in the second step to the first step the process can be operated in a balanced mode whereby the internal consumption of hydrogen chloride is equal to its formation.Type: GrantFiled: April 21, 1992Date of Patent: February 9, 1993Inventor: John E. Stauffer
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Patent number: 5105030Abstract: Dihydromyrcenol is prepared from dihydromyrcenyl chloride by hydrolyzing dihydromyrcenyl chloride in an aqueous medium containing a base and a phase transfer catalyst in an amount of 0.001-10 mol %, based on the amount of dihydromyrcenyl chloride.Type: GrantFiled: June 11, 1991Date of Patent: April 14, 1992Assignee: Huels AktiengesellschaftInventors: Gerhard Wachholz, Heinz-Werner Voges
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Patent number: 4990696Abstract: Perchloroethylene is oxychlorinated to provide hexachloroethane which is reacted with methane to produce methyl chloride which is hydrolyzed to form methyl alcohol product and hydrogen chloride which is recycled to the oxychlorination step.Type: GrantFiled: May 29, 1990Date of Patent: February 5, 1991Inventor: John E. Stauffer
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Patent number: 4791222Abstract: Described is a novel process for preparing dihydromyrcenol defined according to the structure: ##STR1## or the acetate thereof comprising the steps of: (i) hydrogenating .alpha.-pinene to form .alpha.-pinane;(ii) pyrolizing the resulting .alpha.-pinane to form a mixture of hydrocarbons including dihydromyrcene (or, in the alternative, forming substantially the same mixture of hydrocarbons by other well known means);(iii) reacting the resulting pinane pyrolyzate or like mixture with hydrogen chloride gas in the presence of an acid catalyst, e.g., Lewis acid or protonic acid, to form a mixture of tertiary chlorides; then(iv) reacting the mixture of tertiary chlorides with water or acetic acid int he presence of a hydroxylation catalyst defined according to the formula:M.sub.P X.sub.Qwherein M represents an element selected from the group consisting of Zn, Ca, Mg, Mn and Co; wherein X represents O or an anion, e.g.Type: GrantFiled: July 31, 1984Date of Patent: December 13, 1988Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Stephen R. Wilson, Leonard Steinbach, Thomas O'Rourke
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Patent number: 4523040Abstract: This invention relates to solid acidic or metal catalyst-promoted halogenation of methane to produce methyl monohalides in high selectivity. Concurrent or simultaneous hydrolysis provides methyl alcohol and/or dimethyl ether in good yields.Type: GrantFiled: May 16, 1983Date of Patent: June 11, 1985Inventor: George A. Olah
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Patent number: 4421679Abstract: Described are methods for augmenting or enhancing the aroma of perfumes and perfumed articles by adding thereto perfume aroma augmenting or enhancing quantities of novel methyl substituted-2-oxohexane derivatives produced by dimerizing isoamylene (2-methyl-2-butene) and then oxidizing the resulting product using formic acid and hydrogen peroxide; and optionally reacting the resulting product with a methyl Grignard reagent such as methyl magnesium chloride followed by hydrolysis; as well as perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, hair preparations, perfumed polymers and deodorant compositions as well as bleaching compositions containing same.Also covered is the genus of compounds defined according to the structure: ##STR1## wherein R.sub.1 and R.sub.2 taken together represent oxygen; or wherein, taken separately, R.sub.1 is hydroxyl and R.sub.2 is methyl or R.sub.Type: GrantFiled: February 4, 1982Date of Patent: December 20, 1983Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Lambert Dekker, Frederick L. Schmitt, Augustinus G. Van Loveren
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Patent number: 4420423Abstract: Described are methods for augmenting or enhancing the aroma of perfumes and perfumed articles by adding thereto perfume aroma augmenting or enhancing quantities of novel methyl substituted-2-oxohexane derivatives produced by dimerizing isoamylene (2-methyl-2-butene); then oxidizing the resulting product using formic acid and hydrogen peroxide; then reducing the resulting ketone(s) with an alkali metal borohydride; and then, optionally, reacting the resulting alcohol(s) with acetic anhydride to form one or more esters; as well as perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, hair preparations, perfumed polymers and deodorant compositions as well as bleaching compositions containing same.Also covered is the genus of compounds defined according to the structure ##STR1## wherein R.sub.12 represents hydroxyl:--OH]or acetoxy having the structure: ##STR2## and wherein R.sub.3, R.sub.4, R.sub.5, R.Type: GrantFiled: February 4, 1982Date of Patent: December 13, 1983Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Lambert Dekker, Frederick L. Schmitt, Augustinus G. Van Loveren