Carbon To Carbon Unsaturation In Reactant Patents (Class 568/408)
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Patent number: 11345649Abstract: Processes for converting an olefin reactant into a diol compound are disclosed, and these processes include the steps of contacting the olefin reactant and a supported chromium catalyst comprising chromium in a hexavalent oxidation state to reduce at least a portion of the supported chromium catalyst to form a reduced chromium catalyst, and hydrolyzing the reduced chromium catalyst to form a reaction product comprising the diol compound. While being contacted, the olefin reactant and the supported chromium catalyst can be irradiated with a light beam at a wavelength in the UV-visible spectrum. Optionally, these processes can further comprise a step of calcining at least a portion of the reduced chromium catalyst to regenerate the supported chromium catalyst.Type: GrantFiled: August 19, 2021Date of Patent: May 31, 2022Assignee: Chevron Phillips Chemical Company, LPInventors: Jared L. Barr, Carlos A. Cruz, Masud M. Monwar, Kathy S. Clear, Max P. McDaniel
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Patent number: 11142491Abstract: Processes for converting an olefin reactant into a diol compound are disclosed, and these processes include the steps of contacting the olefin reactant and a supported chromium catalyst comprising chromium in a hexavalent oxidation state to reduce at least a portion of the supported chromium catalyst to form a reduced chromium catalyst, and hydrolyzing the reduced chromium catalyst to form a reaction product comprising the diol compound. While being contacted, the olefin reactant and the supported chromium catalyst can be irradiated with a light beam at a wavelength in the UV-visible spectrum. Optionally, these processes can further comprise a step of calcining at least a portion of the reduced chromium catalyst to regenerate the supported chromium catalyst.Type: GrantFiled: September 14, 2020Date of Patent: October 12, 2021Assignee: Chevron Phillips Chemical Company, LPInventors: Jared L. Barr, Carlos A. Cruz, Masud M. Monwar, Kathy S. Clear, Max P. McDaniel
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Patent number: 9815758Abstract: A method of preparing 4-methyl-3-decen-5-one. The method includes the step of oxidizing 4-methyl-3-decen-5-ol in the presence of (i) oxygen and (ii) a metal catalyst, wherein the metal catalyst contains a catalytic metal deposited on nanoparticle support.Type: GrantFiled: December 12, 2016Date of Patent: November 14, 2017Assignee: INTERNATIONAL FLAVORS & FRAGRANCES INC.Inventors: Avelino Corma Canós, Sara Iborra Chornet, Alexandra Velty, Manuel Querol Sans, Amadeo Fernández Miranda, Jaime Renovell Gomez
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Publication number: 20140245658Abstract: Ketene chemistry and hydrogenation reactions are used to synthesize fuels and chemicals. Ketene from acetic acid is hydrogenated to form fuels and chemicals; acetic acid can be synthesized from synthesis gas which is produced from coal, biomass, natural gas, etc. In one embodiment, the present application discloses methods to selectively synthesize higher alcohols and hydrocarbons useful as fuels and industrial chemicals from syngas and biomass.Type: ApplicationFiled: February 7, 2014Publication date: September 4, 2014Applicant: PIONEER ENERGY INCInventors: John T. Henri, Jan Zygmunt, Mark Berggren, Robert Zubrin
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Patent number: 8697917Abstract: Methods and systems for producing low methanol concentration acetone are provided. The method can include oxidizing and cleaving cumene to produce a crude acetone product. The crude acetone product can be neutralized in a neutralization unit to produce a neutralized crude acetone product. The neutralized crude acetone product can be fractionated in an acetone fractionation column to produce an acetone product and an acetone bottoms product. Methanol can be removed from the acetone bottoms product to produce a methanol-depleted product. The methanol-depleted product can be introduced to the neutralization unit, a dephenolation unit, or both.Type: GrantFiled: September 18, 2012Date of Patent: April 15, 2014Assignee: Kellogg Brown & Root LLCInventors: Theodor R. Wilks, Manish Bhargava, Eric Wing-Tak Wong
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Patent number: 8664450Abstract: A process for the manufacture of gamma-delta-unsaturated ketones of formula (R1)(R2)C?CH—CH2—CH2—CO—R3 (I), wherein R1 is methyl or ethyl; R2 is a saturated or unsaturated linear or cyclic hydrocarbon residue and R3 is methyl or ethyl, by reacting a tertiary vinyl carbinol of formula (R1)(R2)C(OH)—CH?CH2 (II) with an isopropenyl methyl or ethyl ether of formula H3C—C(OR3)?CH2 (III) in the pre-sence of an ammonium salt as catalyst.Type: GrantFiled: September 28, 2009Date of Patent: March 4, 2014Assignee: DSM IP Assets B.V.Inventors: Fabrice Aquino, Werner Bonrath, Rolf Kuenzi
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Publication number: 20130237714Abstract: The present invention provides a process for preparing ethylene and/or propylene and an iso-olefin-depleted C4 olefinic product, comprising the steps of: a) providing a C4 hydrocarbon stream, comprising normal olefins and iso-olefins; b) subjecting the C4 hydrocarbon stream to an etherification process with methanol and/or ethanol wherein at least part of the iso-olefins are converted with methanol and/or ethanol to an tert-alkyl ether, and retrieving an etherification product stream; c) separating at least part of the etherification product stream into at least an ether-enriched stream and a first iso-olefin-depleted C4 olefinic product; d) converting at least part of the tert-alkyl ether in the ether-enriched stream to ethylene and/or propylene by contacting least part of the ether-enriched stream with a molecular sieve-comprising catalyst at a temperature in the range of from 350 to 1000° C. and retrieving a second olefinic product comprising ethylene and/or propylene.Type: ApplicationFiled: September 7, 2012Publication date: September 12, 2013Applicant: SHELL OIL COMPANYInventors: Sivakumar SADASIVAN VIJAYAKUMARI, Jeroen VAN WESTRENEN
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Patent number: 8404901Abstract: The present invention relates to a process for purifying a gas mixture comprising dinitrogen monoxide, at least comprising the at least partial condensation of a gas mixture G-I comprising dinitrogen monoxide to obtain a liquid composition C-1 comprising dinitrogen monoxide, and the contacting of the composition C-1 with a gas mixture M-1 to obtain a composition C-2 and a gas mixture M-2.Type: GrantFiled: March 13, 2009Date of Patent: March 26, 2013Assignee: BASF SEInventors: Joaquim Henrique Teles, Dieter Baumann, Beatrice Röβler-Feigel
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Publication number: 20130072723Abstract: Methods and systems for producing low methanol concentration acetone are provided. The method can include oxidizing and cleaving cumene to produce a crude acetone product. The crude acetone product can be neutralized in a neutralization unit to produce a neutralized crude acetone product. The neutralized crude acetone product can be fractionated in an acetone fractionation column to produce an acetone product and an acetone bottoms product. Methanol can be removed from the acetone bottoms product to produce a methanol-depleted product. The methanol-depleted product can be introduced to the neutralization unit, a dephenolation unit, or both.Type: ApplicationFiled: September 18, 2012Publication date: March 21, 2013Applicant: Kellogg Brown & Root LLCInventor: Kellogg Brown & Root LLC
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Patent number: 7692045Abstract: The present invention relates to a process for purifying a gas mixture comprising dinitrogen monoxide and to the use of a gas mixture purified in this way as an oxidant for olefins. In a further embodiment, the present invention also relates to a process for preparing ketones comprising the oxidation of an olefin with a gas mixture which has been purified in accordance with the invention and comprises dinitrogen monoxide.Type: GrantFiled: September 22, 2005Date of Patent: April 6, 2010Assignee: BASF AktiengesellschaftInventors: Joaquim Henrique Teles, Beatrice Roessler, Thomas Genger, Andreas Glass, Dieter Baumann, Jan-Martin Loening
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Patent number: 7615668Abstract: The present invention provides a novel method for preparing 4,4,4-trifluorobutane-2-one by providing a fluorobutene selected from the group consisting of 2,4,4,4-tetrafluoro-1-butene, (E)-1,1,1,3-tetrafluoro-2-butene, (Z)-1,1,1,3-tetrafluoro-2-butene, and mixture thereof; and reacting the fluorobutene(s) with a proton acid and water.Type: GrantFiled: October 18, 2004Date of Patent: November 10, 2009Assignee: Central Glass Co., Ltd.Inventors: Adam Alty, Frank Waters, Richard Du Boisson, Yokusu Kuriyama, Masamichi Maruta
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Patent number: 7534921Abstract: The present invention relates to a process for preparing optically active carbonyl compounds by asymmetrically hydrogenating ?,?-unsaturated carbonyl compounds in the presence of optically active transition metal catalysts which are soluble in the reaction mixture and have at least one carbon monoxide ligand. The present invention especially relates to a process for preparing optically active aldehydes or ketones, in particular citronellal, by asymmetrically hydrogenating the corresponding optically active ?,?-unsaturated aldehydes or ketones.Type: GrantFiled: October 8, 2005Date of Patent: May 19, 2009Assignee: BASF AktiengesellschaftInventors: Christoph Jäkel, Rocco Paciello
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Patent number: 7462745Abstract: Process for preparing 1-octa-2,7-dienyl derivatives by reacting a 1,3-butadiene-containing hydrocarbon mixture, in particular a C4 fraction from a cracker, with nucleophiles, in which acetylenically unsaturated compounds are removed from the starting hydrocarbon mixture by selective hydrogenation and a telomerization is subsequently carried out.Type: GrantFiled: August 23, 2005Date of Patent: December 9, 2008Assignee: OXENO Olefinchemie GmbHInventors: Franz Nierlich, Cornelia Borgmann, Dirk Roettger, Stephan Houbrechts, Dietrich Maschmeyer
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Publication number: 20080269528Abstract: The present invention relates to a process for preparing optically active carbonyl compounds by asymmetrically hydrogenating ?,?-unsaturated carbonyl compounds in the presence of optically active transition metal catalysts which are soluble in the reaction mixture and have at least one carbon monoxide ligand. The present invention especially relates to a process for preparing optically active aldehydes or ketones, in particular citronellal, by asymmetrically hydrogenating the corresponding optically active ?,?-unsaturated aldehydes or ketones.Type: ApplicationFiled: October 8, 2005Publication date: October 30, 2008Inventors: Christoph Jakel, Rocco Paciello
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Publication number: 20080255393Abstract: The present invention relates to a process for purifying a gas mixture comprising dinitrogen monoxide and to the use of a gas mixture purified in this way as an oxidant for olefins. In a further embodiment, the present invention also relates to a process for preparing ketones comprising the oxidation of an olefin with a gas mixture which has been purified in accordance with the invention and comprises dinitrogen monoxide.Type: ApplicationFiled: September 22, 2005Publication date: October 16, 2008Applicant: BASF AktiengesellschaftInventors: Joaquim Henrique Teles, Beatrice Rossler, Thomas Genger, Andreas Glass, Dieter Baumann, Jan-Martin Loning
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Patent number: 7405328Abstract: In a method or producing haloalkenone ethers by addition of a carboxylic acid halide to a vinyl ether and subsequent elimination of hydrogen halide, the improvement comprising carrying out the reaction in the absence of a base and/or in the presence of a stabilizer for the resulting alkenone, whereby higher yields of the desired alkenone product can be obtained.Type: GrantFiled: December 6, 2005Date of Patent: July 29, 2008Assignee: Solvay Fluor GmbHInventors: Eckhard Hausmann, Oalf Boese, Johannes Eicher
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Patent number: 7332092Abstract: E and Z isomers of alkene alcohols and/or alkene alcohol derivatives are separated by substantially continuously contacting an ion exchange medium which is ion exchanged with silver and/or copper ions with the feed stream comprising the E and Z isomers of at least one alkene alcohol and/or at least one alkene alcohol derivative, then removing a product stream having a higher concentration of the E or Z isomer of at least one alkene alcohol or derivative of the alkene alcohol relative to the concentration of the E or Z isomer of the alkene alcohol or derivative of the alkene alcohol in the feed stream.Type: GrantFiled: March 7, 2007Date of Patent: February 19, 2008Assignees: Calgon Carbon Corporation, InnovaAroma SAInventors: Chen-Chou Chiang, Elad Shabtai
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Patent number: 6995291Abstract: The present invention relates to the field of organic synthesis and more precisely to a process for the synthesis of an unsaturated aldehyde or ketone by oxidation of the corresponding alcohol. The oxidation is performed by a hypochlorite salt and a catalytic amount of a N-(2,2,6,6-tetraalkyl-4-piperidinyl-N-oxyl)-2-amino-1,3,5-triazine compound, preferably a N-oxyl derivative of one of the polymers known under the trademark Chimassorb® 944 or 2020.Type: GrantFiled: September 22, 2003Date of Patent: February 7, 2006Assignee: Firmenich SAInventor: Eric Walther
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Publication number: 20020198411Abstract: Allyl alcohols are converted into corresponding aldehydes or ketones in a high yield under a mild condition by using an inexpensive aluminum alkoxide as an Oppenauer oxidation catalyst and a hydride acceptor. Thus, there is provided an industrially useful method for converting allyl alcohols to corresponding aldehydes or ketones.Type: ApplicationFiled: May 21, 2002Publication date: December 26, 2002Applicant: NIKKEN CHEMICALS CO., LTD.Inventors: Shin Tanikawa, Sou Matsubayashi, Michika Tanikawa, Toshiya Komatsu
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Patent number: 6184420Abstract: Unsaturated ketones of the formulae Ia and Ib are prepared by a process consisting of the combination of the following reactions: a) The conventional reaction of an allyl alcohol of the formula IIa or a propargyl alcohol of the formula IIb with an isopropenyl ether of the formula III with formation of a ketal of the formula IV as a byproduct, b) preparation of the isopropenyl ether of the formula III by reacting a ketal of the formula IV with propyne or allene, or a mixture thereof in the gas phase at elevated temperatures in the presence of a heterogeneous catalyst containing zinc or cadmium together with silicon or oxygen, and c) feeding the ketal of the formula IV formed in the reaction (a) into stage (b) for the preparation of the isopropenyl ether of the formula III again.Type: GrantFiled: September 10, 1998Date of Patent: February 6, 2001Assignee: BASF AktiengesellschaftInventors: Joaquim Henrique Teles, Norbert Rieber, Klaus Breuer, Dirk Demuth, Hartmut Hibst, Stefan Kaeshammer, Heinz Etzrodt, Wulf Kaiser
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Patent number: 5380755Abstract: The present invention provides alkyl and alkylbenzyl ethers of substituted hydroquinones and pharmaceutical compositions containing them. The present invention further provides methods of using these compounds and compositions to inhibit monoamine oxidase, particularly monoamine oxidase B. The present invention further provides methods for the treatment of diseases involving monoamine oxidase.Type: GrantFiled: July 24, 1992Date of Patent: January 10, 1995Assignee: The Du Pont Merck Pharmaceutical CompanyInventors: Argyrios G. Arvanitis, Everett L. Scholfield
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Patent number: 5225523Abstract: A process for the preparation of low molecular weight polyketone polymers, wherein polymers of carbon monoxide with ethene and/or propene and optionally in addition with one or more other .alpha.-olefins are prepared by contacting the monomers in the presence of hydrogen with a catalyst containing a Group VIII metal and a tetraalkylbisphosphine ligand. The process may also be conducted in the presence of a liquid .alpha.-olefin diluent.Type: GrantFiled: June 19, 1992Date of Patent: July 6, 1993Assignee: Shell Oil CompanyInventors: Eit Drent, Johannes J. Keijsper
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Patent number: 5091587Abstract: A process for the preparation of ketones which comprises reacting a conjugated diolefin and water in the liquid phase in the presence of a catalyst system comprising:a) a group VIII metal compound, andb) a source of protons.Type: GrantFiled: November 19, 1990Date of Patent: February 25, 1992Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 5073659Abstract: A terpene compound having the formula (III) is produced by reacting an allylic halide having the formula (I) with a Grignard reagent having the formula (II) in the presence of anhydrous zinc chloride and a copper compound or an organic zinc halide compound having the formula (IV) in the presence of a copper compound, provided that when A-A is C-C, R' is hydrogen and when A-A is C=C, X is chlorine.Type: GrantFiled: August 10, 1990Date of Patent: December 17, 1991Assignee: Eisai Co., Ltd.Inventors: Kichisaburo Hamamura, Yutaka Ohnuki, Yukio Narabe, Yoshihiro Hisatake, Takashi Banba, Shizumasa Kijima
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Patent number: 4612402Abstract: A process for the oxidation of olefinically unsaturated substrates of the formula R--CH.dbd.CH-R' wherein R and R' are independently selected from members of the group consisting of H, alkyl, alkenyl, cycloalkyl, aryl and halo-, cyano- and ether-substituted alkyl, alkenyl, cycloalkyl and aryl which comprises reacting in the liquid phase said substrate with a rhodium nitro complex of the formula L.sub.n RhNO.sub.2, wherein n is 4 or 5 and wherein L.sub.n represents any combination of monodentate, bidentate, tridentate and tetradentate ligands such as to provide four or five bonding sites, for a time sufficient to produce an oxidized product of the formula RCH.sub.2 C(O)R' and a reduced product of the formula L.sub.n RhNO is disclosed. A preferred embodiment of the process wherein the rhodium nitro complex contains at least one ligand replaceable by olefin to be oxidized and operates to produce the oxidized product RCH.sub.2 C(O)R' in the absence of other Group VIII metals as co-catalyst is also disclosed.Type: GrantFiled: March 29, 1982Date of Patent: September 16, 1986Assignee: Allied CorporationInventors: Deborah A. Muccigrosso, Frank Mares, Steven E. Diamond, Jeffrey P. Solar
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Patent number: 4560804Abstract: An improved process is provided for forming ketones from the corresponding olefins by vapor phase oxidation of the olefin in the presence of water vapor, and optionally in the additional presence of molecular oxygen employing a heterogeneous catalyst comprising at least one member selected from the group consisting of Ce, Nd and La and compounds and complexes thereof, optionally containing at least one metal compound or complex selected from the group consisting of Group VIB metals and Group VIII noble metals, and mixtures thereof. It has been surprisingly found that these catalysts effect the formation of ketones in high selectivities with minimal selectivities to the undesirable carbon dioxide and carbon monoxide by-products.Type: GrantFiled: July 25, 1983Date of Patent: December 24, 1985Assignee: Exxon Research & Engineering Co.Inventors: Chuen Y. Yeh, Charles Savini
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Patent number: 4560805Abstract: An improved process is provided for forming ketones from the corresponding olefins in the vapor phase in the presence of water vapor employing a heterogeneous catalyst comprising rhenium compounds and complexes, optionally containing at least one metal compound or complex selected from the group consisting of Group VIB metals and Group VIII noble metals, and mixtures thereof. It has been surprisingly found that these catalysts effect the formation of ketones in high selectivities with minimal selectivities to the undesirable carbon dioxide and carbon monoxide by-products.Type: GrantFiled: July 25, 1983Date of Patent: December 24, 1985Assignee: Exxon Research & Engineering Co.Inventors: Chuen Y. Yeh, Charles Savini
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Patent number: 4528401Abstract: An improved process is provided for forming ketones from the corresponding olefins in the vapor phase in the presence of water vapor employing a heterogeneous catalyst comprising a molybdenum disulfide catalyst formed by the thermal decomposition of a thiomolybdate compound. It has been surprisingly found that these catalysts effect the formation of ketones in high selectivities with minimal selectivities to the undesirable carbon dioxide and carbon monoxide by-products.Type: GrantFiled: July 25, 1983Date of Patent: July 9, 1985Assignee: Exxon Research & Engineering Co.Inventors: Chuen Y. Yeh, Charles Savini
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Patent number: 4424399Abstract: New unsaturated fatty alcohols of the formula: ##STR1## in which n=2 or 4 are provided and are prepared by the novel process of reacting butadiene with water in the presence of a palladium salt and orthoboric acid, B(OH).sub.3, in a polar aprotic solvent.Type: GrantFiled: September 9, 1980Date of Patent: January 3, 1984Assignee: Rhone-Poulenc IndustriesInventor: Didier Morel
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Patent number: 4412083Abstract: Described is a process for preparing solanone and norsolanadione using chemical intermediates defined according to the generic structure: ##STR1## wherein X is one of the moieties: ##STR2## wherein R represents hydrogen or methyl; wherein Y represents one of the structures: ##STR3## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond; with the provisos that:(i) when Y is the moiety having the structure: ##STR4## then X is the moiety having the structure: ##STR5## (ii) when X is the moiety having the structure: ##STR6## then Y is the moiety having the structure:--C.tbd.N]In preparing solanone, the compound having the structure: ##STR7## or a mixture of compounds defined according to the structure: ##STR8## is reacted with methyl lithium and the resulting intermediate is hydrolyzed and the resulting compound is dehydrated.Type: GrantFiled: March 11, 1982Date of Patent: October 25, 1983Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, William L. Schreiber, Joseph A. McGhie, Ronald P. Schreck, Takao Yoshida, Loren B. Schreiber, Ranya Muralidhara
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Patent number: 4370497Abstract: The present invention relates to the use of telluroxides as mild and selective oxidizing agents serving to oxidize certain functions, notably >C.dbd.S groups, in the presence of other relatively easily oxidized functions which remain unaffected; telluroxides of interest as oxidizing agents include, for example, compounds of the formula: ##STR1## wherein R and R.sup.1, which may be the same or different, each represent an optionally substituted aryl or heterocyclic group; or R and R.sup.1 together with the tellurium atom therebetween represent a heterocyclic ring, which may contain one or more further heteroatoms, and which may carry substituents and/or fused aromatic rings.Type: GrantFiled: August 7, 1980Date of Patent: January 25, 1983Inventors: Derek H. R. Barton, Steven V. Ley, Clive A. Meerholz