Carbon To Carbon Unsaturation In Reactant Patents (Class 568/408)
  • Patent number: 11345649
    Abstract: 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: Grant
    Filed: August 19, 2021
    Date of Patent: May 31, 2022
    Assignee: Chevron Phillips Chemical Company, LP
    Inventors: Jared L. Barr, Carlos A. Cruz, Masud M. Monwar, Kathy S. Clear, Max P. McDaniel
  • Patent number: 11142491
    Abstract: 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: Grant
    Filed: September 14, 2020
    Date of Patent: October 12, 2021
    Assignee: Chevron Phillips Chemical Company, LP
    Inventors: Jared L. Barr, Carlos A. Cruz, Masud M. Monwar, Kathy S. Clear, Max P. McDaniel
  • Patent number: 9815758
    Abstract: 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: Grant
    Filed: December 12, 2016
    Date of Patent: November 14, 2017
    Assignee: INTERNATIONAL FLAVORS & FRAGRANCES INC.
    Inventors: Avelino Corma Canós, Sara Iborra Chornet, Alexandra Velty, Manuel Querol Sans, Amadeo Fernández Miranda, Jaime Renovell Gomez
  • Publication number: 20140245658
    Abstract: 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: Application
    Filed: February 7, 2014
    Publication date: September 4, 2014
    Applicant: PIONEER ENERGY INC
    Inventors: John T. Henri, Jan Zygmunt, Mark Berggren, Robert Zubrin
  • Patent number: 8697917
    Abstract: 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: Grant
    Filed: September 18, 2012
    Date of Patent: April 15, 2014
    Assignee: Kellogg Brown & Root LLC
    Inventors: Theodor R. Wilks, Manish Bhargava, Eric Wing-Tak Wong
  • Patent number: 8664450
    Abstract: 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: Grant
    Filed: September 28, 2009
    Date of Patent: March 4, 2014
    Assignee: DSM IP Assets B.V.
    Inventors: Fabrice Aquino, Werner Bonrath, Rolf Kuenzi
  • Publication number: 20130237714
    Abstract: 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: Application
    Filed: September 7, 2012
    Publication date: September 12, 2013
    Applicant: SHELL OIL COMPANY
    Inventors: Sivakumar SADASIVAN VIJAYAKUMARI, Jeroen VAN WESTRENEN
  • Patent number: 8404901
    Abstract: 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: Grant
    Filed: March 13, 2009
    Date of Patent: March 26, 2013
    Assignee: BASF SE
    Inventors: Joaquim Henrique Teles, Dieter Baumann, Beatrice Röβler-Feigel
  • Publication number: 20130072723
    Abstract: 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: Application
    Filed: September 18, 2012
    Publication date: March 21, 2013
    Applicant: Kellogg Brown & Root LLC
    Inventor: Kellogg Brown & Root LLC
  • Patent number: 7692045
    Abstract: 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: Grant
    Filed: September 22, 2005
    Date of Patent: April 6, 2010
    Assignee: BASF Aktiengesellschaft
    Inventors: Joaquim Henrique Teles, Beatrice Roessler, Thomas Genger, Andreas Glass, Dieter Baumann, Jan-Martin Loening
  • Patent number: 7615668
    Abstract: 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: Grant
    Filed: October 18, 2004
    Date of Patent: November 10, 2009
    Assignee: Central Glass Co., Ltd.
    Inventors: Adam Alty, Frank Waters, Richard Du Boisson, Yokusu Kuriyama, Masamichi Maruta
  • Patent number: 7534921
    Abstract: 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: Grant
    Filed: October 8, 2005
    Date of Patent: May 19, 2009
    Assignee: BASF Aktiengesellschaft
    Inventors: Christoph Jäkel, Rocco Paciello
  • Patent number: 7462745
    Abstract: 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: Grant
    Filed: August 23, 2005
    Date of Patent: December 9, 2008
    Assignee: OXENO Olefinchemie GmbH
    Inventors: Franz Nierlich, Cornelia Borgmann, Dirk Roettger, Stephan Houbrechts, Dietrich Maschmeyer
  • Publication number: 20080269528
    Abstract: 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: Application
    Filed: October 8, 2005
    Publication date: October 30, 2008
    Inventors: Christoph Jakel, Rocco Paciello
  • Publication number: 20080255393
    Abstract: 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: Application
    Filed: September 22, 2005
    Publication date: October 16, 2008
    Applicant: BASF Aktiengesellschaft
    Inventors: Joaquim Henrique Teles, Beatrice Rossler, Thomas Genger, Andreas Glass, Dieter Baumann, Jan-Martin Loning
  • Patent number: 7405328
    Abstract: 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: Grant
    Filed: December 6, 2005
    Date of Patent: July 29, 2008
    Assignee: Solvay Fluor GmbH
    Inventors: Eckhard Hausmann, Oalf Boese, Johannes Eicher
  • Patent number: 7332092
    Abstract: 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: Grant
    Filed: March 7, 2007
    Date of Patent: February 19, 2008
    Assignees: Calgon Carbon Corporation, InnovaAroma SA
    Inventors: Chen-Chou Chiang, Elad Shabtai
  • Patent number: 6995291
    Abstract: 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: Grant
    Filed: September 22, 2003
    Date of Patent: February 7, 2006
    Assignee: Firmenich SA
    Inventor: Eric Walther
  • Publication number: 20020198411
    Abstract: 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: Application
    Filed: May 21, 2002
    Publication date: December 26, 2002
    Applicant: NIKKEN CHEMICALS CO., LTD.
    Inventors: Shin Tanikawa, Sou Matsubayashi, Michika Tanikawa, Toshiya Komatsu
  • Patent number: 6184420
    Abstract: 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: Grant
    Filed: September 10, 1998
    Date of Patent: February 6, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Joaquim Henrique Teles, Norbert Rieber, Klaus Breuer, Dirk Demuth, Hartmut Hibst, Stefan Kaeshammer, Heinz Etzrodt, Wulf Kaiser
  • Patent number: 5380755
    Abstract: 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: Grant
    Filed: July 24, 1992
    Date of Patent: January 10, 1995
    Assignee: The Du Pont Merck Pharmaceutical Company
    Inventors: Argyrios G. Arvanitis, Everett L. Scholfield
  • Patent number: 5225523
    Abstract: 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: Grant
    Filed: June 19, 1992
    Date of Patent: July 6, 1993
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Johannes J. Keijsper
  • Patent number: 5091587
    Abstract: 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: Grant
    Filed: November 19, 1990
    Date of Patent: February 25, 1992
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 5073659
    Abstract: 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: Grant
    Filed: August 10, 1990
    Date of Patent: December 17, 1991
    Assignee: Eisai Co., Ltd.
    Inventors: Kichisaburo Hamamura, Yutaka Ohnuki, Yukio Narabe, Yoshihiro Hisatake, Takashi Banba, Shizumasa Kijima
  • Patent number: 4612402
    Abstract: 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: Grant
    Filed: March 29, 1982
    Date of Patent: September 16, 1986
    Assignee: Allied Corporation
    Inventors: Deborah A. Muccigrosso, Frank Mares, Steven E. Diamond, Jeffrey P. Solar
  • Patent number: 4560804
    Abstract: 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: Grant
    Filed: July 25, 1983
    Date of Patent: December 24, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Chuen Y. Yeh, Charles Savini
  • Patent number: 4560805
    Abstract: 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: Grant
    Filed: July 25, 1983
    Date of Patent: December 24, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Chuen Y. Yeh, Charles Savini
  • Patent number: 4528401
    Abstract: 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: Grant
    Filed: July 25, 1983
    Date of Patent: July 9, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Chuen Y. Yeh, Charles Savini
  • Patent number: 4424399
    Abstract: 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: Grant
    Filed: September 9, 1980
    Date of Patent: January 3, 1984
    Assignee: Rhone-Poulenc Industries
    Inventor: Didier Morel
  • Patent number: 4412083
    Abstract: 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: Grant
    Filed: March 11, 1982
    Date of Patent: October 25, 1983
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Kenneth K. Light, William L. Schreiber, Joseph A. McGhie, Ronald P. Schreck, Takao Yoshida, Loren B. Schreiber, Ranya Muralidhara
  • Patent number: 4370497
    Abstract: 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: Grant
    Filed: August 7, 1980
    Date of Patent: January 25, 1983
    Inventors: Derek H. R. Barton, Steven V. Ley, Clive A. Meerholz