Unsaturated Hydrocarbon Reactant Patents (Class 568/365)
  • Patent number: 9656250
    Abstract: The present invention relates to a method for preparing an iodine-doped TiO2 nano-catalyst and use of the catalyst in heterogeneously catalyzing configuration transformation of trans-carotenoids. The iodine-doped TiO2 nano-catalyst is prepared by a sol-gel process using a titanate ester as a precursor and an iodine-containing compound as a dopant in the presence of a diluent, inhibitor and complexing agent. The catalyst exhibits high activity for isomerization of the trans-carotenoids into their cis-isomers within a short catalytic time. The catalyst can be easily prepared and is highly efficient, economical, recyclable and environmentally friendly.
    Type: Grant
    Filed: February 10, 2015
    Date of Patent: May 23, 2017
    Assignee: JIANGNAN UNIVERSITY
    Inventors: Lianfu Zhang, Qingrui Sun, Hongxiao Yan
  • Publication number: 20150094495
    Abstract: In a process for separating a mixture comprising cyclohexanone and phenol, at least a portion of the mixture is distilled in the presence of a solvent including at least two alcoholic hydroxyl groups attached to non-adjacent saturated carbon atoms, water, and in the presence or absence of a hemiketal defined by the formula (I) or the formula (II): wherein R1, the same or different at each occurrence, is independently an alkylene group having from 2 to 10 carbon atoms, R2 is an alkylene group having from 4 to 10 carbon atoms and/or R3 is hydrogen or the following group: and in the presence or absence of an enol-ether derived from the hemiketal defined by the formula (I) or the formula (II), wherein the total concentration of the hemiketal and enol-ether, expressed in term of weight percentage of the total weight of the feed to the distilling step, is at most 0.01%.
    Type: Application
    Filed: April 9, 2013
    Publication date: April 2, 2015
    Applicant: ExxonMobil Chemical Company Patents Inc.
    Inventors: Keith H. Kuechler, Francisco M. Benitez, Krystle J. Chavez, Christopher L. Becker, John L. Heidman
  • Publication number: 20140323767
    Abstract: The present invention relates to an improved process for the production of 1,3,3-trimethyl-2-(3-methylpent-2-en-4-ynyl)cyclohex-1-ene, highly enriched in the Z-isomer, and the use of such compounds in organic syntheses, especially in processes forming intermediates (building blocks) the synthesis of vitamin A or ?-carotene or other carotenoids, e.g. canthaxanthin, astaxanthin or zeaxanthin.
    Type: Application
    Filed: June 14, 2012
    Publication date: October 30, 2014
    Applicant: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Thomas Netscher, Jan Schütz, Bettina Wüstenberg
  • Publication number: 20140058089
    Abstract: Methods and systems are provided for converting methane in a feed stream to acetylene. The method includes removing at least a portion of sulfur containing compounds from a hydrocarbon stream. The hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream may be treated to convert acetylene to another hydrocarbon process. The method according to certain aspects includes controlling the level of sulfur containing compounds in the hydrocarbon stream.
    Type: Application
    Filed: July 25, 2013
    Publication date: February 27, 2014
  • Publication number: 20140058086
    Abstract: Methods and systems are provided for converting methane in a feed stream to acetylene. The method includes removing at least a portion of carbon dioxide from a hydrocarbon stream. The hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream may be treated to convert acetylene to another hydrocarbon process. The method according to certain aspects includes controlling the level of carbon dioxide in the hydrocarbon stream by contacting a stream with a physical or a chemical solvent.
    Type: Application
    Filed: July 17, 2013
    Publication date: February 27, 2014
  • Publication number: 20140058090
    Abstract: Methods and systems are provided for converting methane in a feed stream to acetylene. The method includes removing at least a portion of glycols from a hydrocarbon stream. The hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream may be treated to convert acetylene to another hydrocarbon process. The method according to certain aspects includes controlling the level of glycols and in particular, dimethyl ethers of polyethylene glycol in the hydrocarbon stream.
    Type: Application
    Filed: July 25, 2013
    Publication date: February 27, 2014
  • Publication number: 20140058092
    Abstract: Methods and systems are provided for converting methane in a feed stream to acetylene. The method includes removing at least a portion of carbon monoxide from a hydrocarbon stream. The hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream may be treated to convert acetylene to another hydrocarbon process. The method according to certain aspects includes controlling the level of carbon monoxide in the hydrocarbon stream.
    Type: Application
    Filed: July 25, 2013
    Publication date: February 27, 2014
  • Publication number: 20140058085
    Abstract: Methods and systems are provided for converting methane in a feed stream to acetylene. The method includes removing at least a portion of water from a hydrocarbon stream. The hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream may be treated to convert acetylene to another hydrocarbon process. The method according to certain aspects includes controlling the level of water in the hydrocarbon stream.
    Type: Application
    Filed: July 16, 2013
    Publication date: February 27, 2014
  • Publication number: 20140058088
    Abstract: Methods and systems are provided for converting methane in a feed stream to acetylene. The method includes removing at least a portion of hydrides of arsenic, phosphorus, antimony, silicon, and boron from a hydrocarbon stream. The hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream may be treated to convert acetylene to another hydrocarbon process. The method according to certain aspects includes controlling the level of hydrides of arsenic, phosphorus, antimony, silicon, and boron in the hydrocarbon stream.
    Type: Application
    Filed: July 25, 2013
    Publication date: February 27, 2014
  • Publication number: 20140058087
    Abstract: Methods and systems are provided for converting methane in a feed stream to acetylene. The method includes removing at least a portion of carbon dioxide from a hydrocarbon stream. The hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream may be treated to convert acetylene to another hydrocarbon process. The method according to certain aspects includes controlling the level of oxygen in the hydrocarbon stream.
    Type: Application
    Filed: July 17, 2013
    Publication date: February 27, 2014
  • Publication number: 20140058091
    Abstract: Methods and systems are provided for converting methane in a feed stream to acetylene. The method includes removing at least a portion of mercury containing compounds from a hydrocarbon stream. The hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream may be treated to convert acetylene to another hydrocarbon process. The method according to certain aspects includes controlling the level of organic, ionic or suspended mercury compounds by first converting these compounds to elemental mercury or to inorganic mercury compounds and then removing them by use of an adsorbent bed.
    Type: Application
    Filed: July 25, 2013
    Publication date: February 27, 2014
  • Publication number: 20130122560
    Abstract: The present invention is directed to novel methods for production of 5-epi-?-vetivone, 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one and 2-isopropyl-6,10-dimethylspiro[4.5]deca-1,6-dien-8-one, which are useful for their fragrant qualities. Provided are methods for production of premnaspirodiene from a terpene substrate, methods for production of 5-epi-?-vetivone from premnaspirodiene as starting material, and methods for production of 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one from premnaspirodiene as starting material.
    Type: Application
    Filed: December 13, 2012
    Publication date: May 16, 2013
    Inventors: Bryan N. Julien, David M. Wallace
  • Patent number: 8212082
    Abstract: The present invention relates to a process for preparing at least one compound with Z?1 cycles and 7 to 16 carbon atoms with at least one aldehyde group, at least comprising the stages: (a1) oxidation of a composition (A), at least comprising a cyclic olefin with Z cycles and 7 to 16 carbon atoms and at least two C—C double bonds, by means of dinitrogen monoxide to give a composition (A1), (a2) separating off the at least one cyclic olefin with Z cycles and 7 to 16 carbon atoms with at least two C—C double bonds from the composition (A1) from stage (a1) in order to obtain a composition (A2), (b1) separating off the at least one cyclic compound with Z cycles and 7 to 16 carbon atoms with a keto group from the composition (A2) from step (a2), in order to obtain a composition (B1), comprising at least 50% by weight of the at least one compound with Z?1 cycles and 7 to 16 carbon atoms with at least one aldehyde group and at least two C—C double bonds, where Z may be 1, 2, 3 or 4.
    Type: Grant
    Filed: January 27, 2010
    Date of Patent: July 3, 2012
    Assignee: BASF SE
    Inventors: Joaquim Henrique Teles, Beatrice Röβler-Feigel, Alexander Hauk, Christian Müller, Michael Schelper, Tanja Kirchner, Susanne Szeschkus
  • Publication number: 20120157719
    Abstract: The invention relates to a tube bundle reactor with a flat feed hood. Alternatively, the release hood may also have a flat design. The flat design reduces the heat of reaction which arises in the hood in the case of reaction types which take place not only in the tube bundle (uncatalyzed reactions and reactions with homogeneously distributed catalyst). This greatly suppresses undesired reactions which already take place in the hood owing to accumulated heat, which achieves a higher selectivity in the case of thermally sensitive reactions. In addition, the thermal distribution within the hoods can be controlled precisely. The tube bundle reactor comprises a tube bundle which has a feed end which is connected to a feed hood of the tube bundle reactor, wherein the feed hood is configured in a flat design with a cross-sectional area at the feed end and an internal volume, and the ratio of internal volume to cross-sectional area is less than 0.35 m.
    Type: Application
    Filed: January 19, 2010
    Publication date: June 21, 2012
    Applicant: BASF SE
    Inventors: Joaquim Henrique Teles, Peter Resch, Wilhelm Ruppel, Ulrike Wegerle, Wolfgang Gerliing, Beatrice Rössler-Feigel, Anton Meier, Christian Müller
  • Patent number: 8188320
    Abstract: The present invention relates to a process for preparing at least one cyclic compound with Z cycles and 7 to 16 carbon atoms with a keto group, at least comprising the stages: (a1) oxidation of a composition (A), at least comprising one cyclic olefin with Z cycles and 7 to 16 carbon atoms and at least two C—C double bonds, by means of dinitrogen monoxide to give a composition (A1), (a2) separating off the at least one cyclic olefin with Z cycles and 7 to 16 carbon atoms with at least two C—C double bonds from the composition (A1) in order to obtain a composition (A2), and (b) distillative treatment of the composition (A2) from step (a2) in order to obtain a composition (B), comprising the at least one cyclic compound with Z cycles and 7 to 16 carbon atoms with a keto group and less than 1.0% by weight of the at least one compound with Z?1 cycles and 7 to 16 carbon atoms with at least one aldehyde group, where Z can be 1, 2, 3 or 4.
    Type: Grant
    Filed: January 27, 2010
    Date of Patent: May 29, 2012
    Assignee: BASF SE
    Inventors: Joaquim Henrique Teles, Beatrice Röβler-Feigel, Alexander Hauk, Anton Meier, Christian Müller, Michael Schelper, Tanja Kirchner, Susanne Szeschkus, Rolf Pinkos, Gerd-Dieter Tebben
  • Publication number: 20110288341
    Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are fed to at least one reaction zone comprising a catalyst system which comprises a molecular sieve and at least one hydrogenation metal. The MCM-22 family molecular sieve having an X-ray diffraction pattern including d-spacing maxima at 12.4±0.25, 6.9±0.15, 3.57±0.07 and 3.42±0.07 Angstrom, and the hydrogenation metal is selected from the group consisting of palladium, ruthenium, nickel, zinc, tin, cobalt, and combinations of any two or more thereof Hydroalkylation conditions of temperature and pressure are selected to produce a hydroalkylation conversion in a range of from about 15% to about 75% The benzene and hydrogen are then contacted in the at least one reaction zone under said selected hydroalkylation condition to produce an effluent containing cyclohexylbenzene.
    Type: Application
    Filed: November 24, 2009
    Publication date: November 24, 2011
    Inventors: Tan-Jen Chen, Francisco M. Benitez, John S. Buchanan, Jane C. Cheng, Jon E. Stanat
  • Patent number: 7939692
    Abstract: There are disclosed a method for producing a ketone compound, which comprises reacting an olefin compound with molecular oxygen and water in the presence of an effective amount of proton and a catalyst containing i) a chlorine-free palladium source, ii) a heteropoly acid or an acid salt of a heteropoly acid, and iii) a mesoporous silicate, and catalysts for the process.
    Type: Grant
    Filed: January 3, 2007
    Date of Patent: May 10, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Roger Gläser, Sudhir Dapurkar, Carsten Stöcker, Junichi Nishimoto, Masayoshi Murakami
  • Patent number: 7803971
    Abstract: A process for preparing cyclopentanone, at least comprising the following steps (i) to (iii): (i) providing a mixture G(i) comprising cyclopentene; (ii) providing liquid or supercritical N2O or a liquid or supercritical gas mixture G(ii) comprising at least 20% by volume of N2O, based on the total volume of the mixture G(ii); (iii) contacting the mixture G(i) with the liquid or supercritical N2O or the liquid or supercritical mixture G(ii) to obtain a mixture G(iii) comprising cyclopentanone, wherein the mixture G(i) contains at least 25% by weight and at most 95% by weight, of cyclopentene, based on the total weight of the mixture G(i).
    Type: Grant
    Filed: September 23, 2005
    Date of Patent: September 28, 2010
    Assignee: BASF Akiengesellschaft
    Inventors: Joaquim Henrique Teles, Beatrice Röβler, Thomas Genger, Andreas Glass
  • Patent number: 7790930
    Abstract: The present invention relates to a process for purifying a composition (I) comprising at least one cyclic ketone having from 7 to 16 carbon atoms, which comprises thermal treatment of the composition (I) with a catalyst comprising at least one transition metal and further purification by means of a process selected from the group consisting of distillation, extraction and crystallization. Furthermore, the present invention relates to a process for preparing cyclododecanone, which comprises such a purification, and the use of at least one catalyst comprising at least one transition metal for purifying a composition (I) comprising at least one cyclic ketone having from 7 to 16 carbon atoms by thermal treatment of the composition (I) with a catalyst comprising at least one transition metal.
    Type: Grant
    Filed: June 27, 2007
    Date of Patent: September 7, 2010
    Assignee: BASF SE
    Inventors: Rolf Pinkos, Gerd Tebben, Christian Müller, Harald Rust
  • Patent number: 7714172
    Abstract: The present invention relates to a process for preparing a cyclic ketone having from 7 to 16 carbon atoms, which comprises at least the steps (a) oxidation of a composition (I) comprising at least one cyclic alkene which has from 7 to 16 carbon atoms and at least one C—C double bond by means of dinitrogen monoxide to give a composition (A), (b) treatment of the composition (A) with at least one base to give a composition (B), (c) hydrogenation of the composition (B) in the presence of at least one catalyst to give a composition (C), (d) purification of the composition (C), comprising at least the steps (di) thermal treatment of the composition (C) with at least one acid or at least one catalyst comprising at least one transition metal, (dii) further purification by a method selected from the group consisting of distillation, extraction and crystallization.
    Type: Grant
    Filed: June 27, 2007
    Date of Patent: May 11, 2010
    Assignee: BASF SE
    Inventors: Joaquim Henrique Teles, Beatrice Röβler, Rolf Pinkos, Gerd Tebben, Christian Müller, Harald Rust
  • Patent number: 7714171
    Abstract: The present invention relates to a process for purifying a composition (I) comprising at least one cyclic ketone having from 7 to 16 carbon atoms, which comprises thermal treatment of the composition (I) with at least one acid and further purification by means of a process selected from the group consisting of distillation, extraction and crystallization, Furthermore, the present invention relates to a process for preparing cyclododecanone, which comprises such a purification, and the use of at least one acid for purifying a composition (I) comprising at least one cyclic ketone having from 7 to 16 carbon atoms by thermal treatment of the composition (I) with the acid.
    Type: Grant
    Filed: June 27, 2007
    Date of Patent: May 11, 2010
    Assignee: BASF SE
    Inventors: Rolf Pinkos, Gerd Tebben, Alexander Hauk, Christian Müller, Harald Rust
  • Publication number: 20090326276
    Abstract: The present invention relates to a process for preparing a cyclic ketone having from 7 to 16 carbon atoms, which comprises at least the steps (a) oxidation of a composition (I) comprising at least one cyclic alkene which has from 7 to 16 carbon atoms and at least one C—C double bond by means of dinitrogen monoxide to give a composition (A), (b) treatment of the composition (A) with at least one base to give a composition (B), (c) hydrogenation of the composition (B) in the presence of at least one catalyst to give a composition (C), (d) purification of the composition (C), comprising at least the steps (di) thermal treatment of the composition (C) with at least one acid or at least one catalyst comprising at least one transition metal, (dii) further purification by a method selected from the group consisting of distillation, extraction and crystallization.
    Type: Application
    Filed: June 27, 2007
    Publication date: December 31, 2009
    Applicant: BASF SE
    Inventors: Joaquim Henrique Teles, Beatrice Rößler, Rolf Pinkos, Gerd Tebben, Christian Müller, Harald Rust
  • Publication number: 20090306433
    Abstract: A process for producing phenol and methyl ethyl ketone comprises contacting benzene and a C4 olefin under alkylation conditions and in the presence of an alkylation catalyst to produce an alkylation effluent comprising sec-butylbenzene and C8+ olefins. The alkylation effluent is then treated to reduce the amount of said C8+ olefins and produce a treated effluent, whereafter the sec-butylbenzene in the treated effluent is oxidized to produce a hydroperoxide and the hydroperoxide is cleaved to produce phenol and methyl ethyl ketone.
    Type: Application
    Filed: February 8, 2007
    Publication date: December 10, 2009
    Inventors: Jihad M. Dakka, Edmund J. Mozeleski, Jane C. Cheng, Francisco M. Benitez, Jon E. Stanat, John S. Buchanan
  • Patent number: 7449606
    Abstract: A process for preparing a ketone, in particular cyclododecanone, by reacting cyclododecatriene with dinitrogen monoxide to obtain cyclododecadienone and hydrogenating the resulting cyclododecadienone, in particular to give cyclododecanone.
    Type: Grant
    Filed: September 23, 2004
    Date of Patent: November 11, 2008
    Assignee: BASF SE
    Inventors: Joaquim Henrique Teles, Beatrice Röβler, Rolf Pinkos, Thomas Genger, Thomas Preiss
  • Patent number: 7214832
    Abstract: The present invention provides a process for the preparation of a bicyclic aminoalcohol which comprises reacting a starting compound, nopinone (I), with XCH2COOR1 wherein X is halogen, and R1 is alkyl, in the presence of an additive and a base to produce a compound (II), converting it to oxime derivative (III), and reducing it with an aluminum hydride
    Type: Grant
    Filed: February 25, 2004
    Date of Patent: May 8, 2007
    Assignee: Shionogi & Co., Ltd.
    Inventors: Tsunetoshi Honma, Yoshiharu Hiramatsu, Susumu Mitsumori
  • Patent number: 6982354
    Abstract: A method of preparing a polycyclic compound containing a ketone functionality comprising: reacting a mixture comprising a catalyst, a reactant compound and an amount of water greater than or equal to 3 weight percent (wt %) based on the weight of the reactant compound; wherein said catalyst comprises nickel and base and said reactant compound comprises at least two fused rings, A and B wherein ring A is a saturated ring or ring system having 5 to 7 cyclic carbons and substituted with a hydroxyl functionality and ring B is a non-aromatic unsaturated ring having 5 to 6 cyclic carbons; and converting the hydroxyl functionality of ring A to a ketone functionality and non-aromatic unsaturated ring B to a saturated ring.
    Type: Grant
    Filed: February 2, 2004
    Date of Patent: January 3, 2006
    Assignee: General Electric Company
    Inventors: Jegadeesh Thampi, Umesh Krishna Hasyagar, Anju S. Shukla, Pramod Kumbhar
  • Patent number: 6914109
    Abstract: The invention relates to a process for the preparation of 15-pentadecanolide by hydrogenating 15-pentadecenolide and to its use.
    Type: Grant
    Filed: March 18, 2002
    Date of Patent: July 5, 2005
    Assignee: Symrise GmbH & Co. KG
    Inventors: Walter Kuhn, Oskar Koch, Hans-Ulrich Funk, Gerhard Senft
  • Patent number: 6884913
    Abstract: A process for the manufacture of an alpha, beta-unsaturated cyclic ketone, such as carvone, comprises the dehydrogenation of a secondary allylic cyclic alcohol, such as carveol, in the presence of at least one metal carboxylate. The process can be performed in a batchwise or continuous mode. Examples of suitable metal carboxylates include magnesium stearate, calcium 2-ethylhexanoate, and zinc 2-ethylhexanoate.
    Type: Grant
    Filed: May 30, 2003
    Date of Patent: April 26, 2005
    Assignee: Millennium Specialty Chemicals
    Inventors: Gennadiy G. Kolomeyer, Jacob S. Oyloe
  • Patent number: 6815413
    Abstract: Lower alkyl- and lower alkylidene-substituted, saturated or unsaturated cyclohexadecanones are grand fragrances with muscone note with which perfumes with new odor notes can be prepared.
    Type: Grant
    Filed: August 2, 2001
    Date of Patent: November 9, 2004
    Assignee: Symrise GmbH & Co. KG
    Inventors: Marcus Eh, Ingo Wöhrle
  • Patent number: 6806389
    Abstract: The invention relates to the use of an immobilized transition metal carbonyl complex as a catalyst in the Pauson-Khand reaction and to processes using such as catalyst.
    Type: Grant
    Filed: April 19, 2002
    Date of Patent: October 19, 2004
    Assignee: AstraZeneca AB
    Inventors: Alex Christian Comely, Sue Elizabeth Gibson, Neil James Hales
  • Patent number: 6770618
    Abstract: Trans-2,2,6-trimethylcyclohexyl methyl ketone, including (1S,6R)-2,2,6-trimethylcyclohexyl methyl ketone represented by the formula (1a): and (1R,6S)-2,2,6-trimethylcyclohexyl methyl ketone represented by the formula (1b): are useful components in a perfume composition. A process for producing the same is also described. A unique eucalyptus, mint-like and white floral perfume material is provided using the ketone compounds disclosed in the present invention. The process of the present invention produces the optically active ketone compounds having optical purity up to at least 98.0 % e.e.
    Type: Grant
    Filed: June 7, 2001
    Date of Patent: August 3, 2004
    Assignee: Takasago International Corp.
    Inventors: Hideo Ujihara, Shinya Watanabe, Takeshi Yamamoto, Toshimitsu Hagiwara
  • Publication number: 20030220525
    Abstract: Disclosed are processes for conversion of (3R,3′R,6′R)-lutein to (3R,6′R)-&agr;-cryptoxanthin, (3R)-&bgr;-cryptoxanthin, anhydroluteins I, II, and III (dehydration products of lutein), and a method for separating and purifying the individual carotenoids including the unreacted (3R,3′R)-zeaxanthin. The invention also includes two methods that transform (3R,3′R,6′R)-lutein into (3R,6′R)-&agr;-cryptoxanthin in excellent yields.
    Type: Application
    Filed: January 24, 2003
    Publication date: November 27, 2003
    Inventor: Frederick Khachik
  • Patent number: 6632787
    Abstract: Carbonyl compounds derived from the reaction of alkyl cyclopentenols and vinyl ethers are described. The carbonyl compounds described have excellent fragrance properties, and their use as fragrances and/or fragrance-enhancing compounds is also described. Processes for the preparation of the carbonyl compounds are described as well.
    Type: Grant
    Filed: August 10, 2001
    Date of Patent: October 14, 2003
    Assignee: Cognis Deutschland GmbH & Co. KG
    Inventors: Thomas Markert, Ute Lemke, Elke Veit, Theo Ten Pierik, Ralph Nemitz, Volker Porrmann, Marc Speitkamp
  • Patent number: 6215028
    Abstract: The invention relates to a process for the preparation of cyclohexanones from the corresponding phenols by partial hydrogenation, characterized in that the reaction mixture obtained by means of the hydrogenation is treated with sulfonating agents before the isolation of the cyclohexanone.
    Type: Grant
    Filed: November 2, 1998
    Date of Patent: April 10, 2001
    Assignee: Merck Patent Gesellschaft mit
    Inventors: Bernd Oster, Peter Mackert, Detlef Pauluth, Markus Wydra
  • Patent number: 6127580
    Abstract: Process for the preparation of anthraquinones of the general formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4, which can be identical or different, are hydrogen, a C.sub.1 -C.sub.8 -alkyl or C.sub.2 -C.sub.8 -alkenyl radical, in which 1,4-naphthoquinone is reacted with a 1,3-diene of the general formula II ##STR2## in a cycloaddition step to give the corresponding tetrahydroanthraquinone and the tetrahydroanthraquinone is oxidized with oxygen in the presence of a basic catalyst to give the anthraquinone, in which both the cycloaddition step and the oxidation step are carried out in the presence of an aqueous diluent.Preferably, the cycloaddition step and oxidation step are carried out at a reaction temperature between 90 and 110.degree. C. and at atmospheric pressure.
    Type: Grant
    Filed: November 30, 1998
    Date of Patent: October 3, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Siegel, Andreas Kramer
  • Patent number: 5268492
    Abstract: An optically active diphosphine having a bicyclo[2.2.1]heptane of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are difined in the specification and a metal complex comprising said optically active diphosphine are disclosed. A process for producing or purifying said optically active diphosphine is disclosed.
    Type: Grant
    Filed: August 27, 1992
    Date of Patent: December 7, 1993
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Keiji Yamamoto, Masahiro Miyazawa, Satoru Momose
  • Patent number: 5258547
    Abstract: A process for preparing halogenated compounds of formula RCY(Z)CH.sub.2 CH(X)C(CH.sub.3)CH.sub.2 COR.sup.1 where X, Y and Z are halo, R is alkyl, halo, haloalkyl or aryl, and R.sup.1 is hydroxy, halo, alkoxy, alkyl or haloalkyl, or the residue of a pyrethroidal alcohol, in which a compound of formula CH.sub.2 =CHC(CH.sub.3).sub.2 COR.sup.1 is reacted with a sulphonyl halide of formula RCY(Z)SO.sub.2 X. The process avoids the use of volatile halocarbons in the production of valuable intermediates for insecticides.
    Type: Grant
    Filed: January 9, 1992
    Date of Patent: November 2, 1993
    Assignee: Imperial Chemical Industries plc
    Inventor: Gary N. Sheldrake
  • 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: 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: 4585897
    Abstract: A process for hydration and condensation of acetylene in a crude acetylene stream containing water in the presence of a zirconia-alumina catalyst containing water to prepare aliphatic, aromatic and oxygenated compounds suitable for use as high octane liquid water fuels and as octane improvers for motor fuels is disclosed.
    Type: Grant
    Filed: August 24, 1984
    Date of Patent: April 29, 1986
    Assignee: Standard Oil Company (Indiana)
    Inventors: Ellis K. Fields, Mark L. Winzenburg, David A. De Marco
  • 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: 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: 4529813
    Abstract: Insecticidally active vinyl-cyclopropane carboxylic acid esters of the formula ##STR1## are prepared by reacting ##STR2## in which R.sup.12 is a radical selected from the group consisting of ##STR3## with an alcoholate of the formulaM--O--R.sup.8.Various processes for making the intermediates are also described. Many of the intermediates and end products are new.
    Type: Grant
    Filed: March 14, 1980
    Date of Patent: July 16, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Georg Heine, Willy Hartmann
  • 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: 4518797
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO,--C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: May 21, 1985
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4483996
    Abstract: A process for converting a desired olefin to the corresponding olefin oxide, such as propylene oxide, and/or ketone comprising reacting a mixture of the olefin, thallic oxide, carbon dioxide and water in a substantially organic solvent-free reaction zone; withdrawing a product stream from the reaction zone, the stream comprising the olefin and ketone product; separating and collecting the olefin oxide and ketone product from the stream; contacting the reduced thallous values present in the mixture with molecular oxygen and an effective catalyst to back oxidize the thallous values to their original thallic form; separating and recycling back to the reaction mixture the regenerated thallic values.
    Type: Grant
    Filed: February 22, 1983
    Date of Patent: November 20, 1984
    Assignee: The Halcon SD Group, Inc.
    Inventor: Stephen E. Jacobson
  • Patent number: 4415756
    Abstract: New bicyclo[2.2.2]oct-5-en-2-ones of the formulae Ia and Ib in the form of pure enantiomers and processes for preparing them are described. The compounds are used for the preparation of pure enantiomers of the formula V by sensitized photoreaction or of compounds of the formula VI by unsensitized photoreaction.
    Type: Grant
    Filed: December 2, 1981
    Date of Patent: November 15, 1983
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Martin Demuth, Kurt Schaffner
  • Patent number: 4304934
    Abstract: This invention relates to a method of synthesizing 3-amino-2-hydroxy-2-cyclopentenones possessing an aliphatic substituent in the 4-position which comprises reacting cyanoacetamide with an aliphatic aldehyde to yield the corresponding .beta.-substituted-.alpha.,.alpha.'-dicyanoglutaramide, hydrolyzing the amide to the corresponding .beta.
    Type: Grant
    Filed: December 30, 1980
    Date of Patent: December 8, 1981
    Assignee: Polaroid Corporation
    Inventors: James R. Bartels-Keith, Eva R. Karger, Jean B. Rogers
  • Patent number: 4219504
    Abstract: A process for the preparation of an aldehyde or a ketone by ozonolysis of an ethylenically unsaturated compound in the presence of an anti-oxidant followed by reductive cleavage of the ozonolysis product.
    Type: Grant
    Filed: February 23, 1979
    Date of Patent: August 26, 1980
    Assignee: Shell Oil Company
    Inventors: Pieter A. Verbrugge, Petrus A. Kramer
  • Patent number: 4209642
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO, --C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: June 24, 1980
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman