Olefin Reacted With The Hydroxy Containing Reactant (e.g., Preparing By Telomerization, Etc.) Patents (Class 568/904)
  • Patent number: 8987531
    Abstract: The present invention is directed to methods of synthesizing insect pheromones, particularly lepidopteran insect pheromones, their precursors and derivatives from inexpensive, readily available starting materials using olefin metathesis catalysis.
    Type: Grant
    Filed: March 5, 2013
    Date of Patent: March 24, 2015
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Myles B. Herbert, Zachary K. Wickens, Vanessa M. Marx, Benjamin K. Keitz, Koji Endo
  • Patent number: 8853471
    Abstract: Preparation of C4-oxygenates, in particular 2-butanol and butanone, which comprises the reaction of ethene with ethanol to form 2-butanol under conditions under which ethanol is present in the supercritical state.
    Type: Grant
    Filed: November 25, 2013
    Date of Patent: October 7, 2014
    Assignee: BASF SE
    Inventors: Stefan Rüdenauer, Klaus Ebel, Marta Porta Garcia
  • Publication number: 20140148619
    Abstract: Preparation of C4-oxygenates, in particular 2-butanol and butanone, which comprises the reaction of ethene with ethanol to form 2-butanol under conditions under which ethanol is present in the supercritical state.
    Type: Application
    Filed: November 25, 2013
    Publication date: May 29, 2014
    Applicant: BASF SE
    Inventors: Stefan Rüdenauer, Klaus Ebel, Marta Porta Garcia
  • Patent number: 8603201
    Abstract: The present invention is to provide a novel method for manufacturing various organic compounds from two or more kinds of alcohol, or one kind of alcohol having three or more carbon atoms. It is a method for synthesizing one kind of, or two or more kinds of organic compounds comprising allowing two or more kinds of alcohol or one kind of alcohol having three or more carbon atoms to contact a calcium phosphate catalyst such as hydroxyapatite, or hydrotalcite.
    Type: Grant
    Filed: February 23, 2009
    Date of Patent: December 10, 2013
    Assignee: Kabushiki Kaisha Sangi
    Inventors: Takashi Tsuchida, Shuji Sakuma, Tetsuya Yoshioka, Jun Kubo
  • Publication number: 20130281688
    Abstract: Unsaturated alcohol compositions are obtained by reducing a metathesis-derived hydrocarbyl unsaturated ester. Also disclosed is a process for preparing an unsaturated alcohol composition, where a metathesis derived hydrocarbyl carbonyl compound is reacted in the presence of a silane compound, an organic solvent, and a catalyst system prepared from a metallic complex and a reducing agent. This mixture is then hydrolyzed with a metallic base, and then mixed with organic solvent. The resultant mixture is then separated, washed, dried, and/or purified to produce the unsaturated alcohol composition. The unsaturated alcohol derivatives are useful in many end-use applications, including, for example, lubricants, functional fluids, fuels, functional additives for such lubricants, functional fluids and fuels, plasticizers, asphalt additives, friction reducing agents, plastics, and adhesives.
    Type: Application
    Filed: April 22, 2013
    Publication date: October 24, 2013
    Applicant: Elevance Renewable Sciences, Inc
    Inventors: Stephen A. Di Biase, Keith M. Wampler, David R. Allen, Randal J. Bernhardt, Ryan Littich
  • Publication number: 20130231499
    Abstract: The present invention is directed to methods of synthesizing insect pheromones, particularly lepidopteran insect pheromones, their precursors and derivatives from inexpensive, readily available starting materials using olefin metathesis catalysis.
    Type: Application
    Filed: March 5, 2013
    Publication date: September 5, 2013
    Inventors: ROBERT H. GRUBBS, MYLES B. HERBERT, ZACHARY K. WICKENS, VANESSA M. MARX
  • Publication number: 20130190518
    Abstract: The present invention relates to a process for preparing a terpenoid derivative, the process comprising a metathesis of an olefin and a terpenoid, and to terpenoid derivatives prepared with said process.
    Type: Application
    Filed: July 11, 2011
    Publication date: July 25, 2013
    Applicant: Ecole Nationale Superieure de Chimie de Rennes
    Inventors: Marc Mauduit, Frédéric Caijo, Christophe Crévisy
  • Patent number: 8455698
    Abstract: The invention relates to a method for producing a mixture containing hydroxy- and aldehyde functional compounds by a cross-metathesis reaction of at least one at least monounsaturated fatty acid or at least one at least monounsaturated fatty acid derivative with an olefinic compound having at least one hydroxy group and at least one C—C double bond, in the presence of a metathesis catalyst at a maximum temperature of 180° C.
    Type: Grant
    Filed: December 30, 2009
    Date of Patent: June 4, 2013
    Assignee: Evonik Degussa GmbH
    Inventors: Michael A. R. Meier, Anastasiya Rybak, Dominik Geisker
  • Patent number: 8394996
    Abstract: The invention relates to a method for producing aldehyde functional compounds by a cross-metathesis reaction of an olefinic compound having at least one hydroxy group and at least one C—C double bond with at least one at least monounsaturated fatty acid or at least one at least monounsaturated fatty acid derivative, in the presence of a metathesis catalyst at a maximum temperature of 180° C. and in the presence of at least one reagent that acts as a protective group-forming compound in relation to the aldehyde group of the aldehyde functional compounds.
    Type: Grant
    Filed: January 12, 2010
    Date of Patent: March 12, 2013
    Assignee: Evonik Degussa GmbH
    Inventors: Michael A. R. Meier, Anastasiya Rybak, Dominik Geisker, Peter Hannen, Martin Roos
  • Publication number: 20100048960
    Abstract: A process for preparing alkanols (I) selected from the group consisting of isopropanol and 2-butanol from the corresponding alkanes (II) selected from the group consisting of propane and n-butane, comprising the steps of: A) providing a starting gas stream a comprising the alkane (II); B) feeding the starting gas stream a comprising the alkane (II) into a dehydrogenation zone and subjecting the alkane (II) to a dehydrogenation to the alkene (III) to obtain a product gas stream b comprising the alkene (III) and unconverted alkane (II), with or without high boilers, steam, hydrogen and low boilers; C) at least compressing product gas stream b, optionally separating product gas stream b into an aqueous phase c1, a phase c2 comprising the alkene (III) and the alkane (II), with or without high boilers, and a gas phase c3 comprising hydrogen and low boilers; D) reacting product gas stream b or the phase c2 comprising alkene (III) and alkane (II) with an organic acid (IV) in an esterification zone to obtain a produ
    Type: Application
    Filed: July 16, 2007
    Publication date: February 25, 2010
    Applicant: BASF Aktiengesellschaft
    Inventors: Georg Degen, Sven Crone, Ralf Boehling, Ansgar Gereon Altenhoff, Wolfgang Rohde, Jochen Buerkle, Goetz-Peter Schindler, Thomas Holtmann, Markus Schmitt
  • Patent number: 7601880
    Abstract: The present invention relates to a method for catalytic deoxygenation of process fluids of olefin dimerization processes. According to the invention at least one process fluid containing oxygenates is brought into contact with a deoxygenation catalyst at, at least one location in a column or connected to a column. The present invention relates also to a process for dimerization of olefins, wherein at least part of olefin feed is dimerized in at least one dimerization reaction zone to produce a first product stream comprising oxygenates, and separating in a distillation zone, comprising one or more distillation columns, the first product stream into a second product stream and a third product stream and at, at least one location of the distillation column or a vessel connected to the distillation column is located a deoxygenation catalyst for decomposing oxygenates.
    Type: Grant
    Filed: September 17, 2004
    Date of Patent: October 13, 2009
    Assignee: Neste Oil Oyj
    Inventor: Antti Pyhälahti
  • Publication number: 20020091281
    Abstract: The present invention is related to a process for telomerizing a conjugated diene which comprises reacting said conjugated diene with a compound containing active hydrogen in the presence of a catalyst system comprising at least one transition metal compound, at least one phosphorus-containing compound, and at least one salt which forms a liquid under the conditions of the telomerization process.
    Type: Application
    Filed: October 22, 2001
    Publication date: July 11, 2002
    Applicant: Celanese Chemicals Europe GmbH
    Inventors: Yves Chauvin, Lionel Magna, Gerald Peter Niccolai, Jean-Marie Basset
  • Patent number: 6392105
    Abstract: The invention provide a method for producing a fluoroalcohol of the following formula (1): H(CFR1CF2)nCH2OH  (1) (wherein R1 represents F or CF3, when n=1; R1 represents F, when n=2) comprising reacting methanol with tetrafluoroethylene or hexafluoropropylene in the presence of a free radical source, wherein the reaction mixture is subjected to distillation either in the presence of a base or after contact of said reaction mixture with a base.
    Type: Grant
    Filed: September 1, 1999
    Date of Patent: May 21, 2002
    Assignee: Daikin Industries, Ltd.
    Inventors: Toru Yoshizawa, Shoji Takaki, Takashi Yasuhara, Yasunori Yokoyama
  • Patent number: 6329555
    Abstract: Described is a process for preparing substituted butenes of the formula I and/or II, where the radical R is unsubstituted or mono- or di-C1-C10-alkoxy-substituted or mono- or dihydroxy-substituted C2-C20-alkyl or alkenyl or is C6-C10-aryl, C7-C11-aralkyl or methyl by reacting 1,3-butadiene with an alcohol of the formula ROH in which R is as defined in the presence of an acidic particulate catalyst insoluble in the reaction medium, which involves contacting the butadiene, the alcohol and the catalyst in a fluidized bed reactor which is flow-approached from below and is operated at above the loosening point.
    Type: Grant
    Filed: November 2, 1999
    Date of Patent: December 11, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Maik Aron, Ralf Böhling, Peter Zehner
  • Patent number: 6294704
    Abstract: The invention relates to a method for manufacturing a fluoroalcohol represented by formula (1) H(CFR1CF2)nCH2OH  (1) (wherein R1 represents F or CF3, when n=1; R1 represents F, when n=2) by reacting methanol with tetrafluoroethylene or hexafluoropropylene in the presence of a free radical generator, wherein the method comprises the steps of: feeding a reaction mixture into a distillation column; distilling off methanol from the top of the distillation column; withdrawing a bottom fraction comprising the fluoroalcohol from the bottom of the distillation column; removing a fraction comprising water and HF from the distillation column by side cut; feeding methanol from the top of the distillation column back into a reactor for recycling; and purifying the bottom fraction to recover the fluoroalcohol represented by formula (1).
    Type: Grant
    Filed: September 13, 1999
    Date of Patent: September 25, 2001
    Assignee: Daikin Industries, Ltd.
    Inventors: Shoji Takaki, Toru Yoshizawa
  • Patent number: 6187969
    Abstract: A process for producing a fluoroalcohol of the following formula (1) H(CFR1CF2)nCH2OH  (1) (n=1 or 2, wherein R1 represents F or CF3 when n=1; R1 represents F when n=2) comprising reacting methanol with tetrafluoroethylene or hexafluoropropylene in the presence of an initiator wherein the fluoroalcohol of formula (1) is distilled after decomposing the remaining initiator contained in the reaction mixture.
    Type: Grant
    Filed: September 13, 1999
    Date of Patent: February 13, 2001
    Assignee: Daikin Industries, Ltd.
    Inventors: Fumihiko Yamaguchi, Shoji Takaki, Toru Yoshizawa, Eiji Ogura, Toshiyuki Katsube
  • Patent number: 6166265
    Abstract: Process for the preparation of n-butyraldehyde and/or n-butanol, whereina) 1,3-Butadiene or a butadiene-containing hydrocarbon mixture is reacted with an alcohol of the formula IROH I,where R is C.sub.2 -C.sub.20 -alkyl or alkenyl which is unsubstituted or substituted by 1 or 2 C.sub.1 -C.sub.10 -alkoxy or hydroxyl groups, or is C.sub.6 -C.sub.10 -aryl, C.sub.7 -C.sub.
    Type: Grant
    Filed: September 15, 1999
    Date of Patent: December 26, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Jurgen Kanand, Rocco Paciello, Michael Roper
  • Patent number: 6111149
    Abstract: Alcohols and/or aldehydes are prepared from olefins by cross-metathesis of olefins with alcohols having at least one double bond in the molecule and in which at least one hydroxyl is in the allyl position relative to a C.dbd.C double bond over catalysts of the formula (I)XX.sup.1 LL.sup.1 Ru [sic].dbd.CR.sup.1 R.sup.2 (I)with optional subsequent hydrogenation and/or isomerization, R.sup.1 and R.sup.2 being hydrogen or C-organic radicals with or without a heteroatom, X [sic] and X.sup.1 [sic] being, independently, anionic ligands, and L [sic] and L.sup.1 [sic] being, independently, neutral electron donor ligands.
    Type: Grant
    Filed: January 7, 1999
    Date of Patent: August 29, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Schwab, Arthur Hohn, Rocco Paciello
  • Patent number: 5892125
    Abstract: A process for the preparation of n-butyraldehyde and/or n-butanol, in whicha) 1,3-butadiene is caused to react with an amine of the formula IR.sup.1 R.sup.2 NH, Iin which R.sup.1 and R.sup.
    Type: Grant
    Filed: July 23, 1997
    Date of Patent: April 6, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Jurgen Kanand, Michael Roper, Rocco Paciello, Alfred Thome
  • Patent number: 5856592
    Abstract: A continuous vapor phase processes for direct condensation of methanol and/or dimethyl ether with dilute acetylene feedstream to a mixture containing at least one higher molecular weight alkanol, such as n-propanol or isobutanol, over an alkaline catalyst which is, advantageously, an essentially magnesium oxide catalyst.
    Type: Grant
    Filed: April 7, 1997
    Date of Patent: January 5, 1999
    Assignee: Amoco Corporation
    Inventor: Gary P. Hagen
  • Patent number: 5831134
    Abstract: A process is disclosed for producing tertiary alcohols by radical addition of secondary alcohols to alkenes. The reaction is carried out as a continuous process in the presence of an organic peroxide as a radical initiator and during a mean contact time of the reaction mixture of up to a maximum of 1 hour.
    Type: Grant
    Filed: October 25, 1996
    Date of Patent: November 3, 1998
    Assignee: Peroxid-Chemie GmbH
    Inventors: Michael Gnann, Maria Eckert, Robert Rieth, deceased, Werner Eberhard Wilhelm Rieth, heir, Emma Marianne Christine Rieth, heir
  • Patent number: 5705707
    Abstract: A process for the preparation of n-butyraldehyde and/or n-butanol, whereina) 1,3-butadiene is caused to react with an alcohol of the formula IROH I,to form a mixture of adducts of the formulas II ##STR1## and III ##STR2## b) the adduct III is isomerized to the adduct II, c) the adduct II is isomerized in the presence of a homogeneous or heterogeneous transition metal element catalyst to form the enol ether of the formula IV ##STR3## and d) n-butyraldehyde and/or n-butanol is/are produced from this ether IV by the reaction thereof with hydrogen and water or water only in the presence of a homogeneous or heterogeneous catalyst.
    Type: Grant
    Filed: July 12, 1996
    Date of Patent: January 6, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Jurgen Kanand, Michael Roper, Rolf Pinkos, Rocco Paciello, Alfred Thome
  • Patent number: 5159125
    Abstract: A catalyzed, continuous vapor phase process to convert a C.sub.2 or higher olefin in combination with methanol to a mixture containing at least one higher molecular weight alcohol, for example, isobutanol, over a magnesium oxide composition. The process also may contain a lower aldehyde and/or ketone in the feed.
    Type: Grant
    Filed: December 23, 1991
    Date of Patent: October 27, 1992
    Assignee: Amoco Corporation
    Inventor: Gary P. Hagen
  • Patent number: 5012018
    Abstract: A polyprenyl composition consisting essentially of a mixture of polyprenyl compounds represented by the following formula ##STR1## wherein A.sub.1 represents a hydroxyl or acetyloxy group, ##STR2## represents a trans-isoprene unit ##STR3## represents a cis-isoprene unit, and n is an integer of from 11 to 19, said mixture containing substantial amounts of at least three compounds of formula (I) wherein n represents 14, 15 and 16 respectively as essential ingredients in a total amount of at least 70% by weight based on the weight of the mixture; and new compounds derived from the polyprenyl compounds of formula (I). These composition and compounds are useful for the synthesis of mammalian dolichols.
    Type: Grant
    Filed: September 25, 1984
    Date of Patent: April 30, 1991
    Assignee: Kuraray Co., Ltd.
    Inventors: Yasuyuki Tanaka, Koichi Ibata, Masao Mizuno, Yoichi Ninagawa, Takashi Nishida
  • Patent number: 4720558
    Abstract: Process for inverting the configuration of secondary alcohols in which the hydroxyl group is attached to an asymmetric carbon atom, in accordance with which the secondary alcohols are esterified, with inversion of their configuration, by conversion into isourea ethers and reaction of these isourea ethers with carboxylic acids, and the esters are then saponified with retention of the configuration of the secondary alcohols.
    Type: Grant
    Filed: March 11, 1986
    Date of Patent: January 19, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventor: Johannes Kaulen
  • Patent number: 4399301
    Abstract: Methylenically-substituted undecadiene compounds having the structural formula: ##STR1## wherein X is selected from the group consisting of lower acyloxy, aryloxy having from 6 to 14 carbon atoms, lower alkoxy and hydroxy, and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15 and R.sub.16 are independently selected from the group consisting of hydrogen and lower alkyl, with the proviso that at least one of R.sub.3, R.sub.5 and R.sub.6 and at least one of R.sub.9, R.sub.10, R.sub.11 and R.sub.12 must be hydrogen, are prepared by reacting a diene having the structural formula: ##STR2## with a conjugated diene having the structural formula: ##STR3## in the presence of a rhodium/trivalent phosphorus catalyst, with the atomic ratio of the trivalent phosphorus to the rhodium therein being at least 1.5. The compounds can be hydrogenated and saponified to form known alcohols which are precursors for biodegradable detergents.
    Type: Grant
    Filed: September 13, 1979
    Date of Patent: August 16, 1983
    Assignee: Rhone-Poulenc Industries
    Inventor: Didier Morel
  • Patent number: 4156101
    Abstract: Process for the telomerization of olefins with secondary alcohols comprising admixing a secondary alcohol telogen with a mono-olefinically unsaturated hydrocarbon taxogen in catalytically effective amounts of a free radical generating initiator in a reaction zone, the telogen to taxogen molar ratio in the reaction zone being greater than about 1:1 as measured on the effluent stream from the reaction zone, at a temperature ranging from about 125.degree. C. to about 275.degree. C. and that a pressure varying from about 2000 psi to about 10,000 psi.
    Type: Grant
    Filed: March 20, 1974
    Date of Patent: May 22, 1979
    Assignee: Dart Industries Inc.
    Inventors: Michael Erchak, George E. Cremeans, Elmer J. Bradbury
  • Patent number: 4091041
    Abstract: 2-ALKOXYTETRAHYDROFURANS ARE CONVERTED TO 1,4-DIOLS UNDER HYDROLYSIS-HYDROGENATION CONDITIONS. The method may be coupled with the synthesis of 2-alkoxytetrahydrofurans to provide a highly efficient, two-step conversion of allylic alcohols to butanediols.
    Type: Grant
    Filed: June 13, 1977
    Date of Patent: May 23, 1978
    Assignee: General Electric Company
    Inventor: William Edward Smith