Ethylenically Unsaturated Hydroxy Compound Produced Patents (Class 568/908)
  • Patent number: 9242864
    Abstract: The invention relates to a method for producing lithium metal phosphates of a formula LiMPO4, wherein M is at least one type of bivalent metal, preferably selected from the first transition metal range. The inventive method consists in reacting a lithium phosphate with a metal salt and an acid phosphate source in a polar solvent for converting into a corresponding M-containing phosphate, in adding a basic lithium source for obtaining a precursor mixture for a desired lithium metal phosphate, in converting and separating the thus obtained mixture, preferably in hydrothermal conditions, in such a way that a desired final product is obtained, thereby receiving a lithium-containing filtrate. The addition of the basic lithium source initiates a lithium ion precipitation in the form of a lithium phosphate. The thus obtainable lithium phosphate can be reused in the form of a raw material, whereby said cycle enables lithium to be highly reusable.
    Type: Grant
    Filed: March 17, 2006
    Date of Patent: January 26, 2016
    Assignee: JOHNSON MATTHEY PLC
    Inventors: Gerhard Nuspl, Christian Vogler, Josefine Zuber
  • 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
  • Patent number: 7847135
    Abstract: The invention is a process to produce allyl alcohol from propylene oxide. The process comprises isomerizing propylene oxide in the presence of a lithium phosphate catalyst which contains boron and from 2000 to 4000 ppm sodium. The propylene oxide conversion is 37 percent or lower.
    Type: Grant
    Filed: October 30, 2009
    Date of Patent: December 7, 2010
    Assignee: Lyondell Chemical Technology, L.P.
    Inventor: Daniel F. White
  • Patent number: 7399891
    Abstract: This invention relates to a process for the production of an alcohol, the process comprising (a) reacting an olefin and water in the presence of a catalyst under conditions sufficient to form a crude alcohol stream comprising alcohol, and a dialkyl ether; (b) separating at least a portion of the crude alcohol stream into an alcohol-containing stream and a dialkyl ether stream; (c) contacting at least a portion of the dialkyl ether stream with an ether decomposition catalyst, the ether decomposition catalyst comprising a mixed metal oxide having the following composition XmYnZpOq where X is at least one metal selected from Group 4 of the Periodic Table of Elements, Y is at least one metal selected from Group 3 (including the Lanthanides and Actinides) and Group 6 of the Periodic Table of Elements and Z is at least one metal selected from Groups 7, 8, and 11 of the Periodic Table of Elements; m, n, p, and q are the atomic ratios of their respective components and, when m is 1, n is from about 0.01 to about 0.
    Type: Grant
    Filed: June 8, 2005
    Date of Patent: July 15, 2008
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Charles M Yarbrough, Brian William Roberts, Dennis Jay Davoren, Kenneth Joseph Buturla, Carl Stotz Katzenstein, Doron Levin, Hans Georg Korsten, Vijay Swarup
  • Publication number: 20080139854
    Abstract: A process for preparing activated polyethylene glycols is disclosed. In some embodiments, the process includes reacting a molten polyethylene glycol with an activator. In other embodiments, the process includes reacting a polyethylene glycol with an activator in the absence of a solvent. The process may be carried out in an inert gas atmosphere, at a temperature at least 10° C. above the melting point of polyethylene glycol, and/or with the activator provided in molar excess of the polyethylene glycol. The invention further provides activated polyethylene glycols produced by this process and their use in a variety of pharmaceutical, medical, cosmetic and chemical applications.
    Type: Application
    Filed: February 4, 2008
    Publication date: June 12, 2008
    Inventors: Marie-Pierre Faure, Kirill Shingel
  • Patent number: 7166753
    Abstract: A process for producing a carbonyl compound involves allowing water to undergo phase transition to a supercritical or subcritical state in the presence of an alcohol compound so as to produce/generate water-derived hydrogen and at the same time convert the alcohol compound into a corresponding carbonyl compound. Specifically, the process is carried out by introducing the alcohol in a reaction tube along with water and heating and/or pressurizing the mixture of the alcohol and the water to bring the water into a subcritical or supercritical state. In this manner, water-derived hydrogen is produced and the alcohol is converted to a corresponding carbonyl compound. The process is preferably carried out in an oxygen-free environment.
    Type: Grant
    Filed: April 9, 2003
    Date of Patent: January 23, 2007
    Assignee: Suntory Limited
    Inventors: Koichi Nakahara, Kenzo Nagami, Okitsugu Kajimoto, Kazuya Kobiro
  • Patent number: 7161047
    Abstract: A process for preparing a secondary alcohol which is characterized in adding a primary or a secondary amine in the reaction system in case that the secondary alcohol is prepared by hydrogenating in the presence of a noble metal, an epoxy derivative represented by the following formula, wherein R1 and R2 are the same or different, an organic group not containing aldehyde group or ketone group therein or hydrogen atom, provided that both R1 and R2 are not simultaneously hydrogen atom.
    Type: Grant
    Filed: March 29, 2005
    Date of Patent: January 9, 2007
    Assignee: Daiso Co., Ltd.
    Inventors: Yasushi Miki, Daisuke Fukumoto, Masafumi Mikami
  • Patent number: 7102037
    Abstract: A process for selectively converting a dialkyl ether to the corresponding alkene and alkanol comprises contacting a feed containing at least one dialkyl ether with a catalyst comprising a mixed metal oxide which comprises at least one metal selected from Group 4 of the Periodic Table of Elements and at least one metal selected from Group 3 (including the Lanthanides and Actinides) and Group 6 of the Periodic Table of Elements.
    Type: Grant
    Filed: December 16, 2004
    Date of Patent: September 5, 2006
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Doron Levin, Shifang Luo, James Clarke Vartuli, Charles Morris Yarbrough, Dane Clark Grenoble
  • Patent number: 6897343
    Abstract: The invention relates to a process for the preparation of 1,2-propanediol from propylene oxide, which process involves contacting propylene oxide with carbon dioxide in the presence of a homogeneous phosphorus containing catalyst to obtain propylene carbonate, optionally removing at least part of the carbon dioxide, adding water and/or an alcohol to the reaction product containing propylene carbonate and phosphorus containing catalyst and contacting the mixture with a heterogeneous catalyst to obtain 1,2-propanediol in combination with dialkylcarbonate and/or carbon dioxide, and separating 1,2-propanediol from the reaction product obtained.
    Type: Grant
    Filed: December 19, 2003
    Date of Patent: May 24, 2005
    Assignee: Shell Oil Company
    Inventors: Klaas Lambertus Von Hebel, Jean-Paul Lange
  • Patent number: 6803491
    Abstract: A new method for preparing lithium phosphate catalysts is disclosed. The method comprises precipitating a lithium phosphate from a mixture comprising a first aqueous solution which contains lithium and sodium ions and a second aqueous solution which contains phosphate and borate ions. The resultant lithium phosphate catalyst has increased activity and selectivity in the isomerization of an alkylene oxide to the corresponding allylic alcohol.
    Type: Grant
    Filed: November 13, 2003
    Date of Patent: October 12, 2004
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Wilfred Po-sum Shum
  • Patent number: 6790999
    Abstract: Disclosed is a process for the continuous, semi-continuous or batch production of 3-buten-1-ol from 3,4-epoxy-1-butene wherein 3,4-epoxy-1-butene and formic acid are fed to a reaction zone having a catalyst solution comprising a palladium(0) compound, a tertiary phosphine, a trialkylamine and an organic solvent. Preferably in the operation of this invention, 3-buten-1-ol product and reaction side products serve as the organic solvent for the process. The preferred mode of operation is continuous addition of reactants to the reaction mixture with simultaneous, continuous distillation of a reaction product comprising 3-buten-1-ol.
    Type: Grant
    Filed: February 28, 2003
    Date of Patent: September 14, 2004
    Assignee: Eastman Chemical Company
    Inventor: Stephen Neal Falling
  • Publication number: 20040171892
    Abstract: Disclosed is a process for the continuous, semi-continuous or batch production of 3-buten-1-ol from 3,4-epoxy-1-butene wherein 3,4-epoxy-1-butene and formic acid are fed to a reaction zone having a catalyst solution comprising a palladium(0) compound, a tertiary phosphine, a trialkylamine and an organic solvent. Preferably in the operation of this invention, 3-buten-1-ol product and reaction side products serve as the organic solvent for the process. The preferred mode of operation is continuous addition of reactants to the reaction mixture with simultaneous, continuous distillation of a reaction product comprising 3-buten-1-ol.
    Type: Application
    Filed: February 28, 2003
    Publication date: September 2, 2004
    Inventor: Stephen Neal Falling
  • Patent number: 6696612
    Abstract: A process for producing isobutylene and methanol, comprising decomposing methyl-tert-butylether into isobutylene and methanol, and separating into isobutylene and methanol, thereby individually recovering isobutylene and methanol, the process comprising the following steps: a first step of subjecting methyl-tert-butylether to decomposition in the presence of a solid acid catalyst; a second step of washing the resultant with water to separate into an oil layer and a water layer; a third step of subjecting the oil layer to distillation to obtain a fraction from the top of the distillation column and a fraction from the bottom thereof; and a fourth step of subjecting the water layer to distillation to obtain a fraction containing methanol from the top of the distillation column, a fraction containing water from the bottom thereof and a fraction rich in tert-butanol from a side cut thereof, and then recycling a part or whole of the fraction from the side cut to the first step.
    Type: Grant
    Filed: June 18, 2002
    Date of Patent: February 24, 2004
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masanobu Yamase, Yoshiaki Suzuki, Takayuki Moritou
  • Publication number: 20030065230
    Abstract: A catalyst system that can be used to achieve (a) preparation of allylic alcohols by rearrangement of the corresponding epoxide, when the allylic alcohol is a desired product; (b) subsequent reaction, e.g., selective oxidation, of the allylic alcohols obtained in step (a) to afford a desired product, e.g., alpha, beta-unsaturated carbonyl compounds; and/or (c) the ability to perform steps a) and b) in a one-pot process. In one embodiment, the catalyst system includes (i) at least one primary catalyst includes one or more homogeneous or heterogeneous, inorganic, organic or complex metal-containing compound, and (ii) at least one activator/modifier comprising at least one phenolic compound.
    Type: Application
    Filed: July 5, 2001
    Publication date: April 3, 2003
    Inventors: Gennadiy G. Kolomeyer, Jacob S. Oyloe
  • Publication number: 20030045739
    Abstract: An integrated process for the production of a dialkyl carbonate and a diol from an alkylene oxide, carbon dioxide and an aliphatic monohydric alcohol is described in which an alkylene oxide is first reacted with carbon dioxide in the presence of a homogeneous carbonation catalyst to provide a corresponding cyclic carbonate and the cyclic carbonate is then reacted with an aliphatic monohydric alcohol in the presence of the homogeneous carbonation catalyst and/or a heterogeneous transesterification catalyst and recycling the homogeneous carbonation catalyst to provide a corresponding dialkyl carbonate and diol.
    Type: Application
    Filed: June 22, 2001
    Publication date: March 6, 2003
    Inventors: J. Scott Buchanan, Zhaozhong Jiang, Jose G. Santiesteban, William A. Weber
  • Patent number: 6103943
    Abstract: Disclosed is a process for the synthesis of 3-buten-1-ol by contacting 3,4-epoxy-1-butene and formic acid with a homogeneous catalyst solution comprising a palladium(0) compound, a tertiary phosphine and a trialkylamine dissolved in tetrahydrofuran.
    Type: Grant
    Filed: January 20, 1998
    Date of Patent: August 15, 2000
    Assignee: Eastman Chemical Company
    Inventor: Charles Allan McCombs
  • Patent number: 5600033
    Abstract: Improved catalysts for isomerizing epoxides to allylic alcohols are disclosed. The catalysts contain lithium phosphate supported on high-purity silica. The use of high-purity silica as a support results in improved epoxide conversion and allylic alcohol selectivity, and reduced by-product generation. The invention includes a process for isomerizing epoxides using the catalysts. The process is well-suited to the manufacture of allyl alcohol from propylene oxide.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: February 4, 1997
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: Mahmoud K. Faraj
  • Patent number: 5600034
    Abstract: A method for producing allyl alcohols, which comprises heat-treating diallyl ethers in the presence of a catalyst containing a palladium compound and a phosphorus compound to convert them to allyl alcohols, wherein the heat treatment is conducted under such conversion reaction conditions that the value of function F represented by the following formula is within a range of 0.ltoreq.F<100, the concentration of allyl alcohols in the conversion reaction solution is not higher than 20 wt %, and the Pd concentration in the conversion reaction solution is within a range of from 0.005 to 1.0 wt %:F=.theta.t.multidot.[Pd].multidot.(t-100wherein .theta.t is the conversion reaction time (hours), [Pd] is the Pd concentration (wt %) in the conversion reaction solution, and T is the conversion reaction temperature (.degree.C.
    Type: Grant
    Filed: November 20, 1995
    Date of Patent: February 4, 1997
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Tomoyuki Mori, Hiroshi Kameo, Shinji Isogai, Soichiro Saita
  • Patent number: 5457247
    Abstract: A novel process for preparing enantiomerically pure (S)- or (R)-but-3-en-2-ol compounds includes the following reaction steps:(a) reacting an alkyl ester of D- or L-lactic acid with a hydropyran compound to obtain a lactate ester having a hydropyranyl ether group,(b) reducing the lactate ester with an aluminum hydride at a temperature below 0.degree. C. to obtain a propionaldehyde having a hydropyranyl ether group,(c) reacting the propionaldehyde with an alkyl phosphonium salt to obtain a 3-butene having a hydropyranyl ether group, and(d) cleaving the hydropyranyl ether group to prepare the enantiomerically pure (S)- or (R)- but-3-en-2-ol.
    Type: Grant
    Filed: December 21, 1994
    Date of Patent: October 10, 1995
    Assignee: Boehringer Ingelheim KG
    Inventors: Franz D. Klingler, Manfred Psiorz
  • Patent number: 5406007
    Abstract: Disclosed is a process for the conversion of conjugated epoxyalkenes to unsaturated alcohols wherein a conjugated epoxyalkene is catalytically hydrogenated in the presence of a sulfur-modified or sulfided nickel catalyst whereby the epoxide ring is hydrogenolyzed without concomitant hydrogenation of the olefinic unsaturation thereby producing allylic and/or homoallylic alcohols.
    Type: Grant
    Filed: July 15, 1994
    Date of Patent: April 11, 1995
    Assignee: Eastman Chemical Company
    Inventor: Stephen N. Falling
  • Patent number: 5116916
    Abstract: Compositions containing sulfuric acid and one or more of certain chalcogen-containing compounds in which the chalcogen compound/H.sub.2 SO.sub.4 molar ratio is below 2 contain the mono-adduct of sulfuric acid which is catalytically active for promoting organic chemical reactions. Suitable chalcogen-containing compounds have the empirical formula ##STR1## wherein X is a chalcogen, each of R.sub.1 and R.sub.2 is independently selected from hydrogen, NR.sub.3 R.sub.4, and NR.sub.5, at least one of R.sub.1 and R.sub.2 is other than hydrogen, each of R.sub.3 and R.sub.4 is hydrogen or a monovalent organic radical, and R.sub.5 is a divalent organic radical. Such compositions are useful for catalyzing organic reactions such as oxidation, oxidative addition, reduction, reductive addition, esterification, transesterification, hydrogenation, isomerication (including racemization of optical isomers), alkylation, polymerization, demetallization of organometallics, nitration, Friedel-Crafts reactions, and hydrolysis.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: May 26, 1992
    Assignee: Union Oil Company of California
    Inventor: Donald C. Young
  • Patent number: 5113003
    Abstract: The silicon-containing phenoxy ethers are of the formula III: ##STR1## wherein R.sup.1 and R.sup.2 which may be the same or different are selected from H, --R.sup.3 --X, aliphatic hydrocarbyl having 1-6 carbon atoms or aryl, or substituted derivatives thereof, provided that not more than one of R.sup.1 and R.sup.2 is H;R.sup.3 is a divalent C.sub.1 -C.sub.30 aliphatic and/or aromatic hydrocarbyl group which may optionally be substituted, or interrupted, by a hetero atom;R.sup.4 and R.sup.5 which may be the same or different are H, ##STR2## or an ortho para directing activating group for aromatic electrophilic substitution, other than an amine;and X is a reactive functional group capable of undergoing an acid-catalyzed electrophilic aromatic substitution reaction with a phenol, for example an aldehyde group. They can be polymerized to produce silicone-modified polymers of the phenol-aldehyde type without the use of free aldehyde.
    Type: Grant
    Filed: March 20, 1991
    Date of Patent: May 12, 1992
    Assignee: Loctite (Ireland) Limited
    Inventors: John G. Woods, Pauline Coakley
  • Patent number: 5087773
    Abstract: Threo- and erythro- epoxy alcohols are converted in high yield to trans- and cis-allyl alcohols, respectively. The threo epoxy alcohol or erythro-epoxy alcohol is reacted with a toluenesulfonic anhydride to form a threo- or erythro- glycidyl tosylate. The glycidyl tosylate is contacted with tellurium ion, in the form, e.g. of Na.sub.2 Te that has been prepared by adding tellurium in elemental form and sodium borohydride or lithium triethyl borohydride to dimethylformamide (DMF). The DMF has a low volatility and permits further work to be carried out at elevated temperatures. The glycidyl tosylate is added to the sodium telluride in DMF, and is permitted to react. The tellurium ion displaces the tosylate and opens the epoxide to form an unstable alkoxy epitelluride. This epitelluride is a short-lived intermediate, and extrudes the tellurium, leaving the olefin. The opening of the epoxide required the adoption of an anti configuration.
    Type: Grant
    Filed: April 23, 1990
    Date of Patent: February 11, 1992
    Assignee: Syracuse University
    Inventors: Donald C. Dittmer, Christopher K. Murphy, Robert Discordia
  • Patent number: 5004843
    Abstract: Process for preparing predominantly Z-substituted allylic alcohols of the formula: ##STR1## wherein R.sup.1 is a straight or branched C.sub.1 -C.sub.25 alkyl group optionally bearing at least one substituent and/or at least one unsaturated linkage and R.sup.2 is a hydrogen atom or a methyl group, which comprises reacting a vinyl epoxide of the formula: ##STR2## wherein R.sup.2 is as defined above with an organolithium compound of the formula above. More particularly, there is disclosed a process for R.sup.1 --Li wherein R.sup.1 is as defined above; particularly, process for preparing .alpha.-santalol of the formula: ##STR3## which comprises reacting 3-methyl-3,4-epoxybutene-1 with lithiomethyl-2,3-dimethyltricyclo[2.2.1.0.sup.2,6 ]heptane.
    Type: Grant
    Filed: May 29, 1990
    Date of Patent: April 2, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mitsuhisa Tamura, Gohu Suzukamo, Ken-ichi Hirose
  • Patent number: 4973765
    Abstract: Dien-1-ols of the general formula I ##STR1## where the radicals R.sup.1 to R.sup.7 are identical to or different from one another and each is hydrogen or straight-chain or branched alkyl of 1-12 carbon atoms and n is 1-14, are prepared by dehydrating a hydroxyalkenyl tert-butyl ether of the formula II ##STR2## in the presence of an acidic catalyst at elevated temperatures and essentially at the same time splitting off the tert-butyl protective group, as is 9-hydroxydodec-10-enyl 1-tert-butyl ether which is useful as an intermediate for synthesizing 8,10-dodecadienol.
    Type: Grant
    Filed: December 20, 1989
    Date of Patent: November 27, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Mackenroth, Wolfgang Hoelderich, Rainer Becker, Walter Seufert
  • Patent number: 4935451
    Abstract: A two step procedure converts an epoxide residue from a Sharpless kinetic resolution of secondary allyl alcohols into an allyl alcohol of the desired chirality. The Sharpless system selectively epoxidizes one enantiomer of the allyl alcohol and leaves the other substantially unreacted. Then the epoxy alcohol is treated with methanesulfonyl anhydride and converted to epoxy mesylate. This product is contacted with a telluride salt in aqueous solution to convert it to the desired allyl alcohol with the chiral center inverted. This technique effects nearly complete conversion of racemic starting material to a single desired enantiomer.
    Type: Grant
    Filed: September 11, 1989
    Date of Patent: June 19, 1990
    Assignee: Syracuse University
    Inventors: Donald C. Dittmer, Robert P. Discordia
  • Patent number: 4925991
    Abstract: Dien-1-ols of the general formula I ##STR1## where the radicals R.sup.1 to R.sup.7 are identical to or different from one another and each is hydrogen or straight-chain or branched alkyl or 1-12 carbon atoms and n is 1-14, are prepared by dehydrating a hydroxylalkenyl tert-butyl ether of the formula II ##STR2## in the presence of an acidic catalyst at elevated tempertures and essentially at the same time splitting off the tert-butyl protective group, as is 9-hydroxydodec-10-enyl 1-tert-butyl ether which is useful as an intermediate for synthesizing 8,10-dodecadienol.
    Type: Grant
    Filed: August 24, 1988
    Date of Patent: May 15, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Mackenroth, Wolfgang Hoelderich, Rainer Becker, Walter Seufert
  • Patent number: 4886891
    Abstract: The present invention provides a process for preparing a 1,1-disubstituted ethylene derivative of the formula ##STR1## which comprises reacting lead with a carbinol derivative of the formula ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, X, Y, m and n are defined in the specification. The reaction is conducted more advantageously in the presence of a metal having higher ionization tendency than lead.
    Type: Grant
    Filed: December 18, 1987
    Date of Patent: December 12, 1989
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Shigeru Torii, Masatoshi Taniguchi, Michio Sasaoka, Yoshihisa Tomotaki, Mitsuo Akada, Hideo Tanaka, Akira Suzuki, Shiro Yamashita
  • Patent number: 4720598
    Abstract: Process for preparing a basic lithium phosphate catalyst suitable for the gas phase isomerization of an alkene oxide to the corresponding alcohol, in which process an aqueous solution of a lithium compound is mixed in the presence of an alkali metal hydroxide with an aqueous solution of a phosphate salt or phosphoric acid, the process being characterized in that the aqueous solution of the phosphate salt or phosphoric acid is added evenly during a period of at least six hours to the homogeneously stirred aqueous solution of the lithium compound, upon which the precipitated lithium phosphate is washed with water and subsequently calcined.
    Type: Grant
    Filed: June 23, 1986
    Date of Patent: January 19, 1988
    Assignee: Stamicarbon B.V.
    Inventor: Hubertus B. Scholte
  • Patent number: 4590300
    Abstract: Allyl methyl ethers are transetherified with alcohols by use of a catalyst of a solid acid that contains no mercury or cuprous salt catalyst.
    Type: Grant
    Filed: January 9, 1985
    Date of Patent: May 20, 1986
    Assignee: The Dow Chemical Company
    Inventors: Michael J. Mullins, Percy J. Hamlin
  • Patent number: 4267363
    Abstract: Synthesis and intermediates for making an insect pheromone useful in the control of the yellow scale.
    Type: Grant
    Filed: June 26, 1978
    Date of Patent: May 12, 1981
    Assignee: Zoecon Corporation
    Inventors: Richard J. Anderson, Clive A. Henrick
  • Patent number: 4228093
    Abstract: Synthesis of an attractant (11Z,13Z)-11,13-hexadecadienal for the navel orangeworm Amyelois transitella, and intermediates therefor.
    Type: Grant
    Filed: October 18, 1979
    Date of Patent: October 14, 1980
    Assignee: Zoecon Corporation
    Inventors: Robert L. Carney, Clive A. Henrick
  • Patent number: 4189614
    Abstract: A process for the stereoselective preparation of sexual pheromones is disclosed. The process involves reacting a compound of the formula ##STR1## in which the conjugated diene is of the trans-trans (E--E) stereochemical configuration with a compound of the formulaXMg--(CH.sub.2).sub.n --CH.sub.
    Type: Grant
    Filed: February 14, 1979
    Date of Patent: February 19, 1980
    Assignee: Institut National de la Recherche Agronomique
    Inventors: Daniel Samain, Charles Descoins, Gerhard Kunesch
  • Patent number: 4178297
    Abstract: This invention relates to the preparation of unsaturated alcohols useful as flavor and fragrance compounds. More specifically, this invention relates to the preparation of predominately cis-unsaturated alcohols by reacting a cis-1-alkenylaluminum dialkyl compound with an epoxide compound followed by hydrolysis. The alkenyl moiety has one or more double bond carbon-to-carbon linkage and from 5 to 20 carbon atoms that can be optionally substituted with the substituents selected from alkyl and aromatic radicals having 1 to 12 carbon atoms.
    Type: Grant
    Filed: November 16, 1978
    Date of Patent: December 11, 1979
    Assignee: Texas Alkyls, Inc.
    Inventors: Spencer C. Watson, Dennis B. Malpass, G. Scott Yeargin
  • Patent number: 4133815
    Abstract: This invention relates to the preparation of unsaturated alcohols useful as flavor and fragrance compounds. More specifically, this invention relates to the preparation of predominantly cis-unsaturated alcohols by reacting a cis-1-alkenylaluminum dialkyl compound with an epoxide compound followed by hydrolysis. The alkenyl moiety has one or more double bond carbon-to-carbon linkage and from 5 to 20 carbon atoms that can be optionally substituted with the substituents selected from alkyl and aromatic radicals having 1 to 12 carbon atoms.
    Type: Grant
    Filed: March 11, 1976
    Date of Patent: January 9, 1979
    Assignee: Texas Alkyls, Inc.
    Inventors: Spencer C. Watson, Dennis B. Malpass, G. Scott Yeargin
  • Patent number: 4110357
    Abstract: This invention relates to the preparation of unsaturated alcohols useful as flavor and fragrance compounds. More specifically, this invention relates to the preparation of predominately cis-unsaturated alcohols by reacting a cis-1-alkenyl-aluminum dialkyl compound with an epoxide compound followed by hydrolysis. The alkenyl moiety has one or more double bond carbon-to-carbon linkage and from 5 to 20 carbon atoms that can be optionally substituted with the substituents selected from alkyl and aromatic radicals having 1 to 12 carbon atoms.
    Type: Grant
    Filed: November 8, 1976
    Date of Patent: August 29, 1978
    Assignee: Texas Alkyls, Inc.
    Inventors: Spencer C. Watson, Dennis B. Malpass, G. Scott Yeargin