Ethylenically Unsaturated Hydroxy Compound Produced Patents (Class 568/908)
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Patent number: 9242864Abstract: 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: GrantFiled: March 17, 2006Date of Patent: January 26, 2016Assignee: JOHNSON MATTHEY PLCInventors: Gerhard Nuspl, Christian Vogler, Josefine Zuber
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Patent number: 8455698Abstract: 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: GrantFiled: December 30, 2009Date of Patent: June 4, 2013Assignee: Evonik Degussa GmbHInventors: Michael A. R. Meier, Anastasiya Rybak, Dominik Geisker
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Patent number: 8394996Abstract: 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: GrantFiled: January 12, 2010Date of Patent: March 12, 2013Assignee: Evonik Degussa GmbHInventors: Michael A. R. Meier, Anastasiya Rybak, Dominik Geisker, Peter Hannen, Martin Roos
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Patent number: 7847135Abstract: 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: GrantFiled: October 30, 2009Date of Patent: December 7, 2010Assignee: Lyondell Chemical Technology, L.P.Inventor: Daniel F. White
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Patent number: 7399891Abstract: 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: GrantFiled: June 8, 2005Date of Patent: July 15, 2008Assignee: 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
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Publication number: 20080139854Abstract: 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: ApplicationFiled: February 4, 2008Publication date: June 12, 2008Inventors: Marie-Pierre Faure, Kirill Shingel
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Patent number: 7166753Abstract: 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: GrantFiled: April 9, 2003Date of Patent: January 23, 2007Assignee: Suntory LimitedInventors: Koichi Nakahara, Kenzo Nagami, Okitsugu Kajimoto, Kazuya Kobiro
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Patent number: 7161047Abstract: 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: GrantFiled: March 29, 2005Date of Patent: January 9, 2007Assignee: Daiso Co., Ltd.Inventors: Yasushi Miki, Daisuke Fukumoto, Masafumi Mikami
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Patent number: 7102037Abstract: 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: GrantFiled: December 16, 2004Date of Patent: September 5, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: Doron Levin, Shifang Luo, James Clarke Vartuli, Charles Morris Yarbrough, Dane Clark Grenoble
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Patent number: 6897343Abstract: 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: GrantFiled: December 19, 2003Date of Patent: May 24, 2005Assignee: Shell Oil CompanyInventors: Klaas Lambertus Von Hebel, Jean-Paul Lange
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Patent number: 6803491Abstract: 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: GrantFiled: November 13, 2003Date of Patent: October 12, 2004Assignee: Arco Chemical Technology, L.P.Inventor: Wilfred Po-sum Shum
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Patent number: 6790999Abstract: 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: GrantFiled: February 28, 2003Date of Patent: September 14, 2004Assignee: Eastman Chemical CompanyInventor: Stephen Neal Falling
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Publication number: 20040171892Abstract: 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: ApplicationFiled: February 28, 2003Publication date: September 2, 2004Inventor: Stephen Neal Falling
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Patent number: 6696612Abstract: 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: GrantFiled: June 18, 2002Date of Patent: February 24, 2004Assignee: Sumitomo Chemical Company, LimitedInventors: Masanobu Yamase, Yoshiaki Suzuki, Takayuki Moritou
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Publication number: 20030065230Abstract: 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: ApplicationFiled: July 5, 2001Publication date: April 3, 2003Inventors: Gennadiy G. Kolomeyer, Jacob S. Oyloe
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Publication number: 20030045739Abstract: 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: ApplicationFiled: June 22, 2001Publication date: March 6, 2003Inventors: J. Scott Buchanan, Zhaozhong Jiang, Jose G. Santiesteban, William A. Weber
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Patent number: 6103943Abstract: 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: GrantFiled: January 20, 1998Date of Patent: August 15, 2000Assignee: Eastman Chemical CompanyInventor: Charles Allan McCombs
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Patent number: 5600033Abstract: 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: GrantFiled: June 5, 1995Date of Patent: February 4, 1997Assignee: ARCO Chemical Technology, L.P.Inventor: Mahmoud K. Faraj
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Patent number: 5600034Abstract: 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: GrantFiled: November 20, 1995Date of Patent: February 4, 1997Assignee: Mitsubishi Chemical CorporationInventors: Tomoyuki Mori, Hiroshi Kameo, Shinji Isogai, Soichiro Saita
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Patent number: 5457247Abstract: 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: GrantFiled: December 21, 1994Date of Patent: October 10, 1995Assignee: Boehringer Ingelheim KGInventors: Franz D. Klingler, Manfred Psiorz
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Patent number: 5406007Abstract: 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: GrantFiled: July 15, 1994Date of Patent: April 11, 1995Assignee: Eastman Chemical CompanyInventor: Stephen N. Falling
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Patent number: 5116916Abstract: 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: GrantFiled: January 29, 1988Date of Patent: May 26, 1992Assignee: Union Oil Company of CaliforniaInventor: Donald C. Young
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Patent number: 5113003Abstract: 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: GrantFiled: March 20, 1991Date of Patent: May 12, 1992Assignee: Loctite (Ireland) LimitedInventors: John G. Woods, Pauline Coakley
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Patent number: 5087773Abstract: 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: GrantFiled: April 23, 1990Date of Patent: February 11, 1992Assignee: Syracuse UniversityInventors: Donald C. Dittmer, Christopher K. Murphy, Robert Discordia
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Patent number: 5004843Abstract: 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: GrantFiled: May 29, 1990Date of Patent: April 2, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Mitsuhisa Tamura, Gohu Suzukamo, Ken-ichi Hirose
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Patent number: 4973765Abstract: 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: GrantFiled: December 20, 1989Date of Patent: November 27, 1990Assignee: BASF AktiengesellschaftInventors: Wolfgang Mackenroth, Wolfgang Hoelderich, Rainer Becker, Walter Seufert
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Patent number: 4935451Abstract: 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: GrantFiled: September 11, 1989Date of Patent: June 19, 1990Assignee: Syracuse UniversityInventors: Donald C. Dittmer, Robert P. Discordia
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Patent number: 4925991Abstract: 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: GrantFiled: August 24, 1988Date of Patent: May 15, 1990Assignee: BASF AktiengesellschaftInventors: Wolfgang Mackenroth, Wolfgang Hoelderich, Rainer Becker, Walter Seufert
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Patent number: 4886891Abstract: 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: GrantFiled: December 18, 1987Date of Patent: December 12, 1989Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Shigeru Torii, Masatoshi Taniguchi, Michio Sasaoka, Yoshihisa Tomotaki, Mitsuo Akada, Hideo Tanaka, Akira Suzuki, Shiro Yamashita
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Patent number: 4720598Abstract: 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: GrantFiled: June 23, 1986Date of Patent: January 19, 1988Assignee: Stamicarbon B.V.Inventor: Hubertus B. Scholte
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Patent number: 4590300Abstract: 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: GrantFiled: January 9, 1985Date of Patent: May 20, 1986Assignee: The Dow Chemical CompanyInventors: Michael J. Mullins, Percy J. Hamlin
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Patent number: 4267363Abstract: Synthesis and intermediates for making an insect pheromone useful in the control of the yellow scale.Type: GrantFiled: June 26, 1978Date of Patent: May 12, 1981Assignee: Zoecon CorporationInventors: Richard J. Anderson, Clive A. Henrick
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Patent number: 4228093Abstract: Synthesis of an attractant (11Z,13Z)-11,13-hexadecadienal for the navel orangeworm Amyelois transitella, and intermediates therefor.Type: GrantFiled: October 18, 1979Date of Patent: October 14, 1980Assignee: Zoecon CorporationInventors: Robert L. Carney, Clive A. Henrick
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Patent number: 4189614Abstract: 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: GrantFiled: February 14, 1979Date of Patent: February 19, 1980Assignee: Institut National de la Recherche AgronomiqueInventors: Daniel Samain, Charles Descoins, Gerhard Kunesch
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Patent number: 4178297Abstract: 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: GrantFiled: November 16, 1978Date of Patent: December 11, 1979Assignee: Texas Alkyls, Inc.Inventors: Spencer C. Watson, Dennis B. Malpass, G. Scott Yeargin
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Patent number: 4133815Abstract: 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: GrantFiled: March 11, 1976Date of Patent: January 9, 1979Assignee: Texas Alkyls, Inc.Inventors: Spencer C. Watson, Dennis B. Malpass, G. Scott Yeargin
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Patent number: 4110357Abstract: 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: GrantFiled: November 8, 1976Date of Patent: August 29, 1978Assignee: Texas Alkyls, Inc.Inventors: Spencer C. Watson, Dennis B. Malpass, G. Scott Yeargin