At Least Three Oxygens Containing Patents (Class 568/600)
  • Patent number: 10322397
    Abstract: A method for forming poly(dimethoxymethane) includes a step of separating a formaldehyde-containing blend into a first bottom stream and a first top stream. The first formaldehyde-containing blend includes methanol, formaldehyde, and water while the first bottom stream includes water. The first top stream includes dimethoxymethane that is produced from the reaction between methanol and formaldehyde. The first top stream is separated into a second bottom stream and a second top stream. The second bottom stream includes poly(dimethoxymethane) while the second top stream includes dimethoxymethane, methanol, and ethanol. The second top stream is separated into a third bottom stream and a third top stream. Third bottom stream includes methanol and ethanol while the third top stream includes dimethoxymethane. The third top steam can be recycled to form additional poly(dimethoxymethane). A system that implements the method is also provided.
    Type: Grant
    Filed: September 1, 2017
    Date of Patent: June 18, 2019
    Assignee: GAS TECHNOLOGIES LLC
    Inventors: Evan Visser, Walter Breidenstein
  • Patent number: 9631055
    Abstract: Pre-polymer according to structure (I) X—(R2—O)n—CH2—O—(R1—O)m—CH2—(O—R2)p—X (I) wherein R1 and R2 can be the same or different and are selected from alkane chains containing 2-10 carbon atoms, X is a halogen atom, and n, m, and p are integers that can be the same of different and have a value in the range 1-6. The use of this pre-polymer in the preparation of a liquid polysulfide polymer allows better control over the sulfur and oxygen content and the polarity of the resulting polymer.
    Type: Grant
    Filed: June 13, 2014
    Date of Patent: April 25, 2017
    Assignee: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
    Inventors: Manfred Menzel, Daniela Lungu, Olaf Klobes, Heinz Aldenhoven, Antonius Van Pelt, Volker Burkhardt
  • Patent number: 9309178
    Abstract: The present invention is concerned with a process for preparing acetals and ketals which comprises (i) reacting an aldehyde or ketone with an alcohol in the presence of a solid acid at a temperature of below ?40° C., and (ii) removing water and lower aliphatic alcohol and/or sugar alcohol from the reaction product by pervaporation.
    Type: Grant
    Filed: June 29, 2012
    Date of Patent: April 12, 2016
    Assignee: DSM IP ASSETS B.V.
    Inventor: Thomas Clavey
  • Patent number: 8952203
    Abstract: A method for manufacturing an acetal compound represented by the formula [1] in which the steps (A) to (D) as defined herein are performed sequentially, and an acetal compound of the formula [1] which is produced by the method: wherein n is 0 or 1 provided that R1 groups may be bonded or may not be bonded to each other when n is 0; R1 is an alkyl group having 1 or 2 carbon atoms or an alkylene group having 1 or 2 carbon atoms and the R1 groups may be same or different from each other; and R2 is an alkylene group having 1 or 6 carbon atoms.
    Type: Grant
    Filed: March 23, 2012
    Date of Patent: February 10, 2015
    Assignee: NOF Corporation
    Inventors: Takashi Ichikawa, Shuichi Yoshimura, Ken-ichiro Nakamoto
  • Publication number: 20140182484
    Abstract: A polyoxymethylene polymer is disclosed that contains long-chain alkyl end groups. The polyoxymethylene polymer may be formed by using a Bis-alkylformal as a chain transfer agent during production of the polymer. In one embodiment, the Bis-alkylformal is dissolved in a monomer, such as trioxane, during production of the polymer. In one embodiment, a branching agent may also be present with one or more monomers for producing a branched polyoxymethylene polymer. In this manner, greater amounts of alkyl end groups can be incorporated into the polymer. The resulting polymer has excellent flow characteristics. The polymer may be used to form various molded articles with excellent tribological properties.
    Type: Application
    Filed: December 20, 2013
    Publication date: July 3, 2014
    Applicant: Ticona GmbH
    Inventors: Andre Hebel, Michael Haubs, Ursula Ziegler
  • Patent number: 8753997
    Abstract: The use of fuel cells to produce electricity are known as an environmentally clean and reliable source of energy, and show promise as an automotive power source if the polymer electrolyte membrane fuel cell can be made less expensive, more durable, reduce or eliminate humidification of the reactive gases, and operate at temperatures encountered during automotive operating conditions. The use of an electro-catalyst formed from heteropoly acids immobilized by a conductive material, such as carbon or platinum black, and stabilizing a metallic black with the immobilized conductive material addressed these automotive fuel cell needs. Coating the fuel cell electrode, polymer electrolyte assembly with a nano-particle catalyst derived from a heteropoly acid provided anodic carbon monoxide tolerance at anodic overpotentials and an active cathodic oxygen reduction. The heteropoly acids can also function as supercapacitor electrode films.
    Type: Grant
    Filed: May 16, 2008
    Date of Patent: June 17, 2014
    Assignee: Colorado School of Mines
    Inventors: Ronald Justin Stanis, Andrew Michael Herring, Mei-Chen Kuo, Jack Richard Ferrell, III
  • Publication number: 20130217901
    Abstract: The invention relates to a method of producing optically active 4-chloro-3-hydroxybutanal compound (2) by reacting chloroacetaldehyde with aldehyde compound (1) in the presence of optically active pyrrolidine compound (5). wherein each symbol is as defined in the specification.
    Type: Application
    Filed: October 19, 2011
    Publication date: August 22, 2013
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventor: Yujiro Hayashi
  • Publication number: 20120277477
    Abstract: A method for manufacturing an acetal compound represented by the formula [1] in which the steps (A) to (D) as defined herein are performed sequentially, and an acetal compound of the formula [1] which is produced by the method: wherein n is 0 or 1 provided that R1 groups may be bonded or may not be bonded to each other when n is 0; R1 is an alkyl group having 1 or 2 carbon atoms or an alkylene group having 1 or 2 carbon atoms and the R1 groups may be same or different from each other; and R2 is an alkylene group having 1 or 6 carbon atoms.
    Type: Application
    Filed: March 23, 2012
    Publication date: November 1, 2012
    Applicant: NOF CORPORATION
    Inventors: Takashi Ichikawa, Shuichi Yoshimura, Ken-ichiro Nakamoto
  • Patent number: 8143455
    Abstract: What is described is a process for preparing 2-hydroxyacetals of the general formula in which R1 is hydrogen, a branched or unbranched C1-C12-alkyl radical, an electron-deficient, halogen-, NO2—, CN—, CF3—, acyl group- or branched or unbranched alkyl group-substituted or unsubstituted C5-C6-aryl or heteroaryl, and R2 is a branched or unbranched C1-C5-alkyl radical, or both R2 radicals are bonded directly to one another or to one another via a C1-C4 unit, by reacting an enol compound of the general formula (II) in which R3 is the same and R1 is as defined for formula (Ia), with bromine to give the corresponding dibromo adduct and then reacting this dibromo adduct with an alkoxide of the general formula (III) M-O—R2 (III) in which R2 is as defined for formula (Ia) and O is oxygen and M is lithium, sodium or potassium. What is likewise described is the preparation of the corresponding 2-hydroxyalkanals from the 2-hydroxyacetals thus obtained by acidic hydrolysis.
    Type: Grant
    Filed: June 11, 2008
    Date of Patent: March 27, 2012
    Assignee: SALTIGO GmbH
    Inventors: Thomas-Norbert Müller, Michael Dockner
  • Publication number: 20100280276
    Abstract: What is described is a process for preparing 2-hydroxyacetals of the general formula in which R1 is hydrogen, a branched or unbranched C1-C12-alkyl radical, an electron-deficient, halogen-, NO2—, CN—, CF3—, acyl group- or branched or unbranched alkyl group-substituted or unsubstituted C5-C6-aryl or heteroaryl, and R2 is a branched or unbranched C1-C5-alkyl radical, or both R2 radicals are bonded directly to one another or to one another via a C1-C4 unit, by reacting an enol compound of the general formula (II) in which R3 is the same and R1 is as defined for formula (Ia), with bromine to give the corresponding dibromo adduct and then reacting this dibromo adduct with an alkoxide of the general formula (III) M-O—R2 (III) in which R2 is as defined for formula (Ia) and O is oxygen and M is lithium, sodium or potassium. What is likewise described is the preparation of the corresponding 2-hydroxyalkanals from the 2-hydroxyacetals thus obtained by acidic hydrolysis.
    Type: Application
    Filed: June 11, 2008
    Publication date: November 4, 2010
    Applicant: SALTIGO GMBH
    Inventors: Thomas-Norbert Mueller, Michael Dockner
  • Publication number: 20090011969
    Abstract: The invention relates to a method for cleaning metal parts, according to which the metal parts are treated with a compound of the formula (1) wherein A represents (CH2)a or phenylene and R1, R2, R3 and R4 are identical or independently of one another represent C1 to C6-n-alkyl and/or isoalkyl and a represents a whole number from 0 to 4.
    Type: Application
    Filed: February 3, 2007
    Publication date: January 8, 2009
    Inventor: Frank-Peter Lang
  • Publication number: 20080207954
    Abstract: A process for preparing tri- and tetraoxymethylene glycol dimethyl ether (POMDMEn=3,4) by reacting formaldehyde with methanol and subsequently working up the reaction mixture by distillation, comprising the steps of: a) feeding aqueous formaldehyde solution and methanol into a reactor and reacting; b) feeding the reaction mixture a into a reactive evaporator and separating into a low boiler fraction b1 comprising formaldehyde, water, methanol, methylene glycol, polyoxymethylene glycols, hemiformals, methylal and polyoxymethylene glycol dimethyl ethers (POMDMEn>1), and a high boiler fraction b2, and recycling the high boiler fraction b2 into the reactor (step a)); c) feeding the low boiler fraction b1 into a first distillation column and separating into a low boiler fraction c1 comprising formaldehyde, water, methylene glycol, methanol, hemiformals, methylal, di-, tri- and tetraoxymethylene glycol dimethyl ether (POMDMEn=2,3,4), and a high boiler fraction c2, and recycling the high boiler fraction c2 into
    Type: Application
    Filed: June 12, 2006
    Publication date: August 28, 2008
    Applicant: BASF AKTIENGESELLSCHAFT
    Inventors: Eckhard Stroefer, Hans Hasse, Sergej Blagov
  • Patent number: 7211698
    Abstract: A process is proposed for distillatively working up an aqueous composition which comprises 1,1,2.2-tetramethoxyethane, glyoxal dimethyl acetal and methanol, wherein the workup of this composition is carried out in a dividing wall column to form low boiler, medium boiler and/or high boiler fractions, and a dividing wall is disposed in the longitudinal direction in the dividing wall column to form an upper common column region, a lower common column region, a feed section having rectifying section and stripping section and a withdrawal section having stripping section and rectifying section, and the aqueous composition is fed into the middle region of the feed section.
    Type: Grant
    Filed: September 3, 2004
    Date of Patent: May 1, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Gunnar Heydrich, Ingo Richter, Thomas Krug
  • Patent number: 6969776
    Abstract: The present invention provides a process whereby fluorinated ketones of various structures can be produced by short process steps and which is useful as an industrial production process.
    Type: Grant
    Filed: June 17, 2004
    Date of Patent: November 29, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
  • Patent number: 6956138
    Abstract: The present invention provides a method for obtaining a compound useful as a raw material for various fluororesins in high yield by a short process by using a starting material which is inexpensive and readily available.
    Type: Grant
    Filed: April 28, 2004
    Date of Patent: October 18, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Masahiro Ito, Daisuke Shirakawa, Masao Iwaya, Hidekazu Okamoto
  • Patent number: 6867332
    Abstract: A process is specified by which the xanthohumol present in hops can be isolated in high yield in an economical manner. In the process an ethanol pure resin extract is first extracted with a liquid or supercritical solvent in which the xanthohumol is insoluble and the resultant extraction residue is first washed with a first solvent mixture and then the extraction residue which has been washed with the first solvent mixture is, after removing the first solvent mixture, extracted with a second solvent mixture, the first solvent mixture having a higher polarity than the second solvent mixture. The hop extract produced from the second solvent mixture has a xanthohumol content of at least 85% by weight.
    Type: Grant
    Filed: July 23, 2003
    Date of Patent: March 15, 2005
    Assignee: Hallertauer Hopfenveredelungsgesellschaft m.b.H.
    Inventors: Martin Biendl, Hans Becker, Aslieh Nookandeh
  • Patent number: 6803488
    Abstract: The present invention provides a process whereby fluorinated ketones of various structures can be produced by short process steps and which is useful as an industrial production process.
    Type: Grant
    Filed: February 26, 2003
    Date of Patent: October 12, 2004
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
  • Patent number: 6747176
    Abstract: 2-Chloro-1,1,1-trialkoxyethane of formula (II): wherein R1 to R3, which may be the same or different, are alkyl, or any two of the alkyl groups taken together form a cyclic group, is prepared by reacting 1,1,1-trialkoxyethane with gaseous or liquid chlorine in the presence of alcohol solvent in an amount ranging from 0.1% to 20 wt %, based on the amount of 1,1,1-trialkoxyethane reactant.
    Type: Grant
    Filed: June 10, 2003
    Date of Patent: June 8, 2004
    Assignee: Degussa AG
    Inventors: Guenther Koehler, Karl-Heinz Bruehl, Johannes Ruwwe, Manfred Neumann
  • Patent number: 6660890
    Abstract: A process for the heterogeneous and enantioselective hydrogenation of prochiral organic &agr;-keto compounds with platinum as the catalyst in the presence of a soluble or immobilized chiral aromatic nitrogen base with at least one basic nitrogen atom adjacent to stereogenic carbon atoms, whereby prochiral &agr;-ketoacetals are hydrogenated to optically active &agr;-hydroxyacetals.
    Type: Grant
    Filed: December 19, 2001
    Date of Patent: December 9, 2003
    Assignee: Solvias AG
    Inventor: Martin Studer
  • Patent number: 6610892
    Abstract: The invention relates to a process for preparing 2,7-dimethyl-2,4,6-octatrienal monoacetals of the general formula I which comprises a) condensing an ester phosphonium salt of the general formula II or an ester phosphonate of the general formula III with an aldehyde of the formula IV in a Wittig or Wittig-Horner reaction to give an acetal ester of the general formula V b) reducing the ester of the formula V to give an acetal alcohol of the general formula VI and c) oxidizing the alcohol to 2,7-dimethyl-2,4,6-octatrienal monoacetals of the general formula I, where the substituents have the meaning defined in the description.
    Type: Grant
    Filed: March 12, 2002
    Date of Patent: August 26, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Hansgeorg Ernst, Klaus Henrich
  • Publication number: 20030069451
    Abstract: A process is described for preparing diacetals of glyoxal by reacting from 40 to 75% by weight aqueous glyoxal with monohydric alcohols in the presence of an acid catalyst, which comprises leaving a liquid mixture which, at the beginning of the reaction, comprises alcohol and glyoxal in a molar ratio of at least 15:1 and also water in a concentration of not more than 8% by weight in contact with the acid catalyst until concentration in the reaction mixture of the diacetal formed reaches at least 70% of the equilibrium concentration without more than 5% by weight of the alcohol used having already been distilled off.
    Type: Application
    Filed: October 3, 2002
    Publication date: April 10, 2003
    Inventors: Gunnar Heydrich, Nicola Christiane Aust, Hermann Putter, Andreas Fischer, Jorg Botzem
  • Publication number: 20020007089
    Abstract: A particularly useful process which includes the steps of providing a feedstream comprising methanol, a soluble condensation promoting component capable of activating a heterogeneous acidic catalyst and a source of formaldehyde formed by conversion of methanol in the presence of a catalyst comprising copper and zinc; and heating this feedstream with the heterogeneous acidic catalyst in a catalytic distillation column to convert methanol and formaldehyde present to methylal and higher polyoxymethylene dimethyl ethers and to separate the methylal from the higher polyoxymethylene dimethyl ethers is disclosed. Advantageously, methylal and higher polyoxymethylene dimethyl ethers are formed and separated in a catalytic distillation column. By including within the column a section containing an anion exchange resin, an essentially acid-free product is obtained.
    Type: Application
    Filed: July 11, 2001
    Publication date: January 17, 2002
    Inventors: Gary P. Hagen, Michael J. Spangler
  • Patent number: 5990360
    Abstract: A novel process for the manufacture of a .gamma.-halotiglic aldehyde HalH.sub.2 C-CH.dbd.C(CH.sub.3)-CHO [I], wherein Hal signifies chlorine or bromine, comprises haloalkoxylating a 1-alkoxy-2-methyl-1,3-butadiene H.sub.2 C.dbd.CH-C (CH.sub.3).dbd.CH-OR.sup.1 [II], wherein R.sup.1 signifies C.sub.1-4 -alkyl, using a particular halogenating agent in a C.sub.1-4 -alkanol (R.sup.2 OH) and hydrolyzing the thus-obtained .gamma.-halotiglic aldehyde dialkyl acetal HalH.sub.2 C-CH.dbd.C(CH.sub.3)-CH (OR.sup.1)(OR.sup.2) [III] to the desired .gamma.-chloro- or .gamma.-bromotiglic aldehyde I. The halogenating agent used in this process is selected from an alkali metal hypochlorite, an alkali metal hypobromite, an alkaline earth metal hypochlorite, an alkaline earth metal hypobromite, tert.butyl hypochlorite, N-bromoacetamide, 1.3-dichloro-5,5-dimethylhydantoin and 1,3-dibromo-5,5-dimethylhydantoin. Further aspects of the present invention are the use of the thus manufactured .gamma.
    Type: Grant
    Filed: May 12, 1998
    Date of Patent: November 23, 1999
    Assignee: Roche Vitamins Inc.
    Inventors: Bruno Burdet, Paul Nosberger, August Ruttimann
  • Patent number: 5892129
    Abstract: A process for the preparation of 1,1,3-trialkoxypropane by acid-catalyzed reaction of acrolein with a C.sub.1 to C.sub.6 alcohol, which can be carried out well on a large scale and leads to a higher selectivity. The process involves (a) the reaction, in the presence of a solid acid catalyst which is insoluble in the reaction mixture, (b) a partial neutralization of the reaction mixture, using an amine or basic ion exchanger, and (c) specific recovery by distillation of the reaction mixture and recirculation of fractions containing useful materials; aqueous fractions containing recyclable useful materials are largely dehydrated by pervaporation prior to being recirculated.
    Type: Grant
    Filed: May 21, 1997
    Date of Patent: April 6, 1999
    Assignee: Degussa Aktiengesellschaft
    Inventors: Mathias Hoepp, Dietrich Arntz, Hans-Peter Ohlinger, Willi Hofen
  • Patent number: 5739394
    Abstract: The invention relates to novel 3,3-dioxy-4,4,4-trifluorobutyric acid derivatives of the formula (I) ##STR1## in which R.sup.1 and R.sup.2 independently of one another represent C.sub.1 -C.sub.10 -alkyl, or represent cyclohexyl, or represent optionally substituted C.sub.6 -C.sub.10 -aryl or C.sub.7 -C.sub.14 -arylalkyl, orR.sup.1 and R.sup.2 together represent C.sub.2 -C.sub.4 -alkylene which is optionally mono- or disubstituted by methyl, or optionally substituted ortho-arylene,R.sup.3 represents hydrogen or C.sub.1 -C.sub.10 -alkyl, or represents cycloalkyl, or represents optionally substituted C.sub.6 -C.sub.10 -aryl or C.sub.7 -C.sub.
    Type: Grant
    Filed: December 16, 1996
    Date of Patent: April 14, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventor: Norbert Lui
  • Patent number: 5449836
    Abstract: A process for the preparation of vitamin A which preferably comprises bringing cyclogeranyl sulphone into contact with a C.sub.10 aldehyde acetal, halogenating the derivative obtained and then removing the halogen group and the sulphone, removing the acetal group and isomerizing the retinal obtained to the desired configuration. Also disclosed are compounds useful as intermediates in the synthesis of vitamin A and processes for preparation of these intermediate compounds.
    Type: Grant
    Filed: January 5, 1995
    Date of Patent: September 12, 1995
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventor: Pierre Chabardes
  • Patent number: 5269955
    Abstract: Disclosed is a lubricating oil for compression-type refrigerators comprising, as a main component, a polyoxyalkylene glycol derivative which has at least one constitutional unit represented by the general formula: ##STR1## wherein R.sup.1 to R.sup.4 are as defined in the specification. Said lubricating oil for compression-type refrigerators has good miscibility with refrigerants including R-134a.
    Type: Grant
    Filed: May 2, 1990
    Date of Patent: December 14, 1993
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Yasuhiro Kawaguchi, Nobuaki Shimizu, Masato Kaneko
  • Patent number: 5233063
    Abstract: The present invention relates to pentanedioic acid derivatives. The present invention further relates to pharmaceutical compositions containing such compounds and the use of such compounds and compositions as hypolipidemic drugs.
    Type: Grant
    Filed: January 16, 1991
    Date of Patent: August 3, 1993
    Assignee: G. D. Searle & Co.
    Inventors: John S. Baran, Harman S. Lowrie
  • Patent number: 5206443
    Abstract: Alkanediol bisacetals useful as surface-active substances for industrial purposes, in particular in washing and cleaning agents, have the formula I ##STR1## where R.sup.1 is alkyl or alkenyl of from 6 to 30 carbon atoms,A is 1,2-alkylene of from 2 to 4 carbon atoms,m is from 0 to 50,within each of the pairs R.sup.1, A and m the meanings being identical or different, andn is from 2 to 20.
    Type: Grant
    Filed: April 20, 1992
    Date of Patent: April 27, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Richard Baur, Helmut Guembel, Alfred Oftring, Johannes Perner, Gerhard Wolf
  • Patent number: 5202480
    Abstract: This invention pertains to perfluoropolyethers and perhalogenated chlorofluoroether polymers that can be prepared by fluorinating polymers made by the polymerization of acetals, ketals, polyacetals, polyketals and orthoesters with elemental fluorine.
    Type: Grant
    Filed: August 30, 1991
    Date of Patent: April 13, 1993
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5191127
    Abstract: This invention provides glyoxal derivatives and a method for making these derivatives. A particularly useful derivative, 1-chloro-1,2,2-trialkoxyethane, and a facile method for making these alpha-halo ethers are provided. The alpha-halo ethers are valuable intermediates in the manufacture of a variety of commercial compounds.
    Type: Grant
    Filed: August 13, 1991
    Date of Patent: March 2, 1993
    Assignee: Loyola University of Chicago
    Inventor: James H. Babler
  • Patent number: 5030765
    Abstract: The present invention is concerned with novel tetrahydronaphthalene and indane derivatives of the formula ##STR1## useful as for combatting dermatoses as well as neoplasmas.
    Type: Grant
    Filed: October 16, 1990
    Date of Patent: July 9, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Loeliger, Peter Mohr, Ekkehard Weiss
  • Patent number: 5025093
    Abstract: A method of breaking down perfluoropolyethers into lower molecular weight fragments by pyrolysis is disclosed. The perfluoropolyethers are pyrolyzed generally at above about 350.degree. C. Volatile lower molecular weight components are condensed and collected. Various molecular weight fractions and collected. Various molecular weight fractions can be obtained by taking appropriate distillation cuts.
    Type: Grant
    Filed: January 5, 1990
    Date of Patent: June 18, 1991
    Assignee: Exfluor Research Corporation
    Inventors: Richard J. Lagow, Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu M. Kawa
  • Patent number: 4996375
    Abstract: Novel methyl carbinol derivatives of Vitamin E and a method for their manufacture.
    Type: Grant
    Filed: April 24, 1989
    Date of Patent: February 26, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Barner, Josef Hubscher
  • Patent number: 4947005
    Abstract: 1,1,2-Trialkoxyethanes of the general formula I ##STR1## where R.sup.1 to R.sup.3 are each independently of the others C.sub.1 -C.sub.20 -alkyl or cycloalkyl, or R.sup.1 and R.sup.2 may be linked together to form a 5-, 6- or 7-membered ring, are prepared by reacting formaldehyde dialkyl acetals of the general formula II ##STR2## where R.sup.1 and R.sup.2 are each as defined above, or compounds which are capable of forming formaldehyde dialkyl acetals under the reaction conditions, with carbon monoxide, hydrogen and alkanols R.sup.3 OH under superatmospheric pressure at elevated temperature in the presence of a catalyst composed of a cobalt carbonyl compound and a promotor, wherein the promotor is an alkali metal, alkaline earth metal or ammonium salt of a protogenic compound having an acid constant K.sub.a of from 10.sup.-2 to 10.sup.-14, an alkali metal or alkaline earth metal hydroxide or an aminocarboxylic acid.
    Type: Grant
    Filed: August 25, 1989
    Date of Patent: August 7, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Koeffer, Werner Bertleff
  • Patent number: 4894484
    Abstract: A method of breaking down perfluoropolyethers into lower molecular weight fragments by pyrolysis is disclosed. The perfluoropolyethers are pyrolyzed generally at above about 350.degree. C. Volatile lower molecular weight components are condensed and collected. Various molecular weight fractions can be obtained by taking appropriate distillation cuts.
    Type: Grant
    Filed: September 3, 1987
    Date of Patent: January 16, 1990
    Assignee: Exfluor Research Corporation
    Inventors: Richard J. Lagow, Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu M. Kawa
  • Patent number: 4851585
    Abstract: Novel methyl carbinol derivatives of Vitamin E and a method for their manufacture.
    Type: Grant
    Filed: November 12, 1987
    Date of Patent: July 25, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Barner, Josef Hubscher
  • Patent number: 4835320
    Abstract: This process for the preparation of products of general formula (I): ##STR1## wherein either R.sub.1 and R.sub.2, which are identical, represent a --CHRR.sub.3 group, in which R and R.sub.3, which are identical or different, represent an alkyl, alkenyl or aralkyl group, or R.sub.1 and R.sub.2, which are identical, represent a --CH.sub.2 R group, in which R represents a hydrogen atom, an alkyl, alkenyl or aralkyl radical, or R.sub.1 and R.sub.2 together form a --CH.sub.2 --(CRR).sub.n --CHR-- radical, in which n represents 0 or 1 and R retains the meaning given previously, is characterized by reacting glyoxal in the presence of an acid catalyst with an excess of the corresponding alcohol of general formula (II) RR.sub.3 CHOH, (III) RCH.sub.2 OH or (IV) --(CRR).sub.n --CHROH, in which R, R.sub.3 and n retain the meaning given previously, then stopping the reaction as soon as the concentration of the desired monoacetal of general formula (I) decreases in the reaction medium in favor of bisacetal.
    Type: Grant
    Filed: June 1, 1987
    Date of Patent: May 30, 1989
    Assignee: Societe Francaise Hoechst
    Inventors: Alain Blanc, Farid Hamedi-Sangsari, Francine J. Chastrette
  • Patent number: 4755625
    Abstract: 1,1,2-trialkoxyethanes I ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each C.sub.1 -C.sub.8 -alkyl and R.sup.1 and R.sup.2 may furthermore be bonded to one another to form a 5-membered to 7-membered ring, are prepared by reacting a formaldehyde dialkyl acetal II with carbon monoxide and hydrogen, from 0.5 to 1.5 moles of hydrogen being used per mole of carbon monoxide, and with not less than 1 mole of alcohol R.sup.3 OH per mole of formaldehyde dialkyl acetal under superatmospheric pressure and at elevated temperatures in the presence of a catalyst which is formed from a cobalt carbonyl compound and a trivalent organic compound of the formula III ##STR2## where A is phosphorus, arsenic, antimony or bismuth and R.sup.4, R.sup.5 and R.sup.6 are each an organic radical.
    Type: Grant
    Filed: July 16, 1987
    Date of Patent: July 5, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Robert Maerkl, Werner Bertleff, Rudolf Kummer
  • Patent number: 4743401
    Abstract: A process for converting an allylic ether to its corresponding acetal is disclosed. In this process an allylic ether is contacted with an organic hydroxy compound and a catalytically effective amount of a cobalt compound to produce the corresponding acetal.
    Type: Grant
    Filed: October 3, 1986
    Date of Patent: May 10, 1988
    Assignee: National Distillers and Chemical Corporation
    Inventors: Biau-Hung Chang, Ronnie M. Hanes
  • Patent number: 4658044
    Abstract: Compounds of formula (C) ##STR1## where either R.sup.D represents a hydroxymethyl group and R.sup.E represents a hydroxyl group or R.sup.D represents a protected hydroxymethyl group and R.sup.E represents a protected hydroxyl group or R.sup.E represents a hydroxyl group and R.sup.D represents an ethenyl group and R.sup.F represents a hydroxyl or protected hydroxyl group or a leaving group with the proviso that either R.sup.D represents a protected hydroxymethyl group and R.sup.E represents a protected hydroxyl group or R.sup.F represents a protected hydroxyl group, which compounds are of use as intermediates in the preparation of compounds having antiviral activity.
    Type: Grant
    Filed: October 24, 1985
    Date of Patent: April 14, 1987
    Assignee: Glaxo Group Limited
    Inventor: Paul Ravenscroft
  • Patent number: 4536585
    Abstract: It is disclosed that a Pd-Tl alloy catalyst is used in making acetals and acetalic ethers from alcohols and saturated or unsaturated aldehydes, and to make cyclic acetals and cyclic acetalic ethers when reacting with diols.
    Type: Grant
    Filed: December 5, 1983
    Date of Patent: August 20, 1985
    Assignee: The Standard Oil Company
    Inventors: Christos Paparizos, Robert S. Shout, Wilfrid G. Shaw
  • Patent number: 4513144
    Abstract: Trioxane and other acetals are purified by contacting with an alkali metal superoxide, then isolated in a purified form. Optionally, a phase transfer catalyst can be utilized in the purification. Recovered acetals are sufficiently pure for polymerization to high molecular weight.
    Type: Grant
    Filed: November 3, 1982
    Date of Patent: April 23, 1985
    Assignee: Conoco Inc.
    Inventor: Jeff T. Fenton
  • Patent number: 4460767
    Abstract: A process is disclosed for production of a sugar ketal, which comprises reacting a sugar with a ketone in the presence of (A) (1) copper, or an oxide, hydroxide or salt thereof and (2) hydrogen chloride or hydrogen bromide, or (B) cupric chloride or cupric bromide, said catalyst system being very effective in a small amount. The formation of unfavorable by-products can be reduced to a trace amount. The process offers the objective ketal in improved yields, and an industrially advantageous process.
    Type: Grant
    Filed: September 15, 1982
    Date of Patent: July 17, 1984
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Koichi Matsumura, Tetsuya Aono
  • Patent number: 4418217
    Abstract: A process for the production of a mixed formal of polyglycol ethers having formulae selected from the group consisting of ##STR1## wherein R.sup.1 is a straight or branched chain alkyl having from 1 to 18 carbon atoms, and R.sup.2 is selected from the group consisting of hydrogen and straight or branched chain alkyl having from 1 to 17 carbon atoms, where the sum of the carbon atoms in R.sup.1 plus R.sup.2 is from 6 to 18, R.sup.3 is a member selected from the group consisting of monoalkylphenyl having from 14 to 26 carbon atoms, dialkylphenyl having from 14 to 26 carbon atoms, trialkylphenyl having from 14 to 26 carbon atoms, a straight or branched chain alkyl having from 8 to 22 carbon atoms, a straight or branched chain alkenyl having from 8 to 22 carbon atoms, and a radical having the formula ##STR2## wherein R.sup.1 and R.sup.2 have the above assigned values, and R.sup.
    Type: Grant
    Filed: April 27, 1981
    Date of Patent: November 29, 1983
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Karl Schmid, Margarete Grunert, Jochen Heidrich, Holger Tesmann
  • Patent number: 4374999
    Abstract: Acrolein acetals are selectively hydroformylated on the unsaturated carbon atom adjacent to the carbon bearing two ether groups in the presence of a supported rhodium-cobalt bimetallic cluster. The resulting internally hydroformylated product is useful as a precursor of methacrylic acid.
    Type: Grant
    Filed: January 2, 1981
    Date of Patent: February 22, 1983
    Assignee: The Dow Chemical Company
    Inventor: Philip E. Garrou
  • Patent number: 4313008
    Abstract: The S-enantiomer of 3-chloro-1,2-propanediol is prepared by reaction of a chlorodeoxy-D-saccharide having the partial structure. ##STR1## to cleave the glycol, reduce the aldehyde so formed to an alcohol, and hydrolyse the alcohol under mild acidic conditions.
    Type: Grant
    Filed: May 17, 1979
    Date of Patent: January 26, 1982
    Assignee: Tate & Lyle Ltd.
    Inventor: Haydn F. Jones
  • Patent number: 4304927
    Abstract: Compounds of the structure ##STR1## wherein X is --F or Cl and each R is independently --H, --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 CH.sub.3, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 or M where M is an alkali metal, an alkaline earth metal, ammonium or a quaternary ammonium are disclosed. The above compounds are prepared by treating a compound of the structure ##STR2## where each R.sup.1 is independently --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 CH.sub.3 or --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 ; or ##STR3## with a strong protic acid, followed, as desired, by base hydrolysis to form carboxylate salts (R.dbd.M).
    Type: Grant
    Filed: November 11, 1977
    Date of Patent: December 8, 1981
    Assignee: E. I. DuPont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 4301090
    Abstract: Oxygenated organic compounds, e.g. esters, aldehydes, and amides, are prepared by reacting an olefinically unsaturated compound with carbon monoxide and a compound containing a replaceable hydrogen atom in the presence of a catalyst comprising cobalt carbonyl and a polyamine promoter ligand. These reactions are carried out under relatively mild conditions of temperature and pressure.
    Type: Grant
    Filed: August 13, 1979
    Date of Patent: November 17, 1981
    Assignee: Standard Oil Company
    Inventors: Frederick A. Pesa, Thomas A. Haase
  • Patent number: 4280011
    Abstract: The use of acetals as aldehyde generators in foodstuff applications is disclosed.
    Type: Grant
    Filed: April 5, 1978
    Date of Patent: July 21, 1981
    Assignee: Hercules Incorporated
    Inventor: Robert S. DeSimone