Oxy Containing Patents (Class 568/496)
  • Patent number: 9796649
    Abstract: A process for reducing the percentage by weight of formaldehyde present in a composition comprising glycolaldehyde, wherein formaldehyde is transformed into one or more formaldehyde acetal(s) and removed from the reactive distillation reaction solution by reactive distillation in the presence of at least one alcohol and a catalyst.
    Type: Grant
    Filed: February 25, 2014
    Date of Patent: October 24, 2017
    Assignee: Haldor Topsoe A/S
    Inventors: Esben Taarning, Martin Spangsberg Holm
  • Patent number: 8945534
    Abstract: Methods for the controlled activation of the reuterin-production machinery of Lactobacillus reuteri by adding glycerol and other substances during the manufacture of cell-cultures and keeping the produced reuterin in the bacterial cell during preservation and storage. In particular this invention relates to the manufacture of large amounts of L. reuteri that are loaded with reuterin, and the use of such loaded bacteria for applications such as prevention and treatment of diseases, for food applications and the like.
    Type: Grant
    Filed: November 4, 2013
    Date of Patent: February 3, 2015
    Assignee: BioGaia AB
    Inventor: Stefan Roos
  • Publication number: 20140371417
    Abstract: The invention provides non-naturally occurring microbial organisms having a 4-hydroxybutyrate, gamma-butyrolactone, 1,4-butanediol, 4-hydroxybutanal, 4-hydroxybutyryl-CoA and/or putrescine pathway and being capable of producing 4-hydroxybutyrate, wherein the microbial organism comprises one or more genetic modifications. The invention additionally provides methods of producing 4-hydroxybutyrate, gamma-butyrolactone, 1,4-butanediol, 4-hydroxybutanal, 4-hydroxybutyryl-CoA and/or putrescine or related products using the microbial organisms.
    Type: Application
    Filed: April 25, 2014
    Publication date: December 18, 2014
    Applicant: Genomatica, Inc.
    Inventors: Priti PHARKYA, Anthony P. BURGARD, Stephen J. VAN DIEN, Robin E. OSTERHOUT, Mark J. BURK, John D. TRAWICK, Michael P. KUCKINSKAS, Brian STEER
  • Publication number: 20140357547
    Abstract: A process of forming methoxymelonal comprising the steps of treating a solution of citronellene to ozonolysis, and hydrogenating the product formed to provide methoxymelonal.
    Type: Application
    Filed: October 11, 2012
    Publication date: December 4, 2014
    Inventors: Andreas Goeke, Yue Zou
  • Publication number: 20140271537
    Abstract: The present invention generally relates to deuterium-enriched aldehydes, compositions comprising deuterium-enriched aldehydes, and methods for slowing the rate of aldehyde autoxidation. In one aspect, the present invention provides a composition comprising a compound of structure 1: wherein: there are at least 6×1018 molecules of the aldehyde and Rx is hydrogen, wherein the deuterium isotope in Rx is in an amount greater than 0.10 percent of the hydrogen atoms present in Rx.
    Type: Application
    Filed: March 15, 2014
    Publication date: September 18, 2014
    Inventor: Anthony W. Czarnik
  • Patent number: 8680200
    Abstract: Novel polyglycerol aldehyde polymers are described. The polymers comprise glycerol monomers connected by ether linkages and have 3 to about 170 aldehyde groups per molecule. The polyglycerol aldehydes may be reacted with various amine-containing polymers to form hydrogel tissue adhesives and sealants that may be useful for medical applications such as wound closure, supplementing or replacing sutures or staples in internal surgical procedures such as intestinal anastomosis and vascular anastomosis, tissue repair, preventing leakage of fluids such as blood, bile, gastrointestinal fluid and cerebrospinal fluid, ophthalmic procedures, drug delivery, and preventing post-surgical adhesions.
    Type: Grant
    Filed: March 26, 2010
    Date of Patent: March 25, 2014
    Assignee: Actamax Surgical Materials LLC
    Inventor: Henry Keith Chenault
  • Publication number: 20140057992
    Abstract: Methods for the controlled activation of the reuterin-production machinery of Lactobacillus reuteri by adding glycerol and other substances during the manufacture of cell-cultures and keeping the produced reuterm in the bacterial cell during preservation and storage, in particular this invention relates to the manufacture of large amounts of L. reuteri that are loaded with reuterm, and the use of such loaded bacteria for applications such as prevention and treatment of diseases, for food applications and the like.
    Type: Application
    Filed: November 4, 2013
    Publication date: February 27, 2014
    Inventor: Stefan Roos
  • Publication number: 20130216492
    Abstract: Provided are a method for searching for a malodor inhibitor by using the response of an olfactory receptor as an indicator; a method for inhibiting malodor based on the antagonism of olfactory receptors; and a malodor inhibitor. Disclosed are a method for searching for a malodor inhibitor, the method including: adding a test substance and a malodor-causing substance to any one olfactory receptor selected from the group consisting of OR51E1, OR2W1, OR10A6, OR51I2, and OR51L1, measuring the response of the olfactory receptor to the malodor-causing substance, identifying the test substance that suppresses the response of the olfactory receptor on the basis of the measured response, and selecting the identified test substance as a malodor inhibitor; an antagonist to any one olfactory receptor selected from the group consisting of OR51E1, OR2W1, OR10A6, OR51I2, and OR51L1; a method for inhibiting malodor using the antagonist.
    Type: Application
    Filed: September 1, 2011
    Publication date: August 22, 2013
    Applicant: KAO CORPORATION
    Inventors: Aya Kato, Naoko Saito, Etsuji Wakisaka
  • Publication number: 20130190518
    Abstract: The present invention relates to a process for preparing a terpenoid derivative, the process comprising a metathesis of an olefin and a terpenoid, and to terpenoid derivatives prepared with said process.
    Type: Application
    Filed: July 11, 2011
    Publication date: July 25, 2013
    Applicant: Ecole Nationale Superieure de Chimie de Rennes
    Inventors: Marc Mauduit, Frédéric Caijo, Christophe Crévisy
  • Publication number: 20120252902
    Abstract: A method is provided for treating a subject in need of therapy for attention deficit hyperactivity disorder (ADHD) and related CNS disorder symptoms of impaired learning, impaired planning, impaired problem solving, impulsiveness attention deficit and aggression comprising administering to said subject an amount of a ketogenic material sufficient to produce a ketosis in the subject sufficient to provide therapeutic benefit in such behavioural disorders. Preferred materials produce a ketosis is such that the total concentration of acetoacetate and (R)-3-hydroxybutyrate in the blood of the subject is raised to between 0.1 and 30 mM.
    Type: Application
    Filed: May 29, 2012
    Publication date: October 4, 2012
    Applicant: BTG International Limited
    Inventors: Keith Frank Martin, David John Heal
  • Patent number: 7951977
    Abstract: The present invention provides; a process for producing a compound (IV) comprising a step of reacting a compound (I) with a compound (II) in the presence of an optionally substituted cyclic secondary amine to obtain a compound (III) and a step of sequentially or simultaneously eliminating R1 and R2 from the compound (III), and then cyclizing the R1- and R2-eliminated compound to obtain the compound represented by the formula (IV); a process for producing a high purity compound (IV); an intermediate thereof; and a process for producing an intermediate.
    Type: Grant
    Filed: June 5, 2006
    Date of Patent: May 31, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tetsuya Ikemoto, Yosuke Watanabe
  • Patent number: 7943625
    Abstract: The present invention relates to a compound according to Formula (I) wherein R1 is selected from C1-C6 alkyl, and said C1-C6 alkyl is substituted with C1-C6 alkoxy; and at least one of said C1-C6 alkyl or said C1-C6 alkoxy is branched; or a pharmaceutically acceptable salt thereof, solvate or solvate of a salt thereof, as well as, to compositions containing at least one compound according to Formula (I) and methods of treating at least one disease or condition therewith.
    Type: Grant
    Filed: June 1, 2007
    Date of Patent: May 17, 2011
    Assignee: AstraZeneca AB
    Inventor: Anna-Karin Tidén
  • Patent number: 7872152
    Abstract: The present invention is generally drawn to novel isolated therapeutic agents, termed resolving, generated from the interaction between a dietary omega-3 polyunsaturated fatty acid (PUFA) such as eicosapentaenoic acid (EPA) or docosahexaenoic acid (DHA), cyclooxygenase-II (COX-2) and an analgesic, such as aspirin (ASA). Surprisingly, careful isolation of compounds generated from the combination of components in an appropriate environment provide di- and tri-hydroxy EPA or DHA compounds having unique structural and physiological properties. The present invention therefore provides for many new useful therapeutic di- or tri-hydroxy derivatives of EPA or DHA (resolvins) that diminish, prevent, or eliminate inflammation or PMN migration, for example. The present invention also provides methods of use, methods of preparation, and packaged pharmaceuticals for use as medicaments for the compounds disclosed throughout the specification.
    Type: Grant
    Filed: August 9, 2007
    Date of Patent: January 18, 2011
    Assignee: The Brigham and Women's Hospital, Inc.
    Inventors: Charles N. Serhan, Bruce D. Levy
  • Patent number: 7842842
    Abstract: Disclosed are new chemical entities 2, 3, 7-trimethyl-7-alkoxy-octanals, represented by the general structure (STR#GEN) wherein “R” represents an alkyl, allyl, alkenyl, or aryl alkyl groups. In specific the present invention discloses novel hydro-alkoxyl citronellal compounds represented by STR#I, II and III to generate new flavor and/or aroma materials. The use of compounds of the present invention as a part of perfume and aroma (fragrance) compositions is also disclosed by the invention.
    Type: Grant
    Filed: August 19, 2009
    Date of Patent: November 30, 2010
    Assignee: Sami Labs Ltd.
    Inventors: Muhammed Majeed, Kalyanam Nagabhushanam, Sakthivel Palaniappan, Ambady Rajagopalan, Rajasekharan Parthasarathy, Kiran Trineshwaraiah-Sirsalmath
  • Publication number: 20100234644
    Abstract: Aldehyde and ketone reactants are converted to hydroxyaldehydes, polyhydroxyaldehydes, hydroxyketones and/or polyhydroxyketones in liquid phase by an aldol condensation process where a selected product carbon chain length is produced using specific concentrations of soluble inorganic base at sub-ambient temperature.
    Type: Application
    Filed: March 10, 2009
    Publication date: September 16, 2010
    Applicant: Carter Technologies
    Inventor: Melvin K. Carter
  • Publication number: 20100185017
    Abstract: Methods, enzymes, recombinant microorganism, and microbial systems are provided for converting suitable monosaccharides or oligosaccharides, such as those derived from biomass, as well as various aldehydes and/or ketones, into commodity chemicals, such as biofuels. Commodity chemicals produced by the methods described herein are also provided. Commodity chemical enriched, refinery-produced petroleum products are also provided, as well as methods for producing the same.
    Type: Application
    Filed: December 11, 2009
    Publication date: July 22, 2010
    Inventors: Yasuo Yoshikuni, Adam J. Wargacki, Asael Herman
  • Publication number: 20100132249
    Abstract: A perfume composition including at least one compound having the formula: wherein p, q and r are independently selected from 0 and 1, p+q+r being from 0-3 and X1 is saturated or unsaturated, such that: (a) when p+q+r=0, R1, R2 and R12 are Me; R3-5 and R9-11 are H; (b) when p+q+r=1, R1 and R12 are independently selected from H, Me and Et; R2 is selected from H and C1-C4 alkyl; R3-5 and R9 are independently selected from H and methyl; and R8 and R10 are H; (c) when p+q+r=2, R1 and R2 are selected from H and C1-C4 alkyl, R3 and R9-12 are independently selected from H and methyl: R4-5 are H, or R4 and R5 together form a methylene group; and R6-7 are H; (d) when p+q+r=3, R1, R2 and R12 are Me; and R3-11 are H.
    Type: Application
    Filed: January 31, 2008
    Publication date: June 3, 2010
    Inventors: Hai-Shan Dang, Simon Ellwood, Anne-Dominique Fortineau, Christopher Furniss
  • Patent number: 7582799
    Abstract: The present invention provides an industrially advantageous process for producing hydrazone derivative represented by the formula (5), which is shown by the following reaction formula.
    Type: Grant
    Filed: April 27, 2006
    Date of Patent: September 1, 2009
    Assignees: Shiratori Pharmaceutical Co., Ltd., Asubio Pharma Co., Ltd.
    Inventors: Hiroshi Yoshino, Kentaro Kobayashi, Yuichi Shiro
  • Publication number: 20080319088
    Abstract: The present invention is directed to the novel aldehyde compounds, represented by the general structure of Formula I set forth below: wherein R is a straight, branched hydrocarbon moiety consisting of 3 to 10 carbon atoms and may contain one or more oxygen heteroatom.
    Type: Application
    Filed: June 20, 2007
    Publication date: December 25, 2008
    Inventors: Catherine Marie Smith, Richard M. Boden
  • Publication number: 20080261860
    Abstract: 6-Methoxy-2,6-dimethyloctanal, a method of its production and fragrance compositions comprising it.
    Type: Application
    Filed: September 15, 2006
    Publication date: October 23, 2008
    Applicant: GIVAUDAN SA
    Inventor: Urs Mueller
  • Patent number: 7126030
    Abstract: In the method of the invention, hydroxypivalaldehyde (3-hydroxy-2,2-dimethylpropanal) and/or its dimer is stored under solid conditions containing an amount of water. By storing such solid conditions, hydroxypivalaldehyde and/or its dimer is stored for a long period of time without reducing its purity.
    Type: Grant
    Filed: February 24, 2005
    Date of Patent: October 24, 2006
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Yoshihiro Shiokawa, Hiroaki Shigeta, Ikutaro Kuzuhara
  • Patent number: 7094932
    Abstract: The present invention provides a method for the production of glycolaldehyde with high specificity. The hydrous thermolysis consists of the spraying of aqueous sugar solutions containing from 25 to 80% of water but preferably 30 to 60% water, as a fine mist into a reactor held at the between 500 and 600° C., but preferably between 520 and 560° C. and the condensation of the resulting vaporous product in a surface condenser with optional heat recovery. The residence time of the vaporous product in the reactor should be in the range 0.1–5 seconds, but preferably in the range 0.5 to 2 seconds. Aldose monomeric sugars, preferably glucose (also known as dextrose), are preferred for use in the aqueous solution. The yield of glycolaldehyde in the condensed liquid is minimum 50% by weight of the sugar fed for glucose solutions.
    Type: Grant
    Filed: November 8, 2001
    Date of Patent: August 22, 2006
    Assignee: Resource Transforms International Ltd.
    Inventors: Piotr A. Majerski, Jan K. Piskorz, Desmond St. A. G. Radlein
  • Patent number: 6911566
    Abstract: A process for producing 1,3-propanediol, comprising: hydrating acrolein in a liquid phase in the presence of a hydration catalyst to form 3-hydroxypropanal; separating any unreacted acrolein, if any is present; and carrying out catalytic hydrogenation of the 3-hydroxypropanal in a liquid or gas phase with a hydrogenation catalyst, wherein the hydration catalyst is a catalyst comprising at least one member selected from the group consisting of the following materials (a) to (c) and has a pH of 6 or less at 20° C., when made into a slurry by dispersing the catalyst in a quantity of water 5 times as much as the quantity of catalyst by weight: (a) a metalloaluminophosphate molecular sieve, (b) an FER type zeolite, and (c) an oxide or compound oxide, excluding crystalline aluminosilicate zeolites, which comprises one or more element(s) selected from the elements belonging to group 4, group 13 and group 14 of the periodic table.
    Type: Grant
    Filed: March 1, 2002
    Date of Patent: June 28, 2005
    Assignee: Asahi Kasei Kabushiki Kaisha
    Inventors: Takashi Tsunoda, Kouji Nomura
  • Patent number: 6525227
    Abstract: A reaction method by a novel Lewis acid catalyst stable in water for organic synthesis by using a metal compound stable in water and functioning as a Lewis acid catalyst and using water as apart or all of a solvent, the metal ion of the metal compound having a hydrolysis constant (pKh) of: 4.3≦pKh≦10.1 and a water exchange rate constant (WERC) of 3.2×106M−1sec−1 or more.
    Type: Grant
    Filed: April 4, 2001
    Date of Patent: February 25, 2003
    Assignee: Japan Science and Technology Corporation
    Inventor: Shu Kobayashi
  • Patent number: 6320084
    Abstract: The invention pertains to a process for the preparation of glyceraldehyde, or an acetal or a hemiacetal thereof, characterized in that 3-butene-1,2-diol is dissolved in a lower alkanol and is subjected to ozonolysis to obtain a 3-hydroperoxy-3-alkoxy-propane-1,2-diol, which is subjected to a reductive treatment to obtain a hemiacetal of glyceraldehyde, which optionally may be converted into glyceraldehyde or an acetal or hemiacetal thereof, and to a process wherein the hemiacetal of glyceraldehyde is converted to a 3-aminopropane-1,2-diol derivative, by subjecting the hemiacetal of glyceraldehyde to a reductive treatment in the presence of ammonia or a primary or secondary amine.
    Type: Grant
    Filed: February 26, 2001
    Date of Patent: November 20, 2001
    Assignee: Akzo Nobel NV
    Inventors: Ulrich Wecker, Manfred Josef Bergfeld
  • Patent number: 6262277
    Abstract: Provided are novel benzothiepines, derivatives, and analogs thereof; pharmaceutical compositions containing them; and methods of using these compounds and compositions in medicine, particularly in the prophylaxis and treatment of hyperlipidemic conditions such as those associated with atherosclerosis or hypercholesterolemia, in mammals.
    Type: Grant
    Filed: November 19, 1999
    Date of Patent: July 17, 2001
    Assignee: G.D. Searle and Company
    Inventors: Len F. Lee, Shyamal C. Banerjee, Horng-Chih Huang, Jinglin J. Li, Raymond E. Miller, David B. Reitz, Samuel J. Tremont
  • Patent number: 5962745
    Abstract: A process for preparing 3-hydroxyalkanals having 3 to 12 carbon atoms by hydration of 2-alkenals with homogeneous catalysis, by using as catalyst a compound corresponding to the formula ##STR1## wherein: z denotes H, C.sub.1 - to C.sub.6 -alkyl, --CH.sub.2 --CH(CH.sub.3) --Y' or --(CH.sub.2).sub.o --Y'R denotes H, C.sub.1 - to C.sub.6 -alkyl, benzyl, phenyl, .omega.-hydroxy --C.sub.1 - to C.sub.6 -alkyl, --CH.sub.2 --CH(CH.sub.3)--Y' or --(CH.sub.2).sub.o --Y'Y and Y' are identical or different and denote --COOH, --P(O) (OH).sub.2, --OH, pyridyl, or --P(O) (CH.sub.2 OH)OH, wherein the acid functional group may be present partly in the form of its alkali metal salt, alkaline-earth salt or ammonium saltn denotes 1, 2, 3, 4, 5 or 6 where Y is --COOH, --P(O) (OH).sub.2, pyridyl or --P(O) (CH.sub.2 OH) OH; 2 or 3 where Y is --OHo denotes 1, 2, 3, 4, 5 or 6 where Y' is --COOH, --P(O) (OH).sub.2, pyridyl or --P(O) (CH.sub.2 OH)OH; 0, 2 or 3 where Y' is --OH.
    Type: Grant
    Filed: February 11, 1998
    Date of Patent: October 5, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Christoph Brossmer, Dietrich Arntz
  • Patent number: 5731478
    Abstract: An alkanediol such as 1,3-propanediol is prepared in a process which involves reacting an alkylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of a non-phosphine-ligated cobalt or rhodium catalyst and a manganese porphyrine promoter to produce an intermediate product mixture containing a hydroxyalkanal in an amount less than 15 wt %; extracting the hydroxyalkanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100.degree. C. and separating the aqueous phase containing hydroxyalkanal from the organic phase containing cobalt catalyst; hydrogenating the hydroxyalkanal in the aqueous phase to an alkanediol; and recovering the alkanediol.The process enables the production of an alkanediol such as 1,3-propanediol in high yields and selectivity without the use of a phosphine ligand with the cobalt or rhodium catalyst.
    Type: Grant
    Filed: October 15, 1996
    Date of Patent: March 24, 1998
    Assignee: Shell Oil Company
    Inventors: Lynn Henry Slaugh, Paul Richard Weider, Joseph Broun Powell, Juan Pedro Arhancet
  • Patent number: 5723389
    Abstract: An alkanediol such as 1,3-propanediol is prepared in a process which involves reacting an alkylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of a non-phosphine-ligated cobalt or rhodium catalyst and a cobalt or rhodium porphyrin promoter to produce an intermediate product mixture containing a hydroxyalkanal in an amount less than 15 wt %; extracting the hydroxyalkanal from the intermediate product mixture into an aqueous liquid at a temperature less than about 100.degree. C. and separating the aqueous phase containing hydroxyalkanal from the organic phase containing cobalt catalyst; hydrogenating the hydroxyalkanal in the aqueous phase to an alkanediol; and recovering the alkanediol.The process enables the production of an alkanediol such as 1,3-propanediol in high yields and selectivity without the use of a phosphine ligand with the cobalt or rhodium catalyst.
    Type: Grant
    Filed: October 15, 1996
    Date of Patent: March 3, 1998
    Assignee: Shell Oil Company
    Inventors: Lynn Henry Slaugh, Paul Richard Weider, Joseph Broun Powell, Juan Pedro Arhancet
  • Patent number: 5703017
    Abstract: 3-(Het)arylcarboxylic acid derivatives of the formula I ##STR1## where R is formyl, CO.sub.2 H or a radical hydrolyzable to COOH and the other substituents have the following meanings:R.sup.2 and R.sup.3 are each halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio;X is nitrogen or CR.sup.14, where R.sup.14 is hydrogen or, together with R.sup.3, forms an alkylene or alkenylene chain, in each of which a methylene group is replaced by oxygen;R.sup.4 is phenyl or naphthyl, each of which is unsubstituted or substituted or an unsubstituted or substituted five-membered or six-membered heteroaromatic structure containing one to three nitrogen atoms or one sulfur or oxygen atom;R.sup.5 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl or phenyl;R.sup.6 is C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or C.sub.3 -C.sub.
    Type: Grant
    Filed: October 19, 1995
    Date of Patent: December 30, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Ernst Baumann, Joachim Rheinheimer, Uwe Josef Vogelbacher, Matthias Bratz, Hans Theobald, Matthias Gerber, Karl-Otto Westphalen, Helmut Walter, Wilhelm Rademacher
  • Patent number: 5672769
    Abstract: Novel derivatives of fatty acid analogs that have from one to three heteroatoms in the fatty acid moiety which can be oxygen, sulfur or nitrogen, are disclosed in which the carboxy-terminus has been modified to form various amides, esters, ketones, alcohols, alcohol esters and nitriles thereof.These compounds are useful as substrates for N-myristoyltransferase (NMT) and/or its acyl coenzyme, and as anti-viral and anti-fungal agents or pro-drugs of such agents. Illustrative of the disclosed compounds are fatty acid amino acid analogs of the structure ##STR1## in which X is the ethyl or t-butyl ester of an amino acid such as Gly, L-Ala, L-Ile, L-Phe, L-Trp, L-Thr or an amide such as NHCH.sub.2 C.sub.6 H.sub.5 or NH(CH.sub.2).sub.2 C.sub.6 H.sub.5.
    Type: Grant
    Filed: November 4, 1996
    Date of Patent: September 30, 1997
    Assignee: G. D. Searle & Co.
    Inventors: Sean T. Nugent, Richard A. Mueller
  • Patent number: 5599963
    Abstract: The invention relates to catalysts for the synthesis of .beta.-hydroxy carbonyl compounds, and in particular to enantioselective catalysts.
    Type: Grant
    Filed: March 29, 1995
    Date of Patent: February 4, 1997
    Assignee: California Institute of Technology
    Inventors: Erick M. Carreira, Robert A. Singer
  • Patent number: 5545767
    Abstract: 1,3-propanediol is prepared in a process comprising the steps of:contacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of an effective amount of a non-phosphine-ligated cobalt catalyst and an effective amount of a lipophilic phenol at a temperature within the range of about 50.degree. to about 100.degree. C. and a pressure within the range of about 500 to about 5000 psig, under reaction conditions effective to produce an intermediate product mixture comprising less than about 15 wt % 3-hydroxypropanal;adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid at a temperature less than about 100.degree. C.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: August 13, 1996
    Assignee: Shell Oil Company
    Inventors: Paul R. Weider, Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Thomas C. Semple
  • Patent number: 5463144
    Abstract: 1,3-propanediol is prepared in a process comprising the steps of:contacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of an effective amount of a non-phosphine-ligated cobalt catalyst and an effective amount of a lipophilic quaternary ammonium salt at a temperature within the range of about 50.degree. to about 100.degree. C. and a, pressure within the range of about 500 to about 5000 psig, under reaction conditions effective to produce an intermediate product mixture comprising less than 15 wt % 3-hydroxypropanal;adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid at a temperature less than about 100.degree. C.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: October 31, 1995
    Assignee: Shell Oil Company
    Inventors: Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Terry B. Thomason, Thomas C. Semple, Paul R. Weider, Juan P. Arhancet
  • Patent number: 5463146
    Abstract: 1,3-propanediol is prepared in a process comprising the steps of:(a) contacting ethylene oxide with carbon monoxide and hydrogen in an essentially non-water-miscible solvent in the presence of an effective amount of a non-phosphine-ligated cobalt catalyst and an effective amount of a lipophilic arsine at a temperature within the range of about 50 to about 100.degree. C. and a pressure within the range of about 500 to about 5000 psig, under reaction conditions effective to produce an intermediate product mixture comprising less than about 15 wt % 3-hydroxypropanal;(b) adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid at a temperature less than about 100.degree. C.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: October 31, 1995
    Assignee: Shell Oil Company
    Inventors: Lynn H. Slaugh, Joseph B. Powell, Thomas C. Forschner, Thomas C. Semple, Paul R. Weider
  • Patent number: 5463145
    Abstract: 1,3-Propanediol is prepared in a process comprising the steps of:contacting, in an essentially non-water-miscible organic solvent, ethylene oxide with carbon monoxide and hydrogen in the presence of a catalytic amount of a non-phosphine-ligated cobalt compound and an effective amount of a lipophilic quaternary phosphonium salt promoter at a temperature within the range of about 50.degree. to about 100.degree. C. and a pressure within the range of about 500 to about 5000 psig, to produce an intermediate product mixture comprising less than 15 wt % 3-hydroxypropanal;adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid a major portion of the 3-hydroxypropanal at a temperature less than about 100.degree. C.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: October 31, 1995
    Assignee: Shell Oil Company
    Inventors: Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Thomas C. Semple, Paul R. Weider
  • Patent number: 5453547
    Abstract: A novel process for the manufacture of .gamma.-acetoxytiglic aldehyde ("C.sub.5 -aldehyde"), which is known as an important starting material for the production of vitamin A acetate from a (.beta.-ionylidenethyl)triphenylphosphonium halide and C.sub.5 -aldehyde, comprises treating a pentenyn-3-ol of the formula HC.tbd.C--C(CH.sub.3)(OH)--CH.dbd.C(R).sub.2 (II), wherein both R's signify either hydrogen or methyl, with ozone, preferably in a lower alkanol R.sup.1 OH, wherein R.sup.1 signifies C.sub.1-4 -alkyl, to obtain an aldehyde 2-hydroxy-2-methyl-3-butynal of the formula HC.tbd.C--C(CH.sub.3)(OH)--CHO (III). The aldehyde III may be converted to the C.sub.5 -aldehyde by conventional means.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: September 26, 1995
    Assignee: Hoffman-La Roche Inc.
    Inventor: Ulriche Zutter
  • Patent number: 5399724
    Abstract: Novel acyclic terpene compounds useful as intermediates for producing sarcophytol A which have an anti-carcinogenic promotor activity and anti-tumor activity, which compounds are shown by the following general formula (I): ##STR1## [wherein R.sup.1 is a hydrogen atom, 1-alkoxyalkyl group, tetrahydrofuryl group, tetrahydropyranyl group or acyl group; R.sup.2 is a group of formula: --CHO, --CH.sub.2 OR.sup.3 or ##STR2## (wherein R.sup.3 is a hydrogen atom, 1-alkoxyalkyl group, tetrahydrofuryl group, tetrahydropyranyl group or acyl group; and R.sup.4 is C.sub.1 to C.sub.4 alkyl group) with the proviso that R.sup.1 and R.sup.3 do not represent the same substituents simultaneously; when R.sup.1 is a hydrogen atom, R.sup.3 is not acetyl group or tetrahydropyranyl group; and when R.sup.2 is a group of formula: ##STR3## R.sup.1 is not a hydrogen atom).
    Type: Grant
    Filed: September 28, 1993
    Date of Patent: March 21, 1995
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
  • Patent number: 5334370
    Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising a polymeric material capable of forming a coating on the gastrointestinal tract and an x-ray producing agent of the formula ##STR1## and methods for their use in diagnostic radiology of the gastrointestinal tract whereinR=C.sub.1 -C.sub.25 alkyl, cycloalkyl, unsaturated allyl or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy, lower-alkoxy carbonyl or lower-alkoxy-carbonyloxy, (CR.sub.1 R.sub.2).sub.p --(CR.sub.3 .dbd.CR.sub.4).sub.m Q, or (CR.sub.1 R.sub.2).sub.p --C.tbd.C--Q;R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently H, lower-alkyl, optionally substituted with halo;n is 1-5;m is 1-5;p is 1-10; andQ is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, or aryl-lower alkyl.
    Type: Grant
    Filed: February 4, 1993
    Date of Patent: August 2, 1994
    Assignee: Sterling Winthrop Inc.
    Inventors: Kurt A. Josef, Edward R. Bacon, Kimberly G. Estep, Carl R. Illig, Brent D. Douty
  • Patent number: 5308607
    Abstract: Disclosed are contrast agents of the formula ##STR1## contained in aqueous compositions and methods for their use in diagnostic radiology of the gastrointestinal tract whereinR=C.sub.1 -C.sub.25 alkyl, cycloalkyl, unsaturated allyl or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy, lower-alkoxy carbonyl or lower-alkoxy-carbonyloxy, (CR.sub.1 R.sub.2).sub.p --(CR.sub.3 .dbd.CR.sub.4).sub.m Q, or (CR.sub.1 R.sub.2).sub.p --C.tbd.C--Q;R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently H, lower-alkyl, optionally substituted with halo;n is 1-5;m is 1-5;p is 1-10; andQ is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, or aryl-lower alkyl.
    Type: Grant
    Filed: February 4, 1993
    Date of Patent: May 3, 1994
    Assignee: Sterling Winthrop Inc.
    Inventors: Kurt A. Josef, Edward R. Bacon, Kimberly G. Estep, Carl R. Illig, Brent D. Douty
  • Patent number: 5304686
    Abstract: This invention relates to a process for making 3-hydroxypropanal by intimately contacting(a) ethylene oxide,(b) ditertiary phosphine-modified cobalt carbonyl catalyst, said phosphine being a hydrocarbylene-bis(monophosphabicyclononane) in which each phosphorus atom is joined to hydrocarbylene and is a member of a bridge linkage without being a bridgehead atom and which hydrocarbylene-bis(monophosphabicyclononane) has 18 to 50 carbon atoms, 8 carbon atoms thereof together with a phosphorus atom being members of each of the two bicyclic skeletal structures,(c) a catalyst promoter comprising an acid and a metal salt promoter selected from a salt of a metal of Group IIA, Group IIB, Group IIIB and the Rare Earth Series of the Periodic Table of the Elements (CAS version),(d) carbon monoxide, and(e) hydrogen, the molar ratio of carbon monoxide to hydrogen being from about 4:1 to about 1:6,in liquid-phase solution in an inert reaction solvent, at a temperature of from about 30.degree. C. to about 150.degree. C.
    Type: Grant
    Filed: July 13, 1993
    Date of Patent: April 19, 1994
    Assignee: Shell Oil Company
    Inventors: Lynn H. Slaugh, Juan P. Arhancet
  • Patent number: 5304661
    Abstract: Acyclic terpene compounds useful as intermediates for producing sarcophytol A which have an anti-carcinogenic promotor activity and anti-tumor activity, which compounds are shown by the general formula (I): ##STR1##
    Type: Grant
    Filed: April 9, 1993
    Date of Patent: April 19, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
  • Patent number: 5304691
    Abstract: This invention relates to a process for making 1,3-propanediol and 3-hydroxypropanal by intimately contacting(a) ethylene oxide,(b) tertiary phosphine-complexed cobalt carbonyl catalyst(c) ruthenium catalyst,(c) carbon monoxide, and(d) hydrogen, the molar ratio of carbon monoxide to hydrogen being from about 4:1 to about 1:6,in liquid-phase solution in an inert reaction solvent, at a temperature of from about 30.degree. C. to about 150.degree. C. and a pressure of from about 50 psi to about 10,000 psi.
    Type: Grant
    Filed: July 13, 1993
    Date of Patent: April 19, 1994
    Assignee: Shell Oil Company
    Inventors: Juan P. Arhancet, Lynn H. Slaugh
  • Patent number: 5284979
    Abstract: A process is disclosed for the preparation of 3-hydroxyalkanals having 3 to 12 carbon atoms, in particular 3 or 4 carbon atoms, by hydration of the underlying 2-alkenals with water in a homogeneous phase in the presence of an acid catalyst. The previously known hydration using mineral acids or carboxylic acids as catalyst results in low volume/time yields and/or low selectivities. These disadvantages can be avoided by using in the present invention, as catalyst, a dissolved acid-base buffer which results in a pH of from 2 to 5 in the reaction mixture; the acid component and corresponding base of which are present in a total quantity of from 0.5 to 40% by weight in the reaction mixture. The preferred buffers composed of a lower monobasic carboxylic acid and a tertiary amine can easily be recycled.
    Type: Grant
    Filed: November 24, 1992
    Date of Patent: February 8, 1994
    Assignee: Degussa Aktiengesellschaft
    Inventors: Thomas Haas, Georg Bohme, Dietrich Arntz
  • Patent number: 5276201
    Abstract: A process for the production of 3-hydroxyalkanals, more particularly 3-hydroxypropionaldehyde, by hydration of the basic 2-alkenals, more particularly acrolein, in the presence of a solid catalyst containing acid functional groups. The catalysts are based on an inorganic support containing basic activity centers (which are at least partly occupied by a polybasic acid, of which the first pK.sub.s value is between 0 and 3, in a form in which it cannot be removed by water) enables the hydration to be carried out with high selectivity. At the same time, the disadvantages of known organic fixed-bed catalysts are avoided. Preferred catalyst are based on pyrogenic titanium dioxide with phosphoric acid fixed thereon.
    Type: Grant
    Filed: November 24, 1992
    Date of Patent: January 4, 1994
    Assignee: Degussa Aktiengesellschaft
    Inventors: Thomas Haas, Dietrich Arntz, Reinhold Brand
  • Patent number: 5252188
    Abstract: This invention provides a process for producing crystalline hydroxyacetaldehyde precipitated from a complex mixture of products provided by the pyrolysis of a carbohydrate-containing feedstock. The method includes distilling a first condensate under reduced pressure to give a second condensate which is enriched in hydroxyacetaldehyde; combining the second condensate with a solvent to give a homogeneous solution; precipitating hydroxyacetaldehyde from the solution; and separating the precipitated hydroxyacetaldehyde from the solution.Aqueous solutions of hydroxyacetaldehyde are useful for browning foodstuffs and for producing flavors by contacting the hydroxyacetaldehyde with ammonia or amines.In addition, hydroxyacetaldehyde may be used to make an artificial tanning product containing a suitable topical vehicle and an amount of hydroxyacetaldehyde suitable to impart a brown color to skin.
    Type: Grant
    Filed: April 10, 1992
    Date of Patent: October 12, 1993
    Assignee: Red Arrow Products Company, Inc.
    Inventors: John A. Stradal, Gary L. Underwood
  • Patent number: 5250710
    Abstract: The present invention relates to dihydropyran derivatives, processes for preparing, and processes of using the derivatives. The derivatives are prepared by condensation of lithium dienolate of prenal with an aldehyde or a ketone.The pyran derivative prepared from .beta.-ionylideneacetaldehyde when treated in the presence of a catalyst directly forms retinal.
    Type: Grant
    Filed: May 7, 1992
    Date of Patent: October 5, 1993
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre F. Chabardes, Lucette Duhamel, Pierre Duhamel, Jerome Guillemont, Jean-Marie Poirier
  • 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: 5210318
    Abstract: A process for producing a 1,3-diol, e.g., 1,3-propanediol, and/or a 3-hydroxyaldehyde, e.g., 3-hydroxypropionaldehyde, is disclosed which comprises contacting a combination of an epoxide, carbon monoxide and hydrogen in the presence of a rhodium-containing catalyst composition effective to promote the hydroformylation of the epoxide at conditions effective to form at least one of a 1,3-diol and a 3-hydroxyaldehyde. The rhodium-containing catalyst composition comprises an anionic rhodium-containing complex. A promoter component is preferably provided to enhance at least one of the rate and selectivity of the epoxide hydroformylation reaction Rhodium-containing compositions and a processes for producing rhodium-containing compositions are also disclosed.
    Type: Grant
    Filed: March 18, 1991
    Date of Patent: May 11, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: John R. Briggs, John M. Maher, Arnold M. Harrison
  • Patent number: 5196609
    Abstract: The preparation of 3-alkoxycarbonyl propenals and 3-dialkoxymethyl propenals of the general formulae Ia and Ib respectively: ##STR1## (R.sup.1 =C.sub.1 -C.sub.3 -alkyl group; R.sup.2 and R.sup.3 =hydrogen, methyl, or ethyl; and R.sup.4 and R.sup.5 =C.sub.1 -C.sub.4 -alkyl groups, which may be joined to form a 5-membered or 6-membered ring), is effected by reacting a corresponding alcohol of the general formula IIa or IIb ##STR2## with oxygen or an oxygen-containing gas in the gas phase in the presence of a metal from Group IB of the Periodic Table or a compound of one such metal acting as catalyst.The target products serve as intermediates for the synthesis of carotenoids.
    Type: Grant
    Filed: March 2, 1992
    Date of Patent: March 23, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Aquila, Hans-Ulrich Scholz, Hartwig Fuchs, Wolfgang Krause, Joachim Paust, Werner Hoffmann