Hydroxymethyl Group Containing Patents (Class 568/764)
  • Patent number: 10744490
    Abstract: A process for preparing a catalyst includes impregnating a metal oxide carrier with an aqueous solution to form an impregnated carrier; drying the impregnated carrier to form a dried, impregnated carrier; and heat-treating the dried, impregnated carrier in air to form the catalyst; wherein: the aqueous solution includes a copper salt; and from about 3 wt % to about 15 wt % of a C3-C6 multifunctional carboxylic acid; and the catalyst includes from about 5 wt % to about 50 wt % copper oxide.
    Type: Grant
    Filed: August 30, 2019
    Date of Patent: August 18, 2020
    Assignee: BASF CORPORATION
    Inventors: Keenan Lee Deutsch, Rostam J. Madon
  • Publication number: 20150011801
    Abstract: Renewable resources comprising bagasse, corn stover, wood sawdust and switch grass are subject to direct catalytic conversion or bio-fermentation producing ethanol leaving complex lignin compounds for disposal. Chemical conversion of lignin compounds (recoverable from digested lignin) to substituted phenols followed by a carbon steel catalyzed pulsed flow hydrogenation produces cresol and substituted creosol compounds. The pulsed flow process produced close to 100 percent reduction of the reactants compared to 25 percent with continuous flow and is applicable to aliphatic carboxylic acid compounds such as natural oils producing valued liquid hydrocarbons.
    Type: Application
    Filed: July 8, 2013
    Publication date: January 8, 2015
    Applicant: Carter Technologies Corporation
    Inventor: M. K. Carter
  • Publication number: 20140256989
    Abstract: A process for preparing hydroxytyrosol, wherein a compound where X is CH2OH or CH2OM (M=Li, Na, K, Mg, Ca), R1 and R2 are identical or different and are C1-C8 alkyl radical, benzyl radical, alkyl- or halogen-substituted benzyl radical or arylalkyl radical, where R1 and R2 can also be linked via to give a ring, R2, R4, R5 and R6 are identical or different and are hydrogen or C1-C6 alkyl radical, aryl radical, alkyl-substituted aryl radical, where R5 and R6 can also be linked via —(CH2)4—, —(CH2)5— or —(CH2)6— to give a ring, is reacted with an aluminum compound AlR7R8R9 (2), where R7, R8 and R9 are identical or different and are H or C1-C8 alkyl radical, and then an aqueous solution of a hydroxycarboxylic acid is added to form a clear homogeneous acidic solution with a pH<3, and hydroxytyrosol is extracted therefrom.
    Type: Application
    Filed: February 25, 2014
    Publication date: September 11, 2014
    Applicant: Wacker Chemie AG
    Inventors: Benno KRUEGER, Gerald FLEISCHMANN, Hermann PETERSEN
  • Publication number: 20140107319
    Abstract: Disclosed are a carrier for use for separation purpose and a method for separation of a compound which enable a chemical reaction to be performed in a liquid phase, enable a compound of interest to be separated from the liquid phase after the completion of the reaction readily, enable the separated compound to be evaluated by structural analysis or the like while the compound being bound to the carrier, and enable the compound to be separated from the carrier readily. A carrier for separation which has a reaction site capable of reacting with other compound on a benzene ring, and a long-chain group having a specified carbon atom(s) at each of the ortho-position and the para-position of the reaction site through an oxygen atom.
    Type: Application
    Filed: December 20, 2013
    Publication date: April 17, 2014
    Applicants: JITSUBO Co., Ltd., National University Corporation, Tokyo University of Agriculture and Technology
    Inventors: Kazuhiro Chiba, Shokaku Kim, Yusuke Kono
  • Publication number: 20130245130
    Abstract: Provided herein are pure and isolated natural products and analogs thereof of Formula (I), (II), (III), and (IV), pharmaceutical compositions thereof, and methods of use, for example, for treating a bacterial infection. Further provided are methods useful in identifying an inhibitor of bacterial sugar fermentation in a bacterial strain, such as a compound (inhibitor) of Formula (I), (II), (III), or (IV): or a pharmaceutically acceptable salt thereof.
    Type: Application
    Filed: February 25, 2013
    Publication date: September 19, 2013
    Applicants: President and Fellows of Harvard College, Children's Medical Center Corporation
    Inventors: Paula I. Watnick, Patrick Ymele-Leki, Jon Clardy, Shugeng Cao
  • Publication number: 20130096209
    Abstract: The present invention provides edible compositions comprising a compound of the present invention, food products comprising such edible compositions and methods of preparing such food products. The present invention also provides methods of reducing the amount of NaCl in a food product, methods of reducing the sodium intake in a diet, and methods of reducing bitter taste in a food product.
    Type: Application
    Filed: April 15, 2011
    Publication date: April 18, 2013
    Applicants: Kraft Foods Global Brands LLC, Chromocell Corporation
    Inventors: David Hayashi, William P. Jones, Jane V. Leland, Peter H. Brown, Joseph Gunnet, Daniel Lavery, Louise Slade, Kambiz Shekdar, Jessica Langer
  • Patent number: 8017815
    Abstract: Process for the preparation of hydroxytyrosol, characterized by reacting 4-chloroacetyl-catechol with a metal formate and formic acid in an aqueous solvent optionally containing a lower alkanol and catalytically hydrogenating the 4-hydroxyacetyl-catechol obtained in the presence of a precious metal, preferably on a carrier.
    Type: Grant
    Filed: February 28, 2008
    Date of Patent: September 13, 2011
    Assignee: DSM IP Assets B.V.
    Inventors: Manfred Breuninger, Marcel Joray
  • Publication number: 20100324343
    Abstract: Process for the preparation of hydroxytyrosol, characterized by reacting 4-chloroacetyl-catechol with a metal formate and formic acid in an aqueous solvent optionally containing a lower alkanol and catalytically hydrogenating the 4-hydroxyacetyl-catechol obtained in the presence of a precious metal, preferably on a carrier.
    Type: Application
    Filed: February 28, 2008
    Publication date: December 23, 2010
    Inventors: Manfred Breuninger, Marcel Joray
  • Patent number: 7148386
    Abstract: A process for the preparation of hydroquinone compounds comprising, reacting an aromatic hydroxy compound with an oxidizing agent in a biphasic solvent system. The reaction is carried out in the presence of a transition metal hydroxy phosphate catalyst to produce the corresponding hydroquinone compound.
    Type: Grant
    Filed: July 30, 2004
    Date of Patent: December 12, 2006
    Assignee: General Electric Company
    Inventors: Jegadeesh Thampi, Sunil Ashtekar, Pramod Kumbhar, Rathinam Jothi Mahalingam
  • Patent number: 7087799
    Abstract: An object of the present invention is to provide a material which resolves the drawbacks associated with polyimide polymers, and yet retains the advantages offered by conventional polyimide polymers. An amino group containing phenol derivative of the present invention is represented by a general formula (1) show below, and the present invention also provides a polyimide precursor produced using such an amino group containing phenol derivative. (wherein, R1, R2 and R3, which may be the same or different, each represent an alkyl group of 1 to 9 carbon atoms, an alkoxy group of 1 to 10 carbon atoms, a COOR group (in which R represents an alkyl group of 1 to 6 carbon atoms) or a hydrogen atom; R4 and R5, which may be the same or different, each represent an alkyl group of 1 to 9 carbon atoms or a hydrogen atom; X represents —O—, —S—, —SO2—, —C(CH3)2—, —CH2—, —C(CH3)(C2H5)—, or —C(CF3)2—; and n represents an integer of 1 or greater).
    Type: Grant
    Filed: January 31, 2003
    Date of Patent: August 8, 2006
    Assignee: Gun Ei Chemical Industry Co., Ltd.
    Inventors: Takeshi Tsuihiji, Michiyasu Yamazaki
  • Patent number: 6806395
    Abstract: A process for producing a 3,5-bisalkylphenol (2) according to the following reaction scheme: (wherein R1 represents a hydrogen atom, an alkali metal atom, an alkaline earth metal atom, or a hydroxyl-protecting group (other than methyl group); R2 represents a C1 to C5 lower alkyl group or an optionally substituted phenyl group; and each of R3 and R4, which may be identical to or different from each other, represents a lower alkyl group, an aralkyl group, or an aryl group); a carbinol compound (1); and a process for producing the carbinol compound. The production process of the present invention enables efficient and safe production of a variety of 3,5-bisalkylphenols including 3,5-diisopropylphenol, which are important as synthesis intermediates for drugs and agricultural chemicals, in shorter steps at high purity in high yield, thus contributing to consistent supply of drugs and agricultural chemicals.
    Type: Grant
    Filed: March 18, 2003
    Date of Patent: October 19, 2004
    Assignee: Kowa Co., Ltd.
    Inventors: Kimiyuki Shibuya, Tadaaki Ohgiya, Toru Miura, Kazuhiro Onogi
  • Patent number: 6600078
    Abstract: A heterogeneous liquid-phase process for the hydrogenation of aldehydes of Formula (I) and (III) to the corresponding alcohols of Formula (II) and (IV) which process comprises contacting alcoholic or aqueous-alcoholic solution of aldehydes and hydrogen gas with a catalyst comprising a reduced mixture of CuO and ZnO in presence of a metal of group IIIA of the Periodic Table, such as aluminium, as a promoter at a temperature of between about 110° and 180° C. and a pressure of between about 20 and 500 psig.
    Type: Grant
    Filed: August 12, 2002
    Date of Patent: July 29, 2003
    Assignee: Saudi Basic Industries Corporation
    Inventors: Meftahuddin Mahmud, Ahmad Kamal Faizi, Vidyasagar Anchoori, Abdullah Al-Qahtani
  • Patent number: 6554967
    Abstract: A refined dihydroxyaryl compound, for example, catechol, having a high degree of purity and a very low metal content is produced by evaporating a starting dihydroxyaryl compound in a distillation column, condensing the vapor fraction in a condenser connected to a top outlet of the distillation column, and collecting the condensed fraction from the condenser into a storage tank through a conduit, wherein the condenser and optionally the conduit and/or the storage tank have inside surfaces thereof formed from a metal material containing at least 25% by weight of nickel, and the condensed dihydroxyaryl compound fraction is brought into contact with the specific nickel (25% or more)-containing metal inside surface.
    Type: Grant
    Filed: May 22, 2000
    Date of Patent: April 29, 2003
    Assignee: UBE Industries, Ltd.
    Inventors: Shuji Tanaka, Genji Koga, Hiroshi Kofuji, Tetsuro Kawashita
  • Patent number: 6518315
    Abstract: A compound of formula (I), a pharmaceutically acceptable derivative thereof, wherein Ph is a phenyl radical R1 is H, OH, OC1-4alkyl, NO2; R2 is OH, OC1-4alkyl, OC═OC1-4alkyl or OC═OPh where the Ph can be optionally substituted by halogen, C1-3 alkyl or NO2; R1 and R2 along with the two carbon atoms of the phenyl ring to which they are attached can combine to form a 5 or 6 membered heterocyclic ring comprising 1 or 2 heteroatoms selected from O, S or N; R3 is an optionally substituted hydroycarby radical; R4 is H, CH3, OH or ═O; when R4 is ═O, then the carbon to which R4 is attached is not bonded to H; W is C(═O)—CH2, CH═CH—, CH2CO, CH(OH)—CH2, C(CH3)(OH)CH2, CH2CH(OH), CH2C(CH3)OH, CO, CHOH, C(CH3)(OH), CH2, CH2CH2; X is —CH—OH, C(CH3)OH, CH2, CH(CH3) or —C═O; Y is —CH—OH, C(CH3)OH, CH2, CH(CH3) or —C═O; provided that one of W, X or Y has an OH group.
    Type: Grant
    Filed: June 23, 2000
    Date of Patent: February 11, 2003
    Assignee: The University of Sydney
    Inventors: Basil Don Roufogalis, Colin Charles Duke, Van Hoan Tran
  • Publication number: 20020198415
    Abstract: The invention provides olive-derived hydroxytyrosol. According to one aspect of the invention, vegetation water is collected from olives. Acid is added to stabilize the vegetation water and prevent fermentation. The mixture is incubated to allow oleoeuropein to convert to hydroxytyrosol, and then fractionated to separate hydroxytyrosol from other components. The hydroxytyrosol is useful as a natural anti-bacterial, anti-viral and fungicidal product for agricultural and pest control applications. In addition, it is useful as a therapeutic and anti-oxidant for a variety of health purposes.
    Type: Application
    Filed: June 7, 2002
    Publication date: December 26, 2002
    Applicant: CREAGRI, INC.
    Inventor: Roberto Crea
  • Patent number: 6414197
    Abstract: A method and a catalyst are described for selective oxidation of aromatic compounds (e.g., benzene and its derivatives) into hydroxylated aromatic compounds (e.g., corresponding phenols). For example, benzene can be converted into phenol with a yield of at least 30-40%, and a selectivity on the basis of benzene of at least 95-97%. The selectivity for this reaction based on N2O is at least 90-95%. Therefore, no substantial N2O decomposition or consumption for complete benzene oxidation to CO+CO2 or other side products occurs. Similar results are obtained with benzene derivatives (e.g., fluorobenzene, difluorobenzene, phenol), although the selectivity is somewhat lower in the case of derivatives (e.g., about 80-85% in the case of fluorosubstituted benzenes). A preferred catalyst for this process is a composition containing a high-silica pentasil-type zeolite (e.g, an HZSM-5 type zeolite) which contains no purposefully introduced additives such as transition or noble metals.
    Type: Grant
    Filed: May 13, 1998
    Date of Patent: July 2, 2002
    Assignee: General Electric Company
    Inventors: Leonid Modestovich Kustov, Viktor Ignatyevich Bogdan, Vladimir Borisovich Kazansky
  • Patent number: 6380441
    Abstract: 3-Hydroxybenzyl alcohol can be prepared in a simple and inexpensive way by subjecting 3-chloromethylphenyl chloroformate to an acidolysis with a carboxylic acid or a carboxylic acid salt and subsequently subjecting the reaction product of the first step to an alcoholysis.
    Type: Grant
    Filed: September 7, 2001
    Date of Patent: April 30, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Franz-Josef Mais, Herbert Diehl
  • Publication number: 20020040168
    Abstract: A method and a catalyst are described for selective oxidation of aromatic compounds (e.g., benzene and its derivatives) into hydroxylated aromatic compounds (e.g., corresponding phenols). For example, benzene can be converted into phenol with a yield of at least 30-40%, and a selectivity on the basis of benzene of at least 95-97%. The selectivity for this reaction based on N2O is at least 90-95%. Therefore, no substantial N2O decomposition or consumption for complete benzene oxidation to CO+CO2 or other side products occurs. Similar results are obtained with benzene derivatives (e.g., fluorobenzene, difluorobenzene, phenol), although the selectivity is somewhat lower in the case of derivatives (e.g., about 80-85% in the case of fluorosubstituted benzenes). A preferred catalyst for this process is a composition containing a high-silica pentasil-type zeolite (e.g, an HZSM-5 type zeolite) which contains no purposefully introduced additives such as transition or noble metals.
    Type: Application
    Filed: May 13, 1998
    Publication date: April 4, 2002
    Inventors: LEONID MODESTOVICH KUSTOV, VIKTOR IGNATYEVICH BOGDAN, VLADIMIR BORISOVICH KAZANSKY
  • Publication number: 20020032353
    Abstract: 3-Hydroxybenzyl alcohol can be prepared in a simple and inexpensive way by subjecting 3-chloromethylphenyl chloroformate to an acidolysis with a carboxylic acid or a carboxylic acid salt and subsequently subjecting the reaction product of the first step to an alcoholysis.
    Type: Application
    Filed: September 7, 2001
    Publication date: March 14, 2002
    Inventors: Franz-Josef Mais, Herbert Diehl
  • Publication number: 20010004670
    Abstract: A process for condensing at least one carbonyl compound carrying at least one electron-withdrawing group with an aromatic derivative carrying at least one hydroxyl functional group, wherein the electron-withdrawing group present on the carbonyl compound is selected from fluoroalkyl derivatives, esters, including orthoesters, and nitrites and said condensation is carried out in a basic medium.
    Type: Application
    Filed: November 29, 2000
    Publication date: June 21, 2001
    Inventors: Roland Jacquot, Michel Spagnol
  • Patent number: 6218431
    Abstract: Substituted biphenyls having glucagon receptor antagonistic activity. Claimed compounds have the formula wherein R1a and R1b independently represent (C1-C6) alkyl; R2 represents (C1-C10) alkyl or substituted (C1-C10) alkyl wherein the substituents are independently from 1 to 3 of —SR7; R7 represents phenyl, or substituted phenyl wherein the substituents are independently 1-5 of halogen, trifluoromethyl, (C1-C6) alkyl, (C1-C6) alkoxy, nitro, cyano, or hydroxyl; R3 represents substituted (C1-C6) alkyl wherein the substituents are 1-2 hydroxyl groups; G represents a substituent selected from the group consisting of halogen, (C1-C6) alkyl, and OR4 wherein R4 is H or (C1-C6) alkyl; and y is 0 or an integer of 1-3. Pharmaceutical compositions containing such compounds and methods of treatment of glucagon-mediated conditions by administering such compounds are also claimed.
    Type: Grant
    Filed: July 31, 1997
    Date of Patent: April 17, 2001
    Assignees: Bayer Corporation, Bayer Aktiengesellschaft
    Inventors: William R. Schoen, Gaetan H. Ladouceur, James H. Cook, II, Timothy G. Lease, Donald J. Wolanin, Richard H. Kramss, Donald L. Hertzog, Martin H. Osterhout
  • Patent number: 6184421
    Abstract: The present invention concerns a process for the preparation of a 4-hydroxybenzaldehyde and its derivatives. More particularly, the invention concerns the preparation of 3-methoxy-4-hydroxybenzaldehyde and 3-ethoxy-4-hydroxybenzaldehyde, respectively known as vanillin and ethylvanillin.
    Type: Grant
    Filed: May 13, 1999
    Date of Patent: February 6, 2001
    Assignee: Rhodia Chimie
    Inventor: Pascal Metivier
  • Patent number: 5811587
    Abstract: The present invention concerns a process for the hydroxyalkylation of a carbocyclic aromatic ether.The invention preferably relates to the preparation of 3-methoxy-4-hydroxybenzyl alcohol by the hydroxymethylation of guaiacol.It also concerns the oxidation of the hydroxyalkylated ethers obtained, in particular the oxidation of 3-methoxy-4-hydroxybenzyl alcohol to 3-methoxy-4-hydroxybenzaldehyde, commonly known as "vanillin".The process for the hydroxyalkylation of a carbocyclic aromatic ether of the invention consists of reacting the aromatic ether with a carbonyl compound in the presence of a catalyst and is characterized in that the hydroxyalkylation reaction is carried out in the presence of an effective quantity of a zeolite.
    Type: Grant
    Filed: January 23, 1997
    Date of Patent: September 22, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Claude Moreau, Sylvie Razigade-Trousselier, Annie Finiels, Francois Fajula, Laurent Gilbert
  • Patent number: 5783737
    Abstract: The present invention concerns a process for the preparation of 3-carboxy-4-hydroxybenzaldehydes and derivatives thereof from phenolic compounds carrying formyl and/or hydroxymethyl groups in the 2 and 4 positions.The invention also concerns the preparation of 4-hydroxybenzaldehydes from 3-carboxy-4-hydroxybenzaldehydes.More particularly, the invention concerns the preparation of 3-methoxy-4-hydroxybenzaldehyde and 3-ethoxy-4-hydroxybenzaldehyde, respectively known as "vanillin" and "ethylvanillin".The process for the preparation of 3-carboxy-4-hydroxybenzaldehyde is characterized in that the group in the 2 position in a phenolic compound carrying formyl and/or hydroxymethyl groups in the 2 and 4 positions is selectively oxidized to a carboxy group, and optionally a hydroxymethyl group in the 4 position is selectively oxidized to a formyl group.A successive decarboxylation step for a 3-carboxy-4-hydroxybenzaldehyde produces a 4-hydroxybenzaldehyde.
    Type: Grant
    Filed: January 24, 1997
    Date of Patent: July 21, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventor: Pascal Metivier
  • Patent number: 5705167
    Abstract: Novel pharmaceutically/cosmetically-active aromatic polyenic compounds have the structural formula (I): ##STR1## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
    Type: Grant
    Filed: April 26, 1995
    Date of Patent: January 6, 1998
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventors: Jean-Michel Bernardon, Philippe Nedoncelle
  • Patent number: 5563300
    Abstract: The present invention provides a unique and novel way of producing carbinols such as 4-hydroxyphenylmethylcarbinol (HPMC). In this new process, a ketone such as 4-hydroxyacetophenone (4-HAP) is heated under suitable hydrogenation conditions of temperature and pressure in the presence of a suitable catalyst and a basic material, and for a sufficient period of time to form HPMC.
    Type: Grant
    Filed: December 7, 1995
    Date of Patent: October 8, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: James R. Sounik, Graham N. Mott, Charles B. Hilton, Mohammad Aslam
  • Patent number: 5498804
    Abstract: The present invention provides a unique and novel way of producing carbinols such as 4-hydroxyphenylmethylcarbinol (HPMC). In this new process, a ketone such as 4-hydroxyacetophenone (4-HAP) is heated under suitable hydrogenation conditions of temperature and pressure in the presence of a suitable catalyst and for a sufficient period of time to form HPMC.
    Type: Grant
    Filed: March 17, 1995
    Date of Patent: March 12, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: James R. Sounik, Graham N. Mott, Charles B. Hilton
  • Patent number: 5393776
    Abstract: This invention relates to structurally novel acyclic tocotrienol analogs, which are useful for cholesterol/lipid lowering in cases of hypercholesterolemia and hyperlipidemia, and for atherosclerosis. Also provided are pharmaceutical compositions and a method of use employing those compositions.
    Type: Grant
    Filed: May 13, 1994
    Date of Patent: February 28, 1995
    Assignee: Bristol-Myers Squibb Company
    Inventor: Bradley C. Pearce
  • Patent number: 5041283
    Abstract: A cosmetic composition comprising a long-chain alkyltrimethylol is disclosed. The alkyltrimethylol is represeneted by the formula (I): ##STR1## wherein R is a linear or branched, saturated or unsaturated alkyl group having 8-22 carbon atoms. The composition is applied to various types of cosmetic and exhibits superior extendibility when applied, imparts a non-sticky, fresh feeling upon use, and provides an excellent moisture-retaining effect.
    Type: Grant
    Filed: September 8, 1989
    Date of Patent: August 20, 1991
    Assignee: Kao Corporation
    Inventors: Katsumi Kita, Tetsuo Uno, Shinichi Masuda, Kazuyuki Yahagi, Kazuhiro Tashiro
  • Patent number: 5019656
    Abstract: A process for preparing p-hydroxybenzyl alcohol or a derivative thereof comprising reacting a phenol and a formaldehyde source under a basic condition is disclosed, wherein the reaction is carried out in an alcoholic organic solvent in the presence of a crown ether. The process achieves high selectivity toward the para position without involving high cost.
    Type: Grant
    Filed: February 27, 1990
    Date of Patent: May 28, 1991
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Hiroshi Iwane, Takahiro Sugawara, Naoki Suzuki
  • Patent number: 4959391
    Abstract: Phenol derivatives of the formula ##STR1## wherein A and B have the same or different meanings and each represent one of the groups --C.tbd.C--, cis--CH.dbd.CH-- or trans--CH.dbd.CH--, R.sub.1 is hydrogen, an optionally substituted alkyl or phenyl group or a cycloalkyl group, R.sub.2 is hydrogen, methyl or ethyl, R.sub.3 represents hydrogen, acetyl or propionyl, R.sub.4 has the same meaning as R.sub.3 or represents an alkyl group, R.sub.5 is a carboxylic or a hydroxy group or a functional derivative of such groups or R.sub.5 is a nitrile group and R.sub.6 is hydrogen, an alkyl group or the group OR.sub.4 which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of diseases due to the action of leukotrienes. The compounds are prepared by reacting suitable acetylene compounds or metal derivatives thereof with alkyl or aryl halides or by means of Wittig reactions optionally followed by transforming the member R.sub.
    Type: Grant
    Filed: July 14, 1988
    Date of Patent: September 25, 1990
    Assignee: Gruenenthal GmbH
    Inventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin O. Kiesewetter, Ulrich G. P. Seippl
  • Patent number: 4915875
    Abstract: Paramethyl-substituted hindered phenols are selectively oxidized by contacting with an oxidizing agent at elevated temperatures in the presence of a heterogeneous oxidative coupling catalyst. In the absence of an optional nucleophile the products comprise carbon-carbon oxidative coupling products. In the presence of a nucleophile, addition products result that may be further oxidized by continued exposure to the oxidizing agent to yield substituted p-hydroxybenzaldehydes.
    Type: Grant
    Filed: November 4, 1986
    Date of Patent: April 10, 1990
    Assignee: The Dow Chemical Company
    Inventors: Timothy R. Diephouse, Robert M. Strom
  • Patent number: 4900354
    Abstract: Compounds of the class comprising (quinolinyl and quinoxalinyloxy)phenoxy) alkenols, e.g., 4-(4-((6-chloro-2-quinolinyl)oxy)phenoxy)-2-penten-1-ol; and a method of preparation, comprising reacting an appropriately substituted quinoline or quinoxaline, e.g., 2,6-dichloroquinoline, with a phenolic substituted pentenol, e.g., 4-(4-hydroxyphenoxy)-2-penten-1-ol, in the presence of a base and organic solvent under an inert atmosphere with or without heat, and then recovering the product.These compounds are useful as intermediates for preparing various known herbicidal compounds and are useful in their own right as post-emergent herbicides for controlling grassy weeds in the presence of corn plants.
    Type: Grant
    Filed: August 29, 1986
    Date of Patent: February 13, 1990
    Assignee: The Dow Chemical Company
    Inventors: James A. Turner, Paul S. Zorner, Wendy S. Jacks
  • Patent number: 4879416
    Abstract: The process for preparing a bidentate ligand comprising the steps,(1) contacting with ozone under ozonolysis conditions a suspension in a hydroxylic reaction medium of phenanthrene or a phenanthrene derivative to form an ozonated intermediate,(2) contacting said ozonated intermediate with a reducing agent under conditions appropriate to form the corresponding diol,(3) contacting said diol with a latent displaceable functional group under conditions appropriate to convert the diol to the corresponding difunctional biaryl compound, and(4) contacting said difunctional biaryl compound, with an anion of N, P, As, Sb or Bi under conditions appropriate to form the desired bidentate ligand.
    Type: Grant
    Filed: November 23, 1987
    Date of Patent: November 7, 1989
    Assignee: Eastman Kodak Company
    Inventors: Thomas A. Puckette, Thomas J. Devon, Gerald W. Phillips, Jerome L. Stavinoha
  • Patent number: 4849548
    Abstract: A 4-halomethyl-3,5-dihalo-2,6-dialkylphenol is hydrolyzed by contact with water to form a 4-hydroxy-methyl-3,5-dihalo-2,6-dialkylphenol under conditions to minimize formation of the corresponding bis-(4-hydroxy-3,5-dialkyl-2,6-dihalobenzyl) ether.
    Type: Grant
    Filed: March 21, 1988
    Date of Patent: July 18, 1989
    Assignee: The Dow Chemical Company
    Inventor: Ming-Biann Liu
  • Patent number: 4760087
    Abstract: Phenol derivatives of the formula ##STR1## wherein A and B have the same or different meanings and each represent one of the groups --C.tbd.C--, cis--CH.dbd.CH-- or trans--CH.dbd.CH--, R.sub.1 is hydrogen, an optionally substituted alkyl or phenyl group or a cycloalkyl group, R.sub.2 is hydrogen, methyl or ethyl, R.sub.3 represents hydrogen, acetyl or propionyl, R.sub.4 has the same meaning as R.sub.3 or represents an alkyl group, R.sub.5 is a carboxylic or a hydroxy group or a functional derivative of such groups or R.sub.5 is a nitrile group and R.sub.6 is hydrogen, an alkyl group or the group OR.sub.4 which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of diseases due to the action of leukotrienes. The compounds are prepared by reacting suitable acetylene compounds or metal derivatives thereof with alkyl or aryl halides or by means of Wittig reactions optionally followed by transforming the member R.sub.
    Type: Grant
    Filed: May 13, 1986
    Date of Patent: July 26, 1988
    Assignee: Gruenenthal GmbH
    Inventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin Kiesewetter, Ulrich G. P. Seipp
  • Patent number: 4590304
    Abstract: An acetylenic end-capping agent of the general formula ##STR1## wherein R.sup.1 and R.sup.2 can be the same or different and are selected from the group consisting of hydrogen, C11 to C4 alkyl, phenyl and substituted phenyl, and wherein R.sup.1 and R.sup.2 together with the carbon atom to which they are attached form a saturated 5- or 6-membered ring. This end-capping agent is substantially free of Pd and Cu.Also provided is a method for producing this end-capping agent and a method for producing acetylene terminated compounds.
    Type: Grant
    Filed: May 15, 1985
    Date of Patent: May 20, 1986
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: J. Shield Wallace, Fred E. Arnold
  • Patent number: 4540833
    Abstract: An acetylenic end-capping agent of the general formula ##STR1## wherein R.sup.1 and R.sup.2 can be the same or different and are selected from the group consisting of hydrogen, C11 to C4 alkyl, phenyl and substituted phenyl, and wherein R.sup.1 and R.sup.2 together with the carbon atom to which they are attached form a saturated 5- or 6-membered ring. This end-capping agent is substantially free of Pd and Cu.Also provided is a method for producing this end-capping agent and a method for producing acetylene terminated compounds.
    Type: Grant
    Filed: March 21, 1984
    Date of Patent: September 10, 1985
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: J. Shield Wallace, Fred E. Arnold
  • Patent number: 4460800
    Abstract: The preparation of hydroxyaryldialkylcarbinols by the reaction of hydroxyaryl alkyl ketones or alkyl hydroxyarenecarboxylates with Grignard reagents in a mixed ether-aromatic hydrocarbon solvent is frequently difficult on a large-scale basis because of formation of a voluminous precipitate of mixed magnesium salt. In an improvement in this process, a solution of the ketone or ester in an ether is added to the solution of the Grignard reagent.
    Type: Grant
    Filed: February 22, 1983
    Date of Patent: July 17, 1984
    Assignee: General Electric Company
    Inventors: Charles M. Orlando, Howard J. Klopfer
  • Patent number: 4460799
    Abstract: This invention relates to a process for the selective preparation of ortho-hydroxybenzyl alcohols and, in particular, ortho-hydroxybenzyl alcohol. According to the invention, the reaction of a phenol with an aldehyde in an initially anhydrous medium and in the presence of a catalytic amount of a metal phenate, results in the selective production of ortho-hydroxybenzyl alcohols.
    Type: Grant
    Filed: June 23, 1982
    Date of Patent: July 17, 1984
    Assignee: Isover Saint-Gobain
    Inventors: Robert Perrin, Roger Fugier
  • Patent number: 4435601
    Abstract: Optionally aldehyde substituted polyphenols are prepared by oxidizing, with hydrogen peroxide, a hydroxybenzaldehyde bearing at least one aldehyde substituent ortho- and/or para- to the nuclear hydroxyl group, in an aqueous reaction medium and in the presence of an alkali or alkaline earth metal base, the process being characterized in that the pH of the reaction medium is continuously maintained at a value no greater than 7 throughout the course of the oxidation reaction.The subject process is well suited for the preparation of, e.g., hydroxy-p-vanillin from guaiacol, and the novel compound 2,4,6-triformylphenol.
    Type: Grant
    Filed: July 7, 1981
    Date of Patent: March 6, 1984
    Assignee: Rhone-Poulenc Industries
    Inventors: Karel Formanek, Daniel Michelet, Dominique Petre
  • Patent number: 4408074
    Abstract: A process for preparing 1-(3,5-dimethoxy-4-hydroxy phenyl)-2-(N-methylamino) ethanol hydrochloride is described by reacting 2,6-dimethoxyphenol with anhydrous chloral in the presence of a catalyst, hydrolyzing 1-(3,5-dimethoxy-4-hydroxyphenyl)2,2,2-trichloro ethanol and subsequently isolating the 3,5-dimethoxy-4-hydroxyphenyl glyoxal thus obtained; finally, this compound, in the form of the bisulfite, is directly converted to the desired product by amination with methylamine in the presence of hydrogen with a hydrogenation catalyst and the final product is converted into the hydrochloride.
    Type: Grant
    Filed: November 2, 1981
    Date of Patent: October 4, 1983
    Assignee: Dr. Lo. Zambeletti S.p.A.
    Inventors: Massimo Signorini, Attilio Trebbi, Luigi Molteni
  • Patent number: 4318848
    Abstract: Chemical reaction products, obtained in an alkaline medium and which require the addition of a dispersing agent, are neutralized by addition of a free surface-active acid to which, after its preparation, basic agents have not been added or have only been added up to a pH value of 3.
    Type: Grant
    Filed: January 3, 1978
    Date of Patent: March 9, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Heinz Molls, Willy Schiwy, Reinhold Hornle, Reinhard Nebeling
  • Patent number: 4301088
    Abstract: A method for preparing benzyl alcohols or substituted benzyl alcohols is disclosed by decarbonylation of formic acid esters of benzyl alcohols or ring substituted benzyl alcohols, the decarbonylation being carried out in the presence of a catalyst.
    Type: Grant
    Filed: June 6, 1979
    Date of Patent: November 17, 1981
    Assignee: Dynamit Nobel AG
    Inventor: Gunther Bernhardt
  • Patent number: 4291178
    Abstract: A yield improved process for the preparation of orthohydroxybenzyl alcohols by esterifying a phenol with boric acid, next condensing the product of esterification with either formaldehyde or a formaldehyde-generating compound, thus effecting formulation of a boric acid ester of the desired ortho-hydroxybenzyl alcohol, and thence decomposing said ester to liberate the ortho-hydroxybenzyl alcohol therefrom, the improvement which comprises preparing the boric acid/phenol esters from at least 1.1 mols of the phenol per mol of boric acid.
    Type: Grant
    Filed: July 5, 1979
    Date of Patent: September 22, 1981
    Assignee: Rhone-Poulenc Industries
    Inventor: Joel L. Ludec
  • Patent number: 4284829
    Abstract: Compounds useful for pharmacological and medicinal purposes having the formulae ##STR1## wherein R is H, C.sub.1 -C.sub.5 alkanoyl; R.sub.1 is H, benzyl, C.sub.1 14 C.sub.5 alkanoyl, P(O)(OH).sub.2, --CO(CH.sub.2).sub.2 COOH or a basic acyl group; each of R.sub.2 and R.sub.4 is H, C.sub.1 -C.sub.6 alkyl, phenyl, pyridyl or (CH.sub.2).sub.y C.sub.6 H.sub.5 ; y is 1-4; R.sub.3 is H or CH.sub.3 ; Z is C.sub.1 -C.sub.13 alkylene or --(alk.sub.1).sub.m --O--(alk.sub.2).sub.n --; each of (alk.sub.1) and (alk.sub.2) is C.sub.1 -C.sub.13 alkylene with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 13; each of m and n is 0 or 1; and W is H, pyridyl, phenyl, fluorophenyl or chlorophenyl; intermediates therefor and methods for their preparation and use.
    Type: Grant
    Filed: December 22, 1978
    Date of Patent: August 18, 1981
    Assignee: Pfizer Inc.
    Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4283569
    Abstract: Compounds useful for pharmacological and medicinal purposes having the formulae ##STR1## wherein R is H, C.sub.1 -C.sub.5 alkanoyl; R.sub.1 is H, benzyl, C.sub.1 -C.sub.5 alkanoyl, P(O)(OH).sub.2, --CO(CH.sub.2).sub.2 COOH or a basic acyl group; each of R.sub.2 and R.sub.4 is H, C.sub.1 -C.sub.6 alkyl, phenyl, pyridyl or (CH.sub.2).sub.y C.sub.6 H.sub.5 ; y is 1-4; R.sub.3 is H or CH.sub.3 ; Z is C.sub.1 -C.sub.13 alkylene or --(alk.sub.1).sub.m --O--(alk.sub.2).sub.n --; each of (alk.sub.1) and (alk.sub.2) is C.sub.1 -C.sub.13 alkylene with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 13; each of m and n is 0 or 1; and W is H, pyridyl, phenyl, fluorophenyl or chlorophenyl; intermediates therefor and methods for their preparation and use.
    Type: Grant
    Filed: September 13, 1977
    Date of Patent: August 11, 1981
    Assignee: Pfizer Inc.
    Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4283565
    Abstract: There is described an essentially two step process for the preparation of benzylalcohols including those benzylalcohols having substituents on the benzyene ring by reaction of a substituted or unsubstituted benzyl halide with a formate typically an alkali or alkaline earth metal formate to form the corresponding substituted or unsubstituted benzyl formate. In the second step of the process the benzyl formate is contacted with an alcohol whereby the same is converted into the desired benzylalcohol. Both steps can be performed employing catalysts. Described in the specification is the realization of the desired product in exceptionally high yields in a short period of time whereby the process is characterized by high space-time yields.
    Type: Grant
    Filed: December 29, 1978
    Date of Patent: August 11, 1981
    Assignee: Dynamit Nobel AG
    Inventors: Gunther Bernhardt, Gerhard Daum
  • Patent number: 4273891
    Abstract: Hydroxy aromatic compositions containing (a) a hydroxyl group bonded directly to a carbon of an aromatic nucleus, (b) a hydrocarbon-based substituent of at least about 50 aliphatic carbon atoms bonded directly to a carbon atom of an aromatic nucleus, (c) at least one methylol or lower hydrocarbyl substituted methylol substituent bonded directly to a carbon atom of an aromatic nucleus, and not having any alkylene linkages between carbon atoms of two aromatic nuclei are useful as additives for normally liquid fuels and lubricating oils. These hydroxy aromatic compositions are also useful as intermediates for preparing other additives for fuels and lubricants. Typical hydroxy aromatic compositions of the present invention are formed by reaction of formaldehyde with an alkenyl- or alkyl-substituted phenol wherein the alkyl or alkenyl substituent contains an average of about 50 carbon atoms.
    Type: Grant
    Filed: September 6, 1977
    Date of Patent: June 16, 1981
    Assignee: The Lubrizol Corporation
    Inventors: John F. Pindar, Jerome M. Cohen, Charles P. Bryant
  • Patent number: RE37947
    Abstract: Novel pharmaceutically/cosmetically-active aromatic polyenic compounds have the structural formula (I): and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
    Type: Grant
    Filed: January 5, 2000
    Date of Patent: December 31, 2002
    Assignee: Centre International de Recherches Dermatologiques Galderma
    Inventors: Jean-Michel Bernardon, Phillippe Nedoncelle