Hydroxymethyl Group Containing Patents (Class 568/764)
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Patent number: 10744490Abstract: 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: GrantFiled: August 30, 2019Date of Patent: August 18, 2020Assignee: BASF CORPORATIONInventors: Keenan Lee Deutsch, Rostam J. Madon
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Publication number: 20150011801Abstract: 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: ApplicationFiled: July 8, 2013Publication date: January 8, 2015Applicant: Carter Technologies CorporationInventor: M. K. Carter
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Publication number: 20140256989Abstract: 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: ApplicationFiled: February 25, 2014Publication date: September 11, 2014Applicant: Wacker Chemie AGInventors: Benno KRUEGER, Gerald FLEISCHMANN, Hermann PETERSEN
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Publication number: 20140107319Abstract: 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: ApplicationFiled: December 20, 2013Publication date: April 17, 2014Applicants: JITSUBO Co., Ltd., National University Corporation, Tokyo University of Agriculture and TechnologyInventors: Kazuhiro Chiba, Shokaku Kim, Yusuke Kono
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Publication number: 20130245130Abstract: 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: ApplicationFiled: February 25, 2013Publication date: September 19, 2013Applicants: President and Fellows of Harvard College, Children's Medical Center CorporationInventors: Paula I. Watnick, Patrick Ymele-Leki, Jon Clardy, Shugeng Cao
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Publication number: 20130096209Abstract: 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: ApplicationFiled: April 15, 2011Publication date: April 18, 2013Applicants: Kraft Foods Global Brands LLC, Chromocell CorporationInventors: David Hayashi, William P. Jones, Jane V. Leland, Peter H. Brown, Joseph Gunnet, Daniel Lavery, Louise Slade, Kambiz Shekdar, Jessica Langer
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Patent number: 8017815Abstract: 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: GrantFiled: February 28, 2008Date of Patent: September 13, 2011Assignee: DSM IP Assets B.V.Inventors: Manfred Breuninger, Marcel Joray
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Publication number: 20100324343Abstract: 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: ApplicationFiled: February 28, 2008Publication date: December 23, 2010Inventors: Manfred Breuninger, Marcel Joray
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Patent number: 7148386Abstract: 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: GrantFiled: July 30, 2004Date of Patent: December 12, 2006Assignee: General Electric CompanyInventors: Jegadeesh Thampi, Sunil Ashtekar, Pramod Kumbhar, Rathinam Jothi Mahalingam
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Patent number: 7087799Abstract: 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: GrantFiled: January 31, 2003Date of Patent: August 8, 2006Assignee: Gun Ei Chemical Industry Co., Ltd.Inventors: Takeshi Tsuihiji, Michiyasu Yamazaki
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Patent number: 6806395Abstract: 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: GrantFiled: March 18, 2003Date of Patent: October 19, 2004Assignee: Kowa Co., Ltd.Inventors: Kimiyuki Shibuya, Tadaaki Ohgiya, Toru Miura, Kazuhiro Onogi
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Patent number: 6600078Abstract: 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: GrantFiled: August 12, 2002Date of Patent: July 29, 2003Assignee: Saudi Basic Industries CorporationInventors: Meftahuddin Mahmud, Ahmad Kamal Faizi, Vidyasagar Anchoori, Abdullah Al-Qahtani
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Patent number: 6554967Abstract: 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: GrantFiled: May 22, 2000Date of Patent: April 29, 2003Assignee: UBE Industries, Ltd.Inventors: Shuji Tanaka, Genji Koga, Hiroshi Kofuji, Tetsuro Kawashita
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Patent number: 6518315Abstract: 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: GrantFiled: June 23, 2000Date of Patent: February 11, 2003Assignee: The University of SydneyInventors: Basil Don Roufogalis, Colin Charles Duke, Van Hoan Tran
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Publication number: 20020198415Abstract: 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: ApplicationFiled: June 7, 2002Publication date: December 26, 2002Applicant: CREAGRI, INC.Inventor: Roberto Crea
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Patent number: 6414197Abstract: 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: GrantFiled: May 13, 1998Date of Patent: July 2, 2002Assignee: General Electric CompanyInventors: Leonid Modestovich Kustov, Viktor Ignatyevich Bogdan, Vladimir Borisovich Kazansky
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Patent number: 6380441Abstract: 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: GrantFiled: September 7, 2001Date of Patent: April 30, 2002Assignee: Bayer AktiengesellschaftInventors: Franz-Josef Mais, Herbert Diehl
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Publication number: 20020040168Abstract: 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: ApplicationFiled: May 13, 1998Publication date: April 4, 2002Inventors: LEONID MODESTOVICH KUSTOV, VIKTOR IGNATYEVICH BOGDAN, VLADIMIR BORISOVICH KAZANSKY
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Publication number: 20020032353Abstract: 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: ApplicationFiled: September 7, 2001Publication date: March 14, 2002Inventors: Franz-Josef Mais, Herbert Diehl
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Publication number: 20010004670Abstract: 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: ApplicationFiled: November 29, 2000Publication date: June 21, 2001Inventors: Roland Jacquot, Michel Spagnol
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Patent number: 6218431Abstract: 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: GrantFiled: July 31, 1997Date of Patent: April 17, 2001Assignees: Bayer Corporation, Bayer AktiengesellschaftInventors: 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
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Patent number: 6184421Abstract: 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: GrantFiled: May 13, 1999Date of Patent: February 6, 2001Assignee: Rhodia ChimieInventor: Pascal Metivier
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Patent number: 5811587Abstract: 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: GrantFiled: January 23, 1997Date of Patent: September 22, 1998Assignee: Rhone-Poulenc ChimieInventors: Claude Moreau, Sylvie Razigade-Trousselier, Annie Finiels, Francois Fajula, Laurent Gilbert
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Patent number: 5783737Abstract: 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: GrantFiled: January 24, 1997Date of Patent: July 21, 1998Assignee: Rhone-Poulenc ChimieInventor: Pascal Metivier
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Patent number: 5705167Abstract: 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: GrantFiled: April 26, 1995Date of Patent: January 6, 1998Assignee: Centre International de Recherches Dermatologiques GaldermaInventors: Jean-Michel Bernardon, Philippe Nedoncelle
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Patent number: 5563300Abstract: 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: GrantFiled: December 7, 1995Date of Patent: October 8, 1996Assignee: Hoechst Celanese CorporationInventors: James R. Sounik, Graham N. Mott, Charles B. Hilton, Mohammad Aslam
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Patent number: 5498804Abstract: 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: GrantFiled: March 17, 1995Date of Patent: March 12, 1996Assignee: Hoechst Celanese CorporationInventors: James R. Sounik, Graham N. Mott, Charles B. Hilton
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Patent number: 5393776Abstract: 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: GrantFiled: May 13, 1994Date of Patent: February 28, 1995Assignee: Bristol-Myers Squibb CompanyInventor: Bradley C. Pearce
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Patent number: 5041283Abstract: 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: GrantFiled: September 8, 1989Date of Patent: August 20, 1991Assignee: Kao CorporationInventors: Katsumi Kita, Tetsuo Uno, Shinichi Masuda, Kazuyuki Yahagi, Kazuhiro Tashiro
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Patent number: 5019656Abstract: 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: GrantFiled: February 27, 1990Date of Patent: May 28, 1991Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Hiroshi Iwane, Takahiro Sugawara, Naoki Suzuki
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Patent number: 4959391Abstract: 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: GrantFiled: July 14, 1988Date of Patent: September 25, 1990Assignee: Gruenenthal GmbHInventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin O. Kiesewetter, Ulrich G. P. Seippl
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Patent number: 4915875Abstract: 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: GrantFiled: November 4, 1986Date of Patent: April 10, 1990Assignee: The Dow Chemical CompanyInventors: Timothy R. Diephouse, Robert M. Strom
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Patent number: 4900354Abstract: 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: GrantFiled: August 29, 1986Date of Patent: February 13, 1990Assignee: The Dow Chemical CompanyInventors: James A. Turner, Paul S. Zorner, Wendy S. Jacks
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Patent number: 4879416Abstract: 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: GrantFiled: November 23, 1987Date of Patent: November 7, 1989Assignee: Eastman Kodak CompanyInventors: Thomas A. Puckette, Thomas J. Devon, Gerald W. Phillips, Jerome L. Stavinoha
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Patent number: 4849548Abstract: 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: GrantFiled: March 21, 1988Date of Patent: July 18, 1989Assignee: The Dow Chemical CompanyInventor: Ming-Biann Liu
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Patent number: 4760087Abstract: 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: GrantFiled: May 13, 1986Date of Patent: July 26, 1988Assignee: Gruenenthal GmbHInventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin Kiesewetter, Ulrich G. P. Seipp
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Patent number: 4590304Abstract: 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: GrantFiled: May 15, 1985Date of Patent: May 20, 1986Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: J. Shield Wallace, Fred E. Arnold
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Patent number: 4540833Abstract: 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: GrantFiled: March 21, 1984Date of Patent: September 10, 1985Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: J. Shield Wallace, Fred E. Arnold
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Patent number: 4460800Abstract: 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: GrantFiled: February 22, 1983Date of Patent: July 17, 1984Assignee: General Electric CompanyInventors: Charles M. Orlando, Howard J. Klopfer
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Patent number: 4460799Abstract: 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: GrantFiled: June 23, 1982Date of Patent: July 17, 1984Assignee: Isover Saint-GobainInventors: Robert Perrin, Roger Fugier
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Patent number: 4435601Abstract: 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: GrantFiled: July 7, 1981Date of Patent: March 6, 1984Assignee: Rhone-Poulenc IndustriesInventors: Karel Formanek, Daniel Michelet, Dominique Petre
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Patent number: 4408074Abstract: 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: GrantFiled: November 2, 1981Date of Patent: October 4, 1983Assignee: Dr. Lo. Zambeletti S.p.A.Inventors: Massimo Signorini, Attilio Trebbi, Luigi Molteni
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Patent number: 4318848Abstract: 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: GrantFiled: January 3, 1978Date of Patent: March 9, 1982Assignee: Bayer AktiengesellschaftInventors: Hans-Heinz Molls, Willy Schiwy, Reinhold Hornle, Reinhard Nebeling
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Patent number: 4301088Abstract: 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: GrantFiled: June 6, 1979Date of Patent: November 17, 1981Assignee: Dynamit Nobel AGInventor: Gunther Bernhardt
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Patent number: 4291178Abstract: 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: GrantFiled: July 5, 1979Date of Patent: September 22, 1981Assignee: Rhone-Poulenc IndustriesInventor: Joel L. Ludec
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Patent number: 4284829Abstract: 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: GrantFiled: December 22, 1978Date of Patent: August 18, 1981Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4283569Abstract: 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: GrantFiled: September 13, 1977Date of Patent: August 11, 1981Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4283565Abstract: 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: GrantFiled: December 29, 1978Date of Patent: August 11, 1981Assignee: Dynamit Nobel AGInventors: Gunther Bernhardt, Gerhard Daum
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Patent number: 4273891Abstract: 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: GrantFiled: September 6, 1977Date of Patent: June 16, 1981Assignee: The Lubrizol CorporationInventors: John F. Pindar, Jerome M. Cohen, Charles P. Bryant
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Patent number: RE37947Abstract: 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: GrantFiled: January 5, 2000Date of Patent: December 31, 2002Assignee: Centre International de Recherches Dermatologiques GaldermaInventors: Jean-Michel Bernardon, Phillippe Nedoncelle