Nitrogen, Phosphorus, Or Sulfur Containing Reactant Patents (Class 554/154)
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Patent number: 12152005Abstract: Processes are disclosed for preparing carboxylic acids from organic esters, the processes comprising contacting an ester with water in the presence of an acid catalyst and a homogenizing solvent at conditions effective to form a carboxylic acid. The homogenizing solvent is present in an amount sufficient to form a single-phase reaction mixture comprising the ester, water, and homogenizing solvent. The homogenizing solvent may be selected from acetonitrile, dimethyl sulfoxide, and 1,4-dioxane.Type: GrantFiled: March 25, 2020Date of Patent: November 26, 2024Assignee: Eastman Chemical CompanyInventors: Damon Ray Billodeaux, Kenneth Wayne Hampton, Jr., Magnus Alexander Pauly
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Patent number: 10604712Abstract: This application relates to phase behaviors of certain triacylglycerols and fatty acid methyl esters, and how the phase behaviors of these individual components in a biodiesel fuel, as well as their combined mixtures, helps understand the fundamental mechanisms of their crystallization so as to design biodiesel fuels with improved low temperature characteristics.Type: GrantFiled: April 15, 2013Date of Patent: March 31, 2020Assignee: Trent UniversityInventors: Suresh Narine, Laziz Bouzidi, Bruce Darling, Mark Baker, Shaojun Li, Ali Mahdevari
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Patent number: 9670126Abstract: The present disclosure provides methods of making 15-hydroxy fatty acid derivatives, such as 15-(S)-hydroxyeicosatrienoic acid (HETrE or 15-(S)-HETrE) or 15(S)-hydroxyeicosapentaenoic acid (HEPE or 15(S)-HEPE) from the corresponding fatty acid (e.g., dihomo-?-linolenic acid (DGLA) or eicosapentaenoic acid (EPA), respectively). In some embodiments, the method comprises contacting the fatty acid with an oxidizing agent (e.g., a lipoxygenase and oxygen) in the presence of a reducing agent (e.g., cysteine) to form the 15-hydroxy fatty acid derivatives in a single reaction vessel.Type: GrantFiled: October 29, 2014Date of Patent: June 6, 2017Assignee: DIGNITY SCIENCES LIMITEDInventors: Mehar Manku, David Coughlan, Bill Downes
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Patent number: 9221745Abstract: A process for synthesizing a long-chain saturated ?,?-amino ester (acid) including from 6 to 17 carbon atoms, said process including a first step of cross metathesis between a first acrylic compound chosen from acrylonitrile, acrylic acid or an acrylic ester and a second monounsaturated compound including at least one nitrile, acid or ester trivalent function, one of these compounds including a nitrile function and the other an acid or ester function, in the presence of a ruthenium carbene metathesis catalyst, and a second step of hydrogenation of the monounsaturated nitrile-ester (acid) obtained, wherein said monounsaturated compound including at least one nitrile, acid or ester trivalent function has previously been subjected to a purification by thermal and/or chemical treatment.Type: GrantFiled: July 27, 2012Date of Patent: December 29, 2015Assignee: ARKEMA FRANCEInventors: Jean-Luc Couturier, Jean-Luc Dubois
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Patent number: 9181507Abstract: This application relates to phase behaviors of certain triacylglycerols and fatty acid methyl esters, and how the phase behaviors of these individual components in a biodiesel fuel, as well as their combined mixtures, helps understand the fundamental mechanisms of their crystallization so as to design biodiesel fuels with improved low temperature characteristics.Type: GrantFiled: April 15, 2013Date of Patent: November 10, 2015Assignee: Trent UniversityInventors: Suresh Narine, Laziz Bouzidi, Bruce Darling, Mark Baker, Shaojun Li, Ali Mahdevari
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Patent number: 9079847Abstract: There is provided a process for purifying a fatty acid, which process comprises reacting a fatty acid with a lithium salt in a first solution and under conditions to allow formation of a precipitate of a lithium salt of the fatty acid; isolating the precipitate; dissolving the precipitate in a second solution followed by separation of the organic and aqueous layers so formed; and evaporating the organic layer to isolate the purified fatty acid. There is also provided a process for increasing the length of a fatty acid, and the use of a lithium salt to purify a fatty acid.Type: GrantFiled: January 27, 2011Date of Patent: July 14, 2015Assignee: BASF PHARMA (CALLANISH) LIMITEDInventors: Adam Kelliher, Angus Morrison, Phil Knowles
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Publication number: 20150119593Abstract: The present disclosure provides methods of making 15-hydroxy fatty acid derivatives, such as 15-(S)-hydroxyeicosatrienoic acid (HETrE or 15-(S)-HETrE) or 15(S)-hydroxyeicosapentaenoic acid (HEPE or 15(S)-HEPE) from the corresponding fatty acid (e.g., dihomo-?-linolenic acid (DGLA) or eicosapentaenoic acid (EPA), respectively). In some embodiments, the method comprises contacting the fatty acid with an oxidizing agent (e.g., a lipoxygenase and oxygen) in the presence of a reducing agent (e.g., cysteine) to form the 15-hydroxy fatty acid derivatives in a single reaction vessel.Type: ApplicationFiled: October 29, 2014Publication date: April 30, 2015Inventors: Mehar Manku, David Coughlan, Bill Downes
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Publication number: 20150094481Abstract: The invention is directed to methods of making organic compounds by metathesis and hydrocyanation. Hydrocyanation functions to introduce a nitrile group into the organic compound. The nitrile group may be converted into an amine group, an aldehyde group, an alcohol group, or a carboxylic acid group. The method of the invention may be used, for example, to make industrial important organic compounds such as diacids, diesters, acid-amines, acid-alcohols, acid-nitriles, ester-amines, ester-alcohols, and ester-nitriles.Type: ApplicationFiled: October 13, 2014Publication date: April 2, 2015Applicant: ELEVANCE RENEWABLE SCIENCES, INC.Inventors: Timothy W. Abraham, Hiroki Kaido, Choon Woo Lee, Richard L. Pederson, Yann Schrodi, Michael John Tupy, Alexandre A. Pletnev
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Publication number: 20140373432Abstract: A method of producing fatty acid esters in situ from microbial biomass such as algae is provided by treating microbial biomass with a solution containing an alcohol and at least one ?-hydroxysulfonic acid. Fatty acid ester can be directly recovered from the treated microbial biomass. The ?-hydroxysulfonic acid can be easily removed from the treated microbial biomass and recycled.Type: ApplicationFiled: June 23, 2014Publication date: December 25, 2014Inventors: Pen-Chung WANG, Paul Richard WEIDER, Robert Lawrence BLACKBOURN, Joseph James ALISHUSKY
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Patent number: 8692008Abstract: The present invention relates to a process for preparing fatty acid esters and/or fatty acid ester mixtures of monohydric alcohols having 1 to 5 carbon atoms by transesterifying fatty acid glycerides with monohydric alcohols in the presence of a basic catalyst, in the course of which methanesulfonic acid is used. The invention further relates to the use of methanesulfonic acid for preparing these fatty acid esters.Type: GrantFiled: November 16, 2009Date of Patent: April 8, 2014Assignee: BASF SEInventor: Stefan Fabβbender
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Publication number: 20140051876Abstract: Provided is a method of manufacturing a high quality phosphonocrotonic acid derivative. The present invention is a method of manufacturing a compound represented by the following Formula (3) by reacting a compound represented by the following Formula (1) with a compound represented by the following Formula (2), which comprises a treatment process using an acid or base. [in the formula, R1 represents a C1-6 linear or branched alkyl group that may be substituted by a C6-10 aryl group, a C2-6 linear or branched alkenyl group that may be substituted by a C6-10 aryl group, a C2-6 linear or branched alkynyl group that may be substituted by a C6-10 aryl group, or a C6-10 aryl group, R2 represents a hydrogen atom, or a C1-6 linear or branched alkyl group that may be substituted by a C6-10 aryl group, R3 represents a C1-6 linear or branched alkyl group, a C6-10 aryl group, or a halogen atom, and X represents a halogen atom, and multiple R1s may be the same or different].Type: ApplicationFiled: April 26, 2012Publication date: February 20, 2014Applicants: MANAC Incorporated, KOWA COMPANY, LTD.Inventors: Shinji Ina, Takahiro Yamazaki, Junichi Sakata, Koji Ezaki, Katsuhiro Sakamoto
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Publication number: 20140012024Abstract: A method for preparing docosahexaenoic acid (DHA). The method comprises coupling a compound represented by Formula I with a compound represented by Formula II followed by partial hydrogenation to obtain a compound represented by Formula III. The compound represented by Formula III acts as a DHA precursor and thus can be hydrolysed to obtain DHA. Novel starting materials represented by Formula I and Formula II, and synthetic routes for preparing the same are also provided.Type: ApplicationFiled: March 16, 2012Publication date: January 9, 2014Applicant: PHENOMENOME DISCOVERIES INC.Inventors: Mohamed Amin Khan, Paul L. Wood
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Publication number: 20130310587Abstract: A process for preparing saturated branched chain fatty acids or alkyl esters thereof involving subjecting unsaturated fatty acids having 10 to 25 carbon atoms, alkyl esters thereof or mixtures thereof to a skeletal isomerization reaction in the presence of water or a lower alcohol at a temperature of about 240° C. to about 280° C. using a combination of a sterically hindered Lewis base and zeolite as a Brönsted or Lewis acid catalyst, and isolating saturated branched chain fatty acids or alkyl esters thereof or mixtures thereof from the reaction mixture obtained by the skeletal isomerization reaction; wherein the process further comprises (a) recycling said catalyst by washing said catalyst with an acid solution at about 55° C. for about 24 hours, recovering the catalyst followed by heating the catalyst at about 115° C. for about 20 hours for the first four or five cycles of use and (b) in the next subsequent cycle recycling the catalyst by heating the catalyst at about 115° C.Type: ApplicationFiled: July 25, 2013Publication date: November 21, 2013Inventors: Helen Ngo, Thomas A. Foglia
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Publication number: 20130296573Abstract: A protected organoboronic acid includes a boron having an sp3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. A method of performing a chemical reaction includes contacting a protected organoboronic acid with a reagent, the protected organoboronic acid including a boron having an sp3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. The organic group is chemically transformed, and the boron is not chemically transformed.Type: ApplicationFiled: October 18, 2012Publication date: November 7, 2013Applicant: The Board of Trustees of the University of IllinoisInventors: Martin D. Burke, Eric P. Gillis, Suk Joong Lee, David M. Knapp, Kaitlyn C. Gray
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Publication number: 20130192784Abstract: The present invention relates to a process for the production of a surface-treated calcium carbonate, the use of this surface-treated calcium carbonate in a process for the control of organic material in an aqueous medium, as well as to a composite of surface-treated calcium carbonate and organic material, such as a composite of surface-treated calcium carbonate and to the use of such a composite.Type: ApplicationFiled: July 12, 2011Publication date: August 1, 2013Inventors: Matthias Buri, Samuel Rentsch, Patrick A.C. Gane, Daniel Gantenbein, Joachim Schölkopf
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Publication number: 20130150602Abstract: There is provided a process for purifying a fatty acid, which process comprises reacting a fatty acid with a lithium salt in a first solution and under conditions to allow formation of a precipitate of a lithium salt of the fatty acid; isolating the precipitate; dissolving the precipitate in a second solution followed by separation of the organic and aqueous layers so formed; and evaporating the organic layer to isolate the purified fatty acid. There is also provided a process for increasing the length of a fatty acid, and the use of a lithium salt to purify a fatty acid.Type: ApplicationFiled: January 27, 2011Publication date: June 13, 2013Applicant: BASF PHARMA (CALLANISH) LIMITEDInventors: Adam Kelliher, Angus Morrison, Phil Knowles
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Patent number: 8269027Abstract: The invention relates to trans carotenoid salt compounds, methods for making them, methods for solubilizing them and uses thereof. These compounds are useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans.Type: GrantFiled: April 27, 2007Date of Patent: September 18, 2012Assignee: Diffusion Pharmaceuticals LLCInventors: John L. Gainer, Raymond C. Grabiak
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Publication number: 20120177724Abstract: The invention provides delivery systems comprised of stabilized multilamellar vesicles, as well as compositions, methods of synthesis, and methods of use thereof. The stabilized multilamellar vesicles comprise terminal-cysteine-bearing antigens or cysteine-modified antigens, at their surface and/or internally.Type: ApplicationFiled: February 19, 2012Publication date: July 12, 2012Applicant: Massachusetts Institute of TechnologyInventors: Darrell J. Irvine, Anjali Yadava, Jaehyun Moon
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Publication number: 20120065260Abstract: Compounds of formula (I); wherein R1 and R2 are the same or different and may be selected from the group consisting of a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, and an alkylamino group; and X represents a carboxylic acid group, a carboxylate group, or a carboxamide group; or any pharmaceutically acceptable salt, solvate, complex or pro-drug thereof, with the provisos that the compound of formula (I) is not (all-Z)-4,7,10,13,16,19-docosahexaenoic acid (DHA), alpha-methyl DHA, alpha-methyl DHA methyl ester, alpha-methyl DHA ethyl ester or alpha-hydroxy DHA ethyl ester, are disclosed. A fatty acid composition and a pharmaceutical composition comprising such compounds are also disclosed.Type: ApplicationFiled: September 6, 2011Publication date: March 15, 2012Inventors: Morten Bryhn, Jan Kopecky, Anne Kristin Holmeide
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Publication number: 20110300281Abstract: The present invention relates to a method for producing fatty acid esters from fats and/or oils of biogenic origin by transesterification with monovalent or polyvalent alcohols in the presence of a special hydroxy-functional quaternary ammonium compound as the catalyst.Type: ApplicationFiled: October 21, 2009Publication date: December 8, 2011Applicants: Balchem Corporation, Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung E.V.Inventors: Eckhard Weidner, Axel Kraft, Anna Grevé, Reinhard Broucek
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Publication number: 20110263884Abstract: A process for preparing saturated branched chain fatty acids or alkyl esters thereof involving subjecting unsaturated fatty acids having 10 to 25 carbon atoms, alkyl esters thereof or mixtures thereof to a skeletal isomerization reaction in the presence of water or a lower alcohol at a temperature of about 240° C. to about 280° C. using a combination of a stericly hindered Lewis base and zeolite as a Brönsted or Lewis acid catalyst, and isolating saturated branched chain fatty acids or alkyl esters thereof or mixtures thereof from the reaction mixture obtained by the skeletal isomerization reaction. The yield of said saturated branched chain fatty acids is ?70 wt %. The stericly hindered Lewis base is a tertiary amine or phosphine with linear or branched C1 to C6 alkyl or phenyl groups attached thereto.Type: ApplicationFiled: April 26, 2010Publication date: October 27, 2011Inventors: Helen Ngo, Thomas A. Foglia
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Publication number: 20110245521Abstract: The present invention relates to a process for preparing fatty acid esters and/or fatty acid ester mixtures of monohydric alcohols having 1 to 5 carbon atoms by transesterifying fatty acid glycerides with monohydric alcohols in the presence of a basic catalyst, in the course of which methanesulfonic acid is used. The invention further relates to the use of methanesulfonic acid for preparing these fatty acid esters.Type: ApplicationFiled: November 16, 2009Publication date: October 6, 2011Applicant: BASF SEInventor: Stefan Fassbender
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Publication number: 20110160472Abstract: Various methods are provided for metathesizing a feedstock. In one aspect, a method includes providing a feedstock comprising a natural oil, chemically treating the feedstock under conditions sufficient to diminish catalyst poisons in the feedstock, and, following the treating, combining a metathesis catalyst with the feedstock under conditions sufficient to metathesize the feedstock.Type: ApplicationFiled: August 11, 2008Publication date: June 30, 2011Applicant: Elevance Renewable Sciences, Inc.Inventors: Daniel W. Lemke, Kevin D. Uptain, Francis Amore, Tim Abraham
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Publication number: 20110146142Abstract: Disclosed herein are various embodiments regarding the production of fatty acid methyl esters. Disclosed herein are various embodiments regarding the use of methanol compositions for the production of fatty esters.Type: ApplicationFiled: August 20, 2009Publication date: June 23, 2011Applicant: LS9, INC.Inventors: Grace J. Lee, Zhihao Hu
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Publication number: 20100305344Abstract: The present disclosure relates to a process for the production of a base complex catalyst comprising reacting a hydroxide base with a polyalcohol, under vacuum pressure, at a temperature in the range of about 60° C. to about 220° C., wherein the mole ratio of the hydroxide base to the polyalcohol is greater than about 2:1.Type: ApplicationFiled: December 1, 2008Publication date: December 2, 2010Applicant: UNIVERSITY OF SASKATCHEWANInventors: Martin J.T. Reaney, Jianheng Shen, Douglas W. Soveran
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Publication number: 20070299271Abstract: A process for separating a blend of saturated and unsaturated fatty acids or saturated and unsaturated fatty acid alkyl esters into a first fraction enriched with the saturated fatty acids or saturated fatty acid alkyl esters and a second fraction enriched with unsaturated fatty acids or unsaturated fatty acid alkyl esters. When separating fatty acids, the process includes the steps of (a) saponifying a blend of long chain saturated and unsaturated fatty acids to form free fatty acids, (b) complexing the free fatty acids with urea, and (c) separating the urea complexed free fatty acids into a first fraction enriched with saturated free fatty acids and a second fraction enriched with unsaturated free fatty acids.Type: ApplicationFiled: June 27, 2006Publication date: December 27, 2007Inventors: Udaya Nayanskantha Wanasundara, Roger Peterson
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Patent number: 7126016Abstract: A fluorocarboxylic acid preparation process continuously carries out acidification reaction treatment and washing treatment, and includes subjecting a fluorocarboxylate-containing aqueous solution to acidification reaction treatment in the presence of sulfuric acid so as to form a sulfate-containing fluorocarboxylic acid phase; and subjecting the fluorocarboxylic acid phase to washing treatment using an aqueous sulfuric acid solution.Type: GrantFiled: March 24, 2005Date of Patent: October 24, 2006Assignees: E.I. DuPont De Nemours and Company, Daikin Industries, Ltd.Inventors: Ta-Wei Fu, Steven H. Swearingen, Takuya Ichida, Shuji Itatani
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Patent number: 6984742Abstract: A method for preparing a polyprenyl compound wherein an aldehyde represented by the following general formula [I]: [wherein n represents an integer of from 0 to 3]and a Wittig reagent represented by the following general formula [II]: [wherein each of R1 and R2 represents a group consisting of hydrocarbon] are reacted in a medium as a mixture of water and an organic solvent in the presence of a base, and further in the presence of a crown ether. Said method achieves an excellent selectivity and a high yield.Type: GrantFiled: April 16, 2004Date of Patent: January 10, 2006Assignee: Nikken Chemicals Co., Ltd.Inventors: Shin Tanikawa, Mao Yamashita
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Patent number: 6800771Abstract: The invention relates to stabilized amido acid compositions. More particularly, the invention relates to compositions of amido acids, such as 6-nonanoylamidohexanoic acid, stabilized with antioxidants. The stabilized amido acid compositions are useful in the manufacture of bleach activators such as sodium nonanamidohexanoyloxybenzenesulfonate. Bleach activators made from the stabilized amido acids of the invention are capable of possessing improved coloration.Type: GrantFiled: September 3, 2003Date of Patent: October 5, 2004Inventors: Dale Elbert Van Sickle, George Chester Zima, Jeffrey Scott DuPont, Robert Richard Dykstra
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Patent number: 6479684Abstract: The present invention generally relates to a process for hardening lipids, especially unsaturated lipids such as unsaturated fatty oils, by mixing and interacting lipids with polyamines such that the peak melting point of the resulting combination is higher than that of the lipid alone. In this way, the polyamine-treated unsaturated lipid can be converted into a solid or semi-solid state at a relatively lower temperature than the unsaturated lipid alone. The lipid and polyamine combination displays physical attributes that mimic the crystalline structures of saturated lipids and fats without the incurring the associated negative health implications of such saturated lipids and fats.Type: GrantFiled: March 6, 2001Date of Patent: November 12, 2002Assignee: Kraft Foods Holdings, Inc.Inventors: Ahmad Akashe, Manuel Marquez
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Patent number: 6436244Abstract: Fluorinated emulsifier acids bound to an anion exchanger resin can be eluted using a mixture of water, a compound of the formula M—X, in which M is an alkali metal or an alkylammonium ion, and X is hydroxyl, fluoride or chloride, and at least one organic solvent which completely dissolves the other components. For work-up of the eluent, this is advantageously subjected to steam distillation until all volatile constituents have been essentially removed, and the emulsifier acid is liberated from the steam distillation residue using a sufficiently strong acid. This emulsifier acid can advantageously be distilled off and collected as the ammonium salt in aqueous ammonia solution.Type: GrantFiled: June 30, 2000Date of Patent: August 20, 2002Assignee: Dyneon GmbHInventors: Stephan Führer, Gernot Löhr, Werner Schwertfeger
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Patent number: 6392073Abstract: Novel intermediates, i.e., N-(2S-(2-propenyl)octanoyl)-(1S)-(−)-2, 10-camphorsultam, N-(2S-(2-propynyl)octanoyl)-(1S)-(−)-2,10-camphorsultam and N-(2R-(2-propyl)octanoyl)-(1S)-(−)-2,10-camphorsultam; processes for the preparation of the intermediates; and processes for the preparation of optically active 2S-(2-propenyl)octanoic acid, 2S-(2-propynyl)octanoic acid and 2R-propyloctanoic acid by using the same. Optically active 2R-propyloctanoic acid equivalent or superior to that prepared by the process of the prior art in optical purity can be efficiently prepared in shorter reaction steps.Type: GrantFiled: September 7, 2001Date of Patent: May 21, 2002Assignee: Ono Pharmaceutical Co., Ltd.Inventor: Hisashi Yamamoto
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Patent number: 6376688Abstract: The present invention provides polyunsaturated fatty acid compounds having antimalarial and/or neutrophil stimulatory activity. The polyunsaturated fatty acids contain 18-25 carbons and 1-6 double bonds and are characterized in that they have one or two substitutions selected from the group consisting of &bgr; oxa, &ggr; oxa, &bgr; thia and &ggr; thia. It is also preferred that the polyunsaturated fatty acid compound includes a further substitution selected from the group consisting of hydroxy, hydroperoxy, peroxy, carboxymethyl substitutions or attached to an amino acid.Type: GrantFiled: May 29, 1997Date of Patent: April 23, 2002Assignee: Peptide Technology LimitedInventors: Antonio Ferrante, Alfred Poulos, Christopher John Easton, Michael Joseph Pitt, Thomas Alistair Robertson, Deborah Ann Rathjen
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Patent number: 6215009Abstract: The invention provides a process for the manufacture of a retinyl acylate of the formula I: wherein R1 is an optionally substituted C1-23-alkyl, a C2-23-alkenyl having 1 to 5 double bonds, an optionally aromatically substituted phenyl-C1-6-alkyl, or an optionally substituted phenyl. This process includes treating a compound of formula II: wherein R1 is defined above and R2 is hydrogen or COR1, with an agent that is an acid anhydride or a complex of sulfur trioxide in the presence of dimethylformamide. In addition to dimethylformamide, an aprotic organic solvent may optionally be present in the reaction. The products of the present invention are useful as intermediates for the manufacture of compounds of the vitamin A group or in certain cases as the compounds themselves.Type: GrantFiled: January 18, 2000Date of Patent: April 10, 2001Assignee: Roche Vitamins Inc.Inventors: Stefan Bischof, David Carl Burdick, Bernard Orsat
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Patent number: 6160141Abstract: A synthesis process for producing 11-cis, 13-trans eicosadienoic acid at room temperature in high yield is disclosed, including providing a tosylate or mesylate of a methyl lesquerolate and 11-cis, 13-trans eicosadienoic acid formed when the tosylate or mesylate reacts with diazabicyclo-undecene. In one aspect, the tosylate of the methyl lesquerolate is formed with tosyl chloride in a pyridine solvent. In one aspect, the mesylate of the methyl lesquerolate is formed with mesyl chloride in acetonitrile and triethyl amine. In one aspect, the tosylate or mesylate is reacted with diazabicyclo-undecene in a polar, non-hydroxylic solvent of acetonitrile to form the preferred isomer of 11-cis, 13-trans eicosadienoic acid at room temperature in high yield.Type: GrantFiled: April 1, 1999Date of Patent: December 12, 2000Inventor: Michael C. Seidel
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Patent number: 5932696Abstract: A method for the solid phase preparation of an amine by a novel synthesis is described where a diol is monoalkylated with a chloromethyl resin followed by reaction with N,N'-carbonyldimidazole to afford a resin-bound tertiary-alkoxycarbonyl-imidazole which is subsequently N-alkylated and then sequentially treated with appropriate building blocks and reagents to afford a resin-bound amine which affords the desired amine after treatment with an acid as well as other valuable intermediates used in the process.Type: GrantFiled: October 7, 1998Date of Patent: August 3, 1999Assignee: Warner-Lambert CompanyInventors: John Cooke Hodges, Andres Sergio Hernandez
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Patent number: 5892074Abstract: A synthesis process for producing 9-cis, 11-trans octadecadienoic acid at room temperature in high yield is disclosed, including providing a tosylate or mesylate of a methyl ester of ricinoleic acid and 9-cis, 11-trans octadecadienoic acid formed when the tosylate or mesylate reacts with diazabicyclo-undecene. In one aspect, the tosylate of the methyl ester of ricinoleic acid is formed with tosyl chloride in a pyridine solvent. In one aspect, the mesylate of the methyl ester of ricinoleic acid is formed with mesyl chloride in acetonitrile and triethyl amine. In one aspect, the tosylate or mesylate is reacted with diazabicyclo-undecene in a polar, non-hydoxylic solvent of acetonitrile to form the preferred isomer of 9-cis, 11-trans octadecadienoic acid at room temperature in high yield.Type: GrantFiled: February 18, 1997Date of Patent: April 6, 1999Inventor: Michael C. Seidel
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Patent number: 5817845Abstract: Methods for stereospecific synthesis of 9-cis olefins and retinoids. In one particular aspect, a cis olefin is generated via a lactol ring opening with complete retention of double bond configuration.Type: GrantFiled: October 9, 1996Date of Patent: October 6, 1998Assignee: Ligand Pharmaceuticals, Inc.Inventors: Steven K. White, Chan Kou Hwang, David T. Winn
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Patent number: 5808120Abstract: A method of synthesizing 9-cis-retinoic acid, all-trans-retinoic acid or 9-nor-retinoic acid is disclosed. The method comprises the steps of adding a Grignard reagent of ##STR1## to 2,2,6 trimethyl cyclohexanone is disclosed. R is a methyl group or H and the CH.sub.2 --OH group is in either the cis or trans orientation relative to the HC.tbd.C- group. The resulting product is converted into retinoic acid. In the preferable form of the present invention, a tritium-labelled retinoic acid is synthesized, wherein the labelling is at the C.sub.20 position. A preparation of tritium-labelled 9-cis-retinoic acid with a specific activity of greater than 65 Ci/mmol is also enclosed. In a most preferred embodiment, the specific activity is greater than 75 Ci/mmol.Type: GrantFiled: August 22, 1995Date of Patent: September 15, 1998Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Praveen K. Tadikonda
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Patent number: 5723639Abstract: A low temperature method for esterifying ammonium- and amine-containing salts is provided whereby the salt is reacted with an alcohol in the presence of heat and a catalyst and then subjected to a dehydration and deamination process using pervaporation.The invention also provides for a method for producing esters of fermentation derived, organic acid salt comprising first cleaving the salt into its cationic part and anionic part, mixing the anionic part with an alcohol to create a mixture; heating the mixture in the presence of a catalyst to create an ester; dehydrating the now heated mixture; and separating the ester from the now-dehydrated mixture.Type: GrantFiled: October 16, 1995Date of Patent: March 3, 1998Assignee: University of ChicagoInventors: Rathin Datta, Shih-Perng Tsai
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Patent number: 5646320Abstract: Fatty acid esters of isethionate salts are made by reacting ethylene oxide and a bisulfite salt, that may be made in situ, in aqueous ammonia while maintaining (1) the pH in the range of about 5.5 to about 6.5 and (2) the temperature in the range of 25.degree. C. to 85.degree. C. to form an isethionate salt. The isethionate salt is then esterified with a fatty acid to produce a product having little or no unwanted fatty acid esters of ethylene glycol.Type: GrantFiled: June 16, 1994Date of Patent: July 8, 1997Assignee: Henkel CorporationInventors: Timothy John Cassady, Norman Milstein, Richard P. Crews
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Patent number: 5508456Abstract: Methods for the synthesis of 9-cis monotritium-labeled retinoids, and their use in the discovery of Retinoid X Receptor ligands are provided. In addition, 9-cis monotritium-labeled retinoids, as well as novel intermediates and tritium-labeled intermediates formed during the synthesis of 9-cis monotritium-labeled retinoids are also provided.Type: GrantFiled: May 27, 1994Date of Patent: April 16, 1996Assignee: Ligand Pharmaceuticals IncorporatedInventor: Marcus F. Boehm
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Patent number: 5504230Abstract: A process for preparing 9-(Z)-retinoic acid from mother liquors from the industrial preparation of C.sub.15 -triarylphosphonium salts of the general formula I ##STR1## where R.sup.1 to R.sup.3 are each aryl and X.sup..crclbar. is halogen or (HSO.sub.4).sup..crclbar., in an organic solvent, which comprisesA. increasing the proportion of 9-(Z)-C.sub.15 -triarylphosphonium salt in the C.sub.15 -triarylphosphonium salts isolated from the mother liquor by treatment with isopropanol at elevated temperature, cooling and separating off the all-(E)-C.sub.15 -triarylphosphonium salt which has crystallized out,B. subjecting the resulting C.sub.15 -triarylphosphonium salt to a Wittig reaction with an alkyl .beta.-formylcrotonate of the general formula ##STR2## and C. hydrolyzing the resulting oily retinoic ester mixture in a C.sub.3 -C.sub.Type: GrantFiled: December 16, 1994Date of Patent: April 2, 1996Assignee: BASF AktiengesellschaftInventors: Michael John, Joachim Paust
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Patent number: 5502226Abstract: A new synthesis of .omega.-hydroxy acids, which employs commercially available starting materials and lowers the cost of production. The process involves coupling a fatty acyl group by enamine chemistry, followed by a ring expansion and selective reduction of ketoacid.Type: GrantFiled: November 14, 1994Date of Patent: March 26, 1996Assignee: Elizabeth Arden Co., Division of Conopco, Inc.Inventors: Suk H. Cho, Victor DeFlorio
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Patent number: 5498786Abstract: This invention relates to novel processes for synthesizing intermediates in the preparation of N-aryl and N-heteroarylamide inhibitors of the enzyme acyl coenzyme A: cholesterol acyltransferase (ACAT), and to novel intermediates used in such processes.Type: GrantFiled: September 13, 1993Date of Patent: March 12, 1996Assignee: Pfizer Inc.Inventors: Sarah E. Kelly, George Chang
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Patent number: 5498733Abstract: Nylon-11 monomer, 11-aminoundecanoic acid, is synthesized from 12-oxododecanoic acid oxime in a three-step reaction sequence which involves a Beckmann rearrangement, Hofmann degradation and hydrolysis. The aldoxime acid is hydrolyzed in the presence of nickel acetate tetrahydrate to give 11-carbamoylundecanoic acid. This amide is then treated with a solution of sodium methoxide and bromine at 70.degree.-80.degree. C. to give 11-(methoxycarbonylamino)undecanoic acid, which upon basic hydrolysis and subsequent neutralization, yields the 11-aminoundecanoic acid.Type: GrantFiled: July 19, 1993Date of Patent: March 12, 1996Assignee: Howard UniversityInventors: Folahan O. Ayorinde, Chukwuma P. Nwaonicha
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Patent number: 5442107Abstract: A process for preparing a carboxylic acid having (n+1) carbon atoms (e.g. acetic acid) from an alcohol having n carbon atoms (e.g. methanol) by liquid phase, rhodium catalyses carbonylation is provided. The process is characterized by using a catalyst stabilizer selected from certain classes of imidazolium iodides, alkyl substituted pyridinium iodides and hydroxypyridinium iodides. Most preferred are those derived from the amines 2-ethyl-4-methyl imidazole, 4-ethylpyridine, 4-t-butylpyridine and 3,4-lutidine by quarternisation with a methyl group.Type: GrantFiled: September 28, 1993Date of Patent: August 15, 1995Assignee: BP Chemicals LimitedInventors: Robert G. Beevor, David J. Gulliver
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Patent number: 5440061Abstract: The present invention relates to an improved process for preparing fatty acids from alkyl, preferably methyl esters comprising mixing the fatty acid ester with water, acid catalyst, and DMSO in order to form a single phase reaction mixture. The single phase reaction mixture is then heated to a temperature of from about 70.degree. C. to about 130.degree. C. to hydrolyze the fatty acid ester into the corresponding acid and volatile alcohol and removing the volatile alcohol. The acid catalyst is heat and water stable and the reaction mixture is essentially free of C.sub.2 -C.sub.5 carboxylic acids. The initial stoichiometric ratio of the water to the ester is at least about 1:1.Type: GrantFiled: March 29, 1994Date of Patent: August 8, 1995Assignee: The Procter & Gamble CompanyInventor: Michael S. Gibson
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Patent number: 5393901Abstract: This invention relates to a process for preparing amido-carboxylic acids in water wherein hydrolysis and amidation reactions are conducted simultaneously in a single vessel. The process involves three steps. The first step involves heating at a temperature of 150.degree. C.-300.degree. C. for 2 to 10 hours, a mixture containing water, a nitrogen containing compound selected from the group consisting of a lactam and an amino acid, and a carboxylic acid or ester. The second step involves cooling the reaction mixture to obtain a two phase system containing an aqueous layer and an organic layer. The third step involves separating the amido-carboxylic acid containing organic layer from the aqueous layer. The presence of water aids in product isolation by phase separation and recycle of the reactants.Amido-carboxylic acids are used to make bleach activators for detergents.Type: GrantFiled: April 15, 1994Date of Patent: February 28, 1995Assignee: Eastman Chemical CompanyInventors: George C. Zima, T. Hugh Williams, Gary P. Lutz, William C. Dickason
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Patent number: RE39333Abstract: This invention provides a process for producing a 5-hydroxy-3-oxopentanoic acid, a useful pharmaceutical intermediate, easily from a readily available, inexpensive starting material without using any extraordinary production equipment such as a very-low-temperature reactor. Thus, this invention provides a process for producing a 5-hydroxy-3-oxopentanoic acid which comprises permitting a lithium amide to act upon a mixture of an acetic acid ester and a 3-hydroxypropionic acid derivative at not below ?20° C. Further, this invention also provides a process for producing a 5-hydroxy-3-oxopentanoic acid which comprises treating a mixture of an acetic acid ester and a 3-hydroxypropionic acid derivative with a Grignard reagent to prepare a mixture of a compound and an acetic acid ester of the above formula (I), and permitting a lithium amide to act upon the mixture at a temperature not below ?20° C.Type: GrantFiled: June 2, 2000Date of Patent: October 10, 2006Assignee: Kaneka CorporationInventors: Akira Nishiyama, Kenji Inoue