Preparing From A Cyclic Ketone (i.e., A Ketone Where The Carbonyl Is Part Of A Ring) Patents (Class 549/272)
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Patent number: 11325887Abstract: The present invention relates generally to methods for forming peroxyformic acid, comprising contacting formic acid with hydrogen peroxide. The methods for forming peroxyformic acid can include adding formic acid with a relatively lower concentration of hydrogen peroxide, or adding formic acid to a peroxycarboxylic acid composition or forming composition to react with hydrogen peroxide in the compositions. The present invention also relates to peroxyformic acid formed by the above methods. The present invention further relates to the uses of peroxyformic acid for treating a variety of targets, e.g., target water, including target water used in connection with oil- and gas-field operations. The present invention further relates to methods for reducing or removing H2S or iron sulfide in the treated water source, improving clarity of the treated water source, or reducing the total dissolved oxygen or corrosion in the treated water source, using peroxyformic acid, including peroxyformic acid generated in situ.Type: GrantFiled: January 27, 2020Date of Patent: May 10, 2022Assignee: Ecolab USA Inc.Inventors: Ramakrishnan Balasubramanian, Junzhong Li, Richard Staub, Victor Keasler, Brian Bennett, Allison Brewster
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Patent number: 10710974Abstract: The present invention discloses a method for preparing ?-caprolactone. The method comprises the steps of: adding cyclohexanone, a co-oxidant and a certain amount of catalyst into a certain amount of organic solvent, using molecular oxygen as an oxidant, implementing a reaction with stirring for 0.1 to 24 hours under a pressure of 0.1 to 2 MPa and at a temperature of 60° C. to 100° C., wherein the co-oxidant is acrolein, and the catalyst is a carbon material. The present invention has the advantages of high-efficiency co-oxidant, easily available and recovered catalyst, environmental-friendly oxidant, simple operation and low cost.Type: GrantFiled: December 7, 2016Date of Patent: July 14, 2020Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGYInventors: Hao Yu, Mengmeng Hou, Feng Peng, Yonghai Cao, Hongjuan Wang
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Patent number: 9573893Abstract: The invention relates to a method for producing equilibrium peracetic acid by reacting acetic acid with hydrogen peroxide in an aqueous reaction mixture in the presence of methanesulphonic acid as catalyst, and also to the equilibrium peracetic acid obtainable by the method.Type: GrantFiled: October 9, 2013Date of Patent: February 21, 2017Assignee: EVONIK DEGUSSA GMBHInventors: Andreas Reinold, Stefan Leininger, Angela Hellwig
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Patent number: 8853426Abstract: The present invention relates to a method for manufacturing an ester from a ketone or an aldehyde, which is a reactive substrate, by a Baeyer-Villiger oxidation reaction using hydrogen peroxide, and in this method, as a catalyst, M(BAr4)n, which is a metal borate, is used (M represents an alkali metal or an alkaline earth metal; Ar represents an aryl; and n is the same number as the valence of M). For example, when cyclohexanone was used as the reactive substrate, and Sr[B(3,5-CF3C6H3)4]2 was used as the catalyst, ?-caprolactone was obtained at an isolated yield of 82%.Type: GrantFiled: October 11, 2011Date of Patent: October 7, 2014Assignee: National University Corporation Nagoya UniversityInventors: Kazuaki Ishihara, Muhammet Uyanik
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Publication number: 20140163243Abstract: A tin containing zeolitic material having an MWW-type framework structure (Sn-MWW), having a tin content of at most 2 weight-%, calculated as element and based on the weight of the Sn-MWW, and having an X-ray diffraction pattern comprising peaks at 2 theta diffraction angles of (6.6±0.1)°, (7.1±0.1)°, and (7.9±0.1)°.Type: ApplicationFiled: November 5, 2013Publication date: June 12, 2014Applicant: BASF SEInventors: Andrei-Nicolae Parvulescu, Ulrich Müller, Joaquim Henrique Teles, Nicolas Vautravers, Bernd Hinrichsen, Gerhard Cox, Richard Jacubinas
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Publication number: 20140128622Abstract: A process for the oxidation of an organic carbonyl compound comprising reacting the organic carbonyl compound, optionally in the presence of a solvent, with hydrogen peroxide in the presence of a catalyst comprising a tin-containing zeolitic material having an MWW-type framework structure.Type: ApplicationFiled: November 5, 2013Publication date: May 8, 2014Applicant: BASF SEInventors: Nicolas Vautravers, Joaquim Henrique Teles, Andrei-Nicolae Parvulescu, Ulrich Müller
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Patent number: 8592498Abstract: Disclosed herein are a reaction method and a production method of an organic compound which are capable of achieving high reaction selectivity according to the purpose and a high production rate of a target substance. The methods include at least two fluids, wherein at least one kind of the fluids is a fluid containing at least one organic compound and at least one kind of the fluids other than the above fluid is a fluid containing at least one reactant in the form of a liquid or solution, and the respective fluids join together in a thin film fluid foamed between processing surfaces arranged to be opposite to each other so as to be able to approach to and separate from each other, at least one of which rotates relative to the other, whereby an organic reaction is performed in the thin film fluid.Type: GrantFiled: September 11, 2008Date of Patent: November 26, 2013Assignee: M. Technique Co., Ltd.Inventor: Masakazu Enomura
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Publication number: 20130217898Abstract: The present invention relates to a method for manufacturing an ester from a ketone or an aldehyde, which is a reactive substrate, by a Baeyer-Villiger oxidation reaction using hydrogen peroxide, and in this method, as a catalyst, M(BAr4)n, which is a metal borate, is used (M represents an alkali metal or an alkaline earth metal; Ar represents an aryl; and n is the same number as the valence of M). For example, when cyclohexanone was used as the reactive substrate, and Sr[B(3,5-CF3C6H3)4]2 was used as the catalyst, ?-caprolactone was obtained at an isolated yield of 82%.Type: ApplicationFiled: October 11, 2011Publication date: August 22, 2013Applicant: NATIONAL UNIVERSITY CORPORATION NAGOYA UNIVERSITYInventors: Kazuaki Ishihara, Muhammet Uyanik
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Publication number: 20130005641Abstract: The present invention relates to novel macrocyclic lactones, to processes for their preparation and to their use as fragrances and also to products comprising the novel macrocyclic lactones.Type: ApplicationFiled: June 29, 2012Publication date: January 3, 2013Applicant: BASF SEInventors: Klaus Ebel, Bernhard Brunner, Christoph Stock, Ralf Pelzer
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Publication number: 20110178199Abstract: Disclosed herein are a reaction method and a production method of an organic compound which are capable of achieving high reaction selectivity according to the purpose and a high production rate of a target substance. The methods include at least two fluids, wherein at least one kind of the fluids is a fluid containing at least one organic compound and at least one kind of the fluids other than the above fluid is a fluid containing at least one reactant in the form of a liquid or solution, and the respective fluids join together in a thin film fluid foamed between processing surfaces arranged to be opposite to each other so as to be able to approach to and separate from each other, at least one of which rotates relative to the other, whereby an organic reaction is performed in the thin film fluid.Type: ApplicationFiled: September 11, 2008Publication date: July 21, 2011Applicant: M. Technique Co., Ltd.Inventor: Masakazu Enomura
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Publication number: 20100029956Abstract: Disclosed is a method for producing an ester or lactone in which a secondary alcohol represented by following Formula (1) (wherein Ra and Rb each represent an organic group, or Ra and Rb may be combined to form a ring together with the adjacent carbon atom) is oxidized by molecular oxygen in the presence of a nitrogen-containing cyclic compound containing a structure represented by following Formula (I) [wherein X represents an oxygen atom or an —OR group (wherein R represents a hydrogen atom or hydroxyl-protecting group)] as a constituent of its ring, and at least one of a fluorine-containing alcohol and a fluorinated sulfonic acid, and thereby yields a compound represented by following Formula (2):Type: ApplicationFiled: February 28, 2008Publication date: February 4, 2010Inventors: Yasutaka Ishii, Takahiro Iwahama
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Publication number: 20090306411Abstract: The invention relates to a process for preparing saturated or unsaturated lactones. This process involves reacting a bicyclic compound or a monocyclic compound with hydrogen peroxide in the presence of a first acid having a pKa of 3 or less and a first organic solvent, thereby forming a hydroperoxide. The obtained mixture comprising the hydroperoxide is subsequently metered to a mixture of a second organic solvent and a dissociation-enhancing catalyst, optionally comprising a second organic acid. The invention also pertains to a process of preparing the hydroperoxide.Type: ApplicationFiled: May 10, 2005Publication date: December 10, 2009Applicant: SYMRISE GMBH & CO. KGInventors: John Meijer, Rene Gerritsen, Bart Fischer
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Publication number: 20090240068Abstract: The present disclosure provides processes for the preparation of dodecanedioic acid (DDDA).Type: ApplicationFiled: March 18, 2009Publication date: September 24, 2009Applicant: INVISTA NORTH AMERICA S.A.R.L.Inventor: GURUSAMY RAJENDRAN
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Patent number: 7528268Abstract: The present invention relates to a process for the oxidation, in an inert solvent, of a non-aromatic or non-enonic ethylenic bond or of a non-conjugated cyclic ketones into the corresponding epoxides, respectively lactone, using H2O2 as oxidant, a content in water of the reaction medium below 15% w/w and, as sole catalyst, an alkaline or alkaline earth salt or complex.Type: GrantFiled: August 23, 2005Date of Patent: May 5, 2009Assignee: Firmenich SAInventor: Hubert Mimoun
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Patent number: 6960693Abstract: The present invention relates to an oxidation reaction catalyzed by a reaction controlled phase-transfer catalyst having the general formula of [R1R2R3R4N]xHy[A] or QmMO3(L). The catalysts themselves are not soluble in the reaction medium, but can form an active species that is soluble in the reaction medium under the action of one of the reactants. The active species can in turn react selectively with another reactant. When one of the reactants is completely consumed, the catalyst will separated out from the reacting system and can be recovered by means of simple separation method. The recovered catalyst can be recycled with comparable efficiency as that of the original catalyst. The separation of said catalyst is similar to that of heterogeneous catalyst while said catalyst will completely exhibit the characteristics of homogeneous catalyst during the reaction.Type: GrantFiled: November 29, 2001Date of Patent: November 1, 2005Assignees: China Petroleum & Chemical Corporation, Dalian Institute of Chemical Physics the Chinese Academy of SciencesInventors: Zuwei Xi, Yu Sun, Kunlan Li, Ning Zhou
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Patent number: 6936402Abstract: Disclosed herein is a novel norbornene, acrylate or methacrylate monomer as a photoresist monomer containing an oxepan-2-one group. Further disclosed are photoresist compositions comprising a polymer prepared from the monomer, methods for preparing the photoresist compositions, and methods for forming photoresist patterns using the photoresist compositions.Type: GrantFiled: February 24, 2004Date of Patent: August 30, 2005Assignee: Korea Advanced Institute Science & TechnologyInventors: Jin-Baek Kim, Tae-Hwan Oh, Jae-Hak Choi, Jae-Jun Lee
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Patent number: 6936724Abstract: A process produces ?-caprolactone by the oxidation of cyclohexanone by feeding a crude reaction mixture to a first distillation column; distilling off a first distillate containing low boiling components including unreacted cyclohexanone from the top of the first distillation column; recovering a first side-cut fraction containing unreacted cyclohexanone in a higher concentration than in the first distillate from an intermediate tray; recovering a first bottom liquid containing high boiling components including ?-caprolactone from the bottom; introducing the first side-cut fraction to a second distillation column; recovering a second bottom liquid containing unreacted cyclohexanone from the bottom of the second distillation column; recycling the second bottom liquid into the raw material cyclohexanone; introducing the first bottom liquid to a third distillation column to thereby yield a third distillate containing ?-caprolactone from the third distillation column.Type: GrantFiled: October 21, 2003Date of Patent: August 30, 2005Assignee: Daicel Chemical Industries, LTDInventors: Eiji Ohara, Ken-ichiro Kawazumi
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Patent number: 6838577Abstract: Processes are disclosed for the manufacture of lactones, e.g., caprolactone, from hydoxy acids, e.g., 6-hydroxycaproic acid. The reaction is conducted over a suitable catalyst in the presence of water.Type: GrantFiled: April 17, 2001Date of Patent: January 4, 2005Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Richard A. Galley
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Publication number: 20040087804Abstract: A process produces &egr;-caprolactone by the oxidation of cyclohexanone by feeding a crude reaction mixture to a first distillation column; distilling off a first distillate containing low boiling components including unreacted cyclohexanone from the top of the first distillation column; recovering a first side-cut fraction containing unreacted cyclohexanone in a higher concentration than in the first distillate from an intermediate tray; recovering a first bottom liquid containing high boiling components including &egr;-caprolactone from the bottom; introducing the first side-cut fraction to a second distillation column; recovering a second bottom liquid containing unreacted cyclohexanone from the bottom of the second distillation column; recycling the second bottom liquid into the raw material cyclohexanone; introducing the first bottom liquid to a third distillation column to thereby yield a third distillate containing &egr;-caprolactone from the third distillation column.Type: ApplicationFiled: October 21, 2003Publication date: May 6, 2004Inventors: Eiji Ohara, Ken-ichiro Kawazumi
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Publication number: 20040010152Abstract: An optically active lactone compound is produced by using a Zr(salen) complex of the following formula (I) or its enantiomer as a catalyst and subjecting a cyclic ketone compound to a Baeyer-Villiger reaction with at least one oxidizer selected from hydrogen peroxide, aqueous hydrogen peroxide and urea-hydrogen peroxide adduct in a solvent: 1Type: ApplicationFiled: April 3, 2003Publication date: January 15, 2004Applicant: KYUSHU UNIVERSITYInventors: Tsutomu Katsuki, Akira Watanabe, Tatsuya Uchida
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Patent number: 6667338Abstract: Compounds of formula (I) and formula (II) or therapeutically acceptable salts or prodrugs thereof are useful as antibacterial agents. Methods to make the compounds, compositions containing the compounds, and methods of treatment using the compounds are also disclosed.Type: GrantFiled: January 16, 2002Date of Patent: December 23, 2003Assignee: Abbott LaboratoriesInventors: Zhenkun Ma, Ly Tam Phan, Suoming Zhang, Stevan W. Djuric
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Patent number: 6559322Abstract: The present invention provides a new biocatalyst whole cell system for converting cyclic ketones such as cyclopentanone/cyclohexanone to the corresponding lactones such as valerolactone/caprolactone. Another novel aspect of the present invention is that biocatalyst fungus Fusarium oxysporum f.sp. ciceri NCIM 1282 species has been found to be an efficient biocatalyst system for any biotransformation for the first time.Type: GrantFiled: December 21, 2001Date of Patent: May 6, 2003Assignee: Council of Scientific and Industrial ResearchInventors: Deendayal Mandal, Absar Ahmad, Mohammed Islam Khan, Rajiv Kumar
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Patent number: 6531616Abstract: This invention pertains to a process for making &agr;-methylenelactones and &agr;-substitute hydrocarbylidene lactones. More specifically, the present invention obtains high yields of &agr;-methylene-&ggr;-butyrolactone by heating &ggr;-butyrolactone and diethyl oxalate in the presence of a base. The second step comprises treatment of the &agr;-oxalyl enolate salt with formaldehyde to afford the &agr;-methylene-&ggr;-butyrolactone.Type: GrantFiled: December 21, 2001Date of Patent: March 11, 2003Assignee: E. I. du Pont de Nemours and CompanyInventors: Rutger D. Puts, Charles Brandenburg, Kenneth R. Tarburton
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Patent number: 6472540Abstract: What is disclosed is a process for producing &egr;-caprolactone which comprises removing impurities by distillation from a reaction mixture obtained by co-oxidation of cyclohexanone and aldehyde, wherein &egr;-caprolactone separated from a purifying column is contacted with oxygen containing gas in the presence of cobalt. High boiling point components are removed to give an acid value of lower than 0.15 mgKOH/g. Thereby, a high quality &egr;-caprolactone providing improved polymer appearance is produced advantageously on an industrial scale without repeated purifying distillations or without using expensive stabilizer or adsorbent for the improvement of color.Type: GrantFiled: July 14, 2000Date of Patent: October 29, 2002Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kazuo Tanaka, Atsushi Okoshi, Hiroshi Ogawa
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Patent number: 6350883Abstract: The present invention is related to a method for preparing lactam represented by the following formula: wherein R is C2-10 alkylene which may be optionally substituted with C1-6 alkyl or phenyl; R′ is a hydrogen atom, C1-6 alkyl, C1-6 hydroxyalkyl or phenyl. The method for preparing lactam comprises an amination reaction using crystalline aluminosilicate zeolites as catalysts under the condition of gas phase in the presence of (a) lactone, (b) amine and/or ammonia and (c) water.Type: GrantFiled: November 22, 2000Date of Patent: February 26, 2002Assignee: Dairen Chemical CorporationInventors: Shien-Chang Chen, Fu-Shen Lin, Liang-An Hsu, Cheng-Lin Tsai, Joe-Min Lin
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Publication number: 20010053858Abstract: This invention relates in part to processes for producing one or more substituted or unsubstituted epsilon caprolactones and/or hydrates and/or esters thereof which comprise subjecting one or more substituted or unsubstituted penten-1-ols to carbonylation in the presence of a carbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce said one or more substituted or unsubstituted epsilon caprolactones and/or hydrates and/or esters thereof. The substituted and unsubstituted epsilon caprolactones and/or hydrates and/or esters thereof produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof, e.g., epsilon caprolactam. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted epsilon caprolactones and/or hydrates and/or esters thereof as principal product(s) of reaction.Type: ApplicationFiled: December 4, 2000Publication date: December 20, 2001Inventors: Erik Bruce Tjaden, John Robert Briggs, Anil Sakharam Guram, John Michael Maher
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Patent number: 6194575Abstract: The present invention relates to a process for the preparation of compounds of the formula (I) by reacting compounds of the formula (II) in which Het, R1, R2 and R4 are as defined in the description, with urea.Type: GrantFiled: September 21, 1999Date of Patent: February 27, 2001Assignee: Bayer AktiengesellschaftInventors: Detlef Wollweber, Wolfgang Krämer, Eric Rivadeneira
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Patent number: 6184391Abstract: This invention relates in part to processes for producing one or more substituted or unsubstituted epsilon caprolactones and/or hydrates and/or esters thereof which comprise subjecting one or more substituted or unsubstituted penten-1-ols to carbonylation in the presence of a carbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce said one or more substituted or unsubstituted epsilon caprolactones and/or hydrates and/or esters thereof. The substituted and unsubstituted epsilon caprolactones and/or hydrates and/or esters thereof produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof, e.g., epsilon caprolactam. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted epsilon caprolactones and/or hydrates and/or esters thereof as principal product(s) of reaction.Type: GrantFiled: April 15, 1997Date of Patent: February 6, 2001Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Erik Bruce Tjaden, John Robert Briggs, Anil Sakharam Guram, John Michael Maher
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Patent number: 5994565Abstract: A process for producing purified .epsilon.-caprolactone from an .epsilon.-caprolactone-containing reaction product produced by the oxidation of cyclohexanone comprising subjecting the .epsilon.-caprolactone-containing reaction product to an alkali-treatment in the presence of an inert gas atmosphere or to a heat treatment in the presence of an inert gas atmosphere or to a combined alkali-treatment and heat treatment, and distilling the treated reaction product.Type: GrantFiled: March 18, 1999Date of Patent: November 30, 1999Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kazuo Tanaka, Atsushi Okoshi, Hiroshi Ogawa
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Patent number: 5981769Abstract: 1,6-hexanediol and .epsilon.-caprolactone are prepared from a carboxylic acid mixture comprising adipic acid, 6-hydroxycaproic acid and small amounts of 1,4-cyclohexanediols which is obtained as a by-product in the oxidation of cyclohexane to cyclohexanone/cyclohexanol using oxygen or oxygen-containing gases by water extraction of the reaction mixture, by esterifying and hydrogenating a substream to give hexanediol and cyclizing 6-hydroxycaproic esters to give caprolactone.Type: GrantFiled: August 28, 1998Date of Patent: November 9, 1999Assignee: BASF AktiengesellschaftInventors: Karl Gerhard Baur, Rolf Fischer, Rolf Pinkos, Frank Stein, Boris Breitscheidel, Harald Rust
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Patent number: 5917067Abstract: A process for producing an omega-functionalized aliphatic carboxylic acid starting from cyclohexanone and omega-functionalized .alpha.-olefins or acrylic esters. The process comprises an addition step, an oxidation step, an isomerization step, and one or more hydrogenation steps. The process allows to use raw materials that are available at low cost and to achieve high selectivity and high yield with industrially simple steps. The process includes the production of new intermediate products, including 2-oxepanone-7-substituted products.Type: GrantFiled: April 18, 1996Date of Patent: June 29, 1999Assignee: Industrie Chimiche Caffaro S.P.A.Inventors: Livius Cotarca, Paolo Maggioni, Alfonso Nardelli, Stefano Sguassero
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Patent number: 5670661Abstract: The present invention relates to a process for producing lactones starting from cyclic ketones which comprises an oxidation reaction which is performed in the presence of an optionally substituted cycloaliphatic peracid or of an optionally substituted aliphatic peracid that is immiscible with water. The process allows to obtain high selectivity, does not entail the use of dangerous reagents, and allows excellent economic advantages.Type: GrantFiled: April 16, 1996Date of Patent: September 23, 1997Assignee: Industrie Chimiche Caffaro S.p.A.Inventors: Livius Cotarca, Roberto Bianchini
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Patent number: 5665891Abstract: A process for the catalysed oxidation of ketones to esters or lactones with hydrogen peroxide in the presence of a carboxylic acid or anhydride is provided. The process employs gamma alumina as a heterogeneous catalyst. In certain preferred embodiments the catalyst also contains a tungsten-containing heteropolyacid. Preferably, the heteropolyacid contains phosphorus. In a related process, the catalyst accelerates the formation of percarboxylic acid solutions.Type: GrantFiled: October 12, 1995Date of Patent: September 9, 1997Assignee: Solvay Interox LimitedInventors: Scott William Brown, Alexander Johnstone, William Ronald Sanderson
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Patent number: 5340552Abstract: A macroreticulate polymer is provided for removing water vapor and oxidants from a gas having the formula: ##STR1## wherein Ar is a heteroaromatic moiety, M is bonded to the heteroaromatic moiety and is selected from the group consisting of lithium, sodium, potassium, alkyl magnesium, alkyl zinc, and dialkylaluminum, R is an organic moiety and R.sub.1 is a polymerized moiety forming the molecular backbone of said polymer.Type: GrantFiled: September 10, 1992Date of Patent: August 23, 1994Assignee: Millipore CorporationInventor: James T. Snow
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Patent number: 5278321Abstract: A process for simultaneously producing a lactone and an aromatic carboxylic acid, which comprises oxidizing a cyclic ketone and an aromatic aldehyde wherein: the cyclic ketone/aromatic aldehyde molar ratio is set at 1.1:1 to 20:1 and the throughput of the aromatic aldehyde per a unit reaction solution volume and a unit time is set at 0.05 to 1.5 mol/1.hour.Type: GrantFiled: August 11, 1992Date of Patent: January 11, 1994Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Toru Tanaka, Kazuo Tanaka
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Patent number: 5260426Abstract: The invention relates to antibacterial pseudo-primycin complexes of formula (I) ##STR1## to the components and acid addition salts thereof, as well as to the preparation of these compounds and to the pharmaceutical compositions containing said compounds as active ingredient.In the formula (I) R.sup.1 is butyl, pentyl or hexyl, R.sup.2 is hydrogen, hydroxyl or O-arabinose and X is organic or inorganic acid ion.Type: GrantFiled: March 24, 1992Date of Patent: November 9, 1993Assignee: Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T.Inventors: Gyula Dekany, Judit Frank, Istvan Pelczer, Gabor Kulcsar, Eniko Schreiner
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Patent number: 5079372Abstract: A method for producing a lactone by hydrogenating a dicarboxylic acid, a dicarboxylic acid anhydride and/or a dicarboxylic acid ester in the presence of a catalyst, wherein the hydrogenation reaction is conducted in the liquid phase in the presence of (1) ruthenium, (2) an organic phosphine and (3) a compound of a metal selected from the group consisting of Groups IVA, VA and IIIB in the Periodic Table.According to the present invention, for the production of a lactone by hydrogenating a dicarboxylic acid, a dicarboxylic acid anhydride and/or a dicarboxylic ester, the reaction is conducted in a homogeneous liquid phase reaction by using the ruthenium,organic phosphine and compound of a metal selected from the group consisting of Groups IVA, VA and IIIB, of the present invention as the catalyst, whereby the desired lactone product can be obtained at high selectivity under a mild condition as compared with the conventional methods.Type: GrantFiled: May 1, 1990Date of Patent: January 7, 1992Assignee: Mitsubishi Kasei CorporationInventors: Keisuke Wada, Yoshinori Hara, Koushi Sasaki
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Patent number: 4994583Abstract: Process for manufacturing .SIGMA.- caprolactone by oxidation of cyclohexanone by means of a crude C.sub.2 -C.sub.4 percarboxylic acid solution, resulting from the reaction of hydrogen peroxide on the corresponding carboxylic acid in the presence of a weak acid catalyst, with continuous elimination of water by azeotropic entrainment, characterized in that the molar ratio of cyclohexanone used to the percarboxylic acid is between about 0.50 to 0.99.Type: GrantFiled: July 12, 1989Date of Patent: February 19, 1991Assignee: Produits Chimiques Uging KuhlmannInventors: Michele Pralus, Jean-Claude Lecoq, Jean-Pierre Schirmann
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Patent number: 4988825Abstract: Aldehydes and ketones, other than acetone, are oxidized with an alkali metal perborate in the presence of an acid.Type: GrantFiled: September 23, 1986Date of Patent: January 29, 1991Assignee: Cooper Union Research Foundation, Inc.Inventor: John L. Bove
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Patent number: 4870192Abstract: This invention provides process embodiments for shape-selective oxidation of cyclic ketones to lactone and/or omega-hydroxycarboxylic acid products in the presence of a zeolite catalyst composition such as ZSM-5 or zeolite Beta.Cyclohexanone can be converted to epsilon-caprolactone or 6-hydroxycaproic acid as a main product under selected conditions.Type: GrantFiled: October 14, 1986Date of Patent: September 26, 1989Assignee: Mobil Oil CorporationInventors: Clarence D. Chang, Stuart D. Hellring
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Patent number: 4740603Abstract: This invention relates to a process for the preparation of stable solutions of .epsilon.-caprolactone by means of the oxidation of cyclohexanone by a percarboxylic acid containing 2 to 4 carbon atoms. According to the invention, the percarboxylic acid is in the form of a crude solution, such as that resulting from the reaction of hydrogen peroxide with the corresponding carboxylic acid in the presence of a boric acid catalyst with the continuous elimination of water by azeotropic entrainment.Type: GrantFiled: June 4, 1986Date of Patent: April 26, 1988Assignee: PCUK Produits Chimiques Ugine KuhlmannInventors: Jean-Claude Lecoq, Michele Pralus, Jean-Pierre Schirmann
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Patent number: 4353832Abstract: A process for the production of carboxyl compounds such as caprolactones, in which the corresponding carbonyl compounds are oxidized with hydrogen peroxide in the presence of a catalyst in a substantially anhydrous liquid medium. The water formed by the reaction and any water introduced into the reaction mixture are removed from the reaction mixture.Type: GrantFiled: June 5, 1980Date of Patent: October 12, 1982Assignee: INTEROX (Societe Anonyme)Inventors: Andre Lecloux, Claude Declerck, Franz Legrand
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Patent number: 4341709Abstract: A process for the preparation of .epsilon.-caprolactone comprising:(a) reacting cyclohexanone with a solution of perpropionic acid in an organic solvent at a molar ratio of cyclohexanone;perpropionic acid of about 1.1-5:1 at a temperature of about 10.degree. to 80.degree. C. to form a reaction mixture consisting essentially of .epsilon.-caprolactone, propionic acid and organic solvent,(b) distilling the reaction mixture from (a) in a first distillation unit to obtain a distillate comprising the organic solvent and a distillation residue,(c) introducing the distillation residue from (b) at a point into a second distillation unit to obtain a distillate comprising propionic acid and unreacted cyclohexanone, removing from the second distillation unit, separately from one another and at a point below the point of introduction into the second distillation unit, .epsilon.Type: GrantFiled: May 15, 1980Date of Patent: July 27, 1982Assignee: Bayer AktiengesellschaftInventors: Willi Hofen, Herbert Klenk, Gerd Schreyer, Otto Weiberg, Helmut Waldmann, Hermann Seifert, Karl-Hermann Reissinger, Wolfgang Swodenk