Halogen Containing Patents (Class 568/841)
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Patent number: 7268252Abstract: Disclosed herein are novel binaphthol derivatives and methods for the optical resolution of amino acids or amino alcohols and for the optical transformation of D, L-forms of amino acids using the same.Type: GrantFiled: January 30, 2006Date of Patent: September 11, 2007Assignee: Green of Life Co., Ltd.Inventors: Kwan Mook Kim, Won Woo Nam, Hyun Jung Park, Jik Chin
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Patent number: 7205443Abstract: A process for producing a fluorine-containing 2,4-diol represented by the formula [4], wherein R1 represents a hydrogen atom or an acyclic or cyclic alkyl group having a carbon atom number of 1 to 7; R2 represents an acyclic or cyclic alkyl group having a carbon atom number of 1 to 7; and R1 and R2 are optionally bonded to each other to form a ring, includes reducing a hydroxy ketone represented by the formula [3], wherein R1 and R2 are defined as above, by hydrogen in the presence of a ruthenium catalyst.Type: GrantFiled: January 26, 2005Date of Patent: April 17, 2007Assignee: Central Glass Company, LimitedInventors: Takeo Komata, Kei Matsunaga, Yoshiki Hirotsu, Shinya Akiba
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Patent number: 7193114Abstract: The present invention attaches a molecule that contains a hydroxyl group (OH) attached to a carbon chain which is attached to a coordinating atom or atoms, the acidity of which is greater than that of silica (i.e., pKA <10). The condensation is achieved by mixing silica gel, appropriate amount of ligand, and a drop of conc. sulfuric acid in toluene in a flask attached to a Dean-Stark tube. Heating of the mixture is continued until the amount of water, obtained by azeotropic distillation and condensation, reaches a constant value. Toluene is filtered off, and recycled. The supported ligand is dried under reduced pressure to remove residual toluene. The composite (ligand attached to silica) can then be used by batch or column method to remove heavy metal ions from aqueous solution.Type: GrantFiled: January 14, 2004Date of Patent: March 20, 2007Assignee: University of South FloridaInventors: Dean F. Martin, Craig A. Bowe
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Patent number: 7157609Abstract: A process of producing propylene chlorohydrin using a reactor having a one-way flow reaction area and a circulating flow reaction area which are connected in series. In this process, a propylene-containing gas is supplied to an aqueous solution of chlorine in the one-way flow reaction area to carry out at least part of a propylene chlorohydrin forming reaction so as to form a reaction mixture fluid containing propylene chlorohydrin and propylene and/or chlorine. The above reaction mixture fluid discharged from this reaction area is supplied to the circulating flow reaction area as at least part of a make-up medium, a propylene-containing gas and/or chlorine are/is supplied as required to continue the reaction in the circulating flow reaction area so as to obtain a reaction solution having a desired content of propylene chlorohydrin, and part of the reaction solution is extracted.Type: GrantFiled: May 21, 2003Date of Patent: January 2, 2007Assignee: Tokuyama CorporationInventors: Hiroki Tanaka, Yoji Mizushima, Yoshikazu Kodama, Tomoaki Fujii, Manabu Kamamoto, Koujiro Miyazaki
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Patent number: 6992213Abstract: Trifluoroethanol can be isolated from organic liquids that are contaminated by trifluoroethanol by bringing the contaminated liquid into contact with a molecular sieve having a pore size ranging between 0.5 and 1.0 nm, e.g., with molecular sieve 13X. This enables, for example, trifluoroacetic acid trifluoroethyl esters, bis(trifluoroethyl)carbonate or trifluoroethyl esters of phosphoric, phosphonic or phosphinic acid to be purified.Type: GrantFiled: March 3, 2004Date of Patent: January 31, 2006Assignee: Solvay Fluor und Derivate GmbHInventors: Olaf Boese, Katja Peterkord
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Patent number: 6992229Abstract: The present invention has an object to provide a method for purifying a fluorinated hydroxyl compound of the formula 1 safely in a high yield under industrially practical conditions. Namely, a mixture containing a fluorinated hydroxyl compound of Rf—CR1R2—OH (Formula 1, wherein Rf is a C1-20 polyfluoroalkyl group, and each of R1 and R2 is a hydrogen atom or a C1-3 alkyl group) such as 2,2,3,3-tetrafluoropropanol, and a compound having an unshared electron pair, is distilled by heating in the presence of a solid acid catalyst such as a cation exchange resin catalyst, or by adding a proton source such as water.Type: GrantFiled: November 19, 2002Date of Patent: January 31, 2006Assignee: Asahi Glass Company, LimitedInventors: Hidekazu Okamoto, Akihiro Wada, Toshihiko Toma, Nobuyuki Yamagishi
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Patent number: 6956140Abstract: A process for preparing a halogenated alcohol comprising hydrolyzing a halogenated precursor of the halogenated alcohol in water at a temperature near but below the critical point of water. For example, the halogenated alcohol has the formula CF3(CF2)nCH2OH, wherein n is zero or a whole number from 1 to 5, the halogenated precursor has the formula CF3(CF2)nCH2Cl, wherein n is as defined above, and the process comprises hydrolyzing the halogenated precursor in water at a temperature near but below the critical point of water. In a particularly preferred embodiment, the halogenated alcohol has the formula CF3CH2OH, the halogenated precursor has the formula CF3CH2Cl, and the process comprises hydrolyzing CF3CH2Cl in water at a temperature near but below the critical point of water.Type: GrantFiled: December 13, 2000Date of Patent: October 18, 2005Assignee: Halocarbon Products CorporationInventor: Robert L. Ehrenfeld
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Patent number: 6930212Abstract: The present invention has an object to provide a method for purifying a fluorinated hydroxyl compound of the formula 1 safely in a high yield under industrially practical conditions. Namely, a mixture containing a fluorinated hydroxyl compound of Rf—CR1R2—OH (Formula 1, wherein Rf is a C1-20 polyfluoroalkyl group, and each of R1 and R2 is a hydrogen atom or a C1-3 alkyl group) such as 2,2,3,3-tetrafluoropropanol, and a compound having an unshared electron pair, is distilled by heating in the presence of a solid acid catalyst such as a cation exchange resin catalyst, or by adding a proton source such as water.Type: GrantFiled: February 20, 2002Date of Patent: August 16, 2005Assignee: Asahi Glass Company, LimitedInventors: Hidekazu Okamoto, Akihiro Wada, Toshihiko Toma, Nobuyuki Yamagishi
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Patent number: 6894196Abstract: A process for producing a high-purity fluorinated alcohol in a good purification yield, is provided. In a process for producing a fluorinated alcohol, which comprises reacting methanol with tetrafluoroethylene or hexafluoropropylene in the presence of an alkyl peroxide, the reaction liquid after completion of the reaction is distilled in the presence of water and HF to separate it into a fraction containing an alcohol derived from the alkyl peroxide and a bottom liquid containing the fluorinated alcohol, and then, the bottom liquid is purified to recover the fluorinated alcohol.Type: GrantFiled: February 24, 2003Date of Patent: May 17, 2005Assignee: Asahi Glass Company, LimitedInventor: Hidekazu Okamoto
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Patent number: 6867336Abstract: In a process for the continuous preparation of 2-bromo-2-nitro-1,3-propanediol, nitromethane is firstly reacted with formaldehyde and alkali metal hydroxide and the reaction mixture obtained in this way is subsequently reacted with bromine.Type: GrantFiled: August 1, 2002Date of Patent: March 15, 2005Assignee: BASF AktiengesellschaftInventors: Günter Scherr, Thomas Bogenstätter, Jürgen Huff
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Publication number: 20040152926Abstract: A method for producing fluorinated alcohols from fluorinated alkyl halides can produce fluorinated alcohols at high product yield and at high selectivity in a single-step reaction. The method eliminates the need to use heavy metals and other toxic compounds that are difficult to handle or process.Type: ApplicationFiled: March 1, 2004Publication date: August 5, 2004Inventors: Hideyuki Mimura, Kosuke Kawada, Shoji Arai
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Patent number: 6770789Abstract: The subject invention relates to a process for the trifluoromethylation of sulfates, including cyclic and acyclic sulfates. The subject invention further pertains to the compounds produced by the trifluoromethylation of sulfates.Type: GrantFiled: March 13, 2003Date of Patent: August 3, 2004Assignee: University of Florida Research FoundationInventors: William R. Dolbier, Jr., Naoto Takechi
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Publication number: 20040030198Abstract: A process of producing propylene chlorohydrin using a reactor having a one-way flow reaction area and a circulating flow reaction area which are connected in series. In this process, a propylene-containing gas is supplied to an aqueous solution of chlorine in the one-way flow reaction area to carry out at least part of a propylene chlorohydrin forming reaction so as to form a reaction mixture fluid containing propylene chlorohydrin and propylene and/or chlorine. The above reaction mixture fluid discharged from this reaction area is supplied to the circulating flow reaction area as at least part of a make-up medium, a propylene-containing gas and/or chlorine are/is supplied as required to continue the reaction in the circulating flow reaction area so as to obtain a reaction solution having a desired content of propylene chlorohydrin, and part of the reaction solution is extracted.Type: ApplicationFiled: May 21, 2003Publication date: February 12, 2004Inventors: Hiroki Tanaka, Yoji Mizushima, Yoshikazu Kodama, Tomoaki Fujii, Manabu Kamamoto, Koujiro Miyazaki
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Publication number: 20030187291Abstract: Iodohydroxylated olefins can be prepared by treating an olefin with an aqueous solution of an iodine monohalide selected from iodine monochloride and iodine monobromide.Type: ApplicationFiled: January 31, 2003Publication date: October 2, 2003Inventors: Yongkui Sun, Thorsten Rosner
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Publication number: 20030149311Abstract: Methods for continuously producing 2,3-dichloro-1-propanol (2,3-DCH) and epichlorohydrin in high yields and in a stabel manner for a long time are disclosed. In a method where allyl alcohol is chorinated in a hyrochloric acid solution and the reaction solution is introduced into a degassing tower to release hydrogen chloride and 2,3-DCH is obtained from the remaining solution, the concentraton of chlorine in the reaction mixture to be introduced into the degassing tower is maintaining to 0.015 g/ml or less and/or the partial pressure of chlorine gas in the reactor immediately before the degassing tower to 0.08 MPa or less, by monitoring and/or the partial pressure of chlorine gas in the reactor immediately before the degassing tower to 0.Type: ApplicationFiled: December 16, 2002Publication date: August 7, 2003Inventors: Toshitaka Hiro, Kazuhiro Sakurai
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Patent number: 6579725Abstract: The present invention relates to versatile linkers for tethering a molecule to a solid support, e.g., for tethering a monomer, oligomer or polymer to a solid support, which are stable to a wide range of reaction conditions, but can be cleaved under well-defined conditions, thereby liberating the molecule from the solid support. Preferably, the linkers are used to tether to the solid support unprotected, partially-protected or fully-protected monosaccharides or oligosaccharides, or unprotected, partially-protected or fully-protected glycoconjugates. The linkers of the present invention may be used to tether to solid supports building blocks useful in the assembly of libraries of other types of small molecules. The present invention also relates to a molecule or plurality of molecules tethered to the solid support via a linker or linkers of the present invention. The present invention also relates to processes for synthesizing molecules, e.g.Type: GrantFiled: March 3, 2000Date of Patent: June 17, 2003Assignee: Massachusetts Institute of TechnologyInventors: Peter H. Seeberger, Rodrigo B. Andrade
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Publication number: 20020095059Abstract: Disclosed are methods of producing fluorinated alcohols which find particular use in the syntheses of pharmaceutical drugs. The methods comprise generally, the steps of (a) reacting a halogenated alkane with an alkyl vinyl ether to form an unsaturated halogenated aldehyde; (b) reducing the unsaturated halogenated aldehyde to form an unsaturated halogenated alcohol; and (c) reducing the unsaturated halogenated alcohol to form a fluorinated alcohol.Type: ApplicationFiled: January 12, 2001Publication date: July 18, 2002Inventors: Haridasan K. Nair, Andrew Joseph Poss
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Patent number: 6388124Abstract: There is disclosed a dihalo-compound of formula (1): wherein X1 and X2 represent different halogen atoms, R represents a hydrogen atom or a protective group for a hydroxyl group, and a process for producing vitamin A derivative via a sulfone derivative of formula (5): wherein Ar represents an optionally substituted aryl group, and R represents the same as defined above.Type: GrantFiled: January 26, 2001Date of Patent: May 14, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Toshiya Takahashi, Shinzo Seko
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Patent number: 6350922Abstract: A process for making 2,3-dihalopropanol including reacting 2,3-dihalopropanal with a hydrogenating agent in the presence of an iridium and a second transition metal mixed metal catalyst where the second transition metal is selected from the group comprising ruthenium, iron, molybdenum, tungsten, rhenium, osmium, manganese or vanadium, under conditions such that 2,3-dihalopropanol is formed. The 2,3-dihalopropanol is particularly useful in a process for making epihalohydrin.Type: GrantFiled: December 16, 1999Date of Patent: February 26, 2002Assignee: The Dow Chemical CompanyInventors: Paul C. Vosejpka, Dennis A. Hucul, Bob R. Maughon, Larry N. Ito, Robert M. Campbell
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Publication number: 20010025127Abstract: There is disclosed a dihalo-compound of formula (1): 1Type: ApplicationFiled: January 26, 2001Publication date: September 27, 2001Inventors: Toshiya Takahashi, Shinzo Seko
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Patent number: 6288285Abstract: A process for producing dichloroacetoxypropane comprising reacting allyl acetate with chlorine in a gaseous phase in the presence of a catalyst comprising an element of Group 16 of the long-form Periodic Table or in the absence of a catalyst. The dichloroacetoxypropane obtained may be converted to dichloropropanol and epichlorohydrin.Type: GrantFiled: March 29, 2000Date of Patent: September 11, 2001Assignee: Showa Denko K.K.Inventors: Takanori Aoki, Takami Ohe, Haruki Ishikami
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Patent number: 6118030Abstract: A process for producing dichloroacetoxypropane comprising reacting allyl acetate with chlorine in a gaseous phase in the presence of a catalyst. The dichloroacetoxypropane obtained may be converted to dichloropropanol and epichlorohydrin.Type: GrantFiled: February 16, 1999Date of Patent: September 12, 2000Assignee: Showa Denko K.K.Inventors: Takanori Aoki, Takami Ohe, Haruki Ishikami, Taketoshi Naitoh, Tatsuharu Arai
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Patent number: 6025531Abstract: A process for preparing an optically active alcohol by reacting a prochiral ketone corresponding to the optically active alcohol and an acid with a mixture of (1) a boron-containing compound selected from the group consisting of i) a borane compound which is obtained from an optically active .beta.-aminoalcohol and a boron hydride; or obtained from the optically active .beta.-aminoalcohol, a metal borohydride and an acid and ii) an optically active oxazaborolidine and (2) a metal borohydride; and a process for preparing an optically active amine by reacting an oxime derivative and an acid with a mixture of (1) a boron-containing compound selected from the group consisting of i) a borane compound which is obtained from an optically active .beta.-aminoalcohol and a boron hydride, or obtained from said optically active .beta.-aminoalcohol, a metal borohydride and an acid and ii) an optically active oxazaborolidine, and (2) a metal borohydride.Type: GrantFiled: June 3, 1998Date of Patent: February 15, 2000Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Naoto Konya, Gohfu Suzukamo
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Patent number: 6008419Abstract: A 2,3-dihalopropanol is made by reacting 2,3-dihalopropanal with molecular hydrogen in the presence of a transition metal-containing catalyst, under conditions such that 2,3-dihalopropanol is formed. The reaction is particularly useful, for example, as Step (3) in a process to make epihalohydrin which may be generally prepared by:(1) reacting a 3-carbon hydrocarbon with an oxidizing agent to form acrolein;(2) reacting acrolein with a molecular halogen to form 2,3-dihalopropanal;(3) reducing 2,3-dihalopropanal with molecular hydrogen to form 2,3-dihalopropanol; and(4) cyclizing 2,3-dihalopropanol to make epihalohydrin.The process produces epihalohydrin using only about one mole of halogen per mole of epihalohydrin. It also uses substantially less water than existing processes.Type: GrantFiled: December 19, 1997Date of Patent: December 28, 1999Assignee: The Dow Chemical CompanyInventors: P. J. Thomas, R. Garth Pews, Paul C. Vosejpka, George J. Frycek
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Patent number: 5962516Abstract: Compounds and methods for use in immunosuppressive and anti-inflammatory treatment, and for inhibiting male fertility, are described. The compounds are triptolide analogs with improved water solubility and low toxicity.Type: GrantFiled: January 25, 1999Date of Patent: October 5, 1999Assignee: Pharmagenesis, Inc.Inventors: You Mao Qi, John H. Musser, John M. Fidler
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Patent number: 5929284Abstract: Processes for efficiently producing .alpha.-halo ketones, .alpha.-halohydrins and epoxides on an industrial scale. The prosesses include one for producing an .alpha.-halo ketone of general formula (3) by decarboxylating a product of reaction between a carboxilic acid derivative of general formula (1) and a metal enolate prepared from an .alpha.-haloacetic acid of general formula (2) or an acceptable salt thereof, one for producing an by reducing the .alpha.-halo ketone (3), and one for producing an epoxide (13) by treating the .alpha.-halohydrin (11) with a base to effect ring closure. The above prosesses are particularly suitable for producing optically active .alpha.-halo ketones, .alpha.-halohydrins and epoxides from the corresponding .alpha.-amino acid derivatives.Type: GrantFiled: December 18, 1996Date of Patent: July 27, 1999Assignee: Kaneka CorporationInventors: Akira Nishiyama, Tadashi Sugawa, Hajime Manabe, Kenji Inoue, Noritaka Yoshida
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Patent number: 5874650Abstract: A process for the preparation of 4,4,4-trichlorobutan-1-ol which comprises reacting allyl alcohol with chloroform in the presence of a radical initiator. Preferably the allyl alcohol is added incrementally to the chloroform over the period of the reaction.Type: GrantFiled: July 8, 1997Date of Patent: February 23, 1999Assignee: Zeneca LimitedInventor: Martin Charles Bowden
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Patent number: 5792876Abstract: A process is described for producing acetals comprising reacting an aldehyde or a ketone with an alcohol in the presence of a titanium compound having an acetylacetone as a ligand, or in the presence of a compound selected from the group consisting of stannous chloride dihydrate, cerium chloride hexahydrate and bismuth chloride. The process can be used in the synthesis of unstable acetals or when water exists in the reaction mixture, and therefore the process can be used for a wide variety of applications.Type: GrantFiled: November 6, 1996Date of Patent: August 11, 1998Assignee: Kuraray Co., Ltd.Inventors: Hideharu Iwasaki, Masahiko Kitayama, Takashi Onishi
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Patent number: 5744655Abstract: A 2,3-dihalopropanol is made by reacting 2,3-dihalopropanal with a hydrogenating agent in the presence of a transition metal-containing catalyst, under conditions such that 2,3-dihalopropanol is formed. The reaction is particularly useful as Step (3) in a process to make epihalohydrin by:(1) reacting a 3-carbon hydrocarbon with an oxidizing agent to form acrolein;(2) reacting acrolein with a molecular halogen to form 2,3-dihalopropanal;(3) reducing 2,3-dihalopropanal to form 2,3-dihalopropanol; and(4) cyclizing 2,3-dihalopropanol to make epihalohydrin.The process produces epihalohydrin using only about one mole of halogen per mole of epihalohydrin. It also uses substantially less water than existing processes.Type: GrantFiled: June 19, 1996Date of Patent: April 28, 1998Assignee: The Dow Chemical CompanyInventors: P. J. Thomas, R. Garth Pews, Paul C. Vosejpka, George J. Frycek
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Patent number: 5731479Abstract: Optically active alcohols are prepared by reducing optically active carboxylic acids with hydrogen in the presence of ruthenium catalysts.Type: GrantFiled: December 5, 1995Date of Patent: March 24, 1998Assignee: Bayer AktiengesellschaftInventor: Stefan Antons
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Patent number: 5696299Abstract: A process for producing an optically active alcohol comprising carrying out interesterification between a racemic alcohol and an ester selected from the group consisting of (a) a diester between a lower monohydric alcohol and a saturated dicarboxylic acid having 14 or more carbon atoms, (b) a triglyceride of a saturated fatty acid having 16 or more carbon atoms, and (c) a monoester between a lower monohydric alcohol and a saturated fatty acid having 18 or more carbon atoms in the presence of lipase, preferably heat-resistant lipase, and in the presence or absence of a solvent, preferably in the absence of a solvent, under a substantially water-free condition, separating an optically active alcohol rich in either one of R- and S-forms from the reaction mixture, and adding an optically inactive non-racemic alcohol to the residue of the previous step to carry out interesterification under the same conditions as in the previous reaction to separate the other enantiomer.Type: GrantFiled: September 15, 1995Date of Patent: December 9, 1997Assignee: The Nisshin Oil Mills, Ltd.Inventors: Satoshi Negishi, Seiichi Shirasawa, Junko Suzuki, Yukie Masuda
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Patent number: 5637780Abstract: This invention relates to methods for preparing alkylating agents and use of the agents prepared. In particular, this invention relates to preparation methods for hydroxy halide and organooxy halide alkylating agents and their use for alkylating cyclic urea compounds.Type: GrantFiled: June 30, 1994Date of Patent: June 10, 1997Assignee: The DuPont Merck Pharmaceutical CompanyInventors: Prabhakar K. Jadhav, George C. Emmett, Michael E. Pierce
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Patent number: 5576467Abstract: The present invention relates to a method of preparing an alcohol by reducing a carboxylic acid or a derivative thereof, more particularly, a method of preparing an alcohol by a reduction reaction in the presence of a zirconium-titanium oxide catalyst. A carboxylic acid or a carboxylic acid derivative is converted into a corresponding alcohol by a reduction reaction in the presence of a zirconium-titanium oxide catalyst using an alcohol as a hydrogen source. An alcohol can be prepared in a high yield in the present invention. To be more specific, the method of the present invention can convert a higher fatty acid or a carboxylic acid derivative, which has given a corresponding alcohol in a low yield in the presence of a zirconium catalyst alone, into the corresponding alcohol in a high yield. Further, the reaction can be performed easily, and the product can be easily separated from the catalyst.Type: GrantFiled: June 7, 1995Date of Patent: November 19, 1996Assignee: Japan Tobacco Inc.Inventors: Kyoko Takahashi, Makoto Shibagaki, Hajime Matsushita
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Patent number: 5556820Abstract: A solid product as a catalyst component for an olefin polymerization catalyst is obtained by the reaction of metallic magnesium, an alcohol, and a halogen in an amount ranging from 0.019 to 0.06 gram-atom per one mole of metallic magnesium. Alternatively, the halogen component is a halogen-containing compound which contains not less than 0.0001 gram-atom of a halogen atom per one gram-atom of metallic magnesium.Type: GrantFiled: March 2, 1994Date of Patent: September 17, 1996Assignee: Idemitsu Petrochemical Co., Ltd.Inventors: Hideo Funabashi, Akinobu Sugahara, Akira Tanaka, Masatoshi Toda, Tsuyoshi Ota, Youichi Matsuo, Tsutomu Akimaru, Sigeo Iwasaki, Masayuki Tsuruoka
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Patent number: 5345003Abstract: A method for preparing 2,3-dichloro-1-propanol and 3-chloro-1-propanol is here disclosed which comprises the step of reacting 1,2-dichloroethane with methanol by the irradiation of light in the presence of at least one compound selected from the group consisting of europium compounds, samarium compounds and ytterbium compounds, and if necessary, in the additional presence of a zeolite.Type: GrantFiled: May 18, 1993Date of Patent: September 6, 1994Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Hiroyoshi Watanabe, Fumie Hayakawa
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Patent number: 5292911Abstract: Novel monocyclic terpene derivative of the formula: ##STR1## wherein R is hydrogen atom, trimethylsilyl group or 1-ethoxyethyl group, and novel intermediates therefor. The terpene derivative (I) is a useful intermediate for preparing Sarcophytol A having an anti-carcinogenesis promoter activity and an antitumor activity.Type: GrantFiled: March 10, 1992Date of Patent: March 8, 1994Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 5278319Abstract: An improved process is provided for the production of a partial oxidation product by the vapor phase reaction of a hydrocarbon with substantially pure oxygen in the presence of a suitable catalyst. In the improved process, the partial oxidation product is removed, carbon dioxide and excess carbon monoxide, present in the reactor effluent as by-products, are also removed and the remaining gaseous effluent, comprised mainly of carbon monoxide and unreacted hydrocarbon, is recycled to the reactor. The concentration of carbon monoxide throughout the system is maintained sufficiently high to prevent the formation of a flammable mixture in the reactor or associated equipment.Type: GrantFiled: April 14, 1992Date of Patent: January 11, 1994Assignee: The BOC Group, Inc.Inventors: Ramakrishnan Ramachandran, Loc Dao, Donald L. MacLean
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Patent number: 5254756Abstract: (2R,3E)-4-halo-3-buten-2-ols are produced by kinetic resolution of racemates from the corresponding racemates. The racemate is esterified by reaction with a carboxylic acid derivative, preferably with chloroacetyl chloride. Then the (R)-ester is enantioselectively hydrolyzed with a lipase from Pseudomonas fluorescens. The corresponding (2R,3E)-4-halo-3-buten-2-ol also can be obtained from the remaining (S)-ester after separation. The compounds are chiral synthesis structural elements for the production of optically active natural substances.Type: GrantFiled: November 5, 1992Date of Patent: October 19, 1993Assignee: Lonza Ltd.Inventors: Markus Banziger, John McGarrity
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Patent number: 5237113Abstract: Haloalcohols of the general formula IHal--X--OH (I)where X is straight-chain or branched, substituted or unsubstituted alkylene of 4 or more carbon atoms in the chain, which may be interrupted by one or more heteroatoms, and Hal is halogen, are prepared by reacting a diol of the general formula IIHO--X--OH (II)where X has the above meanings, with an aqueous hydrogen halide solution in a water-immiscible organic solvent which is inert under the reaction conditions, at from 50.degree. to 150.degree. C., using an excess of hydrogen halide, based on the diol of the general formula II, of from 10 to 200 mole percent and setting a volume ratio of inorganic phase: organic phase of from 1:2 to 1:50.Type: GrantFiled: November 9, 1992Date of Patent: August 17, 1993Assignee: BASF AltiengesellschaftInventors: Rainer Becker, Wolfgang Mackenroth, Walter Seufert
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Patent number: 5227540Abstract: A process is described for the preparation of fluoroalcohols of the formula below ##STR1## in which R.sub.f is a perfluoroalkyl radical having 1 to 20 carbon atoms and R is hydrogen or an alkyl radical having 1 to 5 carbon atoms, by reaction of a perfluoroalkylethylene, R.sub.f --CH.dbd.CH.sub.2, and an n-C.sub.1 to C.sub.6 -alkanol in the presence of a free radical initiator, the perfluoroalkylethylene, the alkanol and the free radical initiator being used in the molar ratio of 1 to 20-50 to 0.002-0.2. In the novel process, in addition, the reaction is carried out in a specific manner and under specific reaction conditions. The fluoroalcohols given are obtained in high yield.Type: GrantFiled: July 24, 1992Date of Patent: July 13, 1993Assignee: Hoechst AktiengesellschaftInventor: Wolfgang Knaup
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Patent number: 5202506Abstract: A process for the formation of perfluoroalkylethyl alcohols from perfluoroalkylethyl iodides is disclosed. The process involves treatment of the perfluoroalkylethyl iodide with oleum.Type: GrantFiled: April 2, 1992Date of Patent: April 13, 1993Assignee: E. I. du Pont de Nemours and CompanyInventors: Jack R. Kirchner, Leonard H. Beck, James E. Dowd
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Patent number: 5146011Abstract: Described herein is a process for the preparation of chlorohydrins by reacting a concentrated, aqueous solution of hypochlorous acid with at least one unsaturated organic compound having from 2 to about 10 carbon atoms and selected from the group consisting of substituted or unsubstituted olefins and cyclic olefins.Type: GrantFiled: June 21, 1991Date of Patent: September 8, 1992Assignee: Olin CorporationInventors: Ming Shen, John A. Wojtowicz
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Patent number: 5118881Abstract: The present invention provides for an improved practical process for producing DDTr-free p,p'-dicofol and its formulations substantially free of the practically inactive o-p'-dicofol comprising either directly recrystallizing technical dicofol from a suitable solvent such as acetic acid or alkanes, or alternatively preparing the p,p'-dicofol by the steps of (a) dehydrohalogenating technical DDT to give DDE; (b) chlorinating DDE to give Cl-DDT; and (c) hydrolyzing Cl-DDT to dicofol, wherein the technical DDT is initially recrystallized from a suitable solvent such as lower alkyl alcohols and then recrystallizing the ressulting p,p'-dicofol from a suitable solvent such as acetic acid or alkanes.Type: GrantFiled: November 8, 1990Date of Patent: June 2, 1992Assignee: Agan Chemical Manufacturers, Ltd.Inventors: Bernard Vaisbuch, Benjamin Shifman, Michael Pikarski
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Patent number: 4987236Abstract: Provided herein is an optically active alcohol having a silyl group, stannyl group, or halogen atom at the .gamma.-position, selected from compounds represented by the general formula [I], ##STR1## the general formula [II], ##STR2## the general formula [III], ##STR3## and the general formula [IV], ##STR4## (where, R denotes a C.sub.1 -C.sub.10 substituted or unsubstituted alkyl group or substituted or unsubstituted phenyl group; A denotes a silyl group represented by ##STR5## a stannyl group represented by ##STR6## or a halogen atom, R.sup.1, R.sup.2, and R.sup.3 are substituted or unsubstituted C.sub.1 -C.sub.10 alkyl groups or substituted or unsubstituted phenyl group, which may be the same or different, provided that this does not apply in the case where A represents a stannyl group or halogen atom in the general formulas [III] and [IV].); a process for producing the same, and a process for resolving the optically active alcohol into isomers of high optical purity.Type: GrantFiled: November 17, 1989Date of Patent: January 22, 1991Assignee: Nissan Chemical Industries, Ltd.Inventor: Fumie Sato
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Patent number: 4912253Abstract: An efficient method is proposed for the synthesis of an unsaturated alcohol of the general formula R--CH.dbd.CH(CH.sub.2).sub.n+1 OH, in which R is a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms and the subscript n is an integer in the range from 3 to 10, in which an acetate of the formula R--CH.dbd.CHCH.sub.2 OCOCH.sub.3 is subjected to a coupling reaction with a Grignard reagent of the formula X.sup.1 Mg(CH.sub.2).sub.n OMgX.sup.2, in which X.sup.1 and X.sup.2 are each a halogen atom, and then the reaction product is hydrolyzed. When the reaction product of the coupling reaction is reacted with acetic anhydride instead of hydrolysis, the corresponding acetate can readily be obtained. These unsaturated alcohols and acetates form a class of important biologically active compounds or intermediates thereof including sex pheromone compounds of insects.Type: GrantFiled: May 4, 1989Date of Patent: March 27, 1990Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takehiko Fukumoto, Akira Yamamoto
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Patent number: 4902812Abstract: Provided herein is an optically active alcohol having a silyl group, stannyl group, or halogen atom at the .gamma.-position, selected from compounds represented by the general formula [I], ##STR1## the general formula [II], ##STR2## the general formula [III], ##STR3## and the general formula [IV], ##STR4## (where, R denotes a C.sub.1 -C.sub.10 substituted or unsubstituted alkyl group or substituted or unsubstituted phenyl group; A denotes a silyl group represented by ##STR5## a stannyl group represented by ##STR6## or a halogen atom. R.sup.1, R.sup.2, and R.sup.3 are substituted or unsubstituted C.sub.1 -C.sub.10 alkyl groups or substituted or unsubstituted phenyl group, which may be the same or different, provided that this does not apply in the case where A represents a stannyl group or halogen atom in the general formulas [III] and [IV].); a process for producing the same, and a process for resolving the optically active alcohol into isomers of high optical purity.Type: GrantFiled: July 30, 1987Date of Patent: February 20, 1990Assignee: Nissan Chemical Industries, Ltd.Inventor: Fumie Sato
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Patent number: 4751245Abstract: N-(6,6-dimethyl-2-hepten-4-ynyl)-1-naphthalenemethanamine derivatives are provided having the general formula ##STR1## wherein R.sub.1 is methoxy, iminomethyl or 1-iminoethyl and R.sub.2 and R.sub.3 are each hydrogen; or R.sub.1 is methyl and one of R.sub.2 and R.sub.3 is hydrogen and the other is halogen.The above compounds as well as acid-addition salts thereof are useful as antifungal agents.Type: GrantFiled: June 25, 1986Date of Patent: June 14, 1988Assignee: E. R. Squibb & Sons, Inc.Inventors: Gregory S. Bisacchi, Robert Zahler
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Patent number: 4709059Abstract: Epoxy compounds for use as epoxy resins are prepared from relatively inexpensive and renewable resources via a selective halogenation process. Primary pendant hydroxyl groups on straight carbon chain compounds with oxygen atoms pendant to each carbon are selectively halogenated with, for example, carbon tetrachloride. A scavenger agent, triphenylphosphine and pyridine, is used to complex the residual portion of reacted halogenating agent. One additional step with the halogenated intermediate yields epoxy compounds which, when cured, yield epoxy resins.Type: GrantFiled: August 12, 1985Date of Patent: November 24, 1987Assignee: The Dow Chemical CompanyInventors: Stoil K. Dirlikov, Connie J. Schneider
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Patent number: 4681977Abstract: Chloro-olefins which contain a group of the formula ##STR1## where Y is chlorine or hydrogen, which are prepared by a process in which a trichloromethyl compound which contains a group of the general formula ##STR2## where X is hydrogen or an organic radical, is reduced with a chromium(II) salt in an aqueous medium.Type: GrantFiled: June 27, 1985Date of Patent: July 21, 1987Assignee: BASF AktiengesellschaftInventors: Eberhard Steckhan, Reinhard Wolf, Hermann Puetter
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Patent number: 4681959Abstract: A number of processes for the formation of insoluble metal alkoxides are disclosed. In one embodiment, there is disclosed a two step process wherein a halide of an at least divalent metal is reacted with an appropriate alcohol in the first step. In the second step, the intermediate compound formed is then reacted with more alcohol, said alcohol forming part of a solvent system in which the final metal alkoxide formed is insoluble. In another embodiment, a two step process is disclosed wherein the intermediate formed in the first step is isolated, and then in the second step the intermediate is reacted with an appropriate alcohol to yield the final product. The final embodiment of the present invention comprises a one step process for the production of insoluble metal alkoxides wherein a halide of an at least divalent metal is reacted with an appropriate alcohol in the presence of an excess amount of a hydrogen halide acceptor in a solvent in which the hydrogen halide compound formed is soluble.Type: GrantFiled: April 22, 1985Date of Patent: July 21, 1987Assignee: Stauffer Chemical CompanyInventors: Richard J. Ayen, Johst H. Burk, Carl C. Greco