Oxirane Ring And Chalcogen, Cyano, Nitrogen, Or Halogen Are Bonded Directly To The Same Carbon (e.g., Glycidyl Ester Formed, Etc.) Patents (Class 549/521)
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Patent number: 9963436Abstract: A process for manufacturing epoxy monomers and/or epoxides in high yields and useful quality and chemical stability by dehydrochlorination of the corresponding chlorohydrins with an alkaline agent, producing the corresponding side product dry salt in a high purity, characterized in that the process comprises the following steps: a. Reaction of the chlorohydrins with the alkaline agent to form corresponding epoxides and the corresponding precipitated chloride salt; b. Dehydration, and optionally completing the reaction, of the reaction mixture of step (a), by use of an azeotropic agent, added to step (b) or generated in situ in step (a), resulting in the producing of a dehydrated reaction mixture; c. Separating the resulting chloride salt by filtration from the dehydrated reaction mixture (b) and d. Isolating the epoxide from the filtered liquid fraction.Type: GrantFiled: February 8, 2017Date of Patent: May 8, 2018Assignee: SPOLEK PRO CHEMICKOU A HUTNI VYROBUInventors: Pavel Kubicek, Bedrich Nemecek, Petr Sladek
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Patent number: 8975449Abstract: A method of preparing chlorohydrins and a method of preparing epichlorohydrin by using chlorohydrins prepared using the method are provided. The method of preparing chlorohydrins by reacting polyhydroxy aliphatic hydrocarbon with a chlorination agent in the presence of a catalyst includes at least one combination of a series of unit operations including a first reaction step, a water removal step, and a second reaction step, in that respective order, and after mixing at least a portion of a reaction mixture discharged from at least one reaction steps from among the plurality of reaction steps with an additional chlorination agent, recirculating the resulting mixture to the reaction step from which the reaction mixture was discharged. The method of preparing epichlorohydrin includes a step of reacting chlorohydrins prepared using the method of preparing chlorohydrins, with an alkaline agent.Type: GrantFiled: June 8, 2011Date of Patent: March 10, 2015Assignee: Samsung Fine Chemicals Co., Ltd.Inventors: Won Seob Song, Sung Yul Woo, Boo Weon Song, Seong Han Park, Myoung Suk Kwon
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Patent number: 8969601Abstract: Disclosed are a method for preparing chlorohydrins composition and a method for preparing epichlorohydrin using chlorohydrins prepared thereby. The disclosed method for preparing chlorohydrins composition reacts polyhydroxy aliphatic hydrocarbon with a chlorination agent in the presence of a catalyst, comprises at least one combination of a series of unit operations including a first reaction step, a water removal step, and a second reaction step in the respective order, and additionally comprises a step for reacting the chlorohydrins composition derived from a plurality of reaction mixtures discharged from the plurality of reaction steps with an alkaline chemical, and removing the catalyst included in the chlorohydrins composition in the form of an alkali metal salt. The disclosed method for preparing epichlorohydrin includes a step for contacting the chlorohydrins composition, which was prepared using the method for preparing chlorohydrins composition, with an alkaline chemical.Type: GrantFiled: June 8, 2011Date of Patent: March 3, 2015Assignee: Samsung Fine Chemicals Co., Ltd.Inventors: Won Seob Song, Sung Yul Woo, Boo Weon Song, Seong Han Park, Myoung Suk Kwon
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Patent number: 8969631Abstract: A method of preparing a chlorohydrin composition and a method of preparing epichlorohydrin by using a chlorohydrin composition prepared by using the method are provided. The method of preparing a chlorohydrin composition in which a polyhydroxy aliphatic hydrocarbon is reacted with a chlorination agent in the presence of a catalyst includes performing at least one combination of a series of unit operations comprising a first reaction step, a water removal step, and a second reaction step in this stated order, wherein the method further includes mixing a chlorohydrin concentrate obtained by purifying the reaction mixture discharged from the final reaction step from among the plurality of reaction steps and a water-rich layer discharged from the water-removal step. The method of preparing epichlorohydrin includes contacting the chlorohydrin composition prepared by using the method of preparing a chlorohydrin composition with an alkaline agent.Type: GrantFiled: June 8, 2011Date of Patent: March 3, 2015Assignee: Samsung Fine Chemicals Co., Ltd.Inventors: Won Seob Song, Sung Yul Woo, Boo Weon Song, Seong Han Park, Myoung Suk Kwon
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Patent number: 8921585Abstract: The present invention provides an efficient method of synthesizing and purifying dianhydrohexitols such as dianhydrogalactitol. In general, as applied to dianhydrogalactitol, the method comprises: (1) reacting dulcitol with a concentrated solution of hydrobromic acid at a temperature of about 80° C. to produce dibromogalactitol; (2) reacting the dibromogalactitol with potassium carbonate in t-butanol to produce dianhydrogalactitol; and (3) purifying the dianhydrogalactitol using a slurry of ethyl ether to produce purified dianhydrogalactitol. Another method produces dianhydrogalactitol from dulcitol; this method comprises: (1) reacting dulcitol with a reactant to convert the 1,6-hydroxy groups of dulcitol to an effective leaving group to generate an intermediate; and (2) reacting the intermediate with an inorganic weak base to produce dianhydrogalactitol through an intramolecular SN2 reaction. Other methods for the synthesis of dianhydrogalactitol from dulcitol are described.Type: GrantFiled: July 2, 2013Date of Patent: December 30, 2014Assignee: Del Mar PharmaceuticalsInventor: Dennis M. Brown
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Publication number: 20130281721Abstract: Processes and apparatus for purifying brine are provided including (1) providing an aqueous brine solution comprising one or more inorganic salts and one or more organic compounds and (2) conducting at least one unit operation for removing organic compounds from the brine solution to obtain a purified brine solution.Type: ApplicationFiled: June 20, 2013Publication date: October 24, 2013Inventors: Bruce Hook, Dan Tirtowidjojo, Anil Mehta
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Patent number: 8563758Abstract: The present invention provides an efficient method of synthesizing and purifying dianhydrohexitols such as dianhydrogalactitol. In general, as applied to dianhydrogalactitol, the method comprises: (1) reacting dulcitol with a concentrated solution of hydrobromic acid at a temperature of about 80° C. to produce dibromogalactitol; (2) reacting the dibromogalactitol with potassium carbonate in t-butanol to produce dianhydrogalactitol; and (3) purifying the dianhydrogalactitol using a slurry of ethyl ether to produce purified dianhydrogalactitol.Type: GrantFiled: August 17, 2011Date of Patent: October 22, 2013Assignee: Del Mar PharmaceuticalsInventor: Dennis M. Brown
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Patent number: 8558021Abstract: The present invention relates to a process for the catalytic halogenation of an organic compound comprising at least one vicinal diol moiety, said process comprising a step of bringing the organic compound comprising at least one vicinal diol moiety into contact with a hydrogen halide in the presence of a catalyst, characterized in that the catalyst is an organic compound comprising a ?-diketone moiety or a ?-keto aldehyde moiety.Type: GrantFiled: March 17, 2010Date of Patent: October 15, 2013Assignee: Akzo Nobel N.V.Inventors: Antoon Jacob Berend Ten Kate, Richard Herman Woudenberg, Eilertdina Henderika Renkema, Luc Louis Theophile Vertommen, Carolina Anna Maria Christina Dirix, Tim Baks
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Publication number: 20130211111Abstract: The present invention provides an efficient method of synthesizing and purifying dianhydrohexitols such as dianhydrogalactitol. In general, as applied to dianhydrogalactitol, the method comprises: (1) reacting dulcitol with a concentrated solution of hydrobromic acid at a temperature of about 80° C. to produce dibromogalactitol; (2) reacting the dibromogalactitol with potassium carbonate in t-butanol to produce dianhydrogalactitol; and (3) purifying the dianhydrogalactitol using a slurry of ethyl ether to produce purified dianhydrogalactitol.Type: ApplicationFiled: August 17, 2011Publication date: August 15, 2013Applicant: Del Mar PharmaceuticalsInventor: Dennis M. Brown
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Publication number: 20130090485Abstract: A method of preparing chlorohydrins and a method of preparing epichlorohydrin by using chlorohydrins prepared using the method are provided. The method of preparing chlorohydrins by reacting polyhydroxy aliphatic hydrocarbon with a chlorination agent in the presence of a catalyst includes at least one combination of a series of unit operations including a first reaction step, a water removal step, and a second reaction step, in that respective order, and after mixing at least a portion of a reaction mixture discharged from at least one reaction steps from among the plurality of reaction steps with an additional chlorination agent, recirculating the resulting mixture to the reaction step from which the reaction mixture was discharged. The method of preparing epichlorohydrin includes a step of reacting chlorohydrins prepared using the method of preparing chlorohydrins, with an alkaline agent.Type: ApplicationFiled: June 8, 2011Publication date: April 11, 2013Inventors: Won Seob Song, Sung Yul Woo, Boo Weon Song, Seong Han Park, Myoung Suk Kwon
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Patent number: 8389777Abstract: Continuous process for producing a chlorohydrin, wherein a polyhydroxylated aliphatic hydrocarbon, an ester of a polyhydroxylated aliphatic hydrocarbon or a mixture thereof is reacted with a chlorinating agent and an organic acid in a liquid reaction medium whose steady-state composition comprises the polyhydroxylated aliphatic hydrocarbon and esters of the polyhydroxylated aliphatic hydrocarbon whose sum content, expressed as moles of polyhydroxylated aliphatic hydrocarbon, is greater than 1.1 mol % and less than or equal to 30 mol %, the percentage being based on the organic part of the liquid reaction medium.Type: GrantFiled: May 19, 2006Date of Patent: March 5, 2013Assignee: Solvay (Société Anonyme)Inventor: Patrick Gilbeau
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Publication number: 20130053557Abstract: Processes and intermediates for preparing linezolid, and pharmaceutically acceptable salts thereof, are described herein.Type: ApplicationFiled: April 28, 2011Publication date: February 28, 2013Applicant: INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATIONInventor: James R. McCarthy
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Patent number: 8304563Abstract: The present invention relates to a process for converting a multihydroxylated-aliphatic hydrocarbon or ester thereof to a chlorohydrin, by contacting the multihydroxylated-aliphatic hydrocarbon or ester thereof starting material with a source of hydrogen chloride at superatmospheric, atmospheric and subatmospheric pressure conditions for a sufficient time and at a sufficient temperature, preferably wherein such contracting step is carried out without substantial removal of water, to produce the desired chlorohydrin product; wherein the desired product or products can be made in high yield without substantial formation of undesired overchlorinated byproducts; said process carried out without a step undertaken to specifically remove volatile chlorinated hydrocarbon by-products or chloroacetone, wherein the combined concentration of volatile chlorinated hydrocarbon by-products and chloroacetone is less than 2000 ppm throughout any stage of the said process.Type: GrantFiled: January 31, 2011Date of Patent: November 6, 2012Assignee: Dow Global Technologies LLCInventors: William J. Kruper, Tina Arrowood, Bruce M. Bell, John Briggs, Robert M. Campbell, Bruce D. Hook, Anh Nguyen, Curt Theriault, Ralf Fitschen
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Patent number: 8236975Abstract: A process for converting a crude glycerol, crude mixtures of naturally derived multihydroxylated-aliphatic hydrocarbons or esters thereof to a chlorohydrin, by contacting the crude glycerol, crude mixtures of naturally derived multihydroxylated-aliphatic hydrocarbons or esters thereof starting material with a source of a superatmospheric partial pressure of hydrogen chloride for a sufficient time and at a sufficient temperature, and wherein such contracting step is carried out without substantial removal of water, to produce the desired chlorohydrin product; wherein the desired product or products can be made in high yield without substantial formation of undesired overchlorinated byproducts; wherein said crude glycerol, said ester of crude glycerol, or mixture thereof is derived from a renewable raw material. Chlorohydrins made by the process of the present invention are useful in preparing epoxides such as epichlorohydrins.Type: GrantFiled: February 9, 2011Date of Patent: August 7, 2012Inventors: Bruce D. Hook, John Briggs, Robert M. Campbell, William J. Kruper, David J. Schreck, Richard D. Varjian, Jeffrey G. Hippler
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Publication number: 20120004432Abstract: The present invention relates to a process for the catalytic halogenation of an organic compound comprising at least one vicinal diol moiety, said process comprising a step of bringing the organic compound comprising at least one vicinal diol moiety into contact with a hydrogen halide in the presence of a catalyst, characterized in that the catalyst is an organic compound comprising a ?-diketone moiety or a ?-keto aldehyde moiety.Type: ApplicationFiled: March 17, 2010Publication date: January 5, 2012Applicant: AKZO NOBEL N.V.Inventors: Antoon Jacob Berend Ten Kate, Richard Herman Woudenberg, Eilertdina Henderika Renkema, Luc Louis Theophile Vertommen, Carolina Anna Maria Christina Dirix, Tim Baks
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Patent number: 8067645Abstract: Process for producing a chlorohydrin by reaction between a multihydroxylated-aliphatic hydrocarbon, an ester of a multihydroxylated-aliphatic hydrocarbon, or a mixture thereof, and a chlorinating agent, according to which the multihydroxylated-aliphatic hydrocarbon, the ester of a multihydroxylated-aliphatic hydrocarbon, or the mixture thereof used contains at least one solid or dissolved metal salt, the process comprising a separation operation to remove at least part of the metal salt.Type: GrantFiled: May 19, 2006Date of Patent: November 29, 2011Assignee: Solvay (Societe Anonyme)Inventors: Patrick Gilbeau, Ivan de Andolenko, Philippe Krafft, Freddy Gielen
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Patent number: 7985867Abstract: A process for producing epoxides, the process including: (a) feeding at least one aqueous alkali and at least one halohydrin to a reactive distillation column, wherein the reactive distillation column includes a feed zone, a top zone disposed above the feed zone, and a bottom zone disposed below the feed zone; (b) concurrently in the reactive distillation column: (i) reacting at least a portion of the halohydrin with the alkali to form an epoxide; and (ii) stripping water and the epoxide from a basic aqueous residue; (c) recovering the water and the epoxide from the reactive distillation column as an overheads fraction; (d) condensing and phase separating the overheads fraction to form an organic overheads fraction including the epoxide and an aqueous overheads fraction including water; and (e) maintaining a liquid holdup per plate in the feed zone at a residence time of 10 seconds or less.Type: GrantFiled: July 23, 2009Date of Patent: July 26, 2011Assignee: Dow Global Technologies LLCInventors: William W. Fan, Christian D. Kneupper, Sascha Noormann, Renate Patrascu
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Publication number: 20110178315Abstract: A process for converting a crude glycerol, crude mixtures of naturally derived multihydroxylated-aliphatic hydrocarbons or esters thereof to a chlorohydrin, by contacting the crude glycerol, crude mixtures of naturally derived multihydroxylated-aliphatic hydrocarbons or esters thereof starting material with a source of a superatmospheric partial pressure of hydrogen chloride for a sufficient time and at a sufficient temperature, and wherein such contracting step is carried out without substantial removal of water, to produce the desired chlorohydrin product; wherein the desired product or products can be made in high yield without substantial formation of undesired overchlorinated byproducts; wherein said crude glycerol, said ester of crude glycerol, or mixture thereof is derived from a renewable raw material. Chlorohydrins made by the process of the present invention are useful in preparing epoxides such as epichlorohydrins.Type: ApplicationFiled: February 9, 2011Publication date: July 21, 2011Applicant: DOW GLOBAL TECHNOLOGIES LLCInventors: Bruce D. Hook, John Briggs, Robert M. Campbell, William J. Kruper, JR., David J. Schreck, Richard D. Varjian, Jeffrey G. Hippler
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Patent number: 7982061Abstract: A process for producing epoxides, the process including: (a) feeding at least one aqueous alkali and at least one halohydrin to a reactive distillation column; (b) concurrently in the reactive distillation column: (i) reacting at least a portion of the halohydrin with the alkali to form an epoxide; and (ii) stripping water and the epoxide from a basic aqueous residue; (c) recovering the water and the epoxide from the reactive distillation column as an overheads fraction; and, (d) condensing and phase separating the overheads fraction at a temperature of 50° C. or less to form an organic overheads fraction including the epoxide and an aqueous overheads fraction including water.Type: GrantFiled: July 23, 2009Date of Patent: July 19, 2011Inventors: William W. Fan, Christian D. Kneupper, Sascha Noormann, Renate Patrascu
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Publication number: 20110166369Abstract: Process for purifying hydrogen chloride, comprising at least one step of bringing said hydrogen chloride into contact with a scrubbing agent containing at least one chlorohydrin.Type: ApplicationFiled: September 11, 2009Publication date: July 7, 2011Applicant: SOLVAY SAInventors: Philippe Krafft, Patrick Gilbeau
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Publication number: 20110124892Abstract: The present invention relates to a process for converting a multihydroxylated-aliphatic hydrocarbon or ester thereof to a chlorohydrin, by contacting the multihydroxylated-aliphatic hydrocarbon or ester thereof starting material with a source of hydrogen chloride at superatmospheric, atmospheric and subatmospheric pressure conditions for a sufficient time and at a sufficient temperature, preferably wherein such contracting step is carried out without substantial removal of water, to produce the desired chlorohydrin product; wherein the desired product or products can be made in high yield without substantial formation of undesired overchlorinated byproducts; said process carried out without a step undertaken to specifically remove volatile chlorinated hydrocarbon by-products or chloroacetone, wherein the combined concentration of volatile chlorinated hydrocarbon by-products and chloroacetone is less than 2000 ppm throughout any stage of the said process.Type: ApplicationFiled: January 31, 2011Publication date: May 26, 2011Inventors: William J. Kruper, JR., Tina Arrowood, Bruce Michael Bell, John Briggs, Robert M. Campbell, Bruce D. Hook, Anh Nguyen, Curt Theriault, Ralf Fitschen
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Patent number: 7931946Abstract: Disclosed are a novel liquid crystal compound containing a sulfone group, a liquid crystal composition comprising the same, and an optical film using the same liquid crystal composition. More particularly, there are provided a liquid crystal material for a viewing angle compensation film with high quality characteristics, which can improve a contrast ratio measured at a tilt angle to the front and minimize variations in color with viewing angles in a black state, a liquid crystal composition comprising the same liquid crystal material, and a compensation film obtained from the same liquid crystal composition.Type: GrantFiled: January 22, 2008Date of Patent: April 26, 2011Assignee: LG Chem, Ltd.Inventors: Jae-Ho Cheong, Min-Jin Ko, Myung-Sun Moon, Bum-Gyu Choi, Dae-Ho Kang, Ki-Youl Lee, Yun-Bong Kim
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Patent number: 7906691Abstract: Process for preparing a chlorohydrin, comprising a step in which a polyhydroxylated aliphatic hydrocarbon, an ester of a polyhydroxylated aliphatic hydrocarbon or a mixture thereof is subjected to reaction with a chlorinating agent containing hydrogen chloride and at least one other step, carried out in apparatus made from or covered with materials which are resistant to the chlorinating agent under the conditions in which this step is realized.Type: GrantFiled: May 19, 2006Date of Patent: March 15, 2011Assignee: Solvay (Societe Anonyme)Inventors: Philippe Krafft, Patrick Gilbeau, Dominique Balthasart, Valentine Smets, Christian Franck
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Publication number: 20100331555Abstract: A process and apparatus are disclosed for the purification of epichlorohydrin. The process includes distilling and/or fractionating a feed stream containing epichlorohydrin, dichlorohydrin(s), and one or more other substances, subjecting at least a portion of the liquid phase effluent to a dichlorohydrin dehydrochlorination process for converting residual dichlorohydrin(s) in the liquid phase effluent to epichlorohydrin, and recovering purified epichlorohydrin from the vapor phase effluent in which the distillation/fractionation pressure and/or temperature of step (1) is adjusted to retain at least 5 weight-percent epichlorohydrin in the liquid phase effluent. The apparatus for making purified epichlorohydrin includes a dehydrochlorination apparatus, a first liquid-vapor contacting apparatus, and a second liquid-vapor contacting apparatus connected to the dehydrochlorination apparatus for recycling a distillate to the dehydrochlorination apparatus.Type: ApplicationFiled: January 22, 2009Publication date: December 30, 2010Inventors: Christian D. Kneupper, Perry S. Basile, William W. Fan, Sascha Noormann
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Publication number: 20100029959Abstract: A process for producing epoxides, the process including: (a) feeding at least one aqueous alkali and at least one halohydrin to a reactive distillation column, wherein the reactive distillation column includes a feed zone, a top zone disposed above the feed zone, and a bottom zone disposed below the feed zone; (b) concurrently in the reactive distillation column: (i) reacting at least a portion of the halohydrin with the alkali to form an epoxide; and (ii) stripping water and the epoxide from a basic aqueous residue; (c) recovering the water and the epoxide from the reactive distillation column as an overheads fraction; (d) condensing and phase separating the overheads fraction to form an organic overheads fraction including the epoxide and an aqueous overheads fraction including water; and (e) maintaining a liquid holdup per plate in the feed zone at a residence time of 10 seconds or less.Type: ApplicationFiled: July 23, 2009Publication date: February 4, 2010Applicant: DOW GLOBAL TECHNOLOGIES INC.Inventors: William W. Fan, Christian D. Kneupper, Sascha Noormann, Renate Patrascu
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Publication number: 20090275726Abstract: Process for producing epichlorohydrin comprising subjecting to a dehydrochlorination operation, dichloropropanol produced from glycerol comprising aldehydes.Type: ApplicationFiled: July 14, 2009Publication date: November 5, 2009Applicant: SOLVAY (SOCIETE ANONYME)Inventors: Philippe KRAFFT, Patrick Gilbeau, Benoît Gosselin, Sara Claessens
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Publication number: 20090270588Abstract: Process for producing dichloropropanol wherein glycerol is reacted with at least one chlorinating agent in a reactor made of or coated with materials selected from enamelled steel, polyolefins, fluorinated polymers, phenolic resins, tantalum, and silver.Type: ApplicationFiled: July 14, 2009Publication date: October 29, 2009Applicant: SOLVAY (SOCIETE ANONYME)Inventors: Philippe KRAFFT, Patrick Gilbeau, Benoit Gosselin, Sara Claessens
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Patent number: 7582781Abstract: The present invention provides an industrially safe, easily operable process for producing an optically active epoxy alcohol derivative useful as an intermediate for pharmaceuticals from inexpensively available materials, and also provides a novel halohydrin derivative serving as an important intermediate for the epoxy alcohol derivative. Furthermore, the present invention provides a process for producing an intermediate for a triazole antifungal agent by allowing a halohydrin to react with a triazole sulfonamide, the process including a small number of steps.Type: GrantFiled: July 5, 2004Date of Patent: September 1, 2009Assignee: Kaneka CorporationInventors: Kazumi Okuro, Tatsuyoshi Tanaka, Masaru Mitsuda, Kenji Inoue
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Publication number: 20080207930Abstract: Process for producing a chlorohydrin by reaction between a multihydroxylated-aliphatic hydrocarbon, an ester of a multihydroxylated-aliphatic hydrocarbon, or a mixture thereof, and a chlorinating agent, according to which the multihydroxylated-aliphatic hydrocarbon, the ester of a multihydroxylated-aliphatic hydrocarbon, or the mixture thereof used contains at least one solid or dissolved metal salt, the process comprising a separation operation to remove at least part of the metal salt.Type: ApplicationFiled: May 19, 2006Publication date: August 28, 2008Inventors: Patrick Gilbeau, Ivan de Andolenko, Philippe Krafft, Freddy Gielen
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Patent number: 7405312Abstract: The present invention relates to a method for preparing hexafluoropropylene oxide with high yield, and particularly to a method for preparing hexafluoropropylene oxide comprising the step of performing a two-phase interfacial reaction between an organic phase containing hexafluoropropylene and an aqueous phase containing a hypochlorite oxidant in the presence of a phase-transfer catalyst and a non-ionic surfactant to improve the degree of emulsification and dispersion of the organic phase and to increase the contact interfacial area, thereby increasing the efficiency and the yield of the reaction.Type: GrantFiled: February 5, 2007Date of Patent: July 29, 2008Assignee: Korea Research Institute of Chemical TechnologyInventors: Soo Bok Lee, In Jun Park, Dong-Kwon Kim, Jeong-Hoon Kim, Jong-Wook Ha, Bong-Jun Chang, Kwang-won Lee, Kwang-Han Kim, Jaewon Kim
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Patent number: 6946566Abstract: A process for preparing regioselectively an optically active 1-halogeno-2-hydroxypropyl compound of the following formula; wherein X is halogen atom and Nu is a heteroatom having a substituent, and an optically active glycidyl compound of the formula; which comprises reacting an optically active epihalohydrin of the formula; with a neucleophilic agent, in the presence of a metal complex of the formula; wherein n is an integer of 0, 1 or 2, Y1, Y2 and Y3 are hydrogen atom, etc., and Y2 and Y3 may form a ring such as benzene, A is a counterion and M is a metal ion, and further subjecting the compound (4) to reaction with a base to prepare the optically active glycidyl compound (5).Type: GrantFiled: July 30, 2003Date of Patent: September 20, 2005Assignee: Daiso Co., Ltd.Inventors: Keisuke Yaegashi, Yoshiro Furukawa
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Patent number: 6765100Abstract: The invention relates to a method for industrially producing highly pure (2R, 3S)- or (2S, 3R)-N-carbamate-protected &bgr;-aminoepoxide (crystal) or (2R, 3S)- or (2S, 3R)-N-carbamate-protected &bgr;-aminoalcohol.Type: GrantFiled: October 10, 2001Date of Patent: July 20, 2004Assignee: Ajinomoto Co., Inc.Inventors: Tomoyuki Onishi, Naoko Hirose, Yasuyuki Otake, Takashi Nakano, Yutaka Honda, Masakazu Nakazawa, Kunisuke Izawa
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Patent number: 6764545Abstract: The present invention provides a production method including adding water to a solution of (2R,3S)-3-tert-butoxycarbonylamino-1,2-epoxy-4-phenylbutane ((2R,3S)-epoxide compound) or (2S,3R)-3-tert-butoxycarbonylamino-1,2-epoxy-4-phenylbutane ((2S,3R)-epoxide compound) in a polar solvent to allow crystallization, whereby to produce crystals of the (2R,3S)-epoxide compound or the (2S,3R)-epoxide compound conveniently in a high yield by an industrial production method without requiring an extremely low temperature.Type: GrantFiled: December 11, 2001Date of Patent: July 20, 2004Assignee: Ajinomoto Co., Inc.Inventors: Yuichi Suzuki, Naoko Hirose, Tomoyuki Onishi, Kunisuke Izawa
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Patent number: 6639085Abstract: A process for producing propylene oxide, which comprises steps described below, wherein the concentration of water in a solution containing isopropylbenzene hydroperoxide to be supplied to the epoxidation step is 1% by weight or less: oxidation step; a step in which isopropylbenzene is oxidized to obtain isopropylbenzene hydroperoxide, epoxidation step; a step in which isopropylbenzene hydroperoxide obtained in the oxidation step is reacted with propylene to obtain propylene oxide and cumyl alcohol, and hydrogenolysis step; a step in which cumyl alcohol obtained in the epoxidation step is subjected to hydrogenolysis to obtain isopropylbenzene, and said isopropylbenzene is recycled to the oxidation step as a raw material for the oxidation step.Type: GrantFiled: September 12, 2002Date of Patent: October 28, 2003Assignee: Sumitomo Chemical Company, LimitedInventors: Junpei Tsuji, Jun Yamamoto
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Patent number: 6586607Abstract: A process for the preparation of diglycidylether of alkoxylated resorcinol using novel catalysts is disclosed. In particular, it has been found that antimony, indium and tellurium halides are effective catalysts for preparation of the diglycidylether of alkoxylated resorcinol.Type: GrantFiled: April 11, 2002Date of Patent: July 1, 2003Assignee: Indspec Chemical CorporationInventors: Raj B. Durairaj, Gary A. Jesionowski
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Publication number: 20010018532Abstract: A process for producing (2R,3S)-3-amino-4-phenylbutane-1,2-epoxide compounds which comprises treating a (2S,3S)-3-amino-1-halo-2-hydroxy-4-phenylbutane compound a (2S,3S)-3-amino-4-phenylbutane-1,2-epoxide with a carboxylic acid quaternary ammonium salt or a carboxylic acid metal salt a quaternary ammonium salt and a quaternary ammonium salt, to give a (2S,3S)-1-acyloxy-3-amino-2-hydroxy-4-phenylbutane compound, further treating the same with a sulfonic acid halide in the presence of an organic base to give a (2S,3S)-1-acyloxy-3-amino-2-sulfonyloxy-4-phenylbutane compound furthermore treating said compound with an inorganic base.Type: ApplicationFiled: May 11, 2001Publication date: August 30, 2001Applicant: KANEKA CORPORATIONInventors: Kazumi Okuro, Kenji Inoue
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Patent number: 5965753Abstract: A process for preparation of a glycidyl sulfonate derivative with high purity and in high yield, which is characterized in reacting glycidol which is prepared from treating 3-chloro-1,2-propanediol in an aqueous solvent in the basic condition, without isolating the resulting glycidol with a sulfonyl halide in a two phase solvent consisting of an organic solvent and water in the presence of an inorganic base and a tertiary amine or a pyridine derivative.Type: GrantFiled: July 20, 1998Date of Patent: October 12, 1999Assignee: Daiso Co., LTd.Inventors: Midori Masaki, Yoshiro Furukawa, Keishi Takenaka
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Patent number: 5936104Abstract: The present invention provides a process for producing 1,2-epoxy-3-amino-4-phenylbutane derivatives which comprises treating a 1-halo-2-hydroxy-3-amino-4-phenylbutane derivative with a base in an aprotic polar organic solvent or a mixed solvent composed of an aprotic polar organic solvent and water and then causing the resulting epoxide to crystallize out from a mixed solvent composed of an aprotic polar organic solvent and water.Type: GrantFiled: August 8, 1997Date of Patent: August 10, 1999Assignee: Kaneka CorporationInventors: Akira Nishiyama, Tadashi Sugawa, Hajime Manabe, Kenji Inoue, Noritaka Yoshida
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Patent number: 5847169Abstract: A process for preparing oxiranemethane derivatives which are useful as intermediates for preparing aspartyl protease inhibitors comprising the steps of activating an aminodiol, acylating the aminodiol and reacting the acylated aminodiol with a base to form an epoxy compound.Type: GrantFiled: April 25, 1997Date of Patent: December 8, 1998Assignee: Boehringer Ingelheim Pharmaceuticals, Inc.Inventors: Laurence J. Nummy, Denis P. Byrne
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Patent number: 5824821Abstract: The invention provides a process for the production of a 2,3-dihydroxypropylamino compound, said process comprising the reaction steps of:(i) obtaining an allylamino compound;(ii) epoxidizing said allylamino compound to yield an epoxypropylamino compound; and(iii) hydrolysing said epoxypropylamino compound to yield a 2,3-dihydroxypropylamino compound.This process may be used to produce simple 2,3-dihydroxypropylamino compounds such as APD or complex ones such as BAPD (an intermediate in the production of iohexol).Type: GrantFiled: February 7, 1997Date of Patent: October 20, 1998Assignee: Nycomed Imaging ASInventors: David Redick Lane, Janis Vasilevskis
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Patent number: 5637740Abstract: The reaction mixture obtained in the production of 2,3-epoxypropyltrialkylammonium chlorides by treatment of chlorohydroxypropyltrialkylammonium chlorides with alkaline acting materials in aqueous medium containing impurities which create problems in the subsequent use of the 2,3-epoxypropyltrialkylammonium chloride. According to the invention the reaction mixture is freed from these impurities by separating it from undissolved impurities by employing at least about 0.2 mole of 2,3-epoxypropyltrialkylammonium chloride per mole of water.Type: GrantFiled: March 8, 1995Date of Patent: June 10, 1997Assignee: Degussa AktiengesellschaftInventors: Wolfgang Fischer, Manfred Langer, Gert Roessler
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Patent number: 5589554Abstract: An adhesive composition is here disclosed which comprises a 2-cyanoacrylate and at least one of compounds (a) and (b):(a) an addition reaction product of an epoxy group and a compound having a cyano group and a carboxylic acid group in its molecule, and(b) a compound having a cyano group and a carboxylic acid group in its molecule. A process for preparing the adhesive composition is also disclosed herein. According to the present invention, the 2-cyanoacrylate-based adhesive composition can be obtained which is excellent in storage stability and hardening properties of thick films and which has a high hardening rate and remarkably improved surface hardening properties of the adhesive composition itself bulged from between adherends. Particularly, the 2-cyanoacrylate bulged from between the adherends can harden rapidly, so that the vaporization of the 2-cyanoacrylate can be minimized.Type: GrantFiled: September 16, 1994Date of Patent: December 31, 1996Assignee: Three Bond Co., Ltd.Inventor: Soichiro Hiraoka
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Patent number: 5532389Abstract: A process of preparing alkylene oxides comprises steps of: (1) optionally forming a hypochlorite solution; (2) contacting chlorine with a solution of a hypochlorite below about 60.degree. C., and a pH of less than about 5.5, with sufficient micromixing to achieve a product hypochlorous acid in a yield of at least about 80 percent; (3) separating at least a portion the hypochlorous acid from an aqueous metal chloride solution wherein the solution is sprayed as droplets; (4) distilling the remaining liquid phase; (5) absorbing the hypochlorous acid and dichlorine monoxide in low-chlorides water to produce a low-chlorides aqueous hypochlorous acid solution; (6) contacting the low-chlorides aqueous hypochlorous acid solution with an olefin in a continuous process to form a olefin chlorohydrin; (7) optionally contacting the olefin chlorohydrin with a base to form a alkylene oxide and a salt solution; and (8) optionally separating the alkylene oxide from the salt solution.Type: GrantFiled: September 9, 1994Date of Patent: July 2, 1996Assignee: The Dow Chemical CompanyInventors: David L. Trent, George J. Quarderer, Kim G. Bargeron, Douglas C. Greminger, David J. Koranek, Erik J. Stewart, Curtis N. Swisher, Cheryl A. Tirtowidjojo, Danil Tirtowidjojo
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Patent number: 5523425Abstract: In a process for producing a chlorohydrin an olefinically unsaturated compound is reacted with chlorine in the presence of water. Water is applied as a film on a solid support in a reaction zone and/or water droplets are dispersed in the reaction zone. The reaction is conducted at a pressure of up to about 10 bar.Type: GrantFiled: December 21, 1994Date of Patent: June 4, 1996Assignee: The Dow Chemical CompanyInventors: Gunther A. Pech, Werner J. Witzl
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Patent number: 5486627Abstract: Described herein is a method for producing epoxides which is continuous, inhibits formation of chlorinated byproducts, and eliminates or substantially reduces waste water discharge. The method includes:(a) forming a low chlorides aqueous hypochlorous acid solution;(b) contacting the low chlorides aqueous hypochlorous acid solution with at least one unsaturated organic compound to form an aqueous organic product comprising at least olefin chlorohydrin;(c) contacting at least the olefin chlorohydrin with an aqueous alkali metal hydroxide to form an aqueous salt solution product containing at least epoxide; and(d) isolating the epoxide from the aqueous salt solution;wherein water is recovered from the product of at least Step (b) and recycled into Step (a) for use in forming the low chlorides aqueous hypochlorous acid solution.Type: GrantFiled: December 2, 1994Date of Patent: January 23, 1996Assignee: The Dow Chemical CompanyInventors: George J. Quarderer, Jr., Curtis N. Swisher, David L. Trent
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Patent number: 5466764Abstract: There are here disclosed an adhesive composition obtained by adding a fluorine-containing carboxylic acid epoxy adduct to a 2-cyanoacrylate, and a process for preparing the adhesive composition. This 2-cyanoacrylate-based adhesive composition is excellent in storage stability and particularly excellent in adhesive force and impact resistance and has a high hardening rate. In particular, the adhesive strength of the 2-cyanoacrylate-based adhesive composition can be remarkably increased without lowering the hardening rate, and so the 2-cyanoacrylate-based adhesive composition can exert a sufficient resistance to impact and the like at the time of the adhesion of metals, rubbers, plastics and lumbers and the reliability of adherends can be improved.Type: GrantFiled: September 16, 1994Date of Patent: November 14, 1995Assignee: Three Bond Co., Ltd.Inventor: Soichiro Hiraoka
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Patent number: 5428180Abstract: A method is provided for oxidizing alkenes to epoxides by treating the alkene with a transition metal ion complex which includes a salen or salophen derivative and peroxymonosulfate ion or hypochlorite ion in a two phase system with a phase transfer catalyst, a water phase having a pH from about 6 to about 12.9 and an inorganic solvent phase in which the complex is sufficiently soluble.Type: GrantFiled: December 10, 1993Date of Patent: June 27, 1995Assignee: The Research Foundation of State University of New YorkInventors: Cynthia Burrows, Thomas R. Wagler, Heungsik Yoon
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Patent number: 5344945Abstract: Process for the production of epichlorohydrin in which the chloroaliphatic impurities formed at the hypochlorination of allyl chloride to dichloropropanols are removed from the crude aqueous solution of dichloropropanols before dehydrochlorination, by extraction with a recycled organic solvent which is rich in 1,2,3-trichloropropane.Type: GrantFiled: March 12, 1993Date of Patent: September 6, 1994Assignee: Solvay (Societe Anonyme)Inventor: Frans Grunchard
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Patent number: 5245048Abstract: A process for the production of a glycidyl ether of an alcohol, comprising reacting an alcohol with epichlorohydrin, in substantially the stoichiometric proportions required to produce the 1:1 adduct, in the presence, as catalyst, of a salt of perchloric acid or trifluoromethane sulphonic acid with a metal of Group IIIA of the Periodic Table of Elements (according to the IUPAC 1970 convention); and then dehydrochlorinating the product so obtained.Type: GrantFiled: December 11, 1991Date of Patent: September 14, 1993Assignee: Ciba-Geigy CorporationInventors: William M. Rolfe, Michael R. Thoseby
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Patent number: 5245057Abstract: A continuous horizontal reactor system and process for employing such a system. In one embodiment, a reactor system having a cylindrical multi-compartment vessel, the compartments intercommunicating via a common overhead space or separated spaces from which vapor with reaction product or by-products may be removed, and from which liquid effluent with reaction products or by-products may be removed and reactants and catalyst flowable into each compartment and agitators in each compartment. Such a reactor system for producing liquid epoxy resins. Processes using such a reactor to produce reaction products, e.g. liquid epoxy resins.Type: GrantFiled: November 4, 1992Date of Patent: September 14, 1993Assignee: The Dow Chemical CompanyInventor: Robert P. Shirtum