Purification Or Recovery Patents (Class 568/810)
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Patent number: 9896402Abstract: The present invention provides a method for producing a reduction reaction product, wherein recovery of the reaction solvent and/or distillation is carried out after adding a nitrogen-containing compound into a reaction liquid of a reduction reaction that has been conducted using a transition metal complex. The present invention is capable of suppressing decrease in the optical purity of the reduction reaction product due to the transition metal complex used as a catalyst.Type: GrantFiled: November 4, 2011Date of Patent: February 20, 2018Assignee: TAKASAGO INTERNATIONAL CORPORATIONInventors: Hideki Nara, Yoshiki Hasegawa
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Patent number: 8889915Abstract: Systems and methods for improving crude acetone column energy efficiency and operation are provided. The method for improving crude acetone column energy efficiency and operation can include introducing a crude acetone including acetone and phenol to a fractionation column and introducing cumene, AMS, or a combination thereof to the fractionation column. The method can include fractionating the crude acetone within the fractionation column to produce an acetone containing overhead and a phenol containing bottoms. The method can also include condensing at least a portion of the acetone containing overhead indirectly with a cool heat transfer medium to provide a condensed crude acetone product and a heated heat transfer medium, wherein the heat transfer medium includes cumene.Type: GrantFiled: February 25, 2014Date of Patent: November 18, 2014Assignee: Kellogg Brown & Root LLCInventors: Truc Vu, Theodor Robert Wilks
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Publication number: 20140296582Abstract: The present invention provides a method for producing a reduction reaction product, wherein recovery of the reaction solvent and/or distillation is carried out after adding a nitrogen-containing compound into a reaction liquid of a reduction reaction that has been conducted using a transition metal complex. The present invention is capable of suppressing decrease in the optical purity of the reduction reaction product due to the transition metal complex used as a catalyst.Type: ApplicationFiled: November 4, 2011Publication date: October 2, 2014Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventors: Hideki Nara, Yoshiki Hasegawa
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Patent number: 8742179Abstract: The present invention relates to a method for producing aryl-, heteroaryl- or alkenyl-substituted unsaturated hydrocarbons, containing: reacting aryl halides, heteroaryl halides or alkenyl halides with alkynes or alkenes in the presence of a palladium catalyst to obtain a crude product, and subsequently distillatively purifying the crude product in the presence of a compound having at least one NC?S group.Type: GrantFiled: August 13, 2010Date of Patent: June 3, 2014Assignee: Nippon Soda Co., Ltd.Inventors: Toshiaki Nishizawa, Makoto Funabora
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Patent number: 8212085Abstract: There is disclosed a purification method of an optically active 1-(2-trifluoromethylphenyl)ethanol represented by the formula [1], which includes recrystallizing the optically active 1-(2-trifluoromethylphenyl)ethanol from an aliphatic hydrocarbon solvent where * denotes an asymmetric carbon. This method makes it possible to improve the optical purity of the ethanol significantly.Type: GrantFiled: January 20, 2009Date of Patent: July 3, 2012Assignee: Central Glass Company, LimitedInventors: Akihiro Ishii, Hideyuki Tsuruta
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Patent number: 8134032Abstract: Crystalline modifications of (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol, pharmaceutical compositions which contain these modifications, and the use thereof to treat pain or other conditions.Type: GrantFiled: December 5, 2008Date of Patent: March 13, 2012Assignee: Gruenenthal GmbHInventor: Michael Gruss
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Patent number: 8013191Abstract: A two-step method of crude phenol treatment from impurities, wherein a first step comprises oxidizing hydroxyacetone and aldehydes impurities, in phenol medium by air oxygen with the use of a heterogeneous catalyst which contains transition metals, and a second step comprises treating the unoxidized impurities with the use of a heterogeneous acidic catalyst. The separation of treatment by-products compounds produced during said phenol treatment may then be carried out by a conventional fractionation, distillation, or equivalent method, to produce highly purified product phenol.Type: GrantFiled: July 19, 2006Date of Patent: September 6, 2011Assignee: Illa International, LLCInventors: Vladimir Mikhailovitch Zakoshansky, Irina Ivanovna Vassilieva, Yuri Nikolaevich Koshelev, Yuri Ivanovitch Malov
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Publication number: 20110184169Abstract: The present invention discloses a process for isolating enantiomer components from a mixture of enantiomers through particle-size-controlled crystallization, comprising the steps of: (a) forming a solution of a mixture of enantiomers (R) and (S) in a solvent in the absence of any further additives or agents; (b) seeding the solution of step (a) simultaneously or consecutively with seed crystals of enantiomer (R) and with seed crystals of enantiomer (S), wherein the seed crystals of enantiomer (R) differ in size and/or in quantity from the seed crystals of enantiomer (S) to allow separation of the crystals composed of a mixture enriched with enantiomer (R) from the crystals composed of a mixture enriched with enantiomer (S); (c) inducing simultaneous crystallization of enantiomer (R) and enantiomer (S); and (d) isolating crystals composed of a mixture enriched with enantiomer (R) from crystals composed of a mixture enriched with enantiomer (S) through size separation of the crystals, preferably through sievingType: ApplicationFiled: July 28, 2009Publication date: July 28, 2011Inventors: David Maillard, Guntram Koller, Ewgenij Wakaresko, Sabine Gottburg-Reininger
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Patent number: 7977516Abstract: Processes for the separation and purification of polyphenol trans-resveratrol and/or anthraquinone emodin from Polygonum cuspidatum and/or Rumex acetosa, by means of solvent selective extraction. Products obtained by this process present high level of purity; being therefore useful in the preparation of nutraceutical (pharmaceutical and/or food) compositions with antioxidant, anti-inflammatory, antiviral, cardioprotective, neuroprotective, chemoprotective activities, besides protecting against infections and ischemia, treating type 1 and 2 diabetes, reducing obesity and preventing aging. Useful phytomedicines for the same therapeutic activity and prepared from the roots and/or rhizomes of Rumex acetosa or from their fractions are also provided.Type: GrantFiled: January 30, 2008Date of Patent: July 12, 2011Assignee: Uniao Brasileira de Educacao e Assistencia-Sponsor of da PUCSInventor: André Arigony Souto
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Publication number: 20110054223Abstract: There is disclosed a purification method of an optically active 1-(2-trifluoromethylphenyl)ethanol represented by the formula [1], which includes recrystallizing the optically active 1-(2-trifluoromethylphenyl)ethanol from an aliphatic hydrocarbon solvent where * denotes an asymmetric carbon. This method makes it possible to improve the optical purity of the ethanol significantly.Type: ApplicationFiled: January 20, 2009Publication date: March 3, 2011Inventors: Akihiro Ishii, Hideyuki Tsuruta
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Patent number: 7795478Abstract: A fluorine-containing benzaldehyde is reacted with an alkyl Grignard reagent to convert it to a magnesium alkoxide of racemic, fluorine-containing, benzyl alcohol, and subsequently the magnesium alkoxide is reacted with phthalic anhydride to obtain a phthalate half ester of racemic, fluorine-containing, benzyl alcohol, and the half ester is optically resolved by optically active 1-phenylethylamine, and then the ester group is hydrolyzed, thereby producing an optically active, fluorine-containing, benzyl alcohol.Type: GrantFiled: October 4, 2006Date of Patent: September 14, 2010Assignee: Central Glass Company, LimitedInventors: Akihiro Ishii, Koji Ueda, Manabu Yasumoto
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Patent number: 7781623Abstract: A process for the production of a color-stable composition containing cardanol, including (a) subjecting crude, cashew nutshell liquid to distillation to obtain a distillate; (b) reacting the distillate with acetic anhydride to obtain a reaction mixture; and (c) subjecting the reaction mixture to fractional distillation is provided. A method for the production of color-stable phenalkamines, including (a) subjecting crude, cashew nutshell liquid to distillation to obtain a distillate; (b) reacting the distillate with acetic anhydride to obtain a reaction mixture; (c) subjecting the reaction mixture to fractional distillation to obtain a cardanol-containing fractional distillate; and (d) reacting the fractional distillate with an aliphatic amine and formaldehyde to form a color-stable phenalkamine is also provided.Type: GrantFiled: April 5, 2006Date of Patent: August 24, 2010Assignee: Cognis IP Management GmbHInventors: Setsuo Sato, Wanderson Bueno De Almeida, Ramiro Carielo Bueno, Alexssander Shigueru Araujo
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Publication number: 20100160690Abstract: Hydroxytyrosol is extracted from olives and/or from the solid residues of olives after the extraction of olive oil, by carrying out acid hydrolysis at a temperature within the range of 110° C. to 140° C. and at a pH within the range of 1.0 to 6.0, and by purifying the obtained solution on a column containing acid activated anion exchange resins, and a column containing an adsorbent non-ionic resin; both columns being eluted with water to recover the hydroxytyrosol.Type: ApplicationFiled: January 25, 2008Publication date: June 24, 2010Applicant: Probelte Pharma S.AInventors: Jose A. Lopez Mas, Sergio A. Streitenberger, Marcos Penalver Mellado, Pedro Martinez Ortiz
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Publication number: 20100081849Abstract: The invention provides a reaction system comprising: a first reaction promoter capable of converting a first substrate into a first substance; and a plurality of microcapsules, each of said microcapsules comprising a second reaction promoter encapsulated within an encapsulant, said second reaction promoter being capable of converting a second substrate into a second substance. The second substrate is capable of passing through the encapsulant to contact the second reaction promoter and the second substance is capable of passing out of the microcapsules through the encapsulant.Type: ApplicationFiled: August 23, 2007Publication date: April 1, 2010Inventors: Anthony Frederick Masters, Alessandro Fois, Thomas Maschmeyer
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Poly(carbonate-co-urea) copolymers and melt transesterification method of preparing these copolymers
Patent number: 7666977Abstract: Disclosed herein is a process to prepare a poly(carbonate-co-urea) copolymer comprising reacting in the melt: (a) a dihydroxy reaction component comprising a dihydroxy compound, (b) a diaryl carbonate reaction component comprising a diaryl carbonate, (c) a urea reaction component comprising a urea compound in the presence of (d) a transesterification catalyst during at least part of the reaction and removing a phenolic byproduct to produce a poly(carbonate-co-urea) copolymer, wherein the urea and dihydroxy compounds are reacted in a molar ratio: (total moles of urea compound)/((total moles of urea compound)+(total moles of dihydroxy compound)) of less than or equal to 0.5.Type: GrantFiled: May 3, 2007Date of Patent: February 23, 2010Assignee: SABIC Innovative Plastics IP B.V.Inventors: Jan Henk Kamps, Edward Kung, Jan-Pleun Lens -
Publication number: 20090030235Abstract: The present invention relates to a method for fractionating stereoisomeric compounds which have at least one alcohol and/or amino group.Type: ApplicationFiled: September 29, 2006Publication date: January 29, 2009Applicant: BASF SEInventors: Christoph Jakel, Rocco Paciello, Nawid Kashani-Shirazi, Gerd Kaibel
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Patent number: 7244772Abstract: We describe a process for the preparation of polyurethane polyol from CARDANOL 3-(8pentadecenyl)phenol, derived from cashew nut shell liquid (CNSL), a renewable resource material. The polyol is made by oxidation with peroxy acid generated in situ to give epoxidised CARDANOL 3-(8-pentadecenyl)phenol and the epoxy derivative is converted to the polyol in the presence of the organic acid. The cardanol-based polyol may be reacted with isocyanate to form polyurethane. Alternatively blowing agents are included with the cardanol-based polyol before it is reacted with the isocyanate. These polyols are especially suitable for making rigid foams of very low density and high compressive strength.Type: GrantFiled: June 30, 2004Date of Patent: July 17, 2007Assignee: Council of Scientific and Industrial ResearchInventors: Suresh Kattimuttathu Ittara, Kishanprasad Vadi Sarangapani
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Publication number: 20040176647Abstract: The hydrothermal treatment is based on placing the crude residual plant material in contact with hot water in a closed reactor, comprising the following steps:Type: ApplicationFiled: March 16, 2004Publication date: September 9, 2004Applicant: Centro de Investigaciones EnergeticasInventors: Mercedes Ballesteros Perdices, Maria Jose Negro Alvarez, Paloma Manzanares Secades, Ignacio Ballesteros Perdices, Jose Miguel Oliva Dominguez
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Publication number: 20040158106Abstract: A method of purifying a phenol stream that contains a concentration of a contaminating compound is provided. The phenol stream is treated or purified by contacting the stream, under suitable process conditions, with a treatment catalyst that has a low silica content but comprises alumina and a Group VIA metal.Type: ApplicationFiled: January 21, 2004Publication date: August 12, 2004Inventor: Larry Wayne Payne
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Publication number: 20040158105Abstract: A method of manufacturing a phenol product having a reduced concentration of a contaminating reaction by-product. The method includes contacting a phenol stream, having a concentration of the contaminating by-product, by contacting the phenol stream with an acidic catalyst under suitable purification reaction conditions. Also included is a composition comprising a sec-butyl benzene derived phenol product that has been purified by the removal of certain undesirable reaction by-products.Type: ApplicationFiled: January 21, 2004Publication date: August 12, 2004Inventor: Larry Wayne Payne
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Patent number: 6660884Abstract: The present invention relates to compounds useful as catalysts in asymmetric synthesis of chiral compounds, methods for the synthesis of said catalysts, and methods for synthesizing chiral compounds with high enantioselectivity.Type: GrantFiled: March 14, 2003Date of Patent: December 9, 2003Assignee: The Trustees of the University of PennsylvaniaInventor: Patrick J. Walsh
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Patent number: 6586639Abstract: This invention discloses a substance which is a betaine ester of a functional alcohol that has an amido bond in its molecule and releases the functional alcohol.Type: GrantFiled: July 2, 2002Date of Patent: July 1, 2003Assignee: Kao CorporationInventors: Koichi Murayama, Shigeyoshi Tanaka, Atsushi Katayama, Ryoichi Hirayama, Takami Gema
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Publication number: 20030108651Abstract: The invention provides olive-derived hydroxytyrosol. According to one aspect of the invention, vegetation water is collected from olives. Acid is added to stabilize the vegetation water and prevent fermentation. The mixture is incubated to allow oleuropein to convert to hydroxytyrosol, and then fractionated to separate hydroxytyrosol from other components. The hydroxytyrosol is useful as a therapeutic and anti-oxidant for a variety of health purposes, including for the treatment of skin damage. In addition, the hydroxytyrosol is useful as a natural anti-bacterial, anti-viral and fungicidal product for agricultural and pest control applications.Type: ApplicationFiled: July 5, 2002Publication date: June 12, 2003Inventor: Roberto Crea
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Publication number: 20030100800Abstract: A system for purifying a cumene hydroperoxide cleavage product mixture comprises a cumene hydroperoxide cleavage product mixture feed containing impurities in fluid communication with an aqueous alkaline solution feed; the cumene hydroperoxide cleavage product mixture and aqueous alkaline solution feeds are in fluid communication with a neutralization drum having an aqueous salt phase outlet; an aqueous salt phase feed containing impurities in fluid communication with a heat treatment vessel having a heat-treated aqueous salt phase outlet; and a heat-treated aqueous salt phase feed containing water-soluble derivatives of the impurities in fluid communication with the cumene hydroperoxide cleavage product mixture prior to the neutralization drum.Type: ApplicationFiled: November 29, 2001Publication date: May 29, 2003Inventors: John William Fulmer, Pramod S. Kumbhar, Marakani Venkata Ramani, Bharat Singh
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Publication number: 20030100799Abstract: A system for purifying a cumene hydroperoxide cleavage product mixture comprises a cumene hydroperoxide cleavage product mixture feed containing impurities in fluid communication with an aqueous alkaline solution feed; the cumene hydroperoxide cleavage product mixture and aqueous alkaline solution feeds in fluid communication with a neutralization drum having a aqueous salt phase outlet; a aqueous salt phase feed containing impurities in fluid communication with a decomposer reactor having an oxidized aqueous salt phase outlet; an oxidizing agent feed in fluid communication with the aqueous salt phase feed containing the impurities prior to the decomposer reactor; and an oxidized aqueous salt phase feed containing water-soluble oxidized derivatives of the impurities in fluid communication with the cumene hydroperoxide cleavage product mixture prior to the neutralization drum.Type: ApplicationFiled: November 29, 2001Publication date: May 29, 2003Inventors: Yuri Valerievich Aristovich, Valeri Yurievich Aristovich, John William Fulmer, Andrey Yurievich Sokolov, Svetlana Ananyevna Ulyanova, Sergey Nikolaevich Voyakin
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Patent number: 6491795Abstract: High-purity benzyl benzoate is recovered by distilling the residue remaining after removal of unreacted toluene and benzoic acid from a reaction mixture produced by the oxidation of toluene by molecular oxygen in the presence of a metal catalyst thereby separating a fraction of benzyl benzoate containing 80 wt % or more benzyl benzoate, 10 wt % or less benzoic acid and 10 wt % or less fluorenone, and purifying the fraction of benzyl benzoate by crystallization such as recrystallization. According to this process, it is possible to recover high-purity benzyl benzoate by a simple operation at low cost from the by-product formed in the manufacture of benzoic acid.Type: GrantFiled: February 8, 2001Date of Patent: December 10, 2002Assignee: Nippon Steel Chemical Co., Ltd.Inventors: Noboru Daitou, Shingo Ueda, Ryouji Akamine, Kazuyoshi Horibe, Katsuhiko Sakura
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Patent number: 6437176Abstract: An aromatic carboxylic acid, aromatic aldehyde, and aromatic alcohol are simultaneously and efficiently prepared by liquid phase oxidizing an aromatic compound represented by formula (I) with a gas containing molecular oxygen, in a presence of a catalyst comprising transition metal compound, tertiary amine and bromide compound:Type: GrantFiled: March 19, 2001Date of Patent: August 20, 2002Assignee: Toray Industries, Inc.Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura
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Patent number: 6423290Abstract: An organic solvent is separated from a waste stream comprising hydrofluoric acid, an organic solvent and etchant contaminants. The process comprises separating the hydrofluoric acid by subjecting the waste stream to at least one of the following processes: ion exchange; extraction of the hydrofluoric acid; electrophoresis; converting the hydrofluoric acid to an insoluble salt; to thereby obtain a first composition containing the hydrofluoric acid and a second stream containing the organic solvent and being substantially free of the hydrofluoric acid; and then distilling the second stream to recover the organic solvent free of the etching contaminants.Type: GrantFiled: May 31, 2000Date of Patent: July 23, 2002Assignee: International Business Machines CorporationInventors: Anilkumar C. Bhatt, Jerome J. Wagner
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Patent number: 6361983Abstract: The invention concerns a process for the isolation of polyols, such as 1,3-propanediol, from a fermentation broth. Specifically, the invention discloses a process of adding base to the fermentation broth to raise the pH to a suitable level for reduction of impurity formation during isolation of the polyol.Type: GrantFiled: September 27, 2000Date of Patent: March 26, 2002Assignee: E. I. du Pont de Nemours and CompanyInventor: Tyler T. Ames
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Patent number: 6326521Abstract: Process for the preparation of benzyl alcohol via hydrolysis of a benzyl ester with water in the liquid phase, the hydrolysis being carried out in the absence of a strong acid and a base at a temperature between 40° C. and 320° C. The benzyl ester to be hydrolyzed can be chosen from the group comprising benzyl formiate, benzyl propionate, benzyl acetate and benzyl benzoate. A weak acid may optionally be added to the reaction mixture to be hydrolyzed. After the hydrolysis the reaction mixture is preferably cooled to a temperature between 80° C. and 180° C. so that a phase separation takes place. Both the organic phase and the aqueous phase can be upgraded. As such, benzyl alcohol can be obtained with a high overall yield and a purity of more than 98%.Type: GrantFiled: December 18, 1998Date of Patent: December 4, 2001Assignee: DSM N.V.Inventors: Jacob Van Soolingen, Alexander P. M. Vrinzen, Christiaan J. C. Stoelwinder, Abram Peet, Hendricus J. Rozie, Otto G. Plantema
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Patent number: 6218581Abstract: The present invention relates to a process of producing optically active alcohol having high optical purity by performing an enzyme conversion reaction on a raw material serving as the substrate, examples of which include racemic alcohol, ketone and the acylated form of a racemic alcohol, followed by hydrolysis as necessary, using as an optical separation catalyst a immobilized water-soluble protein extracted from inexpensive and safe grains or beans in order to solve the problems of the reaction process consisting of low yield due to the occurrence of side reactions, detrimental effects on the ecosystem and their accompanying cost burden, the need for aseptic procedures and the extended amount of time of subculturing, all of which are problems associated with production processes of optically active alcohols of the prior art that use microorganisms, microorganism enzymes, animal tissue enzymes and cultured plant cells.Type: GrantFiled: August 6, 1999Date of Patent: April 17, 2001Assignee: Sanyo Shokuhin Co., Ltd.Inventor: Hiroyuki Nagaoka
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Patent number: 6207867Abstract: A method for purifying &bgr;-phenylethyl alcohol, comprising an extractive distillation process in which crude &bgr;-phenylethyl alcohol is extractive-distilled using an extraction solvent (A), and an extracting process in which the extraction solvent (A) after use in the extractive distillation process is extracted using other extraction solvent (B).Type: GrantFiled: April 5, 2000Date of Patent: March 27, 2001Assignee: Sumitomo Chemical Company, LimitedInventors: Kazuhiko Kamaya, Yoshimitsu Onodera
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Patent number: 6197994Abstract: The present invention relates to silica gel supported bis-cinchona alkaloid compounds of the formula: wherein Q is dihydroquininyl or dihydroquinindinyl; X is a compound having 4 carbon atoms; and R is methoxy, ethoxy or methyl; and methods of preparation and use thereof. The silica gel supported bis-cinchona alkaloid derivatives of this invention are useful re-useable catalysts for preparing vicinal diols by asymmetric dihydroxylation of olefins.Type: GrantFiled: May 4, 1999Date of Patent: March 6, 2001Assignee: Korea Institute of Science and TechnologyInventors: Choong Eui Song, Jung Woon Yang
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Patent number: 6187965Abstract: A method of recovering benzyl alcohol, gamma butyrolactone, or propylene carbonate from an impure effluent stream of an industrial process is provided. The effluent waste stream contains greater than about 10 percent by weight of monomeric units that are reacted to form larger oligomers and polymers. The first step in the recovery process involves polymerizing the monomeric units present in the effluent waste stream under conditions effective to reduce the concentration of monomeric units in the waste stream to less than about 10 weight percent. The waste stream then is fed to a first separation stage where it is separated into (i) a gaseous stream of water, soluble gases, and volatile contaminants and (ii) a suspension comprising the high boiling solvent, semi-volatile materials, and non-volatile contaminants and materials. Then the dewatered, low vapor pressure, high boiling solvent-containing suspension is either distilled or evaporated to separate the high boiling solvent from non-volatile materials.Type: GrantFiled: November 6, 1998Date of Patent: February 13, 2001Assignee: International Business Machines CorporationInventors: Anilkumar C. Bhatt, Jerome J. Wagner
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Patent number: 6166260Abstract: The present invention relates to a tandem process of reduction and host-guest complexation using metal-hydride complexes to reduce chemical entities bearing carbonyl groups or their equivalents, and host-guest complexation to achieve improved optical resolution of the reduction product. In the complexation step, the reduction product is optically resolved via inclusion into the crystalline complex where it resides as guest and another complex component acts as host. Additional crystallization stages are performed if further improvements in the enantiomeric excess is desired.Type: GrantFiled: August 6, 1999Date of Patent: December 26, 2000Assignee: Zeeland Chemicals, Inc.Inventor: Glenn L. Heise
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Patent number: 5994597Abstract: A method of recovering solvents from an impure effluent stream of an industrial process. The effluent waste stream contains less than about 10 percent by weight of monomeric units that are reacted to form larger oligomers and polymers. The waste stream contains dissolved polymers, polymeric particles, and the hydrolysis, oxidation and/or other decomposition products of one of the solvents. In one embodiment, the first step involves filtering particulate matter from the waste stream. In another embodiment, the filtering step is omitted. The filtered or unfiltered waste stream is fed to a first separation stage for separation into (i) a gaseous stream of water, soluble gases, and volatile contaminants and (ii) a suspension comprising the solvent, water, semi-volatile and non-volatile contaminants, and photoresist products.Type: GrantFiled: November 6, 1998Date of Patent: November 30, 1999Assignee: International Business Machines CorporationInventors: Anilkumar C. Bhatt, Jerome J. Wagner
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Patent number: 5986095Abstract: A process is described for preparing a compound of the formula or the S-enantiomer thereof,wherein:R is alkyl, aryl, cycloalkyl, aralkyl, or cycloalkylalkyl,R.sup.1 is halogen;R.sup.2 is halogen, alkyl, cycloalkyl, aryl or ##STR1## wherein the process comprises treating the associated racemic alcohol with an acylatingagent ##STR2## (wherein L is a leaving group) and an enzyme or microorganism capable of enantioselective acylation. This process may also be used to isolate the unreacted R- or S-alcohol. The acylated product may be enantioselectively hydrolyzed with a lipase or lipase-supplying microorganism to the S- or R-alcohol. Compounds prepared by this invention are useful antipsychotic agents or useful intermediates therefor.Type: GrantFiled: January 6, 1992Date of Patent: November 16, 1999Assignee: E.R. Squibb & Sons, Inc.Inventors: Ronald L. Hanson, Ramesh N. Patel, Laszlo J. Szarka
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Patent number: 5981807Abstract: A process for producing optically active 2-halo-1-(substituted phenyl)ethanol of a formula (Ia) or optically active styrene oxide of a formula (Ib). The process comprises the steps of reacting a compound of a formula (II) with phthalic anhydride to give a compound of a formula (III), performing optical resolution on the resulting compound using an optically active organic amine as a resolving agent, and finally performing hydrolysis or alcoholysis on the optically resolved compound (Ia) or (Ib). The scheme of the above process is: wherein X represents a halogen atom, Y represents a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 haloalkyl group or a C.sub.1 -C.sub.6 haloalkoxy group, Z represents a hydrogen atom, a halogen atom or a C.sub.1 -C.sub.6 alkyl group, n is 0 or an integer of 1 to 3 and m is 0 or an integer of 1 to 2. The resulting optically active compounds are useful as an intermediate for medicines.Type: GrantFiled: October 27, 1997Date of Patent: November 9, 1999Assignee: Nihon Nohyaku Co., Ltd.Inventors: Hiroki Kodama, Takuya Motokawa, Hiroshi Yamaguchi, Masanori Yoshida
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Patent number: 5965780Abstract: The invention relates to a method for extracting 2-phenylethanol, in which the 2-phenylethanol is extracted from the distillation residues obtained during the production of alcohol.Type: GrantFiled: July 31, 1997Date of Patent: October 12, 1999Assignee: Pernod RicardInventors: Jean-Pierre Savina, Daniele Kohler, Pascal Brunerie
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Patent number: 5919991Abstract: A method for isolating phenethyl alcohol in high yield is provided by fermenting L-phenylalanine within a fermentation bath to provide phenethyl alcohol. The fermented phenethyl alcohol is then contacted with an ion-exchange resin to extract the phenethyl alcohol.Type: GrantFiled: July 3, 1996Date of Patent: July 6, 1999Inventor: Ven Subbiah
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Patent number: 5888400Abstract: A process for preparing low-salt preparations of condensation products based onA) sulphonated aromatics,B) aldehydes and/or ketones and optionallyC) one or more compounds selected from the group consisting of nonsulphonated aromatics, urea and urea derivatives,characterized in that inorganic acid present after the condensation is separated off in whole or in part from the condensation product, optionally in the form of its salts after neutralization, until the inorganic salt content is less than 10% by weight, relative to the preparation, leads to preparations which are outstandingly suitable as tanning agents, dispersants and liquefiers.Type: GrantFiled: June 20, 1997Date of Patent: March 30, 1999Assignee: Bayer AktiengesellschaftInventors: Edzard Tholema, Wolfgang Zarges, Harro Traubel
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Patent number: 5756862Abstract: A process for producing optically active 2-halo-1-(substituted phenyl)ethanol of a formula (Ia) or optically active styrene oxide of a formula (Ib). The process comprises the steps of reacting a compound of a formula (II) with phthalic anhydride to give a compound of a formula (III), performing optical resolution on the resulting compound using an optically active organic amine as a resolving agent, and finally performing hydrolysis or alcoholysis on the optically resolved compound (Ia) or (Ib). The scheme of the above process is: ##STR1## wherein X represents a halogen atom, Y represents a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 haloalkyl group or a C.sub.1 -C.sub.6 haloalkoxy group, Z represents a hydrogen atom, a halogen atom or a C.sub.1 -C.sub.6 alkyl group, n is 0 or an integer of 1 to 3 and m is 0 or an integer of 1 to 2. The resulting optically active compounds are useful as an intermediate for medicines.Type: GrantFiled: August 19, 1996Date of Patent: May 26, 1998Assignee: Nihon Nohyaku Co., Ltd.Inventors: Hiroki Kodama, Takuya Motokawa, Hiroshi Yamaguchi, Masanori Yoshida
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Patent number: 5714642Abstract: Immixture of stereoisomeric alcohols is resolved by selectively enzymatically acylating one of the stereoisomers thereof, in the presence of a catalytically effective amount of a hydrolase, for example a lipase, esterase or acylase, in a biphasic hydroorganic reaction medium, and thence separating the alcohol stereoisomer from the ester stereoisomer thus formed.Type: GrantFiled: September 5, 1995Date of Patent: February 3, 1998Assignee: Rhone-Poulenc ChimieInventors: Christophe Didion, Dominique Petre
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Patent number: 5679766Abstract: The invention is for a process of removal of dissolved cation contaminants from a resin solution. The process of the invention involves providing a chelating ion exchange resin modified by treatment with an acid and contact of said solution with said modified exchange resin for a time sufficient to remove ionic metal impurities. The invention is useful for removal of ionic contaminants from resin solutions used in the preparation of photoresists.Type: GrantFiled: December 7, 1993Date of Patent: October 21, 1997Assignee: Shipley Company, L.L.C.Inventor: Anthony Zampini
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Patent number: 5600027Abstract: A process for producing an optically active alcohol having a phenyl group is disclosed, comprising the step of carrying out interesterification between (a) a monoester between a racemic alcohol having a phenyl group and a fatty acid or a diester between a racemic alcohol having a phenyl group and a dibasic acid and (b) an optically inactive non-racemic alcohol having 16 or more carbon atoms in the presence of heat-resistant lipase and in the absence of a solvent under a substantially water-free condition at a temperature of not lower than 81.degree. C. under atmospheric pressure or reduced pressure and the step of separating an optically active alcohol having a phenyl group rich in either one of R- and S-forms from the reaction mixture. Use of heat-resistant lipase makes it possible to use high-melting point materials without using any solvent therefor and to perform interesterification at a high temperature thereby completing the reaction in a reduced time.Type: GrantFiled: September 15, 1995Date of Patent: February 4, 1997Assignee: The Nisshin Oil Mills, Ltd.Inventors: Junko Suzuki, Satoshi Negishi, Seiichi Shirasawa, Yukie Masuda
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Patent number: 5538599Abstract: A process is provided whereby phenol is separated from 1-phenyl ethanol, acetophenone or mixtures by extractive distillation with sulfolane as extractive distillation agent which decreases phenol volatility relative to 1-phenyl ethanol and acetophenone.Type: GrantFiled: June 5, 1995Date of Patent: July 23, 1996Assignee: ARCO Chemical Technology, L.P.Inventors: Tim T. Wong, Stephen H. Harris, Thomas S. Zak, Te Chang
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Patent number: 5449841Abstract: A process for reducing the level of metal ions and/or metal compounds in a polyoxyalkylene monool or polyol having a number average molecular weight of above 500-25000 by bringing the monool or polyol into contact with an extracting compound which is a polyol or a polyol mixture having a number average molecular weight of at most 500 and being immiscible with the polyoxyalkylene monool or polyol, mixing the extracting compound and the polyoxyalkylene monool or polyol, allowing the extracting compound and the polyoxyalkylene monool or polyol to separate and removing the extracting compound.Type: GrantFiled: October 12, 1994Date of Patent: September 12, 1995Assignee: Imperial Chemical Industries PLCInventor: Patrick M. G. Goegebeur
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Patent number: RE40912Abstract: A method of isolating, purifying and recrystallizing substantially pure lutein, preferably from saponified marigold oleoresin in its pure free form, apart from chemical impurities and other carotenoids. Lutein may be used as an analytical standard or in cancer prevention trials and as a safe and effective color additive for human food.Type: GrantFiled: June 10, 2005Date of Patent: September 8, 2009Assignee: The Catholic University of AmericaInventor: Frederick Khachik
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Patent number: RE40931Abstract: A method of isolating, purifying and recrystallizing substantially pure lutein, preferably from saponified marigold oleoresin in its pure free form, apart from chemical impurities and other carotenoids. Lutein may be used as an analytical standard or in cancer prevention trials and as a safe and effective color additive for human food.Type: GrantFiled: January 10, 2006Date of Patent: October 6, 2009Assignee: The Catholic University of AmericaInventor: Frederick Khachik
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Patent number: RE40938Abstract: A method of isolating, purifying and recrystallizing substantially pure lutein, preferably from saponified marigold oleoresin in its pure free form, apart from chemical impurities and other carotenoids. Lutein may be used as an analytical standard or in cancer prevention trials and as a safe and effective color additive for human food.Type: GrantFiled: February 5, 2007Date of Patent: October 13, 2009Assignee: The Catholic University of AmericaInventor: Frederick Khachik