Acyclic Patents (Class 435/157)
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Patent number: 5866381Abstract: Described is a microbiological method for producing C.sub.9, C.sub.11 and C.sub.13 alkanols defined according to the structures: ##STR1## wherein R.sub.1 is methyl or n-propyl using ketones defined according to the generic structure: ##STR2## as a substrate and using the microorganism: Pseudomonas cepacia ATCC 55792or mutants thereof.Type: GrantFiled: April 23, 1998Date of Patent: February 2, 1999Assignee: International Flavors & Fragrances Inc.Inventors: Mohamad I. Farbood, Laura E. Kizer, Lynda B. McLean, Mark A. Sprecker
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Patent number: 5866382Abstract: This invention relates to recombinant-DNA-technology. Specifically, this invention relates to new recombinant yeast strains transformed with xylose reductase and/or xylitol dehydrogenase enzyme genes. A yeast strain transformed with the xylose reductase gene is capable of reducing xylose to xylitol and consequently of producing xylitol in vivo. If both of these genes are transformed into a yeast strain, the resultant strain is capable of producing ethanol on xylose containing medium during fermentation. Further, the said new yeast strains are capable of expressing the said two enzymes. Xylose reductase produced by these strains can be used in an enzymatic process for the production of xylitol in vitro.Type: GrantFiled: November 3, 1994Date of Patent: February 2, 1999Assignee: Xyrofin OyInventors: Johan Hallborn, Merja Penttila, Heikki Ojamo, Mats Walfridsson, Ulla Airaksinen, Sirkka Keranen, Barbel Hahn-Hagerdal
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Patent number: 5846793Abstract: A process for preparing optically active (R)-3-chloro-1,2-propanediol, which comprises subjecting (R,S)-3-chloro-1,2-propanediol to the reaction of a microorganism belonging to genus Serratia in a reaction mixture, and then collecting the residual (R)-3-chloro-1,2-propanediol. According to the process of the present invention, (R)-3-chloro-1,2-propanediol can be efficiently prepared starting from low cost (R,S)-3-chloro-1,2-propanediol.Type: GrantFiled: December 27, 1990Date of Patent: December 8, 1998Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Hideyuki Takahashi, Satoru Tsuda, Yoshio Nakamura, Masahiro Ogura, Tadayoshi Shiraishi, Yoshio Shimada, Kiyoshi Watanabe
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Patent number: 5840553Abstract: A novel glycerol derivative, a process for preparing the same, and a process for preparing a triazole derivative. An optically active 2-arylglycerol derivative which is novel and useful as a synthetic intermediate of medicament is provided, and furthermore, (R)-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazole-1-yl)-propane-1,2-diol, which is useful as an antifungal agent, is prepared.Type: GrantFiled: March 11, 1997Date of Patent: November 24, 1998Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Yoshihiko Yasohara, Kenji Miyamoto, Noriyuki Kizaki, Shigeru Kawano, Junzo Hasegawa
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Patent number: 5763236Abstract: The present invention provides a novel secondary alcohol dehydrogenase useful for the synthesis of optically active alcohol and DNA encoding said enzyme. A microorganism belonging to genus Candida was found to produce a novel secondary alcohol dehydrogenase with a high stereochemical specificity. Using said enzyme, optically active alcohols were prepared, and by cloning of DNA encoding said enzyme, the base sequence of said DNA was determined. By providing a novel secondary alcohol dehydrogenase with a high stereochemical specificity and the gene encoding said enzyme, an efficient production of optically active alcohols became possible.Type: GrantFiled: September 12, 1996Date of Patent: June 9, 1998Assignee: Daicel Chemical Industries Ltd.Inventors: Tomoko Kojima, Hiroaki Yamamoto, Naoki Kawada, Akinobu Matsuyama
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Patent number: 5753474Abstract: The instant invention describes a process for the manufacture of butanol and like volatile organic compounds by fermenting carbohydrates, mainly polysaccharide, with micro-organisms which convert carbohydrates into mainly butyric acid and other acids. The acids are subsequently transferred to the solventogenesis production stage using a different strain of bacteria which continuously produces butanol and like volatile organic compounds, via a multistage fermentation process that is stable, high yielding (weight product per unit weight carbohydrates) and productive (faster throughput). By employing one microbe (the first) in the major pathway to produce the acid of choice specifically and faster, and provide for another microbe (the second) with the unique property to convert the acid to a solvent, carbohydrates are not wasted on ancillary product. The unique advantage of the second microbe is that it has the capability of converting acids into solvents (solventogenesis).Type: GrantFiled: December 20, 1996Date of Patent: May 19, 1998Assignee: Environmental Energy, Inc.Inventor: David Edward Ramey
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Patent number: 5731177Abstract: Process for preparing S-methylmercapto and mercapto compounds comprising the step of demethylating a dimethylsulfonium compound of formula I to the corresponding S-methylmercapto compound of formula II, using a microorganism or alga which is capable of demethylating 3-dimethylsulfonium propionate (DMSP) to S-methyl-3-mercaptopropionate (MMPA), but which is incapable of further demethylating the latter compound to 3-mercaptopropionate with the same speed, or using an enzyme preparation derivable from such microorganism or alga: ##STR1## Preferably the group R denotes CH.sub.2 --CH.sub.2 --COOH (I is DMSP), CH.sub.2 --CH(NH.sub.2)--COOH (I is S-dimethyl-cystein), CH.sub.2 --Ch.sub.2 --CH (NH.sub.2) --COOH (I is S-methyl-methionine) or CH.sub.2 --COOH (I is 2-dimethylsulfonium acetate), or a salt or ester of any of these. The microorganisms are preferably marine Desulfobacterium strains, especially a Desulfobacterium autotrophicum, Desulfobacterium vacuolatum or similar strain.Type: GrantFiled: November 14, 1995Date of Patent: March 24, 1998Assignee: Quest International B.V.Inventors: Theo Adriaan Hansen, Marc Jos E. C. van der Maarel
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Patent number: 5705369Abstract: The invention relates to the prehydrolysis of lignocellulose by passing an acidic or alkaline solution through solid lignocellulosic particles with removal of soluble components as they are formed. The technique permits a less severe combination of pH, temperature and time than conventional prehydrolysis. Furthermore, greater extraction of both hemicellulose and lignin occurs simultaneously in the same reactor and under the same conditions.Type: GrantFiled: May 18, 1995Date of Patent: January 6, 1998Assignee: Midwest Research InstituteInventors: Robert W. Torget, Kiran L. Kadam, Teh-An Hsu, George P. Philippidis, Charles E. Wyman
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Patent number: 5637500Abstract: A process for preparing optically active 1-substituted-3-hydroxy-1-butene or its derivatives of formula (II) or (III) ##STR1## is disclosed. The process comprises treating an ester derivative of racemic 1-substituted-3-hydroxy-1-butene of formula (I), ##STR2## wherein R.sub.1 is a substituted or unsabstituted alkyl, aryl, alkoxy, or aryloxy group, and R.sub.2 is a hydrogen atom, halogen atom, an alkyl, aryl, alkoxy or aryloxy group, or a substituted or unsabstituted alkylsulfonyloxy, arylsulfonyloxy, alkylthio, or arylthio group. The process can produce a desired optically active alcohol or acyl-protected compound at a high yield and a high selectivity under mild conditions by the treatment of the substrate with a lipase. In particular, when R.sub.1 =methyl and R.sub.2 =halogen or phenylthio, use of Lipase AK, P-30 or K-10 gives high enantiomeric purity.Type: GrantFiled: September 26, 1994Date of Patent: June 10, 1997Assignee: Suntory LimitedInventor: Charles J. Sih
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Patent number: 5620877Abstract: An economically viable method of fermenting a mixture of sugars resulting from the acid hydrolysis of material containing cellulose and hemicellulose allows for the simultaneous fermentation of both pentose and hexose sugars. The sugar solution is mixed with a microbial organism known to produce a useful fermentation product, and the fermentation process is allowed to proceed for 3-5 days, during and after which the fermentation products are removed and purified.Type: GrantFiled: June 6, 1995Date of Patent: April 15, 1997Assignee: Arkenol, Inc.Inventors: William A. Farone, John E. Cuzens
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Patent number: 5503996Abstract: The invention relates to the prehydrolysis of lignocellulose by passing an acidic or alkaline solution through solid lignocellulosic particles with removal of soluble components as they are formed. The technique permits a less severe combination of pH, temperature and time than conventional prehydrolysis. Furthermore, greater extraction of both hemicellulose and lignin occurs simultaneously in the same reactor and under the same conditions.Type: GrantFiled: December 27, 1994Date of Patent: April 2, 1996Assignee: Midwest Research InstituteInventors: Robert W. Torget, Kiran L. Kadam, Teh-An Hsu, George P. Philippidis, Charles E. Wyman
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Patent number: 5464772Abstract: A process for producing an optically active halogen-containing alcohol having a high optical purity and represented by the following formula [I] ##STR1## wherein R.sup.1 is a halogen substituted alkyl group, R.sup.2 is a group selected from the group consisting of a substituted or unsubstituted alkyl group, alkene group, or alkyne group, and a substituted or unsubstituted phenyl group, and C having an asterisk indicates an asymmetric atom,is disclosed which process comprises subjecting a halogenated alkyl ester of a carboxylic acid represented by the following formula [II] ##STR2## wherein R.sup.1 and R.sup.2 are the same as mentioned above and R.sup.3 is a group selected from the group consisting of a substituted or unsubstituted alkyl group or alkene group, and a substituted or unsabstituted phenyl group,to asymmetric hydrolysis with an enzyme in an aqueous solution system, and the aqueous solution system may contain buffer solution and/or organic solvent.Type: GrantFiled: April 14, 1993Date of Patent: November 7, 1995Assignee: Showa Shell Sekiyu Kabushiki KaishaInventors: Katutoshi Hirose, Yoshihiro Takagi, Toshihiko Otomatsu, Yoshiichi Suzuki
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Patent number: 5445963Abstract: A process is disclosed for the separation of an enantiomerically enriched 1-tosyloxy-2-acyloxy-3-butene and an enantiomerically enriched 1-tosyloxy-2-hydroxy-3-butene from a first mixture containing both compounds. The process includes the steps of:(a) forming a solution of the mixture in an organic solvent;(b) bringing the solution formed in (a) to a temperature wherein most of the enantiomerically enriched 1-tosyloxy-2-hydroxy-3-butene precipates, leaving in solution most of the enantiomerically enriched 1-tosyloxy-2-acyloxy-3-butene; and(c) separating the precipitate formed in (b) from the solution.Type: GrantFiled: February 26, 1991Date of Patent: August 29, 1995Assignee: Eastman Chemical CompanyInventor: Neil W. Boaz
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Patent number: 5385833Abstract: The present invention provides a substantially pure culture of Pseudomonas sp. strain PED having the ATCC designation 49794. Processes for making R-configured alcohols and for transferring a hydride ion from an R-configured alcohol to the pro-R face of NAD using PED alcohol dehydrogenase isolated and purified from Pseudomonas sp. strain PED are also provided.Type: GrantFiled: February 26, 1992Date of Patent: January 31, 1995Assignee: The Scripps Research InstituteInventors: Curt W. Bradshaw, Chi-Huey Wong, Gwo-Jenn Shen
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Patent number: 5215902Abstract: A process for recovering alcohol by a continuous process employing fermentation, solvent extraction of the alcohol product, extractive distillation of the alcohol-solvent extract to provide water fraction and vacuum stripping for separation of the alcohol and regenerated solvent.The solvent is recycled. An isoparaffin is used as a solvent and this solvent can be modified with a long chain fatty acid, alcohol or fatty alcohol or long-chain esters. Alternatively, many modifiers may be used neat.Type: GrantFiled: December 7, 1990Date of Patent: June 1, 1993Assignee: Georgia Tech Research CorporationInventor: Daniel W. Tedder
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Patent number: 5212089Abstract: A process for preparation of S-(+)-3-halogeno-1,2-propanediol which comprises cultivating a bacterium, which has an ability to assimilate R-(-)-3-halogeno-1,2-propanediol and belongs to the genus Alcaligenes, or its culture broth in a medium containing racemate 3-halogeno-1,2-propanediol, and recovering S-(+)-3-halogeno-1,2-propanediol from the resulting culture broth.Type: GrantFiled: December 19, 1990Date of Patent: May 18, 1993Assignee: Daiso Co., Ltd.Inventors: Toshio Suzuki, Naoya Kasai
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Patent number: 5192672Abstract: A purified hydroxylase component of the soluble methane monooxygenase enzyme present in the bacterium Methylosinus trichosporium OB3b is found capable of oxidizing hydrocarbons under aerobic conditions in the presence of suitable reducing agents. The hydroxylase can be reduced by commercial reducing agents, such as sodium dithionite and photo- and electrochemical means when in the presence of electron transport components, such as methyl viologen and proflavin. The hydroxylase can also be activated by hydrogen peroxide in the absence of reducing agents and molecular oxygen and is capable of oxidizing hydrocarbons under aerobic and anaerobic conditions in this manner. The hydroxylase component can be obtained with high final specific activity when ferrous iron compounds and cysteine are included in the purification buffers used to extract the hydroxylase from bacterial cells.Type: GrantFiled: June 21, 1991Date of Patent: March 9, 1993Assignee: Amoco CorporationInventor: John D. Lipscomb
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Patent number: 5190870Abstract: A purified hydroxylase component of the soluble methane monooxygenase enzyme present in the bacterium Methylosinus trichosporium OB3b is found capable of oxidizing hydrocarbons under aerobic conditions in the presence of suitable reducing agents. The hydroxylase can be reduced by commercial reducing agents, such as sodium dithionite and photo- and electrochemical means when in the presence of electron transport components, such as methyl viologen and proflavin. The hydroxylase component can be obtained with high final specific activity when ferrous iron compounds and cysteine are included in the purification buffers used to extract the hydroxylase from bacterial cells.Type: GrantFiled: October 8, 1990Date of Patent: March 2, 1993Assignee: Amoco CorporationInventors: John D. Lipscomb, Brian G. Fox
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Patent number: 5177007Abstract: A process for producing optically active R-(+)-2,3-dichloro-1-propanol, which comprises cultivating an S-(-)-2,3-dichloro-1-propanol-assimilating strain belonging to the genus Alcaligenes in a culture medium containing racemate 2,3-dichloro-1-propanol, and recovering optical isomer R-(+)-2,3-dichloro-1-propanol from the culture broth and a pure culture of an S-(+)-dichloro-1-propanol-assimilating strain belonging to the genus Alcaligenes.Type: GrantFiled: December 7, 1990Date of Patent: January 5, 1993Assignee: Daiso Co., Ltd.Inventor: Naoya Kasai
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Patent number: 5166061Abstract: A process for the production of a 4-halo-3-hydroxybutyronitrile which comprises reacting a 1,3-dihalo-2-propanol with a dehalogenating enzyme originating from a Corynebacterium or a Microbacterium in the presence of an alkali cyanide to thereby convert the 1,3-dihalo-2-propanol into the 4-halo-3-hydroyxbutyronitrile and collecting the product thus formed is disclosed. According to this process, a 4-halo-3-hydroxybutyronitrile which is highly useful in the syntheses of various medicines and physiologically active substances can be easily and efficiently produced from an inexpensive starting material.Type: GrantFiled: July 20, 1990Date of Patent: November 24, 1992Assignee: Nitto Chemical Industry Co. Ltd.Inventors: Tetsuji Nakamura, Fujio Yu, Ichiro Watanabe
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Patent number: 5155030Abstract: A process for preparing an optically active (R)-(-)-3-halo-1,2-propanediol comprising reacting an epihalohydrin with an epihalohydrin hydratase originating from a microorganism. For example, the microorganism belongs to the genus Corynebacterium or the genus Microbacterium. Epihalohydrins which can be used include epichlorohydrin and epibromohydrin. The reaction can be carried out at a temperature of from 5.degree. to 50.degree. C. and a pH of from 4 to 10.Type: GrantFiled: April 19, 1990Date of Patent: October 13, 1992Assignee: Nitto Chemical Industry Co., Ltd.Inventors: Tetsuji Nakamura, Ichiro Watanabe
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Patent number: 5126267Abstract: A process is disclosed for the isolation of an enantiomerically enriched alcohol from a first mixture of an enantiomerically enriched alcohol and an enantiomerically enriched ester. The process includes the steps of:(a) contacting the mixture with a reagent capable of reacting with the hydroxy function of the alcohol, without the loss of optical purity, so as to produce a second mixture containing a base stable derivative of the enantiomerically enriched alcohol and the unreacted ester;(b) contacting the second mixture with a base capable of reacting with the ester so as to produce a third mixture containing a compound more volatile than the base stable derivative of the alcohol;(c) removing the volatile compound from the third mixture; and(d) converting the base stable derivative of the alcohol back to the enantiomerically enriched alcohol, without the loss of optical purity.Type: GrantFiled: February 26, 1991Date of Patent: June 30, 1992Assignee: Eastman Kodak CompanyInventor: Neil W. Boaz
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Patent number: 5126268Abstract: A process is disclosed for the isolation of an enantiomerically enriched alcohol from a first mixture of an enantiomerically enriched 1-arylsulfonate-2 -hydroxy-3-butene and an enantiomerically enriched 1 -arylsulfonate- 2-acyloxy-3-butene. The process includes the steps of:(a) contacting the mixture with a reagent capable of reacting with said 1-arylsulfonate-2-hydroxy-3-butene to remove the arylsulfonate group and produce a mixture of dihydroxybutene monoesters thereby forming a second mixture containing said dihydroxybutene monoesters and unreacted enantiomerically enriched 1-arylsulfonate-2-acyloxy-3-butene(b) contacting the second mixture with reagents capable of hydrolyzing all of the acyl groups in said mixture to hydroxy groups so as to produce a third mixture comprising 1,2-dihydroxy-3-butenes and enantiomerically enriched 1-arylsulfonate-2-hydroxy-3 -butene;(c) washing said third mixture with water so as to remove said 1,2-dihydroxy-3-butenes.Type: GrantFiled: February 26, 1991Date of Patent: June 30, 1992Assignee: Eastman Kodak CompanyInventor: Neil W. Boaz
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Patent number: 5097075Abstract: 1,1,1-Trifluoro-2-hydroxy-5-benzyloxy compounds represented by the following formula (I) and optical isomers thereof: ##STR1##The compounds of the present invention are R-form and S-form when X is --C.tbd.C-- and are trans-form and cis-form both of which have respectively R-form and S-form when X is --CH.dbd.CH-- or ##STR2## ##STR3## the compound of the present invention is ##STR4## The compounds of the present invention are useful for asymmetric introduction of trifluoromethyl group and molecular designing of biologically active substances, ferroelectric liquid crystal compounds and so on.Type: GrantFiled: October 10, 1990Date of Patent: March 17, 1992Assignee: Showa Shell Sekiyu Kabushiki KaishaInventor: Tomoya Kitazume
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Patent number: 5070016Abstract: A methanol synthesis and an ethanol synthesis are integrated into a single continuous process with the by-product carbon dioxide generated in the ethanol synthesis being utilized in the methanol synthesis. The methanol synthesis and ethanol synthesis can be further integrated with isobutylene synthesis with by-product hydrogen formed during isobutylene synthesis being used as a raw material in the methanol synthesis. In the preferred embodiments the ethanol synthesis utilizes Zymomonas mobilis bacteria in anaerobic fermentation in order to maximize the amount of carbon dioxide produced in a form which can be utilized in the methanol synthesis, to reduce carbon dioxide emissions and to provide an ethnaol product which is highly suitable for reaction with the isobutylene to form ethyl tertiary butyl ether.Type: GrantFiled: March 28, 1991Date of Patent: December 3, 1991Assignee: Revolution Fuels of America, Inc.Inventor: David E. Hallberg
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Patent number: 5036005Abstract: Fuel grade ethanol is produced in continuous process employing fermentation, solvent extraction of the ethanol, extractive distillation of the ethanol-solvent extract to provide water fraction and vacuum stripping for separation of the fuel-grade ethanol and regenerated solvent.The solvent is recycled. An isoparaffin is used as a solvent and this solvent can be modified with a long chain fatty acid, alcohol or fatty alcohol or long-chain esters. Alternatively, many modifiers may be used neat.Type: GrantFiled: January 17, 1989Date of Patent: July 30, 1991Assignee: Georgia Tech Research CorporationInventor: Daniel W. Tedder
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Patent number: 5032512Abstract: This invention relates to a process for the microbiological production of compounds containing a terminal hydroxyl or epoxy group from an aliphatic substrate or a substrate with an aliphatic side chain, using microorganisms genetically engineered so that they have retained their capacity to perform the terminal oxidation of the substrate, but are no longer able to convert the resulting oxidation product further to any significant extent. Preferred substrates are n-alkanes, n-alkenes, and n-alkadienes containing 6-12 carbon atoms. Preferred micro-organisms are genetically engineered Pseudomonas oleovorans and Pseudomonas putida strains lacking an active plasmidic alkanol-dehydrogenase gene. The invention also relates to micro-organisms thus genetically engineered.Type: GrantFiled: January 14, 1988Date of Patent: July 16, 1991Assignee: Rijksuniversiteit te GroningenInventors: Bernard Witholt, Roland G. Lageveen
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Patent number: 5017484Abstract: A process for preparing an optically active 3-chloro-1, 2-propanediol by employing microorganism which can selectively metabolize (R)- or (S)-3-chloro-1,2-propanediol. The decomposition rate of the substrate can be accelerated and the substrate concentration can be increased by adding a compound having SH group to the reaction solution.According to the process of the present invention, the optically active 3-chloro-1,2-propanediol can be easily prepared starting from low-cost (R,S)-3-chloro-1, 2-propanediol.Type: GrantFiled: November 24, 1986Date of Patent: May 21, 1991Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Yoshio Nakamura, Masahiro Ogura, Yoshio Shimada, Kiyoshi Watanabe, Hideyuki Takahashi
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Patent number: 4980291Abstract: Biotechnological resolution by means of enzymatic transesterification of the relevant racemic mixture of the optical isomers of .alpha.-alkyl-substituted primary alcohols having the formula (I): ##STR1## wherein: R represents a linear or branched (C.sub.1 -C.sub.20)-alkyl or alkenyl group or an aryl group, also substituted or condensed with other groups, in particular a group of formula (II) or (III): ##STR2## wherein: R.sup.ii represents a (C.sub.1 -C.sub.8)-alkyl group, a (C.sub.1 -C.sub.4)-alkenyl group, an alkoxy, phenyl, phenoxy, benzoyl, or heterocyclic group;R.sup.iii represents a hydrogen or halogen atom;R.sup.iv represents a (C.sub.1 -C.sub.4)-alkyl group,and whereinR.sup.i represents a (C.sub.1 -C.sub.Type: GrantFiled: February 9, 1989Date of Patent: December 25, 1990Assignee: Istituto Guido Donegani S.p.A.Inventors: Daniele Bianchi, Pietro Cesti, Franco Francalanci, Walter Cabri
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Patent number: 4962031Abstract: The present invention provides a process for producing optically active compounds by a biochemical method in which specific compounds having hydroxyl groups are reacted with esters in the presence of hydrolases. The compounds have the following general formula: ##STR1## wherein X is selected from halogen atoms and a cyano group. Y is selected from the group constituting substituted phenyl groups, halogen atoms, cyano, trifluoromethyl and amino groups and alkylamino and alkyloxycarbonyl groups in which alkyl groups have 1-20 carbon atoms. R is an alkylene group having 1-20 carbon atoms and n is 0 or 1.Type: GrantFiled: May 2, 1988Date of Patent: October 9, 1990Assignee: Chisso CorporationInventors: Naoyuki Yoshida, Masakazu Kaneoya, Manabu Uchida, Hiroshi Morita
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Patent number: 4937192Abstract: A halogenation method using a haloperoxidase obtained from a fungus selected from the dematiaceous hyphomycetes. The enzyme has an optimum activity above about pH 5.0, and can oxidize chloride, bromide, or iodide ions.Type: GrantFiled: November 12, 1987Date of Patent: June 26, 1990Assignee: Cetus CorporationInventors: Jennie C. Hunter, Angela Belt, Lynn S. Sotos, Michelle E. Fonda
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Patent number: 4937191Abstract: A method producing a non-heme haloperoxidase which is substantially resistant to inactivation, at room temperature, in up to 0.3M H.sub.2 O.sub.2 for up to 25 hours, and up to 0.5mM HOCl for up to two minutes. One such haloperoxidase, isolated from Curvularia inaequalis, contains about 2 gram atoms of zinc per molecule. A halogenation reaction employing the enzyme can be performed at H.sub.2 O.sub.2 and hypohalous acid concentrations which produce rapid inactivation of heme-containing haloperoxidases.Type: GrantFiled: November 12, 1987Date of Patent: June 26, 1990Assignee: Cetus CorporationInventors: John Geigert, Te-Ning E. Liu, Thabiso N'timkulu
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Patent number: 4931399Abstract: The invention relates to a method for microbiologically resolving racemic 2,3-o-substituted glycerol esters to obtain optically activated 2,3-o-substituted glycerol with remaining esters also being optically active.Type: GrantFiled: September 9, 1985Date of Patent: June 5, 1990Assignee: The Wisconsin Alumni Research FoundationInventor: Charles J. Sih
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Patent number: 4923810Abstract: A method of resolving glycidyl esters to high enantiomeric excess involves fractionation of hydrolytic enzymes (e.g. lipases) to prepare biocatalysts with high enantioselectivity, and using these catalysts to selectively hydrolyze one enantiomer of the glycidyl esters. Also a method for fractionation includes stirring an aqueous solution of the enzyme with a solid inert adsorbent to provide an adsorbed and non-adsorbed enzyme fraction, where the non-adsorbed fraction displays a higher enantioselectivity than the crude non-fractionated enzyme. Also a composition composed of a glycidyl ester is obtained with an enantiomeric excess of greater than or equal to 97%.Type: GrantFiled: August 24, 1988Date of Patent: May 8, 1990Assignee: Genzyme CorporationInventors: Alan E. Walts, Ellen M. Fox
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Patent number: 4921799Abstract: This invention provides a new fermentation method and apparatus for the same for producing a substance by a microbial action from a gaseous substrate, wherein the cells of a microorganism fixed to a carrier are held in a reactor, an aqueous solution is fed to said reactor so as to moisten at least part of the surface of said microbial cells, and said gaseous substrate is forced to pass through the interstices of said microbial cells, thereby causing direct reaction between the microorganism and the gaseous substrate and effecting efficient biosynthesis of methane, formic acid and other substances.Type: GrantFiled: July 17, 1987Date of Patent: May 1, 1990Assignee: Kabushiki Kaisha Kobe Seiko ShoInventors: Shinko Kitaura, Yoshimasa Takahara, Shiro Nagai, Naomichi Nishio
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Patent number: 4892821Abstract: A method for introducing hydroxyl groups into vitamin D compounds at 1.alpha.- and/or 25-positions by use of a solution containing the mycelium of Actinomycetales being capable of hydroxylating vitamin D compound or the enzyme produced from the mycelium, is disclosed.Type: GrantFiled: July 5, 1988Date of Patent: January 9, 1990Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Sadafumi Omura, Joji Sasaki, Akiko Mikami, Kazutoshi Mizoue
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Patent number: 4851344Abstract: Monocarboxylic and dicarboxylic acids of up to 10 carbon atoms, which may also contain double bonds and be substituted by halogen, phenyl or hydroxyl, are microbially reduced to the corresponding alcohols by performing the reduction with carbon monoxide and/or a formate in the presence of a mediator.Type: GrantFiled: January 26, 1988Date of Patent: July 25, 1989Assignee: BASF AktiengesellschaftInventors: Helmut Simon, Herbert Lebertz
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Patent number: 4845033Abstract: Low aliphatic alcohols or organic solvents, especially ethanol are continuously produced by fermentation from sugar containing nutrient substrates. The process includes two fermentation steps or stages in which the substrate is subjected to the effects of microorganisms such as yeast. The first fermentation stage has a volume of 10 to 20% of that of the second fermentation stage. By adjusting the environmental conditions in each stage a large cell growth with a small portion of the total supplied substrate quantities takes place in the first activation stage and a high product formation rate is achieved with a considerably larger portion of the entire supplied substrate quantity in the second production stage. A partial outflow stream from the first stage is microfiltered and the permeate as well as the unfiltered outlet flow of the first stage, is directed into the second stage.Type: GrantFiled: October 6, 1988Date of Patent: July 4, 1989Assignee: Starcosa GmbHInventor: Uwe Tegtmeier
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Patent number: 4840907Abstract: A process for producing optically active dichloropropanol, which comprises cultivating an R-(+)-2,3-dichloro-1-propanol-assimilating strain belonging to the genus Pseudomonas in a culture medium containing racemate 2,3-dichloro-1-propanol, and recovering optical isomer S-(-)-2,3-dichloro-1-propanol from the culture broth, and a process for producing optically active epichlorohydrin, which comprises reacting the optical isomer S-(-)-2,3-dichloro-1-propanol obtained by the aforesaid process with an alkali.Type: GrantFiled: June 2, 1986Date of Patent: June 20, 1989Assignee: Osaka Soda Co., Ltd.Inventors: Naoya Kasai, Hisaharu Shima, Kazuya Tsujimura
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Patent number: 4837150Abstract: A process in which a culture of a methane-oxidizing bacterium or an extract thereof containing a methane oxidizing system is used as oxidizing agent for the oxidation of a higher short-chain alkane, an alkene or a cyclic organic compound.Type: GrantFiled: December 9, 1985Date of Patent: June 6, 1989Assignee: National Research Development CorporationInventors: Howard Dalton, John Colby, David I. Stirling
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Patent number: 4707447Abstract: A halogenation method using a haloperoxidase obtained from a fungus selected from the dematiaceous hyphomycetes. The enzyme has an optimum activity above about pH 5.0, and can oxidize chloride, bromide, or iodide ions.Type: GrantFiled: May 24, 1983Date of Patent: November 17, 1987Assignee: Cetus CorporationInventors: Jennie C. Hunter, Angela Belt, Lynn S. Sotos, Michelle E. Fonda
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Patent number: 4612286Abstract: A method of treating biomass having fermentable material is provided utilizing acid hydrolysis in a countercurrent diffusion treatment structure. By practicing the invention acid usage is minimized, pentose concentration in the hydrolysate solution is maximized, and ethanol, butanol, butanediol, and the alcohols can be produced without the input of any external energy whatsoever into the production method. Biomass is particlized and slurried, and then is continuously subjected to acid hydrolysis at temperature, acid concentration, and residence time conditions sufficient to effect hydrolysis of the hemicellulose in the biomass to effect separation of pentose and hexose sugars into a hydrolysate having insufficient furfural to substantially inhibit fermentation microorganism growth, while not substantially hydrolyzing the cellulose in the biomass.Type: GrantFiled: July 23, 1984Date of Patent: September 16, 1986Assignee: Kamyr, Inc.Inventors: Michael I. Sherman, Carl L. Elmore
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Patent number: 4609624Abstract: A process for producing isopropyl alcohol and useful by-products from cellulosic substrates without utilizing toxic acids. This process comprises the steps of: (1) digesting cellulosic substrates in a heated solution of sodium carbonate; (2) digesting the cellulosic product of step (1) in a heated solution containing isopropyl alcohol or aluminum isopropylate together with sodium acetate and optionally, acetic acid, to produce a biomass and a black liquid of saturated acyclic hydrocarbons; (3) mixing the biomass of step (2) with amylolytic enzymes or with xylophagous bacteria to initiate fermentation of the biomass; (4) adding the black liquid of step (2) together with basic aluminate acetate and a mixture of formaldehyde and phenol or sulfonated phenol to the mixture of step (3) and heating the resulting mixture to a temperature ranging between 120.degree. to 160.degree. C. under a pressure ranging between 1.5 and 45 kg/cm.sup.2 until isopropyl alcohol is produced.Type: GrantFiled: February 3, 1984Date of Patent: September 2, 1986Assignee: Les Services de Consultation D.B. Plus LimiteeInventor: Henri C. Rothlisberger
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Patent number: 4594324Abstract: A process in which a culture of a methane-oxidizing bacterium or an extract thereof containing a methane oxidizing system is used as oxidizing agent for the oxidation of a higher short-chain alkane, an alkene or a cyclic organic compound.Type: GrantFiled: December 28, 1982Date of Patent: June 10, 1986Assignee: National Research Development Corp.Inventors: Howard Dalton, John Colby, David I. Stirling
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Patent number: 4587216Abstract: A purified hydroxylase enzyme component A of the methane monooxygenase enzyme isolated from the soluble fraction of Methylobacterium organophilum (CRL.26) (NRRL B-11,222) is found to contain three subunits. Any component A derived from methylotrophs having the particular characteristics of this isolated component A may be employed in conjunction with the flavoprotein component C of the methane monooxygenase enzyme, preferably the flavoportein component derived from the same organism, to catalyze the oxidation of various oxidizable organic substrates to their respective oxidation products. Preferably, the substrate is propylene.Type: GrantFiled: August 31, 1983Date of Patent: May 6, 1986Assignee: Exxon Research and Engineering Co.Inventors: Ramesh N. Patel, Leonard E. Mortenson
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Patent number: 4510242Abstract: Alcohol substantially free of water is prepared by fermenting a fermentable biomass feedstock in a fermentation unit, thereby forming an aqueous fermentation liquor containing alcohol; extracting said aqueous fermentation liquor with an organic solvent containing an extractant for said alcohol, thereby forming an alcohol-organic solvent extract phase and an aqueous raffinate; contacting said alcohol-organic solvent phase with a carrier gas thereby separating said alcohol from said alcohol-organic solvent phase and forming an alcohol laden solvent vapor; and separating alcohol substantially free of water from said carrier gas.Type: GrantFiled: October 24, 1983Date of Patent: April 9, 1985Assignee: Georgia Tech Research CorporationInventor: Daniel W. Tedder
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Patent number: 4473643Abstract: A process of oxidizing a hydrocarbon which is an alkane or alkene or substituted alkane or alkene by contacting it with a culture of a bacterium as deposited under accession number NCIB 11613 or a mutant or derivative thereof which is capable of utilizing an alkane having from 6 to 28 carbon atoms as a source of carbon and energy or an enzyme extract thereof, and separating an oxidized derivative of the hydrocarbon.Type: GrantFiled: April 1, 1982Date of Patent: September 25, 1984Assignee: Imperial Chemical Industries PLCInventor: Irving J. Higgins
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Patent number: 4455373Abstract: Microbiological oxidations of organic compounds including C6 to C28 alkanes, C2 to C18 alkenes and cyclic compounds such as cyclohexane and benzene carried out using as catalysts methane-utilizing bacteria adapted to utilize methanol as a carbon source. The application also covers methane-utilizing bacteria adapted to utilize methanol as a carbon source and a method for producing such bacteria. In the method methane-utilizing bacteria are cultured in the presence of methanol vapor as principal carbon source for sufficient time to allow adaptation to occur.Type: GrantFiled: July 29, 1981Date of Patent: June 19, 1984Assignee: Imperial Chemical Industries PLCInventor: Irving J. Higgins
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Patent number: 4378434Abstract: The disclosed chemical process is carried out in a series of vertically stacked conversion (e.g. fermentation) zones which are subdivided into movable segments. Flow from one zone to another is gravity-induced. A portion of the production medium is recirculated to an upper zone, e.g. the uppermost zone, and metabolites are withdrawn from the zones. Useful metabolites include organic liquids such as alkanols made from fermentation of carbohydrate.In apparatus (10) especially suited to the process: A generally vertically disposed fermentation tower (11) defines a generally vertically extending space containing the vertically arranged zones (15a-15h). A typical zone, e.g. zone (15c) has a floor (65c) having a drain opening (165c) for the continuous discharge by gravity of partially converted feedstock to the next lower zone (15d). Each zone (e.g. 15c) is subdivided into continuously movable segments by movable partitions (157c) for advancing the feedstock in the zone toward the drain opening.Type: GrantFiled: March 31, 1980Date of Patent: March 29, 1983Assignee: Solargizer International, Inc.Inventors: Robert C. Prentice, Dale W. Mastarone
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Patent number: 4269940Abstract: Disclosed is a process for the microbiological oxidation of C.sub.1 -C.sub.6 alkanes and cycloalkanes by contacting said C.sub.1 -C.sub.6 alkanes or cycloalkanes, under aerobic conditions, in the presence of microorganisms or enzyme preparations derived therefrom, wherein said microorganisms have been aerobically grown in a nutrient containing methane. The microorganisms are newly isolated obligative and facultative methylotrophs.Type: GrantFiled: March 27, 1979Date of Patent: May 26, 1981Assignee: Exxon Research & Engineering Co.Inventors: Ramesh N. Patel, Ching-Tsang Hou, Allen I. Laskin