Polycarboxylic Acid Patents (Class 435/142)
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Patent number: 5217887Abstract: A process for the production of methylsuccinic acid represented by the formula (I): ##STR1## wherein the symbol * represents an asymmetric carbon atom, comprising the steps of culturing Candida in a medium containing squalene and producing methylsuccinic acid.Type: GrantFiled: October 10, 1991Date of Patent: June 8, 1993Assignee: Nippon Oil Co., Ltd.Inventors: Akira Tsubokura, Hisashi Yoneda, Takashi Kiyota
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Patent number: 5155043Abstract: Optically active substances are prepared by the asymmetric hydrolysis of ##STR1## with specific microorganisms.Type: GrantFiled: March 23, 1990Date of Patent: October 13, 1992Assignee: Idemitsu Kosan Company LimitedInventors: Nobuo Murakami, Masami Mochizuki
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Patent number: 5151353Abstract: Bacteria that metabolize phenylacetate along a mandelate-to-cis,cis-muconate pathway are disclosed. Bacteria that express the pathway for metabolizing phenylacetate through a mandelate intermediate can be isolated reproducibly by first selecting bacteria that can utilize both L-phenylalanine and mandelate as the sole carbon source and then blocking alternate pathways for the degradation of L-phenylalanine. The activity of selected enzymes along the mandelate-to-cis,cis-muconate pathway can be blocked in these bacteria to effect the accumulation of selected intermediates.Type: GrantFiled: March 11, 1991Date of Patent: September 29, 1992Assignee: ChemGen CorporationInventors: Steven D. Geusz, David M. Anderson
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Patent number: 5135858Abstract: An improved biological conversion of a nitrile such as acrylonitrile or a cyanopyridine into the corresponding carboxylic acid such as acrylic acid or a nicotinic acid by the action upon the nitrile of a nitrilase enzyme, in which the improvement resides in the use as the source of the enzyme of a microorganism of Rhodococcus, such as Rh. rhodochrous J-1, FERM BP-1478, which is cultured in the presence of a lactam compound.Type: GrantFiled: February 22, 1991Date of Patent: August 4, 1992Assignees: Hideaki Yamada, Nitto Kagaku Kogyo Kabushiki KaishaInventors: Hideaki Yamada, Toru Nagasawa, Tetsuji Nakamura
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Patent number: 5122461Abstract: The invention relates to a novel method for preparing pyrocatecholic compounds from monophenolic compounds using catalysis by monophenol monooxygenase in an aqueous solution containing metal ions. The metal ions form complexes with the pyrocatecholic products. This method increases the yield of pyrocatecholic products. In particular, the method of the instant invention can be used to increase the yield of L-DOPA, a drug used in the treatment of Parkinson's disease.Type: GrantFiled: November 19, 1990Date of Patent: June 16, 1992Assignee: Industrial Technology Research InstituteInventors: Kuang-Pin Hsiung, Feng-Tsun Lee, Chung-Long Hsieh
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Patent number: 5087614Abstract: Novel peptide analogues which exhibit inhibitory activity against aspartic proteinases, a novel species of actinomycetous microorganism which produces said novel peptide analogues, a process for producing said novel analogues by culturing said species and a pharmaceutical composition containing said analogues.Type: GrantFiled: November 16, 1988Date of Patent: February 11, 1992Assignee: Suntory LimitedInventors: Mitsuru Maeda, Tohru Kodama, Norio Iwasawa, Naoki Higuchi, Norihide Amano
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Patent number: 5037748Abstract: A process for producing cis-4,5-dihydro-4,5-dihydroxyphthalic acid which comprises producing cis-4,5-dihydro-4,5-dihydroxyphthalic acid and/or a salt thereof from phthalic acid and/or a salt thereof using a microorganism whose activity to decompose cis-4,5-dihydro-4,5-dihydroxyphthalic acid and/or a salt thereof has disappeared or diminished, acidifying the product system unless it is acidic, and then extracting therefrom cis-4,5-dihydro-4,5-dihydroxyphthalic acid with such an organic solvent that it is miscible with water in any proportion and the mixture of the organic solvent with water can be separated into two layers upon adding a salt thereto, in the presence of a salt, or with an alcohol having 4 carbon atoms. The process enables one to produce cis-4,5-dihydro-4,5-dihydroxyphthalic acid from phthalic acid and/or its salt in a high yield.Type: GrantFiled: July 30, 1990Date of Patent: August 6, 1991Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Minoru Matsubara, Tohru Masukawa, Norihiko Adachi, Miki Fukuta, Masao Kariya, Tohru Kodama, Toshio Omori
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Patent number: 5030568Abstract: The conversion of 2,6-dialky naphthalene to the corresponding 2,9-dicarboxy naphthalene by microbiological means is described. Exemplary means include the use of NAH7 plasmids, encoding aromatic oxygenase enzymes, in a Pseudomonas host. The conversion product is useful as a monomer in the production of high performance synthetic polymers.Type: GrantFiled: April 9, 1990Date of Patent: July 9, 1991Assignee: Minnesota Mining and Manufacturing CompanyInventors: Ting L. Carlson, Karen E. Hesselroth
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Patent number: 5026648Abstract: This invention provides novel strains of microorganisms (e.g., Pseudomonas putida Biotype A) which are capable of converting substrates such as toluene or catechol to muconic acid quantitatively by the ortho (catechol 1,2-oxygenase) pathway.Muconate lactonizing enzyme is not induced in the microorganism, thereby permitting the muconic acid to be produced and accumulated in a quantity greater than one gram of muconic acid per liter of bioconversion medium.Type: GrantFiled: January 14, 1986Date of Patent: June 25, 1991Assignee: Celgene CorporationInventor: Peter C. Maxwell
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Patent number: 4999292Abstract: Bacteria that metabolize phenylacetate along a mandelate-to-cis,cis-muconate pathway are disclosed. Bacteria that express the pathway for metabolizing phenylacetate through a mandelate intermediate can be isolated reproducibly by first selecting bacteria that can utilize both L-phenylalanine and mandelate as the sole carbon source and then blocking alternate pathways for the degradation of L-phenylalanine. The activity of selected enzymes along the mandelate-to-cis,cis-muconate pathway can be blocked in these bacteria to effect the accumulation of selected intermediates.Type: GrantFiled: December 31, 1987Date of Patent: March 12, 1991Inventors: Steven D. Geusz, David M. Anderson
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Patent number: 4968612Abstract: This invention provides a continuous bioconversion process in which a non-growth toluene substrate is bio-oxidized by a specific microbe mutant strain to accumulated extracellular muconic acid at a bioreactor production rate of at least about 5 grams of muconic acid per liter of fermentation medium per hour.Essential features of the invention process include a continuous feed of whole cell-containing fermentation broth from an auxiliary cell growth and enzyme induction fermentation zone into the main fermentation zone, and a purge stream of whole cell-containing fermentation broth from the main fermentation zone.Type: GrantFiled: July 27, 1984Date of Patent: November 6, 1990Assignee: Celgene CorporationInventor: Jih-Han Hsieh
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Patent number: 4965201Abstract: The invention provides a process for preparing medium chain dicarboxylic acids by biochemical oxidation so that in particular C.sub.8 and C.sub.10 dicarboxylic acids are prepared from nontoxic levels of C.sub.8 -C.sub.14 fatty acids using a nitrogen-restricted yeast propagated in a carbon substrate containing growth medium. Preferably the fatty material is supplied to the yeast in the form of a glyceride. Also it is preferred that the amount of nitrogen in the biomass is between 4 and 9%, in particular between 5.5 and 7% (w/w).Type: GrantFiled: May 11, 1989Date of Patent: October 23, 1990Inventors: John Casey, Roy T. Dobb, Roger Jeffcoat
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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: 4929396Abstract: This invention provides hexamethylenediamine muconate salt. This novel salt can be produced by bioconversion of toluene to muconic acid in the presence of hexamethylenediamine. Hydrogenation of this salt provides hexamethylenediamine adipate salt.Type: GrantFiled: October 17, 1984Date of Patent: May 29, 1990Assignee: Celgene CorporationInventors: Sol J. Barer, Peter C. Maxwell, Jih-Han Hsieh
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Patent number: 4925798Abstract: 3-hydroxydicarboxylic acids of 12-18 carbon atoms are produced microbiologically from n-alkanes employing the yeast mutant Candida tropicalis DSM 3152.Type: GrantFiled: January 3, 1989Date of Patent: May 15, 1990Assignee: Huels AktiengesellschaftInventor: Frank F. Hill
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Patent number: 4923811Abstract: A process for carrying out enzymatic oxidations is described.Type: GrantFiled: August 28, 1987Date of Patent: May 8, 1990Assignee: BASF AktiengesellschaftInventors: Helmut Simon, Helmut Guenther
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Patent number: 4904389Abstract: A process for separation of multicomponent mixtures of dicarboxylic acids, especially, mixtures of C.sub.8 -C.sub.24 saturated and unsaturated acids is derived from a fermentation process, in which an aqueous feed solution containing the mixture of dicarboxylic acids is adjusted in pH value depending on the permeability of the component to be separated and over 95% of the saturated component is separated from the unsaturated material by passing the mixture is content with a membrane filter.Type: GrantFiled: June 17, 1988Date of Patent: February 27, 1990Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Heinrich Waldhoff, Joachim Schindler, Holger Viehweg
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Patent number: 4877731Abstract: An improved fermentation process for producing carboxylic acids is disclosed. The improvement comprises growing fungi of the genus Rhizopus in a culture medium containing a carbon source, a nitrogen source and inorganic salts, under conditions of controlled oxygen availability wherein the dissolved oxygen concentration for the cell growth phase is between 80% and 100% and where the dissolved oxygen concentration for the acid production phase is between 30% and 80%.Type: GrantFiled: June 27, 1988Date of Patent: October 31, 1989Assignee: E. I. Du Pont De Nemours and CompanyInventors: Lorraine B. Ling, Thomas K. Ng
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Patent number: 4871667Abstract: Muconic acid is obtained from the culture of strains of Arthrobacter sp. mutant strains, strains belonging to Corynebacterium acetoacidophilum, Corynebacterium lilium, genus Brevibacterium or genus Microbacterium.Type: GrantFiled: November 20, 1985Date of Patent: October 3, 1989Assignees: Agency of Industrial Science & Technology, Ministry of International Trade and Industry of JapanInventors: Yukio Imada, Nobuji Yoshikawa, Sumiko Mizuno, Takashi Mikawa
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Patent number: 4833078Abstract: This invention provides a semi-continuous fermentation process which is operated in a repeated fed-batch mode to maintain cell bioconversion productivity at a high level without product inhibition of enzymatic activity. The process is illustrated by the bioconversion of toluene or catechol via the ortho pathway to muconic acid which accumulates in the fermentation medium in a quantity up to about 50 grams per liter.Type: GrantFiled: June 22, 1984Date of Patent: May 23, 1989Assignee: Celgene CorporationInventor: Jih-Han Hsieh
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Patent number: 4828992Abstract: The process for the manufacture of the compound of the general structural formula ##STR1## which is a 3-hydroxy-3-methylglutarylcoenzyme A (HMG-CoA) synthase inhibitor and useful as an antihypercholesterolemic agent for the treatment of disease in which the inhibition of cholesterol biosynthesis would be useful, and which is an antifungal agent is disclosed.Type: GrantFiled: February 3, 1986Date of Patent: May 9, 1989Assignee: Merck & Co., Inc.Inventors: Sagrario M. Del Val, Maria I. M. Fernandez, Richard L. Monaghan
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Patent number: 4827030Abstract: 3-hydroxydicarboxylic acids of 12-18 carbon atoms are produced microbiologically from n-alkanes employing the yeast mutant Candida tropicalis DSM 3152.Type: GrantFiled: April 23, 1986Date of Patent: May 2, 1989Assignee: Huels AktiengesellschaftInventor: Frank F. Hill
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Patent number: 4731328Abstract: This invention provides novel strains of microorganisms (e.g., Pseudomonas putida Biotype A) which are capable of converting substrates such as toluene or catechol to muconic acid quantitatively by the ortho (catechol 1,2-oxygenase) pathway.Muconate lactonizing enzyme is not induced in the microorganism, thereby permitting the muconic acid to be produced and accumulated in a quantity greater than one gram of muconic acid per liter of bioconversion medium.Type: GrantFiled: July 22, 1983Date of Patent: March 15, 1988Assignee: Celgene CorporationInventor: Peter C. Maxwell
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Patent number: 4725542Abstract: This invention provides a process for producing nylon 6,6 salt which involves bioconversion of toluene to muconic acid in the presence of hexamethylenediamine to yield hexamethylenediamine muconate salt. Hydrogenation of this salt provides an aqueous solution of the desired hexamethylenediamine adipate salt.Type: GrantFiled: January 13, 1983Date of Patent: February 16, 1988Assignee: Celgene CorporationInventors: Sol J. Barer, Peter C. Maxwell, Jih-Han Hsieh
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Patent number: 4657863Abstract: This invention provides a process for stabilizing a population of a mutant microorganism in a bioconversion system whereby growth of revertant cells is suppressed.The process involves limiting a nutrient which is essential for cell growth so that the cells selectively grow on a growth carbon source rather than on a non-growth carbon source which is present. The revertant cells being suppressed have a similar ability as the parent strain of the mutant microorganism to grow on the non-growth carbon source in the bioconversion system.The non-growth carbon source in the bioconversion system is metabolized to an extracellular accumulating quantity of a desired metabolite, e.g., toluene is converted to muconic acid.Type: GrantFiled: April 11, 1983Date of Patent: April 14, 1987Assignee: Celanese CorporationInventors: Peter C. Maxwell, Jin-Han Hsieh, John C. Fieschko
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Patent number: 4624920Abstract: A process for the preparation of a dicarboxylic acid using a thermophilic croorganism, and the microorganism used. The process involves cultivating a microorganism belonging to the genus Mycobacterium which produces a dicarboxylic acid at high temperatures in a medium to which a substrate selected from among normal paraffins, fatty acids, and their derivatives, each containing 6 to 22 carbon atoms, has been added, so that a dicarboxylic acid containing 6 to 22 carbon atoms is formed and accumulated in the medium, and collecting the dicarboxylic acid.Type: GrantFiled: November 20, 1984Date of Patent: November 25, 1986Assignee: Chairman of Research Association for Biotechnology, Eiji SuzukiInventors: Shigeo Inoue, Yoshiharu Kimura, Shigehito Adachi
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Patent number: 4608338Abstract: This invention provides an improved bioconversion system in which a non-growth organic substrate is bio-oxidized to a carboxylic acid product, and the carboxylic acid product is recovered as a precipitate and the resultant fermentation broth is suitable for recycle to the bioreactor. A useful water-insoluble salt is also recovered as a byproduct of the process.Type: GrantFiled: June 10, 1982Date of Patent: August 26, 1986Assignee: Celanese CorporationInventor: Jih-Han Hsieh
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Patent number: 4588688Abstract: This invention provides a process for bioconversion of an organic substrate (e.g., ethylbenzene or catechol) to muconic acid.This invention further provides a procedure for constructing novel strains of microorganisms (e.g., Pseudomonas putida Biotype A) which are capable of converting an organic substrate to muconic acid quantitatively by the ortho (catechol 1,2-oxygenase) pathway.Muconate lactonizing enzyme is not induced in the microorganisms, thereby permitting the muconic acid to be produced and accumulated in a quantity greater than one gram of muconic acid per liter of growth medium.Type: GrantFiled: July 22, 1983Date of Patent: May 13, 1986Assignee: Celanese CorporationInventor: Peter C. Maxwell
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Patent number: 4564594Abstract: An improved fermentation process for producing carboxylic acids, especially fumaric acid, is disclosed. The improvement comprises growing fungi of genus Rhizopus in the presence of an effective amount of at least one additive selected from the group consisting of fatty acid esters having fatty acid residues of 12 to 24 carbons, and triglyceride mixtures.Type: GrantFiled: June 30, 1983Date of Patent: January 14, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventors: Israel Goldberg, Barry Stieglitz
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Patent number: 4536474Abstract: An undifferentiated symbiotic combination of alga and fungus cells, obtained directly from a lichen explant, are cultured in a media under appropriate conditions to produce aromatic lichenous substances and these substances are recovered.Type: GrantFiled: September 30, 1982Date of Patent: August 20, 1985Assignee: Nippon Paint Co., Ltd.Inventors: Yoshikazu Yamamoto, Ryuzo Mizuguchi, Yasuyuki Yamada
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Patent number: 4535059Abstract: This invention provides an improved fermentation process for bioconversion of toluene to muconic acid.The process involves operating the bioconversion system under phosphate-limiting conditions so as to achieve an increase in specific muconic acid productivity with a stabilized population of microorganism such as an ATCC No. 31,916 type of Pseudomonas putida Biotype A mutant strain.Type: GrantFiled: January 13, 1983Date of Patent: August 13, 1985Assignee: Celanese CorporationInventors: Jih-Han Hsieh, Sol J. Barer, Peter C. Maxwell
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Patent number: 4490467Abstract: A process for producing polysaccharide consisting of a partially acetylated variable block copolymer of D-mannuronic and L-guluronic acid residues comprises growing a biologically pure culture of a Pseudomonas mendocina microorganism selected from the group consisting of NCIB 11687, 11688, and 11689 in an aqueous nutrient medium by submerged aerobic fermentation of an assimilable carbon source and recovering the polysaccharide. Biologically pure cultures of the organisms are another feature of the invention.Type: GrantFiled: October 29, 1982Date of Patent: December 25, 1984Assignee: Kelco Biospecialties Ltd.Inventors: Trevor R. Jarman, Andrew J. Hacking
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Patent number: 4480034Abstract: This invention provides a continuous bioconversion process in which a cross-flow membrane filtration zone is employed to recover a whole cell-containing retentate stream and a cell-free bioconversion product-containing permeate stream. The retentate stream is recycled to the fermentation zone. In a specific embodiment, toluene is bio-oxidized to muconic acid with a microorganism such as Pseudomonas putida Biotype A strain ATCC 31,916. The muconic acid is recovered as a precipitate from the cell-free permeate fermentation broth, and the fermentation broth is recycled in the process.Type: GrantFiled: June 10, 1982Date of Patent: October 30, 1984Assignee: Celanese CorporationInventor: Jih-Han Hsieh
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Patent number: 4474882Abstract: A process for the preparation of an unsaturated dicarboxylic acid which comprises cultivating under aerobic conditions a yeast belonging to Candida tropicalis which is capable of producing an unsaturated dicarboxylic acid from an unsaturated fatty acid or its ester, such as Candida tropicalis 104-04 strain, in a medium containing an unsaturated fatty acid having 14 to 22 carbon atoms or its ester, to produce an unsaturated dicarboxylic acid having 14 to 22 carbon atoms; or effecting oxidation of said fatty acid or its ester in the presence of microorganisms of said yeast produced in advance by cultivation in an assimilable carbon source to produce an unsaturated dicarboxylic acid having 14 to 22 carbon atoms; and then recovering the thus-produced unsaturated dicarboxylic acid.Type: GrantFiled: September 21, 1981Date of Patent: October 2, 1984Assignee: Daicel Chemical Industries, Ltd.Inventors: Etsumi Kunishige, Tsuyoshi Morinaga
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Patent number: 4444881Abstract: A process is provided for the recovery of organic acids from dilute aqueous solutions. The acid in the form of its calcium salt is treated with a tertiary amine carbonate and the resulting trialkylammonium salt of the acid is isolated and heated to give the acid plus a tertiary amine.Type: GrantFiled: June 27, 1983Date of Patent: April 24, 1984Assignee: CPC International Inc.Inventor: Branko Urbas
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Patent number: 4433053Abstract: Continuous fermentation of Alcaligenes micro-organisms capable of accumulating PHB under limitation of a nutrient required for growth, but not PHB accumulation, so that the PHB content is above 25% by weight. By means of this the carbon in the carbon and energy source, i.e. the substrate, is utilized more efficiently.Type: GrantFiled: August 10, 1981Date of Patent: February 21, 1984Assignee: Imperial Chemical Industries PLCInventors: Lorenzo Hughes, Kenneth R. Richardson
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Patent number: 4400468Abstract: A process is provided for producing adipic acid from a renewable resource, i.e., biomass. The process comprises: hydrolyzing the renewable resource to provide 5-hydroxymethylfurfural, hydrogenating the 5-hydroxymethylfurfural in the presence of a catalyst to provide 2, 5-tetrahydrofurandiomethanol, treating the 2, 5-tetrahydrofurandiomethanol with hydrogen in the presence of a catalyst to provide 1, 6 hexanediol, and oxidizing the 1, 6 hexanediol in the presence of a microorganism to provide adipic acid. The formation of the adipic acid is provided with the microorganism of Gluconobacter oxydans subsp. oxydans. The renewable resources are wastes selected from the group consisting of paper, wood, corn stalks, and logging residues.Type: GrantFiled: October 5, 1981Date of Patent: August 23, 1983Assignee: Hydrocarbon Research Inc.Inventor: Marcel Faber
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Patent number: 4355107Abstract: This invention provides a process for microbiological oxidation of toluene to muconic acid.The toluene oxidation is achieved with novel strains of microorganisms (e.g., Pseudomonas putida Biotype A) which are capable of converting toluene to muconic acid quantitatively by the ortho (.beta.-ketoadipate) pathway.Munonate lactonizing enzyme is not induced in the microorganism, thereby permitting the muconic acid to be produced and accumulated in a quantity greater than one gram of muconic acid per liter of conversion medium.Type: GrantFiled: July 27, 1981Date of Patent: October 19, 1982Assignee: Celanese CorporationInventor: Peter C. Maxwell
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Patent number: 4339536Abstract: Disclosed in this invention is a process for producing a long-chain dicarboxylic acid by culturing a fungus belonging to Candida tropicalis which has the ability to produce a long-chain dicarboxylic acid in a liquid medium containing a straight-chain saturated hydrocarbon as substrate, the production of said dicarboxylic acid being phenomenally increased by properly adjusting the pH of the medium in the course of culture. There is also disclosed a method for advantageously separating and collecting said dicarboxylic acid from a fermentation broth containing said dicarboxylic acid produced by said culture.Type: GrantFiled: June 3, 1980Date of Patent: July 13, 1982Assignee: Nippon Mining Co., Ltd.Inventors: Koichi Kato, Namio Uemura
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Patent number: 4332904Abstract: A vessel capable of passing a liquid therethrough is packed with a support having at least hydrophilicity and microorganism cells are inoculated to the support, retained and cultivated therein. A reaction substrate is fed to the vessel and brought into contact with the microorganism, whereby the microorganism is allowed to propagate within the support and act upon the reaction substrate to induce decomposition or synthetic reactions thereof.Type: GrantFiled: April 17, 1979Date of Patent: June 1, 1982Assignee: Agency of Industrial Science & Technology, Ministry of International Trade & IndustryInventors: Ryuichiro Kurane, Tomoo Suzuki, Yoshimasa Takahara
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Patent number: 4275158Abstract: A method for the oxidation of hydrocarbons to monocarboxylic acids and then to dicarboxylic acids by the aerobic cultivation or resting cell reaction of the organism Debaryomyces vanriji (BR-308) ATCC 20588.Type: GrantFiled: January 7, 1980Date of Patent: June 23, 1981Assignee: Bio Research Center Company, Ltd.Inventors: Akira Taoka, Seiichi Uchida
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Patent number: 4220720Abstract: A method for the oxidation of hydrocarbons to monocarboxylic acids and thence to dicarboxylic acids by the aerobic resting cell reaction of the organism Debaryomyces phaffii ATCC 20499.Type: GrantFiled: December 11, 1978Date of Patent: September 2, 1980Assignee: Bio Research Center Co., Ltd.Inventors: Akira Taoka, Seiichi Uchida