Purification Or Recovery Patents (Class 549/413)
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Patent number: 11072760Abstract: A method of purifying biomass-based lipid material, as disclosed includes providing a feed of biomass-based lipid material; optionally drying the feed; removing oxygen from the feed under reduced pressure; heat treating the feed at 180 to 300° C. under reduced pressure to solidify at least part of phosphorous and/or metal containing impurities, simultaneously distilling off at least part of free fatty acids and low molecular weight nitrogen compounds, to obtain at least a fraction containing free fatty acids and low molecular weight nitrogen compounds, and heat treated biomass-based lipid material containing degraded phosphorous and/or metal containing impurities in solid form; and removing the solid degraded phosphorous and/or metal containing impurities from the second fraction.Type: GrantFiled: December 28, 2018Date of Patent: July 27, 2021Assignee: NESTE OYJInventors: Jukka-Pekka Pasanen, Jarmo Halttunen, Annika Malm, Väinö Sippola
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Patent number: 10689594Abstract: A process for recovering tocotrienols/tocopherols, carotenoids and sterols from crude vegetable oil, characterised in that prior to the recovery steps, the amount of the free fatty acids in the oil is reduced to 3.50% by weight by distillation or neutralization.Type: GrantFiled: May 7, 2015Date of Patent: June 23, 2020Inventor: David Sue San Ho
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Patent number: 10626068Abstract: A method for squalene extraction from a seed oil includes converting fatty acids of the seed oil into soap by subjecting the seed oil to a saponification reaction to obtain a saponified product, and adsorbing the fatty acids of the seed oil on surfaces of iron oxide nanoparticles to obtain iron oxide nanoparticles coated with fatty acids. The method may further include washing the iron oxide nanoparticles coated with fatty acids with a polar solvent to obtain a third mixture including a polar phase and the iron oxide nanoparticles coated with fatty acids, separating the iron oxide nanoparticles coated with fatty acids from the third mixture by a magnetic field, mixing the polar phase with a non-polar solvent and distilled water to obtain a two-phase solution, the two-phase solution including a non-polar phase and an aqueous phase, and separating and drying the non-polar phase to obtain squalene.Type: GrantFiled: September 19, 2018Date of Patent: April 21, 2020Inventors: Fatemeh Hataminia, Nafiseh Farhadian, Mahmoud Ebrahimi
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Patent number: 10357474Abstract: Plant extracts, compositions, pharmaceutical compositions and methods of making and using the same are provided herein. The compositions comprise ?-tocotrienol (GT3) and ?-tocotrienol (DT3) in ratios wherein the DT3 is predominate. The compositions are useful for radioprotection and radiomitigation in subjects in need thereof.Type: GrantFiled: June 1, 2018Date of Patent: July 23, 2019Assignees: BIOVENTURES, LLC, UNIVERSIDAD TECNICA PARTICULAR DE LOJA, THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE DEPARTMENT OF VETERANS AFFAIRSInventors: Cesar M. Compadre, Philip Breen, Nukhet Aykin-Burns, Martin Hauer-Jensen, Raul G. Enriquez, Sujay Kharade, Omar Malagon, Yadira Ordonez, Edgar Ojeda, Shraddha Thakkar, E. Nathalie Pineda, Darin Jones
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Patent number: 9993456Abstract: Plant extracts, compositions, pharmaceutical compositions and methods of making and using the same are provided herein. The compositions comprise ?-tocotrienol (GT3) and ?-tocotrienol (DT3) in ratios wherein the DT3 is predominate. The compositions are useful for radioprotection and radiomitigation in subjects in need thereof.Type: GrantFiled: September 15, 2014Date of Patent: June 12, 2018Assignees: The Board of Trustees of the University of Arkansas, Universidad Tecnica Particular De Loja, The United States of America as Represented by the Department of Veterans AffairsInventors: Cesar M. Compadre, Philip Breen, Nukhet Aykin-Burns, Martin Hauer-Jensen, Raul G. Enriquez, Sujay Kharade, Omar Malagon, Yadira Ordonez, Edgar Ojeda, Shraddha Thakkar, E. Nathalie Pineda, Darin Jones
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Patent number: 9963438Abstract: A method is provided for manufacturing high-purity vitamin E compounds by selectively separating vitamin E compounds such as tocotrienols and tocopherols from oil raw materials such as deodorized distillate, and more specifically, a method is provided, applying to a rich fraction of vitamin E compounds, for obtaining high-purity vitamin E compounds by separating and removing only free fatty acids contained as impurities. The method comprises a process in which a solution containing vitamin E compounds and free fatty acids is placed in contact with a weakly basic anion exchanger, and the free fatty acids are preferentially adsorbed.Type: GrantFiled: September 7, 2016Date of Patent: May 8, 2018Assignee: TOHOKU UNIVERSITYInventors: Naomi Shibasaki-Kitakawa, Kousuke Hiromori, Kousei Kanuma, Tomone Sasayama
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Patent number: 9447361Abstract: The present invention relates to the use of at least one vegetable oil refining industry by-product to obtain a purified total unsaponifiable of vegetable oil cleared of the impurities initially present in the said by-product, advantageously cleared of sapid and odorous compounds and/or chemical compounds resulting from the deterioration and the degradation of vegetable oils. The invention further relates to a method for obtaining a purified total unsaponifiable of vegetable oil from at least one vegetable oil refining industry by-product. The invention further relates to a purified total unsaponifiable of vegetable oil able to be obtained by this method, as well as compositions containing such an unsaponifiable. The invention further relates to such unsaponifiables or such compositions for the use thereof as a drug, medical device, dermatological agent, cosmetic agent or nutraceutical, in humans or animals.Type: GrantFiled: January 31, 2012Date of Patent: September 20, 2016Assignee: LABORATOIRES EXPANSCIENCEInventors: Jacques Legrand, Alex Saunois, Caroline Baudouin, Philippe Msika
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Patent number: 9078850Abstract: Various systems and processes for extracting Vitamin E from a fatty acid distillate (FAD) having a Vitamin E component are disclosed. The process includes preparing a mixture of a FAD and a non-polar solvent (e.g., hexane). The mixture can be sequentially cooled to a series of pre-determined temperatures. As the mixture is sequentially cooled to each of the pre-determined temperatures within the series of pre-determined temperatures, non-Vitamin E components present in the FAD can form solid fractions within the mixture at the various pre-determined temperature stages. The process further includes removing the solid fractions from the mixture at each of the pre-determined temperature stages. After completion of a number of cooling and separation stages or cycles, the non-polar solvent can be removed from the remaining mixture to recover a Vitamin E extract.Type: GrantFiled: December 23, 2009Date of Patent: July 14, 2015Assignees: The Thailand Research Fund, Chiang Mai University, Chumporn Palm Oil Industry Public Company LimitedInventors: Patcharin Raviyan, Kriengkai Soinak
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Patent number: 8937191Abstract: Disclosed is a process for the production of high purity alpha-tocotrienol from palm oil extract. More particularly, the invention relates to a process for the separation of alpha-tocotrienol from a mixtures of other tocotrienols and tocopherols and the use of a simplified separation scheme based on a combination of solid phase extraction and simulated moving bed (SMB) separation steps employing polar phase simulated moving bed operation. The process is useful for providing a continuous route and a simplified processing route to providing pure alpha-tocotrienol as a major product essentially free of other tocotrienols and tocopherols including: beta-tocopherol, gamma-tocotrienol, delta-tocotrienol, gamma-tocopherol, delta-tocopherol, front end and back end carotenoids, and alpha-tocopherol as a by-product from palm oil extract. Alpha-tocotrienol is a form of vitamin E and may be useful as a treatment for preventing stroke or reducing brain and nerve damage following a stroke.Type: GrantFiled: December 20, 2012Date of Patent: January 20, 2015Assignee: OROCHEM Technologies, Inc.Inventors: Anil Oroskar, Deepak Sharma, Vanshidhar Singh, Anand Oroskar, Gautham Oroskar
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Publication number: 20140221674Abstract: The invention discloses novel processes for production, enrichment and/or isolation of alpha-tocotrienol from source material comprising at least one non-alpha-tocotrienol, such as natural extracts comprising mixed tocotrienols.Type: ApplicationFiled: September 26, 2013Publication date: August 7, 2014Applicant: Edison Pharmaceuticals, Inc.Inventors: Kieron E. Wesson, Andrew W. Hinman, Orion D. Jankowski
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Publication number: 20140179933Abstract: Disclosed is a process for the production of high purity alpha-tocotrienol from palm oil extract. More particularly, the invention relates to a process for the separation of alpha-tocotrienol from a mixtures of other tocotrienols and tocopherols and the use of a simplified separation scheme based on a combination of solid phase extraction and simulated moving bed (SMB) separation steps employing polar phase simulated moving bed operation. The process is useful for providing a continuous route and a simplified processing route to providing pure alpha-tocotrienol as a major product essentially free of other tocotrienols and tocopherols including: beta-tocopherol, gamma-tocotrienol, delta-tocotrienol, gamma-tocopherol, delta-tocopherol, front end and back end carotenoids, and alpha-tocopherol as a by-product from palm oil extract. Alpha-tocotrienol is a form of vitamin E and may be useful as a treatment for preventing stroke or reducing brain and nerve damage following a stroke.Type: ApplicationFiled: December 20, 2012Publication date: June 26, 2014Applicant: OROCHEM TECHNOLOGIES, INC.Inventors: Anil Oroskar, Deepak Sharma, Vanshidhar Singh, Anand Oroskar, Gautham Oroskar
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Patent number: 8759547Abstract: A process for the extraction of Vitamin E from annatto plant matter is disclosed wherein annatto seed matter is subjected, before extraction, to acidification using amla fruit matter. After the acidification, the mixture of the two plant matters is extracted by water. The acidification converts the vitamin E compounds in the plant matter into more water-soluble forms, thus enhancing the vitamin yield. More of the vitamin is obtained in the ester form than in the form of vitamin alcohols. Processing time is reduced.Type: GrantFiled: July 30, 2012Date of Patent: June 24, 2014Inventors: Ramaswamy Rajendran, Kamala Rajendran
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Publication number: 20140039206Abstract: The present invention relates to a process for isolation of micronutrients from deodorizer distillate comprising free fatty acids, the process comprises the following steps: (i) treating the deodorizer distillate in an esterification step with glycerol, which esterification step is autocatalysed, producing a feedstock of acyl glycerides, and discharging excess of glycerol and produced water; (ii) transferring the feedstock of acyl glycerides having a water content less than 1500 ppm and a free fatty acid content less than 3 wt % to a transesterification step and treating the feedstock of acyl glycerides with methanol to produce a crude biodiesel product; and (iii) refining the crude biodiesel product in a distillation step, and separating the crude biodiesel product into three fractions 1) fatty acid methyl esters, 2) micronutrient rich product comprising tocopherol, and 3) light hydrocarbons.Type: ApplicationFiled: April 12, 2012Publication date: February 6, 2014Applicant: ALFA LAVAL CORPORATE ABInventors: Susanne Jonsson, Bent Sarup
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Patent number: 8575369Abstract: The invention discloses novel processes for production, enrichment and/or isolation of alpha-tocotrienol from source material comprising at least one non-alpha-tocotrienol, such as natural extracts comprising mixed tocotrienols.Type: GrantFiled: January 25, 2012Date of Patent: November 5, 2013Assignee: Edison Pharmaceuticals, Inc.Inventors: Kieron E. Wesson, Andrew W. Hinman, Orion D. Jankowski
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Publication number: 20130274489Abstract: The invention relates to a method for obtaining and purifying phytosterols and/or tocopherols from distillation residue from a transesterification of vegetable oils, in particular from the vegetable oil-based fatty acid methyl ester production for the field of use of biodiesel (FAME), comprising a first transesterification stage for converting partial glycerides contained in the distillation residue; separating the glycerin phase from a reaction mixture resulting from the first transesterification stage; a second transesterification stage for converting sterol esters contained in the reaction mixture; adding water to the reaction mixture after the second transesterification stage in order to generate a multiphase system; simultaneously or sequentially separating the phases of the multiphase system into a substantially sterol-containing phase; a substantially glycerin- and methanol-containing aqueous phase; and a tocopherol-containing methyl ester phase; and obtaining phytosterols from the sterol-containing phType: ApplicationFiled: November 2, 2011Publication date: October 17, 2013Applicant: VERBIO VEREINIGTE BIOENERGIE AGInventors: Joachim Lemp, Nico Baade, Emanuel Pöhls
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Publication number: 20130178519Abstract: A process for the extraction of Vitamin E from annatto plant matter is disclosed wherein annatto seed matter is subjected, before extraction, to acidification using amla fruit matter. After the acidification, the mixture of the two plant matters is extracted by water. The acidification converts the vitamin E compounds in the plant matter into more water-soluble forms thus enhancing the vitamin yield. More of the vitamin is obtained in the ester form than in the form of vitamin alcohols. Processing time is reduced.Type: ApplicationFiled: July 30, 2012Publication date: July 11, 2013Inventors: Rajendran Ramaswamy, Kamala Ramaswamy
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Patent number: 8420838Abstract: According to the invention, a process for the rectification of mixtures of high-boiling air- and/or temperature-sensitive substances which require a high separation efficiency is proposed, in particular a process for the working-up of a VE- or VEA-containing product stream. The process is characterized in particular in that, in a first purification stage, low-boiling products and unspecified isomers of the useful product are separated from the product stream virtually without loss of useful product and that, in a second purification stage, the useful product is removed in a stream having a purity of >97% by weight and a further stream having a purity of >92% by weight. A preferred embodiment of the process serves for working up VEA, in which the loss of useful product in the first purification stage is less than 5%, based on that amount of VEA in the feed which is added to the purification stage per unit time.Type: GrantFiled: October 25, 2010Date of Patent: April 16, 2013Assignee: DSM IP Assets B.V.Inventors: Juan Herguijuela, Werner Pietzonka, Angela Wildermann, Thomas Wolf
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Patent number: 8404086Abstract: Effect separation of a composition of matter that includes at least two seed or plant oil derivatives into at least one desired product stream using at least two separation operations, which are independently selected from among several potential separation operations, in conjunction with at least one recycle stream from a separation operation.Type: GrantFiled: June 20, 2008Date of Patent: March 26, 2013Assignee: Dow Global Technologies LLCInventors: George J. Frycek, Shawn D. Feist, Timothy C. Frank, Zenon Lysenko, Joe D. Phillips, Bruce W. Pynnonen
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Publication number: 20120130094Abstract: Various systems and processes for extracting Vitamin E from a fatty acid distillate (FAD) having a Vitamin E component are disclosed. The process includes preparing a mixture of a FAD and a non-polar solvent (e.g., hexane). The mixture can be sequentially cooled to a series of pre-determined temperatures. As the mixture is sequentially cooled to each of the pre-determined temperatures within the series of pre-determined temperatures, non-Vitamin E components present in the FAD can form solid fractions within the mixture at the various pre-determined temperature stages. The process further includes removing the solid fractions from the mixture at each of the pre-determined temperature stages. After completion of a number of cooling and separation stages or cycles, the non-polar solvent can be removed from the remaining mixture to recover a Vitamin E extract.Type: ApplicationFiled: December 23, 2009Publication date: May 24, 2012Inventors: Patcharin Raviyan, Kriengkai Soinak
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Patent number: 8106223Abstract: The invention discloses novel processes for production, enrichment and/or isolation of alpha-tocotrienol from source material comprising at least one non-alpha-tocotrienol, such as natural extracts comprising mixed tocotrienols.Type: GrantFiled: October 27, 2009Date of Patent: January 31, 2012Assignee: Edison Pharmaceuticals, Inc.Inventors: Kieron E. Wesson, Andrew W. Hinman, Orion D. Jankowski
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Publication number: 20110213167Abstract: A palm oil of superior chromaticity and flavor and a manufacturing method therefor with which palm oil can be obtained with good yield even if a chemical refining method of alkaline deacidification is performed. Also a palm oil manufacturing method with which deodorized distillates wherein useful components have been highly concentrated can be obtained, the deodorized distillates and a manufacturing method therefor. Refined palm oil and deodorized distillates as by-product are manufactured with a manufacturing process flow including a process wherein the palm starting material is steamed within 24 hours of harvesting and then pressed to obtain crude palm oil, a subsequent refining process wherein the crude palm oil undergoes alkaline deacidification to obtain the alkaline deacidified palm oil, and a deodorizing process.Type: ApplicationFiled: October 27, 2009Publication date: September 1, 2011Applicant: The Nisshin OilliO Group, LtdInventors: Hideaki Maki, Kunihiko Tokunaga, Yasutaka Tsuyuki, Takuya Hiyama, Toshinori Saida, Jun Itou, Ryouhei Komori
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Patent number: 7858813Abstract: According to the invention, a process for the rectification of mixtures of high-boiling air- and/or temperature-sensitive substances which require a high separation efficiency is proposed, in particular a process for the working-up of a VE- or VEA-containing product stream. The process is characterized in particular in that, in a first purification stage, low-boiling products and unspecified isomers of the useful product are separated from the product stream virtually without loss of useful product and that, in a second purification stage, the useful product is removed in a stream having a purity of >97% by weight and a further stream having a purity of >92% by weight. A preferred embodiment of the process serves for working up VEA, in which the loss of useful product in the first purification stage is less than 5%, based on that amount of VEA in the feed which is added to the purification stage per unit time.Type: GrantFiled: August 13, 2005Date of Patent: December 28, 2010Assignee: DSM IP Assets B.V.Inventors: Juan Herguijuela, Werner Pietzonka, Angela Wildermann, Thomas Wolf
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Patent number: 7544822Abstract: The present invention relates to an improved and integrated process for the extraction and purification of tocotrienols or tocopherols, carotenoids and sterols from vegetable and other edible oils. Fatty acids in the vegetable oils are subjected to alcoholic osterification to form ester-rich layer that includes fatty acid alkyl esters, carotenoids, tocotrienols or tocopherols, and sterols. The advantages of this process are that the tocotrienols or tocopherols, carotenoids and sterols are produced efficiently without any substantial decomposition or degradation of these phytonutrients.Type: GrantFiled: November 18, 2004Date of Patent: June 9, 2009Assignee: Carotech Bhd.Inventor: David Sue San Ho
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Publication number: 20080194846Abstract: According to the invention, a process for the rectification of mixtures of high-boiling air- and/or temperature-sensitive substances which require a high separation efficiency is proposed, in particular a process for the working-up of a VE- or VEA-containing product stream. The process is characterized in particular in that, in a first purification stage, low-boiling products and unspecified isomers of the useful product are separated from the product stream virtually without loss of useful product and that, in a second purification stage, the useful product is removed in a stream having a purity of >97% by weight and a further stream having a purity of >92% by weight. A preferred embodiment of the process serves for working up VEA, in which the loss of useful product in the first purification stage is less than 5%, based on that amount of VEA in the feed which is added to the purification stage per unit time.Type: ApplicationFiled: August 13, 2005Publication date: August 14, 2008Applicant: DSM IP ASSETS B.V.Inventors: Juan Herguijuela, Werner Pietzonka, Angela Wildermann, Thomas Wolf
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Patent number: 7368583Abstract: The process for recovery of plant sterols and tocopherols from deodorization distillates formed during chemical or physical refining of vegetable oils consists of the following steps: free fatty acids are removed from the deodorization distillate by vacuum distillation or by continuation solvent saponification, after the removal of free fatty acids, the received material is reacted with an aromatic carboxylic acid anhydride at a temperature of 50-150° C., under reduced pressure, after the treatment with anhydride, tocopherols are removed from the mixture, and crystalline free sterols are recovered from the distillation residue containing sterol esters, di- and triglycerides by transesterification.Type: GrantFiled: July 2, 2002Date of Patent: May 6, 2008Assignee: Bunge Zrt.Inventors: Tibor Czuppon, Zsolt Kemeny, Endrene Kovari, Katalin Recseg
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Patent number: 7354936Abstract: The present invention relates to 2-(4-sulphonylphenyl)pyran-4-one derivatives of general formula processes for their preparation, pharmaceutical compositions containing them, and their medical uses.Type: GrantFiled: September 16, 2002Date of Patent: April 8, 2008Assignee: Almirall AGInventors: Maria Isabel Crespo Crespo, Juan Miguel Jimenez Mayorga, Josep Lluis Matallana Julia, Joan Feixas Gras
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Patent number: 7317038Abstract: To provide a semaphorin inhibitor; a peripheral or central nerve regeneration promoter which contains said semaphorin inhibitor as an active ingredient; and a preventive or remedy for a neuropathic disease and a neurodegenerative disease containing said nerve regeneration promoter, or the like. A low-molecular weight compound, which acts at a concentration of 10 ?g/ml or below to inhibit the growth cone collapse activity of semaphorin such as semaphorin 3A, semaphorin 6C or the like and/or the nerve outgrowth inhibitory activity of semaphorin in a collagen gel and which does not substantially affect cell proliferation, is obtained from the culture of strain SPF-3059 belonging to the genus Penicillium. The low-molecular weight compound with the semaphorin inhibitory activity thus obtained exhibits the in vivo nerve-regeneration promoting action.Type: GrantFiled: August 24, 2006Date of Patent: January 8, 2008Assignee: Dainippon Sumitomo Pharma Co., Ltd.Inventors: Toru Kimura, Kaoru Kikuchi, Kazuo Kumagai, Nobuo Hosotani, Akiyoshi Kishino
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Patent number: 7312232Abstract: The present invention provides an antiproliferative compound having the structural formula wherein X is oxygen, nitrogen or sulfur; Y is selected from the group consisting of oxygen, nitrogen and sulfur wherein when Y is oxygen or nitrogen, n is 1 and when Y is sulfur, n is 0. Also provided is a method for inducing apoptosis in a cell comprising administering a composition comprising a compound having said structural formula.Type: GrantFiled: August 20, 2003Date of Patent: December 25, 2007Assignee: Research Development FoundationInventors: Bob G. Sanders, Kimberly Kline, Laurence Hurley, Robb Gardner, Marla Menchaca, Weiping Yu, Puthucode N. Ramanan, Shenquan Liu, Karen Israel
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Patent number: 7244761Abstract: To provide a semaphorin inhibitor; a peripheral or central nerve regeneration promoter which contains said semaphorin inhibitor as an active ingredient; and a preventive or remedy for a neuropathic disease and a neurodegenerative disease containing said nerve regeneration promoter, or the like. A low-molecular weight compound, which acts at a concentration of 10 ?g/ml or below to inhibit the growth cone collapse activity of semaphorin such as semaphorin 3A, semaphorin 6C or the like and/or the nerve outgrowth inhibitory activity of semaphorin in a collagen gel and which does not substantially affect cell proliferation, is obtained from the culture of strain SPF-3059 belonging to the genus Penicillium. The low-molecular weight compound with the semaphorin inhibitory activity thus obtained exhibits the in vivo nerve-regeneration promoting action.Type: GrantFiled: July 27, 2001Date of Patent: July 17, 2007Assignee: Dainippon Sumitomo Pharma Co., Ltd.Inventors: Toru Kimura, Kaoru Kikuchi, Kazuo Kumagai, Nobuo Hosotani, Akiyoshi Kishino
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Patent number: 7202372Abstract: The invention relates to a process for recovering sterols and/or wax alcohols from a crude tall oil based source material comprising sterols and/or wax alcohols in esterified form and fatty and/or rosin acids and optionally sterols and/or wax alcohols in free form, said method comprising the steps of: a) converting free acids in the source material to corresponding salts, b) removing water if present, c) transesterifying the esterified sterols and/or wax alcohols present in the dry material obtained in step a or step b to liberate sterols and/or wax alcohols, d) evaporative fractionating the transesterified material, and e) isolating sterols and/or wax alcohols from the obtained fraction(s) and/or the residue.Type: GrantFiled: September 6, 2002Date of Patent: April 10, 2007Assignee: Sterol Technologies, Ltd.Inventor: Antti Hamunen
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Patent number: 6867308Abstract: A process for separation of specific tocopherols from a mixture of tocopherols is disclosed. The process includes methods of separation of the tocopherols from residues of vegetable oil refining and other various food sources by dissolving in organic solvents and eluting over non-ionic adsorbent resins.Type: GrantFiled: September 19, 2002Date of Patent: March 15, 2005Assignee: Archer-Daniels-Midland CompanyInventors: Laslow Bartok, Ahmad Hilaly, Christine M. Schuette, Rishi Shukla
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Patent number: 6846941Abstract: Disclosed are processes for separating valuable products, including unsaponifiable materials, from any given matrix of raw materials that is mainly composed of saponifiable components and unsaponifiable components. Preferred methods include converting sodium or potassium soaps obtained from the saponification of a starting material into metallic soaps which have a lower melting point, and when melted, have viscosity sufficiently low to enable processing such as by distillation evaporation processes. Preferred raw materials include animal or vegetable products, as well as by-products, residues, and waste products from the processing of animal or vegetable products, such as from food processing, cellulose processing and the like. Valuable products which may be obtained by the disclosed processes include sterols, vitamins, flavonoids, and tocopherols.Type: GrantFiled: February 20, 2002Date of Patent: January 25, 2005Assignee: Resitec Industria Quimica Ltda.Inventors: Rodolfo Rohr, Raul Rohr, Jose Anibal Trujillo-Quijano
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Patent number: 6838104Abstract: This invention relates to processes for the production of tocotrienol compounds from biological sources such as palm oil, cereals, grains, and grain oils. The tocotrienol products are recovered in high yields. These tocotrienols are useful as pharmaceuticals, in foodstuffs and as dietary supplements. These compositions are hypocholesterolemic, antioxidizing, antithrombotic, antiatherogenic, antiinflammatory and immunoregulatory in nature. Tocotrienols are known to lower the levels of low density lipoproteins in the bloodstream.Type: GrantFiled: December 11, 2001Date of Patent: January 4, 2005Assignee: Archer Daniels Midland CompanyInventor: Lewis Jacobs
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Patent number: 6815551Abstract: A process for concentrating sterols and/or tocopherols from mixtures of fats and fatty derivatives and from residues left after they have been worked up is described. After splitting of the glycerides by hydrolysis and subsequent removal of the free fatty acids by distillation, the tocopherol/sterol esters still present are largely split into free tocopherols/sterols by an additional hydrolysis step.Type: GrantFiled: February 4, 2003Date of Patent: November 9, 2004Assignee: Cognis Deutschland GmbH & Co. KGInventors: Wolfgang Albiez, William G. Kozak, Thorsten Louwen
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Publication number: 20040158083Abstract: A process for the separation and recovery of minor components from vegetable oil such as palm oil. Esterified palm oil is subjected to molecular distillation giving a concentrate rich in minor components. The concentrate is then adsorbed to adsorbents such as normal phase silica gel, reversed phase (particularly C18) silica gel or neutral alumina as well as polymer absorbents such as polyethylene glycol and polyacrylate polyalcohol. Minor components such as squalene, carotenes, tocols and sterols are then selectively desorbed, separated and recovered using solvents operating at isocratic conditions. The desorption of the said minor components are sped up by applying pressure of between 0.2 to 50 bar. By the same method, individual tocols isomers from palm oil can also be separated and recovered.Type: ApplicationFiled: November 25, 2003Publication date: August 12, 2004Inventors: Yuen May Choo, Mei Han Ng, Ah Ngan Ma, Yusof Basiron
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Publication number: 20040138479Abstract: Processes for preparing color-stable, low-impurity tocopherol compositions are described, wherein the processes comprise: (a) providing a protecting group-substituted tocopherol compound, for example an acetate of a natural-source tocopherol compound; (b) purifying the protecting group-substituted tocopherol compound, for example through crystallization; and (c) solvolyzing the purified compound to form free tocopherol. Also described are the tocopherol compositions prepared thereby.Type: ApplicationFiled: July 24, 2003Publication date: July 15, 2004Inventor: Norman Milstein
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Patent number: 6706898Abstract: The invention relates to method for separating tocopherol from a first tocopherol admixture by heating the first tocopherol admixture composed of at least one tocopherol, a fatty acid, and an esterifying compound to esterify the fatty acid to produce a second tocopherol admixture composed of the tocopherol, the esterified fatty acid, and the unesterified fatty acid; distilling the second tocopherol admixture with the esterified fatty acid to remove the unesterified fatty acid from the second tocopherol admixture to produce a third tocopherol admixture composed of the tocopherol, with substantially removed unesterified fatty acid; distilling the third tocopherol admixture for a sufficient time and temperature to substantially remove the tocopherol from the third tocopherol admixture to produce a fourth tocopherol admixture composed of the removed tocopherol and a non-tocol component; and extracting the tocopherol from the fourth tocopherol admixture with an extraction solvent composed of a polar, organic solveType: GrantFiled: July 27, 1999Date of Patent: March 16, 2004Assignee: Archer-Daniels-Midland CompanyInventor: Charles E. Sumner, Jr.
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Publication number: 20040030166Abstract: This invention relates to methods for treating distillates obtained during the process of deodorizing various oils. More particularly, this invention relates to methods for recovering fatty acids, tocopherols, and sterols from a distillate obtained from the deodorizing of various oils.Type: ApplicationFiled: March 18, 2002Publication date: February 12, 2004Inventors: Dick Copeland, W. Maurice Belcher
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Patent number: 6673945Abstract: This invention provides a method of separating tocopherols by using a weakly basic polyvinyl pyridine resin. The resin has the capacity to selectively bind tocopherols, allowing other impurities typically found in a tocopherol production plant stream to separate from the tocopherols. After loading a tocopherol-containing mixture onto a separatory column packed with the resin, the loaded column is eluted with a solvent followed by an alcohol. The eluate is collected in fractions, and the tocopherol-containing fractions are combined and concentrated to yield a purified tocopherol composition. It has been found that the present invention produces highly purified tocopherol compositions (90+%), and is particularly useful for preparing highly purified tocopherol compositions, specifically enriched in &agr;-tocopherol.Type: GrantFiled: November 1, 2002Date of Patent: January 6, 2004Assignee: Archer-Daniels Midland CompanyInventors: Thomas P. Binder, Ahmad K. Hilaly
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Patent number: 6656358Abstract: A method for the chromatographic separation of vitamin E isomers such as &agr;-tocopherol, &bgr;-tocopherol, &ggr;-tocopherol, &dgr;-tocopherol, &agr;-tocotrienol, &bgr;-tocotrienol, &ggr;-tocotrienol and &dgr;-tocotrienol from a vitamin E containing mixture by combining the vitamin E mixture with an adsorbent to effect adsorption of the vitamin E isomers on the adsorbent; and then selectively desorbing the vitamin E isomers from the adsorbent with a solvent under supercritical conditions.Type: GrantFiled: February 2, 2001Date of Patent: December 2, 2003Assignee: Malaysian Palm Oil BoardInventors: Choo Yuen May, Ma Ah Ngan, Yusof Basiron
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Publication number: 20030158429Abstract: The invention relates to a process for isolating sterols and tocopherols from mixtures of fats and fatty derivatives and from residues left after they have been worked up. After splitting of the glycerides by hydrolysis and subsequent removal of the free fatty acids by distillation, the sterol esters still present are largely split into free sterols by an additional hydrolysis step.Type: ApplicationFiled: February 4, 2003Publication date: August 21, 2003Inventors: Wolfgang Albiez, William G. Kozak, Thorsten Louwen
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Publication number: 20030153616Abstract: A process for separation of specific tocopherols from a mixture of tocopherols is disclosed. The process includes methods of separation of the tocopherols from residues of vegetable oil refining and other various food sources by dissolving in organic solvents and eluting over non-ionic adsorbent resins.Type: ApplicationFiled: September 19, 2002Publication date: August 14, 2003Inventors: Laslow Bartok, Ahmad Hilaly, Christine M. Schuette, Rishi Shukla
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Publication number: 20030130526Abstract: This invention provides a method of separating tocopherols by using a weakly basic polyvinyl pyridine resin. The resin has the capacity to selectively bind tocopherols, allowing other impurities typically found in a tocopherol production plant stream to separate from the tocopherols. After loading a tocopherol-containing mixture onto a separatory column packed with the resin, the loaded column is eluted with a solvent followed by an alcohol. The eluate is collected in fractions, and the tocopherol-containing fractions are combined and concentrated to yield a purified tocopherol composition. It has been found that the present invention produces highly purified tocopherol compositions (90+%), and is particularly useful for preparing highly purified tocopherol compositions, specifically enriched in &agr;-tocopherol.Type: ApplicationFiled: November 1, 2002Publication date: July 10, 2003Inventors: Thomas P. Binder, Ahmad K. Hilaly
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Publication number: 20030120095Abstract: Disclosed are processes for separating valuable products, including unsaponifiable materials, from any given matrix of raw materials that is mainly composed of saponifiable components and unsaponifiable components. Preferred methods include converting sodium or potassium soaps obtained from the saponification of a starting material into metallic soaps which have a lower melting point, and when melted, have viscosity sufficiently low to enable processing such as by distillation/evaporation processes. Preferred raw materials include animal or vegetable products, as well as by-products, residues, and waste products from the processing of animal or vegetable products, such as from food processing, cellulose processing and the like. Valuable products which may be obtained by the disclosed processes include sterols, vitamins, flavonoids, and tocopherols.Type: ApplicationFiled: February 20, 2002Publication date: June 26, 2003Inventors: Rodolfo Rohr, Raul Rohr
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Patent number: 6441200Abstract: Disclosed is a method for preparing DL-&agr;-tocopherol through the condensation of isophytol or phytol derivatives and trimethylhydroquinone (TMHQ) using a catalyst system comprising a divalent metal halogen compound, silica gel and/or silica-alumina, and a Brönsted acid. Isophytol or phytol derivatives are slowly added to trimethylhydroquinone for the condensation thereof at 80 to 135° C. over 30 to 60 min in the presence of the metal halogen and the silica gel and/or silica-alumina. In the presence of the Brönsted acid, the intermediates are converted into the product. The silica gel and/or silica-alumina is washed with a polar solvent for recovery. The catalyst system can remarkably reduce side-reactions upon the condensation of isophytol or phytol derivatives and TMHQ, thus producing DL-&agr;-tocopherol with a high purity at a high yield.Type: GrantFiled: November 13, 2000Date of Patent: August 27, 2002Assignee: Sk CorporationInventors: Sijoon Lee, Jeong-Soo Kim, Young-Seek Yoon, Myung-Jun Kim, Jun-Tae Choi, Byong-Sung Kwak
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Patent number: 6429320Abstract: Processes for purifying compounds are disclosed which include reacting (i) a mixture of at least one tocopherol compound or sterol compound, and an alcohol having from about 10 to 30 carbons with (i) one or more boron-containing compounds to form a second mixture of orthoborate esters, wherein the mole ratio of tocopherol, sterol and alcohol to boron is at least about 2.5:1; heating the second mixture to form a residue containing the orthoborate esters; contacting the residue with a compound capable of solvolyzing the orthoborate esters to form a third mixture including the boron-containing compound(s), the alcohol and the tocopherol and/or sterol compound(s); and recovering the tocopherol and/or sterol compound(s).Type: GrantFiled: August 3, 2001Date of Patent: August 6, 2002Assignee: Cognis CorporationInventors: Patrick M. McCurry, Jr., Stephen W. Turner, Carl Pickens
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Patent number: 6410755Abstract: The invention provides a method of producing &agr;-tocopherol and &agr;-tocopheryl esters. The method comprises using a biological system to produce farnesol or geranylgeraniol. Then, the farnesol or geranylgernaiol is chemically converted into &agr;-tocopherol or an &agr;-tocopheryl ester.Type: GrantFiled: July 6, 1999Date of Patent: June 25, 2002Assignee: DCV, Inc.Inventors: James R. Millis, Gabriel G. Saucy, Julie Maurina-Brunker, Thomas W. McMullin
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Patent number: 6410752Abstract: An object of the present invention is to provide the tocopherol derivatives represented by the following formula (I), and their salts: Wherein, R1, R2 and R3 are H or methyl group, and at least one positions selected from group consisting of the R1, R2 and R3 positions are methyl group; and, A is CH2—CH(CH3)— or CH═C(CH3)— The other object of the present invention is to provide a method for preparing the above tocopherol derivatives. The tocopherol derivatives is prepared by reacting tocopherol with phosphorous oxychloride in an equivalent ratio of 1:1˜1.3, in presence of an organic base, in an organic solvent; reacting the tocopherol dichlorophosphate produced by the above reaction with 3-aminopropanol in presence of an organic base, in an organic solvent; and, hydrolyzing the above products.Type: GrantFiled: January 9, 2001Date of Patent: June 25, 2002Assignee: Pacific CorporationInventors: Kil Joong Kim, Duck Hee Kim, Ho Sik Rho, Jae Won You, Chun Ja Nam, Jong Eoun Hong, Hak Hee Kang, Ih Seob Chang
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Publication number: 20020072620Abstract: Processes for purifying compounds are disclosed which include reacting (i) a mixture of at least one tocopherol compound or sterol compound, and an alcohol having from about 10 to 30 carbons with (ii) one or more boron-containing compounds to form a second mixture of orthoborate esters, wherein the mole ratio of tocopherol, sterol and alcohol to boron is at least about 2.5:1; heating the second mixture to form a residue containing the orthoborate esters; contacting the residue with a compound capable of solvolyzing the orthoborate esters to form a third mixture including the boron-containing compound(s), the alcohol and the tocopherol and/or sterol compound(s); and recovering the tocopherol and/or sterol compound(s).Type: ApplicationFiled: August 3, 2001Publication date: June 13, 2002Inventors: Patrick M. McCurry, Stephen W. Turner, Carl Pickens, Jan R. Varvil
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Patent number: 6403811Abstract: A process for recovering a concentrate of chromans from a distillate containing chromans is provided comprising the steps of: (1) forming chroman phosphates in the distillate; (2) subjecting the distillate to shearing forces, in the presence of a gas of flotation to form a froth; and (3) recovering the froth containing the concentrate of chroman phosphates.Type: GrantFiled: July 25, 2001Date of Patent: June 11, 2002Assignee: Swig Pty LtdInventor: Simon Michael West