Processes Of Isolating, Purifying Or Recovering From Animal, Vegetable Or Fungal Sources (e.g., Wool Fat Or Grease, Lanolin, Fish Oils, Animal Tissue, Soybean Oil, Tall Oil Or Pitch, Wood Products, Sugar Cane, Soap Stocks, Yeast, Molds, Etc.) Patents (Class 552/545)
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Patent number: 12049593Abstract: A process for producing crude biodiesel from renewable feedstocks (such as fats, oils, and greases) containing unsaponifiable materials; purifying the crude biodiesel through a purification process; recovering a purified biodiesel distillate stream and a less volatile biodiesel residue stream; and further recovering valuable chemicals from the biodiesel residue. Specifically, the present technology relates to the concentration of valuable chemicals in the biodiesel residue product of biodiesel production and the subsequent recovery of these valuable chemicals. The process may further include the conversion of the biodiesel residue into diesel range hydrocarbons using hydrodeoxygenation and the subsequent purification of the hydrocarbon fraction produced thereby.Type: GrantFiled: July 30, 2021Date of Patent: July 30, 2024Assignee: Renewable Energy Group, Inc.Inventors: James Matthew White, David A. Slade, Martin R. Haverly, Cody J. Ellens
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Patent number: 11781088Abstract: The presently claimed invention relates to a process for the production and purification of sterols from oil distillates or oil distillation residues, in particular from the latter. Specifically, the presently claimed invention relates to a process for obtaining sterols in a pure form with reduced impurity and improved color.Type: GrantFiled: September 24, 2020Date of Patent: October 10, 2023Assignees: BASF SE, BASF HEALTH AND CARE PRODUCTS FRANCE S.A.S.Inventors: Valerie Eychenne, Yannick Basso, Olivier Vallejo, Joerg Schwarzer
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Patent number: 11718640Abstract: The present invention discloses an improved process for extracting cholesterol in high yield and purity from fish oil waste residue. The so obtained cholesterol of pharmaceutical grade is useful as a precursor for the preparation of vitamin D3.Type: GrantFiled: September 12, 2018Date of Patent: August 8, 2023Assignee: FERMENTA BIOTECH LIMITEDInventors: Anupama Datla, Prashant Nagre, Jagdish Tamore, Sreenath Trivikram, Gajanan Degaonkar
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Patent number: 11549081Abstract: Provided are methods to destabilize emulsion feedstocks. In the methods, a moderate temperature is applied to the feedstock to create a first mixture. The moderate temperature may be between 120 and 220 degrees Celsius. The first mixture is mixed at the moderate temperature, such as by staged mixing in some embodiments. Moreover, the first mixture is retained at the moderate temperature for up to six hours. The first mixture is separated into an oil phase, convoluted phase, and a water phase. In some embodiments, the moderate temperature may be 125 to 150 degrees Celsius, such as between 125 and 130 degrees Celsius. Moreover, the first mixture may be retained at the moderate temperature for between forty-five minutes and four hours, such as from two to four hours. The separation may occur at the moderate temperature.Type: GrantFiled: April 5, 2017Date of Patent: January 10, 2023Assignee: RRIP, LLCInventors: Mohan Prasad A. Dasari, Hugh Tallant Warren
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Patent number: 11097981Abstract: Disclosed are asphalt binder compositions and methods for making such compositions with pure sterol:crude sterol blends. The sterol blends improve various rheological properties.Type: GrantFiled: May 29, 2020Date of Patent: August 24, 2021Assignees: A.L.M. Holding Company, Ergon Asphalt & Emulsions, Inc.Inventors: Gerald H. Reinke, Gaylon L. Baumgardner, Andrew Hanz
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Patent number: 10711031Abstract: A method for extracting phytosterols from tall oil pitch. The method involves saponifying tall oil pitch using an alkali in a polyatomic alcohol, extracting unsaponified matter from the alkali-alcohol solution using a hydrocarbon solvent, subsequently removing the solvent by distillation, and concentrating the phytosterols, wherein a mixture of paraffin hydrocarbons is used as said hydrocarbon solvent, and, following extraction from the extraction solution, betulin is isolated by crystallization and the phytosterols are then concentrated by means of rectification. This method enables an increase in the extraction rate of phytosterols from a saponified tall oil pitch up to 95%, producing the end product with phytosterol content of at least 65% with unwanted betulin impurities at no more than 0.3%.Type: GrantFiled: May 8, 2018Date of Patent: July 14, 2020Assignee: ORGKHIM BCH MANAGEMENT COMPANY, JSCInventors: Ilia Nikolaevich Chernov, Alexey Olegovich Korshunov, Taras Ivanovich Dolinskiy, Mikhail Alekseevich Lazarev, Ekaterina Aleksandrovna Mavrina, Ilia Sergeevich Ilichev, Arkadiy Benyuminovich Radbil
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Patent number: 10214705Abstract: A method is provided for processing an organic oil in steps, including the following: A) providing a raw oil; B) degumming the raw oil by adding water or acid to the raw oil and forming at least two phases, an aqueous phase and an oil phase, and separating the aqueous phase enriched in phospholipid from the oil phase; C) adding sodium hydrogencarbonate and/or sodium acetate to the oil phase from step B, and removing alkaline-earth compounds and/or phospholipids and/or stearyl glycosides, in solution or suspension in an aqueous phase, from the oil phase.Type: GrantFiled: June 3, 2015Date of Patent: February 26, 2019Assignee: GEA Westfalia Separator Group GmbHInventors: Steffen Hruschka, Wladislawa Boszulak
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Patent number: 9909084Abstract: The present invention relates to an extraction process of an unsaponifiable fraction contained in an oil or a vegetable butter, in an oil originating from a micro-organism, in a concentrate of oil or butter or of oil originating from a micro-organism, or in a co-product of the refining industry for vegetable oils, such as deodorization exhaust and distillates of physical refining, or oils originating from micro-organisms, comprising at least: A) a transformation step of said oils, of said butter or said co-product of the refining industry for vegetable oils or oils originating from micro-organisms in hydro-alcoholic solution, especially via a saponification step, and B) an extraction step of the hydro-alcoholic solution in which the fatty fraction is separated from unsaponifiable fraction by liquid/liquid extraction, said process being characterized in that at least the liquid/liquid extraction step of the step B is performed by using a first solvent system comprising a solvent content selected from the sType: GrantFiled: July 30, 2012Date of Patent: March 6, 2018Assignee: Laboratoires ExpanscienceInventors: Eglantine Mercier, Jacques Legrand, Alex Saunois
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Patent number: 9884837Abstract: 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: GrantFiled: November 2, 2011Date of Patent: February 6, 2018Assignee: VERBIO VEREINIGTE BIOENERGIE AGInventors: Joachim Lemp, Nico Baade, Emanuel Pöhls
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Patent number: 9422507Abstract: A process for recovering fatty acids, resin acids and sterols from tall oil pitch, said process comprising a) saponifying the tall oil pitch with an alkali to hydrolyze esters included in the pitch to free alcohols and organic acids in salt form, b) acidulating the saponified pitch with a mineral acid to convert the organic acids in salt form into free organic acids and to form an organic phase and an aqueous phase, c) separating the aqueous phase from the organic phase, d) evaporation fractionating the organic phase to obtain a distillate rich in sterols, fatty acids and resin acids, d) evaporation fractionating the organic phase to obtain a distillate rich in sterols, fatty acids and resin acids, e) evaporation fractionating the distillate to obtain a bottom fraction rich in sterols, and a distillate rich in fatty acids and resin acids, and f) subjecting the sterols in the sterol-rich bottom fraction to crystallization purification.Type: GrantFiled: May 1, 2013Date of Patent: August 23, 2016Assignee: RAVINTORAISIO OYInventor: Antti Hamunen
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Patent number: 9221869Abstract: There is disclosed a method for isolation and purification of phytosterols from tall oil pitch comprising the steps of: a) contacting the tall oil pitch with a solvent to form a tall oil solvent mixture; b) separating the tall oil pitch solvent mixture in at least two separate streams wherein one process stream is enriched in acidic pitch components and a second stream enriched in free- and bound sterols in the form of steryl esters; c) subjecting the stream enriched in free- and steryl esters to treatment with an alcohol under transesterification conditions wherein a reaction mixture is formed and sterols comprising the steryl esters are liberated as free sterols; and d) separating the free sterols from the reaction mixture of step c) by crystallization and extraction with one or more solvents. There are disclosed free fatty acids and resin acids separated from the tall oil pitch. Moreover, there is disclosed a manufacture and separation of fatty acid alkyl esters by the method.Type: GrantFiled: February 10, 2009Date of Patent: December 29, 2015Assignee: SUNPINE ABInventors: Lars Stigsson, Valeri Naydenov
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Publication number: 20150099871Abstract: A method of extracting lentinan from lentinan containing mushrooms comprising the step of contacting the mushrooms with an ionic liquid so as to obtain a lentinan rich ionic liquid solution.Type: ApplicationFiled: March 22, 2013Publication date: April 9, 2015Inventors: Martyn Earle, Manuela Gilea
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Patent number: 8524928Abstract: The invention relates to an effective process for producing plant stanol by hydrogenating plant sterol in an organic solvent at a hydrogen pressure of 1-200 bar in the presence of a hydrogenation catalyst.Type: GrantFiled: July 24, 2009Date of Patent: September 3, 2013Assignee: Raisio Nutrition Ltd.Inventors: Jari Ekblom, Antti Hamunen, Rami Hartonen, Marko Hirvijärvi, Juha Holma, Juha Orte
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Patent number: 8450453Abstract: The invention relates to a process for recovering fatty acids, resin acids and sterols from tall oil pitch, said process comprising a) saponifying the tall oil pitch with an alkali to hydrolyse esters included in the pitch to free alcohols and organic acids in salt form, b) acidulating the saponified pitch with a mineral acid to convert the organic acids in salt form into free organic acids and to form an organic phase and an aqueous phase, c) separating the aqueous phase from the organic phase, d) evaporation fractionating the organic phase to obtain a distillate rich in sterols, fatty acids and resin acids, e) evaporation fractionating the distillate to obtain a bottom fraction rich in sterols, and a distillate rich in fatty acids and resin acids, and f) subjecting the sterols in the sterol-rich bottom fraction to crystallization purification.Type: GrantFiled: February 15, 2008Date of Patent: May 28, 2013Assignee: Ravintoraisio OYInventor: Antti Hamunen
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Patent number: 8318962Abstract: A process of obtaining sterols suitable for human consumption from a crude wood pulping source containing sterol esters is disclosed. The sterols are obtained at high yield and purity. In particular, a process of obtaining sterols at high yield and purity from tall oil pitch (TOP) is disclosed. The sterols obtained can be esterified to sterol esters for use in dietary supplements and as additives for food and beverage products.Type: GrantFiled: December 20, 2007Date of Patent: November 27, 2012Assignee: Cognis IP Management GmbHInventors: Sang I. Kang, Joseph J. Falatek, Brian P. Thiesen, Kenneth R. Bicknell
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Patent number: 8114447Abstract: The present invention relates to the use of “green” or relatively benign solvents such as ethanol, ethanol/water, isopropyl alcohol, isopropyl alcohol/water, ethyl lactate, acetone, butanol, isoamyl alcohol, or ethyl acetate to extract phytosterols from wet corn fiber. The resulting oil product contains free phytosterols and free fatty acids.Type: GrantFiled: April 14, 2008Date of Patent: February 14, 2012Assignee: Archer Daniels Midland CompanyInventors: Charles Abbas, Anne M. Rammelsberg, Kyle Beery
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Publication number: 20120004592Abstract: Tissue solubilizing compositions are provided. The compositions comprise 3-(decyl dimethyl ammonio) propane sulfonate and polyethylene glycol dodecyl ether, such as tetraethylene glycol dodecyl ether. The compositions may be useful to solubilize tissue, including skin, mucosal membrane, and other tissue. The compositions may be further useful to preserve and recover analytes contained within the solubilized skin, mucosal membrane, and other tissue.Type: ApplicationFiled: April 27, 2011Publication date: January 5, 2012Applicant: The Regents of the University of CaliforniaInventors: Samir Mitragotri, Sumit Pallwal, Makoto Ogura, Russell M. Lebovitz
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Publication number: 20110207952Abstract: A process for producing vegan vitamin D3 from an algal waste processing stream by saponifying the waste stream to separate out and removing unsaponifiable cholesterol and converting it to vitamin D3 by ultraviolet irradiation, while precipitating out the saponified fatty acids, triglycerides and polysaccharides.Type: ApplicationFiled: February 15, 2011Publication date: August 25, 2011Inventor: RAFAEL AVILA
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Publication number: 20110098493Abstract: The present invention provides a method of separating ergosterol from a solution containing ergosterol in water-insoluble organic solvent, comprising supplying water to the solution and precipitating ergosterol. According to the method of the present invention, ergosterol crystals can be obtained at a high yield. Moreover, controlled water supply provides granular ergosterol aggregates exhibiting good solid-liquid separation character at a high yield.Type: ApplicationFiled: December 23, 2010Publication date: April 28, 2011Applicant: KANEKA CORPORATIONInventor: Hideo Kawachi
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Patent number: 7884221Abstract: The present invention provides a method of separating ergosterol from a solution containing ergosterol in water-insoluble organic solvent, comprising supplying water to the solution and precipitating ergosterol. According to the method of the present invention, ergosterol crystals can be obtained at a high yield. Moreover, controlled water supply provides granular ergosterol aggregates exhibiting good solid-liquid separation character at a high yield.Type: GrantFiled: November 7, 2003Date of Patent: February 8, 2011Assignee: Kaneka CorporationInventor: Hideo Kawachi
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Publication number: 20100305342Abstract: A method of preparing phytosterols from tall oil pitch containing steryl esters comprises the steps of converting the steryl esters to free phytosterols while in the pitch to produce a modified pitch containing the free phytosterols; removing light ends from the modified pitch by evaporation to produce a bottom fraction containing the free phytosterols; evaporating the bottom fraction to produce a light phase distillate containing the free phytosterols; dissolving the light phase distillate in a solvent comprising an alcohol to produce a solution containing the free phytosterols; cooling the solution to produce a slurry with the free phytosterols crystallized in the slurry; and, washing and filtering the slurry to isolate the crystallized phytosterols.Type: ApplicationFiled: August 4, 2010Publication date: December 2, 2010Inventors: Alfred Wong, Hugh Sven Oscar Norman, Angus Kirke MacMillan
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Patent number: 7632530Abstract: The present invention provides an isolation process of the pure sterols from the SODD by simple acid catalyzed esterification and the separation of the reagents by distillation and water washing followed by the crystallization of phytosterols and purification. Soybean oil deodorizer distillate (SODD) and distillate from other vegetable oil refining contain free sterols, in addition to steryl esters, tocopherols squalene and unknown compounds. The process is also applicable to other vegetable oil distillate containing more than 1% phytosterols in the free form. Phytosterols thus obtained is of high purity (95-99%) and high yield (80-90%) and contains ?-sitosterol, Stigmasterol and campesterol.Type: GrantFiled: March 13, 2006Date of Patent: December 15, 2009Assignee: Council of Scientific and Industrial ResearchInventors: Chami Arumughan, Das Retna Sobankumar, Andikkannu Sudaresan, Sreeja Sadasivan Nair, Kannan Yohesh, Leelavathy Rajam
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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: 20090131697Abstract: A method of preparing phytosterols from tall oil pitch containing steryl esters comprises the steps of converting the steryl esters to free phytosterols while in the pitch to produce a modified pitch containing the free phytosterols; removing light ends from the modified pitch by evaporation to produce a bottom fraction containing the free phytosterols; evaporating the bottom fraction to produce a light phase distillate containing the free phytosterols; dissolving the light phase distillate in a solvent comprising an alcohol to produce a solution containing the free phytosterols; cooling the solution to produce a slurry with the free phytosterols crystallized in the slurry; and, washing and filtering the slurry to isolate the crystallized phytosterols.Type: ApplicationFiled: September 18, 2008Publication date: May 21, 2009Inventors: Alfred Wong, Hugh Sven Oscar Norman, Angus Kirke MacMillan
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Publication number: 20080262251Abstract: A process for recovering sterols from organic material containing sterols and sterol derivatives. In a first step (a) the organic material is reacted with at least one of polyols, polyamines, alkanolamines or monohydric alcohols to increase the amount of free sterols in the organic material; (b) reacting residual reactants, and their esters or amides with epoxydated components; and (c) separating the free sterols from the mixture by short path distillation, thin film evaporation, or flash evaporation. The recovered sterols can be further purified by a crystallization step.Type: ApplicationFiled: May 31, 2004Publication date: October 23, 2008Inventors: Setsuo Sato, Wolfgang Albiez, Alexssander S. Araujo, Wanderson Bueno De Almeida
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Publication number: 20080207931Abstract: Provided is a method for selective extraction of steroid compounds using entrapped ?-cyclodextrin polymers. Particularly, steroid hormones can be effectively selected from a biological sample by selectively extracting steroid compounds using entrapped ?-cyclodextrin polymers, prepared by adding epichlorohydrin to ?-cyclodextrin to prepare a polymer in a gel state, entrapping the polymer and pulverizing the products without using an additional device required in conventional solid-phase extraction.Type: ApplicationFiled: November 29, 2007Publication date: August 28, 2008Inventors: Man Ho Choi, Dong Hyun Kim, Bong Chul Chung, Ju-Yeon Moon
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Patent number: 7371876Abstract: The present invention describes a method for separating sterols from neutral substances comprising the sterols. The method generally starts with extracting a hydrocarbon fraction from neutral substances. The hydrocarbon fraction may be optionally washed with water. The neutral substances are separated from the hydrocarbon. The hydrocarbon fraction or the neutral substances are subjected to evaporation fractionating to obtain a sterol-rich fraction. The sterol-rich fraction is dissolved in a solvent, and the sterols are crystallized from the solvent. The obtained sterol crystals are separated from the solvent.Type: GrantFiled: September 1, 2004Date of Patent: May 13, 2008Assignee: Sterol Technologies Ltd.Inventors: Antti Hamunen, Keijo Ukkonen
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Patent number: 7368138Abstract: The present invention relates to the use of “green” or relatively benign solvents such as ethanol, ethanol/water, isopropyl alcohol, isopropyl alcohol/water, ethyl lactate, acetone, butanol, isoamyl alcohol, or ethyl acetate to extract phytosterols from wet corn fiber. The resulting oil product contains free phytosterols and free fatty acids.Type: GrantFiled: March 21, 2003Date of Patent: May 6, 2008Assignee: Archer-Daniels-Midland CompanyInventors: Charles Abbas, Anne M. Rammelsberg, Kyle Beery
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Patent number: 7244856Abstract: Processes for recovering phytosterols are described. The processes comprise: (a) providing a liquid mixture containing a phytosterol, methanol, and one or more additional compounds, wherein the methanol is present in an amount of from 25 to 75% by weight, based on the phytosterol; (b) cooling the mixture to form phytosterol crystals; and (c) separating the phytosterol crystals from the remainder of the mixture.Type: GrantFiled: July 22, 2004Date of Patent: July 17, 2007Assignee: Cognis Deutschland GmbH & Co. KGInventors: Christophe Sicre, Rene Armengaud, Joerg Schwarzer, Bernhard Gutsche, Markus Musholt, Volkmar Jordan
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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: 7173144Abstract: The present invention provides a method of obtaining highly pure phytosterols practically and efficiently from crude phytosterol compositions derived from vegetable fats and oils. That is, the present invention provides a method of saponifying fatty esters contained in crude phytosterol compositions with an alkali in a mixed solvent of an lower alcohol and water, as well as a process for producing phytosterols, which comprises, after this saponifying method, cooling the reaction solution to precipitate crystals of phytosterols, and separating the obtained crystals.Type: GrantFiled: November 2, 2000Date of Patent: February 6, 2007Assignee: Kao CorporationInventors: Yasuyuki Hattori, Masamitsu Horio, Jun Kono
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Patent number: 7078544Abstract: A process for producing steryl or stanyl esters, comprises the steps of: a) forming a reacting mixture by contacting a lipase with a reactant mixture wherein the reactant mixture comprise sterols or stanols and one or more esters selected from the group consisting of esters of a fatty acid with a short chain aliphatic alcohol; b) separating the lipase from the reacting mixture to form a reacted mixture; and c) separating steryl or stanyl esters from the reacted mixture. The reaction is carried out in stirred reactors at pressures below atmospheric pressure and temperatures from 30 to 90° C. The separation of esters from the reacted mixtures is carried out by distillation at low pressures. A process for esterifying sterols or stanols comprise forming a reacting mixture by contacting a lipase with a reactant mixture wherein the reactant mixture comprise sterols or stanols and one or more esters selected from the group consisting of esters of a fatty acid with a short chain aliphatic alcohol.Type: GrantFiled: July 26, 2002Date of Patent: July 18, 2006Assignee: Harting, S.A.Inventors: Miguel Angel Fuenzalida Diaz, Alejandro Markovits Rojas, Endre Markovits Schersl, Irene Martinez Basterrechea
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Patent number: 7037548Abstract: The purpose of the present invention is to extract oil from the soybean material containing soybean germ as a main component, and to utilize it. The present invention relates to a method for producing a soybean material, comprising crudely crushing selected soybeans into a size of less than ½, and separating and concentrating a soybean germ fraction by means of sieving, sorting with air, separation based on the grain shape and the like, to the soybean germ fraction produced by said method, to oil prepared from the soybean material containing soybean germ as a main component, to oil containing 0.8% by weight or more of sterols' content, and to foods containing said oil.Type: GrantFiled: May 25, 2004Date of Patent: May 2, 2006Assignee: Ajinomoto Co., Inc.Inventors: Yoichi Ozawa, Akihiro Nakatani, Hitoshi Sato, Osamu Mori, Yukio Akiyama, Yasushi Morinaga, Yuji Nakata
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Patent number: 6979743Abstract: Processes for preparing substantially citrostadienol-free phytosterols are disclosed. The processes described include dissolving a liquid phytosterol in a hydrocarbon solvent, optionally with added methanol, and crystallizing the phytosterol compounds. Also described are the resulting phytosterols which are substantially citrostadienol-free, and preferably contain less than 0.5% by weight citrostadienol.Type: GrantFiled: February 4, 2000Date of Patent: December 27, 2005Assignee: Cognis Deutschland GmbH & Co. KGInventors: Joerg Schwarzer, Bernhard Gutsche
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Patent number: 6956125Abstract: The invention relates to a process for the production of sterols from fatty acid distillation residues, characterized in that the partial glycerides are subjected to a first transesterification step under mild conditions and, after working up and the removal of impurities, the sterol esters are subjected to a second transesterification step under more extreme conditions.Type: GrantFiled: August 7, 2001Date of Patent: October 18, 2005Assignee: Cognis Deutschland GmbH & Co. KGInventors: Gerhard Wollmann, Joerg Schwarzer, Bernhard Gutsche
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Patent number: 6844456Abstract: The present invention is directed to modified, hydroxy-bearing aromatic ring structures having cytoprotective activity. More specifically, in a first embodiment the present invention is directed to phenolic compounds, and in particular steriods (e.g., estrogens), wherein a non-fused polycyclic, hydrophobic substituent is attached to the hydroxy-substituted A-ring thereof. The present invention is further directed to a process for conferring cytoprotection to a population of cells involving the administration of the compound.Type: GrantFiled: November 5, 2001Date of Patent: January 18, 2005Assignee: Washington UniversityInventor: Douglas F. Covey
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Patent number: 6815553Abstract: The invention provides methods for separating outer birch bark from inner birch bark. The invention also provides methods for isolating betulin; lupeol; betulinic acid; 9,10-epoxy-18-hydroxyoctadecanoic acid; 9,10,18-trihydroxyoctadecanoic acid; polyphenolic polymers and fatty acids from birch bark.Type: GrantFiled: February 6, 2002Date of Patent: November 9, 2004Assignee: Regents of the University of MinnesotaInventors: Pavel A. Krasutsky, Robert M. Carlson, Vitaliy V. Nesterenko, Igor V. Kolomitsyn, Chris F. Edwardson
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Patent number: 6800317Abstract: This invention relates to phytosterols and phytostanols, in particular to fatty acid esters of phytosterols and phytostanols with a specified fatty acid composition. The invention further relates to methods for preparation of the phytosterol and phytostanol esters and their uses.Type: GrantFiled: May 16, 2003Date of Patent: October 5, 2004Assignee: Raisio Benecol OyInventors: Ingmar Wester, Jari Ekblom
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Patent number: 6770767Abstract: A method for separating neutral substances from a soap containing the neutral substances, the method including the steps of: providing a mixture containing (1) the soap containing the neutral substances, (2) water optionally containing sodium sulfate and (3) a C1-C10 hydrocarbon solvent, and heating the mixture to a temperature of at least 140° C., to obtain a soap phase and a hydrocarbon phase containing the neutral substances, the heating step being conducted in a closed system under pressure, wherein the pressure in the system is at least equal to the vapor pressure of the mixture at the temperature used in the heating step; separating the hydrocarbon phase from the soap phase; and optionally separating the neutral substances from the hydrocarbon phase.Type: GrantFiled: December 11, 2001Date of Patent: August 3, 2004Assignee: Sterol Techologies Ltd.Inventor: Antti Hamunen
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Patent number: 6762312Abstract: The present invention provides a process for producing a highly pure phytosterol, at high yield in particular, by an easy treatment from a crude fatty acid ester derived from a vegetable fat and/or oil. That is, the present invention provides a process for producing phytosterol, which comprises (A) bringing a crude fatty acid product derived from a vegetable fat and/or oil including phytosterol into contact with a mixed solvent of an organic solvent and water to crystallize the phytosterol and separating the crystals from the mixed solvent; or (B) mixing a crude fatty acid ester derived from a vegetable fat and/or oil including the phytosterol and a fatty acid ester with a lower alcohol, allowing the mixture to stand at a temperature of 1 to 40° C. to precipitate crystals including the fatty acid ester and separating the crystals to take the lower alcohol solution including the phytosterol.Type: GrantFiled: May 3, 2002Date of Patent: July 13, 2004Assignee: Kao CorporationInventors: Yasuyuki Hattori, Jun Kono, Masamitsu Horio
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Patent number: 6713466Abstract: A food additive useful for lowering serum cholesterol in humans contains a sterol or stanol ester of a fatty acid or a dicarboxylic acid ester of a sterol or stanol made by reacting a sterol, stanol and a carboxylic acid in the presence of an effective amount of a catalyst selected from the group consisting of calcium oxide, calcium hydroxide, a calcium salt of a carboxylic acid, magnesium hydroxide and combinations thereof described herein below.Type: GrantFiled: April 19, 2002Date of Patent: March 30, 2004Assignee: Cognis CorporationInventors: Norman Milstein, Manfred Biermann, Peter Leidl, Rainer von Kries
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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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Publication number: 20030144536Abstract: A process for isolating and purifying phytosterols and phytostanols from tall oil pitch is disclosed which comprises the following steps:Type: ApplicationFiled: January 28, 2002Publication date: July 31, 2003Applicant: Forbes Medi-Tech Inc.Inventors: William E. Sonnier, Michael E. Schultz
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Publication number: 20030139616Abstract: It is intended to find an efficient method of searching for drugs affecting the cholesteryl ester cycle and establish a system of efficiently searching for defoaming agents or regression agents artherosclerotic lesion and a system of searching for therapeutic agents remedies for atherosclerosis with a mechanism different from publicly known ones.Type: ApplicationFiled: October 22, 2002Publication date: July 24, 2003Inventors: Ryuichi Tozawa, Hiromitsu Fuse, Shunbun Kita, Masahira Nakamura
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Patent number: 6589760Abstract: The invention provides a method of separating from corn fiber a lipid fraction having phytosterol esters and phytosterols where the method has the steps of: (a) heating an aqueous mixture of unground corn fiber; (b) contacting the mixture of step (a) with at least one enzyme suitable for digesting starch for a time and at a temperature suitable to provide a mixture of an essentially destarched corn fiber and a liquid comprising soluble carbohydrates; (c) contacting the mixture of step (a) or (b) with a protease enzyme to provide a proteolyzed corn fiber and a liquid; (d) separating the liquid of step (c) from the corn fiber to provide a destarched, proteolyzed corn fiber; and (e) extracting the destarched, proteolyzed corn fiber with at least one organic solvent. A corn fiber lipid fraction/organic solvent solution having phytosterol esters and phytosterols is provided.Type: GrantFiled: February 10, 2000Date of Patent: July 8, 2003Assignee: Eastman Chemical CompanyInventors: Charles M. Buchanan, Norma L. Buchanan, John S. Debenham, Michael C. Shelton, Matthew D. Wood
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Publication number: 20020192732Abstract: Disclosed is a method for quantifying cholesterol in HDL, which does not require complex fragmentation and separation operations, and by which the HDL cholesterol in test samples containing HDL and other lipoproteins such as low density lipoprotein (LDL), very low density lipoprotein (VLDL) and chylomicron (CM) may be quantified selectively, simply and accurately. The method for quantifying cholesterol in high density lipoprotein comprises a first step of erasing cholesterol in lipoproteins other than high density lipoprotein in a test sample, and a second step of adding a surfactant which specifically acts on high density lipoprotein to the product of the first step and enzymatically quantifying cholesterol in high density lipoprotein.Type: ApplicationFiled: July 9, 2002Publication date: December 19, 2002Applicant: Denka Seiken Co., Ltd.Inventors: Hiroshi Matsui, Yasuki Ito, Shuichi Ohara, Akira Fujiwara
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Publication number: 20020183530Abstract: The invention relates to a method of purifying phytosterol concentrates by contacting the phytosterol concentrate with a pressurized fluid. The invention also relates to the obtained purified phytosterol concentrate, foodstuff and animal feed premixes containing the same as well as to foodstuffs and animal feeds containing phytosterol concentrate.Type: ApplicationFiled: January 4, 2002Publication date: December 5, 2002Applicant: DANISCO SUGAR OYInventors: Olli Aaltonen, Sampsa Haarasilta, Pekka Piiroinen, Markku Rantakyla, Jouko Virtanen, Antti Kaipainen
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Publication number: 20020160990Abstract: The present invention relates to a phytosterol and/or a phytostanol ester compound produced from the reaction of a phytosterol and/or a phytostanol with a polyunsaturated fatty acid (PUFA), wherein the polyunsaturated fatty acid has from 18 to 22 carbon atoms and at least three carbon-carbon double bonds. Processes for producing and compositions and a process for using such compositions are also provided.Type: ApplicationFiled: November 23, 1999Publication date: October 31, 2002Inventors: DAVID CARL BURDICK, GERARD MOINE, DANIEL RAEDERSTORFF, PETER WEBER
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Patent number: 6465665Abstract: A high efficiency continuous process for the recovering high purity sterol mixtures from mixtures of neutral compounds obtained form black liquor soap skimings of the cellulose pulping industry or from tall oil pitch comprising the steps of distillation, crystallization and recirculation of the mother liquor residue.Type: GrantFiled: September 1, 2000Date of Patent: October 15, 2002Inventor: Endre Markovits Schersl
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Patent number: 6462210Abstract: The present invention relates to a fractionation process of the unsaponifiable material derived from black-liquor soaps of the cellulose industry. Through this procedure fractions that essentially contain free sterols, fatty alcohols, sterol esters and fatty alcohol esters respectively are separated. Fractions containing sterols or fatty alcohols can be used as such in the alimentary, cosmetic and pharmaceutical industries or they can be used as raw materials for transforming into other useful products.Type: GrantFiled: April 16, 1999Date of Patent: October 8, 2002Assignee: Harting, S.A.Inventors: Miguel Angel Fuenzalida Diaz, Alejandro Markovits Rojas