Glycerol Patents (Class 554/173)
-
Patent number: 12252663Abstract: The present disclosure is related to an apparatus and method for purification of biological feedstock, such as reducing or removing nitrogen containing compounds therein. The method can include subjecting the feedstock to a first separation step for obtaining a first fraction containing free fatty acids and nitrogen containing compounds, and collecting the residue containing acylglycerols. The first fraction is reacted with glycerol to obtain acylglycerols from the free fatty acid therein. This fraction is subjected to a second separation step for obtaining a second fraction containing nitrogen containing compounds, which is discharged as waste-product. The remains from the second separation contain formed acylglycerols and are collected.Type: GrantFiled: August 31, 2020Date of Patent: March 18, 2025Assignee: NESTE OYJInventor: Olli Visuri
-
Patent number: 11013715Abstract: Disclosed herein are compositions, having nanosized droplets, wherein the nanosized droplets may contain a cannabinoid oil, a dietically acceptable carrier oil, a surfactant, and water. Also disclosed herein are methods of making and using the same.Type: GrantFiled: November 30, 2018Date of Patent: May 25, 2021Assignee: Vertosa, Inc.Inventor: Chunxiao Han
-
Patent number: 10138200Abstract: The present invention relates to a process for preparing polyols. In particular, the present invention relates to the preparation, in a single step, of polyols by a process involving a hydrohydroxymethylation reaction starting from a composition A comprising one or more compounds of formula (I).Type: GrantFiled: June 15, 2016Date of Patent: November 27, 2018Assignees: Pivert S.A.S., Centre National De La Recherche Scientifique (CNRS), Universite D'ArtoisInventors: Frederic Hapiot, Eric Monflier, Theodore Vanbesien
-
Patent number: 9776951Abstract: The invention relates to novel polyglycerol esters with a particular oligomer distribution of the polyglycerol present, and to their use in particular in cosmetic formulations as, for example, emulsifier.Type: GrantFiled: February 11, 2015Date of Patent: October 3, 2017Assignee: Evonik Degussa GmbHInventors: Achim Friedrich, Jürgen Meyer, Jan Marian von Hof, Oliver Springer, Peter Muss
-
Patent number: 9332771Abstract: Disclosed are human milk fat (HMF) substitutes, processes for preparation thereof, uses thereof, and fat blends and infant formula containing the HMF substitutes. A fat base composition of the invention includes a mixture of vegetable-derived triglycerides, with less than 50% of the fatty acid residues bonded at the sn-2 position being saturated; and/or with the amount of saturated fatty acid residues bonded at the sn-2 position of the glycerol backbone less than about 43.5% of the total amount of the fatty acid residues. Typically, substantially all of the saturated fatty acids bonded at the sn-2 position of the glycerol backbone are palmitic acid residues. Also disclosed are substitute HMF compositions including a blend of at least 25% or at least 30% of the fat base composition of the invention with up to 75%, or respectively up to 70%, of at least one vegetable oil. Processes for preparing the fat base compositions and blend are also disclosed.Type: GrantFiled: April 27, 2006Date of Patent: May 10, 2016Assignee: ENZYMOTEC LTD.Inventors: Avidor Shulman, Gai Ben Dror, Hala Laouz, Dov Yaakobi, Zohar Bar-On, Gregory Blinder, Iris Meiri-Bendek, Yael Herzog
-
Patent number: 9282748Abstract: The invention provides an enzymatically-prepared fat base composition which comprises a mixture of vegetable-derived triglycerides. The fat base composition has a total palmitic acid residues content of at most 38% of the total fatty acid residues, and at least 60%, preferably 62% of the fatty acid moieties at the sn-2 position of the glycerol backbone are palmitic acid residues, at least 70% of the fatty acid moieties at the sn-1 and sn-3 positions of the glycerol backbone are unsaturated, at least 40%, preferably 40-60%, of the unsaturated fatty acid moieties at the sn-1 and sn-3 positions are oleic acid moieties, and at least 6%, preferably 6-17%, of the unsaturated fatty acid moieties at the sn-1 and sn-3 positions are linoleic acid moieties. The invention also provides preparation and various uses of the fat base composition in the field of infant nutrition.Type: GrantFiled: October 21, 2004Date of Patent: March 15, 2016Assignee: ENZYMOTEC LTD.Inventors: Iris Meiri-Bendek, Gai Ben Dror, Hala Laouz, Dov Yaakobi, Zohar Bar-On, Avidor Shulman
-
Publication number: 20150148554Abstract: The invention discloses an improved process for preparing fatty acid esters with 100 mol % selectivity suitable as biodegradable lubricant base oils, comprising contacting a fatty compound with an alcohol in presence of a solid, phosphonate catalyst having molecular formula: M(X)2-nYn.mH2O where X refers to phenyl phosphonate, Y refers to HPO42? or HPO32?, M refers to a metal or metalloid ion preferably taken from the group consisting of Zr, Zn, Cd, Al, Sn, La and Ce, the value of n varies from 0.2 to 1.8 and the value of m varies from 0 to 5, wherein the fatty compound is a fatty acid or fatty acid methyl or ethyl ester or vegetable oil or animal fat or their mixture thereof and alcohol is a monohydric alcohol with 6 to 22 carbon atoms or a polyol with at least two hydroxyl groups.Type: ApplicationFiled: May 22, 2013Publication date: May 28, 2015Inventors: Darbha Srinivas, Mehejabeen Kotwal
-
Publication number: 20140303388Abstract: The present invention relates to a method for producing a mixture containing fatty acid monoglyceride from glycerin and a compound having at least one acyl group, selected from fatty acids and fatty acid glycerides, including: (i) a step of obtaining a mixture containing fatty acid monoglyceride by heating and reacting glycerin and a compound having at least one acyl group, selected from fatty acids and fatty acid glycerides in the presence of a catalyst; (ii) a step including adding glycerin, which is liquid and has a lower temperature than the temperature of the mixture, to the mixture to cool the mixture; and (iii) a step of separating the mixture containing fatty acid monoglyceride from glycerin, obtained in the step (ii), by separating layers.Type: ApplicationFiled: December 7, 2012Publication date: October 9, 2014Inventors: Yasukazu Kumita, Takeshi Shirasawa
-
Publication number: 20140221675Abstract: A system and method for the conversion of high free fatty acid (HFFA) containing oils defined as oils containing 20-100% free fatty acids (FFA) and low free fatty acid (LFFA) containing oils defined as oils containing 1-20% free fatty acids (FFA) into oil with less than 0.5% FFA (defined as NFFA oil) includes a combination of partial glycerolysis of HFFA oils to produce LFFA oils and subsequent stripping of LFFA oils to produce NFFA oils via steam distillation.Type: ApplicationFiled: February 4, 2013Publication date: August 7, 2014Applicant: Technochem International, Inc.Inventor: Sanjeev Agarwal
-
Patent number: 8722814Abstract: Polyglycerol carboxylic acid esters are made by reaction of a, typically C2 to C30, particularly C6 to C22, carboxylic acid with glycerol carbonate, particularly with base catalyst, and desirably at temperatures from 170° C. to 250° C. Other carbonates e.g. cyclic diol carbonates such as ethylene or propylene carbonates, may be used in combination with the glycerol carbonate to make novel mixed polymeric esters. The molar ratio of carboxylic acid group to glycerol carbonate is typically from 2 to 30, but can be up to 100. The base catalyst is desirably alkali metal hydroxide, carbonate or alkoxide. The reaction is desirably carried out in an inert atmosphere, and reducing agent such as phosphorous acid, hypophosphorous acid or borohydride and/or activated carbon, may be included to improve product color.Type: GrantFiled: May 15, 2008Date of Patent: May 13, 2014Assignee: Croda International PLCInventors: Hanamanthsa Shankarsa Bevinakatti, Alan Geoffrey Waite, Jackie Frank
-
Publication number: 20140038249Abstract: The present invention provides a simpler and more energy efficient process for the preparation of fatty acid methyl ester (biodiesel) from sun dried whole seed capsules of Jatropha curcas integrated with value addition of seed shells, deoiled cake and crude glycerol co-product stream. More specifically, the invention relates to a method of dispensing with the need for excess methanol recovery through distillation, cost-effective resin treatment for the refining of methyl ester and utilization of co-streams for preparation of high density energy briquettes and Polyhydroxyalkanoate biodegradable polymer in efficient and cost-effective manner.Type: ApplicationFiled: March 29, 2010Publication date: February 6, 2014Applicant: COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCHInventors: Pushpito Kumar Ghosh, Sandhya Chandrika Prasad Mishra, Mahesh Ramniklal Gandhi, Sumesh Chandra Upadhyay, Parimal Paul, Pritpal Singh Anand, Kiritkumar Mangaldas Popat, Anupama Vijaykumar Shrivastav, Sanjiv Kumar Mishra, Neelam Ondhiya, Ramesh Dudabhai Maru, Gangadharan Dyal, Harshad Brahmbhatt, Vinod Boricha, Doongar Ram Chaudhary, Babulal Rebary, Krushnadevsingh Sukhdevsinh Zala
-
Publication number: 20140024847Abstract: Separate collection and conversion method and plant for the reuse of used oils and greases for energy purposes, which method provides one or more of the following steps: producing and separating the waste from other substances or compounds, collecting the waste gathering/storing the waste in at least a collection and/or regeneration facility, regenerating or treating the waste, reusing the collected or regenerated or treated waste, an oil or a grease or a mixture containing at least a natural and/or synthetic ester-based oil and/or grease being considered as waste, which oil or grease or which mixture is the by-product or waste of industrial processes.Type: ApplicationFiled: March 30, 2012Publication date: January 23, 2014Applicant: A. & A. Fratelli Parodi S.p.A.Inventors: Augusto Parodi, Leandro Marini
-
Publication number: 20130245300Abstract: A process for producing fatty acid methyl esters includes mixing an alcohol with a feedstock oil to prepare an alcohol/oil mixture, then reacting the alcohol/oil mixture using a first heterogeneous catalyst in an acid esterification process to produce a glycerin-containing product. The glycerin is separated from the glycerin-containing product using a coalescer to produce a biodiesel-containing feedstock and glycerin. Biodiesel is separated from the biodiesel-containing feedstock using a coalescer to produce unreacted feedstock and biodiesel. The unreacted feedstock is reacted using a second heterogeneous catalyst in a trans-esterification process to produce a glycerin-biodiesel-methanol mixture. Biodiesel and glycerin are separated in separate streams from the glycerin-biodiesel-methanol mixture, using a coalescer, to produce additional glycerin and additional biodiesel.Type: ApplicationFiled: September 14, 2011Publication date: September 19, 2013Inventor: Kyent Chin
-
Patent number: 8420842Abstract: This invention proposes a lanolin substitute, capable of absorbing up to at least twice its weight of water or aqueous solution or aqueous suspension. It forms true emulsions, stable over time with a capacity for water absorption superior to that of lanolin. It also possesses the known emollient, moisturizing and occlusive properties of lanolin. This substitute is usable in all the present and future areas of application of lanolin: in the cosmetics industry, dermatology, and in industrial applications (polishes, lubricants . . . ). It is obtained by hemi-synthesis from a mixture of unsaturated fatty acids, esters of unsaturated fatty acids, unsaturated hydrocarbons or unsaturated derivatives of the latter and compounds comprising or generating hydroxyl functions, such as glycerol, preferably without a catalyst and in an atmosphere devoid of oxygen. Classical thermal treatment or preferably treatment by dielectric heating.Type: GrantFiled: June 28, 2002Date of Patent: April 16, 2013Assignee: Aldivia SAInventors: Pierre Charlier De Chily, Mikaele Raynard
-
Patent number: 8361172Abstract: In the present invention, a fuel composition and a process for making the same are disclosed. Specifically, in the present invention, triglycerides useful for distillate fuels are described along with their method for preparation from Fischer-Tropsch acid by-products and the glycerol by-product from biodiesel generation. By using these two by-product streams, the overall efficiency of both processes is improved and a new source of distillate fuels is created. These triglycerides can be used to improve the lubricity of Fischer-Tropsch derived distillate fuels. In addition, these triglycerides also have low melting points and have viscosities compatible with distillate fuels.Type: GrantFiled: December 16, 2009Date of Patent: January 29, 2013Assignee: Chevron U.S.A. Inc.Inventor: Dennis J. O'Rear
-
Patent number: 8354551Abstract: Highly pure esterified propoxylated glycerin suitable for use as a fat substitute in various foodstuffs may be efficiently manufactured using a process involving direct esterification of propoxylated glycerin with excess fatty acid, bleaching, deacidification/deodorization, and treatment with activated carbon.Type: GrantFiled: February 28, 2012Date of Patent: January 15, 2013Assignee: Choco Finesse LLCInventors: Leopold Strecker, Louie Flowers, Dana Overman, David Rowe
-
Patent number: 8288574Abstract: Method for producing C3H5(OH)3 and at least one of fatty acid methyl ester (FAME) and fatty acid ethyl ester (FAEE) includes mixing vegetable oils and animal fats, at least one of CH3OH and C2H5OH and at least one first catalyst to transesterify a portion of triglycerides and provide a first mixture. The first mixture is separated, with a first light phase being withdrawn and fed into a second mixer where it is mixed with at least one second catalyst to transesterify a further portion of the triglycerides to provide a second mixture. The second mixture is separated, with a second light phase being withdrawn and mixed with soapless C3H5(OH)3 to provide a dispersion which is separated by density difference. A phase containing at least one of raw FAME and raw FAEE is mixed with an aqueous acid, washed with water, with the water being expelled to provide FAME and FAEE product.Type: GrantFiled: September 5, 2008Date of Patent: October 16, 2012Assignee: Lurgi GmbHInventors: Rudolf Boensch, Helmut Saft, Peter Mitschke, Henning Buchold
-
Patent number: 8283483Abstract: A polymerisable ethylenically unsaturated macromonomer being the reaction product of: i) an adduct formed from the reaction of an unsaturated non-mineral oil reacted with an enophile having an acid, ester or anhydride moiety and ii) an ethylenically unsaturated monomer having a moiety reactive with the acid, ester or anhydride moiety of the enophile and iii) a chain extender material having at least two moieties reactive with the acid, ester or anhydride moiety of the enophile.Type: GrantFiled: December 16, 2008Date of Patent: October 9, 2012Assignee: Akzo Nobel Coatings International B.V.Inventors: Neal St. John Williams, Chris Lampard
-
Publication number: 20120096763Abstract: A method of formulating a fuel composition for use in internal-combustion engines includes the step of providing a fuel. In addition, there is the step of forming the fuel composition by adding to the fuel a polar fluid and an emulsifier. The emulsifier is present in an amount effective for the biodiesel fuel, alcohol, water, and emulsifier to form an emulsion. The emulsifier includes an active surfactant mixture of oleic acid and ammonium oleate, wherein the ratio of oleic acid to ammonium oleate is no more than 60:40.Type: ApplicationFiled: August 24, 2011Publication date: April 26, 2012Applicant: WILLIAM H. KLAUSMEIER FAMILY TRUSTInventor: William H. Klausmeier
-
Patent number: 8124801Abstract: Processes for preparation of fatty acid alkyl esters are described herein. The processes include contacting fatty acid glycerides with alcohols in the presence of a catalyst separating the reaction products from the catalyst, and separating the fatty acid alkyl esters from the reaction products. The catalyst includes a metal from Group VIB of the Periodic Table and an element from Group VA of the Periodic Table.Type: GrantFiled: June 24, 2009Date of Patent: February 28, 2012Assignee: Benefuel Inc.Inventors: Darbha Srinivas, Paul Ratnassamy, Sanjeevani Amrit Pardhy, Thirumalaiswamy Raja, Shilpa Shirish Deshpande, Vijay Vasant Bokade, Kashinath Joti Wagmare, Arshia Altaf Lalljee, Surya Prakash Babu, Karukappadath Kunjimoideen Abdul Rashid, Khaliji Anas, Chennampilly Ummer Aniz
-
Publication number: 20110275750Abstract: Solvents for offset printing inks comprising at least one fatty acid ester that is the reaction product of at least one of C6-26 fatty acid and at least one polyhydroxy compound selected from the group consisting of polyglycerols, and adducts of 1 to 20 mol of ethylene oxide and/or propylene oxide with polyglycerols.Type: ApplicationFiled: December 21, 2009Publication date: November 10, 2011Inventors: Peter Bene, Juergen Baro, Jürgen Röder, Stefan Busch
-
Publication number: 20100256403Abstract: The present invention relates to the production of oil and fat containing acylglycerol esters including diacylglycerols, medium-chain and long-chain fatty acid triacyglycerols comprising esterification reaction between an acyl group donor and an acyl group acceptor in the presence of a heterogeneous chemical catalyst consisting of an ion-exchange resin preparation to obtain a reaction fluid that is further subjected to dehydration and at least one separation method, thus producing diacylglycerols and/or medium-chain and long-chain fatty acid triacyglycerols at a high yield in a short period of time.Type: ApplicationFiled: April 23, 2007Publication date: October 7, 2010Applicants: UNIVERSITI PUTRA MALAYSIA, GOLDEN HOPE RESEARCH SENDIRIAN BERHADInventors: Oi Ming Lai, Mohd Suria Affandi Yusoff, Seong Koon Lo, Kamariah Long, Chin Ping Tan, Shawaluddin Tahiruddin, Khairudin Hashim
-
Patent number: 7767838Abstract: The invention provides a process for producing a monoglyceride-containing composition by reacting glycerin with at least one kind of acyl-containing compound selected from fatty acid and glycerin ester, the reaction being conducted with a catalyst containing at least one metal selected from iron, cobalt and manganese in an amount of 0.1 to 60 ppm in terms of metal (weight ratio to the total weight of glycerin and the acyl-containing compound), as well as a process for producing a monoglyceride-containing composition by reacting glycerin with at least one kind of acyl-containing compound selected from fatty acid and glycerin ester, including a step of maintaining the amount of water at 500 to 5000 ppm in the reaction system after the degree of conversion in the reaction of glycerin with fatty acid reaches 90% or more based on the fatty acid, or during the ester exchange reaction of glycerin with glycerin ester.Type: GrantFiled: June 3, 2004Date of Patent: August 3, 2010Assignee: Kao CorporationInventors: Hiroki Sawada, Jiro Hashimoto, Haruya Mino, Toshitsugu Maeda
-
Publication number: 20100144978Abstract: Polyglycerol carboxylic acid esters are made by reaction of a, typically C2 to C30, particularly C6 to C22. carboxylic acid with glycerol carbonate, particularly with base catalyst, and desirably at temperatures from 170° C. to 250° C. Other carbonates e.g. cyclic diol carbonates such as ethylene or propylene carbonates, may be used in combination with the glycerol carbonate to make novel mixed polymeric esters. The molar ratio of carboxylic acid group to glycerol carbonate is typically from 2 to 30, but can be up to 100. The base catalyst is desirably alkali metal hydroxide, carbonate or alkoxide. The reaction is desirably carried out in an inert atmosphere, and reducing agent such as phosphorous acid, hypophosphorous acid or borohydride and/or activated carbon, may be included to improve product colour.Type: ApplicationFiled: May 18, 2008Publication date: June 10, 2010Inventors: Hanamanthsa Shankarsa Bevinakatti, Alan Geoffrey Waite, Jackie Frank
-
Publication number: 20090326252Abstract: Processes for preparation of fatty acid alkyl esters are described herein. The processes include contacting fatty acid glycerides with alcohols in the presence of a catalyst separating the reaction products from the catalyst, and separating the fatty acid alkyl esters from the reaction products. The catalyst includes a metal from Group VIB of the Periodic Table, a metal from Group IIIA of the Periodic Table, and an element from Group VA of the Periodic Table.Type: ApplicationFiled: June 24, 2009Publication date: December 31, 2009Inventors: Darbha Srinivas, Paul Ratnasamy, Sanjeevani Amrit Pardhy, Thirumalaiswamy Raja, Shilpa Shirish Deshpande, Vijay Vasant Bokade, Kashinath Joti Wagmare, Arshia Altaf Lalljee, Surya Prakash Babu, Karukappadath Kunjimoideen Abdul Rashid, Khaliji Anas, Chennampilly Ummer Aniz
-
Patent number: 7629478Abstract: A process for preparing palm-based polyol monomer includes reacting unsaturated fatty acids or its corresponding triglycerides with polyhydric alcohol. In particular, one example uses oleic acid with about 70% purity as the starting material for preparing the polyol monomer. Moreover, another example uses refined, bleached, and deodorized (RBD) palm olein as an alternative to oleic acid as the starting material. The preparation of the polyol monomer involves the production of monoglyceride of unsaturated fatty acids, which was further epoxidized with peracid and finally ring opened with polyhydric alcohols. Such polyol monomer is used as a raw material for the production of various types of polyurethane products.Type: GrantFiled: November 6, 2006Date of Patent: December 8, 2009Assignee: Malaysian Palm Oil Board (MPOB)Inventors: Hoong Seng Soi, Nur Musyahadah Mazalan, Mohd Nurhisham Sattar, Tuan Noor Mazne Tuan Ismail, Hazimah Abu Hassan, Ooi Tian Lye, Salmiah Ahmad, Mohd Basri Wahid, Tan Sri Datuk Yusof Basiron
-
Publication number: 20090260280Abstract: A method of formulating a fuel composition for use in internal-combustion engines includes the step of providing a fuel. In addition, there is the step of forming the fuel composition by adding to the fuel a polar fluid and an emulsifier. The emulsifier is present in an amount effective for the biodiesel fuel, alcohol, water, and emulsifier to form an emulsion. The emulsifier includes an active surfactant mixture of oleic acid and ammonium oleate, wherein the ratio of oleic acid to ammonium oleate is no more than 60:40.Type: ApplicationFiled: April 17, 2008Publication date: October 22, 2009Inventor: William H. Klausmeier
-
Publication number: 20040075079Abstract: The invention relates to compositions comprising an ester of a polyol and a mixture of fatty acids, wherein at least a part (I) of the esterified fatty acids has a chain length of 5-12 carbon atoms and another part (II) of the esterified fatty acids has a chain length of 16-22 carbon atoms, and wherein the composition has a viscosity of 7000 mm 2 /s or less, when tested according to ASTM (D2531). Such compositions have unexpected good low temperature properties, in particular a good rheology after having been kept for a prolonged time at a low temperature (e.g. at −30° C.). These compositions are suitable for use as (part of) hydraulic fluid in applications at low temperatures.Type: ApplicationFiled: September 26, 2003Publication date: April 22, 2004Applicant: UNICHEMA CHEMIE BVInventors: Thomas Friedrich Bunemann, Arie Dick Kardol, Abraham Comelis de Mooij
-
Patent number: 6610868Abstract: Novel compositions containing conjugated linoleic acids are efficacious as animal feed additives and human dietary supplements. Linoleic acid is converted to its conjugated forms in which the resulting composition is low in certain unusual isomers compared to conventional conjugated linoleic products.Type: GrantFiled: April 18, 2002Date of Patent: August 26, 2003Assignee: Natural CorporationInventors: Asgeir Saebo, Carl Skarie, Daria Jerome, Gudmunder Haroldsson
-
Patent number: 6423856Abstract: The present invention relates to a process for preparing ester plasticizers from ethylene glycol or the dimers, trimers or tetramers of this compound and linear or branched aliphatic monocarboxylic acids having from 3 to 20 carbon atoms. The reaction is carried out in the presence of organic substances having a boiling point of <112° C., in particular cyclohexane, as azeotrope formers (entrainers) for removing the water of reaction.Type: GrantFiled: August 24, 2000Date of Patent: July 23, 2002Assignee: Celanese Chemicals Europe GmbHInventors: Helmut Springer, Klaus-Dieter Merscher, Rudolf Heumuller, Klaus Schimmer, Heinz Strutz
-
Patent number: 6410761Abstract: Novel compositions containing conjugated linoleic acids are efficacious as animal feed additives and human dietary supplements. Linoleic acid is converted to its conjugated forms in which the resulting composition is low in certain unusual isomers compared to conventional conjugated linoleic products.Type: GrantFiled: March 17, 1999Date of Patent: June 25, 2002Assignee: Conlinco, Inc.Inventors: Asgeir Saebo, Carl Skarie, Daria Jerome, Gudmunder Haroldsson
-
Patent number: 6361980Abstract: The present invention provides a process for preparing a diglyceride, which includes: in an enzyme-packed tower which includes an immobilized lipase preparation, carrying out an esterification reaction between: (1) an acyl group donor selected from the group including a fatty acid, a lower alcohol ester thereof, and a mixture thereof; and (2) an acyl group acceptor selected from the group including glycerol, a monoglyceride, and a mixture thereof; to obtain a reaction fluid from the enzyme-packed tower; reducing a water content or a lower alcohol content in the reaction fluid; and subsequent to the reducing, recirculating the reaction fluid to the enzyme-packed tower, wherein a residence time of the reaction fluid in the enzyme-packed tower is 120 seconds or less; to obtain a diglyceride. According to the present invention, a high-purity glyceride can be provided at a high yield in a short period of time.Type: GrantFiled: November 30, 2000Date of Patent: March 26, 2002Assignee: Kao CorporationInventors: Masakatsu Sugiura, Hiroaki Yamaguchi, Naoto Yamada
-
Patent number: 6342199Abstract: The invention relates to a process for conducting a chemical reaction characterized by an equilibrium in a reaction system designed as a loop reactor, said loop reactor comprising a reactor vessel (1), at least one loop connected to said reactor vessel (1) each by means of an outlet and an inlet, said loop comprising means (3) for pumping over a fluid reaction material, at least one he exchanger (4), optionally means (5) for feeding said reaction material into Me reactor vessel (1) and a separate gas loop (8) which is connected to the gas space of the reactor vessel (1) above the reaction mixture and has separate means for feeding a gas into the gas loop (8), for withdrawing gas from the gas loop (8) and/or for treating said gas circulating in the gas loop (8), said process comprising the steps of circulating and/or treating said gas in said gas loop (8), feeding said gas into the reactor vessel (1) for influencing the equilibrium of a reaction conducted in said reactor vessel (1) and being characterized by tType: GrantFiled: June 18, 1999Date of Patent: January 29, 2002Inventor: Vincent Simon Ellis
-
Patent number: 6320065Abstract: The invention relates to a process for the preparation of fatty acid partial esters of polyols, the fatty acid partial esters thus obtainable, and their use. The fatty acid partial esters (I) of polyols having at least 4 C atoms, at least one primary and at least one secondary alcohol group of the starting polyols are obtained in a process, where in a first process step the polyols are reacted with a fatty acid or a fatty acid derivative to give a fatty acid partial ester (II) and in a second process step the fatty acid partial esters (II) obtained are subjected to a selective enzymatic cleavage of primary ester groups.Type: GrantFiled: May 7, 1999Date of Patent: November 20, 2001Assignee: Goldschmidt AGInventors: Burghard Gruning, Geoffrey Hills
-
Patent number: 6177580Abstract: A process for making synthetic triglycerides involving: (a) providing a reaction component selected from the group consisting of glycerol, a triglyceride, and mixtures thereof; (b) providing a fatty acid mixture containing at least 50% by weight, based on the weight of the fatty acid mixture, of conjugated linoleic acid; (c) providing an inert gas atmosphere; (d) combining the reaction component with the fatty acid mixture, in the inert atmosphere, to form a reaction mixture; and (e) heating the reaction mixture to a temperature of from 180 to 240° C., at a heating rate of from 0.5 to 3 K per minute, thus forming the synthetic triglyceride.Type: GrantFiled: October 29, 1999Date of Patent: January 23, 2001Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Franz Timmermann, Rolf Gaupp, Juergen Gierke, Rainer Von Kries, Wolfgang Adams, Andreas Sander
-
Patent number: 5597934Abstract: The preparation of polyol compounds by (a) condensing glycerine in the presence of lithium compounds; (b) continuously distilling off the water produced by the reaction; (c) optionally subjecting the oligoglycerine mixture obtained to a transesterification reaction with fatty-acid glyceride esters. Such polyol compounds are suitable for use as starting materials in the production of polymers.Type: GrantFiled: June 7, 1995Date of Patent: January 28, 1997Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Johann Klein, Peter Daute, Udo Hees, Bernd Beuer
-
Patent number: 5585506Abstract: A semi-batch process for the manufacture of polyglycerol esters by direct fatty acid esterification of a polyglycerol. Molten fatty acid is fed slowly into polyglycerol at a rate which maintains the reaction mixture substantially homogeneous. Improved quality of the resultant polyglycerol esters and shorter reaction cycles are thereby realized.Type: GrantFiled: July 22, 1994Date of Patent: December 17, 1996Assignee: Lonza Inc.Inventors: Scott B. Harvey, Shilan Shen
-
Patent number: 5466843Abstract: Esterified alkoxylated polyols containing long chain saturated linear acyl groups are obtained by esterification of an alkoxylated polyol such as propoxylated glycerin with a C.sub.12 -C.sub.24 fatty acid such as behenic acid and recovery of excess fatty acid by treatment with an aliphatic hydrocarbon. Esterified alkoxylated polyols prepared in this manner are useful fat substitutes for the formulation of reduced calorie food products.Type: GrantFiled: April 29, 1994Date of Patent: November 14, 1995Assignee: ARCO Chemical Technology, L.P.Inventor: Charles F. Cooper
-
Patent number: 5466719Abstract: Polyglycerol fatty acid ester mixtures of mono- di- and polyesters of polyglycerols having a degree of polymerization of 2 to 8 and at least one saturated and/or unsaturated fatty acid, the mixtures having an HLB of greater than 8 and containing 0 to less than 5 wt-% diglycerol fatty acid esters, 20 to 65 wt-% triglycerol fatty acid esters, 20 to 50 wt-% tetraglycerol fatty acid esters and 5 to 40 wt-% higher polyglycerol fatty acid esters, in which the fatty acid component consists of one or more fatty acids selected from the saturated and/or unsaturated, branched and/or unbranched C.sub.6 - to C.sub.14 -fatty acids containing less than 10 wt-% fatty acids having more than 14 carbon atoms; bath additive preparations containing such polyglycerol fatty acid ester mixtures; methods of using such polyglycerol fatty acid ester mixtures, and a process for preparing such mixtures.Type: GrantFiled: August 4, 1993Date of Patent: November 14, 1995Assignee: Solvay Fluor und Derivate GmbHInventors: Gerald Jakobson, Werner Siemanowski, Karl-Heinz Uhlig
-
Patent number: 5436006Abstract: Diclosed is a lanolin-like synthetic oil produced by esterification of glycerol with a branched fatty acid having 6 to 14 carbon atoms, a linear fatty acid having 15 to 28 carbon atoms and a dibasic acid having 4 to 10 carbon atoms while all the following conditions (a) to (c) are satisfied:(a) molar ratio of the branched fatty acid to the linear fatty acid ranges from 1.7 to 2.3,(b) 0.7 to 0.8 mol of the dibasic acid is used per mol of glycerol, and(c) the number of remaining hydroxyl group ranges from 0.4 to 0.6 for three hydroxyl groups of glycerol.The synthetic ester oil has a color, smell and stability superior to those of lanolin and an adherability, spreadability, gloss and touch very similar to those of lanolin. Such an oil can be suitably incorporated into cosmetics, toiletries and external preparations to overcome the defects of lanolin and also to exhibit the characteristic features of the oil.Type: GrantFiled: July 23, 1993Date of Patent: July 25, 1995Assignee: The Nisshin Oil Mills, Ltd.Inventors: Tadashiro Hirose, Yoshihiro Ueda, Takashi Murata
-
Patent number: 5405980Abstract: Condensates (K) of(A) oligohydroxy-C.sub.3-8 -alkanes containing at least 3 hydroxy groups and (B) KOH,that contain at least 5% by weight of K.sup.+ and at least one alcoholic hydroxy groupare eminently suitable as oxyalkylation catalysts, in particular for the oxyalkylation of ester group-containing substrates, before all of natural, vegetable or animal fats or oils or their modification products.Type: GrantFiled: February 24, 1993Date of Patent: April 11, 1995Assignee: Sandoz Ltd.Inventor: Hans-Peter Baumann
-
Patent number: 5399729Abstract: Reduced calorie food compositions are prepared using fatty acid esterified alkoxylated polyol fat substitutes derived from C.sub.3 and higher epoxides and having a high proportion of primary ester linkages. The fat substitutes may be obtained by alkoxylation of a polyol such as glycerin with the epoxide in the presence of a cationic/ring-opening polymerization catalyst, followed by esterification with a fatty acid or a fatty acid equivalent.Type: GrantFiled: August 31, 1993Date of Patent: March 21, 1995Assignees: Arco Chemical Technology, L.P., CPC International Inc.Inventors: Charles F. Cooper, Stephen H. Harris
-
Patent number: 5371253Abstract: Esterified alkoxylated mono- and diglycerides suitable for use as reduced calorie fat substitutes in food products may be produced by alkoxylating a tertiary alkyl partial ether of glycerin with an epoxide and then reacting the alkoxylated glycerin tertiary alkyl partial ether thereby obtained with a fatty acid under acid-catalyzed conditions. Separate deprotection and esterification steps are not required, resulting in a considerably streamlined process as compared to alternative methods of synthesizing alkoxylated fat substitutes having one or two fatty acid acyl groups attached directly to glycerin.Type: GrantFiled: December 14, 1993Date of Patent: December 6, 1994Assignee: Arco Chemical Technology, L.P.Inventor: Charles F. Cooper
-
Patent number: 5164191Abstract: The present invention features a method of making lipid vesicles and the lipid vesicles themselves made from monomeric and dimeric alkyds. These alkyds are esters made as a condensation product of a first reactant having at least one free hydroxyl group and a C.sub.12 -C.sub.20 fatty acids chain and a second reactant which is an aromatic acid chloride or anhydride. Preferred first reactants are esters of polyols and C.sub.12 -C.sub.20 fatty acids, ethers of polyols and C.sub.12 -C.sub.20 fatty acids, and C.sub.12 -C.sub.20 fatty alcohols.Type: GrantFiled: February 12, 1991Date of Patent: November 17, 1992Assignee: Micro Vesicular Systems, Inc.Inventors: S. Esmail Tabibi, An-Cheng Chang, Rajiv Mathur, Donald F. H. Wallach
-
Patent number: 5149852Abstract: This invention provides a process for concentration and separation of an eicosapentaenoic acid ester comprising:(1) a step in which a solution, in a nonpolar solvent, of a mixture of fatty acid esters containing an eicosapentaenoic acid ester is allowed to contact with a zeolite, so as to allow said eicosapentaenoic ester to be adsorbed on said zeolite;(2) a step in which said zeolite is allowed to contact with a nonpolar solvent, so as to desorb impurities; and(3) a step in which said zeolite is allowed to contact with a polar solvent, so as to allow said eicosapentaenoic acid ester to be desorbed.This process makes it possible to obtain a highly pure eicosapentaenoic acid ester on a commercial scale.Type: GrantFiled: March 27, 1991Date of Patent: September 22, 1992Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Makoto Arai, Hideki Fukuda
-
Patent number: 5137660Abstract: A process for the selective esterification of glycerol and 1-glyceryl derivatives to 1,3-disubstituted glycerides is disclosed. This process uses a water immiscible solvent, either a hydrocarbon or halogenated hydrocarbon, a 1,3-lipase and fatty acid anhydrides. This reaction mixture selectively esterifies the primary alcohol groups of glycerol or glycerol derivatives. The preferred derivatives of glycerol are alkyl ethers, alkyl phosphates, phospholipids, alkyl and diaklyl phosphates, and sugar glycosides.Type: GrantFiled: March 15, 1991Date of Patent: August 11, 1992Assignee: The Procter & Gamble CompanyInventors: Adam W. Mazur, George D. Hiler, II
-
Patent number: 5135683Abstract: An improved process for the hydrolysis and purification of an alkoxylated polyol containing a ketal protective functionality is described. The process may be employed to prepare reduced calorie esterified alkoxylated polyol fat mimetics useful in cooking and in food compositions.Type: GrantFiled: March 28, 1991Date of Patent: August 4, 1992Assignees: Arco Chemical Technology, L.P., CPC International Inc.Inventor: Charles F. Cooper
-
Patent number: 5118448Abstract: Esterified alkoxylated polyols useful as fat mimetics may be prepared by alkoxylating a benzylated polyol with an epoxide under basic conditions, reacting the benzyl ether group with hydrogen to convert it to a hydroxy group, and then esterifying with a fatty acid compound. The resulting product has at least one fatty acid ester group attached directly to the polyol residue.Type: GrantFiled: October 19, 1990Date of Patent: June 2, 1992Assignee: Arco Chemical Technology, L.P.Inventor: Charles F. Cooper
-
Patent number: 5110508Abstract: The invention relates to a process, more especially a discontinuous process, for conducting a reaction taking place at elevated temperature in which heat-sensitive products are formed. To increase the volume-time yield, a heat transfer unit independent of the reactor is used for heating. The invention also relates to an apparatus for the production of heat-sensitive products at elevated temperatures. This apparatus comprises a reactor and a heating system. To increase the volume-time yield, the heating system comprises at least one heat transfer unit arranged outside and connected to the reactor.Type: GrantFiled: April 20, 1989Date of Patent: May 5, 1992Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Karl-Heinz Buettgen, Bernhard Gutsche, Friedrich Hommers, Wilhelm Johannisbauer, Eberhard Peukert, Reinhold Sedelies