Abstract: The invention relates to a substance which lowers LDL cholesterol levels in serum and which is fat soluble &bgr;-sitostanol fatty acid ester, and to a method for preparing and using the same. The substance can be taken orally as a food additive, food substitute or supplement. A daily consumption of the &bgr;-sitostanol ester in an amount between about 0.2 and about 20 g/day has been shown to reduce the absorption of biliary and endogenic cholesterol.
Abstract: Processes for preparing linoleic acid raw materials are described wherein the processes comprise: (a) transesterifying a triglyceride component with an alcohol having from 1 to 4 carbon atoms, at a temperature of from 80 to 120° C., to form a transesterification mixture comprising linoleic acid esters and one or more by-products selected from the group consisting of glycerides, free glycerol, and soaps, wherein the triglyceride component is comprised of at least 60% by weight linoleic acid; and (b) removing the one or more by-products from the transesterification mixture.
Type:
Grant
Filed:
March 13, 2003
Date of Patent:
July 13, 2004
Assignee:
Cognis Deutschland GmbH & Co. KG
Inventors:
Albert Strube, Uwe Hoemmerich, Bernhard Gutsche
Abstract: A process of producing a light-colored, high-monoester mixture from a polyol and an oil is provided wherein the process eliminates the use of organic solvents, multiple water washings and/or molecular distillation. The reactants, a polyol and an oil, described herein, condense in the presence of a catalyst, described herein, at a temperature range from about 180° C. to about 280° C. under an inert atmosphere or the vapor pressure of the polyol with a pressure of about 0 to about 500 psig to yield a monoester mixture possessing a desirable monoester composition and color. The present process yields a final product similar to that of processes which require the use of solvents, multiple water washings and/or molecular distillation.
Abstract: The present invention relates to a liquid phase process for the direct hydrolysis of a fatty acid ester to the corresponding fatty acid and alcohol in the presence of a catalyst, wherein the fatty acid in the liquid phase is contacted with steam in the presence of a compound of a metal that is capable of forming a soap with a large hydration shell as a catalyst.
Type:
Grant
Filed:
April 8, 2002
Date of Patent:
November 11, 2003
Assignee:
HaltermannAscot GmbH
Inventors:
Jacobus Sinnema, Luc De Graef, Thomas Meisel, Inge Mussler
Abstract: Complexes of a selected class of chiral ligands with molybdenum, tungsten or chromium, preferably molybdenum, are effective as catalysts in highly enantioselective and regioselective alkylation of allylic substrates.
Type:
Grant
Filed:
September 7, 2001
Date of Patent:
April 1, 2003
Assignee:
The Board of Trustees of the Leland Stanford Junior
University
Abstract: The present invention relates to a method for producing fatty acid esters of monovalent alkyl alcohols by base-catalyzed transesterification of fatty acid esters of polyvalent alcohols. In said method, oils are used which contain free fatty acids and phosphatides, in addition to fatty acid esters of polyvalent alcohols. The method consists of several stages. The fatty acids contained in the starting material are treated with a base mixture of glycerine and a catalyst. This mixture is produced as a polar phase in the following transesterification stages and can be separated from the reaction mixture, using phase separation. Calculation procedures are provided for determining the minimum amount of catalyst necessary, depending on the acid number of the oil. The invention also relates to the use of esters produced by this method as diesel fuels.
Abstract: The present invention relates to acetoacetic acid derivatives of the formula Ia or Ib, to processes for their preparation and to their use for the preparation of 2,15-hexadecanedione. The invention further relates to the use of the compounds of the formula Ia or Ib
where R is an optionally substituted straight-chain or branched C1-C6-alkyl, C1-C6-alkoxyalkyl or phenyl radical, alkoxy groups are a combination of an alkyl group according to the above definition with an oxygen atom, e.g. methoxy, ethoxy, propoxy, butoxy or pentoxy groups, which comprises adding an acetoacetic ester of the formula II
to 1,9-decadiene by a free-radical means, as intermediate for the preparation of muscone (3-methylcyclopentadecanone).
Abstract: Secondary alcohol esters of hydroxyacids, e.g., ricinoleate esters of secondary alcohols, are prepared by reacting an ester of a hydroxyacid with a secondary alcohol, in the presence of an organometallic transesterification catalyst. Under these reaction conditions, a high proportion of the starting ester of a hydroxyacid is converted into a secondary alcohol ester of the hydroxyacid, while minimizing the formation of by-products including estolide. The product esters and composition containing same may be used as a lubricity agent or as a friction modifier in a lubricant composition.
Type:
Grant
Filed:
January 10, 2000
Date of Patent:
June 18, 2002
Assignee:
Arizona Chemical Company
Inventors:
Lloyd A. Nelson, Charley M. Pollock, Gregory J. Achatz
Abstract: The present invention provides a heterogeneous catalyst which is highly active, excellent in selectivity and free from elution of its catalyst-components during reaction and which has long lifetime. That is, a phosphate of a metal selected from the group consisting of aluminum, gallium and iron is used as the catalyst for transesterification of the present invention.
Type:
Grant
Filed:
June 22, 2001
Date of Patent:
June 18, 2002
Assignee:
Kao Corporation
Inventors:
Jun Kaita, Taku Mimura, Noriaki Fukuoka, Yasuyuki Hattori
Abstract: 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.
Abstract: The present invention relates to a method for solubilizing polystyrene in a fatty acid ester, whereby the resultant polystyrene fatty acid ester composition can be used in a variety of polymeric applications, including forming an improved polyester. The present invention also relates to the resultant polystyrene fatty acid ester composition.
Type:
Grant
Filed:
September 25, 2000
Date of Patent:
January 8, 2002
Inventors:
Shubhen Kapila, Virgil J. Flanigan, Michael F. Maples, Michael W. Mills
Abstract: A process for the preparation of mixtures which comprise mostly sorbitol monoesters, sorbitol diesters and partial glycerides, sorbitol being reacted with triglycerides in the presence of at least one alkaline catalyst, is described, wherein the cocatalyst used for the reaction is:a) a part amount of the product of the above reaction as a self-emulsifier and/orb) an amidoamine of the following formula (I) ##STR1## in which in which: R.sup.1 is an alkyl or alkenyl group having 6 to 13 carbon atoms, R.sup.2 is an alkyl group having 1 to 6 carbon atoms or an H atom, R.sup.3 is an alkyl group having 1 to 6 carbon atoms and n is a number from 1 to 6. The novel process gives purer products and leads to a considerably improved space/time yield.
Abstract: This invention relates to a process for removing sterols and phosphorous compounds from naturally occurring lipid mixtures. The process involves hydrolyzing a naturally occurring lipid mixture containing phospholipids, triglycerides, and sterols to form a two-phase product containing a fatty acid phase comprised of free fatty acids and sterols, and an aqueous phase comprised of water, glycerol, and glycerol phosphoric acid esters. The aqueous phase is separated from the fatty acid phase and the crude fatty acid phase is heated to convert the free sterols to fatty acid sterol esters. The free fatty acids are distilled from the fatty acid sterol esters to yield purified fatty acids which are free of cholesterol and other sterols, and phosphorous compounds.
Type:
Grant
Filed:
December 18, 1996
Date of Patent:
June 29, 1999
Assignee:
Eastman Chemical Company
Inventors:
Scott Donald Barnicki, Charles Edwan Sumner, Jr.
Abstract: Rhenium oxide catalysts carried on aluminium silicates, if required with added boric oxide, tungsten oxide, molybdenum oxide or vanadium oxide for the metathesis of olefins and functionalised olefins, in particular of carboxylic acid esters, are provided, whereby the carrier material was hydrothermally treated.
Type:
Grant
Filed:
June 20, 1997
Date of Patent:
March 16, 1999
Assignee:
RWE-DEA Aktiengesellschaft fur Mineraloel und Chemie
Abstract: A process for the preparation of a salt of fatty acid ester of hydroxycarboxylic acid, which comprises subjecting a fatty acid ester of lower alcohol and an alkaline metal salt or alkaline earth metal salt of hydroxycarboxylic acid to ester interchange in an organic solvent in the presence of a nonionic or anionic surface active agent and an alkali catalyst. The highly pure salt of fatty acid ester of hydroxycarboxylic acid obtained by the separation and purification of the reaction product exhibits a remarkably excellent surface activating ability as compared with the existing commercial products.
Abstract: A method for the preparation of fatty acid alkyl esters by transesterification, in particular catalytic transesterification, of triglycerides, wherein from a reaction mixture, in which the transesterification is carried out, an ester phase and a glycerol phase containing fatty acids, fatty acid salts and/or other fatty acid compounds are formed, which are separated from each other, characterized in that the fatty acids, the fatty acid salts and/or other fatty acid compounds are separated from the glycerol phase, esterified with an alcohol and recycled to a different reaction mixture, in which a further transesterification is carried out. The method according to the invention allows for a transesterification with a high yield of fatty acid esters.
Type:
Grant
Filed:
February 27, 1996
Date of Patent:
December 15, 1998
Assignees:
Martin Mittelbach, Michael Koncar, Vogel & Noot Industrieanlagenbau Gesellschaft m.b.H.
Abstract: A process for making a polyglycerol polyhydroxystearate comprising esterifying a polyhydroxystearic acid having a degree of self-condensation of from 2 to 20 with a polyglycerol component, the polyglycerol component consisting of: (a) from 5 to 30% by weight of a glycerol; (b) from 15 to 40% by weight of a diglycerol; (c) from 10 to 30% by weight of a triglycerol; (d) from 5 to 20% by weight of a tetraglycerol; (e) from 2 to 10% by weight of a pentaglycerol; and (f) remainder, up to 100%, of an oligoglycerol.
Type:
Grant
Filed:
December 13, 1996
Date of Patent:
November 24, 1998
Assignee:
Henkel Kommanditgesellschaft auf Aktien
Inventors:
Achim Ansmann, Rolf Kawa, Rainer Von Kries, Gabriele Strauss
Abstract: A novel method for preparing an aryl-substituted fatty acid or fatty ester is disclosed. According to the method, an olefinic composition selected from among mono-unsaturated fatty acids, mono-unsaturated fatty esters and mixtures thereof is introduced to a reaction zone comprising a liquid aromatic hydrocarbon and a catalytic amount of a clay catalyst to produce a reaction that is allowed to proceed for a time and at a temperature sufficient to produce a reaction product comprising a desired yield of aryl-substituted fatty acid or fatty ester. Preferably, the introduction of the olefinic composition is conducted slowly, such as over a period of one to four, more preferably, two to four, hours. Related methods and compositions, including xylylstearic acid, are also disclosed.
Abstract: A method of synthesizing 9-cis-retinoic acid, all-trans-retinoic acid or 9-nor-retinoic acid is disclosed. The method comprises the steps of adding a Grignard reagent of ##STR1## to 2,2,6 trimethyl cyclohexanone is disclosed. R is a methyl group or H and the CH.sub.2 --OH group is in either the cis or trans orientation relative to the HC.tbd.C- group. The resulting product is converted into retinoic acid. In the preferable form of the present invention, a tritium-labelled retinoic acid is synthesized, wherein the labelling is at the C.sub.20 position. A preparation of tritium-labelled 9-cis-retinoic acid with a specific activity of greater than 65 Ci/mmol is also enclosed. In a most preferred embodiment, the specific activity is greater than 75 Ci/mmol.
Abstract: Esterification of an ultra-low unsaturation polyoxy(higher)alkylene polyol with a dicarboxylic acid or reactive derivative thereof to form a poly(half ester) followed by capping the poly(half ester) with a capping agent capable of forming an amide linkage or ester linkage while retaining primary hydroxyl functionality, generates high primary hydroxyl content polyols with substantially retained hydrophile/lipophile balance and low polydispersity. Low color products having primary hydroxyl contents in excess of 80 equivalent percent may be routinely achieved.
Abstract: Chemical synthesis of N-acyl-N-alkylcarboxylates through oxidation of substituted amides formed from carboxylic acid esters and an N-alkyl-N-alkanolamine.
Type:
Grant
Filed:
June 23, 1995
Date of Patent:
July 8, 1997
Assignee:
The Procter & Gamble Company
Inventors:
James Carey Letton, Larry Eugene Miller
Abstract: Methods for the synthesis of 9-cis monotritium-labeled retinoids, and their use in the discovery of Retinoid X Receptor ligands are provided. In addition, 9-cis monotritium-labeled retinoids, as well as novel intermediates and tritium-labeled intermediates formed during the synthesis of 9-cis monotritium-labeled retinoids are also provided.
Abstract: There is disclosed an improved telomerized oil comprising no more than 4% polyunsaturated fatty acids and a plurality of aliphatic rings, wherein the improved telomerized oil is made from about 20% to about 70% of a conjugated triglyceride oil, wherein the conjugated triglyceride oil has at least 50% of fatty acids having at least two conjugated double bonds and from about 30% to about 80% of a vegetable triglyceride oil, wherein the vegetable triglyceride oil has from about 10% to about 75% of its fatty acids being polyunsaturated and having from about 16 to about 26 carbon atom chain length (unbranched).
Abstract: The present invention relates to an improved process for preparing fatty acids from alkyl, preferably methyl esters comprising mixing the fatty acid ester with water, acid catalyst, and DMSO in order to form a single phase reaction mixture. The single phase reaction mixture is then heated to a temperature of from about 70.degree. C. to about 130.degree. C. to hydrolyze the fatty acid ester into the corresponding acid and volatile alcohol and removing the volatile alcohol. The acid catalyst is heat and water stable and the reaction mixture is essentially free of C.sub.2 -C.sub.5 carboxylic acids. The initial stoichiometric ratio of the water to the ester is at least about 1:1.
Abstract: Olefinically unsaturated adducts of propylene on polyunsaturated fatty acids with 18 to 22 carbon atoms or on esters of these fatty acids with C.sub.1 -C.sub.36 alkanols in molar ratios of propylene to fatty acids or fatty acid esters in the range from 1:1 to 2:1, obtainable by reacting the fatty acids or fatty acid esters with propylene at elevated temperature and pressure in the presence of compounds of the transition metals Ru, Rh, Pd, Ir and Pt as catalysts to form an olefinically unsaturated adduct.
Abstract: 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.
Abstract: Process for the production of branched fatty acids and their esters comprising reacting unsaturated fatty acids or esters thereof with aliphatic nonactivated olefins in the presence of layer silicates and active carbon.
Abstract: The metathesis of functionalized and unfunctionalized acyclic olefins using catalyst compositions containing iridium and silver in a molar ration of 3 to 1.
Abstract: Olefinically unsaturated adducts of ethylene on polyunsaturated fatty acids with 18 to 22 carbon atoms or on esters of these fatty acids with C.sub.1 -C.sub.36 alkanols in molar ratios of ethylene to fatty acids or fatty acid esters in the range from 1:1 to 3:1 obtainable by reacting the fatty acids or fatty acid esters with ethylene at elevated temperature and pressure in the presence of compounds of the transition metals Ru, Rh, Pd, Ir and Pt as catalysts to form an olefinically unsaturated adduct.
Abstract: A process for the metathesis of olefins and functionalized olefins on Re.sub.2 O.sub.7 /Al.sub.2 O.sub.3 -containing catalysts, which comprises effecting metathesis reaction in the presence of one or more halogen-free organoaluminum compounds as activators.
Type:
Grant
Filed:
February 22, 1991
Date of Patent:
June 8, 1993
Assignee:
Huels Aktiengesellschaft
Inventors:
Siegfried Warwel, Hans-Gerd Jagers, Barbara Ercklentz
Abstract: Glycerides of eicosapentaenoic acid (EPA) and other higher fatty acids, which contain high levels of EPA and docosahexaenoic acid. These glycerides are incorporated in oils and fats products such as margarine, shortening, mayonnaise, butter, dressing or edible oil.
Abstract: A catalyst for the metathesis of olefins and functionalized olefins, which contains a compound having the formula B.sub.2 O.sub.3 --Re.sub.2 O.sub.7 /Al.sub.2 O.sub.3 --SiO.sub.2.
Type:
Grant
Filed:
February 22, 1991
Date of Patent:
September 1, 1992
Assignee:
Huls Aktiengesellschaft
Inventors:
Siegfried Warwel, Hans-Gerd Jagers, Andreas Deckers
Abstract: The present invention is directed to a novel internal mold release agent for use in a polyurethane(urea) RIM process. The release agent broadly consists of the transesterification product of a fatty acid and a lower alkyl acetoacetate.
Abstract: Process for the acid-catalyzed hydrolysis of fatty acid glycerides, wherein the process is carried out continuously with the glyceride and the water being moved countercurrent to each other, and apparatus therefor.
Type:
Grant
Filed:
August 1, 1989
Date of Patent:
July 7, 1992
Assignee:
Henkel Kommanditgesellschaft auf Aktien
Inventors:
Reinhold Sedelies, Wilhelm Johannisbauer, Guenter Wozny, Lutz Jeromin, Gerhard Dieckelm, Manfred Lindemann, Gerd Matrong