Molecular Rearrangement Of The Acid Moieties Of Glyceride Esters (e.g., Random Or Directed Low Temperature Intra- Or Inter-esterification Of Fats, Oils, Etc.) Patents (Class 554/169)
Abstract: Fatty acid glycerides can be transesterified with lower aliphatic alcohols if the reaction is carried out in the presence of fatty acids corresponding to formula (II):R.sup.2 --COOH (II),in which R.sup.2 is an aliphatic hydrocarbon moiety containing 11 to 17 carbon atoms and 0, 1 or 2 double bonds. The products are distinguished by a low content of bound glycerol and a low acid value. Removal or neutralization of the catalyst is unnecessary because, after the transesterification, the fatty acids are also present in the form of their esters.
Type:
Grant
Filed:
January 10, 1994
Date of Patent:
October 3, 1995
Assignee:
Henkel Kommanditgesellschaft auf Aktien
Inventors:
Guenther Demmering, Christian Pelzer, Lothar Friesenhagen
Abstract: Acetoglycerides are prepared in a solventless, single phase interesterification between triacetin and triglycerides bearing long C.sub.16 to C.sub.22 fatty acid residues by adding triglycerides bearing saturated C.sub.3 to C.sub.10 acid residues to the reaction mixture. The long acid residues may be hydrogenated before or after interesterification. In one embodiment, the C.sub.3 to C.sub.10 triglycerides are tripropionin, tributyrin, or mixtures of these; in another, these are triglycerides bearing C.sub.8 to C.sub.10 acid residues; and in a third, these are a mixture of tripropionin and/or tributyrin and C.sub.8 to C.sub.10 triglycerides. In preferred embodiments, the molar ratio of C.sub.16 to C.sub.22 triglycerides to triacetin and C.sub.3 to C.sub.10 triglycerides varies between 1:1 and 1:15, more narrowly between 1:3 and 1:12, and high temperatures are employed. The process diminishes catalyst use, obviates the need for high shear mixing, shortens reaction times, and simplifies purification steps.
Type:
Grant
Filed:
February 3, 1993
Date of Patent:
July 18, 1995
Assignee:
Nabisco, Inc.
Inventors:
Turiddu A. Pelloso, Allan D. Roden, Gilbert L. Boldt
Abstract: A process is disclosed for preparing fatty acid esters of short-chain monohydric aliphatic alcohols or monoalkylated diols by basically catalyzed esterification of natural, partially or totally synthetic fatty acid glycerides, as well as fatty acid glyceride-based waste products, such as used frying oils. The process is characterized in that the unpurified fatty acid glycerides, containing in particular high proportions of free fatty acids and phosphatides, (a) are esterified in one or several steps in the presence of a basic catalyst with an excess of short-chain alcohol or monoalkylated diol; (b) the glycerin phase produced after the first esterification step is at least partially added to the second or following step, after sterification has been carried out, and the mixture is stirred; (c) the glycerin phase is again separated, the supernatant fatty acid ester is cleared of excess alcohol or diol, then treated with a possibly diluted organic or anorganic acid, and if necessary filtered.
Abstract: Esters may be produced with a minimum formation of ether by-product by reacting an organic acid or ester with an alcohol at elevated temperatures in the presence of vinylaromatic polymer beads which are surface functionalized with strongly acidic functional groups, the inner volume of the polymer beads remaining unfunctionalized.
Abstract: Triglycerides, such as vegetable oils and animal fats, are esterified with alcohols to produce alcohol esters which can be used as alternative fuel sources. By-products of the transesterification reaction are stripped from the effluent of the transesterification reactor using a recovery alcohol that can be an isolated by-product of the transesterification reaction.
Type:
Grant
Filed:
July 14, 1993
Date of Patent:
June 13, 1995
Assignee:
Idaho Research Foundation
Inventors:
Narendra Bam, David C. Drown, Roger Korus, Dwight S. Hoffman, Timothy G. Johnson, Jacqueline M. Washam
Abstract: The invention relates to a process for the production of the fatty acid esters of lower monovalent alcohols by transesterification of fatty acid glycerides in the presence of basic catalysts. The process according to the invention is characterized in that the transesterification is carried out in the presence of 0.025 to 0.045 mols of an alkali or alkaline earth metal compound, preferably sodium hydroxide, potassium hydroxide, sodium or potassium alcoholate, based on 100 g of fatty acid glyceride and the subsequent purification of the fatty acid esters is effected by the addition of 0.3 to 3.0 percent of water by hydration and separation of the catalyst residues and other impurities.
Type:
Grant
Filed:
March 10, 1992
Date of Patent:
March 21, 1995
Assignee:
Vogel & Noot Industrieanlagenbau Gesellschaft m.b.H.
Abstract: A method of obtaining a fatty acid-esterified alkoxylated polyol useful as a reduced calorie fat substitute is provided. The method utilizes a C.sub.1 -C.sub.4 alkyl ester of a C.sub.8 -C.sub.24 fatty acid such as methyl stearate or methyl oleate and a short chain acid-esterified alkoxylated polyol such as the acetate of propoxylated glycerin as reactants.
Type:
Grant
Filed:
November 12, 1993
Date of Patent:
November 8, 1994
Assignees:
Arco Chemical Technology, L.P., CPC International, Inc.
Inventors:
Beth M. Handwerker, Charles F. Cooper, Bernard C. Sekula
Abstract: A convenient method of obtaining an esterified alkoxylated polyol composition containing long chain saturated linear acyl groups which avoids the use of free C.sub.20 -C.sub.24 fatty acids is provided. The method yields a reduced calorie admixture of a substantially digestion-resistant esterified alkoxylated polyol and a digestible fatty acid triglyceride.
Type:
Grant
Filed:
October 22, 1992
Date of Patent:
March 29, 1994
Assignees:
Arco Chemical Technology, L.P., CPC International Inc.
Abstract: A convenient method of obtaining a reduced calorie esterified alkoxylated polyol containing both long chain saturated linear acyl groups and shorter chain unsaturated acyl groups is provided.
Type:
Grant
Filed:
October 22, 1992
Date of Patent:
February 22, 1994
Assignees:
Arco Chemical Technology, L.P., CPC International, Inc.
Abstract: A novel method is provided for the preparation of food grade esterified propoxylated glycerin by transesterification in a solventless system by reacting at temperatures of from about 100.degree. C. to about 250.degree. C. a propoxylated glycerin having from 2 to 100 oxypropylene units per glycerin with a saturated or unsaturated C10 to C24 fatty acid ester or mixtures thereof.
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 process for converting liquid triglycerides into solid triglycerides by means of random transesterifications achieved through the use of catalytically active combinations comprising the reaction product of mixtures of dihydric and trihydric alcohols with mixtures of alkali metal hydroxides, and with ketones. The catalytically active materials can be employed in directed transesterifications in which the transesterification reaction mixture is subjected to a series of heating and cooling cycles during which higher melting fats are formed and precipitated from solution, causing an equilibrium shift that results in the formation and precipitation of still additional higher melting fats. An especially desirable catalytically active combination comprises the reaction product of 1, 2 propanediol, 1, 3 propanediol and glycerol, with sodium hydroxide and potassium hydroxide, and in a preferred embodiment, the reaction product is combined with acetone to form the catalytically active combination.
Abstract: 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:
Grant
Filed:
April 20, 1989
Date of Patent:
May 5, 1992
Assignee:
Henkel Kommanditgesellschaft auf Aktien
Inventors:
Karl-Heinz Buettgen, Bernhard Gutsche, Friedrich Hommers, Wilhelm Johannisbauer, Eberhard Peukert, Reinhold Sedelies