Abstract: Disclosed herein are a cation-exchanged clay mineral comprising a swelling clay mineral with the cations between layers substantially replaced by low-valence metal amine complexes and/or low-valence metal ammine complexes, and a packing material for chromatography using the same. Use of the packing material provides a sharp peak with respect to a highly unsaturated compound. Since the packing material is unlikely to be influenced by a solvent, it is usable for a long time with good stability.

Abstract: A process of selectively separating and purifying eicosapentaenoic and docosahexaenoic acids or the esters thereof from a mixture comprising a highly unsaturated fatty acid or the derivative thereof, which comprises the steps of: flowing an aqueous medium comprising a silver salt through a column filled with a diatomaceous earth to carry the silver salt on the diatomaceous earth; flowing a solvent solution of a mixture comprising the highly unsaturated fatty acid or the derivative thereof through the silver salt-carried diatomaceous earth in the column; and flowing a developing solvent through the column.

Abstract: The present invention relates to a process for preparing calorie cooking and frying oils, containing nondigestable polyol polyesters, and having improved color and improved stability against hydrolysis during frying. The process comprises, as a first step, treating a crude polyol polyester with an ion exchange ligand in an aqueous phase to convert diavalent metal soaps present in the crude polyol polyester to monovalent soaps. The monovalent soaps and ion exchange ligands are then removed from the treated polyol polyester to provide a cooking and frying oil which contains less than about 550 ppb divalent metal ions. Said oil, when further processed according to conventional industry standards will have a free fatty acid content of less than about 500 ppm. Preferably, the cooking and frying oils prepared according to the process of the present invention will further have a Lovibond red color of less than about 6, preferably less than about 4.

Abstract: Eicosapentaenoic acid or its ester is separated and purified from a mixture containing a highly unsaturated fatty acid or its ester effectively at low cost by a process, which comprises developing the mixture by a mixed solvent of an ether solvent and a hydrocarbon solvent, using a column filled with a silica gel having a particle diameter of 1-100 micrometers.

Abstract: A process and composition for removing trace contaminants from glyceride oils utilizes a metal-substituted silica xerogel having a pH of at least 7.5 to adsorb at least a portion of the contaminants. The process of the invention includes contacting a glyceride oil with such an adsorbent and then separating the adsorbent from the contaminant-depleted glyceride oil, for example, by filtration. The composition of the present invention includes a metal-substituted silica xerogel having a pH of at least 7.5 and an organic acid blended with the xerogel. Preferably, the organic acid is citric acid. Contaminants which can be removed from glyceride oils during the refinement of such oils by the adsorbent include phospholipids, soaps, detrimental metals, and chlorophyll.

Abstract: Sulfur and soap contaminants are removed from carboxylic acid esters by a process comprising the steps of: (1) contacting a carboxylic acid ester with an aqueous base at a temperature of from about 225° F. to about 280° F. while removing water to form a dry, crude ester; (2) contacting the dry, crude ester with an absorbent selected from the group consisting of silica gel, hydro-silica gel and mixtures thereof; (3) separating the absorbent from the ester.

Abstract: A novel process for the selective elimination of fatty acid compounds containing carbon-carbon double bonds in trans configuration from a substrate containing cis- and trans-isomers of said fatty acid compounds, by selective adsorption by a microporous zeolite material is disclosed. The pore size and shape of usable zeolite materials enable differentiation between cis- and trans-isomers of unsaturated fatty acid chains. The zeolite materials used have a selectivity ratio &agr;trans/cis higher than 1.00; this ratio is defined based on the elution properties of cis and trans double bond containing fatty acid methylesters dissolved in n-hexane during a column chromatography experiment with the zeolite material as the stationary phase and n-hexane as the mobile phase.

Abstract: The present invention relates to improved methods for refining vegetable oils and byproducts thereof. This invention also relates to an improved process for deodorizing lecithin. The invention additionally relates to deodorized lecithin and deodorized vegetable oil obtained by improved processes of the invention. In an organic acid refining process, vegetable oil is combined with a dilute aqueous organic acid solution and subjected to high shear to finely disperse the acid solution in the oil. The resulting acid-and-oil mixture is mixed at low shear for a time sufficient to sequester contaminants into a hydrated impurities phase, producing a purified vegetable oil phase. In a lecithin deodorizing process, a phosphatide concentrate is contacted with steam in a dryer operating at a pressure below 50 mm Hg and at a temperature of less than about 150° F. to form lecithin containing no more than about 0.5 percent by weight water.

Abstract: A method for providing a purified conjugated linoleic acid (CLA) is disclosed. The purified conjugated linoleic acid (CLA) is formed by separating by liquid chromatography a 9-cis, 11-trans octadecadienoic acid formed by a novel synthesis of reacting an ester of ricinoleic acid with a tosyl chloride or a mesyl chloride to form a tosylate or mesylate of an ester of ricinoleic acid, and reacting the tosylate or mesylate of an ester of ricinoleic acid with diazabicyclo-undecene. Reacting an ester of ricinoleic acid with a tosyl chloride or a mesyl chloride to form a tosylate or mesylate of an ester of ricinoleic acid, and reacting the tosylate or mesylate of an ester of ricinoleic acid with diazabicyclo-undecene forms a 9-cis, 11-trans octadecadienoic acid having a purity greater than 50%, and separating by liquid chromatography forms a 9-cis, 11-trans octadecadienoic acid having a purity greater than 90%. In one aspect, the liquid chromatography uses a strong acid macroreticular ion exchange resin.

Abstract: A process for purifying alkoxylated fats by treatment with a solid substance, wherein a mixture of aluminum oxide and a silicate is employed as solid substance.

Abstract: Disclosed are compositions, suitable for use in the purification of edible or inedible oils, of agglomerated particles of at least one minus ten micron bleaching clay, wherein said agglomerated particles are microspheres having an average diameter of at least about 10 microns as well as a process for preparing microspheres suitable for use as bleaching earths having improved filtration characteristics by agglomerating a mixture consisting ofi) at least one minus ten micron bleaching clay,ii) at least one liquid medium, andiii) at least one binder material,wherein said mixture is agglomerated under conditions which produce microspheres having an average diameter of greater than about 10 microns. Also disclosed is a process for purification of edible and inedible oils which comprises mixing one or more oils with the compositions described above and then physically removing said composition from the oil.

Abstract: An adsorbent is described based on an inorganic support material with exchangeable mono- and divalent cations, characterized by the fact that the specific surface of the support material is >100 m.sup.2 /g, its cation exchange capacity is>30 mg-equiv/100 g, its pore volume is>0.15 m/g, the pH value of an aqueous suspension of 8 g of support material in 100 mL of H.sub.2 O is<7.5 and that at least 60, preferably at least 70% of the exchangeable mono- and/or divalent cations are exchanged by cations acting as Lewis acids, preferably Al.sup.3 + cations.

Abstract: A mixture of fatty acids or their esters derived from natural oils and fats including eicosapentaenoic acids or their derivatives is precision distilled under a high vacuum using a plurality of distillation columns, three distillation columns or more in particular, in order to acquire a fraction consisting mainly of fatty acids of carbon number 20 or their esters, which is then subjected to a column chromatography with a reversed-phase distribution system. Eicosapentaenoic acids or their esters, which is useful for preventing or treating thrombus, with a purity as high as 99% and above and with a recovery rate 55% or above, is produced.

Abstract: A method of refining and manufacturing a fat and oil containing polyunsaturated fatty acids which prevents production of peculiar fishy smells when such a fat and oil is added to food materials and while it is stored by preventing oxidation of PUFA's and restraining conversion of odor-emanating precursors into odor-emanating substances. A fat and oil, such as a marine animal oil, containing polyunsaturated fatty acids with 18 or more carbon atoms and three or more double bonds such as EPA and DHA is alkali refined and bleached. The thus alkali refined and bleached fat and oil is refined by bringing 100 parts by weight of it into contact for 10 minutes or more at 5.degree.-80.degree. C. with not less than 0.1 part by weight of powdered or granulated diatomaceous earth formed by calcining with a flux added such as sodium carbonate or sodium chloride. The fat and oil thus obtained is filtered and deodorized by steam distillation under vacuum.

Abstract: A process for recovering at least one of purified polyunsaturated fatty acids (PUFA) and polyunsaturated fatty acid mixtures from a feed composition includes a step of (i) treating the composition by either (a) stationary bed chromatography or (b) multistage countercurrent column fractionation in which a solvent is a fluid at supercritical pressure, and recovering at least one PUFA-enriched fraction. The process also includes a step of (ii) subjecting the fraction recovered in the treating step to further fractionation by simulated continuous countercurrent moving bed chromatography, and recovering at least one fraction containing the purified PUFA or the PUFA mixture.

Abstract: Disclosed is a process for recovering an edible oil, such as soybean or canola oil, from an adsorbent material, such as a bleaching agent, by contacting a feed of the adsorbent material containing the edible oil with a normally gaseous solvent, such as liquid propane, for a time sufficient to extract a substantial portion of the oil from the adsorbent material, before the oil degrades to an appreciable extent.

Abstract: A process for purifying crude ester containing residual metallic catalyst is described. The process comprises (a) adding to a crude ester product an amorphous silicon dioxide adsorbent capable of adsorbing dissolved metallic catalyst; (b) heating the combination at a temperature of between about 80.degree. C. and about 130.degree. C.; and (c) separating the ester from the adsorbent by filtration, such that residual metallic catalyst is retained on the adsorbent.

Abstract: The invention improves on the amorphous adsorbent-based processes by overcoming the soap leaching problem without using filtration before vacuum bleaching. For fatty materials containing only minor amounts of phospholipid and trace metal impurities, simply vacuum drying at least a portion of the soap-containing fatty material prior to contacting with the amorphous adsorbent eliminates the soap leaching problem. For fatty materials containing higher amounts of phospholipid and trace metals, simply using an acid pretreatment and the vacuum drying step eliminate the soap leaching problem.

Abstract: A new process has been developed for preparing high purity neem seed extract by adsorbing aqueous solutions of neem seed extract containing azadirachtin onto a macroporous polymeric adsorbent followed by desorption using a solvent. The resulting extract, optionally formulated, is a useful insecticide for the control of foliar pests.

Abstract: A chromatographic process for deacidification of vegetable oils at ambient temperature. According to the process, which can be retrofitted into deacidification operations using miscella refining or solvent extraction, crude vegetable oil is dissolved in a solvent such as isopropyl alcohol and passed through a column of activated alumina (aluminum oxide) at room temperature. The process, which eliminates physical contact between both oil and an alkaline reagent and oil and water, simplifies subsequent bleaching processes by also removing some color pigments. The spent alumina can be reactivated by washing it with a dilute solution of sodium hydroxide or potassium hydroxide.

Abstract: Carboxylic acids are sorbed from aqueous feedstocks into an organic liquid phase or onto a solid adsorbent. The acids are freed from the sorbent phase by treating it with aqueous alkylamine thus forming an alkylammonium carboxylate which is dewatered and decomposed to the desired carboxylic acid and the alkylamine.

Abstract: Fatty acid esters, particularly those suitable for use in foods and cosmetics, are decolored by passing a solution of a fatty acid ester dissolved in an apolar solvent through particulate montmorillonite which is in admixture with particulate silica gel and/or active carbon. The solution passed through the column is obtained and the solvent is eliminated from the ester.

Abstract: Light-colored ester sulfonates can be obtained by sulfonation of fatty acid lower alkyl esters and subsequent working up providing fatty acid esters having a low content of oxo compounds and unsaturated compounds are used in the sulfonation stage.

Abstract: A method for recovering at least one unsaturated fatty acid having sixteen or more carbon atoms and/or at least one compound of such a fatty acid from a mixture derived from vegetable, animal or marine sources is provided. Fatty acids and/or fatty acid compounds of the mixture, in free acid or esterified form, are passed into a mobile phase of liquid carbon dioxide in a column over a stationary phase. The stationary phase contains a support and a material bound to the support which contains at least one free electron pair and/or multiple bond. After eluting any saturated fatty acid or fatty acid compound of the same number of carbon atoms from the column, the unsaturated fatty acid and/or fatty acid compound is recovered in pure chemical form or as an enriched mixture.

Abstract: A three step process for regenerating spent bleaching clays and acid-activated smectite catalyst granules includes: (1) an extraction step to remove a majority of entrained oil, preferably about 75% to about 95% by weight of the entrained oil, when regenerating bleaching clays; (2) an oxidation step to remove the majority of remaining carbonaceous adsorbates which are not removed by the preceding extraction step, and (3) an acid wash step to restore the acidity normally associated with fresh acid-activated bleaching clays. The features of steps 2 and 3 may be combined into a single step by using an appropriate oxidant, for example, a source of acidic protons, such as peracetic acid.

Abstract: Methods for frying food including supplying cooking fluid to a fryer apparatus, frying food in the cooking fluid so that used cooking fluid including degradation products including surfactants are produced therein and food residue accumulates in the fryer apparatus, adding the treatment compound capable of selectively reducing the amount of the surfactants to the used cooking fluid, and permitting the treatment compound to remain within the fryer apparatus and settle upon the food residue while continuing the food frying process.

Abstract: A method for the adsorptive purification of vegetable and/or mineral oils and fats works with a multi-stage counter flow process. At least a part of the solid phase leaving the first separating stage is mixed in batches or continuously with a part of the purified oil or fat leaving the last separating stage. The mash thereby obtained is fed to a subsequent filter.

Abstract: A modified physical adsorption process is described in which small quantities of caustic are added to glyceride oils, fatty chemicals or wax esters having an FFA level sufficient to create about 20 to 3,000 ppm soaps. The soaps, together with impurities, are removed by adsorption onto amorphous silica.

Abstract: A process for removal of sulfur-containing compounds from fatty materials is disclosed, in which the fatty material is contacted with a silica hydrogel. Use of this adsorptive process prior to hydrogenation improves oil quality and decreases hydrogenation times.

Abstract: Glycolipids and phospholipids are obtained by dissolving a mixture of complex lipids in a solvent to form a solution and then passing the solution over a boric acid gel. Glycolipids are retained in the gel, and phospholipids are eluted through the gel.

Abstract: The invention relates to a process for refining glyceride oil comprising the steps of contacting the oil with amorphous silica, wherein said silica is selected from the group of precipitated amorphous silicas having a surface area of at least 400 m.sup.2 /g in pores with a diameter from at least 2 nm. Preferably said precipitated amorphous silicas have a pore volume in the range of about 1.3 to 2.5 ml/g, in pores having a pore diameter in the range of 3.6 to 1000 nm.

Abstract: The present invention relates to a process for the regeneration of spent bleaching earth, comprising an oxidative heat treatment in which the amount of oxygen supplied exceeds the stoichiometrical requirement of complete oxidation of all organics present in the spent bleaching earth, wherein the spent bleaching earth and the oxygen are blown through a stationary fluidized bed of inert granulate material. The stationary fluidized bed should be as high as to limit the temperature in the freeboard to less than 1000.degree. C. As a matter of fact, it has been found that, if the fluidized bed is not high enough, the oxygen required to burn off the organics content of the spent bleaching earth would blow out the powdered bleaching earth from the bed at the stage of incomplete oxidation of the organics present on the earth, resulting in an uncontrolled temperature rise in the freeboard and local overheating of the bleaching earth.

Abstract: Adsorbents are provided which are suitable for use in the removal of contaminants selected from the group consisting of free fatty acids, soaps, phosphorus, metal ions and color bodies. The adsorbents comprise inorganic porous supports selected from the group consisting of substantially amorphous alumina, diatomaceous earth, clays, magnesium silicates, aluminum silicates and amorphous silica, treated with a base in such a manner that at least a portion of said base is retained in at least some of the pores of the support to yield base-treated inorganic porous adsorbents. Processes for removing free fatty acids, etc., from glyceride oils using these adsorbents are also provided.

Abstract: The invention relates to a method for refining glyceride oil, comprising the steps of:i) acidifying the oil with an acid;ii) partially neutralizing the acidified oil with alkali;iii) contacting the partially neutralized oil with an amorphous silica; andiv) removing solids from the glyceride oil.Preferably, water is removed from the mixture comprising the glyceride oil and the amorphous silica before any solids are removed.

Abstract: There is disclosed a process for preparing refined palm oil by treating a fat or oil containing palm oil as a main ingredient with an activated clay having 250 to 350 m.sup.2 /g of a specific surface area and containing 0 to 3% by weight of ferric oxide and 70 to 90% by weight of silicon oxide. According to the process of the present invention, refined palm oil which hardly causes browning even upon heating and color reversion can be obtained.

Abstract: A method for refining and fractionation of palm oil is disclosed. In this method, palm oil or palm fractionated oil which has been treated by physical refining is treated with an adsorbent, followed by subjecting it to dry fractionation. An apparatus for refining and fractionation of palm oil comprising means for treating palm oil or palm fractionated oil with an adsorbent and dry fractionation means connected thereto is also disclosed.

Abstract: Adsorbents comprising amorphous silicas with effective average pore diameters of up to about 5000 Angstroms are useful in processes for the removal of soaps and phospholipids (along with associated metal ions) from caustic treated, primary centrifuged, water-wash centrifuged or caustic refined glyceride oils.

Abstract: A process for refining organic-solvent containing crude polyol fatty-acid polyester reaction product, including the steps of distilling the crude reaction product to substantially remove the organic solvent, and subsequently subjecting the distilled reaction product to a bleaching treatment. The process allows an economic use of bleaching agents while achieving good color and color stability of the refined product.

Abstract: A two-stage separation process for separating highly unsaturated triglycerides from an interesterification reaction product by sequential chromatographic separations wherein triglycerides are separated from saturated fatty acids in the first stage and unsaturated fatty acids are recovered in the second stage for recycle to the interesterification reaction zone. In a preferred embodiment using silica gel and silicalite in the two stages, respectively, and heptanone as desorbent in both stages, triglyceride product is removed as the first stage raffinate and the unsaturated fatty acid recycle product stream is removed as the raffinate in the second stage. In another embodiment, using silicalite adsorbent in both stages and 2-heptanone and acetone in the first and second stages, respectively, saturated fatty acids are removed as the extract in the first stage and triglycerides and unsaturated fatty acids are separated as raffinate product and extract product for recycle, respectively.

Abstract: Adsorbents suitable for use to remove aromatic or polyaromatic hydrocarbons from liquids such as oils may be produced from an acid-activated siliceous clay containing adsorbed oil by treating to carbonize the oil and to activate the carbon so produced on the surface of the clay. The carbonization and activation steps may be conducted by heating in the presence of an activating agent which may be zinc chloride. Preferably zinc chloride activated material is subsequently steam-treated.The invention is particularly useful to reduce the content of hazardous polyaromatic hydrocarbons, such as benzo(a)pyrene, from edible oils.

Abstract: Methods for frying food including supplying cooking fluid to a fryer apparatus, frying food in the cooking fluid so that used cooking fluid including degradation products including surfactants are produced therein and food residue accumulates in the fryer apparatus, adding the treatment compound capable of selectively reducing the amount of the surfactants directly to the used cooking fluid, and permitting the treatment compound to remain within the fryer apparatus and settle upon the food residue while continuing the food frying process.

Abstract: The separation of free fatty acids from triglycerides is performed by an adsorptive chromatographic process in liquid phase with silica gel as the adsorbent. A ketone, having from 3 to 8 carbon atoms, such as 2-heptanone, an ester or an ether can be selected as the desorbent.

Abstract: The separation of unsaturated triglycerides on the basis of degree of unsaturation is achieved by an adsorptive chromatographic process in liquid phase with silane- or alcohol-treated silica gel as the adsorbent. Desorbents in the separation process include ketones, having from 3 to 8 carbon atoms, low molecular weight esters, having from 3 to 8 carbon atoms or p-cymene, or mixtures thereof, alone or mixed with a hydrocarbon diluent. The preferred temperature in the separation column is from 120.degree.-150.degree. C.

Abstract: The present invention contemplates a method for treating oils having undesirable color impurities and an oil bleaching composition suitable for use in this method. The method comprises contacting the oil with the oil bleaching composition for a time period sufficient to reduce the amount of color impurities of the oil. The oil bleaching composition includes a neutral bleaching clay and a chelating polycarboxylic acid. The spent bleaching composition resists spontaneous combustion.

Abstract: 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.

Abstract: Substantially pure stearidonic acid is isolated from a mixture of polyunsaturated fatty acids by fractionating at 25% to 35% by weight solution of fatty acids by high-performance reverse-phase liquid chromatography using a mobile phase of 75% to 95% by weight methanol and 25% to 5% by weight water. The isolated stearidonic acid is used to prepare pharmaceutical compositions which are administered to treat cardiovascular and thrombo-embolic diseases associated with platelet aggregation.

Abstract: Generally in accordance with the present invention, methods are provided for removing cholesterol from edible triglyceride oils. In this regard, animal fats typically contain cholesterol predominantly in the form of free cholesterol, as well as minor amounts of cholesterol esters of fatty acids such as cholesteryl oleate or palmitate. The present methods may be used to remove cholesterol from both animal and vegetable triglyceride oils, including, but not limited to, butterfat, beef tallow, fish oil, lard, soybean oil, canola oil, corn oil, sunflower oil, cottonseed oil, safflower oil, olive oil and peanut oil.