Abstract: A novel, chemically-modified partially hydrogenated vegetable oil (PHVO) is described. The PHVO is produced by a three-step reaction process that includes epoxidation, a ring-opening reaction, followed by esterification. The modified PHVO has improved kneadability and, if mixed with fully hydrogenated fat(s), hardness comparable to unmodified PHVO.

Abstract: Esters of organic acids are produced by a transesterification reaction by reacting a first ester with an alcohol to form a second ester in the presence of a catalyst comprising a mixture of DCC and DMAP.

Abstract: The invention relates to a method for processing mixtures of carboxylic acids obtained as hydrolysis products of suberin and cutin, particularly suberin and cutin isolated from birch bark, to give oligo- and polyesters, or corresponding ester-ethers, as well as the use of the products thus obtained as lubricants, fuel components, plasticizers, surface active agents, environmentally friendly agents for modifying wood, binders in coatings, adhesives, printing inks and composites, further in various cosmetic applications.

Abstract: A method for continuous process of transesterification of carboxylic acid esters in supercritical monovalent alcohol, wherein, accordingly formula R—OH, R is discretionary aliphatic hydrocarbon radical having 1-10 carbon atoms and in which as initial substance are used synthetic carboxylic acid esters or their compositions, for example fats and oils, which are esters of different fatty acids and glycerol. A device for continuous process of transesterification of carboxylic acid esters in supercritical monovalent alcohol, which comprises alcohol inlet (1), carboxylic acid ester inlet (2), reactant dosing unit (3), heat-exchanger (4), transesterification unit (5), tube of hot reaction yield to expansion tank (6), expansion tank (7), tube of hot reaction yield to heat-exchanger (8), reverse current tube of excess of alcohol (9), tube of cooled reaction yield to separator (10), separator (11), outlets of new ester and new alcohol (12 and 13).

Abstract: The invention relates to a process for the production of carboxylic acid esters by esterification of carboxylic acids and/or transesterification of carboxylic acid esters with alcohols in the presence of a liquid metal catalyst, characterized in that the liquid metal catalyst is the alkaline earth metal salt of a carboxylic acid.

Abstract: A process that employs a heterogeneous catalyst comprising a zinc aluminate mixed oxide and having the following formula: ZnAl2O4, xZnO, yAl2O3 in which x and y each represent a number in the range 0 to 2, and in which the zinc aluminate is more particularly of the spinel type, makes it possible, by means of C1 to C5 monoalcohols, to: transesterify vegetable or animal oils having a natural free acidity, such as unrefined degummed rapeseed, soya, sunflower oils or exotic oils of the African oil, palm nut oil or coconut oil type, which are naturally rich in fatty acids; and simultaneously esterify their free acidity; so as to use phospholipid free and/or degummed unrefined acid oil with an acid number in the range 0.5 to 20, for example 1 to 15 and preferably 2 to 12, to produce esters, for example methyl esters, for use as fuels.

Abstract: Method and apparatus for esterification of fatty acids or fatty acids contained in fats and oils with lower monovalent alcohol having 1 to 4 carbon atoms, comprising combining in a reaction section the fatty acids or fatty acids contained in fats and oils, and the alcohol to form a mixture, the combining forming enlarged interphases of the mixture by high or powerful dynamic shear forces and turbulence; at least one of strong mineral acid and acid ion exchange resin being present in the reaction section or a post-reaction section; starting esterification in the reaction section under pressure of 2 to 500 bar, and reducing pressure during the esterification so that a high interphase is maintained; and the esterification is carried out in the reaction section at a temperature of 50 to 300° C.

Abstract: This invention is a composition that includes a transesterified fatty acid ester resulting from the reaction of a fatty acid ester, in the presence of an acid, with a hydroxyl-containing compound. The fatty acid esters of the invention are selected from those with a carbon number of eight to twenty. The hydroxyl-containing compound is an alcohol having a carbon number between one and eighteen. The resulting composition is useful as a lubricant, as a heat transfer agent, as a rheological modifier and as a corrosion/moisture inhibitor, among other uses.

Abstract: This invention provides monoglycerides containing a conjugated fatty acid, and a process for producing the above described conjugated fatty acid containing monoglycerides in which all kinds of lipases can be used as catalysts. This invention relate to monoglycerides containing a conjugated fatty acid (preferably in an amount of 50% or more of fatty acids). This invention also relates to a process for producing the conjugated fatty acid containing monoglycerides, in which the conjugated fatty acid containing a free fatty acid and glycerol are subjected to the reaction of esterification, or of esterification and glycerolysis in the presence of lipase as a catalyst.

Abstract: The present invention relates to a method of producing a fatty acid ester, including reacting fat and oil with an alcohol in the presence of at least one third component, wherein the third component is in a supercritical state or subcritical state under the condition of preventing a uniform phase from forming.

Abstract: A new process for the production of linear monocarboxylic acid esters with 6 to 26 carbon atoms, by reaction of vegetable oils or animal oils that may or may not be neutral, with monoalcohols of 1 to 18 carbon atoms, uses a catalyst that is selected from among: the combinations of zinc oxides and titanium oxides; the combinations of zinc oxide, titanium oxide and alumina; the combinations of bismuth and titanium oxides; and the combinations of bismuth oxide, titanium oxide and alumina. The process makes it possible to produce directly, in one or more stages, an ester that can be used as a fuel and a pure glycerin.

Abstract: Mixtures of sorbitol fatty acid esters useful as low calorie fat substitutes are prepared through a direct esterification process. The process entails the direct esterification of sorbitol with free fatty acids, optionally in the presence of an esterification catalyst. The resulting sorbitol esters have an average degree of hydroxyl substitution ranging from about 3 to about 5.5. This partial esterification leads to a mixture of esters capable of serving as low calorie fat substitutes without undesirable physiological side effects or the need for additives. Furthermore, the direct esterification process proceeds without the need for large amounts of organic solvents or bleaching agents.

Abstract: In a process for producing fatty acid alkyl esters and glycerol comprising at least one reaction stage in which a charge comprising a vegetable and/or animal oil and an alcohol are brought into contact, in the presence of a heterogeneous catalyst, so as to obtain an effluent comprising at least alkyl esters, glycerol and alcohol, and at least one separation stage during which a separation is carried out of at least one portion of the effluent so as to separate an alcohol-rich effluent and an alkyl esters-rich effluent, at least one separation stage consists of a membrane separation using at least one alcohol-permeable membrane.

Abstract: The present invention is directed to a process of producing polyol esters possessing desirable composition and color. Preferably, such a process does not require molecular distillations or decoloration steps to yield a light-colored polyol ester composition. Materials that are dark in color are often produced during the esterification of polyols with vegetable oil fatty acids. It has been discovered that the present process yields the desired ester products that are light in color. The present process comprises an esterification of a polyol, such as propylene glycol, and a fatty acid ester, such as a vegetable oil fatty acid methyl ester, in the presence of a catalyst and borohydride, wherein a polyol ester having a Lovibond color below about 0.6 Red and below about 1.5 Yellow is produced.

Abstract: A process for producing wax ester comprising of esterifying dihydroxy fatty acid preferably dihydroxystearic acid with at least one alcohol in the presence of lipase as a catalyst which is then remove by filtration. The filtered catalyst could be reuse and provides a number of cost advantages. In the preferred embodiment of the present invention, the dihydroxystearic acid is derived from palm based oleic acid and the alcohol contains 8 to 18 carbon atoms per molecules.

Abstract: A method of minimizing or reducing the toxicity of a retinoid having a free carboxyl group is described. The method comprises the step of esterifying the carboxyl group of the retinoid with a highly sterically hindered compound, which is preferably an alcohol. The resulting retinoid esters are rendered much less toxic than the starting or parent retinoid. This process provides a retinoid ester analog of reduced toxicity so that it may be administered orally with minimal side effects and with a much greater therapeutic window.

Abstract: The method for the esterification of a fatty acid F is carried out in a column with a packing. In addition to functioning as a catalytic reactor, the packing functions as a stripping section. A heteregenous catalysis of a fatty acid is carried out with an alcohol used in the same molar ratio or in excess. A gaseous alcohol-rich counter-flow is produced in a sump of the column by vaporization. Water is removed from the reaction zone by means of the counter-flow acting as a stripping gas. The loaded stripping gas is at least partially liquefied at the head of the column. The head product is separated into a water-rich fraction as well as an alcohol-rich fraction. The alcohol-rich fraction is returned to the process as a starting material for the esterification and for the production of the stripping gas.

Abstract: Process of making alkyl-capped alkoxylated esters. More specifically, a process of making alkyl-capped alkoxylated esters that are comprised substantially of triethylene alkoxy ester and substantially free from ethylene glycol monoalkoxy monoester and diethylene glycol monoalkoxy monoester.

Abstract: Deacidified fats and/or oils are made by the process which comprises the steps of: (a) reacting a technical triglyceride having an acid value of up to about 60 and a stoichiometric excess of a lower alcohol having from 1 to 4 carbon atoms and from about 0.5% to about 5% by weight of a lipase to form a pre-esterification product having an acid value of from about 0.5 to about 10, (b) optionally removing water and unreacted alcohol from the pre-esterification product, (c) further reacting the pre-esterification product from step (a) or (b) with additional lower alcohol to form a post-esterification reaction product having an acid value of from about 0.1 to about 0.5.

Abstract: The present invention provides a method for producing a fatty acid ester inexpensively and efficiently by reacting a lipase or an intact mircroorganism containing a lipase, an oil and fat, and a linear lower alcohol in a system containing little or no solvent in the presence of water. The intact microorganism has not been treated with a solvent or the like, and is used as such, so that a fatty acid ester can be prepared in a simple manner. An oil and fat, a natural oil and fat such as a vegetable oil and fat, an animal oil and fat, as well as a waste oil thereof can be used. According to the method of the present invention, a reaction proceeds even in the presence of water, so that waste oils containing a large amount of water can be used as a raw material. Therefore, the waste oil to be dumped into the environment can be recycled, and a biodiesel fuel, which hardly pollutes the environment, can be provided at the same time.

Abstract: A method for converting free fatty acids in acid oil or acid fat into fatty acid methyl esters is disclosed. The method involves adding a small amount of methanol and an acid catalyst to the acid oil or acid fat and subjecting the mixture to conditions that allow the fatty acid methyl esters to form. A lipid phase containing the fatty acid methyl esters and triglycerides can from and be separated from the rest of the reaction mixture. The lipid phase can then be subjected to conditions suitable for converting the triglycerides into fatty acid methyl esters. The method of present invention is especially useful for a process of generating biodiesel using a starting material of vegetable and animal oils and fats that contain a relatively high level of free fatty acids.

Abstract: Processes for the synthesis of high purity fatty acid lower alkyl esters comprise the steps of: (a) converting a fatty acid source to a product mixture comprising lower alkyl esters and by-products; (b) water-washing the product mixture at elevated temperature and elevated pressure to remove by-products; and (c) fractionally distilling the water-washed product mixture to obtain high purity fatty acid lower alkyl esters. At least a portion of the fatty acids have from about 20 to about 24 carbon atoms. The high purity lower alkyl esters have an acid value no greater than about 1.0.

Abstract: A method for pretreating crude oils and fats for subsequent alkaline transesterification with primary and/or secondary alcohols. The raw oil or fat loaded with slimy substances is treated with a mixture used at 0.15 wt. % in relation to the oil or fat comprising an alcohol and concentrated acid, and preferably is subsequently rinsed with an alkaline glycerol phase arising from an alkaline transesterification reaction of the above-mentioned type. After the rinsing process, the glycerol phase which is loaded with slimy substances and soaps of free fatty acids is separated as a heavy phase of neutral oil liberated from free fatty acids.

Abstract: Disclosed are a fatty acid esters composition of a polyglycerine containing more than 70% of a fatty acid monoester which is defined by a specified analysis method, a process for the preparation thereof, a process for the preparation of a highly purified fatty esters composition of a polyglycerine, and a highly-purified fatty acid esters composition of a polyglycerine having an oxirane oxygen concentration of below 100 ppm which is defined by a specified analysis method. The fatty acid esters compositions of a polyglycerine are useful as additives for a variety of food-stuffs, additives for a variety of thermoplastic resins, and as additives for a variety of cosmetics or detergents.

Abstract: A process for producing alkyl esters useful in biofuels and lubricants by transesterifying glyceride- or esterifying free fatty acid-containing substances in a single critical phase medium is disclosed. The critical phase medium provides increased reaction rates, decreases the loss of catalyst or catalyst activity and improves the overall yield of desired product. The process involves the steps of dissolving an input glyceride- or free fatty acid-containing substance with an alcohol or water into a critical fluid medium; reacting the glyceride- or free fatty acid-containing substance with the alcohol or water input over either a solid or liquid acidic or basic catalyst and sequentially separating the products from each other and from the critical fluid medium, which critical fluid medium can then be recycled back in the process.

Abstract: Alkyl esters of fatty acids, and high purity glycerin, are produced using a process comprising a set of transesterification reactions between a vegetable or animal oil and an aliphatic monoalcohol employing a heterogeneous catalyst, for example based on zinc aluminate, the water content in the reaction medium being controlled to a value that is below a given limiting value.

Abstract: The present invention provides a method for preparing an ester of betulin at the 3-position, e.g., betulin-3-acetate, including the selective alcoholysis of a betulin-3,28-diester, e.g., betulin-3,28-diacetate; a method for preparing betulin-3-acetate including (1) acetylating betulin to provide betulin-3,28-diacetate and (2) the alcoholysis of betulin-3,28-diacetate to provide betulin-3-acetate; and a method for preparing betulinic acid (1) acetylating betulin to provide betulin-3,28-diacetate, (2) the alcoholysis of betulin-3,28-diacetate to provide betulin-3-acetate, (3) oxidizing betulin-3-acetate to provide betulinic aldehyde-3-acetate, (4) oxidizing betulinic aldehyde-3-acetate to provide betulinic acid-3-acetate, and (5) deprotecting betulinic acid-3-acetate to provide betulinic acid.

Abstract: Process of making alkyl-capped alkoxylated esters. More specifically, a process of making alkyl-capped alkoxylated esters that are comprised substantially of triethylene alkoxy ester and substantially free from ethylene glycol monoalkoxy monoester and diethylene glycol monoalkoxy monoester.

Abstract: Method for the preparation of an enantiomerically enriched ester, in which a mixture of the enantiomers of the corresponding secondary alcohol is subjected, in the presence of an acyl donor, to an enantioselective conversion in the presence of a racemisation catalyst upon which the ester is formed and an acyl donor residue is obtained, and in which the acyl donor residue is irreversibly removed from the phase in which the enantioselective conversion takes place. Preferably the enantioselective conversion is carried out enzymatically and a transfer hydrogenation catalyst is used as racemisation catalyst. The secondary alcohol can be formed in situ from the corresponding ketone, in the presence of a hydrogen donor. It is also possible to use a mixture of the secondary alcohol and the corresponding ketone as substrate. Preferably the acyl donor is chosen so that the acyl donor residue is converted in situ into another compound and/or the acyl donor residue is removed via distillation under reduced pressure.

Abstract: The invention provides reaction mixtures comprising polyols, triglycerides, base initiators and phase-transfer catalysts for performing transesterification reactions. The reaction product comprises a mixture of polyol monoesters, polyol diesters, triglycerides and glycerol.

Abstract: A method for making alkylesters, or methylester specifically, such as biodiesel, from an oil source is described. The method involves converting the free fatty acids of the oil source into a mixture of mono-, di-, and tri-glycerides and subsequently transesterifying the newly formed glycerides as well as the originally present glycerides into fatty acid alkyl esters.

Abstract: A process for producing a fatty acid ester with a high yield from an oil or fat and an alcohol which comprises reacting an oil or fat with an alcohol in the presence of a solid base catalyst under conditions in which at least one of the oil or fat and the alcohol is in a supercritical state at a temperature exceeding 260° C.

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: The present invention provides a reactive diluent composition which overcomes drawbacks of both the radical-cure and the cationic-cure reactive diluents and can be applied in a broad variety of uses such as paints, inks, adhesives, pressure sensitive adhesives, surface-modifiers, and molding materials; a curable resin composition containing the same; an activated energy ray-curable resin composition; and an activated energy ray-curable ink composition for ink-jet printing. A reactive diluent composition comprising a vinyl ether group-containing (meth)acrylic ester represented by the following general formula (1): CH2═CR1—COO—R2—O—CH═CH—R3  (1) wherein R1 represents a hydrogen atom or a methyl group; R2 represents an organic residue of 2 to 20 carbon atoms; R3 represents a hydrogen atom or an organic residue of 1 to 11 carbon atoms and a hydroxyl group-containing polymerizable compound and/or divinyl ether.

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.

Abstract: The present invention relates to cranberry seed oil derivatives derived by the reaction of dimethicone copolyol and cold pressed cranberry seed oil. The choice of cold pressed cranberry seed oil as a raw material in the preparation of the compounds of the present invention is critical, since it has been found that the cold pressed cranberry seed oil contains antioxidants, antimicrobial compounds and which when reacted with a water soluble or water dispersible silicone result in products that deliver said actives to the skin and hair, resulting in protection of the skin and hair from environmental factors such as acid rain, ozone attack and UV degradation.

Abstract: A process for the esterification of a mixture of fatty acids and triglycerides. The process comprises forming a single phase solution of fatty acids and triglyceride in an alcohol selected from methanol and ethanol, the ratio of said alcohol to triglyceride being 15:1 to 35:1. The solution further comprises a co-solvent in an amount to form the single phase. In a first step, an acid catalyst for the esterification of the fatty acids is added. After a period of time, the acid catalyst is neutralized and a base catalyst for the transesterification of triglycerides is added. After a further period of time, esters are separated from the solution.

Abstract: The present invention provides a reactive diluent composition which overcomes drawbacks of both the radical-cure and the cationic-cure reactive diluents and can be applied in a broad variety of uses such as paints, inks, adhesives, pressure sensitive adhesives, surface-modifiers, and molding materials; a curable resin composition containing the same; an activated energy ray-curable resin composition; and an activated energy ray-curable ink composition for ink-jet printing.

Abstract: 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.

Abstract: The invention relates to a process for manufacturing non-oily emollients with a molecular weight below about 600 Dalton, preferably below 550 Dalton, and still more preferably below about 450 Dalton, based on alcohol and fatty acid esters (wax-esters), which consists of the following steps: a) interesterification of the triglycerides contained in a fatty material by a primary alcohol, in the presence of a catalyst; b) elimination of the catalyst; c) distillation of the residual alcohol preferably in the presence of a bleaching agent followed by elimination of the bleaching agent; d1) either frigelisation of the preferably bleached residue such that residual glycerides are at least partially crystallized, followed by elimination of said crystallized residual glycerides, d2) or hydrogenation of the residue, preferably bleached.

Abstract: A fatty acid ester prepared by treating botanical seeds or fruits with a monohydric alcohol having 1 to 10 carbon atoms under pressure at a temperature of at least 180° C., preferably under supercritical conditions.

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 provides a process for producing lower alkyl fatty esters from fatty acids and lower alcohols, wherein lower alkyl fatty esters are produced in higher yield with a reduction in the amount of the remaining fatty acids. The process of the present invention comprises bringing fatty acids into contact with gaseous lower alcohols in fixed bed(s) charged with a weakly acidic solid catalyst by countercurrent operation, by co-current operation and subsequent countercurrent operation or by pseudo-countercurrent operation, thus feeding and reacting the fatty acids and lower alcohols in fixed-bed reactor(s) charged with a weakly acidic solid catalyst to produce lower alkyl fatty esters.

Abstract: 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.

Abstract: The present invention provides a method for preparing an ester of betulin at the 3-position, e.g., betulin-3-acetate, including the selective alcoholysis of a betulin-3,28-diester, e.g., betulin-3,28-diacetate; a method for preparing betulin-3-acetate including (1) acetylating betulin to provide betulin-3,28-diacetate and (2) the alcoholysis of betulin-3,28-diacetate to provide betulin-3-acetate; a method for preparing betulinic acid from betulin-3-acetate including (1) acetylating betulin to provide betulin-3,28-diacetate, (2) the alcoholysis of betulin-3,28-diacetate to provide betulin-3-acetate, (3) oxidizing betulin-3-acetate to provide betulinic aldehyde-3-acetate, (4) oxidizing betulinic aldehyde-3-acetate to provide betulinic acid-3-acetate, and (5) deprotecting betulinic acid-3-acetate to provide betulinic acid.

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.

Abstract: Fatty acid sorbitan esters by direct reaction of sorbitol with fatty acid using a phosphorus oxyacid, including reducing phosphorus oxyacid particulary phosphouous acid, catalyst system and an alkali or alkali earth metal base, particulaly oxide, hydroxide or carbonate, in an axid:base molar ratio of 0.9:1 to 1.7:1, at a calalust concentration of 1.5 to 30%, particularly 3 to 12%, by weight of sorbitol can have lower color than products of prior commercial bulk processes even without the use of activated carbon and product bleaching typically used previously. The esters can be further reacted with alkylene oxide to make desivatives, particularly polysorbates. The esters and polyalkyleneoxy detivatives are useful surfactants in various application. Products of low color made without using activated carbon or bleaching are attractive for personal care applications.

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 invention relates to a method for obtaining fatty acid esters and fatty acids, preferably unsaturated fatty acid ethyl esters, from biological sources by continuous, combined in-situ extraction, reaction and chromatography. The invention is characterized in that simultaneously and in the same location, in the presence of a compressed gas and an 0.5-5 % stream of lower alcohols as modifiers and in the presence of an inert catalyst, the fatty acids are fully transesterified from their native fatty acid sources, which are selectively desorbed and eluated in the conditions specified above.

Abstract: Process for the preparation of dimeric fatty acid C1-4 alkyl esters comprising the steps of A) reacting a soybean oil condensate obtained from the deodorization of refined soybean oil and which contains less than 30% by weight of free and esterified oleic acid based on the total weight of free and esterified fatty acids in said condensate, with a C1-4 alkanol in the presence of a zinc oxide catalyst to convert free fatty acids and fatty acid glyceride esters to fatty acid C1-4 alkyl esters; B) removing excess C1-4 alkanol, volatile reaction by-products, water, and the zinc oxide catalyst from the resulting reaction mixture; C) heating the reaction mixture from step B) under vacuum to obtain a distillate of fatty acid C1-4 alkyl esters; D) separating the distillate from step C) into a fraction containing mostly C16-18 saturated fatty acid C1-4 alkyl esters and a second fraction containing mostly C16-18 unsaturated fatty acid C1-4 alkyl esters wherein the oleic acid C1-4 alkyl ester content is less than abo