EP0349606A1 - Procede d'obtention d'acide oleique de grande purete par hydrolyse d'huile de graines de tournesol - Google Patents

Procede d'obtention d'acide oleique de grande purete par hydrolyse d'huile de graines de tournesol

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Publication number
EP0349606A1
EP0349606A1 EP88909701A EP88909701A EP0349606A1 EP 0349606 A1 EP0349606 A1 EP 0349606A1 EP 88909701 A EP88909701 A EP 88909701A EP 88909701 A EP88909701 A EP 88909701A EP 0349606 A1 EP0349606 A1 EP 0349606A1
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EP
European Patent Office
Prior art keywords
oleic acid
oleic
oil
range
triglycerides
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Application number
EP88909701A
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German (de)
English (en)
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EP0349606B1 (fr
Inventor
Melody A. Wilk
Richard Yodice
Eileen T. Boone
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Lubrizol Corp
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Lubrizol Corp
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
    • C11C1/04—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis
    • C11C1/045—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis using enzymes or microorganisms, living or dead

Definitions

  • This invention relates generally to the field of methods for producing cis-9 octadecenoic acid, i.e. oleic acid. More particularly, the invention relates to the enzymatic hydrolysis of high oleic sunflower seed oil to. produce a highly pure form of oleic acid as well as highly pure oleic acid compositions derived from such hydrolysis.
  • Oleic acid or cis-9-octadecenoic acid is a monounsaturated fatty acid present within natural fats and oils or biological lipids.
  • Oleic acid is CH 3 (CH 2 ) 7 (CH:CH) (CH ) COOH and is also known as red oil.
  • Oleic acid is a very important substance in both industry and biology. Cleaner, purer products are inherently safer when used in connection with products such as pharmaceuticals; and purer starting materials allow for the production of purer fine chemical derivatives.
  • Oleic acid is most generally obtained from high-pressure steam fat splitting processes using tallow as the starting material. When produced by such fat splitting processes, oleic acid is not generally obtained in a pure form. Highly purified oleic acid is both colorless and odorless and has excellent stability with respect to oxidative degradation. These properties make • it extremely useful in connection with a large number of food and pharmaceutical products. Pure oleic acid can be used safely due to its excellent physical, chemical and physiological properties. Due to such properties oleic acid is actively and widely utilized in the fine chemical or specialty chemical fields. For example, oleic acid is extensively used in pharmaceuticals, cosmetics and foods and has found application in biochemical areas in conne ⁇ ction with biosensors and biosurfactants.
  • Oleic acid has also found application in connection with electronics for the stimulation of biological function as well as a number of other quickly developing high technology fields. Many uses for oleic acid require that the oleic acid be very pure, and commercially available oleic acid generally includes fatty acid homologs having different carbon numbers and double bond numbers. In addition, commercially available oleic acid often contains various minor impurities. Oleic acid compositions which are impure have properties and characteristics which make them
  • a specific method and composition for the hydrolysis of triglycerides is disclosed within U.S. Patent 4,259,440 issued March 31, 1981 to Miles Laboratories Incorporated.
  • the method includes the steps of adding lipase and cholesterol esterase to a triglyceride in combination with a glycerol assay system and determining the amount of triglycerides present based on the amount of glycerol produced.
  • Other patents which refer generally to the enzymatic hydrolysis of triglycerides are referred to within patent number 4,259,440.
  • U.S. Patent 4,275,011 discloses a process for the interesterification of oils and fats comprising treating such oils and fats with a water-soluble microbial enzyme.
  • the microbial enzyme is absorbed on an inert, powdered, water insoluble dispersing agent. Thereafter, the enzyme which is absorbed onto the inert substrate is recovered from the reaction medium.
  • a method of producing a high purity oleic acid by the enzymatic hydrolysis of high oleic sunflower seed oil involves obtaining sunflower seed oil which is extremely high in its oleic content.
  • Sun ⁇ flower seed oils contain triglycerides.
  • the high oleic sunflower seed oils such as used in connection with the present invention have an oleic content of 60% or more, more preferably 80% or more, still more preferably 88% or more, and most preferably about 95%.
  • Such high oleic oils are subjected to enzymatic hydrolysis by contacting the triglycerides with a hydrolase enzyme to provide a reaction product which includes a high purity oleic acid composition.
  • the reaction medium resulting from the enzymatic hydrolysis contains the oleic acid, glycerol, and a number of contaminant acids.
  • high oleic sunflower seed oil "high oleic sunflower oil” and “high oleic oil” will be used synonymously to mean an oil extracted from the seed of a sunflower plant which oil contains triglycerides which have fatty acid moieties and wherein 60% or more of such moieties are oleic acid moieties (preferably 80% or more, more preferably 88% or more, most preferably about 95%) and further wherein the ratio of any linoleic acid moieties to oleic acid moieties is 0.25 or less, i.e.
  • oleic moieties linoleic moieties- is 1: (0.25 or less) , preferably 1:0..09 or less and most preferably 1: (0.09-0.01) .
  • high purity oleic acid compo ⁇ sitions and the like refers to oleic acid compositions obtained by using a "high oleic sunflower oil” starting material and carrying out the processing as disclosed and described herein in connection with the present invention.
  • a typical high purity oleic acid composition of the present invention would have approximately the following physical characteristics:
  • a primary object of the present invention is to provide a method for producing a high purity oleic acid composition by the enzymatic hydrolysis of high oleic sunflower seed oil.
  • Another object of the present invention is to provide such a method for the enzymatic hydrolysis of high oleic sunflower seed oil whereby different enzymes are utilized to efficiently remove all the oleic acid from the triglycerides within the sunflower oil.
  • An advantage of the present invention is that the hydrolysis of the triglycerides within the sunflower oils can be carried out in an energy efficient manner.
  • a feature of the present invention is that the reaction product resulting from the hydrolysis of the high oleic sunflower seed oil is a high purity oleic acid composition having a variety of uses within high techn ⁇ ology fields.
  • Another feature of the present invention is that it combines technological advancements from the unrelated fields of (1) agricultural plant development; (2) biochemical enzymatic hydrolysis and (3) chemical engineering purification procedures respectively, by combining advancements in (1) plant breeding based on cytoplasmic male sterility techniques; (2) the use of specific lipases to hydrolyze the triglycerides of oils; and (3) chemical reactions and physical separation procedures specifically adapted for purifying oleic acid.
  • oleic acid and the high purity oleic acid compositions Before the present method for producing cis-9- octadecenoic acid (hereinafter oleic acid and the high purity oleic acid compositions) is disclosed and described, it is to be understood that this invention is not limited to the particular methods or compositions described as such methods and compositions may, of course, vary. It is also to be understood that the terminology used herein if for the purpose of describing particular embodiments only, and is not intended to be limiting since the scope of the present invention will be limited only by the appended claims.
  • the present invention is a unique process which provides compositions of highly pure oleic acid by combining technological achievement in basically unrelated areas of science.
  • Modern plant breeding technology is used to obtain seeds containing an oil of particularly high oleic content.
  • the sunflower (genus Helianthus) is second only to the soybean as a source worldwide for vegetable oil.
  • sunflower (genus Helianthus)
  • the sunflower is second only to the soybean as a source worldwide for vegetable oil.
  • Average sunflower yields in the United States range from about 1200 to about 1400 kilograms per hectare, with the oil content from harvested seed averaging about 40 to 45% on a dry weight basis.
  • Increasing both the oil content (as a percentage of total plant weight) and the yield of these sunflower plants are major objectives of plant breeding projects which the present invention utilizes as source material.
  • CMS cytoplasmic male sterility
  • Fick "Breeding and Genetics” in Sunflower Science and Technology, pages 279-338 (J.F. Carter, ed. 1978) which is incorporated herein by reference for its disclosure of cytoplasmic male sterility breeding and genetic fertility restoration techniques in connection with sunflowers.
  • CMS cytoplasmic male sterility
  • the production of a particular sunflower hybrid using CMS is described within U. S. Patent 4,378,655 which is incorpo ⁇ rated herein by reference for its disclosure of particular sunflower hybrids and means of producing such hybrids.
  • cytoplasmic male sterility is now the technique of choice for producing sunflower plants with substanti ⁇ ally non-functional pollen for subsequent use in producing hybrids
  • other methods also described in U. S. Patent 4,378,655 are available. These methods include the use of complete or partial genetic sterility based on the presence of recessive genes and the application of chemical gametocides. Plants having a high level of self-incompatibility can also be used in a method for hybrid production.
  • Sunflower oil is comprised primarily of palmitic, stearic, oleic and linoleic acids, with oleic and linoleic accounting for about 90% of the total fatty acid content of the conventional sunflower seed oils.
  • sunflower seed oil is known to contain 13 varieties of fatty acids including linoleic, oleic, palmitic, stearic, linolenic, palmitoleic, arachidic, margaric, palmitic and behenic. (See T. Cuprina et.al. The Relative Amount of Fatty Acids in Sunflower Oil of Certain Inbred Lines and in Hybrids of Sunflowers, Institute for Agriculture and
  • the unsaturated acids have one, two or three free bonds, e.g. respectively oleic, linoleic and linolenic.
  • a high linoleic acid concentration is desirable in sunflower oil used in soft margarines and salad dressings, high oleic acid content is preferred for many other applications.
  • a high oleic sunflower seed oil is desirable with respect to the present invention which involves the production of a high purity oleic acid.
  • the purity of the oleic acid with respect to its lack of linoleic acid, increases the oxidative stability of the product obtained.
  • the oxidative stability of conventional crude sunflower oil derived from seed grown in southern climates is nearly twice that of the crude oil extracted from northern-grown sunflower seeds.
  • the terms "cultivar” and “variety” are used synonymously to refer to a group of plants (e.g., Pervenets) within a species
  • a variety used in connection with the present invention may show overall variation between individuals within the variety, based primarily on Mendelian segregation of traits among the progeny of succeeding generations.
  • a "line”, as distinguished from a “variety” denotes a group of plants which display less variation among individuals, generally (although, not exclusively) , by virtue of several generations of self-pollination.
  • a “line” is defined for the purposes of the present disclosure, sufficiently broad to include a group of plants vegetatively propagated from a single parent plant using tissue culture techniques. The use of such lines to develop new hybrids is described within U. S.
  • Patents 4,326,358 and 4,381,624 the contents of which are incorporated herein by reference for disclosure of such tissue culture techniques.
  • a variety or a line is considered "true breeding" for a particular trait if it is genetically homozygous for that trait to the extent that, when the true breeding variety or line is self-pollinated, a significant amount of independent segregation of the trait among the progeny is not observed.
  • the various fatty acids such as stearic acid, oleic acid and linoleic acid, are characteristic of the oil of a given variety of seed. Such acid contents may be expressed as a percentage of the total fatty acid content of the trigylceride making up the oil.
  • the di ensionless ratios of linoleic acid content to oleic acid content mentioned below are calculated by dividing the linoleic acid percentage of total fatty acid moieties on the triglyceride by the like percentage of oleic acid moieties. Thus, smaller numbers represent a larger percentage of oleic acid relative to linoleic acid.
  • an oil derived from a sunflower seed wherein the triglycerides of the oil have an oleic acid moiety content of greater than about 60% preferably 80% relative to the total fatty acid moiety content of the triglycerides present within the sunflower seed oil.
  • the ratio of the amount of the linoleic acid in the seed to the amount of oleic acid in the seed is less than approximately 0.25, i.e. the ratio of oleic moiety to linoleic moiety is 1:0.25 preferably 1:0.09 or less.
  • the ratio of the amount of linoleic acid moiety in the seed to the amount of oleic acid moiety in the seed is in the range of about 0.01 to about 0.09, i.e. the ratio of oleic:linoleic is 1: (0.09-0.01).
  • the select ⁇ ivity of the enzyme is often not sufficiently specific to differentiate between linoleic and oleic acids containing the same number of carbons and an overlapping unsaturated position.
  • the sunflower seed oil is obtained from a substantially homogeneous assemblage of sunflower seeds. Any particular sunflower seed within the assemblage may well contain higher or lower amounts of oleic acid and different ratios of linoleic to oleic acid. However, the. resulting statistical mixture of triglycerides obtained from the substantially homogeneous assemblage of sunflower seeds provides an oil which on average contains 60% or more oleic, preferably 80% or more, more preferably 88% or more oleic most preferably 95% or more oleic with the ratio of the linoleic to the oleic of less than 0.25, preferably less than 0.09 and more preferably in the range of about 1: (0.09-0.01) .
  • the oil is taken from the acid moieties of the oil will vary as will the relative amounts of those acid moieties.
  • a typical oil used in connection with the present invention would include the following acid moieties in the given percent amounts:
  • a variation ⁇ 10% would be within the scope of the present invention.
  • the high oleic sunflower oil preferably used in connection with the present invention is most generally obtained from the breeding techniques as disclosed in
  • the distillation steps required vary depending on the chain length of the fatty acid being isolated. As the chain length increases, the amount of temperature and vacuum required to carry out distillation also increases which further increases the expense due to the additional energy requirements. Further, as the temperature of distillation is increased, reactions can occur among the fatty acids themselves resulting in polymerization and the oxidative degradation. This decreases the yield of the • fatty acid obtained from such techniques. In addition to the occurrence of polymerization reactions, some fatty acids isomerize at their double bonds creating large amounts of isomerized fatty acids which decrease the yield of the fatty acid product obtained.
  • the present invention does not make use of any high pressure, high temperature techniques in order to separate the fatty acids from the trigylcerides within the oils.
  • the present invention utilizes enzymatic hydrolysis to carry out decomposition of the fats and oils.
  • the enzymatic hydrolysis reactions carried out in accordance with the present invention are very selective and have a very low energy requirement.
  • the selectivity of the reaction increases the amount of a particular fatty acid removed from the triglyceride, thus, increasing the purity of the resulting yield.
  • high temperatures are not required during the hydrolysis and are actually undesi ⁇ rable, fatty acids are not lost by polymerization or isomerization reactions which occur under high temperature.
  • the ability of enzyme derived from specific microbes to hydrolyze a material is often specific to the material. Accordingly, the enzymatic hydrolysis reaction used in connection with the present invention are carried out only on high oleic sunflower seed oils which have been described above. To obtain the present invention, particular reaction conditions necessary to enzymatically hydrolyze such high oleic sunflower seed oil have been carefully studied with regard to the type and amount of enzyme, the pH of the reaction mixture, the type and amount of additives, the temperature and the amount of water necessary to obtain both a high purity oleic acid composition and a high yield. Adjustment of these parameters can increase the percent of hydrolysis and/or •selectivity of the reaction.
  • the enzymes used in connection with the present invention can be divided into different categories as follows:
  • High oleic sunflower seed oil used in connection with the present invention is comprised of trigylcerides having the following general structural formula (I) :
  • R, R' and R" are hydrocarbon moieties of the acid moieties, 80% or more of which are oleic acid moieties. As indicated above, preferably 88% or more of the acid moieties are oleic and most preferably about 95% are oleic moieties.
  • the enzyme will separate all of the fatty acid moieties at all three positions and leave a mixture of glycerol and the separated fatty acids.
  • the site-specific enzyme generally removes the fatty acid moiety from the two primary positions of the triglyceride.
  • a 100% efficient reaction of such a site-specific moiety with such a triglyceride would remove two-thirds of the fatty acid moieties.
  • the enzyme will react with fatty acid positions wherein particular fatty acids are located (the acid generally being recognized by a particular unsa ⁇ turated position) .
  • the enzyme could react with only oleic fatty acid moieties which have an unsaturated position at the delta nine carbon.
  • fatty acid-specific moieties might also react with other non-oleic moieties which also have an unsaturated position at the ninth carbon.
  • one embodiment of the invention involves the use of the high oleic sunflower seed oil starting material in combination with enzymatic hydrolysis techniques to obtain a high yield of oleic acid in a relatively " high purity.
  • the resulting hydrolyzed product is comprised of fatty acids and glycerol with the glycerol being soluble within the aqueous phase.
  • the aqueous phase is then separated away, leaving a relatively high yield of a high purity oleic acid composition.
  • the present invention involves the use of hydrolase., enzymes, and more specifically water soluble lipases.
  • hydrolase enzymes
  • microbes from which are derived non site-selective lipases used in connection with the present invention:
  • Candida rugosa (cylindracae) Chromobacterium viscosum Humicola lanuginosa
  • Some particular combinations of enzymes are found to be particularly useful in connection with the present invention are derived from the following combinations of microbes.
  • microbial enzyme sources/ animal sources may be used in connection with this invention such as Porcine pancreatic lipase, Bovine pancreatic lipase and Porcine liver esterase.
  • the amount of the enzyme utilized depends on the amount of the triglyceride to be hydrolyzed.
  • the amount of the enzyme is expressed in units (U) of activity in connection with the hydrolytic decomposition of the triglyceride.
  • the amount of enzyme utilized varies depending on the particular enzyme used. Since the present invention only applies enzymes to high oleic sunflower seed oils, the amount and type of enzyme does not vary substantially depending upon the oil being hydrolyzed.
  • Porcine pancreatic 100-1000 U/m.eq. 340-3,400 U/g.
  • Geotrichum 85.0 U/g or less.
  • Mucor 85.0 U/g or less.
  • Aspergillus 34 U/g or less.
  • the enzymatic hydrolysis reaction carried out in connection with the present invention is preferably carried out in the presence of water in an amount in the range of about 0.5 to 1.5 times the amount of the high oleic sunflower seed oil.
  • the water must be present in a sufficient amount to allow for the hydrolysis to effi ⁇ ciently proceed. However, the inclusion of too much water can also decrease the efficiency of hydrolysis and make it difficult to effectively remove and dispose of the aqueous phase of the reaction medium.
  • the enzymatic hydrolysis reactions of the present invention take place at the oil/water interface. The relative amounts of oil and water varies with each system and must be adjusted in order to obtain the best results. In general the water/oil ratio is
  • the temperature is generally about 38°-40°C with 1, 3 specific enzymes, more generally the temperature can range from 20°C to 60°C.
  • the pH of the enzymatic reaction mixture affects the hydrolysis.
  • the hydrolytic reaction yields a carboxylic acid which is not water soluble.
  • the reaction can be carried out in the presence of other additives although other additives are not generally useful in connection with the present invention.
  • the enzymatic hydrolysis of the present invention is preferably carried out in a temperature, range of about 20°C to 60°C, more preferably, about 30°C to 50°C.
  • the temperature must generally be kept above 20°C in order to allow for the reaction to proceed quickly enough to economically carry out the procedure and must be carried out below 60°C in order to avoid deactivation of the enzyme prior to its interaction with the trigylceride. It is also desirable to continually agitate the reaction mixture in order to promote the enzymatic hydrolysis of the triglycerides.
  • the relative amounts of oil/water vary with other factors such as the amount of agitation, temperature and the enzyme source. Clearly, the amount of oil/water interface is affected by agitation and to some extent by temperature.
  • the oil to water ratio is preferably 1: (1 ) , (more preferably 1: 1.2) the temperature is preferably 30°C to 50°C and agitation is generally carried out at sufficient speed in order to keep the oil and water phases in a homogeneous dispersion.
  • the following examples are provided so as to provide those of ordinary skill in the art with a complete disclosure and description of how to make the oleic acid compositions and carry out the hydrolysis reactions of the invention and are not intended to limit the scope of what is regarded as the invention.
  • a high oleic sunflower seed oil is obtained from a substantially homogenous assemblage of seeds.
  • the high oleic sunflower seed oil as defined above includes triglycerides wherein the oleic moieties make up at least 60% of the fatty acid moieties on the tri ⁇ glyceride. Further, the resulting high oleic sunflower seed oil has a specifically defined ratio amount of linoleic to oleic acid.
  • the specific purity of the oleic acid varies somewhat depending on the starting high oleic sunflower oil used.
  • the oleic acid composition derived from utilizing the high oleic sunflower seed oil and subjecting the oil to hydrolysis to obtain oleic acid in accordance with the above description is considered to be the broadest aspect of the present invention.
  • this oleic acid composition obtained from the high oleic sunflower seed oil can be further purified by physical and chemical procedures which will now be described in detail.
  • the reaction product separates away into two phases with the upper phase being comprised of the fatty acids removed from the triglycerides and the lower aqueous phase being comprised largely of water having dissolved therein glycerol and certain contaminants from the high oleic sunflower seed oil.
  • the first step in purification of the enzymatic hydrolysis product is to separate away the lower aqueous phase containing the water having the water soluble compounds therein.
  • the remaining upper phase will contain a very high concentration of oleic acid.
  • the characteristics of the oleic acid composition will vary depending on the starting sunflower seeds used. The following is typical of such a high oleic acid composition:
  • the oil might also include some metals such as Ca, Bu, Zn, and Fe in small amounts, e.g. 1-100 pp .
  • Each of the above physical and chemical characteristics might vary to different degrees, but in general might vary ⁇ 10%.
  • the upper phase will include contaminant fatty acids such as linoleic acid as well as other fatty acids which having longer and/or shorter chains than oleic acid as well as greater and lesser degrees of unsaturation.
  • contaminant fatty acids can then be separated away by utilizing one or more chemical or physical separation techniques.
  • chemical separation techniques such as those described within U.S. Patent 4,601,856 incorporated herein by reference for its disclosure of chemical oleic acid purification techniques.
  • the high oleic acid composition of the invention is obtained as the upper phase resulting from the enzymatic hydrolysis process described above. This high oleic acid composition includes several different types of fatty acids and other contaminants as indicated above.
  • fatty acids having different chain lengths and fatty acids having different degrees of unsaturation it is possible to separate away fatty acids having different chain lengths and fatty acids having different degrees of unsaturation in order to further purify the oleic acid composition. More specifically, those fatty acids having more or less than 18 carbon atoms or more or less than one unsaturated bond can be separated away from the oleic acid which contains 18 carbon atoms and a single unsaturated bond.
  • a high oleic fatty acid composition of the present invention is winterized by subjecting the composition to low temperature treatments. By reducing the temperature gradually until crystallization begins, it is possible to separate away those fatty acids which contain higher degrees of saturation than oleic acid. Accordingly, by reducing the temperature gradually a point will be reached wherein fatty acids such as stearic and palmitic acid will crystallize and precipitate within the composition. These fatty acids can then be removed to provide a further purified high oleic acid composition.
  • Polar solvents such as acetone and methanol allow saturated acids such as stearic acid and palmitic acid to crystallize almost quantitatively while the unsaturated acids such as oleic acid remain dissolved within a solvent. Accordingly, separation can be accomplished by including acetone and or methanol in the high oleic composition in an amount sufficient to bring about crystallization of the contaminant palmitic and stearic acids within the composition. After the crystallization occurs filtration can be carried out in order to remove the crystallized contaminant palmitic and stearic acids. In general the acetone or methanol solvents are added to the composition in a ratio of 3-4 liters of solvent per liter of fatty acid.
  • the temperature is reduced to bring about crystallization.
  • the temperature is reduced to -10 to -15°C and filtration is carried out utilizing a vacuum rotary filter after crystallization occurs.
  • the filter can then be sprayed with cold acetone to remove any free oleic acid.
  • Solvents are removed from the oleic acid composition by flash evaporation and steam stripping.
  • it is possible to purify oleic acid compositions by chilling the fatty acid composition in water which contains a detergent such as sodium decyl sulfate. Crystals formed within the aqueous dispersion are coated with a film of detergent. These crystals remain in the water phase when the mixture is centrifugally separated. The oil phase is free of crystals and moisture.

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Abstract

Procédé de production d'acide oléique de grande pureté par hydrolyse enzymatique. Ce procédé consiste à obtenir de l'huile de tournesol à haute teneur en acide oléique, contenant des triglycérides possédant des moitiés d'acide gras de l'acide oléique dans une proportion égale ou supérieure à 60 %, de préférence égale ou supérieure à 80 %, le rapport entre la moitié d'acide linoléique et la moitié d'acide oléique étant inférieur à environ 0,25, de préférence inférieur à 0,09. On soumet à hydrolyse enzymatique l'huile obtenue à partir de l'huile de tournesol à haute teneur en acide oléique en la mettant en contact avec des enzymes d'hydrolase et/ou différentes combinaison d'enzymes d'hydrolase dans un milieu aqueux à une température comprise entre 20 et 60 °C et un pH entre environ 4,5 et environ 10. On agite l'huile, l'enzyme d'hydrolase et l'eau de sorte que l'hydrolyse se produise au niveau de l'interface huile-eau et que les moitiés acides des triglycérides se séparent. On laisse se former une couche d'acide oléique qui se sépare du milieu aqueux et celui-ci est ensuite séparé pour obtenir de l'acide oléique de grande pureté.
EP88909701A 1987-10-13 1988-10-07 Procede d'obtention d'acide oleique de grande purete par hydrolyse d'huile de graines de tournesol Expired - Lifetime EP0349606B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US10824187A 1987-10-13 1987-10-13
US108241 1987-10-13
PCT/US1988/003480 WO1989003419A1 (fr) 1987-10-13 1988-10-07 Procede de production de preparations a base d'acide cis-9-octadecenoique

Publications (2)

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EP0349606A1 true EP0349606A1 (fr) 1990-01-10
EP0349606B1 EP0349606B1 (fr) 1995-12-06

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EP (1) EP0349606B1 (fr)
JP (1) JPH02501622A (fr)
AT (1) ATE131206T1 (fr)
AU (1) AU615969B2 (fr)
DE (1) DE3854761T2 (fr)
WO (1) WO1989003419A1 (fr)

Families Citing this family (9)

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GB8729890D0 (en) * 1987-12-22 1988-02-03 Unilever Plc Improvements in & relating to fat processes
DE4124248A1 (de) * 1991-07-22 1993-01-28 Henkel Kgaa Verfahren zur selektiven fettspaltung, dazu geeignete lipasemischung und mikroorganismus
US5470741A (en) * 1992-07-22 1995-11-28 Henkel Corporation Mutant of Geotrichum candidum which produces novel enzyme system to selectively hydrolyze triglycerides
FR2772374B1 (fr) * 1998-04-20 2001-01-26 Toulousaine De Rech Et De Dev Composition lubrifiante tensioactive
US7592015B2 (en) 1999-06-04 2009-09-22 Consejo Superior De Investigaciones Cientificas Use of high oleic high stearic oils
EP1554925A1 (fr) 1999-06-04 2005-07-20 Consejo Superior de Investigaciones Cientificas Produits alimentaires et cosmétiques renfermant des huiles à forte teneur en acide oléique et forte teneur en acide stéarique
US6388113B1 (en) 1999-06-04 2002-05-14 Consejo Superior De Investigaciones Cientificas ( Csic) High oleic/high stearic sunflower oils
US20220053777A1 (en) * 2013-06-24 2022-02-24 Dennis B. Jenkins Non-toxic ant-repelling gel
US11858872B2 (en) * 2021-03-30 2024-01-02 ExxonMobil Technology and Engineering Company High yield jet fuel from mixed fatty acids

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AU615969B2 (en) 1991-10-17
EP0349606B1 (fr) 1995-12-06
JPH02501622A (ja) 1990-06-07
DE3854761D1 (de) 1996-01-18
DE3854761T2 (de) 1996-04-25
AU2612988A (en) 1989-05-02
ATE131206T1 (de) 1995-12-15
WO1989003419A1 (fr) 1989-04-20

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