US2596344A - Fractionation process - Google Patents

Fractionation process Download PDF

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Publication number
US2596344A
US2596344A US4556448A US2596344A US 2596344 A US2596344 A US 2596344A US 4556448 A US4556448 A US 4556448A US 2596344 A US2596344 A US 2596344A
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United States
Prior art keywords
urea
fraction
compounds
mixture
chain
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English (en)
Inventor
Herbert A Newey
Edward C Shokal
Theodore F Bradley
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Shell Development Co
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Shell Development Co
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Publication date
Application filed by Shell Development Co filed Critical Shell Development Co
Priority to US4556448 priority Critical patent/US2596344A/en
Priority to GB2089049A priority patent/GB665248A/en
Priority to NL148190A priority patent/NL148190B/xx
Priority to FR994189D priority patent/FR994189A/fr
Priority to DEP52479A priority patent/DE883605C/de
Priority to BE490746D priority patent/BE490746A/fr
Application granted granted Critical
Publication of US2596344A publication Critical patent/US2596344A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B13/00—Recovery of fats, fatty oils or fatty acids from waste materials
    • C11B13/005—Recovery of fats, fatty oils or fatty acids from waste materials of residues of the fabrication of wood-cellulose (in particular tall-oil)
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
    • C11B7/0008—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents
    • C11B7/0025—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents in solvents containing oxygen in their molecule
    • 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
    • C11C1/005—Splitting up mixtures of fatty acids into their constituents
    • 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
    • C11C1/007—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids using organic solvents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes

Definitions

  • This invention is concerned with a new process for fractionating mixtures of certain polar organic compounds. Specifically, it is concerned with the fractionation of such mixtures as 'vegetable oil acids or their derivatives.
  • the fractionation of naturally-occurring mixtures of organic materials is necessary for their application in specific industries. For example, use of vegetable oils and the like in coating compositions requires removal of the less suitable components, which in most cases are the relatively saturated species. l-leretofore, fractionation of vegetable oils has been eiiected by such means as fractional distillation or fractional crystallization, either of which methods. may be combined with solvent extraction. Alternatively, the latter process alone has been used. These previously known processes vary considerably in their relative efficiency and especially in economy.
  • This invention is based upon the discovery that mixtures of straight-chain polar organic compounds may be effectively separated into fractions respectively richer and poorer in the chemically less saturated components by clathrate compound formation with urea.
  • a mixture of straight-chain polar organic compounds containing components having varying degrees of chemical unsaturation has urea admixed therewith, as more fully described hereinafter.
  • the relatively more saturated components form crystalline clathrate compounds with urea, while the relatively less saturated components remain unchanged.
  • mixtures of fatty acids may be fractionated by the preferential formation of crystalline clathrate compounds between urea and acids having relatively low unsaturation.
  • th potential drying characteristics of vegetable-and-animal-oil acids may be substantially improved by treatment of such mixtures of acids with urea so as to extract the acids having a low degree of unsaturation, i. e., less than two double bonds, thus leaving as a rafiinate the more unsaturated members having the best potential drying characteristics.
  • the process of the present invention may be applied with equal or even greater effectiveness to the mixtures of esters of the above acids, especially when the esters are formed by esterification with a straight-chain monohydric alcohol. It may also be applied to fatty alcohols comprising mixtures of varied degrees of unsaturation. Branched-chain or cyclic compounds will not usually form clathrate compounds with urea of the type described.
  • Th term clathrate compounds has been coined recently as a generic name for molecular complexes such as those formed by urea, as described hereinafter. While the formation of clathrate compounds of urea and straight-chain hydrocarbons had been discovered, no adequate explanation was available of how the two molecules were united in the absenc of chemical reaction. In the investigations from which the present invention resulted, X-ray and crystallographic studies have elucidated the structure to adequately explain the topography of the complex molecules and to describe the types of materials which undergo clathrat formation with urea.
  • th clathrate compounds comprise spiral-like arrangements of urea molecules which bind within the spiral a second organic compound.
  • the X-ray data have shown that urea apparently forms a spiral having a critical inner diameter and that this diameter does not appreciably vary with conditions such as temperature or environment.
  • an organic substance In order to form a clathrate compound therewith, an organic substance must have an unbranched configuration except for terminal atoms. Th crosssectional diameter of a straight-chain organic 3 7 compound primarily depends upon bond angles between carbon atoms or other atoms comprising the straight chain and upon the diameter of substituent groups or atoms attached to the chain.
  • Branched-chain compounds for example, have cross-sectional diameters larger than that which will permit the compound to fit into the urea spiral. Hence, these substances do not undergo clathrate formation with urea.
  • Straight-chain organic compounds form clathrates with urea with increasing reluctance as their degree of unsaturation increases.
  • Typical vegetable oils containing acids which may be treated in this way include soybean, cottonseed, linseed, cocoanut, perilla and hemp seed oils, as well as oiticica and tung oils.
  • Fish oils such as sardine, menhaden, Whale oil and fish liver oils also provide suitable acids for use in the present process.
  • Other sources comprise tall oil, isomerized linseed and soybean oils, as well as dehydrated castor oil. While the process of the present invention may be employed in the fractionation of other mixtures, as described hereinafter, it will be described with particular reference to acids obtained from the above typical sources.
  • Linseed oil comprises primarily a mixture of glycerides of fatty acids having a typical analysis as follows:
  • the mixtureof fatty acids may be treated in the absence of any diluent or solvent; however, it is usually preferable to include a diluent such as a ketone or alcohol.
  • a diluent such as a ketone or alcohol.
  • Suitable diluents include especially methyl isobutyl ketone and methyl ethyl ketone.
  • Alcohols which are preferred include those having four and five carbon atoms and may be primary, secondary or tertiary in structure. Mixtures of such solvents may be employed.
  • the use of equal amounts of amyl alcohols with methyl isobutyl ketone has been found especially useful for the subject process. This particular type of mixture permits rapid separation of the raffinate from the crystalline clathrate compounds.
  • the term rafilnate is used in the present case to describe the unaffected fractions of the mixtures treated with urea.
  • Urea may be dissolved in a suitable solvent or may be employed in the crystalline state. Preferably, it is dispersed in an aqueous medium and, still more preferably, is employed as a solution which is initially saturated at the temperature of the reaction. The concentration of urea in its solvent may be adjusted to. obtain selective fractionation, since it has been found that solutions having less than a saturation content of urea have a diminished reactivity with some components of the mixtures treated.
  • the ratio of urea to the mixture of organic compounds is an additional factor which may be varied in controlling the degree and type of the resulting fraction.
  • the examples which follow principally show the use of equal molar amounts of urea and vegetable oil. As the amount of urea with relation to the vegetable oil acids is reduced, the process becomes increasingly selective. Since the clathrate compounds being considered normally comprise one mol of urea for each carbon atom in the extracted component, the molar ratio of urea to the active fraction of the vegetable oil should be quite large. Even under the most favorable conditions, it is a preferred practice to employ a large excess of urea when a maximum removal is desired. However, a reduced quantity of urea may be employed in controlling the removal of specific fractions.
  • the process generally comprises mixing the fatty acids with urea in a reactor column by means of rapid stirring, allowing the mixture to remain in the reactor for a time sufficient for complete reaction and then transporting the reacted mixture to a separator.
  • the separator may comprise a settling tank, filter or centrifuge,
  • the raffinate separates from the crystalline clathrate compounds and the residual urea solution.
  • the mixture of dilute urea solution and clathrate compounds may be heated to a temperature' of 80-125 0., in order to decompose the clathrate and regenerate both fatty acids and urea therefrom.
  • a convenient process step comprises permitting decomposition to take place in the presence of the dilute urea solution, whereupon the regenerated urea redissolves in the urea solution and is recirculated for additional fractionations.
  • the crystalline clathrate compounds are separated from the liquid components of the mixture, namely, the dilute urea solution and the composedte fraction.
  • the clathrate compounds may be regenerated by the use of heat or by such methods as steam distillation or treatment with hot organic solvents or water.
  • urea solutions tend to promote rapid corrosion of iron equipment and even of fixtures composed of cement. This appears to be caused by oxidation, which apparently is accelerated in the presence of urea.
  • the equipment may be protected by blanketing with an inert gas, such as nitrogen, by including corrosion inhibitors in the mixture, such as ammonium phosphate and ammonium chromate, or by coating the equipment with resins or corrosion-resistant metals.
  • Particular species of fatty acids which readily form clathrate compounds include especially the saturated straight-chain fatty acids having four to fifty carbon atoms, such as butyric, caprylic, myristic and stearic acids and the ,mono-olefinic acids such as oleic acid.
  • Unsaturated fatty acids which form clathrate compoundswith urea. with some reluctance under the conditions described include especially linolenic and elaeostearic acids; specific esters which readily form clathrate compounds with urea are methyl stearate and ethyl palmitate.
  • Methyl isobutyl ketone was removed from the oily layer by distillation to 110 C. at 0.5 mm. mercury pressure. The railinate was recovered as an oily layer from the dilute urea solution obtained in the original filtration. Methyl isobutyl ketone was removed therefrom as described above. The iodine values of the fatty acids, regenerated from the clathrate compounds and of the rafiinate were determined and are reported below. Methyl esters of each of the three types of fatty acid mixtures were treated in a similar manner. The results obtained are given in the table which follows.
  • Linseed oil acids were reduced to the unsaturated straight-chain alcohols by use of metallic sodium and methyl isobutyl carbinol (Ind. Eng. Chem. 39 55-62 (1947) This reduction retains the unsaturation present in the linseed acids.
  • the distilled alcohols boiling between l64182 C. at 0.8-1.7 mm. were used in the following ex-- traction.
  • a urea complex could be formed from a fraction of methyl esters of linseed oil acids that had two or more double bonds per molecule.
  • the rafiinate from the urea extraction of methyl linseedate (Example 4) was used in this experiment.
  • the iodine value was 224, indicating that the fraction was predominately the ester of linoleic acid (iodine value, 172.8) and linolenic acid (iodine value, 261.3)
  • the crystalline complex was stirred in 1500 m1. of warm Water. Th upper layer which separated was washed with water and dried by filtering through paper. Weight of extract, 50 g.; Wijs iodine value,-73,9.
  • a process for the separation of mixtures of straight-chain polar organic compounds bearing an unbranched hydrocarbon chain having differing degrees of unsaturation comprising contacting said mixture at a temperature of 0-? 5 C. with urea whereby crystalline complexes are formed between urea and a fraction A of said mixture, a fraction B of said mixture being inert towards urea under the contacting conditions, separating the resulting crystalline complexes from said fraction B, and regenerating polar compounds of fraction A from the separated complexes, fraction A being enriched in relatively less unsaturated straight-chain polarorganic compounds bearing an unbranched hydrocarbon chain and fraction B being enriched in relatively more unsaturated straight-chain polar organic compounds bearing an unbranched hydrocarbon chain bearing a polar substituent of the same chemical classes that borne by the compounds of fraction A.
  • a process for the fractionation of mixtures of fish oil fatty acids having differing degrees of saturation comprising contacting said mixture at a temperature of 0-75 C. with urea, whereby crystalline complexes are formed between urea and a fraction A of said mixture, a fraction B of said mixture being inert toward urea under the contacting conditions, separating the resulting crystalline complexes from said fraction B and regenerating fatty acids from the separated complexes, fraction A being enriched in relatively less unsaturated fatty acids and fraction B being enriched in relatively more unsaturated fatty acids.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Analytical Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
US4556448 1948-08-21 1948-08-21 Fractionation process Expired - Lifetime US2596344A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US4556448 US2596344A (en) 1948-08-21 1948-08-21 Fractionation process
GB2089049A GB665248A (en) 1948-08-21 1949-08-11 Improvements in or relating to the fractionation of mixtures of organic compounds of differing degrees of unsaturation
NL148190A NL148190B (nl) 1948-08-21 1949-08-17 Separator voor galvanische elementen en galvanisch element, dat een dergelijke separator bevat.
FR994189D FR994189A (fr) 1948-08-21 1949-08-18 Procédé de fractionnement de mélanges de composés organiques
DEP52479A DE883605C (de) 1948-08-21 1949-08-20 Verfahren zur Fraktionierung von Mischungen organischer Verbindungen durch Behandlung mit Harnstoff
BE490746D BE490746A (fr) 1948-08-21 1949-08-20 Procédé de fractionnement.

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US4556448 US2596344A (en) 1948-08-21 1948-08-21 Fractionation process

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BE (1) BE490746A (fr)
DE (1) DE883605C (fr)
FR (1) FR994189A (fr)
GB (1) GB665248A (fr)
NL (1) NL148190B (fr)

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2681333A (en) * 1954-06-15 Gorin
US2681334A (en) * 1954-06-15 Formation of urea complexes with
US2700664A (en) * 1950-11-17 1955-01-25 Phillips Petroleum Co Separation of organic compounds by adduct formation
US2717890A (en) * 1951-07-27 1955-09-13 American Cyanamid Co Talloil separation by urea extraction
US2732413A (en) * 1956-01-24 Process for the recovery of benzene by
US2756252A (en) * 1952-07-28 1956-07-24 Union Oil Co Adducts of substituted phosphoryl amides
US2756222A (en) * 1952-06-17 1956-07-24 Swern Daniel Purification of long-chain vinyl esters and ethers
US2759915A (en) * 1956-08-21 Gorin
US2759916A (en) * 1954-02-01 1956-08-21 Socony Mobil Oil Co Inc Urea-nitrile complexes
US2760974A (en) * 1952-07-28 1956-08-28 Union Oil Co Separation of phosphoryl amide adducts of benzene dicarboxylic acids
US2782112A (en) * 1954-01-04 1957-02-19 Allied Chem & Dye Corp Herbicide
US2785151A (en) * 1952-10-14 1957-03-12 Manuel H Gorin Process for treating tall-oil with urea, and particularly a new form of expanded urea
US2798102A (en) * 1952-10-25 1957-07-02 Union Oil Co Method of decomposing werner complex clathrates
US2798103A (en) * 1953-07-20 1957-07-02 Union Oil Co Separation of aromatic compounds by clathrate formation with a werner complex
US2798891A (en) * 1954-02-01 1957-07-09 Union Oil Co Separation of organic compounds by forming clathrates with werner complexes
US2800466A (en) * 1952-09-30 1957-07-23 Rosenstein Ludwig Process for treating a mixture of saturated and unsaturated fatty acids with expanded urea
US2838480A (en) * 1952-07-14 1958-06-10 Swern Daniel Separation of mixed fatty acids
US2849511A (en) * 1953-05-25 1958-08-26 Union Oil Co Separation of organic compounds
US2905730A (en) * 1954-09-02 1959-09-22 Phillips Petroleum Co Method of forming a clathrate complex
US2905662A (en) * 1956-05-11 1959-09-22 American Cyanamid Co Preparation of tetracycline-urea compound
US2935457A (en) * 1956-08-16 1960-05-03 British Petroleum Co Production of hard and flexible microcrystalline waxes
US2959580A (en) * 1956-10-17 1960-11-08 Univ Minnesota Formation of inclusion compounds
US3082228A (en) * 1959-12-18 1963-03-19 Escambia Chem Corp Method for producing monoesters of polyunsaturated fatty acids
US3167513A (en) * 1958-03-07 1965-01-26 Lever Brothers Ltd Bleaching compositions
EP0178442A1 (fr) * 1984-10-10 1986-04-23 Societe Des Produits Nestle S.A. Procédé d'enrichissement sélectif en acides gras polyinsaturés delta-6 d'un mélange contenant des acides gras delta-6 et delta-9, fractions enrichies obtenues et leur utilisation
US4601856A (en) * 1984-06-12 1986-07-22 Nippon Oil And Fats Company, Limited Method of purifying oleic acid
EP0619362A3 (fr) * 1993-04-06 1995-11-29 Theodor Wimmer Procédé de fractionnement de mélanges d'acides gras.
US20060281814A1 (en) * 2002-08-06 2006-12-14 Paul Angers Conjugated linolenic acids and methods for commerical preparation and purification
US8598379B2 (en) 2009-11-05 2013-12-03 Purdue Research Foundation Method of lowering the cloud point of fatty acid esters

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102016008113A1 (de) * 2016-06-30 2018-01-04 Kd Pharma Bexbach Gmbh Verfahren zur Trennung von mehrfach ungesättigter Kohlenwasserstoffe, insbesondere Omega-3-und/oder Omega-6-Fettsäure(n), aus einem Flüssigkeitsgemisch

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2520716A (en) * 1950-08-29 Method of separating organic com

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2520716A (en) * 1950-08-29 Method of separating organic com

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2681334A (en) * 1954-06-15 Formation of urea complexes with
US2732413A (en) * 1956-01-24 Process for the recovery of benzene by
US2759915A (en) * 1956-08-21 Gorin
US2681333A (en) * 1954-06-15 Gorin
US2700664A (en) * 1950-11-17 1955-01-25 Phillips Petroleum Co Separation of organic compounds by adduct formation
US2717890A (en) * 1951-07-27 1955-09-13 American Cyanamid Co Talloil separation by urea extraction
US2756222A (en) * 1952-06-17 1956-07-24 Swern Daniel Purification of long-chain vinyl esters and ethers
US2838480A (en) * 1952-07-14 1958-06-10 Swern Daniel Separation of mixed fatty acids
US2756252A (en) * 1952-07-28 1956-07-24 Union Oil Co Adducts of substituted phosphoryl amides
US2760974A (en) * 1952-07-28 1956-08-28 Union Oil Co Separation of phosphoryl amide adducts of benzene dicarboxylic acids
US2800466A (en) * 1952-09-30 1957-07-23 Rosenstein Ludwig Process for treating a mixture of saturated and unsaturated fatty acids with expanded urea
US2785151A (en) * 1952-10-14 1957-03-12 Manuel H Gorin Process for treating tall-oil with urea, and particularly a new form of expanded urea
US2798102A (en) * 1952-10-25 1957-07-02 Union Oil Co Method of decomposing werner complex clathrates
US2849511A (en) * 1953-05-25 1958-08-26 Union Oil Co Separation of organic compounds
US2798103A (en) * 1953-07-20 1957-07-02 Union Oil Co Separation of aromatic compounds by clathrate formation with a werner complex
US2782112A (en) * 1954-01-04 1957-02-19 Allied Chem & Dye Corp Herbicide
US2798891A (en) * 1954-02-01 1957-07-09 Union Oil Co Separation of organic compounds by forming clathrates with werner complexes
US2759916A (en) * 1954-02-01 1956-08-21 Socony Mobil Oil Co Inc Urea-nitrile complexes
US2905730A (en) * 1954-09-02 1959-09-22 Phillips Petroleum Co Method of forming a clathrate complex
US2905662A (en) * 1956-05-11 1959-09-22 American Cyanamid Co Preparation of tetracycline-urea compound
US2935457A (en) * 1956-08-16 1960-05-03 British Petroleum Co Production of hard and flexible microcrystalline waxes
US2959580A (en) * 1956-10-17 1960-11-08 Univ Minnesota Formation of inclusion compounds
US3167513A (en) * 1958-03-07 1965-01-26 Lever Brothers Ltd Bleaching compositions
US3082228A (en) * 1959-12-18 1963-03-19 Escambia Chem Corp Method for producing monoesters of polyunsaturated fatty acids
US4601856A (en) * 1984-06-12 1986-07-22 Nippon Oil And Fats Company, Limited Method of purifying oleic acid
EP0178442A1 (fr) * 1984-10-10 1986-04-23 Societe Des Produits Nestle S.A. Procédé d'enrichissement sélectif en acides gras polyinsaturés delta-6 d'un mélange contenant des acides gras delta-6 et delta-9, fractions enrichies obtenues et leur utilisation
AU580330B2 (en) * 1984-10-10 1989-01-12 Societe Des Produits Nestle S.A. Process for the enrichment with ``6 fatty acids of a mixture of fatty acids
EP0619362A3 (fr) * 1993-04-06 1995-11-29 Theodor Wimmer Procédé de fractionnement de mélanges d'acides gras.
US20060281814A1 (en) * 2002-08-06 2006-12-14 Paul Angers Conjugated linolenic acids and methods for commerical preparation and purification
US8598379B2 (en) 2009-11-05 2013-12-03 Purdue Research Foundation Method of lowering the cloud point of fatty acid esters
US9228154B2 (en) 2009-11-05 2016-01-05 Purdue Research Foundation Method of lowering the cloud point of fatty acid esters

Also Published As

Publication number Publication date
GB665248A (en) 1952-01-16
FR994189A (fr) 1951-11-13
NL148190B (nl) 1953-03-16
BE490746A (fr) 1949-09-15
DE883605C (de) 1953-07-20

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