GB665248A - Improvements in or relating to the fractionation of mixtures of organic compounds of differing degrees of unsaturation - Google Patents
Improvements in or relating to the fractionation of mixtures of organic compounds of differing degrees of unsaturationInfo
- Publication number
- GB665248A GB665248A GB2089049A GB2089049A GB665248A GB 665248 A GB665248 A GB 665248A GB 2089049 A GB2089049 A GB 2089049A GB 2089049 A GB2089049 A GB 2089049A GB 665248 A GB665248 A GB 665248A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acids
- urea
- separated
- fatty acids
- mixtures
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
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
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (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)
Abstract
A mixture of straight-chain polar organic compounds containing components of different degrees of unsaturation is contacted with urea to form crystalline compounds with the more saturated components, which compounds are separated from the unreacted components. Temperature is preferably 0-75 DEG C. and a solvent or diluent may be present, e.g. a ketone or an alcohol of 4-5 carbon atoms or mixtures thereof. Mixtures of fatty acids or their esters or fatty alcohols may be separated. Drying characteristics of vegetable and animal oil acids may be improved by removal of acids of a low degree of unsaturation. Natural fats and oils may be hydrolysed to give the acids or esters with monohydric straight-chain alcohols which are then separated. Saturated fatty acids of 4-50 carbon atoms, and mono-olefinic acids such as oleic, readily form the compounds. Unsaturated acids reacting with some reluctance include linolenic and elaeostearic. Fish oils, tall oil, isomerized oils, and dehydrated castor oil as well as mixtures of amines, amides, nitriles, esters, alcohols, aldehydes or ketone are also referred to. Fractionation of mixtures according to molecular weight as well as unsaturation is possible by variation of temperature, since at temperatures of about 35-75 DEG C. the shorter chain components do not react. By using a temperature gradient a number of desired fractions may be separated. Urea may be used as crystals or in a solvent, for example as a saturated aqueous solution. The concentration of the solution may be adjusted to give a selective effect as may the ratio of urea to the mixture treated, a large excess giving maximum removal. After reaction the mixture is separated. If a settling tank is used, a mixture of the crystalline compounds and dilute urea solution separates from raffinate and is heated to 80-125 DEG C. to decompose said compounds, giving, for example, fatty acids and urea which latter may redissolve to give a solution for recycle. When employing centrifuging or filtration, the crystals are separated and regenerated by heat, steam distillation or treatment with hot solvents. Corrosion of apparatus may be prevented by blanketing with inert gas, by coating or adding inhibitors. In examples, mixtures of linseed, soybean, or dehydrated castor oil fatty acids or their methyl esters are treated with saturated aqueous urea at 22-25 DEG C., methyl isobutyl ketone being used as diluent; alcohols obtained by reduction of linseed oil acids, tall oil, a mixture of stearic and oleic acids, a raffinate from the urea extraction of methyl linseedate, ethyl esters of soybean fatty acids, and methyl esters of tung oil fatty acids are similarly treated. Methyl esters of soybean acids are also treated with solid urea, the product being centrifuged or treated with methyl isobutyl ketone and filtered.ALSO:A mixture of straight-chain polar organic compounds containing components of different degrees of unsaturation is contacted with urea to form crystalline compounds with the more saturated components, which compounds are separated from the unreacted components. Temperature is preferably 0 to 75 DEG C. and a solvent or diluent may be present, e.g. a ketone or an alcohol of 4 to 5 carbon atoms or mixtures thereof. Mixtures of fatty acids or their esters or fatty alcohols may be separated. Drying characteristics of vegetable and animal oil acids may be improved by removal of acids of a low degree of unsaturation. Natural fats and oils may be hydrolyzed to give the acids or esters with monohydric straight chain alcohols which are then separated. Saturated fatty acids of 4 to 50 carbon atoms and mono-olefinic acids such as oleic readily form the compounds. Unsaturated acids reacting with some reluctance include linolenic and elaeostearic. Fish oils, tall oil, isomerized oils and dehydrated castor oil are also referred to. Fractionation of mixtures according to molecular weight as well as unsaturation is possible by variation of temperature since at temperatures of about 35 to 75 DEG C. the shorter chain components do not react. By using a temperature gradient a number of desired fractions may be separated. Urea may be used as crystals or in a solvent, for example as a saturated aqueous solution. The concentration of the solution may be adjusted to give a selective effect as may the ratio of urea to the mixture treated, a large excess giving maximum removal. After reaction the mixture is separated. If a settling tank is used, a mixture of the crystalline compounds and dilute urea solution separates from raffinate and is heated to 80 to 125 DEG C. to decompose said compounds, giving, for example, fatty acids and urea which latter may redissolve to give a solution for recycle. When employing centrifuging or filtration, the crystals are separated and regenerated by heat, steam distillation or treatment with hot solvents. Corrosion of apparatus may be prevented by blanketing with inert gas, by coating or adding inhibitors. In examples, mixtures of linseed, soybean or dehydrated castor oil fatty acids or their methyl esters are treated with saturated aqueous urea at 22 to 25 DEG C., methyl isobutyl ketone being used as diluent; alcohols obtained by reduction of linseed oil acids, tall oil, a mixture of stearic and oleic acids, a raffinate from the urea extraction of methyl linseedate, ethyl esters of soybean fatty acids, and methyl esters of tung oil fatty acids are similarly treated. Methyl esters of soybean acids are also treated with solid urea, the product being centrifuged or treated with methyl isobutyl ketone and filtered.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US4556448 US2596344A (en) | 1948-08-21 | 1948-08-21 | Fractionation process |
Publications (1)
Publication Number | Publication Date |
---|---|
GB665248A true GB665248A (en) | 1952-01-16 |
Family
ID=21938637
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2089049A Expired 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 |
Country Status (6)
Country | Link |
---|---|
US (1) | US2596344A (en) |
BE (1) | BE490746A (en) |
DE (1) | DE883605C (en) |
FR (1) | FR994189A (en) |
GB (1) | GB665248A (en) |
NL (1) | NL148190B (en) |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2681333A (en) * | 1954-06-15 | Gorin | ||
US2681334A (en) * | 1954-06-15 | Formation of urea complexes with | ||
US2759915A (en) * | 1956-08-21 | Gorin | ||
US2732413A (en) * | 1956-01-24 | Process for the recovery of benzene by | ||
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 |
US2759916A (en) * | 1954-02-01 | 1956-08-21 | Socony Mobil Oil Co Inc | Urea-nitrile complexes |
US2798891A (en) * | 1954-02-01 | 1957-07-09 | Union Oil Co | Separation of organic compounds by forming clathrates with werner 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 |
NL110936C (en) * | 1958-03-07 | |||
US3082228A (en) * | 1959-12-18 | 1963-03-19 | Escambia Chem Corp | Method for producing monoesters of polyunsaturated fatty acids |
JPS61297A (en) * | 1984-06-12 | 1986-01-06 | 日本油脂株式会社 | Manufacture of oleic acid |
CH663951A5 (en) * | 1984-10-10 | 1988-01-29 | Nestle Sa | PROCESS FOR THE SELECTIVE ENRICHMENT OF POLYUNSATURATED FATTY ACIDS IN A MIXTURE CONTAINING ENRICHED FRACTION FATTY ACIDS AND COMPOSITIONS CONTAINING THE SAME. |
AT399716B (en) * | 1993-04-06 | 1995-07-25 | Wimmer Theodor | METHOD FOR THE FRACTIONATION OF FATTY ACID ESTER MIXTURES |
CA2396840A1 (en) * | 2002-08-06 | 2004-02-06 | Juan Miguel Garro Galvez | New conjugated linolenic acids and methods for commercial preparation, purification and uses |
EP2496546B1 (en) | 2009-11-05 | 2016-01-27 | Purdue Research Foundation | Method of lowering the cloud point of fatty acid esters |
DE102016008113A1 (en) * | 2016-06-30 | 2018-01-04 | Kd Pharma Bexbach Gmbh | Process for the separation of polyunsaturated hydrocarbons, in particular omega-3 and / or omega-6 fatty acid (s), from a liquid mixture |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2520716A (en) * | 1950-08-29 | Method of separating organic com |
-
1948
- 1948-08-21 US US4556448 patent/US2596344A/en not_active Expired - Lifetime
-
1949
- 1949-08-11 GB GB2089049A patent/GB665248A/en not_active Expired
- 1949-08-17 NL NL148190A patent/NL148190B/en not_active IP Right Cessation
- 1949-08-18 FR FR994189D patent/FR994189A/en not_active Expired
- 1949-08-20 BE BE490746D patent/BE490746A/en unknown
- 1949-08-20 DE DEP52479A patent/DE883605C/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR994189A (en) | 1951-11-13 |
US2596344A (en) | 1952-05-13 |
BE490746A (en) | 1949-09-15 |
NL148190B (en) | 1953-03-16 |
DE883605C (en) | 1953-07-20 |
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