US2390528A - Extraction of phosphatides, free fatty acids, and the like from glyceride oils - Google Patents
Extraction of phosphatides, free fatty acids, and the like from glyceride oils Download PDFInfo
- Publication number
- US2390528A US2390528A US334999A US33499940A US2390528A US 2390528 A US2390528 A US 2390528A US 334999 A US334999 A US 334999A US 33499940 A US33499940 A US 33499940A US 2390528 A US2390528 A US 2390528A
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- US
- United States
- Prior art keywords
- phosphatides
- fatty acids
- extraction
- free fatty
- oil
- 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 - Lifetime
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Classifications
-
- 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
- C11B3/00—Refining fats or fatty oils
- C11B3/006—Refining fats or fatty oils by extraction
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J7/00—Phosphatide compositions for foodstuffs, e.g. lecithin
-
- 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
Definitions
- the present invention relates to removal oi. certain materials, notably such materials as lecithin; like phosphatides, free fatty acids and similar constituents from glyceride oils.
- One object of the invention is to provide a proc- 88s of simultaneously removing gum-forming or "break forming constituents and free fatty acids from a glyceride oil and notably of vegetable oils, which process is relatively simple and inexpensive in its nature.
- oils in addition to comprising mixtures of relatively saturated and unsaturated 'glycerides also include in some cases lecithin-like phosphatides, which are of considerable value for various pharmaceutical and industrial purposes.
- the selective polar solvent may be simply saturated or partially saturated with the aqueous medium or an excess of the aqueous medium may be employed and in part maintained as a separate liquid phase during the extraction.
- the oils and the extraction medium may be contacted by countercurrent now in a suitable column or by simple agitation together, followed by subsequent settling or centrifugation.
- Various polar solvents may be employed in the operation, but the following are considered to be particularly advantageous because they posses a considerable degree of solubility with respect to water:
- the oils also include certain percentages of free fatty acids which are applicable to numerous purposes, for example as constituents in artificial resins or as stock for the manufacture of soaps.
- the phosphatlde material in some cases is ob- Jectionable in the fractionation of the glyceride oils, because upon contact with a solvent such asfurfural it tends to precipitate out to ionn a sludge which collects at 'the inter face between the solvent and the oil body. This sludge may .tend to clog the extraction apparatus and for that reason it is desirable preliminarily to remove it before the oil is subjected to fractionation.
- the phosphatides may be removed from the oil by washing with water or with an aqueous solution or water and alkaline salt, such a sodium carbonate.
- Various ratios of solvent to oil may be employed in the extraction, but a ratio of about 1 to 1 seems to be satisfactory, but this ratio may be substantially increased or decreased if so desired.
- the temperature of extraction preferably is substantially below that of miscibility of the glyceridesin the 011 being extracted. But little difficulty will be encountered in maintaining sumciently low temperature because in the presencee of water solubility of the oils in the solvents is very limited, except at fairly elevated temperatures. Most of the extractions can be eflected quite conveniently ator near normal atmospheric temperatures. Degumming of soya bean oil with 4 aqueous furfural may be effected at 80 or 90 F.
- the aqueous medium may be water alone or an aqueous solution of an alkaline salt, such as sodium carbonate or a 25% solution of sodium phosphate.
- an alkaline salt such as sodium carbonate or a 25% solution of sodium phosphate.
- the extracted oil can be employed for various purposes, but it is particularly suitable for further extraction by the processes disclosed in my foregoing patents for purposes of fractionating it upon the basis of unsaturation.
- the acids as previously indicated can be used for various purposes including themanufacture of soap and the manufacture of modified resins.
- Lecithin is useful for addition to food products, as emulsifying agent and for numerous other pures.
- What I claim is: l.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Fats And Perfumes (AREA)
Description
Patented Dec. 11, 1945 EXTRACTION OF PHOSPHATIDES, FREE FATTY ACIDS, AND THE LIKE FROM GLYCERIDE OILS Stephen E. Freeman, Wauwatosa, Win, assignor to Pittsburgh Plate Glass Company, Allegheny County, Pa... a corporation of Pennsylvania No Drawing. Application May 13, 1940,
' Serial No. 334,999
'ZCiaims.
The present invention relates to removal oi. certain materials, notably such materials as lecithin; like phosphatides, free fatty acids and similar constituents from glyceride oils.
One object of the invention is to provide a proc- 88s of simultaneously removing gum-forming or "break forming constituents and free fatty acids from a glyceride oil and notably of vegetable oils, which process is relatively simple and inexpensive in its nature.
This and other objects of the invention will be apparent from consideration of the following specification and the appended claims.
In my copending Patents 2,200,391 and 2,200,390, having the issue date of May 14, 1940, aredisclosed processes of extracting glyceride oils and notably such oils as comprises a mixture of relatively highly unsaturated and more completely saturated glycerides into fractions, upon the basis of the degree of saturation or unsaturation. Such fractionation may be eifected by numerous polar solvents of which furfural is a typical example. In these extractions the polar solvent and the oil are simply intimately contacted by batch or countercurrent process, or by a suitable countercurrent batch operation.
The oils in addition to comprising mixtures of relatively saturated and unsaturated 'glycerides also include in some cases lecithin-like phosphatides, which are of considerable value for various pharmaceutical and industrial purposes.
benefited by such treatment. The selective polar solvent may be simply saturated or partially saturated with the aqueous medium or an excess of the aqueous medium may be employed and in part maintained as a separate liquid phase during the extraction. The oils and the extraction medium may be contacted by countercurrent now in a suitable column or by simple agitation together, followed by subsequent settling or centrifugation. Various polar solvents may be employed in the operation, but the following are considered to be particularly advantageous because they posses a considerable degree of solubility with respect to water:
Table A Hydrooyl Eater Meth l formate 1 51i al c gf Ethy ene glycol dliormate.
Trlacetin Glycol diacetate Methyl malonnte Math 1 oxalate Ethy oxalate n-Propyl alcohol Iso-propyl alcohol Ethylene gl col Propylene g ycol Glycerine Tertiary butyl alcohol Dlmethyl ethynyl carblnol Hydrooyl-O flier Allyl alcohol Ethylene chlorhydrin Glycerol monochlorhydrin a o Beta-hydroxy roplonltrile The oils also include certain percentages of free fatty acids which are applicable to numerous purposes, for example as constituents in artificial resins or as stock for the manufacture of soaps.
The phosphatlde material in some cases is ob- Jectionable in the fractionation of the glyceride oils, because upon contact with a solvent such asfurfural it tends to precipitate out to ionn a sludge which collects at 'the inter face between the solvent and the oil body. This sludge may .tend to clog the extraction apparatus and for that reason it is desirable preliminarily to remove it before the oil is subjected to fractionation. The phosphatides may be removed from the oil by washing with water or with an aqueous solution or water and alkaline salt, such a sodium carbonate. However, such process is not eflfective to remove the free fatty acids also contained in the oi v According to provisions of the present invention it is proposed simultaneously to remove free fatty acids and sludge-forming constituents such as lecithin and the like from glyceride oils by subiecting the latter to intimate contact with a solu- Beta-ethoxy et yl lactate Beta-ether ethyl glycolate Furi'urnl a coho 2-nitro-1-butanol Diethyl ammo ethanol Propylene chlorhydrin HydrooyF-Estor Meth l glycolate Ethy glycolate Beta-h roxy ethyl acetate Ethyl uctate Mono acetin Diacetin Hydrant-Carbonyl Methyl butanolone Acetyl meth l carbinol Diacetone a cohol Methyl acetyl lactate Hydraoyl ether Ether Dioxane Dloxolane DimethylCellololvo Dimethoxy tetragiycol Acid Formic acid Acetic acid Propionic acid Isobutyric acid Ester-Other Methyl Celloaolve formats Methyl Celloaoivo acetate Methyl Cellosoive adipate Dimetthyl Cellosolve succina e Eth l n-methyl earbamato Met yl chloroacetate Methyl cyanoacetate Ester-Carbonyl Methyl levuilnate Eth levulinato Met l acetoacetate Ethy acetoacetate Isopropyl ncetoacetata Aldehyde Acetaldehyde AldchydhOthor Methoxy acetaldehyde Furfural m-Nitrobenzaldehyde Ketm Acetonyl acetone Acetone Amine Diethylene tetramine Triethylene tetrunino Pipyridene Pyridene Nitrite Proplonitrilo Eaten of inorganic acids Trimethyl phosphate Triethyltgholphate Beta-me oxy ethyl carbon- Dimethyl sulfate Amide:
Propionamlde Butyramide Him Nitromeihano Nitroethauo 7 Various ratios of solvent to oil may be employed in the extraction, but a ratio of about 1 to 1 seems to be satisfactory, but this ratio may be substantially increased or decreased if so desired. The temperature of extraction preferably is substantially below that of miscibility of the glyceridesin the 011 being extracted. But little difficulty will be encountered in maintaining sumciently low temperature because in the presencee of water solubility of the oils in the solvents is very limited, except at fairly elevated temperatures. Most of the extractions can be eflected quite conveniently ator near normal atmospheric temperatures. Degumming of soya bean oil with 4 aqueous furfural may be effected at 80 or 90 F.
The aqueous medium may be water alone or an aqueous solution of an alkaline salt, such as sodium carbonate or a 25% solution of sodium phosphate. Contact of the oil with aqueous sol-v vent results in precipitation of the lecithin sludge in the oil from which it can be removed by centotal volume of the latter. where large volumes of water are employed withfurfural, only a limited amount will dissolve, the remainder will be maintained as a third phase in the system.
The extracted oil can be employed for various purposes, but it is particularly suitable for further extraction by the processes disclosed in my foregoing patents for purposes of fractionating it upon the basis of unsaturation.
The acids as previously indicated can be used for various purposes including themanufacture of soap and the manufacture of modified resins. Lecithin is useful for addition to food products, as emulsifying agent and for numerous other pures. What I claim is: l. The process of obtaining a fraction rich in phosphatides and a fraction rich in free fatty acids from glyceride oils, which process comprises intimately contacting the oil with furfural approximately saturated with water to obtain a piurality of liquid phases, one consisting of furfural and water containing the free fatty acids and the other consisting primarily of oil with the phosphatides precipitated as a suspension therein,
then separating off the phases and separating the phosphatides from the oil.
2. A process as defined in claim 1, in which the glyceride oil undergoing treatment is soya bean so Oil.
STEPHEN E. FREEMAN.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US334999A US2390528A (en) | 1940-05-13 | 1940-05-13 | Extraction of phosphatides, free fatty acids, and the like from glyceride oils |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US334999A US2390528A (en) | 1940-05-13 | 1940-05-13 | Extraction of phosphatides, free fatty acids, and the like from glyceride oils |
Publications (1)
Publication Number | Publication Date |
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US2390528A true US2390528A (en) | 1945-12-11 |
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Application Number | Title | Priority Date | Filing Date |
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US334999A Expired - Lifetime US2390528A (en) | 1940-05-13 | 1940-05-13 | Extraction of phosphatides, free fatty acids, and the like from glyceride oils |
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US (1) | US2390528A (en) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2448434A (en) * | 1946-10-05 | 1948-08-31 | Gen Mills Inc | Process for producing nonbreak oil |
US2599016A (en) * | 1947-06-16 | 1952-06-03 | Short Milling Co J | Refining soybean lecithin |
US2605272A (en) * | 1948-12-08 | 1952-07-29 | Sherwin Williams Co | Method for removing fines from vegetable oils and miscella containing said oils |
US2753362A (en) * | 1951-05-18 | 1956-07-03 | Standard Brands Inc | Process of extracting lipids from plant and animal tissue |
US2754309A (en) * | 1953-03-04 | 1956-07-10 | Staley Mfg Co A E | Vegetable oil refining |
US2997492A (en) * | 1959-02-17 | 1961-08-22 | Procter & Gamble | Method for preparing fatty esters of straight chain hexitols |
EP0074251A1 (en) * | 1981-09-04 | 1983-03-16 | Yeda Research And Development Company, Ltd. | Novel lipid fraction, its preparation and pharmaceutical compositions containing same |
US4714571A (en) * | 1984-02-13 | 1987-12-22 | The Liposome Company, Inc. | Process for purification of phospholipids |
US5429823A (en) * | 1986-11-28 | 1995-07-04 | The Liposome Company, Inc. | Phospholipid composition and liposomes made therefrom |
WO1998012288A1 (en) * | 1996-09-19 | 1998-03-26 | Siegfried Peter | Process for purifying fats and oils of animal or vegetable origin |
US9745541B1 (en) * | 2016-09-09 | 2017-08-29 | Inventure Renewables, Inc. | Methods for making free fatty acids from soaps using thermal hydrolysis followed by acidification |
-
1940
- 1940-05-13 US US334999A patent/US2390528A/en not_active Expired - Lifetime
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2448434A (en) * | 1946-10-05 | 1948-08-31 | Gen Mills Inc | Process for producing nonbreak oil |
US2599016A (en) * | 1947-06-16 | 1952-06-03 | Short Milling Co J | Refining soybean lecithin |
US2605272A (en) * | 1948-12-08 | 1952-07-29 | Sherwin Williams Co | Method for removing fines from vegetable oils and miscella containing said oils |
US2753362A (en) * | 1951-05-18 | 1956-07-03 | Standard Brands Inc | Process of extracting lipids from plant and animal tissue |
US2754309A (en) * | 1953-03-04 | 1956-07-10 | Staley Mfg Co A E | Vegetable oil refining |
US2997492A (en) * | 1959-02-17 | 1961-08-22 | Procter & Gamble | Method for preparing fatty esters of straight chain hexitols |
EP0074251A1 (en) * | 1981-09-04 | 1983-03-16 | Yeda Research And Development Company, Ltd. | Novel lipid fraction, its preparation and pharmaceutical compositions containing same |
US4714571A (en) * | 1984-02-13 | 1987-12-22 | The Liposome Company, Inc. | Process for purification of phospholipids |
US5429823A (en) * | 1986-11-28 | 1995-07-04 | The Liposome Company, Inc. | Phospholipid composition and liposomes made therefrom |
US5783210A (en) * | 1986-11-28 | 1998-07-21 | The Liposome Company, Inc. | Phospholipid composition |
WO1998012288A1 (en) * | 1996-09-19 | 1998-03-26 | Siegfried Peter | Process for purifying fats and oils of animal or vegetable origin |
US9745541B1 (en) * | 2016-09-09 | 2017-08-29 | Inventure Renewables, Inc. | Methods for making free fatty acids from soaps using thermal hydrolysis followed by acidification |
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