US2461750A - Preparation of phosphatides - Google Patents
Preparation of phosphatides Download PDFInfo
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- US2461750A US2461750A US755255A US75525547A US2461750A US 2461750 A US2461750 A US 2461750A US 755255 A US755255 A US 755255A US 75525547 A US75525547 A US 75525547A US 2461750 A US2461750 A US 2461750A
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- Prior art keywords
- phosphatides
- solvent
- oil
- extract
- crude
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- Expired - Lifetime
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- 238000002360 preparation method Methods 0.000 title description 2
- 239000003921 oil Substances 0.000 description 56
- 235000019198 oils Nutrition 0.000 description 56
- 239000002904 solvent Substances 0.000 description 49
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- 239000000284 extract Substances 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 125000005456 glyceride group Chemical group 0.000 description 21
- 239000000243 solution Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 239000005418 vegetable material Substances 0.000 description 10
- 230000008569 process Effects 0.000 description 9
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 8
- 239000012736 aqueous medium Substances 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 235000012424 soybean oil Nutrition 0.000 description 6
- 239000003549 soybean oil Substances 0.000 description 6
- 244000068988 Glycine max Species 0.000 description 5
- 235000010469 Glycine max Nutrition 0.000 description 5
- -1 coloring matters Substances 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 239000003463 adsorbent Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 244000052616 bacterial pathogen Species 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000944 linseed oil Substances 0.000 description 3
- 235000021388 linseed oil Nutrition 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 240000006240 Linum usitatissimum Species 0.000 description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 235000004426 flaxseed Nutrition 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000009874 alkali refining Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
- C07F9/103—Extraction or purification by physical or chemical treatment of natural phosphatides; Preparation of compositions containing phosphatides of unknown structure
Definitions
- the crude solvent. extracted glyceride oil after being decolorized and freed of solvent in accordance with the principles of our invention, may be degummed at either higher or lower temperatures than indicated in the foregoing examples.
- the gum may be precipitated with aqueous solutions of acids, bases, and salts instead of water alone as employed in the examples.
- aqueous solutions of bases are not recommended'in the practice of this invention, however, because the gum obtained will lie-contaminated with the corresponding salts of anyfree fatty acids present in the crude oil.
- thedegumming solution is a concentrated solution of caustic alkali, such as used in the alkali refining of glyceride oils, partial saponification of the phosphatldes is apt tooccur.
- any of the solvents conventionally used for the extraction of glyceride oils from oleaginous vegetable materials may be used in the practice of our invention.
- the currently preferred solvent in commercial use is hexane, a h gh test gasoline boiling over a range of about 63 to 70 C.
- Other solvents such as trichloroethylene, benzene, and ethanol, all having boiling points under 0., have been used.
- the process of manufacturing phosphatides which comprises extracting oleaginous vegetable material from a raw material with benzene to provide an extract of glyceride oils, phosphatides, and benzene, subjecting said extract to the ac- 6 tion of a decolorizing agent, evaporating benzene from the extract to provide a mutual solution of said glyceride oils and phosphatides, and agitating said solution with an aqueous medium, whereby crude phosphatides are separated from the bulk of the glyceride oils.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Fats And Perfumes (AREA)
Description
. Patented Feb. 15, 1949 7 2,461,750 PREPARATION or PHOSPHATIDES Ralph A. Marmor and Wendell W. Moyer, De-
- catur, Ill.,
Delaware No Drawing.
assignors to A. E. ing Company, Decatur,
Sta-Icy Manufactur- III., a corporation of.
pplication June 17, 1947,
Serial No. 755,255
7 Claims. (Cl. 260-403) This invention relates to improvements in the recovery of phosphatides from oleaginous raw materials. and particularly to such recovery wherein glyceride oil and phosphatidic material are simultaneously extracted from oleaginous material with a liquid solvent, followed by bleaching or decolorizing at low temperature before removing the solvent from the extract, or miscella.
A primary object of the invention is to improve the color andodor of crude phosphatides obtained by extraction of oleaginous vegetable material with a liquid that is a. solvent for the glyceride oils contained in such vegetable material.
Another object of the invention is to reduce or substantially eliminate the necessity for bleaching the recovered phosphatides heretofore required to make them acceptable for many uses,
chiefly in foodstufis.
Additional objects of the invention will become apparent from the description and claims that follow.
The invention accordingly comprises'the several steps and the relation of one or more of such steps with respect to each of the othersv thereof, which will be exemplified in the proc ess hereinafter disclosed, and thescope of the application of which will be indicated in the claims.
It is well known that many oleaginous vegetable materials contain appreciable proportions of I crude phosphatides, sometimes referred to as lecithin. Among such materials are soybeans, cottonseed, com germs, rape seed, peanuts and linseed. Attempts heretofore have been made to obtain the phosphatides from their source materials by extracting the latter with a liquid solvent in which the phosphatides are preferentially soluble. Such attempts have not proven sat isfactory because the solvents used always ex described above, such material has found little.
'sisting chiefly of water, oil, and phosphatides.
Minor constituents frequently present include fatty acids, proteinaceous materials, sterol derivatives and color bodies. When dried, the gum usually contains from 60 to 65 per cent phosphatides. At present, this is one of the principal commercial methods of manufacturing crude phosphatide.
Although large quantities of crude phosphatide are easily and economically manufactured as application as such in many potential uses, especially in foodstuffs, because of its dark color and strong odor. Heretofore, it has been necessary to decolori'ze, and at least partially to deodorize, the crude phosphatidic material before it could be satisfactorily used for many purposes. Although several conventional methods are available for correcting the color and odor deficiencies of the crude phosphatide, all posses one or more drawbacks with respect to processing time, apparatus required, cost of reagents, and the like.
The objectionable color and odor of crude phosphatide obtained as described above are apparently due to the high temperatures conventionally employed to free the extracted oil of solvent. The bulk of the solvent is evaporated from the extract or miscella at atmospheric pressure and the remainder is removed by distillation under reduced pressure, frequently with the aid of superheated steam. During the latter op.- 'eration, the oil is commonly heated to temperatures as high as 100" to 120 C. and held there for substantial periods of time. Prior to this,
the oil is also held for considerable periods of time at and above the boiling point of the solvent. In the case of hexane, the solvent most tracted much oil, coloring matters, and other impurities which had to be separated from the phosphatidic material at considerable expense.
It is also known that the conventional solvent extraction of glyceride oils from oleaginous vegetable materials extracts a large part of the phosphatides present in the raw material with the oil, and that such co-extracted phosphatides can be readily precipitated and separated from the oil by stirring it vigorously with small prof portions of water. extracted phosphatides is large, usually exceeding 20 to 1. The so-called gum or crude phos phatic material thus obtained is a hydrosol con- The ratio of extracted oil to.
widely used at' present, the temperature ranges from about 10 to C.
We have discovered that the color and odor of the crude phosphatide obtained by extracting oleaginous vegetable material with a solvent for glyceride oils and treating the extracted oil with water as described above can be greatly improved by treating the miscella with a color adsorbent prior to evaporating the solvent from the oil.
These beneficial results are apparently due to removal of. color bodies and other impurities from the oil before they become fixed or altered by the heating'that accompanies conventional removal of solvent from the miscella. As pointed out above, the upper temperatures attained by the oil in the conventional solvent removing steps range fromabout 100 to C. It is to be noted also that these upper temperatures are reached by the oil, during removal of the'last portions of solvent, even when such a low boiling solvent as propane is used to extract the oil from its raw material.
Any of the color adsorbents conventionally used for decolorizing glyceride oils are suitable adsorbents may be activated by any of the meth-.
ods well known in the art.
The following examples illustrate our inven- I tion in more detail:
7 Example 1 Flaked soybeans are extracted in a conventional manner with so-called hexane to provide an soybean oil to three parts hexane. Six liters of such miscella were agitated with about 30 grams of an acid activated bleaching, clay for about one hour at 25 to 30 C. The clay was filtered" from the mixture, and the noticeably decolorized miscella was heated over a steam bath at about 100 C. to remove most of the solvent from the oil. The residual crude 01], still containing considerable-solvent, was then heated over the same bath under a reduced pressure of about 20 mm; of mercury to distill out additional solvent. The
lastportion of solvent was separated from the oil by passing superheated steam at about 120 C. into the hot oil under the same vacuum. .The solvent-free oil was then stirred vigorously for several minutes at about 70 C. with about two per cent of water and allowed to stand until the hydrated; gum settled out. four hours. Supernatant oil was decanted from settled gum,- and the latter, together with adhering oil, was transferred to bottles and centrifuged to provide additional separation of gum from adhering oil. The gum thus obtained was much lighter colored and had a much less objectionable odor than gum obtainedin the same way'from conventional crude solvent extracted soybean oil.
Example 2 Dried corn germs were substituted for the flaked soybean in Example 1. The gum thus obtained from the crude solvent extracted corn oil was much lighter colored and of a more pleasant odor than gum obtained by water washing conventional crude solvent extracted corn oil.
Example 3 This required about extract or full miscella comprising about one part miscella was stirred for three hours at 50 C. with 10 grams of powdered benzoyl peroxide, then filtered to remove any unreacted peroxide. The filtered and noticeably decolorized miscella was heated over a steam bath at about 100 C. to evaporate the bulk of the solvent from the oil. The crude oil thus obtained, still containing some solvent, was then heated over the same bath under a reduced pressure of about 20 mm. of mercury to distill out additional solvent. The remaining solvent 'wasseparated from the oil by passing superheated steaminto the hot oil under the same vacuum. The substantially solvent-free oil was then stirred vigorously for several minutes at about 70 C. with about-2 per cent of water and allowed to stand until the hydrated phosphatides settled out. This required about four hours. Supernatant oil was then decanted from the settled phosphatides, and the latter, together with adhering oil, were transferred to bottles and centrifuged to separate additional adhering oil from the phosphatides. The phosphatidic material thus obtained was inuch'lig'hter colored and less odorous than usual.
If desired, the crude solvent. extracted glyceride oil, after being decolorized and freed of solvent in accordance with the principles of our invention, may be degummed at either higher or lower temperatures than indicated in the foregoing examples. Also, the gum may be precipitated with aqueous solutions of acids, bases, and salts instead of water alone as employed in the examples. The
use of aqueous solutions of bases is not recommended'in the practice of this invention, however, because the gum obtained will lie-contaminated with the corresponding salts of anyfree fatty acids present in the crude oil. 'And if thedegumming solution is a concentrated solution of caustic alkali, such as used in the alkali refining of glyceride oils, partial saponification of the phosphatldes is apt tooccur.
Example 4 Flaked soybeans were extracted in a conventional manner with hexane to provide an extract or full miscella comprising about one part soybean oil to three parts hexane. Six liters of this .Phosphatides manufactured in accordance with this invention have a number tential uses. Among these are reducing ,the viscosity oi'chocolate coating materials, preventing the foaming and spatte'ring otheated margarine,
facilitating the wetting of powders and textiles.
Any of the solvents conventionally used for the extraction of glyceride oils from oleaginous vegetable materials may be used in the practice of our invention. The currently preferred solvent in commercial use is hexane, a h gh test gasoline boiling over a range of about 63 to 70 C. Other solvents such as trichloroethylene, benzene, and ethanol, all having boiling points under 0., have been used.
Preferably, the temperature at which the extract is treated with a color adsorbent should not exceed about 60 C. Owing, however, to dilution of the oil and color bodies with the solvent, and to the fact that the color bodies are rapidly adsorbed, the temperature may range upwardly with the same latitude as it does in the extraction operation. I
, It is not essential to successful coagulation of phosphatides from solvent extracted glyceride oils with an aqueous medium that all the solvent be separated from the oil. The maximum proportion of solvent that may remain with the oil and still permit good coagulation of the phosphatides varies with the kind of solvent. In general, however, as much as 15 per cent to 20 per cent of solvent may be tolerated in the oil from which phosphatides are to be prepared in accordance with this invention.
of known and poing out the above process without departing from the scope of the invention, it is intended that all matter contained in-the above description shall be interpreted as illustrative and not in a limiting sense.
It is also to be understood that the following claims are intended to cover all of the generic and specific features of the invention herein described, and all statements of the scope of the invention which, as a matter of language, might be said to fall therebetween.
We claim:
1. The process of manufacturing phosphatides, which comprises extracting oleaginous vegetable material from a raw material with a solvent selected from the group consisting 'of hexane, trichloroethylene, benzene and ethanol to provide an extract of glyceride oils, phosphatides, and
solvent, subjecting said extract to the action of a decolorizing agent, evaporating solvent from the extract to provide a mutual solution of said glyceride oils and phosphatides, and agitating said solution with an aqueous medium, wherebycrude phosphatides are separated from the bulk of the glyceride oils.
2. The process of manufacturing phosphatides,
which comprises extracting oleaginous vegetable material from a raw material with hexane to provide an extract of glyceride oils, phosphatides,
and hexane, subjecting said extract to the actlonof a decolorizing agent, evaporating hexane from the extract to provide a mutual solution of said glyceride oils and phosphatides, and agitating said solution with an aqueous medium,
whereby crude phosphatides are separated from the bulk of the glyceride oils.
3. The process of manufacturing phosphatides, which comprises extractingoleaginous vegetable material from a raw material with trichloroethylene to provide an extract of glyceride oils, phosphatides, and trichloroethylene, subjecting said extract to the action of a decolorizing agent, evaporating trichloroethylene from the extract to provide a mutual solution of said glyceride oils and phosphatides, and agitating said solution with an aqueous medium, whereby crude phosphatides are separated from the bulk of the glyceride oils.
4. The process of manufacturing phosphatides, which comprises extracting oleaginous vegetable material from a raw material with benzene to provide an extract of glyceride oils, phosphatides, and benzene, subjecting said extract to the ac- 6 tion of a decolorizing agent, evaporating benzene from the extract to provide a mutual solution of said glyceride oils and phosphatides, and agitating said solution with an aqueous medium, whereby crude phosphatides are separated from the bulk of the glyceride oils.
5. The process of manufacturing phosphatides, which comprises extracting flaked soybeans with a solvent selected from the group consisting of hexane, trichloroethylene, benzene and ethanol to provide an extract ofv soybean oil, phosphatides, and solvent, subjecting said extract to the action of a decolorizing agent, evaporating solvent from the extract to provide a mutual solution of said soybean oil and phosphatides, and agitating said solution with an aqueous medium, whereby crude phosphatides are separated from the bulk Of the soybean oil.
6. The process of manufacturing phosphatides, which comprises extracting linseed with a solvent selected from the group consisting of hexane, trichloroethylene, benzene and ethanol to provide an extract of linseed oil, phosphatides, and solvent, subjecting said extract to the action of a decolorizing agent, evaporating solvent from the extract to provide a mutual solution of said linseed oil and phosphatides, and agitating said solution with an aqueous medium, whereby crude phosphatides are separated from the bulk of the v linseed oil.
'7. The process of manufacturing phosphatides, which comprises extracting corn germs with a solvent selected from the group consisting of hexane, trichloroethylene, benzene and ethanol.
to provide an extract of corn germ oil, phosphatides, and solvent, subjecting said extract to the action of a decolorizing agent, evaporating solvent from the extract to provide a mutual solution of/said corn germ oil and phosphatides, and agitating said solution with an aqueous medium, whereby crude phosphatides are separated from the bulk of the corngerm oil.
- RALPH A. MARMOR. WENDELL W, MOYER.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US755255A US2461750A (en) | 1947-06-17 | 1947-06-17 | Preparation of phosphatides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US755255A US2461750A (en) | 1947-06-17 | 1947-06-17 | Preparation of phosphatides |
Publications (1)
Publication Number | Publication Date |
---|---|
US2461750A true US2461750A (en) | 1949-02-15 |
Family
ID=25038357
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US755255A Expired - Lifetime US2461750A (en) | 1947-06-17 | 1947-06-17 | Preparation of phosphatides |
Country Status (1)
Country | Link |
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US (1) | US2461750A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2561330A (en) * | 1948-03-25 | 1951-07-24 | Phillips Petroleum Co | Process for refining soybean oil |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1667767A (en) * | 1925-04-14 | 1928-05-01 | Mary Fulford Foster | Process of purifying phosphatides obtained from oilseeds and the like |
US2288441A (en) * | 1939-05-19 | 1942-06-30 | Frederick J Ewing | Process for refining animal and vegetable oils |
US2340104A (en) * | 1944-01-25 | Process fob making mixtures of |
-
1947
- 1947-06-17 US US755255A patent/US2461750A/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2340104A (en) * | 1944-01-25 | Process fob making mixtures of | ||
US1667767A (en) * | 1925-04-14 | 1928-05-01 | Mary Fulford Foster | Process of purifying phosphatides obtained from oilseeds and the like |
US2288441A (en) * | 1939-05-19 | 1942-06-30 | Frederick J Ewing | Process for refining animal and vegetable oils |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2561330A (en) * | 1948-03-25 | 1951-07-24 | Phillips Petroleum Co | Process for refining soybean oil |
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