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Publication numberUS2610915 A
Publication typeGrant
Publication dateSep 16, 1952
Filing dateJul 24, 1950
Priority dateJul 24, 1950
Publication numberUS 2610915 A, US 2610915A, US-A-2610915, US2610915 A, US2610915A
InventorsMattil Karl F
Original AssigneeSwift & Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Winterized glyceride oil and process of producing the same
US 2610915 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

fiatenteci Sept. 16, 1952 WINTERIZED GLYCERIDE 011. AND PROCESS OF PRODUCING THE SAME Karl F. Mattil, Chicago, 111., assignor to Swift &

Company, Chicago, 111., a corporation of Illinois No Drawing. Application July 24, 1950, Serial No. 175,659

11 Claims.

This invention relates to treating fatty glyceride material, and it has to do more particularly with the manufacture of an improved glyceride o1 In the processing of glyceride fatty material an important problem is the removal of the high melting point glycerides which are normally solid at room temperatures and Which tend to separate from the oil at relatively high temperatures. The conditioning of a glyceride fatty material to effectuate separation of the liquid fats from the undesirable solid fats must be carefully controlled in order to obtain the solid fat in a crystalline form suitable for filtration. Under the best conditions, filtration is inefficient, for the solid fats often separate as extremely small particles and remain suspended in the oil as colloidal dispersions, thus making the straining operation very difficult.

I have now discovered that certain compositions hereinafter to be described and referred to as crystal inhibiting and modifying agents are extremely useful in prolonging the cold test of glyceride oils and in facilitating the Winterizing process.

In winterizing" a glyceride oil or processing a fatty material such as sperm oil or white grease to obtain lard oil, the conditioning of the oil or fatty material to effectuate separation of the liquid fats from the solid fats must be carefully controlled in order to obtain the solid fat in a crystalline form suitable for filtration. Under the best present-day conditions filtration is ineflicient, for the solid fats often separate as extremely small particles and remain suspended in the oil as colloidal dispersions, thus making the straining operation very diflicult. The difficulties attending the process of Winterizing as hitherto practiced may be overcome by incorporating into the glyceride oil or glyceride fatty material, such as sperm oil or white grease, a small amount of the crystal inhibitors and modifiers, hereinafter described. I have found that the addition of such substance profoundly affects crystallization whereby the crystals of the solid fats are rendered firmer and better defined. The form f the crystals is so improved that a more facile and complete separation of the undesirable solids from the liquid constituents of the oil is effected. In addition to improving winterization, these substances are usually present in sufiicient amounts to lengthen substantially the cold test of the oil, although this effect is not so pronounced as that which results when the crystal inhibitor is added after the oil has been winterized.

An important object of the present invention is,

therefore, to provide an improved method for separating the solidified fat crystals from the liquid fats in glyceride fatty material.

Another object of the present invention is to provide a method of improving the Winterizing of glyceride oils.

Still another object of the invention is to provide a glyceride oil having an improved cold test.

A still further object of the present invention is to provide an improved glyceride oil which will remain clear and homogeneous for long periods of time at relatively low temperatures. v

Another object of the invention is to provide an improved glyceride oil which will exhibit good stability at relatively low temperatures when incorporated in an emulsion.

Additional objects of the invention will be apparent from the description and claims to follow.

Broadly, the invention contemplates the addition to a glyceride oil or glyceride fatty material, either before or after winterization, of a small amount of an oil-soluble polymerization product of esters having vinyl or substituted vinyl group, according to the following general formula; namely, esters of the formula wherein X is a hydrogen atom and alkyl or aromatic hydrocarbon group, and Y is o Jae-R in which R is a monovalent hydrocarbon radical containing more than 4 carbon atoms or an ether derivative of said hydrocarbon radical.

' Compounds of the above type are the esters of acrylic acid or of its alpha-alkyl or alpha-aryl substitution products and monohydric alcohols containing more than 4 carbon atoms, such as octyl, decyl, lauryl, or cetyl esters of acrylic acid, alpha-methacrylic acid, and other alpha-substituted homogenous or acrylic acid, as more fully described in U. S. Patent 2,091,627.

The most effective polymers for the present purpose are the oil-soluble polymerized esters of acrylic acid or alpha-methacrylic acid and monohydric, saturated, primary aliphatic alcohols containing from 12 to 18 carbon atoms or molecules, such as lauryl, cetyl, or octadecyl esters.

These esters need not be pure but may be mixtures of one or more of the higher aliphatic alcohols and the acrylic or methacrylic acid polymerization products. A mixture of two or more of the foregoing polymers may also be used.

These polymers are preferably prepared by heating the monomeric esters or mixtures thereof at 70-100 C. in the presence of small amounts of polymerization-inducing catalysts, such as peroxides or ozonides, as more fully disclosed in U. S. Patents 2,100,993 and 2,114,233.

Preferably the amount of the foregoing crystal modifiers used ranges from .005 to 1.0 per cent. Where it is desired to add the crystal modifier prior to the Winterizing operation to facilitate filtration, it is often advantageous to add additional amounts to replace that which may be removed with the solid matter during filtration. Larger amounts of the crystallization inhibitor may be used but generally is not commercially advisable.

The following examples illustrate how the invention may be practiced, and are not intended to limit the scope of the invention:

Example I To 100 grains of winterized cottonseed salad oil having a cold test of about 9 hours was added 1.0 per cent of the oil-soluble polymerization product of an ester of alpha-methacrylic acid and lauryl alcohol. After the said polymerization product is uniformly distributed throughout the oil, a cold test of the treated oil gave a value of 45 hours.

Example [I To 100 grams of winterized cottonseed salad oil having a cold test of about 9 hours was added 0.10 per cent of the oil-soluble polymerization product of an ester of alpha-methacrylic acid and lauryl alcohol. The cold test of the treated salad oil gave a value of 35 hours.

Example III To a sample of winterized cottonseed oil having a cold test of 15 hours, 0.02 per cent of cetylalpha-methacrylate soluble in oil was added and uniformly distributed therethrough. The oil containing the above crystal-inhibiting agent exhibited a cold test of 60 hours.

Example I V Mayonnaise made with a winterized cottonseed salad oil containing 0.02 per cent n-oetyl-acrylate soluble in oil was placed in a cooler maintained at a temperature of 28 F., and the mayonnaise emulsion did not break until after being held seven days at the said temperature. A similar sample of mayonnaise stood up for two days when placed in a cooler maintained at a temperature of 24 F. The control sample of mayonnaise consisting of a winterized cottonseed oil having the same initial cold test but which was not treated with a crystal-inhibiting agent broke in less than one day at 24 F. and less than three days at 28 F.

Example V A sample of refined and bleached cottonseed oil containing 0.20 per cent lauryl-alpha-methacrylate soluble in oil was placed in a cooler maintained at 45 F. for three days. Upon filtering the sample by gravity through a standard filter cloth, the yield of oil from the sample containing the above crystal-inhibiting agent was 82 per cent. The yield of the control sample of the refined and bleached cottonseed oil was '71 per cent.

Example VI To a sample of white grease was added 0.10 per cent of an ester of alpha-methacrylic acid and octadecyl alcohol soluble in oil and the sample seeded for five days at F. The yield of oil upon pressing the white grease treated in the foregoing manner was per cent. The yield from the control chamber of the white grease containing no crystal-inhibiting agent was 55 per cent.

Example VII A sample of crude sperm oil containing 0.05 per cent n-lauryl acrylate soluble in oil was seeded in 45 F. for six days and then pressed. The yield of winterized sperm oil treated in the foregoing manner was 82 per cent. The yield of the control sample of the sperm oil was per cent.

As hereinbefore mentioned, the above-described crystal inhibitors and modifiers may be added to the glyceride materials before or after winterization. The addition of the crystal modifier before winterization serves primarily to facilitate and improve the Winterizing operation. Although crystal formation is retarded in the presence of the additive, once the crystals are formed they are of such form as to settle quickly, and because of the nature of the crystals a sharp separation of the undesired solids from the liquid constituents of the oil is possible. An advantage of the improved filtering operation is that the yields of oils are greatly increased over the Winterizing process as hitherto practiced. Often it is desirable to add an additional small amount of the additive after the winterization operation so as to replace that which was filtered out along with the high melting glyceride crystals.

In case it is desired to have a glyceride oil of very long cold test, the materials described above are added to the oil after it has been winterized, the extent of lengthening the cold test depending on the quality of oil chosen, the additive being more efiective'in an oil having an original 'longer cold test than in an oil of shorter cold test.

Another important advantage of the invention flows from the use of oil treated with the described agents in emulsions. An emulsion, such as mayonnaise, containing a vegetable oil treated in the foregoing manner will remain stable for muchlonger periods of time than has been hitherto possible to maintain such emulsions.

While the invention described herein has particular application to the manufacture of salad oils, the invention is not limited to such an operation. It should be understood that the invention is useful in treating various fatty glyceride materials wherein a solid or crystalline fraction is separated from a liquid fraction as in the separation of a crystalline fraction from animal oils such as lard oil, oleo oil, sperm oil, and animal fats and greases used in the preparation of lard oil and the like. In treating various vegetable and animal oils it is often desirable to separate a solid fraction such as stearin, palmitin, spermaceti and other high melting point fractions by crystallizing such fraction with or without the presence of a solvent and then separating the crystallized fraction by cold settling, pressing, centrifuging of filtration. The crystal modifying agents herein described may also be used to modify the crystal structure of the solid phase whereby it may be more readily separated from the liquid phase when extracted with a suitable solvent.

Obviously many modifications and variations of the invention hereinbefore set forth may be made without departing from the spirit and scope thereof, and therefore only such limitations should be imposed as are indicated in the appended claims.

I c aim:

l. A glyceride oil composition of improved cold .test, comprising a glyceride oil having incorporated therein a small amount of an oil-soluble product to improve the cold test thereof, said product being the polymerization product of esters containing a radical selected from the group consisting of vinyl and substituted vinyl compounds according to the general formula wherein X is selected from the group consisting of hydrogen and alkyl and aromatic hydrocarbon radicals and Y is selected from the group having the formula and -(||JOR wherein R is selected from the group consisting of a monovalent hydrocarbon radical containing more than 4 carbon atoms and oxy derivatives thereof.

2. A glyceride oil composition of improved cold test comprising a glyceride oil having incorporated therein a small amount of an oil-soluble product to improve the cold test thereof, said product being a polymerization product of a substituted vinyl compound according to the general formula wherein X is an alkyl radical and R is an allphatic monohydric saturated alcohol radical having more than 12 carbon atoms.

3. A glyceride oil composition of improved cold test comprising a glyceride oil containing relatively high melting point constituents having in-v corporated therein a small amount of an oilsoluble product to improve the cold test thereof, said product being the polymerization product of an ester of acrylic acid and a monohydric saturated alcohol containing more than 12 carbon atoms per molecule.

4. A glyceride oil composition of improved cold test comprising a glyceride oil containing relatively high melting point constituents having incorporated therein a small amount of an oilsoluble product to improve the cold test thereof, said product being the polymerization product of an alpha-alkyl substituted acrylic acid and a monohydric saturated alcohol containing more than 12 carbon atoms per molecule.

5. A glyceride oil composition of improved cold test comprising a glyceride oil containing relatively high melting point constituents having incorporated therein a small amount of an oil-soluble polymerization product in an amount between .005 and 1.0 per cent by weight to improve the cold test thereof, said product being a member of a group consisting of lauryl, cetyl, and octadecyl esters of alpha-methacrylic acid.

6. In a method of separating a glyceride fatty material into higher and lower melting point constituents by fractionating the liquefied fatty material, the improvement which comprises dispersing throughout the said fatty material a small amountof an oil soluble crystal modifying product to increase the rate at which the relatively high melting point crystals settle, said product being the polymerization product of esters containing a radical selected from the group consisting of vinyl and substituted vinyl radicals according to the general formula wherein X is selected from the group consisting of hydrogen and alkyl and aromatic hydrocarbon radicals and Y is selected from the group having the formula t oo-R and wherein R. is selected from the group consisting of a monovalent hydrocarbon radical containing more than 4 carbon atoms and oxy derivatives thereof.

7. An improved method of separating a glyceride fatty material into higher and lower melting point constituents, which comprises dispersing throughout a liquefied glyceride fatty material a small amount of an oil-soluble polymerization product of esters containing a radical selected from the group consisting of vinyl and substituted vinyl radicals according to the general formula wherein X is selected from the group consisting of hydrogen and alkyl and aromatic hydrocarbon radicals and Y is selected from the group having the formula and wherein R is selected from the group consisting of a monovalent hydrocarbon radical containing more than 4 carbon atoms and oxy derivatives thereof, cooling the said fatty material containing the added polymerization product to crystalide fatty material into higher and lower melting point constituents, which comprises dispersing throughout a liquefied glyceride fatty material a small amount of an oil-soluble polymerization 7 product of a substituted vinyl compound. having the general formula X CH2=-% JO-R wherein X is an alkyl radical and R is an aliphatic monohydric saturated alcohol radical having more than 12 carbon atoms, cooling the said fatty material containing the added polymerization product to crystallize the higher melting point constituents, and separating the said constituents from the lower melting point constituents remaining in the liquid glyceride fatty material, the crystals of said higher melting point constituents formed on cooling being similar and better dofined to facilitate separation from the said lower melting point constituents.

9. An improved method of separating a glyceride fatty material into'higher and lower melting point constituents, which comprises dispersing throughout a liquefied glyceride fatty material a "small amount of an oil-soluble polymerization product of an ester of acrylic acid and monohydric saturated alcohol containing more than 12 carbon atoms per molecule, cooling the said fatty material containing the added polymerization product to crystallize the higher melting point constituents, and separating the said constituents from the lower melting point constituents remaining in the liquid glyceride fatty material, the crystals of said higher melting point constituents formed on cooling being similar and better defined to facilitate separation from the said lower melting point constituents.

10. An improved method of separating a glyceride fatty material into higher and lower melting point constituents, which comprises dispersing throughout a liquefied glyceride fatty material a small amount of an oil-soluble polymerization product of an alpha-alkyl aryl substituted acrylic acid and monohydric saturated alcohol containing more than 12 carbon atoms per molecule, cooling the said fatty material containing the added polymerization product to crystallize the higher melting point constituents, and separating the said constituents from the lower melting point constituents remaining in the liquid glyceride fatty material, the crystals of said higher melting point constituents formed on cooling being similar and better defined to facilitate separation from the said lower melting point constituents.

11. An improved method of separating a glyceride fatty material into higher and lower melting point constituents, which comprises dispersing throughout a liquefied glyceride fatty material a small amount of an oil-soluble polymerization product selected from the group consisting of polymerized lauryl esters of alpha-methacrylic acid, cetyl esters of alpha-methacrylic acid, and octadecyl esters of alpha-methacrylic acid, cooling the said fatty material containing the added polymerization product tocrystallize the higher melting point constituents, and separating the said constituents from the lower melting point constituents remaining in the liquid glyceride fatty material, the crystals of said higher melting point constituents formed on cooling being similar and better defined to facilitate separation from the said lower melting point constituents.

' "KARL F. MATTIL.

REFERENCES CITED The following references are of record in the file of this patent:

UNITED STATES PATENTS Number Name Date 2,079,336 Ralston et a1 May 4, 1937 2,266,591 Eckey Dec. 16, 1941 2,418,668 Royce Apr. 8, 1947 2,518,917 Mattil l Aug. 15, 1950

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2079336 *Mar 1, 1935May 4, 1937Armour & CoShortening compound and processes of preparing the same
US2266591 *Oct 14, 1938Dec 16, 1941Procter & GambleProcess of improving salad oils
US2418668 *Mar 30, 1943Apr 8, 1947Southern Cotton Oil CompanyImprovement in winter vegetable oils
US2518917 *Oct 22, 1945Aug 15, 1950Swift & CoTreatment of glyceride oils
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US2903363 *Sep 17, 1954Sep 8, 1959Farr Gerald WSolvent fractionation of winterized cottonseed oil bottoms
US3145223 *Sep 22, 1961Aug 18, 1964Pennsalt Chemicals CorpWinterizing glyceride oils
US3173936 *May 9, 1962Mar 16, 1965Pennsalt Chemicals CorpWinterizing glyceride oils
US3290340 *Jun 17, 1963Dec 6, 1966Procter & Gamble1-palmitoyl-2, 3-di
US5602265 *Jul 19, 1994Feb 11, 1997Van Den Bergh Foods Co., Division Of Conopco, Inc.Fractionation of triglyceride oils
US5621125 *Jul 29, 1994Apr 15, 1997Van Den Bergh Foods Co., Division Of Conopco, Inc.Heating oil in solvent, adding crystallization modifying membrane lipid, cooling, separating
US5872270 *Dec 21, 1995Feb 16, 1999Van Den Bergh Foods Company, Division Of Conopco, Inc.Modified inulin or phlein crystallisation modifying substance
US6162934 *Feb 4, 1998Dec 19, 2000Lipton, Division Of Conopco, Inc.Dry fractionation using a fat soluble derivative of a polymer, preferably an ester of a polysaccharide as a crystal habit modifier for improved separation efficiency between solid stearin phase and liquid olein phase
EP0543356A2 *Nov 19, 1992May 26, 1993Röhm GmbhProcess for making compositions with improved low temperature behaviour
EP0805196A1 *Jul 15, 1994Nov 5, 1997Unilever PlcFractionation of triglyceride oils
WO1994022320A1 *Mar 31, 1994Oct 13, 1994Opta Food Ingredients IncFat soluble polymers and their use in foods
WO1995004122A1 *Jul 15, 1994Feb 9, 1995Unilever NvFractionation of triglyceride oils
Classifications
U.S. Classification554/2, 554/211, 554/212
International ClassificationC11B7/00, A23D9/013, A23D9/007
Cooperative ClassificationC11B7/0083, A23D9/013
European ClassificationC11B7/00D, A23D9/013