US2607745A - Composition useful as an antioxidant for fats and oils - Google Patents

Composition useful as an antioxidant for fats and oils Download PDF

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US2607745A
US2607745A US91635A US9163549A US2607745A US 2607745 A US2607745 A US 2607745A US 91635 A US91635 A US 91635A US 9163549 A US9163549 A US 9163549A US 2607745 A US2607745 A US 2607745A
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concentrate
tert
hydroxyanisole
total weight
acid
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James E Magoffin
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Eastman Kodak Co
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Eastman Kodak Co
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    • 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
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
    • 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
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0092—Mixtures

Definitions

  • This invention relates to compositions useful as antioxidants for fats and oils.
  • one or more ,alkylated hydroxyph'en'yl Fethers can be dispersed in propylene glycol to give a concentrate which ishighly useful as an antioxidant for fats and oils.
  • the totalweight of the alkylated hydroxyphenyl ether the concentrate is'from 10 to 60%of the total'wei'ght of the concentrate.
  • the remainder cari'be propylene glycol alone, or propylene glycol plusanjadditional antioxidant; e. g. 'a p-dihydric phenol, e.
  • the total weight of the alkylated hydroxyphenyl ether in the concentrate is from l5 to 50% of the total weight of the concentrate.
  • the weight of the p-dihydric phenol is advantageously from 5 to 20% of the total weight of the concentrate.
  • the total weight of the synergizing acid is advantageously from 3 to 10% of the total weight of the concentrate.
  • the weight of propylene glycol be less than from 40 to 70% of the total weight of the concentrate.
  • the total weight of the alkylated hydroxyphenyl' ether employed is from .1375 to 2.25 times the total weight of the p-dihydric phenol.
  • the total weight of the synergizing acid is from 0.3 to 0.7 times the total weight of the p-dihydric phenol.
  • alkylated hydroxyphenyl ethers which I employ in practicing my invention can be represented by the following general formula:
  • R1 represents an alkyl group containing from 1 to 2 carbon atoms
  • R2 represents a tertiary alkyl group containing from 4 to 5 carbon atoms.
  • Typical examples are: 2-tert. butyl- 4-hydroxyanisole, 3-tert. butyl-l-hydroxyanisole, 2-tert. butyl-4-hydroxypheneto1e, 3-tert.- butyl- 4-hydroxyphenetole, B-tert. amyl-4-hydroxyanisole, 3-tert. amyl-i-hydroxyphenetole, etc.
  • synergizing acids which I employ are citric acid, orthophosphoric acid, metaphosphoric acid, tartaricacid, ascorbic acid, etc.
  • An efiicacious concentrate which can be prepared according to my invention is represented by the following example:
  • Such a concentrate is of such composition that one pound is sufiicient to stabilize one ton of lard.
  • Such a concentrate is a homogeneous system even at temperatures as low as 20 C. It is, therefore, capable of being manufactured and handled in ordinary channels of commerce without separation of' the added components.
  • Propylene glycol issatisfactory for incorporation in edible products in concentrations much greater than result from use of this mixture.
  • a material such as glycerin will not function in.
  • fats stabilized according to the method set forth in the above example contained the antioxidant uniformly dispersed throughout the entire body of the fat, thus enabling the fatty material to be stored for longer periods of time, and also to be further processed (as, for example, bycooking,
  • invention also contemplates a concentrate of butylated hydroxyanisole in propylene glycol,
  • citricacid can be replaced by 6 parts by weight of ascorbic acid, tartaric acid, metaphosphoric acid or orthophosphoric acid.
  • compositions which can be used are, for example, the following:
  • fats or fatty materials such as the glycerides of fatty acids, peanut oil,. palm oil, cocoanut oil, cottonseed oil, soya bean oil, sunflowerseedoiLsesame oil, shortenings (especially those of the dryplastic type), ,fat-oil mixtures,
  • the alkylated hydroxyphenyl others can be prepared by reacting p-hydroxyanisole or p-hydroxyphenetolewith tert. butyl or tert. amyl a1- the presence of orthophosphoric acid as a catcohol, at. a temperature of from to C., in
  • the alkylated hydroxyphenyl ethers can also be prepared by reacting p-hydroxyanisole or p-hydroxyphenetole with isobutylene or with isoamylenein'the presence of sulfuric acid.
  • a concentrate containing. propylene. glycol and at least one 'alkylated hydroxyphenyl ether selected from the group consisting of those represented by the following. general formula:
  • R1 represents an alkyl group containing from 1 to 2 carbon atomsand R2 represents a tertiary-alkyl group containing from 4 to 5 carbon atoms,- the total weight of the alkylated total weight of the concentrate.
  • the weight of the propylene glycol being from 40 to 70% of the total weight of the concentrate.
  • R1 represents an alkyl group containing from 1 to 2 carbon atoms and R2 represents a tertiary alkyl group containing from 4 to 5 carbon atoms
  • at least one synergizing acid selected from the group consisting of citric acid, orthophosphoric acid, metaphosphoric acid, tartaric acid and ascorbic acid
  • the total weight of the alkylated hydroxyphenyl ether being from to 60% by weight of the total weight of the concentrate
  • the total weight of the hydroquinone being from to 30% of the total weight of the concentrate
  • the total weight of the synergizing acid being from 3 to 10% of the total weight of the concentrate
  • the weight of the propylene glycol being from 40 to 70% of the total weight of the concentrate.
  • a concentrate having the following composition:

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
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Description

Patented Aug. 19 1952 UNITED STATES PATENTOFFICE v COMPOSITION USEFUL AS AN ANTIOXIDANT FOR FATS AND OILS James E. Magoffin, Kingsport, Tenn., assignor to Eastman Kodak Company, Rochester, corporation of New Jersey No Drawing. Application May 5, 1949, V
- Serial No. 91,635
This invention relates to compositions useful as antioxidants for fats and oils. This applicaknown that the antioxidant action of such phenolic antioxidants can be synergized with acids, e. g. citric acid, orthophosphoric acid, tartaric acid, etc. While these phenolic compounds, as well as their synergisticcombinations with acids, such as.citricracid;etcyhave been found to be highly effective in retarding the oxidative rancidity during storage of fats and oils, they are subject to the disability in many instances of being only slightly soluble in the fatty materials to which they are added. In processing such fats and oils a considerable percentage of the effective amounts of the antioxidants are frequently lost due to this lack of sufficient solubility. V
I have now found that the dispersion of these antioxidants in fats and oils .can be materially rial to be stabilized, thus enabling one to secure uniformly dispersed mixtures of the antioxidant in the fatty materials and more effectively to prevent oxidation with a given proportion of antioxidant to fat.
According to my invention, one or more ,alkylated hydroxyph'en'yl Fethers, can be dispersed in propylene glycol to givea concentrate which ishighly useful as an antioxidant for fats and oils. Advantageously, the totalweight of the alkylated hydroxyphenyl ether the concentrate is'from 10 to 60%of the total'wei'ght of the concentrate. The remainder cari'be propylene glycol alone, or propylene glycol plusanjadditional antioxidant; e. g. 'a p-dihydric phenol, e. gm-hydroquinonefl' toluliydroquinone, 'ethylhydroqu none, 'n-propylliydroguinone; rgbutylhydroqui none, tertL: butylhydroquinone, etc. ;-or propylene 8 Claims. (01. 252 404i glycol plus at least one synergizing acid, or propylene glycol plus the additional antioxidant plus at least one synergizing acid. Most advantageously, the total weight of the alkylated hydroxyphenyl ether in the concentrate is from l5 to 50% of the total weight of the concentrate.
When employed, the weight of the p-dihydric phenol is advantageously from 5 to 20% of the total weight of the concentrate. Where at least one synergizing acid is employed, the total weight of the synergizing acid is advantageously from 3 to 10% of the total weight of the concentrate. In no case, should the weight of propylene glycol be less than from 40 to 70% of the total weight of the concentrate.
Advantageously, the total weight of the alkylated hydroxyphenyl' ether employed is from .1375 to 2.25 times the total weight of the p-dihydric phenol. Advantageously, the total weight of the synergizing acid is from 0.3 to 0.7 times the total weight of the p-dihydric phenol.
The alkylated hydroxyphenyl ethers which I employ in practicing my invention can be represented by the following general formula:
' wherein R1 represents an alkyl group containing from 1 to 2 carbon atoms, and R2 represents a tertiary alkyl group containing from 4 to 5 carbon atoms. Typical examples are: 2-tert. butyl- 4-hydroxyanisole, 3-tert. butyl-l-hydroxyanisole, 2-tert. butyl-4-hydroxypheneto1e, 3-tert.- butyl- 4-hydroxyphenetole, B-tert. amyl-4-hydroxyanisole, 3-tert. amyl-i-hydroxyphenetole, etc.
Among the synergizing acids which I employ are citric acid, orthophosphoric acid, metaphosphoric acid, tartaricacid, ascorbic acid, etc.
An efiicacious concentrate which can be prepared according to my invention is represented by the following example:
Such a concentrate is of such composition that one pound is sufiicient to stabilize one ton of lard. Such a concentrate is a homogeneous system even at temperatures as low as 20 C. It is, therefore, capable of being manufactured and handled in ordinary channels of commerce without separation of' the added components. Propylene glycol issatisfactory for incorporation in edible products in concentrations much greater than result from use of this mixture. In contrast thereto, a material such as glycerin will not function in.
a satisfactory manner because of the difiiculty of getting the above type compounds to disperse therein and like disadvantages.
In contrast to the fats stabilized against oxidative rancidity with hydroquinone without the use of propylene glycol as a dispersing medium, fats stabilized according to the method set forth in the above example contained the antioxidant uniformly dispersed throughout the entire body of the fat, thus enabling the fatty material to be stored for longer periods of time, and also to be further processed (as, for example, bycooking,
' etc.) without removal of the antioxidant, to give products which are also stable to the influences ofoxidative' rancidity.
Althoughthe above exampleillustrates a composition containing hydroquinone, an alkylated hydroxyphenyl ether and a synergizingacid, my
invention also contemplates a concentrate of butylated hydroxyanisole in propylene glycol,
-'butylated hydroxyphenetole in propylene glycol, jZ-tertiary amyl--hydroxyanisole in propylene glycol, 3-tertiary amyl-4-hydroxyanisole in'proplyene glycol,
Z-tertiary amyl-4-hydroxyphenetole in propylene glycol, 3-tertiary amyl-4- hydroxyphenetole in propylene glycol, or mixtures of oneor more (e. g. 1 to 3) of these alkylated hydroxyphenyl ethers with a p-dihydric phenol, or with at least one (e. g. 1 to 2) synergizq ing acid, such as citric acid, ortho-phosphoric acid, metaphosphoric acid, ascorbic acid, tartaric acid, etc., or with -p-dihydric phenol plus at least 'one of said synergizing acids. 7
Moreover, in the above example, the citricacid can be replaced by 6 parts by weight of ascorbic acid, tartaric acid, metaphosphoric acid or orthophosphoric acid. Still other compositions which can be used are, for example, the following:
Other fats or fatty materials, such as the glycerides of fatty acids, peanut oil,. palm oil, cocoanut oil, cottonseed oil, soya bean oil, sunflowerseedoiLsesame oil, shortenings (especially those of the dryplastic type), ,fat-oil mixtures,
;etc. can be stabilized by ,dispersing therein,one of my concentrates in propylene glycol. The butylated hydroxyanisole of theaboveex '4 amples is a mixture of about equal parts by weight of:
OCH: 0 OH:
CCHa CH:
3-tert. butyl-4-hydroxyanisole Z-tert. butyl-4-hydroxyanisolc Instead of a mixture of S-tert. butyli-hydroxyanisole and 2-tert. butyl-4-hydroxyanisole, like parts by weight of either of the compounds can be used in the above examples. The butylated hydroxyanisoles can be replaced with either 2- tert. butyl-4-hydroxyphenetole or 3-tert. butyl Y -4-hydfoxyphenetole or a mixture thereof, or by Z-tert. amyl-4-hydroxyanisole or 3-tert. amyl-4- hydroxyanisole or 2-tert. amyl-l-hydroxyphenetole or 3-tert. amyl-l-hydroxyphenetole or a mixture of such tertiary amyl compounds.
By the termfpropylene glycol, I mean the compound which has the following formula:
The alkylated hydroxyphenyl others can be prepared by reacting p-hydroxyanisole or p-hydroxyphenetolewith tert. butyl or tert. amyl a1- the presence of orthophosphoric acid as a catcohol, at. a temperature of from to C., in
alyst. The alkylated hydroxyphenyl ethers can also be prepared by reacting p-hydroxyanisole or p-hydroxyphenetole with isobutylene or with isoamylenein'the presence of sulfuric acid.
What I claim asmy invention and desire to be secured by Letters Patent of the United States is:
l. A concentrate, containing. propylene. glycol and at least one 'alkylated hydroxyphenyl ether selected from the group consisting of those represented by the following. general formula:
I OH.
wherein R1 represents an alkyl group containing from 1 to 2 carbon atomsand R2 representsa tertiary-alkyl group containing from 4 to 5 carbon atoms,- the total weight of the alkylated total weight of the concentrate.
2. A concentrate containing propylene glycol, a p -dihydric phenol and at least one alkylated hydroxyphenyl ether selected from the group consisting of those represented 'by'the following general formula:
' hydroxyphenyl ether being fromlO to 60% of the wherem'glirepresentsIan m l oup containing fl' s r natomsaan R2 represents'a r -m a k oup "con a ing from 4-,. to, 5 carbon-M91118, the t awei nt ofthe alkylated y nylh r .being from 10, to 166%, ;of
M Weight of he..z n ntrate,' "and: the wei tthe n-q h iah nol -be.mg,rrom
, '5 i 31 1 t t tala gis tbr e concentrate,
.5 the weight of the propylene glycol being from 40 to 70% of the total weight of the concentrate.
3. A concentrate containing propylene glycol, hydroquinone, at least one alkylated hydroxyphenyl ether selected from the group consisting of those represented by the following general formula:
wherein R1 represents an alkyl group containing from 1 to 2 carbon atoms and R2 represents a tertiary alkyl group containing from 4 to 5 carbon atoms, and at least one synergizing acid selected from the group consisting of citric acid, orthophosphoric acid, metaphosphoric acid, tartaric acid and ascorbic acid, the total weight of the alkylated hydroxyphenyl ether being from to 60% by weight of the total weight of the concentrate, the total weight of the hydroquinone being from to 30% of the total weight of the concentrate, the total weight of the synergizing acid being from 3 to 10% of the total weight of the concentrate, and the weight of the propylene glycol being from 40 to 70% of the total weight of the concentrate.
4. A concentrate containing propylene glycol, a mixture of Z-tert. butyl-4-hydroxyanisole and 3 tert. butyl-4-hydroxyanisole, hydroquinone and citric acid, the weight of the mixture of 2- tert. butyl-4-hydroxyanisole and 3-tert. butyl-4- hydroxyanisole being from 10 to 60% of the total weight of the concentrate, the weight of hydroquinone being from 15 to 30% of the total weight of the concentrate, the weight of the citric acid being from 3 to 10% of the total weight of the concentrate, and the weight of the propylene glycol being from 40 to 70% of the total weight of the concentrate.
5. A concentrate containing propylene glycol, a mixture of 2-tert. butyl-4-hydroxyanisole and 3 tert. butyl-4-hydroxyanisole, hydroquinone and citric acid, the weight of the mixture of 2- tert. butyl-4-hydroxyanisole and 3-tert. butyl-4- hydroxyanisole being from 10 to 60% of the total weight of the concentrate, the weight of the hydroquinone being from 15 to 30% of the total weight oi! the concentrate, the weight of the and 3-tert. butyl-4-hydroxyanisole 30 Hydroquinone 15 Citric acid 6 7. A concentrate having the following composition:
Parts by weight Propylene glycol Mixture of 2-tert. butyl-4-hydroxyanisole and 3-tert. butyl-4-hydroxyanisole 100 8. A concentrate having the following composition:
Parts by weight Propylene glycol 100 Mixture of 2-tert. butyl-4-hydroxyanisole and 3-tert. butyl-4-hydroxyanisole Hydroquinone JAMES E. MAGOFFIN.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,104,084 Latham Jan. 4, 1938 2,115,040 Nitardy Apr. 26, 1938 2,310,710 Rosenwald Feb. 9, 1943 2,333,657 Mattill et a1. Nov. 9, 1943 2,500,543 Hall Mar. 14, 1950 2,521,856 Kraybill et a1 Sept. 12, 1950 OTHER REFERENCES Boehm et al., in Quart Journal of Pharm., vol. 16 (1943), pp. 232-43.
Gregory, Uses and Applications of Chemicals and Related Materials," vol. II, p. 2'75, Reinhold Pub. Corp. N. Y. 0., N. Y., 1944.

Claims (1)

1. A CONCENTRATE CONTAINING PROPYLENE GLYCOL AND AT LEAST ONE ALKYLATED HYDROXYPHENYL ETHER SELECTED FROM THE GROUP CONSISTING OF THOSE REPRESENTED BY THE FOLLOWING GENERAL FORMULA:
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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2704746A (en) * 1950-08-16 1955-03-22 Universal Oil Prod Co Butylated hydroxyanisole flakes
US2768084A (en) * 1952-06-25 1956-10-23 Griffith Laboratories Oil soluble synergistic antioxidant
US2772243A (en) * 1953-08-06 1956-11-27 Eastman Kodak Co Antioxidant concentrates comprising reaction products of mixed glycerides as solvent carriers
US2833634A (en) * 1953-01-26 1958-05-06 Ethyl Corp Synergistic antioxidants and their use
US2875899A (en) * 1952-09-25 1959-03-03 Gen Motors Corp Oil filter coating
US2910367A (en) * 1957-07-09 1959-10-27 Corn Products Co Food composition
US2945001A (en) * 1956-08-27 1960-07-12 Goodyear Tire & Rubber Synergistic antioxidants
US2976156A (en) * 1957-03-21 1961-03-21 Lever Brothers Ltd Treatment of edible oils
US3038810A (en) * 1959-08-18 1962-06-12 Corn Products Co Food composition containing an auxiliary additive and a fungistat
US3116305A (en) * 1960-02-18 1963-12-31 Shell Oil Co Hydroxybenzyl esters
US3855150A (en) * 1970-06-15 1974-12-17 Eastman Kodak Co Stabilization of hydroquinone solutions with citric acid
US4765927A (en) * 1985-08-12 1988-08-23 House Food Industrial Company Limited Antioxidizing composition
US4829117A (en) * 1987-06-22 1989-05-09 The Firestone Tire & Rubber Company Stabilization of guayule-type rubbers

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2104084A (en) * 1935-11-06 1938-01-04 Du Pont Stabilization of animal and vegetable fats and oils
US2115040A (en) * 1934-08-15 1938-04-26 Squibb & Sons Inc Protection of vitaminous oils
US2310710A (en) * 1939-09-18 1943-02-09 Universal Oil Prod Co Inhibitor for gasoline
US2333657A (en) * 1942-05-26 1943-11-09 Lever Brothers Ltd Antioxidant for fats and oils
US2500543A (en) * 1945-07-20 1950-03-14 Griffith Laboratories Antioxidant
US2521856A (en) * 1947-07-26 1950-09-12 A W Brickman Antioxidant

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2115040A (en) * 1934-08-15 1938-04-26 Squibb & Sons Inc Protection of vitaminous oils
US2104084A (en) * 1935-11-06 1938-01-04 Du Pont Stabilization of animal and vegetable fats and oils
US2310710A (en) * 1939-09-18 1943-02-09 Universal Oil Prod Co Inhibitor for gasoline
US2333657A (en) * 1942-05-26 1943-11-09 Lever Brothers Ltd Antioxidant for fats and oils
US2500543A (en) * 1945-07-20 1950-03-14 Griffith Laboratories Antioxidant
US2521856A (en) * 1947-07-26 1950-09-12 A W Brickman Antioxidant

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2704746A (en) * 1950-08-16 1955-03-22 Universal Oil Prod Co Butylated hydroxyanisole flakes
US2768084A (en) * 1952-06-25 1956-10-23 Griffith Laboratories Oil soluble synergistic antioxidant
US2875899A (en) * 1952-09-25 1959-03-03 Gen Motors Corp Oil filter coating
US2833634A (en) * 1953-01-26 1958-05-06 Ethyl Corp Synergistic antioxidants and their use
US2772243A (en) * 1953-08-06 1956-11-27 Eastman Kodak Co Antioxidant concentrates comprising reaction products of mixed glycerides as solvent carriers
US2945001A (en) * 1956-08-27 1960-07-12 Goodyear Tire & Rubber Synergistic antioxidants
US2976156A (en) * 1957-03-21 1961-03-21 Lever Brothers Ltd Treatment of edible oils
US2910367A (en) * 1957-07-09 1959-10-27 Corn Products Co Food composition
US3038810A (en) * 1959-08-18 1962-06-12 Corn Products Co Food composition containing an auxiliary additive and a fungistat
US3116305A (en) * 1960-02-18 1963-12-31 Shell Oil Co Hydroxybenzyl esters
US3855150A (en) * 1970-06-15 1974-12-17 Eastman Kodak Co Stabilization of hydroquinone solutions with citric acid
US4765927A (en) * 1985-08-12 1988-08-23 House Food Industrial Company Limited Antioxidizing composition
US4829117A (en) * 1987-06-22 1989-05-09 The Firestone Tire & Rubber Company Stabilization of guayule-type rubbers

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