US2607746A - Composition useful as an antioxidant for fats and oils - Google Patents
Composition useful as an antioxidant for fats and oils Download PDFInfo
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- US2607746A US2607746A US106957A US10695749A US2607746A US 2607746 A US2607746 A US 2607746A US 106957 A US106957 A US 106957A US 10695749 A US10695749 A US 10695749A US 2607746 A US2607746 A US 2607746A
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- 239000000203 mixture Substances 0.000 title description 21
- 239000003963 antioxidant agent Substances 0.000 title description 12
- 239000003925 fat Substances 0.000 title description 11
- 239000003921 oil Substances 0.000 title description 11
- 230000003078 antioxidant effect Effects 0.000 title description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 57
- 239000012141 concentrate Substances 0.000 claims description 36
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 45
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 22
- 239000002253 acid Substances 0.000 description 15
- 235000015165 citric acid Nutrition 0.000 description 15
- 229960004106 citric acid Drugs 0.000 description 15
- -1 citricacid Chemical class 0.000 description 15
- VXHYVVAUHMGCEX-UHFFFAOYSA-N 2-(2-hydroxyphenoxy)phenol Chemical class OC1=CC=CC=C1OC1=CC=CC=C1O VXHYVVAUHMGCEX-UHFFFAOYSA-N 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- 235000006708 antioxidants Nutrition 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 235000010388 propyl gallate Nutrition 0.000 description 11
- QSHVAZMOLNGWSY-UHFFFAOYSA-N 3-butyl-4-methoxyphenol Chemical compound CCCCC1=CC(O)=CC=C1OC QSHVAZMOLNGWSY-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 239000011668 ascorbic acid Substances 0.000 description 5
- 229960005070 ascorbic acid Drugs 0.000 description 5
- 239000011975 tartaric acid Substances 0.000 description 5
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
- 235000010323 ascorbic acid Nutrition 0.000 description 4
- VFPFQHQNJCMNBZ-UHFFFAOYSA-N ethyl gallate Chemical compound CCOC(=O)C1=CC(O)=C(O)C(O)=C1 VFPFQHQNJCMNBZ-UHFFFAOYSA-N 0.000 description 4
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- 235000002906 tartaric acid Nutrition 0.000 description 4
- OUOULDPXBBBBDP-UHFFFAOYSA-N 3-butyl-4-ethoxyphenol Chemical compound C(CCC)C1=C(C=CC(=C1)O)OCC OUOULDPXBBBBDP-UHFFFAOYSA-N 0.000 description 3
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 3
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 3
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 3
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- KCICKSVHJMLGBP-UHFFFAOYSA-N 6-butyl-1-methoxycyclohexa-2,4-dien-1-ol Chemical compound CCCCC1C=CC=CC1(O)OC KCICKSVHJMLGBP-UHFFFAOYSA-N 0.000 description 2
- 239000004262 Ethyl gallate Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XOPOEBVTQYAOSV-UHFFFAOYSA-N butyl 3,4,5-trihydroxybenzoate Chemical compound CCCCOC(=O)C1=CC(O)=C(O)C(O)=C1 XOPOEBVTQYAOSV-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000019277 ethyl gallate Nutrition 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- FBSFWRHWHYMIOG-UHFFFAOYSA-N methyl 3,4,5-trihydroxybenzoate Chemical compound COC(=O)C1=CC(O)=C(O)C(O)=C1 FBSFWRHWHYMIOG-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- RNKMOGIPOMVCHO-SJMVAQJGSA-N 1,3,6-trigalloyl glucose Chemical compound C([C@@H]1[C@H]([C@@H]([C@@H](O)[C@H](OC(=O)C=2C=C(O)C(O)=C(O)C=2)O1)OC(=O)C=1C=C(O)C(O)=C(O)C=1)O)OC(=O)C1=CC(O)=C(O)C(O)=C1 RNKMOGIPOMVCHO-SJMVAQJGSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- UCLHVCFKZSLALE-UHFFFAOYSA-N 2-methylpropyl 3,4,5-trihydroxybenzoate Chemical compound CC(C)COC(=O)C1=CC(O)=C(O)C(O)=C1 UCLHVCFKZSLALE-UHFFFAOYSA-N 0.000 description 1
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical group CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 229960004337 hydroquinone Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- IBKQQKPQRYUGBJ-UHFFFAOYSA-N methyl gallate Natural products CC(=O)C1=CC(O)=C(O)C(O)=C1 IBKQQKPQRYUGBJ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000010466 nut oil Substances 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- TXGSOSAONMOPDL-UHFFFAOYSA-N propan-2-yl 3,4,5-trihydroxybenzoate Chemical compound CC(C)OC(=O)C1=CC(O)=C(O)C(O)=C1 TXGSOSAONMOPDL-UHFFFAOYSA-N 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
- C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
Definitions
- the total weight of the alkylated hydroxyphenyl ether is advantageously from 10 to 50 per cent 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 per cent of the total weight of the concentrate. In no case should the weight 2 H h of propylene glycol be lessthan from 20 to per cent of the total weight oftheconcentrate.
- My concentrate can be employed to stabilizeall fats and oils, e. g. glycerides. of fatty'acids, such, as lard, tallow, peanut oil, palm oil, cocoa nut oil, cottonseed 0il,-soya bean oil, sunflowering s (especially those of, the dry plastic; type) and fatand oil mixtures.
- fatty'acids such as lard, tallow, peanut oil, palm oil, cocoa nut oil, cottonseed 0il,-soya bean oil, sunflowering s (especially those of, the dry plastic; type) and fatand oil mixtures.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Patented Aug. 19, 1952 COMPOSITION USEFUL AS AN AN'rIoXmANr ron FATS AND or s r 2,607,746 E OF C -.9;
James E. Magoifin, Kingsport, rem, 'assignor to Eastman Kodak Company, Rochester, N. Y., a
corporation of New Jersey 7 No Drawing. Application July 2 6, 1349, 2'
Serial No. 106,951 8 Claims. (01. 252-404) This invention relates to a composition useful as an antioxidant for fats and oils. This application is acontinuation-in-part of my application Serial No. 81,842, filed March 16, 1949, now abandoned. p
It has long been known that phenols, such as hydroquinone, guaiacol, eugenol, gallic acid and its esters, e. g. tannin (penta-[m-digalloyllglucose), etc. are useful as antioxidants for fats and oils (Moureu et a1., Compt. rend. 174, 258 (1922)). It is also known that thephenolic compounds such as the alkylated hydroxyphenyl ethers (for example, alkylated hydroxyanisoles, etc.) can be used as antioxidants for fats and oils. It is further known 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 synergistic combinations with acids, such as citricacid, etc. have been found to be adequately effective in retarding 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 sufiicient solubility; Y 1 g Lhave now found that the dispersion of mixtures ofcertain of these antioxidants in fats and oils can be materially improved if a concentrate of these antioxidants in propylene glycol is employed. This concentrate has the advantage of materially increasing the solubility or dispersability of mixtures of certain of the antioxidants in the fatty material to be stabilized,
thus enabling one to secure uniformly dispersed mainder being propylene glycol'plus at least one 4 alk-ylated hydroxyphenyl ether, or propyleneigly-' col plus at least one alkylated hydroxyphenyl ether plus at least one synergizing acid. 7 iv o The total weight of the alkylated hydroxyphenyl ether is advantageously from 10 to 50 per cent 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 per cent of the total weight of the concentrate. In no case should the weight 2 H h of propylene glycol be lessthan from 20 to per cent of the total weight oftheconcentrate.
Advantageously the total weight of the alkylated "hydroxyphenyl ether employed is fromlJO to 5 times-the total weight of the gallicesteri Advantageously the total weight of-the 'syne'r' gizing acid is from 0.2 to 1 times the total weight of the gallic ester. 7 I g The gallic esters which I employ in practicing my invention can be represented by the follow' ing general formula:
UOOR
wherein R represents an alkyl group containing from 1 to 5 carbon atoms, e. g. methyl, ethyl, npropyl, isopropyl, n-butyl, isobutyl, n-amyl, etc. Typical examples are: methyl gallate, ethyl gallate, n-propyl gallate, isopropyl gallate, n-butyl gallate, isobutyl gallate, n-amyl gallate, etc.
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: -hydroxyanisole, 3-tert. butyll-hydroxyani sole, 2 -tert. butyl-l-hydroxyphenetole, 3-tert. butyl 4 hydroxyphenetole, 3-tert. amyl--hydroxyanisdle, ,3 tert. amyl--hydroxyphenetole, etc/no Among the synergizing acids-which I" employ are: citric acid, orthophosphor ic acid, tartaric;- acid, ascorbic acid, etc. V H Efiicacious concentrates are set forth in the. following examples: 7 i
EzcampleI V 1f 1 IPartsby weight nl-Propyl gallate r Citric ]aCid- '.Y..'. V V The above concentrate is-ofs'uch composition that one pound is sufficient to stabilize oneton of lard. I Such a concentrate is a homogeneous system even attemperatures as low as 20 (2.:
It is, therefore, capable of being manufactured and handled in ordinary channels of commerce without separation of the added components. Propylene glycol is satisfactory for incorporation in edible products in concentrations much greater than result from use of this mixture. In contrast to propylene glycol, a'material such as glycerin will not function in a satisfactory manner.
In contrast to fats stabilized against oxidative rancidity with mixtures of the aforesaid antioxidants without the use of propylene glycol as a dispersing medium, fats stabilized with the concentrate set forth in the above example contained the antioxidant dispersed throughout the entire body of; thevfat, thus enabling the fatty material tube-stored for longerperiods of time, and also tp}be;further processed; (as, for example, by cooking; etc.) without serious depletion of the antioxidant, to, giveproducts which are also. stable to the influencesof oxidative rancidity, n
In;- the above; exanflple, the n -p ropyl gallate be replaced with an equal weight f methyl.
eal ia esa ic n) eth l a l te, iscp ny g l a e, n-butyl gallate,n -amylgallate, etc. Likewisethe citric acid can be replaced with an equal Weight of ascorbic acid, orthophosphoric acid or tartaric acid.
The butylated hydroxyanisole of the above example is a mixture of equal parts by weight of:
3rtert. butyl-d-hydroxyanisol'e and : GE's I QTCHHS,
CHs
2-tert. butyl-4-hydroxyanisole Instead of this mixture an equal weight of either 3-tert. butyl-4-hydroxyanisole or 2-tert. butyl-4- hydroxyanisole can be employed, or an equal weight of- Z-tert'. butyl--hydroxyphenetole, 3 tert; butyll-hydroxyphenetole, Z-tert. amyl-4- hydroxyanisole, 3-tert; amyl=4 hydroxyanisola 2- tert. amyl l hydroxyphenetoleor 3-tert. amyl-4- hydroxyphenetole can be employed.
' Ex mple 2 Parts-by weight Propylene glycol 30.
Butylated hydroxyanisol'e 41:.2 n-Propyl gallate 20.6. Citric acid 82 Such a concentrate is a homogeneous system, even at temperatures as low as -20 C. 'As in Example.
1, the n-propyl gallate can be replaced with methyl" gallate (-gallicin), ethyl gallate, isopropyl gallate-,- n-butyl gallateor n-amyl gallate. I The citric acidcan- -be replaced with -ascorbic acid, orthophosphor-ieacid or----tartaric acid. The butylated hydroxyanisole has thesamemeanme; win Example 1 and: can be replaced with. 3 tent: b ty1- ehydroxyaniso1e; or 2-tert. butyllhydroxyanisole or by Z-tert. butyl-4-hydroxyphenetole, 3-tert. buty1-4 hydrqxyphenetole, 2.
seed oil, sesame oil,,hydrogenated' oils or: shorten.-
tert. amy1-4-hydroxyanisole, 3-tert. amyl-4-hydroxyanisole, 2-tert. amyll-hydroxyphenetole or 3-tert. amyl-4-hydroxyphenetole.
Emmple3 Parts by weight Propylene glycol 70 Butylated hydroxyanisole 20 n-Propyl ga1latel 6 Citric acid 4 droxyanisole or by Z-tert. butyll-hydroxyphenetole, B-tert. butyl-4-hydroxyphenetole, 2ftert; amyl 4 hydroxyanisole, 3-- tert. amyl --4 hy-' droxyanisole, 2 -tert. amyl-4-hydroxyphenetole or 3-tert. amyl-i-hydroxyphenetole.'
My concentrate can be employed to stabilizeall fats and oils, e. g. glycerides. of fatty'acids, such, as lard, tallow, peanut oil, palm oil, cocoa nut oil, cottonseed 0il,-soya bean oil, sunflowering s (especially those of, the dry plastic; type) and fatand oil mixtures.
By the term propylene glycol, I-mean the compound which has the following formula:
HOCHCHz-*O'H- The alkylated hydroxyphenyl ethersv can be; prepared by reacting p.-hydroxy anisole or p-hydroxyphenetole with tert. butyl or tert. amyl alcohol, at a temperature of from 80, tov (3., in the presence of phosphoric, acid as, a: catalyst. The alkylated hydroxyphenyl ethers can also. be p epa by reac n .nydr xy ni le: or n-hy- 'dr yp e t le, w th isobutylene or ,with: isoamylene, in the presence: of; sulfuric acid;
The gallic esters whichI employ in practicing;
my inventionv can begprepared as described by: Hepner and. Zyto, Roczniki Chemji: 12; 100, (1932):.
What I, claim as, my invention; and desire;v to. be securedby Letters .Patentof theUnited States.
l. A concentrate. containing propylene. :glycoly.
at least onev gallic cester' selected from the groupconsisting of those. represented: by the-following general formula:
' 50011 wherein Rxrepresents an alkyl group containing from 1 to; .5 1 carbon atoms,. and; at l'east one alky' lated hydroxyphenylether selectedfrom those. representech by the following general formula: r
wherein R1 represents an alkyl groupcontaining from 1 to-2 carbonatomsrand R/zrrepresents a tertiary alkyl group containing from 4 to 5 car bon atoms, the total weight ofigallic ester being from 3 to 30 percent of the'total'weight of the concentrate, and the total weight of the Valkylated hydroxyphenyl ether being from 10 to 50 percentof the total weight of theconcentrate.
2. A concentrate containing propylene glycol, at least one gallic ester selected;from.the group consisting of those represented by the following general formula: Li- 1 .7
HO OH COOR wherein R represents an alkyl group containing from 1 to 5 carbon atoms, at least one alkylated hydroxyphenyl ether selected from the group 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 carbon atoms, and at least one synergizing acid selected from the group consisting of citric acid, orthophosphoric acid, tartaric acid and ascorbic acid, the total Weight'of the gallic ester being from 3 to 30 percent by weight of the total weight of the concentrate, the total weight of the alkylated hydroxyphenyl ether being from to 50 percent of the total weight of the concentrate, and the total weight of the synergizing acid being I from 3 to 10 percent of the total weight of the concentrate, the weight of the propylene glycol being from 20 to 80 percent of the total weight of the concentrate.
3. A concentrate containing propylene glycol, at least one gallic ester selected from the group consisting of those represented by the following general formula:
wherein R represents an alkyl group containing from 1 to 5 carbon atoms, at least one alkylated hydroxyphenyl ether selected from the group 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, tartaric acid and ascorbic acid, the total weightof the gallic ester being from 3 to 30 percent by weight of the total weight of the concentrate, the total weight of the alkylated hydroxyphenyl ether being from- 10 to 50 percent of the total weight of the concentrate, and the total weight of the synergizing acid being from 3 to 10 percent of the total weightoi the concentrate, the .weight of the propylene; glycol being from 20'to80 percent of the tot'alwei'ght of the concentrate, the total weight of the 'alkylated hydroxyphenyl ether being from 1.0 to 5 times the total weight of the gallic ester an the total weight of the synergizing acid being from 0.2 to 1 times the total Weight of the gallic ester. 4. A concentrate containing propylene glycol, n-propyl gallate, a mixture of 2-tert. butyl-4-hydroxyanisole and 3-tert. butyl-e-hydroxyanisole and citric acid, the weight of the n-propyl gallate being from 3 to 30 percent of the total weight of the concentrate, the weight of the mixture of 2-tert. butyl-4-hydroxyanisole and 3- tert. butyl-4-hydroxyanisole being from 10 to 50 percent of the total weight of the concentrate, the weight of the citric acid being from 3 to 10 percent of the total weight of the concentrate, the weight of the propylene glycol being from 20 to percent of the total weight of the concentrate. 5. A concentrate containing propylene glycol, n-propyl gallate, a mixture of 2-tert. butyl-lhydroxyanisole and 3-tert. butyl-4-hydroxyanisole and citric acid, the weight of the n-propyl gallate being from 3 to 30 percent of the total weight of the concentrate, the weight of the mixture of 2-tert. butyl-4-hydroxyanisole and 3-tert. butyl-l-hydroxanisole being from 10 to 50 percent of the total weight of the concentrate, the weight of the citric acid being from 3 to 10 percent of the total weight of the concentrate, the weight of the propylene glycol being from 20 to 80 percent of the total weight of the concentrate, the total weight of the mixture of the 2-tert. butyl-e-hydroxyanisole and 3-tert. butyl-4-hydroxyanisole being from 1.0 to 5 times the weight of the n-propyl gallate and the weight of the citric acid being from 0.2 to 1 times the weight of the n-propyl allate and the weight of the citric acid being from 0.2 to 1 times the weight of the n-propyl gallate.
6. A concentrate having the following composition:
Parts by weight Propylene glycol 60 Mixture of 2-tert. butyl-4-hydroxyanisole and 3-tert. butyl-i-hydroxyanisole 23.5 n-Propyl gallate 11.8 Citric acid 4.7
7. A concentrate having the following composition:
Parts by weight 8. A concentrate having the following composition:
Parts by weight Propylene glycol 70 Mixture of Z-tert. butyl-i-hydroxyanisole and B-tert. buty1-4-hydroxyanisole 20 n-Propyl gallate 6 Citric acide 4 JAMES E. MAGOFFIN. (References on following page) I 7 I 'REEER NCES: 015m)- iihi filming referencesar of 118.com in the. file of this} potent;
' UNITED, STATES PATENTS I Number Name; Date,
OTHER REFERENCES Boehm e1: a1: A Study of'the Inhibiting Acmom of? 'Propyl Gall'ate (Normal Propyl- Trih-ydroxmBenzoate); and Certain Other Trihydric Phenolsu onstheuAutoxidation of. Animal andivegetable Oi1s,v-Qu:=mrt.v Journal of Pharm, vol. 16 (19437), pgs. 232-243. I
Gregory Uses and Applications oi Chemicals andRelated Materia1s,."vo1-. II, p. 27.6., Reinhold Pub...C0., N. Y'. CL, N. Y; (1944').
Riemenschneider; Oxidative Banc'idity' and the.- ;Use of Antioxidants, Trans.. Assoc.
tin No. 2, Apr. 1948, The American. Meat Institute Foundation, pgs. 1-7.
Claims (1)
- 2. A CONCENTRATE CONTAINING PROPYLENE GLYCOL, AT LEAST ONE GALLIC ESTER SELECTED FROM THE GROUP CONSISTING OF THOSE REPRESENTED BY THE FOLLOWING GENERAL FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US106957A US2607746A (en) | 1949-07-26 | 1949-07-26 | Composition useful as an antioxidant for fats and oils |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US106957A US2607746A (en) | 1949-07-26 | 1949-07-26 | Composition useful as an antioxidant for fats and oils |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2607746A true US2607746A (en) | 1952-08-19 |
Family
ID=22314123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US106957A Expired - Lifetime US2607746A (en) | 1949-07-26 | 1949-07-26 | Composition useful as an antioxidant for fats and oils |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2607746A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2772243A (en) * | 1953-08-06 | 1956-11-27 | Eastman Kodak Co | Antioxidant concentrates comprising reaction products of mixed glycerides as solvent carriers |
| US2835635A (en) * | 1956-11-01 | 1958-05-20 | Gen Aniline & Film Corp | Corrosion inhibiting compositions |
| US2839915A (en) * | 1951-05-22 | 1958-06-24 | Bendix Aviat Corp | Method and apparatus for measuring viscosity, etc., of fluid-like materials |
| US3116305A (en) * | 1960-02-18 | 1963-12-31 | Shell Oil Co | Hydroxybenzyl esters |
| US3470099A (en) * | 1967-06-05 | 1969-09-30 | Exxon Research Engineering Co | Esters of polynuclear alcohols and lubricating oils containing same |
| US3947603A (en) * | 1972-04-13 | 1976-03-30 | Firmenich & Cie | Flavoring agent |
| US4829117A (en) * | 1987-06-22 | 1989-05-09 | The Firestone Tire & Rubber Company | Stabilization of guayule-type rubbers |
| US9480268B2 (en) | 2014-09-29 | 2016-11-01 | Mel Blum | Compositions for retarding spoilage of coffee, methods of treating coffee with the compositions and coffee treated with the compositions |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2500543A (en) * | 1945-07-20 | 1950-03-14 | Griffith Laboratories | Antioxidant |
| US2521856A (en) * | 1947-07-26 | 1950-09-12 | A W Brickman | Antioxidant |
| US2564106A (en) * | 1948-10-29 | 1951-08-14 | Du Pont | Food antioxidants |
-
1949
- 1949-07-26 US US106957A patent/US2607746A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2500543A (en) * | 1945-07-20 | 1950-03-14 | Griffith Laboratories | Antioxidant |
| US2521856A (en) * | 1947-07-26 | 1950-09-12 | A W Brickman | Antioxidant |
| US2564106A (en) * | 1948-10-29 | 1951-08-14 | Du Pont | Food antioxidants |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2839915A (en) * | 1951-05-22 | 1958-06-24 | Bendix Aviat Corp | Method and apparatus for measuring viscosity, etc., of fluid-like materials |
| US2772243A (en) * | 1953-08-06 | 1956-11-27 | Eastman Kodak Co | Antioxidant concentrates comprising reaction products of mixed glycerides as solvent carriers |
| US2835635A (en) * | 1956-11-01 | 1958-05-20 | Gen Aniline & Film Corp | Corrosion inhibiting compositions |
| US3116305A (en) * | 1960-02-18 | 1963-12-31 | Shell Oil Co | Hydroxybenzyl esters |
| US3470099A (en) * | 1967-06-05 | 1969-09-30 | Exxon Research Engineering Co | Esters of polynuclear alcohols and lubricating oils containing same |
| US3947603A (en) * | 1972-04-13 | 1976-03-30 | Firmenich & Cie | Flavoring agent |
| US4829117A (en) * | 1987-06-22 | 1989-05-09 | The Firestone Tire & Rubber Company | Stabilization of guayule-type rubbers |
| US9480268B2 (en) | 2014-09-29 | 2016-11-01 | Mel Blum | Compositions for retarding spoilage of coffee, methods of treating coffee with the compositions and coffee treated with the compositions |
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