US2684971A - Bleaching and stabilization of fatty acid esters, including glycerides, especially monoglycerides - Google Patents
Bleaching and stabilization of fatty acid esters, including glycerides, especially monoglycerides Download PDFInfo
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- US2684971A US2684971A US241394A US24139451A US2684971A US 2684971 A US2684971 A US 2684971A US 241394 A US241394 A US 241394A US 24139451 A US24139451 A US 24139451A US 2684971 A US2684971 A US 2684971A
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- esters
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- bleaching
- fatty acid
- bleached
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Links
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 21
- 229930195729 fatty acid Natural products 0.000 title claims description 21
- 239000000194 fatty acid Substances 0.000 title claims description 21
- 238000004061 bleaching Methods 0.000 title claims description 20
- -1 fatty acid esters Chemical class 0.000 title claims description 18
- 125000005456 glyceride group Chemical group 0.000 title description 10
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 title description 9
- 230000006641 stabilisation Effects 0.000 title description 2
- 238000011105 stabilization Methods 0.000 title description 2
- 150000002148 esters Chemical class 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 26
- 239000003638 chemical reducing agent Substances 0.000 claims description 13
- 239000007800 oxidant agent Substances 0.000 claims description 12
- 238000002845 discoloration Methods 0.000 claims description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 34
- 239000000047 product Substances 0.000 description 12
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical class OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 10
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 9
- 239000007844 bleaching agent Substances 0.000 description 9
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 9
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000000087 stabilizing effect Effects 0.000 description 4
- NHYCGSASNAIGLD-UHFFFAOYSA-N Chlorine monoxide Chemical class Cl[O] NHYCGSASNAIGLD-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 125000002153 sulfur containing inorganic group Chemical group 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- OSVXSBDYLRYLIG-UHFFFAOYSA-N dioxidochlorine(.) Chemical compound O=Cl=O OSVXSBDYLRYLIG-UHFFFAOYSA-N 0.000 description 2
- 150000002194 fatty esters Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 2
- 229940099427 potassium bisulfite Drugs 0.000 description 2
- HEZHYQDYRPUXNJ-UHFFFAOYSA-L potassium dithionite Chemical compound [K+].[K+].[O-]S(=O)S([O-])=O HEZHYQDYRPUXNJ-UHFFFAOYSA-L 0.000 description 2
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 2
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 2
- 235000019252 potassium sulphite Nutrition 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 235000010269 sulphur dioxide Nutrition 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- 239000004155 Chlorine dioxide Substances 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910001485 alkali metal perchlorate Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000019398 chlorine dioxide Nutrition 0.000 description 1
- 229910001902 chlorine oxide Inorganic materials 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 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
- C11B3/00—Refining fats or fatty oils
- C11B3/02—Refining fats or fatty oils by chemical reaction
- C11B3/08—Refining fats or fatty oils by chemical reaction with oxidising agents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/02—Refining fats or fatty oils by chemical reaction
Definitions
- This invention relates to a process of bleaching glycerides and more particularly to a bleaching process that produces glycerides with improved color properties that are retained over relatively long periods of time.
- the process is especially adapted for the treatment of monoglycerides.
- fatty glycerides be light in color so that products made therefrom, such as soaps, shortenings, partial glyceride esters, etc. will in turn have as little color as possible.
- the present invention relates to such a bleaching process. More particularly it relates to a process of bleaching glycerides and other higher fatty acid esters by heating them with a suitable bleaching agent of the oxidizing type and then stabilizing the resultant bleached glycerides with a suitable reducing agent.
- the invention particularly relates to such a monoglycerides.
- Lard monoglycerides that had been carbonbleached to a color of 10 red in a Lovibond 5%" cell, and which could not by this treatment be further bleached were intimately contacted at -80 C. with 2% by weight of a solution of hydrogen peroxide of the standard commercial 30% H202 concentration for 20' minutes to give a product of 2.0 red color.
- coco monoglycerides having an original Lovibond color of 3.5 red were intimatelycontacted with 0.25% by weight of a 30% H202 solution to give a bleached monoglyceride product having a color of 1.5 red.
- color of this bleached product was good, color reversion began after a relatively short time so that the efiect of the bleaching operation eventually was rendered nugatory.
- a stabilized bleached monoglyceride ester product was obtained that retained its low 3 color from 5 to 8 times as long as in the absence of the bisulfite treatment.
- bleached esters were similarly prepared.
- the amount of hydrogen peroxide required varied with the. color of the ester after the preliminary carbon or other bleach, as well as with the color required in the final product.
- the fatty esters that may be treated by the process of the present invention include the natural fatty acid esters, such as fats or fatty oils suitable for employment in the soap-making or edible-fats industries, or any other fatty acid esters, whether of a polyhydric alcohol, such as glycerol or the glycols, or of a monohydric-alcohol, or mixtures of such esters.
- a polyhydric alcohol such as glycerol or the glycols
- monohydric-alcohol or mixtures of such esters.
- esters of fatty acids of about 8 to 26, and preferably about 12 to 20, carbon atoms per molecule of fatty acid.
- Such fatty esters include coconut oil, palm oil, olive oil, cottonseed oil, corn oil, soya bean oil, tung oil, wool fat, tallow, whale and fish oils, etc., as well as the alkyl esters of the fatty acids corresponding to these oils, such as the methyl and ethyl esters.
- the invention is especially desirable in connection with the production of color-stabilized monoglyceride esters of high molecular weight fatty acids of the type indicated above.
- esters are relatively unstable and begin to revert to their original color only a relatively short while after the hydrogen peroxide treatment depending upon such factors as temperature, degree of aeration, etc., but when they are further treated with a suitable reducing agent such as sodium bisulfite to deactivate or remove the color-forming tendency of the bleached esters, they then remain stable as regards color for periods of time far in excess of normal in the absence of the stabilizing treatment described herein.
- a suitable reducing agent such as sodium bisulfite to deactivate or remove the color-forming tendency of the bleached esters
- the degree of improvement ranges from a factor of at least five to as high as ten to fifteen, in terms of the increase in time before redevelopment of color occurs.
- oxidizing agents such as alkali metal chorates and perchlorates, chlorine oxides such as the monoxide and dioxide, acetyl peroxide, benzoyl peroxide, etc.
- alkali metal bisulfite or other reducing agent may be conveniently added to the washing solution to bring about the desired stabilizing action according to the present invention.
- Both the step of treating the esters with the oxidizing agent and the step of treating them with the reducing agent may be carried out under a wide variety of conditions. Somewhat elevated temperatures are preferably, but not necessarily, employed.
- the esters While undergoing treatment are preferably subjected to efficient agitation in order to bring about effective contact between the respective phases.
- a process for bleaching fatty acid esters that comprises contacting said esters with an oxidizing agent to bleach said esters and treating the bleached esters before any substantial discoloration thereof with a sulfur-containing inorganic reducing agent to remove'any "excess oxidizing agent and to deactivate any color-forming bodies.
- a process for bleaching fatty acid esters that comprises contacting said esters with an oxidizing agent'selected from the group consist-- ing of hydrogen peroxide, alkali metal chlorates, alkali metal perchlorates, chlorine monoxide, chlorine dioxide, acetyl peroxide, and benzoyl peroxide to bleach said esters and treating the bleached esters before any substantial discoloration thereof with a sulfur-containing inorganic reducing agent selected from the group consisting of sodium bisulfite, potassium bisulfite, so dium sulfite, potassium sulfite, sulfur dioxide, so-' dium hydrosulfite, and potassium hydrosulfite'to remove any excess oxidizing agent and to decompose any color-forming bodies.
- an oxidizing agent's selected from the group consist-- ing of hydrogen peroxide, alkali metal chlorates, alkali metal perchlorates, chlorine monoxide, chlorine dioxide, acetyl peroxide, and benzoyl peroxid
- a process for bleaching fatty acid esters that comprises contacting said esters with hydrogen peroxide to bleach said esters and treating the bleached esters before any substantial discoloration thereof with sodium bisulfite to remove any excess hydrogen peroxide and to decompose any color-forming bodies.
- a process for bleaching higher fatty acid monoglyceride esters that comprises contacting said esters with hydrogen peroxide to bleach said esters and treating the bleached esters before any substantial discoloration thereof with sufficient sodium bisulfite to insure at least a molecular equivalent thereof withrespect to'the hydrogen peroxide initiallyintroduced to remove any excess hydrogen peroxide and to deactivate any color-forming bodies, :thereby minimizing any tendency to color reversion.
- a process for bleaching higher fatty acid monoglyceride esters that comprises contactingsaid esters with hydrogen peroxide to ibleach said esters and treating the bleachedesters before any substantial discoloration thereof with an aqueous solution of sodium bisulfite to remove any excess hydrogen peroxide: and to decompose any color-forming bodies, thereby minimizing any tendency to color reversion.
- esters with hydrogen peroxide to bleach said References Cited in the file of this patent esters and treating the bleached esters before any TENT substantial discoloration thereof with sodium bi- UNITED STATES PA 8 sulfite to remove any excess hydrogen peroxide Number Name Date and to decompose any color-forming bodies, 5 1,890,121 Lagasse 6, 1932 thereby minimizing any tendency to color re- 2,259,968 Andersen 1941 version 2,524,056 Jespersen Oct. 3, 1950 11.
- a process as in claim 10 in which the higher fatty acid glyceride is lard monoglyceride.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Detergent Compositions (AREA)
Description
Patented July 27, 1954 BLEACHING AND STABILIZATION OF FATTY ACID ESTERS, IN
CLUDING GLYCERIDES,
ESPECIALLY MON OGLYCERIDES William Godfrey Alsop, to Colgate-Palmolive N. J., a corporation of Summit, N. J., assignor Company, Jersey City, Delaware No Drawing. Application August 10, 1951, Serial No. 241,394
12 Claims.
This invention relates to a process of bleaching glycerides and more particularly to a bleaching process that produces glycerides with improved color properties that are retained over relatively long periods of time. The process is especially adapted for the treatment of monoglycerides.
It is desirable, and in some instances essential, that fatty glycerides be light in color so that products made therefrom, such as soaps, shortenings, partial glyceride esters, etc. will in turn have as little color as possible.
Producers of soaps, edible fat products, etc. must, in the absence of other provisions, use relatively high grade stocks to provide light colored products, or if they use low grade stocks which are usually very dark in color, they must employ a bleaching process to remove the discoloration.
The latter alternative is usually that which is employed. The demand for glycerides is generally so high and the competition for high grade stocks so keen that the producer frequently must resort to the more plentiful and less expensive low grade stocks and depend rather on the efiiciency of his bleaching operation to produce a light colored product. I
The present invention relates to such a bleaching process. More particularly it relates to a process of bleaching glycerides and other higher fatty acid esters by heating them with a suitable bleaching agent of the oxidizing type and then stabilizing the resultant bleached glycerides with a suitable reducing agent. The invention particularly relates to such a monoglycerides.
It has already been proposed to bleach triglyceride esters with oxidizing agents and it has also been proposed to remove color from vegetable oils by using reducing agents.
The difficulties with the bleaching processes of the prior art have been that the glycerides are only temporarily bleached thereby. After they have been permitted to stand for a period of time they revert to substantially their original state of discoloration, especially when in the liquid phase. It is, accordingly, an object of this invention to provide a decolorization process for glyceridesand particularly for monoglycerides, that results in very stable glyceride esters which even after prolonged periods of storage reveal little, if any, tion.
Surprisingly, it has been discovered that it is possible to produce a color-stabilized glyceride ester product, and especially a color-stabilized monoglyceride ester product by first bleaching reversion to their original discoloraprocess as applied to.
' 2 with a suitable bleaching agent of the oxidizing type followed by treating the bleached esters with a suitable reducing agent.
In order to indicate still more fully the nature of the present invention, the following examples of typical procedure are set forth with the understanding that this is by way of illustration only, and not by way of limiting the scope of the invention.
Lard monoglycerides that had been carbonbleached to a color of 10 red in a Lovibond 5%" cell, and which could not by this treatment be further bleached were intimately contacted at -80 C. with 2% by weight of a solution of hydrogen peroxide of the standard commercial 30% H202 concentration for 20' minutes to give a product of 2.0 red color. The lard monoglycerides, after this treatment with hydrogen peroxide followed by heating to drive ofi the excess peroxide, exhibited no stability even with the known, normally excellent oxidation inhibitors, such as propyl gallate, in the well-known Swift stability test.
However, these same hydrogen peroxidebleached lard monoglyceride esters, when subsequently treated with sodium bisulfite in the form of a saturated water solution thereof, the treatment taking place shortly after the bleaching step and before any appreciable color had been redeveloped in the bleached esters, for the purpose of removing the excess hydrogen peroxide and decomposing the color forming bodies, had a stability of hours which is more than five times the stability normally required. The tem-' perature of the stabilizing treatment is preferably about 75-80 C. Preferably, suflicient sodium bisulfite or other reducing agent is employed to insure the presence of at least a molecular equivalent thereof with respect to the hydrogen peroxide initially employed for the bleaching operation.
In another experiment, coco monoglycerides having an original Lovibond color of 3.5 red were intimatelycontacted with 0.25% by weight of a 30% H202 solution to give a bleached monoglyceride product having a color of 1.5 red. Although the color of this bleached product was good, color reversion began after a relatively short time so that the efiect of the bleaching operation eventually was rendered nugatory. However, upon treating another sample of freshly bleached product with an aqueous solution of sodium bisulfite in amount slightly in molecular excess relative to the H202 employed in the bleaching operation, a stabilized bleached monoglyceride ester product was obtained that retained its low 3 color from 5 to 8 times as long as in the absence of the bisulfite treatment.
Other bleached esters were similarly prepared. The amount of hydrogen peroxide required varied with the. color of the ester after the preliminary carbon or other bleach, as well as with the color required in the final product.
The fatty esters that may be treated by the process of the present invention include the natural fatty acid esters, such as fats or fatty oils suitable for employment in the soap-making or edible-fats industries, or any other fatty acid esters, whether of a polyhydric alcohol, such as glycerol or the glycols, or of a monohydric-alcohol, or mixtures of such esters. Of especial importance are esters of fatty acids of about 8 to 26, and preferably about 12 to 20, carbon atoms per molecule of fatty acid. Such fatty esters include coconut oil, palm oil, olive oil, cottonseed oil, corn oil, soya bean oil, tung oil, wool fat, tallow, whale and fish oils, etc., as well as the alkyl esters of the fatty acids corresponding to these oils, such as the methyl and ethyl esters. However, the invention is especially desirable in connection with the production of color-stabilized monoglyceride esters of high molecular weight fatty acids of the type indicated above.
All of the foregoing esters are relatively unstable and begin to revert to their original color only a relatively short while after the hydrogen peroxide treatment depending upon such factors as temperature, degree of aeration, etc., but when they are further treated with a suitable reducing agent such as sodium bisulfite to deactivate or remove the color-forming tendency of the bleached esters, they then remain stable as regards color for periods of time far in excess of normal in the absence of the stabilizing treatment described herein.
Generally speaking, the degree of improvement ranges from a factor of at least five to as high as ten to fifteen, in terms of the increase in time before redevelopment of color occurs.
What has been described above is the preferred embodiment of the invention, using sodium bisulfite as the reducing agent and hydrogen peroxide as the oxidizing agent, and showing the effect of treatment with these specific agents on monoglycerides. Other suitable sulfur-containing inorganic reducing agents may beused such as potassium bisulfite, .sodium or potassium sulfite, sulfur dioxide, sodium or potassium hydrosulfite, etc., care being taken when using reducing agents other than the alkali metal bisulfites to insure that acid conditions are presentso as to avoid soap formation. However, the bisulfites are generally preferred, particularly where'the final treated products are to be used in edible compositions.
Other oxidizing agents may be used such as alkali metal chorates and perchlorates, chlorine oxides such as the monoxide and dioxide, acetyl peroxide, benzoyl peroxide, etc. When using certain of these last-mentioned oxidizing agents it may be found necessary or desirable to wash the thusbleached esters to remove degradation products of those oxidizing agents, in which case the alkali metal bisulfite or other reducing agent may be conveniently added to the washing solution to bring about the desired stabilizing action according to the present invention.
Both the step of treating the esters with the oxidizing agent and the step of treating them with the reducing agent may be carried out under a wide variety of conditions. Somewhat elevated temperatures are preferably, but not necessarily, employed. The esters While undergoing treatment are preferably subjected to efficient agitation in order to bring about effective contact between the respective phases.
While specific examples of preferredrnethods embodying the present invention have been set forth above, it will be apparent that many changes and modifications may be made in the methods of procedure without departing from the spirit of the invention. It will therefore be understood that the examples cited and the particular proportions and methods of operation set forth above are intended to be illustrative only, and are not intended to limit the scope of the invention.
What is claimed is:
1. .A process for bleaching fatty acid esters that comprises contacting said esters with an oxidizing agent to bleach said esters and treating the bleached esters before any substantial discoloration thereof with a sulfur-containing inorganic reducing agent to remove'any "excess oxidizing agent and to deactivate any color-forming bodies.
2. A process for bleaching fatty acid esters that comprises contacting said esters with an oxidizing agent'selected from the group consist-- ing of hydrogen peroxide, alkali metal chlorates, alkali metal perchlorates, chlorine monoxide, chlorine dioxide, acetyl peroxide, and benzoyl peroxide to bleach said esters and treating the bleached esters before any substantial discoloration thereof with a sulfur-containing inorganic reducing agent selected from the group consisting of sodium bisulfite, potassium bisulfite, so dium sulfite, potassium sulfite, sulfur dioxide, so-' dium hydrosulfite, and potassium hydrosulfite'to remove any excess oxidizing agent and to decompose any color-forming bodies.
3. A process for bleaching fatty acid esters that comprises contacting said esters with hydrogen peroxide to bleach said esters and treating the bleached esters before any substantial discoloration thereof with sodium bisulfite to remove any excess hydrogen peroxide and to decompose any color-forming bodies.
4. A process for bleaching higher fatty acid monoglyceride esters that comprises contacting said esters with hydrogen peroxide to bleach said esters and treating the bleached esters before any substantial discoloration thereof with sufficient sodium bisulfite to insure at least a molecular equivalent thereof withrespect to'the hydrogen peroxide initiallyintroduced to remove any excess hydrogen peroxide and to deactivate any color-forming bodies, :thereby minimizing any tendency to color reversion.
5. A process as in claims, .in which the higher fatty acid glyceride is lard monoglyceride.
'6. A process as in claim 4, in which the'higher fatty acid glyceride is coconut monoglyceride.
7. A process for bleaching higher fatty acid monoglyceride esters that comprises contactingsaid esters with hydrogen peroxide to ibleach said esters and treating the bleachedesters before any substantial discoloration thereof with an aqueous solution of sodium bisulfite to remove any excess hydrogen peroxide: and to decompose any color-forming bodies, thereby minimizing any tendency to color reversion.
8. A process as in'claim 7, in-which the higher fatty acid glyceride is lard monoglyceride.
9. A process as in claim "7, in which the' higher fatty acid glyceride iscoconut monoglyceride.
10. A process for bleachingizhigherifatty acid monoglyceride esters that comprisesmontacting;
5 6 said esters with hydrogen peroxide to bleach said References Cited in the file of this patent esters and treating the bleached esters before any TENT substantial discoloration thereof with sodium bi- UNITED STATES PA 8 sulfite to remove any excess hydrogen peroxide Number Name Date and to decompose any color-forming bodies, 5 1,890,121 Lagasse 6, 1932 thereby minimizing any tendency to color re- 2,259,968 Andersen 1941 version 2,524,056 Jespersen Oct. 3, 1950 11. A process as in claim 10, in which the higher fatty acid glyceride is lard monoglyceride.
12. A process as in claim 10, in which the higher 10 fatty acid glyceride is coconut monoglyceride.
Claims (1)
1. A PROCESS FOR BLEACHING FATTY ACID ESTER THAT COMPRISES CONTACTING SAID ESTERS WITH AN OXIDIZING AGENT TO BLEACH SAID ESTERS AND TREATING THE BLEACHED ESTERS BEFORE ANY SUBSTANTIAL DISCOLORATION THEREOF WITH A SULFUR-CONTAINING INORGANIC REDUCING AGENT TO REMOVE ANY EXCESS OXIDIZING AGENT AND TO DEACTIVATE ANY COLOR-FORMING BODIES.
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Application Number | Priority Date | Filing Date | Title |
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US241394A US2684971A (en) | 1951-08-10 | 1951-08-10 | Bleaching and stabilization of fatty acid esters, including glycerides, especially monoglycerides |
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Application Number | Priority Date | Filing Date | Title |
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US241394A US2684971A (en) | 1951-08-10 | 1951-08-10 | Bleaching and stabilization of fatty acid esters, including glycerides, especially monoglycerides |
Publications (1)
Publication Number | Publication Date |
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US2684971A true US2684971A (en) | 1954-07-27 |
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US241394A Expired - Lifetime US2684971A (en) | 1951-08-10 | 1951-08-10 | Bleaching and stabilization of fatty acid esters, including glycerides, especially monoglycerides |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2937193A (en) * | 1957-02-15 | 1960-05-17 | Fond Emanuele Paterno | Olive oil refining process |
US9775909B2 (en) | 2012-06-15 | 2017-10-03 | Arkema Inc. | Peroxide dispersions |
US9861119B2 (en) | 2012-06-15 | 2018-01-09 | Arkema Inc. | Peroxide dispersions |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1890121A (en) * | 1930-05-31 | 1932-12-06 | Stockton G Turnbull | Process of bleaching soap stock |
US2259968A (en) * | 1938-09-30 | 1941-10-21 | Lever Brothers Ltd | Method of decolorizing oils |
US2524056A (en) * | 1947-03-15 | 1950-10-03 | Jespersen Vagn | Process for bleaching compounds of fatty acids or the like |
-
1951
- 1951-08-10 US US241394A patent/US2684971A/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1890121A (en) * | 1930-05-31 | 1932-12-06 | Stockton G Turnbull | Process of bleaching soap stock |
US2259968A (en) * | 1938-09-30 | 1941-10-21 | Lever Brothers Ltd | Method of decolorizing oils |
US2524056A (en) * | 1947-03-15 | 1950-10-03 | Jespersen Vagn | Process for bleaching compounds of fatty acids or the like |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2937193A (en) * | 1957-02-15 | 1960-05-17 | Fond Emanuele Paterno | Olive oil refining process |
US9775909B2 (en) | 2012-06-15 | 2017-10-03 | Arkema Inc. | Peroxide dispersions |
US9861119B2 (en) | 2012-06-15 | 2018-01-09 | Arkema Inc. | Peroxide dispersions |
US10925302B2 (en) | 2012-06-15 | 2021-02-23 | Arkema Inc. | Peroxide dispersions |
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