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Publication numberUS2690971 A
Publication typeGrant
Publication dateOct 5, 1954
Filing dateDec 16, 1950
Priority dateDec 16, 1950
Publication numberUS 2690971 A, US 2690971A, US-A-2690971, US2690971 A, US2690971A
InventorsIveson Herbert T, Julian Percy L, Radlove Sol B
Original AssigneeGlidden Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Edible shortening agent
US 2690971 A
Abstract  available in
Previous page
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Claims  available in
Description  (OCR text may contain errors)

Patented Qct. 5, 1954 EDIBLE SHORTENING AGENT Herbert T. Iveson, Berwyn, Sol B. Radlove, Chicago, and Percy L. Julian, Maywood, 111., assignors to The Glidden Company, Cleveland, Ohio, a corporation of Ohio No Drawing. Application December 16, 1950, Serial No. 201,226


This invention is concerned with shortening addition agents which are especially useful in cake :batters and the like. More specifically it is concerned with diglyceride reaction products which are prepared from glycerine, higher fatty acids and hydroxy carboxylic acids of proportions and characteristics described hereinafter.

In accordance with the present invention, glycerine and higher fatty acids are proportioned to form monoglycerides, or suitable alreadyformed monoglycerides may be provided. The fatty acids may be those of any of the common vegetable oils such as cottonseed, soya bean, coconut, and the like, or the oils themselves may be used to make the monoglycerides. In general, those higher fatty acids having an even number of carbon atoms from 12 to 20 and occurring quite commonly in nature in various oils and fats, have been found most suitable for the present invention, especially when palmitic acid amounts to at least about 50% of the total weight of fatty acids in the monoglycerides.

Monoglycerides have two of the hydroxyl groups of each glycerine molecule unesterified or free. In accordance with the present invention, such compounds are reacted with an organic mono-hydroxy carboxylic acid of not over six carbon atoms, for instance, having the general formula R.CHOH-COOH wherein R represents a hydrogen group or an hydrocarbon group having one to four carbon atoms. Lactic acid has been found very suitable, although other mono-hydroxy carboxylic acids such as glycollic acid, sarcolactic acid, hydracrylic acid, hydroxybutyric acid and malic acid may be used as well.

A reaction is caused to occur between proportions of glycerine, fatty acids and the hydroxy acid which should theoretically esterify not more than two of the hydroxyl groups of each glycerine molecule. In actual practice, however, small amounts of triglycerides are apt to be formed adventitiously. We desire to keep the triglyceride content as low as possible and preferably to exclude the triglycerides. Likewise in theory the resulting product should consist mainly of mixed diglycerides, but in actual practice the reactions are prone to yield some unmixed diglycerides such as dilactates, dipalmitates, etc., and appreciable quantities of monoglycerides. Moreover, the reaction product is apt to contain some monoglycerides or diglycerides of the type in which the OH group of the hydroxy carboxylic acid radical is esterified with a fatty acid, for example, a palmito-lactate monoglyceride. In spite of the numerous possibilities which may occur in the finished product, the analysis of the product shows that it averages at least one mol and not more than two mols of carboxylic acid per mol of glycerine. All glyceride reaction products of such average analysis are contemplated here. Such products will have at least one free OH group on the glycerine molecule and not more than an average of two free hydroxyl groups in the glycerine molecule (two on the glycerine molecule or one on the glycerine molecule and one on a lactate radical). The numerous combinations and relative proportions of OH groups, number of hydroxy acid radicals and number and chain length of fatty acid radicals in the various emulsifiers contemplated within the scope of our invention make it possible to vary the emulsification properties rather widely to suit them to different systems in which they are to be used. When used in all-purpose shortenings, however, we have found that the emulsifier is desirably formulated so as to have (1) about one equivalent mol of a mixture of myristic, palmitic and stearic acids, per mole of glycerine with palmitic acid amounting to at least by weight of the said mixture of fatty acids; (2) between about /2 and 1 mol of lactic acid per mole of glycerine; (3) about 40-50% of mixed hydroxy acid-fatty acid diglycerides; (4) about 25% of monoglycerides; and (5) balance substantially all diglycerides of the fatty acids. Such reaction mixtures will usually contain small amounts of triglycerides (less than about 1%) and may contain some unreacted Water-soluble lactides resulting from their unavoidable presence in the lactic acid used in preparing the emulsifier. Water-soluble materials contained in the emulsifier impair its flavor, so for the purpose of removing such materials the emulsifier is washed with a solution of sodium sulfate or sodium chlo- EXAMPLE 1 An emulsifier was prepared from the following ingredients: 1680 parts (6 mols) double-pressed, distilled, stearic acid having a mean molecular Weight of 265 and containing:

Per cent Stearic acid 41 Palmitic acid "a 51 Myristic acid 2 Oleic acid 6 618 parts (6 mols) 95% glycerine 420 parts (4 mols) 85% edible lactic acid containing about 72% free lactic acid in color, had a hardness similar to hard butter and broke with a fracture.

The efficacy of the emulsifier as a shortening agent for cakes was tested by blending various percentages of the emulsifier with the glyceride oil shortening component of the following household cake formula:

7% oz. cake flour 10 oz. sugar 3%; oz. shortening containing emulsifier oz. baking powder oz. salt 5 oz. milk The foregoing ingredients were mixed together for two minutes at a medium speed on a power mixer. Then 3 oz. milk 4 oz. egg white /4 oz. vanilla extract were added and the whole was mixed for two minutes more at a medium speed. 15 oz. of the batter was weighed into an eight-inch pan and the batter was baked at 365 F. for 21 minutes. The volume of the cake and other characteristics, after baking, were determined and the respective volumes obtained from different percentages of emulsifier by weight on the shorten ing were correlated and are shown in the following tabulation:

Percent Emulslficr, Kind g Texture Top Porosity Better 4 Best commercial emulsifier l,l50 Good..- Smooth... Good... Slightly curdled 2% Emulsifier as prepared in Ex- 1,150 do Smooth ample 1. 3 .(lo 1,235 -do. do .dc Do. 4 do 1,240 do. .do Do

The stearic acid and glycerine were mixed and heated to about 140 C. The lactic acid was warmed separately to about 80 C. and was then added to the hot mixture of stearic acid and glycerine. The whole mass was then heated rapidly to 185 C., and carbon dioxide was bubbled through the molten materials for one hour while the temperature was maintained at 185 C. A vacuum of 10-12" was then applied, the carbon dioxide being continued, and the mixture was treated under these conditions for an additional 6 hours. A system of reflux was used which ensured complete and continuous removal of water formed by the reaction of the materials, yet insured condensation of the lactic acid. At the end of the six-hour period the vacuum was increased to 22"-26", the carbon dioxide was continued, and the reaction mass was heated at 185 C. for a further period of three hours. The material was then allowed to cool to 90-l00 C. 2426 parts of reaction product thus secured was washed three times with 1500 parts of a hot 3% sodium sulfate solution, after which .33 part (.015%) citric acid was added to stabilize the product. The product was then dried on a steam bath under vacuum to yield 2140 parts of emulsifier having an acid number of '7, an acetyl value of about 150, a saponification value of about 218 and a monoglyceride content of 24.5%. The emulsifier had good flavor, was light tan to cream In blending the difierent emulsifiers with the shortening component of the above cake formula, the procedure employed was to melt the emulsifier with about 3 times its weight of the shortening component, and then to thoroughly mix the melted materials into the remainder of the shortening component. It was found that this procedure gave reproducible results at all emulsifier levels.

From the foregoing tests on cakes, it will be observed that our emulsifier not only increased the volume of the cake over that obtained from the commercial emulsifier, but also accomplished this result with a smaller percentage on the shortening.

EXAMPLE 2 An emulsifier was prepared exactly as decribed in Example 1 except that a ratio of glycerine, stearic acid and edible lactic acid of 1 to 1 to 1 was used.

224.0 g. (0.8 M) double pressed stearic acid 92.0 g. (0.8 M) edible lactic acid 82.4 g. (0.8 M) glycerol EXAMPLE 3 Another emulsifier was prepared as follows:

168.0 g. (0.6 M) double pressed stearic acid 61.8 g. (0.6 M) 95% glycerol 414.0 g. (0A M) 70% glycolic acid Were reacted in the manner previously described. 203 grams of material was obtainedwith an acid number of 8.1, a saponification value of 221.4, and a monoglyceride content of 16.4%.

Since this is not an edible material, it was not tested in cakes, but qualitatively it showed good emulsifying properties when tested in laboratory test tube experiments.

EXAMPLE 4 200 grams of mixture of hydrogenated soybean oil and cottonseed oil was heated to 165l75 C. A solution of 0.4 gram of NaOH dissolved in a little water and 36 grams of 95% glycerol was then quickly added. The mixture was heated for 30 minutes at about 185 C. under vacuum. When the mixture became almost clear, 36 grams of 85% lactic acid was added and the entire reaction mixture heated for 2 hours at 185 C. under approximately 22" of vacuum. 235 grams of final dried material was obtained having an acid number of 1.65, a saponification number of 204, an acetyl value of 140, and a monoglyceride content of 21.4%.

From the foregoing description and examples of our invention, it will be understood that our invention is concerned with the preparation and provision of emulsifiers having an average composition not exceeding that of a diglyceride and not less than a monoglyceride, with an hydroxy carboxylic acid component therein between about /2 and 1 mol per mol of glycerine. While we have found that the natural mixture of products resulting from the reaction of the outlined proportions of ingredients constitutes useful shortening agent emulsifiers, it will also be understood that the individual mixed diglyceride components of such natural mixtures may be separated from the mixture for use as emulsifiers in a relatively pure state.

Various commercial fatty acid products may be used in practicing the invention. Thus, triple-pressed stearic acid may be used to introduce the following acids:

Per cent Stearic acid 46.5

Palmitic acid 50.0

Myristic acid 0.5 Oleic acid 3.0

Neofat I-56 (Armour and Company) contains about 93% palmitic acid, I-Iystrene '70 (Atlas Powder Company) contains about 70% stearic acid, I-Iystrene 97 (Atlas Powder Company) contains 97% stearic acid. Many other commercial products are also well known and may be selected for use in the invention in accordance with the principles set forth hereinabove.

Having now disclosed our invention, what we claim is:

1. The compositions of matter obtained by (l) refluxing the following proportioned ingredients at about 185 C. in a vacuum with removal of water and with condensation and return of monohydroxy monocarboxylic acid, (2) sparging the resulting mass with CO2 in vacuo at about C. until the acid number of the reaction mixture is below about 8.1 and (3) Washing said sparged mass until substantially free of water-soluble materials: 1 molar equivalent of glycerine, 1 molar equivalent of higher fatty acids having between .12 and 20 carbons, of which at least 50% by weight is palmitic acid, and from ,4 to 1 molar equivalent of monohydroxy monocarboxylic acid of from 2 to 6 carbons, inclusive; said washed composition consisting essentially of: (a) an average total of at least one molar equivalent and not more than 2 molar equivalents of carboxylic acid per mol of glyceride ester, whereby the average molecule of glyceride ester contains at least one and not more than two unesterified glyceryl hydroxyl groups, (b) an average of at least one and not more than 2 monohydroxy monocarboxylic acid radicals per two mols of glyceride ester, (0) an average total of at least 2 and not more than 4 esterifiable hydroxyl groups per two mols of glyceride ester, ((1) at least 16 of monoglycerides by weight on said washed composition, and (e) not more than small amounts of triglycerides, said composition having a saponification value between about 204 and 242.

2. A composition as claimed in claim 1 wherein mixed diglycerides of fatty acids and hydroxy acids account for between about 40% and 50% of the total composition, wherein monoglycerides account for about 25% of the total, and wherein diglycerides of said higher fatty acids plus small amounts of triglycerides account for substantially all of the remainder.

3. A composition as claimed in claim 1 wherein the monohydroxy monocarboxylic acid radicals are lactic acid radicals.

4. A composition as claimed in claim 3 wherein mixed diglycerides of said higher fatty acids and lactic acid account for between about 40% and 50% of the total composition, wherein monoglycerides account for about 25% of the total, and wherein diglycerides of said higher fatty acids plus small amounts of triglycerides account for substantially all of the remainder.

5. A composition as claimed in claim 4 wherein the fatty acids consist of acids having between 14 and 18 carbon atoms.

6. A shortening agent comprising: an edible glyceride oil having shortening properties, and a composition as claimed in claim 1.

7. A shortening agent comprising: an edible glyceride oil having shortening properties, and a composition as claimed in claim 2.

8. A shortening agent comprising: edible glyceride oil having shortening properties, and a composition as claimed in claim 3.

9. A shortening agent comprising: an edible glyceride oil having shortening properties, and a composition as claimed in claim 4.

10. A shortening agent comprising: an edible glyceride oil having shortening properties, and a composition as claimed in claim 5.

References Cited in the file of this patent UNITED STATES PATENTS Number

Patent Citations
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Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US2744825 *May 10, 1954May 8, 1956Patterson Co CAcyl lactylic acid products
US2744826 *Feb 3, 1954May 8, 1956Patterson Co CFlour composition
US2745749 *Jul 19, 1951May 15, 1956Feuge Reuben OGlyceridic mixtures exhibiting unique properties and process for their production
US2864703 *Apr 1, 1954Dec 16, 1958Glenn LabLiquid shortenings and method of improving baked goods
US2864705 *Aug 31, 1954Dec 16, 1958Glenn LabLiquid shortenings
US2957932 *Aug 4, 1954Oct 25, 1960Glidden CoOil-soluble emulsifying agent
US2963371 *Oct 14, 1957Dec 6, 1960Swift & CoEmulsifying agents in shortening and process of producing same
US2966412 *Dec 14, 1959Dec 27, 1960Rath Packing CompanyItaconic acid-modified triglyceride shortening composition and method of preparing the same
US2968562 *Jan 21, 1958Jan 17, 1961Nat Dairy Prod CorpShortening
US2970055 *Dec 14, 1959Jan 31, 1961Rath Packing CompanyTriglyceride shortening composition and method for preparing the same
US2978329 *Jul 29, 1957Apr 4, 1961Glidden CoProcess of preparing yeast-leavened baked goods
US2982662 *Jul 10, 1957May 2, 1961Glidden CoProcess of preparing batters adapted for refrigerated storage
US3004853 *May 13, 1958Oct 17, 1961Glidden CoShortening composition and emulsifier system therefor
US3011896 *Jan 19, 1960Dec 5, 1961Glidden CoFluid shortening and process for making the same
US3012048 *Jul 14, 1959Dec 5, 1961Armour & CoMethod of making mixed glycerol esters of fatty and lactic acids
US3029147 *Nov 23, 1959Apr 10, 1962Radlove Sol BLiquid shortenings and method of improving baked goods
US3042530 *Jan 16, 1959Jul 3, 1962Swift & CoShortening emulsifier and method for preparing the same
US3051577 *Jul 2, 1959Aug 28, 1962Drew Chem CorpGlyceryl lacto esters in coatings
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US3098748 *Mar 24, 1960Jul 23, 1963Noznick Peter PWhipping and powdered shortening compositions
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US4363763 *Dec 24, 1980Dec 14, 1982The Procter & Gamble CompanyDetergent surfactants
US4469635 *Apr 22, 1982Sep 4, 1984The Procter & Gamble CompanyEmulsifiers
US4582715 *Dec 4, 1984Apr 15, 1986The Procter & Gamble CompanyAcylated glycerides useful in low calorie fat-containing food compositions
DE1032653B *Apr 6, 1956Jun 19, 1958Procter & GambleVerfahren zur Herstellung eines insbesondere zur Anfertigung von bei niedrigen Temperaturen stabiler Mayonnaise geeigneten Salatoels
DE1045776B *Apr 9, 1956Dec 4, 1958Procter & GambleVerfahren zur Herstellung eines zur Anfertigung von bei niedrigen Temperaturen stabiler Mayonnaise geeigneten Salatoels
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U.S. Classification426/611, 554/227, 426/612, 426/654
International ClassificationC11C3/02, C11C3/00
Cooperative ClassificationC11C3/02
European ClassificationC11C3/02