GB452138A - Manufacture of esters of polyglycerols - Google Patents

Manufacture of esters of polyglycerols

Info

Publication number
GB452138A
GB452138A GB3244934A GB3244934A GB452138A GB 452138 A GB452138 A GB 452138A GB 3244934 A GB3244934 A GB 3244934A GB 3244934 A GB3244934 A GB 3244934A GB 452138 A GB452138 A GB 452138A
Authority
GB
United Kingdom
Prior art keywords
oil
acids
esterified
polyglycerols
mixture
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB3244934A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EMULSOL CORP
Original Assignee
EMULSOL CORP
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EMULSOL CORP filed Critical EMULSOL CORP
Priority to GB3244934A priority Critical patent/GB452138A/en
Publication of GB452138A publication Critical patent/GB452138A/en
Expired legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A23D7/0056Spread compositions
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/01Other fatty acid esters, e.g. phosphatides
    • A23D7/013Spread compositions
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11CFATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/02Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
    • C11C3/025Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol with a stoechiometric excess of glycerol

Abstract

Polyglycerols obtained by polymerizing glycerine with the aid of an alkaline catalyst at a temperature below 260 DEG C. in a non-oxidizing atmosphere, preferably at subatmospheric pressure, are (a) esterified with a monobasic acid or an anhydride or halide of such an acid, or with a mixture of such acids, anhydrides or halides, or (b) re-esterified with a triglyceride of a monobasic acid, or a mixture of such triglycerides; the esterification or re-esterification is effected at below 250 DEG C. in a non-oxidizing atmosphere in the presence of an alkaline catalyst, preferably at subatmospheric pressure, and the proportions are such that the products contain at least one unesterified hydroxy group. In examples of the preparation of polyglycerols: (1) glycerol is heated to 225--230 DEG C. with 1 per cent of caustic soda under a reflux condenser kept at about 100 DEG C. and with a stream of carbon dioxide passing through the mixture; a product of molecular weight 166 is obtained; (2) the same mixture as in example 1 is heated in carbon dioxide to 220--225 DEG C. while the pressure is reduced in stages to 70 mm., this yielding a product of molecular weight 256; (3) the product of example 1 is freed from unpolymerized glycerol by distillation at 235 DEG C. and 2--5 mm. pressure with a stream of inert gas bubbled through the liquid. Other alkaline catalysts which may be used are sodium carbonate and bicarbonate, other alkali carbonates and hydroxides, oxides of calcium, magnesium and zinc, trisodium phosphate and sodium tetraborate. In examples of the esterification of polyglycerols, (4) the product of example 3, still containing the alkaline catalyst, is heated to 220--230 DEG C. with oleic and stearic acids in an atmosphere of carbon dioxide; (5) the product of example 3 is heated to 205 DEG C. under 35--50 mm. pressure with the acids of hydrogenated cottonseed oil in an atmosphere of nitrogen. Other specified acids which may be used are acetic, propionic, butyric, valeric, caprylic, caproic, capric, lauric, myristic, palmitic, ricinoleic, hydroxystearic, behenic, linoleic, linolenic, naphthenic, benzenesulphonic, naphthalenesulphonic, cetylsulphonic, dodecylsulphonic, benzoic and naphthoic acids, and the acids derived from coconut oil, palm-kernel oil, tallow, oleo oil, oleostearine, palm oil, cottonseed oil, soy oil, corn oil, sunflower oil, sesame oil, linseed oil, whale oils, fish oils, lard and rosin, and their hydrogenation products; the specified oils and fats may be used also in the re-esterification process. The polyglycerols and their esters may be improved in odour and taste by steam treatment at atmospheric or reduced pressure. The esters are useful as antispattering additions to margarine, as emulsifying agents, particularly in edible emulsions such as cake batters and shortenings, and also as wetting agents. Specification 421,284 is referred to. The Specification as open to inspection under Sect. 91 includes four further examples of the preparation of polyglycerols, generally similar to examples 1 and 2 above, in which products of molecular weights 148--163, 326, 179, and 207 are obtained. Sodium acetate, iodine and zinc chloride are additional specified catalysts for use in the production of polyglycerols. The Specification also includes two further examples, generally similar to example 3 above, of the removal of glycerol from polyglycerols by distillation, products of the molecular weights 205 and 345 being obtained. An example in which a polyglycerol is refined by steam treatment at 180--200 DEG C. and 50--20 mm. pressure is also included, as well as two additional esterification examples in which (1) a polyglycerol of molecular weight 256 is esterified with stearic acid, substantially as in example 4 above and (2) the polyglycerol stearate so obtained is heated again under similar conditions with stearic acid. This subject-matter does not appear in the Specification as accepted.ALSO:Polyglycerols are (a) esterified with a monobasic acid or an anhydride or halide of such an acid, or with a mixture of such acids, anhydrides or halides, or (b) re-esterified with a triglyceride of a monobasic acid, or a mixture of such triglycerides; the proportions are such that the products contain at least one unesterified hydroxy group. Examples are given in which a polyglycerol is esterified with a mixture of oleic and stearic acids and with the acids of hydrogenated cottonseed oil. Other specified acids which may be used are acetic, propionic, butyric, valeric, caprylic, caproic, capric, lauric, myristic, palmitic, ricinoleic, hydroxystearic, behenic, linoleic, linolenic, naphthenic, benzenesulphonic, naphthalenesulphonic, cetylsulphonic, dodecylsulphonic, benzoic and naphthoic acids, and the acids derived from coconut oil, palm-kernel oil, tallow, oleo oil, oleostearine, palm oil, cottonseed oil, soy oil, corn oil, sunflower oil, sesame oil, linseed oil, whale oils, fish oils, lard and rosin, and their hydrogenation products; the specified oils and fats may be used also in the re-esterification process. The esters are useful as emulsifying agents, particularly in edible emulsions such as cake batters and shortenings. Specification 421,284, [Group IV], is referred to. The Specification as open to inspection under Sect. 91 includes two additional examples in which (1) a polyglycerol of molecular weight 256 is esterified with stearic acid, and (2) the polyglycerol stearate so obtained is heated again under similar conditions with stearic acid. This subject-matter does not appear in the Specification as accepted.ALSO:Polyglycerols are (a) esterified with a monobasic acid or an anhydride or halide of such an acid, or with a mixture of such acids, anhydrides or halides, or (b) re-esterified with a triglyceride of a monobasic acid, or a mixture of such triglycerides. Examples are given in which a polyglycerol is esterified with a mixture of oleic and stearic acids and with the acids of hydrogenated cottonseed oil. Other specified acids which may be used are acetic, propionic, butyric, valeric, caprylic, caproic, capric, lauric, myristic, palmitic, ricinoleic, hydroxystearic, behenic, linoleic, linolenic, naphthenic, benzenesulphonic, naphthalenesulphonic, cetylsulphonic, dodecylsulphonic, benzoic and naphthoic acids, and the acids derived from coconut oil, palm-kernel oil, tallow, oleo oil, oleostearine, palm oil, cottonseed oil, soy oil, corn oil, sunflower oil, sesame oil, linseed oil, whale oils, fish oils, lard and rosin, and their hydrogenation products; the specified oils and fats may be used also in the re-esterification process. The esters may be improved in odour and taste by steam treatment at atmospheric or reduced pressure. They are useful as antispattering additions to margarine. Specification 421,284, [Group IV], is referred to. The Specification as open to inspection under Sect. 91 includes two additional examples in which (1) a polyglycerol of molecular weight 256 is esterified with stearic acid, and (2) the polyglycerol stearate so obtained is heated again under similar conditions with stearic acid. This subject-matter does not appear in the Specification as accepted.
GB3244934A 1934-11-10 1934-11-10 Manufacture of esters of polyglycerols Expired GB452138A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3244934A GB452138A (en) 1934-11-10 1934-11-10 Manufacture of esters of polyglycerols

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3244934A GB452138A (en) 1934-11-10 1934-11-10 Manufacture of esters of polyglycerols

Publications (1)

Publication Number Publication Date
GB452138A true GB452138A (en) 1936-08-10

Family

ID=10338755

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3244934A Expired GB452138A (en) 1934-11-10 1934-11-10 Manufacture of esters of polyglycerols

Country Status (1)

Country Link
GB (1) GB452138A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2506695A (en) * 1947-09-11 1950-05-09 Interchem Corp Composition of matter
US3222145A (en) * 1960-12-28 1965-12-07 Gulf Research Development Co Stabilization of thermally unstable liquid hydrocarbon fuels
US5597934A (en) * 1991-07-25 1997-01-28 Henkel Kommanditgesellschaft Auf Aktien Process for production of polyol compounds

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2506695A (en) * 1947-09-11 1950-05-09 Interchem Corp Composition of matter
US3222145A (en) * 1960-12-28 1965-12-07 Gulf Research Development Co Stabilization of thermally unstable liquid hydrocarbon fuels
US5597934A (en) * 1991-07-25 1997-01-28 Henkel Kommanditgesellschaft Auf Aktien Process for production of polyol compounds

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