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WO2008059220A1 - Procédé de préparation d'émulsifiants non hydrogénés - Google Patents

Procédé de préparation d'émulsifiants non hydrogénés Download PDF

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Publication number
WO2008059220A1
WO2008059220A1 PCT/GB2007/004315 GB2007004315W WO2008059220A1 WO 2008059220 A1 WO2008059220 A1 WO 2008059220A1 GB 2007004315 W GB2007004315 W GB 2007004315W WO 2008059220 A1 WO2008059220 A1 WO 2008059220A1
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WO
WIPO (PCT)
Prior art keywords
acid esters
oil
emulsifier
hydrogenated
triglyceride
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.)
Ceased
Application number
PCT/GB2007/004315
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English (en)
Inventor
Allan Torben Bech
Paul Wassell
Marianne Hornholt
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.)
International N&H Denmark ApS
Original Assignee
Danisco AS
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Filing date
Publication date
Application filed by Danisco AS filed Critical Danisco AS
Publication of WO2008059220A1 publication Critical patent/WO2008059220A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
    • C11C3/025—Fats, 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/01—Other fatty acid esters, e.g. phosphatides
    • A23D7/011—Compositions other than spreads
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/30—Cocoa products, e.g. chocolate; Substitutes therefor
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/30—Cocoa products, e.g. chocolate; Substitutes therefor
    • A23G1/32—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds
    • A23G1/36—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds characterised by the fats used
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G9/00—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G9/00—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
    • A23G9/32—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds
    • A23G9/327—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds characterised by the fatty product used, e.g. fat, fatty acid, fatty alcohol, their esters, lecithin, glycerides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G2200/00—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents
    • A23G2200/08—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents containing cocoa fat if specifically mentioned or containing products of cocoa fat or containing other fats, e.g. fatty acid, fatty alcohol, their esters, lecithin, paraffins

Definitions

  • the present invention relates to a method of preparing a non-hydrogenated emulsifier having substantially no trans carbon-carbon double bonds.
  • the present invention also relates to a non-hydrogenated emulsifier, foodstuffs containing the emulsifier and uses of the emulsifier.
  • trans fatty acids that is fatty acids containing trans isomers of carbon-carbon double bonds
  • trans fatty acids may contribute to problems with the human circulatory system.
  • evidence suggests that consumption of trans fatty acids may raise low-density lipoprotein cholesterol levels, and lower high-density lipoprotein cholesterol levels, which can contribute to causing arteries to become clogged and increasing the risk of a stroke and of developing heart disease.
  • trans fatty acids may be formed during hydrogenation or partially hydrogenation processes that have been commonly used in the preparation of food product formulations.
  • WO 2006/029139 teaches a fat composition which contains low levels of trans fats, and includes a mixture of palm kernel oil and palm oil. It also teaches the use of this fat composition in a confectionary composition.
  • EP 1159877 discloses a margarine and spread fat blend containing a trans free hard structural fat.
  • This structural fat is made from selectively fractionated non-hydrogenated palm oil fraction which is interesterified with dry fractionated non-hydrogenated palm kernel fraction.
  • trans fatty acid residues may be present in food ingredients other than fat compositions.
  • fatty acid residues are present in emulsifiers.
  • the present invention alleviates the problems of the prior art.
  • the present invention provides a method of preparing a non-hydrogenated emulsifier having substantially no trans carbon-carbon double bonds comprising: (i) an interesterification step comprising a polyol compound and a non-hydrogenated triglyceride, wherein the triglyceride has an iodine value of less than 9 and substantially no trans carbon-carbon double bonds.
  • the present invention provides a non-hydrogenated emulsifier having substantially no trans carbon-carbon double bonds comprising: (a) mono-fatty acid esters of a polyol compound; and/or
  • the present invention provides a foodstuff or food ingredient comprising a non-hydrogenated emulsifier of the present invention.
  • the present invention provides a use of a non-hydrogenated emulsifier according to the present invention in a foodstuff or food ingredient selected from a bakery product, bread improver, chocolate, chocolate spread, dairy product, fat based confectionary filling, fat based icing, frozen dairy product, low-fat spread, margarine, frying margarine, peanut butter, salad dressing, shortening, tahina, soluble food or drink powders, vegetable ghee and whipped food product.
  • a foodstuff or food ingredient selected from a bakery product, bread improver, chocolate, chocolate spread, dairy product, fat based confectionary filling, fat based icing, frozen dairy product, low-fat spread, margarine, frying margarine, peanut butter, salad dressing, shortening, tahina, soluble food or drink powders, vegetable ghee and whipped food product.
  • the present invention provides a use of a non-hydrogenated emulsifier according to the present invention to prepare a food grade emulsion, foam, dispersion, or an anhydrous based lipid preparation.
  • the present invention provides a composition comprising: (r) a non-hydrogenated palm stearine triglyceride having substantially no trans carbon- carbon double bonds with an iodine value of 15 or less; and (s) a non-hydrogenated emulsifier having substantially no trans carbon-carbon double bonds comprising:
  • di-fatty acid esters of a polyol compound di-fatty acid esters of a polyol compound
  • carboxylic acid esters of (a) and/or (b) wherein the carboxylic acid esters are selected from acetic acid esters, citric acid esters, lactic acid esters and diacetyltartaric acid esters; wherein the fatty acids are derived from a triglyceride having an iodine value of less than 9 and substantially no trans carbon-carbon double bonds.
  • the present invention provides an emulsifier composition
  • an emulsifier composition comprising: (x) a non-hydrogenated palm stearine monoglyceride and/or palm stearine diglyceride having substantially no trans carbon-carbon double bonds with an iodine value of 15 or less; and
  • di-fatty acid esters of a polyol compound di-fatty acid esters of a polyol compound
  • carboxylic acid esters of (a) and/or (b) wherein the carboxylic acid esters are selected from acetic acid esters, citric acid esters, lactic acid esters and diacetyltartaric acid esters; wherein the fatty acids are derived from a triglyceride having an iodine value of less than 9 and substantially no trans carbon-carbon double bonds.
  • a polyol compound is a compound comprising two or more hydroxy! groups.
  • the polyol compound is selected from a glycol compound and a glycerol compound.
  • the polyol compound is selected from a glycol compound and glycerol.
  • the polyol compound is a glycol compound.
  • the glycol compound is propylene glycol.
  • the polyol compound is a glycerol compound.
  • the glycerol compound is selected from glycerol and a polyglycerol.
  • the polyol compound is selected from propylene glycol, glycerol and a polyglycerol.
  • the polyol compound is glycerol.
  • the glycerol compound is a polyglycerol.
  • the polyglycerol has from 2 to 10 glycerol units in the polyglycerol chain.
  • the polyglycerol is selected from 1 ,1'-diglycerol, 1 ,2'-diglycerol and 1,1,1'- triglycerol.
  • the interesterification step (i) is carried out in the presence of an alkaline catalyst.
  • alkaline catalysts may be selected from potassium hydroxide, sodium hydroxide and sodium methoxide.
  • the method comprising the further step of isolating monoglycerides from the product of step (i).
  • the monoglycerides are isolated by distillation.
  • Acetylation may be carried out with any suitable acetylating agent.
  • the acetylating reagent is selected from acetic acid, acetyl chloride, acetyl bromide, acetyl iodide, acetyl fluoride, N-acetyl imidazole and acetic anhydride.
  • the acetylating reagent is selected from acetyl chloride and acetic anhydride.
  • the acetylating reagent is acetic anhydride.
  • the interesterification step (i) further comprises triacetin.
  • step (ii) of esterification of the product of step (i) is carried out in the presence of a tertiary amine.
  • a tertiary amine which can be used may be selected from triethylamine, tributylamine, diisopropylethylamine, pyridine, A- dimethylaminopyridine and mixtures thereof.
  • the further step: (ii) of esterification of the product of step (i) may be carried out in an inert solvent.
  • the solvent is selected from chlorinated hydrocarbons, such as chloroform and dichloromethane; ethers, such as diethyl ether and tetrahydrofuran; low molecular weight esters, such as ethyl acetate and butyl acetate; low molecular weight aliphatic ketones, such as acetone and methyl ethyl ketone; tertiary amides, such as N,N-dimethyl formamide and N-methylpyrridone; acetonitrile; and mixtures thereof.
  • the triglyceride is prepared by selective fractionation and/or winterisation and/or solvent extraction of an edible fat or oil.
  • the edible fat or oil is crystallised and/or condensed at controlled temperatures and fractionated to provide a stearin fraction, removing the olein fraction.
  • this stearin fraction is further fractionated one or more times to provide a non-hydrogenated triglyceride with the desired iodine value and substantially no trans carbon-carbon double bonds.
  • the selective fractionation is dry fractionation.
  • the proportion of fatty acid residues in the triglyceride comprising 12 carbon atoms or less is less than 40%; preferably less than 35%, less than 30%, less than 25%, less than 20%, less than 15%, less than 10%, less than 5%.
  • the proportion of fatty acid residues in the triglyceride comprising 14 carbon atoms or more is at least 40%; preferably at least 50%, at least 55%, at least 60%, at least 70%, at least 80%, at least 90%.
  • the proportion of fatty acid residues in the triglyceride comprising 16 carbon atoms or more is at least 40%; preferably at least 50%, at least 55%, at least 60%, at least 70%, at least 80%, at least 90%.
  • the proportion of fatty acid residues in the triglyceride comprising 18 carbon atoms or more is at least 40%; preferably at least 50%, at least 55%, at least 60%, at least 70%, at least 80%, at least 90%.
  • the proportion of fatty acid residues in the triglyceride comprising 20 carbon atoms or more is at least 40%; preferably at least 50%, at least 55%, at least 60%, at least 70%, at least 80%, at least 90%.
  • the proportion of fatty acid residues in the triglyceride comprising 22 carbon atoms or more is at least 40%; preferably at least 50%, at least 55%, at least 60%, at least 70%, at least 80%, at least 90%.
  • the proportion of fatty acid residues in the triglyceride comprising from 12 to 24 carbon atoms is at least 90%.
  • the proportion of fatty acid residues in the triglyceride comprising from 14 to 24 carbon atoms is at least 60%, preferably at least 70%, at least 80%, at least 90%.
  • the proportion of fatty acid residues in the triglyceride comprising from 16 to 24 carbon atoms is at least 60%, preferably at least 70%, at least 80%, at least 90%. In a further aspect, preferably the proportion of fatty acid residues in the triglyceride comprising from 18 to 24 carbon atoms is at least 60%, preferably at least 70%, at least 80%, at least 90%.
  • the proportion of fatty acid residues in the triglyceride comprising from 20 to 24 carbon atoms is at least 60%, preferably at least 70%, at least 80%, at least 90%.
  • the proportion of fatty acid residues in the triglyceride comprising from 22 to 24 carbon atoms is at least 60%, preferably at least 70%, at least 80%, at least 90%.
  • the triglyceride is derived from a fat or oil selected from alfalfa oil, allanblackia seed oil, apricot kernal oil, argane oil, artemisia oil, Australian golden jajoba oil, avocado butter, avocado oil, babassu oil, baobab oil, blackcurrant seed oil, borage (starflower) oil, brazil nut oil, butter oil, camellia oil, canola oil, carrot oil, cashew nut oil, caster oil, chaulmoogra oil, cherry pit oil, chia oil, cocoa butter, coconut oil, coffee oil, corn oil, coriander oil, cotton seed oil, evening primrose oil, foraha oil, gold of pleasure oil, grape seed oil, hazelnut oil, hemp oil, hyptis oil, illipe butter, juniper berry oil, kenaf oil, kiwi seed oil, kokum butter, kukui nut oil, linseed oil, macadamia nut
  • the triglyceride is derived from an edible fat or oil selected from allanblackia seed oil, babassu oil, butter oil, canola oil, coconut oil, cotton seed oil, foraha oil, kokum butter, palm oil, pentadesma butter, rapeseed oil, rice bran oil, sal butter and shea butter.
  • the triglyceride is derived from an edible fat or oil selected from allanblackia seed oil, butter oil, canola oil, cotton seed oil, foraha oil, kokum butter, palm oil, pentadesma butter, rapeseed oil, rice bran oil, sal butter and shea butter.
  • the triglyceride is derived from palm oil.
  • the triglyceride has a melting point of at least 40 0 C; preferably at least 45 0 C; at least 50 0 C; at least 55 0 C; at least 60 0 C; at least 65 0 C; at least 70 0 C; at least 75 0 C; at least 80 "C; at least 85 0 C; at least 90 0 C; at least 95 0 C; at least 100 0 C.
  • the emulsifier comprises mono-fatty acid esters and di-fatty acid esters of a polyol compound selected from propylene glycol, glycerol and a polyglycerol.
  • the emulsifier comprises mono-fatty acid esters and di-fatty acid esters of glycerol.
  • the emulsifier comprises mono-fatty acid esters of glycerol.
  • the emulsifier comprises di-fatty acid esters of glycerol.
  • the emulsifier comprises: (c) carboxylic acid esters of (a) mono-fatty acid esters of a polyol compound, and/or acid esters of (b) di-fatty acid esters of a polyol compound; wherein the carboxylic acid esters are selected from acetic acid esters, citric acid esters, lactic acid esters and diacetyltartaric acid esters.
  • the polyol is glycerol.
  • one of the R groups is a fatty acid residue (e.g. -C(O)-(CH 2 )i 4 -CH 3 ); a second of the R groups is an acetic acid ester residue (i.e. -C(O)CH 3 ); and the third R group is either a hydrogen, or an acetic acid residue.
  • a fatty acid residue e.g. -C(O)-(CH 2 )i 4 -CH 3
  • a second of the R groups is an acetic acid ester residue (i.e. -C(O)CH 3 )
  • the third R group is either a hydrogen, or an acetic acid residue.
  • the present invention provides a non-hydrogenated emulsifier having substantially no trans carbon-carbon double bonds comprising (d) monoglycerides and/or (e) diglycerides and/or (f) carboxylic acid esters of monoglycerides and/or (g) carboxylic acid esters of diglycerides; wherein the carboxylic acid esters are selected from acetic acid esters, citric acid esters, lactic acid esters and diacetyltartaric acid esters; wherein the fatty acids of the monoglycerides and/or diglycerides are derived from a triglyceride having an iodine value of less than 9 and substantially no trans carbon- carbon double bonds.
  • the emulsifier comprises mono- and diglycerides.
  • the emulsifier comprises monoglycerides.
  • the emulsifier comprises diglycerides.
  • the proportion of fatty acid residues in the emulsifier comprising 12 carbon atoms or less is less than 40%; preferably less than 35%, less than 30%, less than 25%, less than 20%, less than 15%, less than 10%, less than 5%.
  • the proportion of fatty acid residues in the emulsifier comprising 14 carbon atoms or more is at least 40%; preferably at least 50%, at least 55%, at least 60%, at least 70%, at least 80%, at least 90%.
  • the proportion of fatty acid residues in the emulsifier comprising 16 carbon atoms or more is at least 40%; preferably at least 50%, at least 55%, at least 60%, at least 70%, at least 80%, at least 90%.
  • the proportion of fatty acid residues in the emulsifier comprising 18 carbon atoms or more is at least 40%; preferably at least 50%, at least 55%, at least 60%, at least 70%, at least 80%, at least 90%.
  • the proportion of fatty acid residues in the emulsifier comprising 20 carbon atoms or more is at least 40%; preferably at least 50%, at least 55%, at least 60%, at least 70%, at least 80%, at least 90%.
  • the proportion of fatty acid residues in the emulsifier comprising 22 carbon atoms or more is at least 40%; preferably at least 50%, at least 55%, at least 60%, at least 70%, at least 80%, at least 90%.
  • the proportion of fatty acid residues in the emulsifier comprising from 12 to 24 carbon atoms is at least 90%.
  • the proportion of fatty acid residues in the emulsifier comprising from 14 to 24 carbon atoms is at least 60%, preferably at least 70%, at least 80%, at least 90%.
  • the proportion of fatty acid residues in the emulsifier comprising from 16 to 24 carbon atoms is at least 60%, preferably at least 70%, at least 80%, at least 90%.
  • the proportion of fatty acid residues in the emulsifier comprising from 18 to 24 carbon atoms is at least 60%, preferably at least 70%, at least 80%, at least 90%.
  • the proportion of fatty acid residues in the emulsifier comprising from 20 to 24 carbon atoms is at least 60%, preferably at least 70%, at least 80%, at least 90%.
  • the proportion of fatty acid residues in the emulsifier comprising from 22 to 24 carbon atoms is at least 60%, preferably at least 70%, at least 80%, at least 90%.
  • the non-hydrogenated emulsifier is an emulsifier obtainable or obtained by the method of the present invention.
  • the emulsifier has a melting point of at least 40 °C; preferably at least 45 0 C; at least 50 0 C; at least 55 0 C; at least 60 0 C; at least 65 0 C; at least 70 0 C; at least 75 0 C; at least 80 °C; at least 85 0 C; at least 90 0 C; at least 95 0 C; at least 100 0 C.
  • the foodstuff or food ingredient selected from a bakery product, bread improver, chocolate, chocolate spread, dairy product, fat based confectionary filling, fat based icing, frozen dairy product, low-fat spread, margarine, frying margarine peanut butter, salad dressing, shortening, tahina, soluble food or drink powders, vegetable ghee
  • the foodstuff or food ingredient is a bakery product
  • the non-hydrogenated emulsifier having substantially no trans carbon-carbon double bonds comprises (d) monoglycerides and/or (e) diglycerides; wherein the fatty acids are derived from a triglyceride having an iodine value of less than 9 and substantially no trans carbon-carbon double bonds.
  • the bakery product may be selected from cake, cream bakery product, and puff pastry bakery product.
  • the soluble food or drink powders is a wetting agent for powdered milk instantisation.
  • the foodstuff or food ingredient is a dairy product
  • the non-hydrogenated emulsifier having substantially no trans carbon-carbon double bonds comprises (d) monoglycerides and/or (e) diglycerides; wherein the fatty acids are derived from a triglyceride having an iodine value of less than 9 and substantially no trans carbon-carbon double bonds.
  • the foodstuff or food ingredient is a dairy product
  • the non-hydrogenated emulsifier having substantially no trans carbon-carbon double bonds comprises (f) carboxylic acid esters of monoglycerides and/or (g) carboxylic acid esters of diglycerides; wherein the carboxylic acid esters are lactic acid esters; wherein the fatty acids of the monoglycerides and/or diglycerides are derived from a triglyceride having an iodine value of less than 9 and substantially no trans carbon- carbon double bonds.
  • the dairy product is selected from ice cream and mousse. More preferably the dairy product is mousse.
  • the mousse may be a low-fat (2% fat or less) or a standard-fat mousse (5% fat or more). Most preferably, the dairy product is a low fat mousse.
  • the foodstuff or food ingredient is a low fat spread or a margarine
  • the non-hydrogenated emulsifier having substantially no trans carbon-carbon double bonds comprises (d) monoglycerides and/or (e) diglycerides; wherein the fatty acids are derived from a triglyceride having an iodine value of less than 9 and substantially no trans carbon-carbon double bonds.
  • the foodstuff or food ingredient is a topping powder
  • the non- hydrogenated emulsifier having substantially no trans carbon-carbon double bonds comprises (f) carboxylic acid esters of monoglycerides and/or (g) carboxylic acid esters of diglycerides; wherein the carboxylic acid esters are acetic acid esters; wherein the fatty acids of the monoglycerides and/or diglycerides are derived from a triglyceride having an iodine value of less than 9 and substantially no trans carbon- carbon double bonds.
  • the non-hydrogenated emulsifier (s) is (a) mono-fatty acid ester of a polyol compound.
  • the polyol compound is glycerol.
  • the non- hydrogenated emulsifier (s) is a monoglyceride.
  • the ratio of the palm stearine triglyceride (r) to the emulsifier (s) ranges from 30:70 to 70:30.
  • the ratio ranges from 40:60 to 60:40.
  • the ratio is about 50:50.
  • Emulsifier Composition More preferably the non-hydrogenated emulsifier (y) is (a) mono-fatty acid ester of a polyo! compound.
  • the polyol compound is glycerol.
  • the non- hydrogenated emulsifier (y) is a monoglyceride.
  • the ratio of the palm stearine monoglycerides and/or palm stearine diglycerides (x) to the non-hydrogenated emulsifier (y) ranges from 30:70 to 70:30.
  • the ratio ranges from 40:60 to 60:40.
  • the ratio is about 50:50.
  • the invention provides the use of a non-hydrogenated emulsifier having substantially no trans carbon-carbon double bonds comprising (d) monoglycerides and/or (e) diglycerides; wherein the fatty acids are derived from a triglyceride having an iodine value of less than 9 and substantially no trans carbon-carbon double bonds; in a bakery product.
  • the bakery product may be selected from a cake, a cream bakery product, and puff pastry bakery product.
  • the invention provides the use of a non-hydrogenated emulsifier having substantially no trans carbon-carbon double bonds comprising (d) monoglycerides and/or (e) diglycerides; wherein the fatty acids are derived from a triglyceride having an iodine value of less than 9 and substantially no trans carbon-carbon double bonds; in a low fat spread or a margarine.
  • the invention provides the use of a non-hydrogenated ⁇ emulsifier having substantially no trans carbon-carbon double bonds comprising (d) monoglycerides and/or (e) diglycerides; wherein the fatty acids are derived from a triglyceride having an iodine value of less than 9 and substantially no trans carbon-carbon double bonds; in a dairy product.
  • the dairy product is selected from ice cream and mousse.
  • the present invention provides the use of a non-hydrogenated emulsifier having substantially no trans carbon-carbon double bonds comprising (f) acid esters of monoglycerides and/or (g) acid esters of diglycerides; wherein the acid esters are lactic acid esters; wherein the fatty acids of the monoglycerides and/or diglycerides are derived from a triglyceride having an iodine value of less than 9 and substantially no trans carbon- carbon double bonds; in a dairy product.
  • the dairy product is selected from ice cream and mousse. More preferably the dairy product is mousse.
  • the mousse may be a low-fat (2% fat or less) or a standard-fat mousse (5% fat or more). Most preferably, the dairy product is a low fat mousse.
  • the present invention provides the use of a non-hydrogenated emulsifier having substantially no trans carbon-carbon double bonds comprising (f) acid esters of monoglycerides and/or (g) acid esters of diglycerides; wherein the acid esters are acetic acid esters; wherein the fatty acids of the monoglycerides and/or diglycerides are derived from a triglyceride having an iodine value of less than 9 and substantially no trans carbon- carbon double bonds; in a toping powder.
  • the triglyceride has an iodine value of less than 8, less than 7, less than 6, less than 5, less than 4, less than 3, less than 2.
  • the non-hydrogenated emulsifier has an iodine value of less than 8, less than 7, less than 6, less than 5, less than 4, less than 3, less than 2.
  • substantially no trans carbon-carbon double bonds means that the fatty acid residues comprise less that 5% trans; preferably less than 3% trans; preferably less than 2% trans; preferably less than 1 % trans; preferably less than 0.7% trans; preferably less than 0.5% trans; preferably less than 0.4% trans; preferably less than 0.3% trans; preferably less than 0.2% trans.
  • the trans content may be measured using Gas Chromatography.
  • a suitable method is American Oil Chemists' Society (AOCS) Method Ce 1f-96.
  • Figure 1 shows with the melting profiles for samples 1 to 4 as detailed in table 8;
  • Figure 2 shows cream density as a function of emulsifier and whipping time
  • Figure 3 shows cross sections of croissants, where the numbers correlates to the experimental no of table 22
  • Figure 4 shows cross sections of puff pastry, where the numbers correlates to the experimental no of table 22;
  • Figure 5 shows volume and cross section of puff pastry made with puff pastry margarine with DIMODAN NH 100 (1) and distilled monoglyceride based on Margo 8;
  • Figure 6 shows the rate of crystallisation results in the commercial filling fat AKOCREM M (also known as ACOCREAM).
  • Figure 7 shows the impact of different emulsifiers on rate of crystallisation in a fat blend consisting of 20% interesterified fat (PK4lnes) and rapeseed oil.
  • PK4lnes interesterified fat
  • rapeseed oil 20% interesterified fat
  • a triglyceride is melted, and glycerol compound (and optionally a catalyst, typically an alkaline catalyst) is charged to a reactor.
  • glycerol compound and optionally a catalyst, typically an alkaline catalyst
  • the proportion of monoglycerides in the mono-diglyceride mixture will depend on the proportions of triglyceride and glycerol used. Table 1 indicates suitable proportions of triglyceride and glycerol that may be used.
  • reaction mixture is neutralized with phosphoric acid.
  • a deodorisation setup is prepared and the reaction mixture is deodorized at 140 0 C, at ⁇ 0.5mmHg for 30 minutes.
  • reaction mixture is filtered through a diatomaceous filter earth to give a product mono-diglyceride.
  • Suitable diatomaceous filter earth include kieselguhr or celite.
  • the product mono-diglyceride is then distilled on a short path column in order to provide a distilled monoglyceride.
  • Example 1 The triglyceride Margo 8 was obtained from Premium Vegetable Oils, Malaysia.
  • the fatty acid content of this triglyceride is shown in Table 2, the triglyceride had a melting point of 61.1 0 C and an iodine value of 6.5 (see Table 3).
  • the triglyceride was reacted with glycerol in accordance with the general method to provide a distilled monoglyceride with the properties shown in Table 3.
  • the iodine value is a measure of the unsaturation of fats and oils, and is expressed in terms of the number of grams of iodine absorbed per 100 grams of the sample (% iodine absorbed).
  • the method is applicable to all animal fats, oils and products derived from these not containing conjugated systems.
  • potassium iodide 150 g of potassium iodide is dissolved and diluted to 1000 ml with deionised water (Reagents) 30% acetic acid: 300 ml of acetic acid is diluted to 1000 ml with deionised water
  • piston burette e.g. Metrohm equipment
  • piston burette 20 ml repeater pipette
  • the iodine value may be calculated as follows:
  • the temperature correction factor Ct is as shown in Table 4.
  • the saponification value may be determined using (AOCS) Method Cd 3-25. IUPAC sixth ed.
  • the acid value may be determined using Food Chemical Codex (FCC) method 2, p. 902, 2 nd edition.
  • FCC Food Chemical Codex
  • the colour number, red and yellow values may be determined using AOCS Cc 13e-92.
  • the melting point may be determined using AOCS Cc 3-25; FCC page 842-843; Ph. Nordica Vol. 1963, page 69.
  • Example 2 All emulsifiers are prepared according to European Food Emulsifiers and Manufacturers Association (EFEMA) guidelines.
  • EFEMA European Food Emulsifiers and Manufacturers Association
  • the acetem samples were prepared according to EFEMA guideline e472a and in accordance with industry standards.
  • a number of preparative methods are known and are discussed in "Emulsifiers in Food Technology” Edited by Robert J. Whitehurst (2004) Blackwell Publishing Ltd. Suitable methods include those disclosed in US RE28.737.
  • Acetem 38-00 is an Acetem compound based on fully hydrogenated palm oil prepared to provide a comparision.
  • Acetem 38-8 is an Acetem prepared from the Margo 8 starting material.
  • Acetem 38-15 is prepared from a fractionated palm stearine with an iodine value of 15.
  • Fractionated palm stearine with an iodine value of 15 is commercially available from a number of manufacturers including Loders Crooklaan B.V., The Netherlands; and Premium Vegetable Oils, Malaysia.
  • Acetem was tested in a topping powder formulation. The results are:
  • the gel strength of the jelly was tested using a Boucher Electronic Jelly Tester.
  • ACETEM 35-8 shows the best results, based on the jelly results.
  • EFEMA EFEMA Association
  • the viscosity was determined by measuring the outlet time from a GRINDSTED® standard pipette in seconds.
  • the melting rate of the ice cream(drip rate) was measured as follows:
  • Wire netting made of stainless steel wire (0.9mm thick) with square holes of 5.0mm
  • a rectangular piece of ice cream (125cc, dimension: approx. 100mm x 50mm x 25mm), which has been tempered to approx. -18°C for a minimum of 24 hours, is weighed and placed on wire netting.
  • the wire netting is placed above a 500ml glass beaker placed on an analytical balance.
  • the analytical balances are linked to a computer which registers the weight of the ice cream in the beaker every 2 minutes and calculates the percentage of melted ice cream as a function of time. After 120 minutes a graph of the melting behaviour can be plotted.
  • the time elapsed before the first drop of liquid is released from the product is also recorded.
  • the SEF was determination as follows:
  • the detected SEF values correlate well with the melting profiles (see Figure 1 ) - quicker melting samples of ice cream (sample 3 and 4) had smaller SEF value (see table below).
  • the melting rate of ice cream samples which contain experimental sample of mono- diglycerides (2 and 3) were slower than the melting rate of the samples containing CREMODAN® Mono-Di 60 Veg (1 and 4) (see Figure 1).
  • ice cream samples which are based on hydrogenated coconut oil (sample 2) and on anhydrous milk fat (sample 3) and contain experimental samples of mono-diglycerides, had a higher SEF value than the corresponding samples with commercial CREMODAN® Mono-Di 60Veg (samples 1 and 4).
  • the sensorial evaluation panel observed that ice cream samples containing experimental mono- diglycerides were slightly creamer and warmer when consumed than the corresponding samples prepared with commercial CREMODAN® Mono-Di 60 Veg.
  • the tested non-hydrogenated mono-diglycerides with an iodine value of 8 can be used in ice cream production. Surprisingly, the tested mono- diglycerides appear to be provide improved sensorial performance in comparison with the corresponding samples prepared with commercial CREMODAN® Mono-Di 60 Veg.
  • Example 4 All emulsifiers are prepared according to European Food Emulsifiers and Manufacturers Association (EFEMA) guidelines.
  • EFEMA European Food Emulsifiers and Manufacturers Association
  • the Lactem samples were prepared according to EFEMA guideline e472b and in accordance with industry standard. A number of preparative methods are known and are discussed in "Emulsifiers in Food Technology” Edited by Robert J. Whitehurst (2004) Blackwell Publishing Ltd.
  • a suitable preparative procedure is as follows:
  • Lactem P22 NH One non-hardened version is designated Lactem P22 NH (8) and is prepared from Margo 8.
  • the second non-hardened version is designated Lactem P22 NH (15) and is prepared from Fractionated palm stearine with an iodine value of 15.
  • Textural Analysis TA-XT 2 Plus texture analyzer was used with the following settings:
  • the first trials involved Lactem P22 NH (8) prepared from Margo 8. Subsequent trials also involved Lactem P22 (15) prepared from palm stearine
  • Samples for the mix were whipped on a Hobart mixer for measurements of overrun (OR). Those results are given in Table 13 below. Sample 1 is the reference with Lactem P22 as the whipping agent.
  • results in table 14 are a replication of the results found in table 13 plus additional trials with a non-hardened Lactem P22 with a higher iodine value, as well as samples with low dosage of emulsifier.
  • results in table 16 are a replication of the results found in table 16 plus additional trials with a non-hardened Lactem P22 with a higher iodine value, as well as samples with low dosage of emulsifier.
  • the non-hardened lactem surprisingly shows increased firmness, increased ability to be whipped (as shown by a higher overrun) and increased creaminess compared to standard P22.
  • the non-hydrogenated lactem P22 can be used as an alternative to standard P22, and in some applications (such as low fat mousse) provides increased functionality.
  • Margo 8 based emulsifiers in Oil &Fat applications In Oils & Fats a distilled monoglyceride and a citric acid ester based on Margo 8 have been tested in retail spread, cake and cream margarine, puff pastry margarine and in frying margarine to see how the choice of raw material influenced the application.
  • emulsifiers are prepared according to European Food Emulsifiers and Manufacturers Association (EFEMA) guidelines.
  • EFEMA European Food Emulsifiers and Manufacturers Association
  • the monoglycerides and mono- diglycerides were prepared according to EFEMA guideline e4721 and in accordance with industry standard.
  • the Citrems were prepared according to EFEMA guideline e472c and in accordance with industry standard.
  • a number of preparative methods are known and are discussed in "Emulsifiers in Food Technology” Edited by Robert J. Whitehurst (2004) Blackwell Publishing Ltd. Suitable methods include those disclosed in US 4,071 ,544.
  • Table 18 The margarine and spread samples were evaluated sensorial for mouth feel (with focus on creaminess) and meltdown and their ability to spread was evaluated by a standard spread test using a spreading knife and a piece of cardboard.
  • Emulsion Add the water phase to the fat phase while stirring
  • Figure 2 shows cream density as a function of emulsifier and whipping time
  • the distilled monoglyceride based on Margo 8 performs similar to DIMODAN NH 100 with a tendency of a foam collapse after 15 min of whipping.
  • DIMODAN HP gives creams with lighter density and with increased air incorporation compared to distilled monoglyceride based on Margo 8 and DIMODAN NH 100
  • the recipe can be found in table 22.
  • Figure 3 Cross sections of croissants. The numbers correlates to the experimental no of table 22.
  • Figure 4 Cross sections of puff pastry. The numbers correlates to the experimental no of table 22.
  • Table 24 Test of distilled monoglycerides on Margo 8 and DIMODAN NH 100 in puff pastry margarine Puff pastry was made of the two margarines - and this time no differences in volume were noted. This is illustrated in Figure 5.
  • Figure 5 Volume and cross section of puff pastry made with puff pastry margarine with DIMODAN NH 100 (1) and distilled monoglyceride based on Margo 8.
  • Citric acid esters are typically used in frying margarine to reduce the spattering generated by the frying process.
  • GRINDSTED® CITREM 2-IN-1 or GRINDSTED® CITREM SP 70 are recommended for the use in frying margarine.
  • Emulsion Add the water phase to the fat phase while stirring
  • a fixed amount of margarine is added to a preheated hot frying pan on a hot plate surrounded by brown paper.
  • the spattering is measured when the margarine is no longer spattering as the amount of fat stains on the brown paper, the numbers as stated below:
  • the samples were in this method fried four times in total over two 2 days.
  • Table 29 gives the average spattering values for the both solid and liquid margarine (along with the standard deviation).
  • the spattering is here defined as spattering created during the evaporation of the water phase of the margarine, also sometimes called the primary spattering, i.e. the spattering that takes place before food stuff is added to the pan.
  • CITREM 30-40 provides comparable performance to CITREM 2-IN-1 and CITREM SP 70 when fried using the open pan method. Using the refined method CITREM 30-40 performs better than SP 70 and on par with CITREM 2-IN-1.
  • CITREM 30-40 also gives better results when using the refined method compared to CITREMSP 70 and is on par or even better than CITREM 2-IN-1.
  • DIMODAN NH 100 is sometimes known as GRINDSTED® CRYSTALLIZER NH 105 and is commercially available from Danisco A/S.
  • AKOCREM M also known as ACOCREAM
  • ACOCREAM is commercially available from AAK Aarhus Karlshamn.
  • AKOCREM M the following emulsifiers were tested: - 1 % GRINDSTED® CRYSTALLIZER 100
  • the tests were conducted by melting the fat to 85 0 C and then adding the emulsifier. When the emulsifier was properly melted the fat/em ulsifier blend was measured into NMR tubes and allowed to solidify. Prior to the analysis the NMR tubes were placed at 85°C to ensure complete neutralisation of the crystal history by the complete melting of the fat/emulsifier blend for at least one hour.
  • Figure 6 shows the rate of crystallisation results in the commercial filling fat AKOCREM M.
  • the distilled monoglyceride is situated between DIMODAN NH 100 and DIMODAN HP and the differences between DIMODAN HP and the distilled monoglyceride based on Margo 8 is bigger.
  • Figure 7 shows the impact of different emulsifiers on rate of crystallisation in a fat blend consisting of 20% interesterified fat (PK4lnes) and rapeseed oil.
  • PK4lnes interesterified fat
  • rapeseed oil 20% interesterified fat
  • Distilled monoglyceride based on Margo 8 appears to provide similar crystallisation promotion results to DIMODAN HP, especially at the higher dosage of 1.5%. It provides better crystallisation promotion results than DIMODAN NH 100.

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  • Chemical & Material Sciences (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
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Abstract

La présente invention concerne un procédé de préparation d'un émulsifiant non hydrogéné ne comportant pratiquement aucune double liaison carbone-carbone trans, comprenant : (i) une étape d'interestérification comprenant un composé polyol et un triglycéride non hydrogéné, ledit triglycéride ayant un indice d'iode inférieur à 9 et pratiquement aucune double liaison carbone-carbone trans. La présente invention concerne également un émulsifiant non hydrogéné ne comportant pratiquement aucune double liaison carbone-carbone trans, ainsi que des produits alimentaires et des compositions contenant un tel émulsifiant et les utilisations d'un tel émulsifiant.
PCT/GB2007/004315 2006-11-13 2007-11-13 Procédé de préparation d'émulsifiants non hydrogénés Ceased WO2008059220A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012168726A1 (fr) * 2011-06-09 2012-12-13 Dupont Nutrition Biosciences Aps Pâte à tartiner pauvre en graisses
US8859230B2 (en) 2007-11-21 2014-10-14 Roskilde Universitet Polypeptides comprising an ice-binding activity
EP3639672A1 (fr) * 2015-01-22 2020-04-22 FrieslandCampina Nederland B.V. Agent moussant destiné à être utilisé dans la préparation de garnitures comestibles et procédé de préparation dudit agent
US20210106961A1 (en) * 2017-05-08 2021-04-15 Bunge Loders Croklaan B.V. Emulsifiers

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB785933A (en) * 1954-05-04 1957-11-06 Edelfettwerke G M B H Process for the preparation of fatty acid esters suitable for use as ointment bases and the like carrier media
US3515562A (en) * 1967-05-05 1970-06-02 Top Scor Products Frozen coneections containing glycerol and propylene glycol monoesters of isostearic acid
GB1252224A (fr) * 1970-01-22 1971-11-03
GB2001072A (en) * 1977-07-16 1979-01-24 Goldschmidt Ag Th Process for the manufacture of mixed esters from hydroxy. acids and partial fatty acid glycerides
EP0023062A1 (fr) * 1979-07-18 1981-01-28 THE PROCTER & GAMBLE COMPANY Composition de graisse pour beurre dur, sa préparation et son utilisation dans la fabrication du chocolat
EP0203831A1 (fr) * 1985-05-31 1986-12-03 Nexus A/S Emulsionnant et son procédé de préparation
US6217874B1 (en) * 1991-03-15 2001-04-17 Aarhus Oliefabrik A/S Fat compositions and their use in cosmetic and pharmaceutical emulsion products

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB785933A (en) * 1954-05-04 1957-11-06 Edelfettwerke G M B H Process for the preparation of fatty acid esters suitable for use as ointment bases and the like carrier media
US3515562A (en) * 1967-05-05 1970-06-02 Top Scor Products Frozen coneections containing glycerol and propylene glycol monoesters of isostearic acid
GB1252224A (fr) * 1970-01-22 1971-11-03
GB2001072A (en) * 1977-07-16 1979-01-24 Goldschmidt Ag Th Process for the manufacture of mixed esters from hydroxy. acids and partial fatty acid glycerides
EP0023062A1 (fr) * 1979-07-18 1981-01-28 THE PROCTER & GAMBLE COMPANY Composition de graisse pour beurre dur, sa préparation et son utilisation dans la fabrication du chocolat
EP0203831A1 (fr) * 1985-05-31 1986-12-03 Nexus A/S Emulsionnant et son procédé de préparation
US6217874B1 (en) * 1991-03-15 2001-04-17 Aarhus Oliefabrik A/S Fat compositions and their use in cosmetic and pharmaceutical emulsion products

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8859230B2 (en) 2007-11-21 2014-10-14 Roskilde Universitet Polypeptides comprising an ice-binding activity
US9241511B2 (en) 2007-11-21 2016-01-26 Roskilde Universitet Polypeptides comprising an ice-binding activity
US10266576B2 (en) 2007-11-21 2019-04-23 Roskilde Universitet Polypeptides comprising an ice-binding activity
WO2012168726A1 (fr) * 2011-06-09 2012-12-13 Dupont Nutrition Biosciences Aps Pâte à tartiner pauvre en graisses
CN103596443A (zh) * 2011-06-09 2014-02-19 杜邦营养生物科学有限公司 低脂肪涂抹酱
EP3639672A1 (fr) * 2015-01-22 2020-04-22 FrieslandCampina Nederland B.V. Agent moussant destiné à être utilisé dans la préparation de garnitures comestibles et procédé de préparation dudit agent
US20210106961A1 (en) * 2017-05-08 2021-04-15 Bunge Loders Croklaan B.V. Emulsifiers
US12129420B2 (en) * 2017-05-08 2024-10-29 Bunge Loders Croklaan B.V. Emulsifiers

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