EP0289968A1 - Use of a fatty oil ex Helianthus annuus for the production of fatty acid monoglycerides - Google Patents
Use of a fatty oil ex Helianthus annuus for the production of fatty acid monoglycerides Download PDFInfo
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- EP0289968A1 EP0289968A1 EP88106971A EP88106971A EP0289968A1 EP 0289968 A1 EP0289968 A1 EP 0289968A1 EP 88106971 A EP88106971 A EP 88106971A EP 88106971 A EP88106971 A EP 88106971A EP 0289968 A1 EP0289968 A1 EP 0289968A1
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- fatty
- acid
- fatty acid
- glycerol
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- 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
- C11C3/06—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with glycerol
-
- 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
Definitions
- Glycerol mono- and distearate (GMS) and GMO glycerol mono- and dioleate
- GMS is produced by glycerolysis of glycerol tristearate or of hardened fats, which contain at least 55% stearic acid, in continuous or discontinuous processes, since the starting material is easily accessible by hardening fats and oils.
- GMO is usually produced by the esterification of oleic acid with glycerin, since the glycerol trioleate required for glycerolysis can only be produced technically in several stages.
- the oleic acid used for the esterification with glycerol is obtained by enrichment (solvent or cross-linking process) of the oleic acid contained in tallow fatty acid.
- enrichment solvent or cross-linking process
- Fatty acid monoglycerides are mainly used in food technology as emulsifiers. They should therefore have the greatest possible resistance to oxidation, which is reduced by contents of polyunsaturated fatty acids, in particular linoleic acid.
- fatty oils with the composition described at the outset from certain sunflowers (Helianthus annuus) species such as, for. B. are known from US Pat. No. 4,627,192, without using the preparation processes customary in the prior art for the production of fatty acid monoglycerides by transesterification known per se in the presence of glycerol or fat cleavage and reaction of the split fatty acid obtained with glycerol.
- fatty acid monoglycerides based on these fatty oils have improved application properties.
- the oxidative resistance is significantly greater than that of conventional fatty acid monoglycerides. This is surprising since the content of polyunsaturated fatty acids in the fatty acid monoglycerides obtained according to the invention is comparable to that in those obtained from tallow fatty acid. Furthermore, the fatty acid monoglycerides obtained according to the invention have improved emulsifier properties compared to those from the prior art.
- the fatty oils used as starting materials are natural substances, the proportions of their main components are subject to certain fluctuations.
- the fatty oils or the fatty acid monoglycerides obtained therefrom according to the invention typically have the following fluctuation ranges with regard to the fatty acids: Oleic acid: 78 to 92% by weight Linoleic acid: 2 to 10% by weight Palmitic acid: 2 to 5% by weight Stearic acid: 2 to 7% by weight
- the glycerol monooleates produced according to the invention using the above-mentioned fatty oils have monoester contents of 40 to 60%, which can be obtained in the usual way, e.g. B. by Molecular distillation, increase to a monoester content of 90% and above.
- the GMO produced using fatty oils of the abovementioned composition according to the invention was tested in the Rancimat against a GMO produced from fractional oleic acid according to the classic method with regard to its oxidation stability.
- the Rancimat (from Metrohm) is an analytical device widely used in the food industry for testing the oxidation stability of unsaturated oils.
- a constant air flow is conducted through a defined amount of sample at an elevated temperature (100 to 120 ° C); the volatile compounds formed during the oxidation are determined in a condensation vessel on the basis of their electrical conductivity.
- the time until volatile, electrically conductive oxidation products are formed is called the induction time.
- smell and taste were rated on a 10-point scale. 10 points mean a tasteless and odorless, 1 point a completely unusable product.
- oils should have a score of at least 6. The color was measured in the Lovibond colorimeter with a 5 1 / 4 ⁇ cell.
- the following comparative example demonstrates the excellent suitability of the monoglycerides obtained using fatty oils according to the above composition for the preparation of the emulsion: 0.5 part by weight of emulsifier from tallow fatty acid and according to the invention were dissolved at 40 ° C. in 35 parts by weight of soybean oil. 64.5 parts by weight of water were then added while stirring in a slow stream. Finally, the pre-emulsion was finely homogenized twice in a high-pressure homogenizer at 120 bar.
- the glycerol monooleate according to the invention has superior emulsifier properties over that according to the prior art.
- the sunflower oil had the following composition of the fatty acid components: Myristic acid 0.1% by weight Palmitic acid 3.1% by weight Stearic acid 2.0% by weight Oleic acid 86.2% by weight Linoleic acid 7.8% by weight Linolenic acid 0.2% by weight Arachic acid 0.2% by weight Eicosenoic acid 0.2% by weight Erucic acid 0.2% by weight
- An oleic acid monoglyceride was obtained with the following characteristics: Acid number 1.3 Saponification number 163 Iodine number 74 OH number 239 Glycerol content: 0.6% by weight Monoglyceride content: 60% by weight.
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- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Edible Oils And Fats (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
Description
Die Erfindung betrifft die Verwendung eines fetten Öles ex Helianthus annuus mit einem Ölsäuregehalt von 78 bis 92 Gew.-% und einem Linolsäuregehalt von 2 bis 8 Gew.-%, jeweils bezogen auf enthaltende Gesamtfettsäuren, Rest (auf 100 Gew.-%) gegebenenfalls Palmitinsäure und Stearinsäure sowie bis zu 1 Gew.-% Fettsäuren aus der von Myristin-, Palmitolein-, Linolen-, Arachin-, Eikosen- und Erucasäure gebildeten Gruppe unter Auschluß von Anreicherungsschritten bezüglich des Ölsäuregehaltes zur Herstellung von Fettsäure-Monoglyceriden durch
- a) Umesterung in Gegenwart von Glycerin oder
- b) durch Fettspaltung und Umsetzung der erhaltenen Spaltfettsäure mit Glycerin.
- a) transesterification in the presence of glycerol or
- b) by fat cleavage and reaction of the split fatty acid obtained with glycerol.
Es ist bekannt, durch Umesterung von fetten Ölen mit Glycerin in Gegenwart von Katalysatoren Monoglyceride und Diglyceride herzustellen. Die größte wirtschaftliche Bedeutung haben dabei Glycerinmono- und -distearat (GMS) und Glycerinmono- und -dioleat (GMO).It is known to produce monoglycerides and diglycerides by transesterifying fatty oils with glycerol in the presence of catalysts. Of greatest economic importance Glycerol mono- and distearate (GMS) and glycerol mono- and dioleate (GMO).
GMS wird durch Glycerinolyse von Glycerin-tristearat bzw. von gehärteten Fetten, die mindestens 55 % Stearinsäure enthalten, in kontinuierlichen oder diskontinuierlichen Verfahren hergestellt, da das Ausgangsmaterial durch Härtung von Fetten und Ölen leicht zugänglich ist. GMO dagegen wird üblicherweise durch Veresterung von Ölsäure mit Glycerin hergestellt, da das für die Glycerinolyse erforderliche Glycerin-trioleat technisch nur über mehrere Stufen herstellbar ist.GMS is produced by glycerolysis of glycerol tristearate or of hardened fats, which contain at least 55% stearic acid, in continuous or discontinuous processes, since the starting material is easily accessible by hardening fats and oils. GMO, on the other hand, is usually produced by the esterification of oleic acid with glycerin, since the glycerol trioleate required for glycerolysis can only be produced technically in several stages.
Die zur Veresterung mit Glycerin verwendete Ölsäure wird durch Anreicherung (Lösemittel- oder Umnetzverfahren) der in Talgspaltfettsäure enthaltenen Ölsäure gewonnen. Diesen Anreicherungsverfahren sind allerdings prinzipielle Grenzen gesetzt. Technisch kommen daher lediglich 65 bis 70 %-ige Ölsäuren für die GMO-Herstellung zum Einsatz.The oleic acid used for the esterification with glycerol is obtained by enrichment (solvent or cross-linking process) of the oleic acid contained in tallow fatty acid. However, there are basic limits to these enrichment processes. Technically, therefore, only 65 to 70% oleic acids are used for GMO production.
Fettsäure-Monoglyceride werden hauptsächlich in der Nahrungsmitteltechnik als Emulgatoren eingesetzt. Sie sollen daher eine möglichst große Oxidationsbeständigkeit aufweisen, die durch Gehalte an mehrfach ungesättigten Fettsäuren, insbesondere Linolsäure, herabgesetzt ist.Fatty acid monoglycerides are mainly used in food technology as emulsifiers. They should therefore have the greatest possible resistance to oxidation, which is reduced by contents of polyunsaturated fatty acids, in particular linoleic acid.
Es wurde nun gefunden, daß fette Öle mit der eingangs beschriebenen Zusammensetzung aus bestimmten Sonnenblumen (Helianthus annuus)-Arten, wie sie z. B. aus der US-PS 4 627 192 bekannt sind, ohne die nach dem Stand der Technik üblichen Aufbereitungsverfahren für die Herstellung von Fettsäure-Monoglyceriden durch an sich bekannte Umesterung in Gegenwart von Glycerin oder Fettspaltung und Umsetzung der erhaltenen Spaltfettsäure mit Glycerin einsetzen lassen.It has now been found that fatty oils with the composition described at the outset from certain sunflowers (Helianthus annuus) species, such as, for. B. are known from US Pat. No. 4,627,192, without using the preparation processes customary in the prior art for the production of fatty acid monoglycerides by transesterification known per se in the presence of glycerol or fat cleavage and reaction of the split fatty acid obtained with glycerol.
Überraschenderweise hat sich herausgestellt, daß Fettsäure-Monoglyceride auf Basis dieser fetten Öle verbesserte anwendungstechnische Eigenschaften zeigen. So ist die oxidative Beständigkeit im Vergleich zu üblichen Fettsäure-Monoglyceriden deutlich größer. Dies ist insofern überraschend, da der Gehalt an mehrfach ungesättigten Fettsäuren in den erfindungsgemäß erhaltenen Fettsäure-Monoglyceriden vergleichbar hoch wie bei denjenigen aus Talgspaltfettsäure gewonnenen ist. Weiterhin weisen die erfindungsgemäß erhaltenen Fettsäure-Monoglyceride gegenüber denjenigen aus dem Stand der Technik verbesserte Emulgatoreigenschaften auf. Schließlich ist es als überraschend anzusehen, daß sich bei Verwendung von fetten Ölen der eingangs genannten Art Fettsäure-Monoglyceride erhalten lassen, die Oxidationsbeständigkeit, Geruchs-, Geschmacks- und Farbneutralität sowie gute Emulgiereigenschaften aufweisen, ohne daß die als Ausgangsmaterialien verwendeten fetten Öle vor der Umsetzung irgendwelchen Anreicherungsschritten unterzogen werden müssen.Surprisingly, it has been found that fatty acid monoglycerides based on these fatty oils have improved application properties. The oxidative resistance is significantly greater than that of conventional fatty acid monoglycerides. This is surprising since the content of polyunsaturated fatty acids in the fatty acid monoglycerides obtained according to the invention is comparable to that in those obtained from tallow fatty acid. Furthermore, the fatty acid monoglycerides obtained according to the invention have improved emulsifier properties compared to those from the prior art. Finally, it is surprising that when using fatty oils of the type mentioned, fatty acid monoglycerides can be obtained which have resistance to oxidation, odor, taste and color neutrality and good emulsifying properties without the fatty oils used as starting materials before the reaction must undergo any enrichment steps.
Da die als Ausgangsmaterialien verwendeten fetten Öle Naturstoffe sind, sind die Anteile ihrer Hauptkomponenten gewissen Schwankungen unterworfen. Typischerweise weisen die fetten Öle bzw. die daraus erfindungsgemäß erhaltenen Fettsäure-Monoglyceride hinsichtlich der Fettsäuren die folgenden Schwankungsbreiten auf:
Ölsäure: 78 bis 92 Gew.-%
Linolsäure: 2 bis 10 Gew.-%
Palmitinsäure: 2 bis 5 Gew.-%
Stearinsäure: 2 bis 7 Gew.-%Since the fatty oils used as starting materials are natural substances, the proportions of their main components are subject to certain fluctuations. The fatty oils or the fatty acid monoglycerides obtained therefrom according to the invention typically have the following fluctuation ranges with regard to the fatty acids:
Oleic acid: 78 to 92% by weight
Linoleic acid: 2 to 10% by weight
Palmitic acid: 2 to 5% by weight
Stearic acid: 2 to 7% by weight
Die erfindungsgemäß unter Verwendung der obengenannten fetten Öle hergestellten Glycerinmonooleate weisen Monoestergehalte von 40 bis 60 % auf, die sich auf üblichem Wege, z. B. durch Molekulardestillation, auf einen Monoestergehalt von 90 % und darüber steigern lassen.The glycerol monooleates produced according to the invention using the above-mentioned fatty oils have monoester contents of 40 to 60%, which can be obtained in the usual way, e.g. B. by Molecular distillation, increase to a monoester content of 90% and above.
Das unter der erfindungsgemäßen Verwendung von fetten Ölen der obengenannten Zusammensetzung hergestellte GMO wurde im Rancimaten gegen einen aus fraktionierter Ölsäure nach dem klassischen Verfahren hergestelltes GMO hinsichtlich seiner Oxidationsstabilität geprüft. Der Rancimat (Fa. Metrohm) ist ein in der Nahrungsmittelindustrie weit verbreitetes Analysengerät zur Prüfung der Oxidationsstabilität ungesättigter Öle.The GMO produced using fatty oils of the abovementioned composition according to the invention was tested in the Rancimat against a GMO produced from fractional oleic acid according to the classic method with regard to its oxidation stability. The Rancimat (from Metrohm) is an analytical device widely used in the food industry for testing the oxidation stability of unsaturated oils.
Bei der Analyse wird bei erhöhter Temperatur (100 bis 120°C) durch eine definierte Probenmenge ein konstanter Luftstrom geleitet; die bei der Oxidation entstehenden flüchtigen Verbindungen werden in einem Kondensationsgefäß anhand der elektrischen Leitfähigkeit derselben bestimmt. Die Zeit bis zur Bildung von flüchtigen, elektrisch leitenden Oxidationsprodukten wird als Induktionszeit bezeichnet.During the analysis, a constant air flow is conducted through a defined amount of sample at an elevated temperature (100 to 120 ° C); the volatile compounds formed during the oxidation are determined in a condensation vessel on the basis of their electrical conductivity. The time until volatile, electrically conductive oxidation products are formed is called the induction time.
Für das erfindungsgemäß hergestellte GMO wurde eine Induktionszeit von 4 h, für das aus Talgspaltfettsäure gewonnene eine solche von 2 h gemessen.An induction time of 4 h was measured for the GMO produced according to the invention and a time of 2 h for that obtained from tallow fatty acid.
Zusätzlich wurden Geruch und Geschmack nach einer 10-Punkte-Skala bewertet. 10 Punkte bedeuten ein geschmacks- und geruchsneutrales, 1 Punkt ein völlig unbrauchbares Produkt. Zur Verwendung in der Nahrungsmittelindustrie sollten Öle mindestens eine Punktzahl von 6 aufweisen. Die Farbe wurde im Lovibond-Farbmeßgerät mit einer 5 1/4˝-Küvette gemessen.In addition, smell and taste were rated on a 10-point scale. 10 points mean a tasteless and odorless, 1 point a completely unusable product. For use in the food industry, oils should have a score of at least 6. The color was measured in the Lovibond colorimeter with a 5 1 / 4˝ cell.
Die erhaltenen Ergebnisse sind in der folgenden Tabelle 1 zusammengefaßt.
Für das erfindungsgemäß erhaltene GMO ergeben sich deutliche sensorische und, wenn auch etwas schwächer ausgeprägt, farbliche Vorteile.For the GMO obtained according to the invention, there are clear sensory and, if somewhat less pronounced, color advantages.
Für die erfindungsgemäß beschriebenen Fettsäure-Monoglyceride ergeben sich entscheidende anwendungstechnische Vorteile, da die Möglichkeiten der GMO-Verwendung zur Herstellung von Emulsionen, beispielsweise von Speisefettemulsionen als Kälber milch-Ersatz (Milchaustauscher) oder von hoch wasserhaltigen Margarinen oder anderen fetthaltigen Brotaufstrichen ("low calorie spread") sowie von technisch anzuwendenden Emulsionen (z. B. für Brotschneidemaschinen) durch zu geringe Oxidationsstabilität bzw. sensorische Beeinträchtigungen bisher stark eingeschränkt gewesen sind.For the fatty acid monoglycerides described according to the invention, there are decisive advantages in terms of application, since the possibilities of GMO use for the production of emulsions, for example edible fat emulsions as calves Milk substitutes (milk replacers) or of high-water margarines or other fat-containing spreads ("low calorie spread") as well as technically applicable emulsions (e.g. for bread slicers) have been severely restricted due to insufficient oxidation stability or sensory impairments.
Das folgende Vergleichsbeispiel demonstriert die vorzügliche Eignung der unter Verwendung von fetten Ölen gemäß der obigen Zusammensetzung erhaltenen Monoglyceride für die Emulsionsherstellung:
0,5 Gew.-Teile Emulgator aus Talgspaltfettsäure und gemäß der Erfindung wurden bei 40°C in jeweils 35 Gew.-Teilen Sojaöl gelöst. Anschließend wurde unter Rühren in langsamem Strahl 64,5 Gew.-Teile Wasser hinzugegeben. Schließlich wurde die Voremulsion in einem Hochdruckhomogenisator 2 x bei 120 bar feinhomogenisiert.The following comparative example demonstrates the excellent suitability of the monoglycerides obtained using fatty oils according to the above composition for the preparation of the emulsion:
0.5 part by weight of emulsifier from tallow fatty acid and according to the invention were dissolved at 40 ° C. in 35 parts by weight of soybean oil. 64.5 parts by weight of water were then added while stirring in a slow stream. Finally, the pre-emulsion was finely homogenized twice in a high-pressure homogenizer at 120 bar.
Die Stabilität der erhaltenen Emulsionen wurde nach Stehenlassen von jeweils 100 ml frisch hergestellter Emulsion im graduierten Zylinder nach 24 h und nach 8 Tagen durch visuelle Beurteilung bzw. durch Extraktion von 25 ml-Schichten mit Petrolether bestimmt, wobei die 25 ml-Schichten jeweils von unten entnommen und mit Petrolether ausgeschüttelt wurden. Die organischen Phasen wurden abgetrennt, der Petrolether verdampft und der Rückstand (= Fettgehalt) gewogen.The stability of the emulsions obtained was determined after each time 100 ml of freshly prepared emulsion had been left to stand in the graduated cylinder after 24 h and after 8 days by visual assessment or by extraction of 25 ml layers with petroleum ether, the 25 ml layers each from below were removed and shaken with petroleum ether. The organic phases were separated, the petroleum ether evaporated and the residue (= fat content) weighed.
Die Ergebnisse sind in der folgenden Tabelle 2 zusammengefaßt.
Wie sich aus der Tabelle 2 ergibt, weist das Glycerinmonooleat gemäß der Erfindung überlegene Emulgatoreigenschaften gegenüber demjenigen gemäß Stand der Technik auf.As can be seen from Table 2, the glycerol monooleate according to the invention has superior emulsifier properties over that according to the prior art.
Die Herstellung eines Glycerinmonooleats under erfindungsgemäßer Verwendung eines fetten Öles wird im folgenden anhand eines bevorzugten Ausführungsbeispiels näher erläutert.The production of a glycerol monooleate using a fatty oil according to the invention is explained in more detail below with the aid of a preferred exemplary embodiment.
Das Sonnenblumenöl wies gemäß gaschromatografischer Auswertung die folgende Zusammensetzung der Fettsäureanteile auf:
Myristinsäure 0,1 Gew.-%
Palmitinsäure 3,1 Gew.-%
Stearinsäure 2,0 Gew.-%
Ölsäure 86,2 Gew.-%
Linolsäure 7,8 Gew.-%
Linolensäure 0,2 Gew.-%
Arachinsäure 0,2 Gew.-%
Eikosensäure 0,2 Gew.-%
Erucasäure 0,2 Gew/-%According to gas chromatographic analysis, the sunflower oil had the following composition of the fatty acid components:
Myristic acid 0.1% by weight
Palmitic acid 3.1% by weight
Stearic acid 2.0% by weight
Oleic acid 86.2% by weight
Linoleic acid 7.8% by weight
Linolenic acid 0.2% by weight
Arachic acid 0.2% by weight
Eicosenoic acid 0.2% by weight
Erucic acid 0.2% by weight
688 g Sonnenblumenöl der obigen Zusammensetzung wurden mit 290 g 99,5 %-igem Glycerin in einen 2 l-Dreihalskolben mit Rührer, Thermometer, Destillationsaufsatz und externer Heizung vorgelegt und unter Stickstoff auf 265°C erhitzt. Nach dem Erreichen dieser Temperatur werden 0,05 Vol.-% 50 %-ige Natronlauge zugesetzt. Die Reaktion war nach 5 bis 10 min beendet (Klarwerden des Kolbeninhaltes). Das Reaktionsprodukt wurde abgekühlt, bei 200°C mit Phosphorsäure neutralisiert und bei 100°C ca. 10 min stehengelassen. Das überschüssige Glycerin wurde abgezogen; anschließend wurde 3 x mit ca. 200 ml heißer gesättigter NaCl-Lösung bei 95°C gewaschen. Nach dem Trocknen bei 90 bis 100°C in Wasserstrahlvakuum wurde unter Zusatz von 1 % Filterhilfsmittel filtriert.688 g of sunflower oil of the above composition were placed with 290 g of 99.5% glycerol in a 2 l three-necked flask equipped with a stirrer, thermometer, distillation attachment and external heating and heated to 265 ° C. under nitrogen. After this temperature has been reached, 0.05% by volume of 50% sodium hydroxide solution are added. The reaction was complete after 5 to 10 minutes (the contents of the flask became clear). The reaction product was cooled, neutralized at 200 ° C with phosphoric acid and left at 100 ° C for about 10 minutes. The excess glycerin was removed; it was then washed 3 times with about 200 ml of hot saturated NaCl solution at 95 ° C. After drying at 90 to 100 ° C in a water jet vacuum was filtered with the addition of 1% filter aid.
Man erhielt ein Ölsäure-Monoglycerid mit folgenden Kenndaten:
Säurezahl 1,3
Verseifungszahl 163
Jodzahl 74
OH-Zahl 239
Glyceringehalt: 0,6 Gew.-%
Monoglyceridgehalt: 60 Gew.-%.An oleic acid monoglyceride was obtained with the following characteristics:
Acid number 1.3
Saponification number 163
Iodine number 74
OH number 239
Glycerol content: 0.6% by weight
Monoglyceride content: 60% by weight.
Claims (1)
a) Umesterung in Gegenwart von Glycerin oder
b) durch Fettspaltung und Umsetzung der erhaltenen Spaltfettsäure mit Glycerin.Use of a fatty oil ex Helianthus annuus with an oleic acid content of 78-92 wt .-% and a linoleic acid content of 2-8 wt .-%, each based on total fatty acids, the rest (to 100 wt .-%) optionally palmitic acid and stearic acid and up to 1% by weight of fatty acids from the group formed by myristic, palmitoleic, linolenic, arachinic, eicotene and erucic acid with the exclusion of enrichment steps with regard to the oleic acid content for the production of fatty acid monoglycerides
a) transesterification in the presence of glycerol or
b) by fat cleavage and reaction of the split fatty acid obtained with glycerol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT88106971T ATE62016T1 (en) | 1987-05-08 | 1988-04-30 | USE OF A FAT OIL EX HELIANTHUS ANNUUS IN THE PRODUCTION OF FATTY ACID MONOGLYCERIDES. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3715424 | 1987-05-08 | ||
| DE3715424A DE3715424C2 (en) | 1987-05-08 | 1987-05-08 | Use of a fatty oil from Helianthus annuus for the production of fatty acid monoglycerides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0289968A1 true EP0289968A1 (en) | 1988-11-09 |
| EP0289968B1 EP0289968B1 (en) | 1991-03-27 |
Family
ID=6327129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP88106971A Expired - Lifetime EP0289968B1 (en) | 1987-05-08 | 1988-04-30 | Use of a fatty oil ex helianthus annuus for the production of fatty acid monoglycerides |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0289968B1 (en) |
| JP (1) | JPS63287749A (en) |
| AT (1) | ATE62016T1 (en) |
| CA (1) | CA1313381C (en) |
| DE (2) | DE3715424C2 (en) |
| ES (1) | ES2021786B3 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994010003A1 (en) * | 1992-10-28 | 1994-05-11 | Daimler-Benz Aktiengesellschaft | Arrangement for the inductive transfer of energy to movable consumers |
| WO1996005740A1 (en) * | 1994-08-19 | 1996-02-29 | Croda International Plc | Nervonic acid compositions |
| EP0826765A1 (en) * | 1996-08-27 | 1998-03-04 | Institut Francais Du Petrole | Compositions of additives improving the lubricating capacity of motor fuels and motor fuels containing the same |
| US5844132A (en) * | 1996-06-24 | 1998-12-01 | Institute Francais Du Petrole | Method and system for real-time estimation of at least one parameter linked with the behavior of a downhole tool |
| WO2017085737A1 (en) * | 2015-11-19 | 2017-05-26 | Fine Research & Development Centre Pvt Ltd | A natural based monoglyceride with improved odor and flavor |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2789119A (en) * | 1954-02-09 | 1957-04-16 | Boake Roberts & Co Ltd | Production of fatty acid monoglycerides |
| DE1099520B (en) * | 1957-01-04 | 1961-02-16 | E F Drew & Co Inc | Process for the production of monoglycerides of fatty acids with 8 to 22 carbon atoms |
| US2976251A (en) * | 1957-04-19 | 1961-03-21 | Eastman Kodak Co | Glycerol fatty acid partial ester gels |
| US4627192A (en) * | 1984-11-16 | 1986-12-09 | Sigco Research Inc. | Sunflower products and methods for their production |
-
1987
- 1987-05-08 DE DE3715424A patent/DE3715424C2/en not_active Expired - Fee Related
-
1988
- 1988-04-30 DE DE8888106971T patent/DE3862147D1/en not_active Revoked
- 1988-04-30 ES ES88106971T patent/ES2021786B3/en not_active Expired - Lifetime
- 1988-04-30 EP EP88106971A patent/EP0289968B1/en not_active Expired - Lifetime
- 1988-04-30 AT AT88106971T patent/ATE62016T1/en not_active IP Right Cessation
- 1988-05-09 CA CA000566299A patent/CA1313381C/en not_active Expired - Fee Related
- 1988-05-09 JP JP63113412A patent/JPS63287749A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2789119A (en) * | 1954-02-09 | 1957-04-16 | Boake Roberts & Co Ltd | Production of fatty acid monoglycerides |
| DE1099520B (en) * | 1957-01-04 | 1961-02-16 | E F Drew & Co Inc | Process for the production of monoglycerides of fatty acids with 8 to 22 carbon atoms |
| US2976251A (en) * | 1957-04-19 | 1961-03-21 | Eastman Kodak Co | Glycerol fatty acid partial ester gels |
| US4627192A (en) * | 1984-11-16 | 1986-12-09 | Sigco Research Inc. | Sunflower products and methods for their production |
| US4627192B1 (en) * | 1984-11-16 | 1995-10-17 | Sigco Res Inc | Sunflower products and methods for their production |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994010003A1 (en) * | 1992-10-28 | 1994-05-11 | Daimler-Benz Aktiengesellschaft | Arrangement for the inductive transfer of energy to movable consumers |
| WO1996005740A1 (en) * | 1994-08-19 | 1996-02-29 | Croda International Plc | Nervonic acid compositions |
| US5994404A (en) * | 1994-08-19 | 1999-11-30 | Croda International Plc | Nervonic acid compositions |
| US5844132A (en) * | 1996-06-24 | 1998-12-01 | Institute Francais Du Petrole | Method and system for real-time estimation of at least one parameter linked with the behavior of a downhole tool |
| EP0826765A1 (en) * | 1996-08-27 | 1998-03-04 | Institut Francais Du Petrole | Compositions of additives improving the lubricating capacity of motor fuels and motor fuels containing the same |
| FR2752850A1 (en) * | 1996-08-27 | 1998-03-06 | Inst Francais Du Petrole | COMPOSITIONS OF ADDITIVES IMPROVING THE LUBRICATING POWER OF FUELS AND FUELS CONTAINING THEM |
| WO2017085737A1 (en) * | 2015-11-19 | 2017-05-26 | Fine Research & Development Centre Pvt Ltd | A natural based monoglyceride with improved odor and flavor |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3862147D1 (en) | 1991-05-02 |
| JPS63287749A (en) | 1988-11-24 |
| DE3715424A1 (en) | 1988-11-17 |
| CA1313381C (en) | 1993-02-02 |
| ATE62016T1 (en) | 1991-04-15 |
| ES2021786B3 (en) | 1991-11-16 |
| DE3715424C2 (en) | 1995-01-26 |
| EP0289968B1 (en) | 1991-03-27 |
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