EP0289968B1 - Utilisation d'une huile ex Helianthus annuus pour la production de monoglycérides d'acides gras - Google Patents

Utilisation d'une huile ex Helianthus annuus pour la production de monoglycérides d'acides gras Download PDF

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Publication number
EP0289968B1
EP0289968B1 EP88106971A EP88106971A EP0289968B1 EP 0289968 B1 EP0289968 B1 EP 0289968B1 EP 88106971 A EP88106971 A EP 88106971A EP 88106971 A EP88106971 A EP 88106971A EP 0289968 B1 EP0289968 B1 EP 0289968B1
Authority
EP
European Patent Office
Prior art keywords
acid
weight
fatty
fatty acid
glycerol
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 - Lifetime
Application number
EP88106971A
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German (de)
English (en)
Other versions
EP0289968A1 (fr
Inventor
Horst Dr. Eierdanz
Hans Dr. Pfeiffer
Michael Dr. Vogt
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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
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Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to AT88106971T priority Critical patent/ATE62016T1/de
Publication of EP0289968A1 publication Critical patent/EP0289968A1/fr
Application granted granted Critical
Publication of EP0289968B1 publication Critical patent/EP0289968B1/fr
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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
    • C11C3/04—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 esterification of oleic acid with glycerin, since the glycerol trioleate required for glycerolysis can only be produced technically over 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 can be used 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 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, for example by Allow molecular distillation to 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 a widely used analytical device for testing the oxidation stability of unsaturated oils in the food industry.
  • 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 product, 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.
  • 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 fine-homogenized twice in a high-pressure homogenizer at 120 bar.
  • the glycerol monooleate according to the invention has superior emulsifier properties compared to those according to the prior art.

Landscapes

  • 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)

Claims (1)

1. Utilisation d'une huile grasse de helianthus annuus (tournesol) ayant une teneur en acide oléique de 78-92% en poids et une teneur en acide linoléique de 2 à 8% en poids, respectivement rapportés aux acides gras totaux qui y sont contenus, le reste (à 100% en poids) étant le cas échéant de l'acide palmitique, et de l'acide stéarique,ainsi que jusqu 'à 1% en poids d'acides gras choisis dans le groupe constitué par l'acide myristique, l'acide palmitoléique, l'acide linolénique, l'acide arachidique, l'acide eicosénoïque et l'acide erucique, à l'exclusion des étapes d'enrichissement en ce qui concerne la teneur en acide oléique, en vue de l'obtention de monoglycérides d'acide gras par
a) transestérification en présence de glycérol ou
b) par coupure des graisses et réaction des acides gras par coupure obtenus, avec du glycérol.
EP88106971A 1987-05-08 1988-04-30 Utilisation d'une huile ex Helianthus annuus pour la production de monoglycérides d'acides gras Expired - Lifetime EP0289968B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT88106971T ATE62016T1 (de) 1987-05-08 1988-04-30 Verwendung eines fetten oeles ex helianthus annuus zur herstellung von fettsaeure-monoglyceriden.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3715424A DE3715424C2 (de) 1987-05-08 1987-05-08 Verwendung eines fetten Öles aus Helianthus annuus zur Herstellung von Fettsäure-Monoglyceriden
DE3715424 1987-05-08

Publications (2)

Publication Number Publication Date
EP0289968A1 EP0289968A1 (fr) 1988-11-09
EP0289968B1 true EP0289968B1 (fr) 1991-03-27

Family

ID=6327129

Family Applications (1)

Application Number Title Priority Date Filing Date
EP88106971A Expired - Lifetime EP0289968B1 (fr) 1987-05-08 1988-04-30 Utilisation d'une huile ex Helianthus annuus pour la production de monoglycérides d'acides gras

Country Status (6)

Country Link
EP (1) EP0289968B1 (fr)
JP (1) JPS63287749A (fr)
AT (1) ATE62016T1 (fr)
CA (1) CA1313381C (fr)
DE (2) DE3715424C2 (fr)
ES (1) ES2021786B3 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4236340C2 (de) * 1992-10-28 1994-11-10 Daimler Benz Ag Anordnung zur induktiven Übertragung von Energie
GB9416846D0 (en) * 1994-08-19 1994-10-12 Croda Int Plc Lipid supplementation
FR2750159B1 (fr) * 1996-06-24 1998-08-07 Inst Francais Du Petrole Methode et systeme d'estimation en temps reel d'au moins un parametre lie au comportement d'un outil de fond de puits
FR2752850A1 (fr) * 1996-08-27 1998-03-06 Inst Francais Du Petrole Compositions d'additifs ameliorant le pouvoir lubrifiant des carburants et carburants les contenant
WO2017085737A1 (fr) * 2015-11-19 2017-05-26 Fine Research & Development Centre Pvt Ltd Monoglycéride naturel présentant une odeur et un arôme améliorés

Family Cites Families (4)

* Cited by examiner, † Cited by third party
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 (de) * 1957-01-04 1961-02-16 E F Drew & Co Inc Verfahren zur Herstellung von Monoglyceriden von Fettsaeuren mit 8 bis 22 Kohlenstoffatomen
US2976251A (en) * 1957-04-19 1961-03-21 Eastman Kodak Co Glycerol fatty acid partial ester gels
US4627192B1 (en) * 1984-11-16 1995-10-17 Sigco Res Inc Sunflower products and methods for their production

Also Published As

Publication number Publication date
DE3715424A1 (de) 1988-11-17
ATE62016T1 (de) 1991-04-15
JPS63287749A (ja) 1988-11-24
CA1313381C (fr) 1993-02-02
ES2021786B3 (es) 1991-11-16
DE3715424C2 (de) 1995-01-26
EP0289968A1 (fr) 1988-11-09
DE3862147D1 (de) 1991-05-02

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