EP0105622A2 - Verfahren zur Umesterung eines essbaren Öls - Google Patents

Verfahren zur Umesterung eines essbaren Öls Download PDF

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Publication number
EP0105622A2
EP0105622A2 EP83305127A EP83305127A EP0105622A2 EP 0105622 A2 EP0105622 A2 EP 0105622A2 EP 83305127 A EP83305127 A EP 83305127A EP 83305127 A EP83305127 A EP 83305127A EP 0105622 A2 EP0105622 A2 EP 0105622A2
Authority
EP
European Patent Office
Prior art keywords
oil
content
temperature
safa
interesterification
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.)
Withdrawn
Application number
EP83305127A
Other languages
English (en)
French (fr)
Other versions
EP0105622A3 (de
Inventor
Cornelis Nicolaas Maria Keulemans
Adrianus Rozendaal
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.)
Unilever PLC
Unilever NV
Original Assignee
Unilever PLC
Unilever NV
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 Unilever PLC, Unilever NV filed Critical Unilever PLC
Publication of EP0105622A2 publication Critical patent/EP0105622A2/de
Publication of EP0105622A3 publication Critical patent/EP0105622A3/de
Withdrawn legal-status Critical Current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
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/10—Ester interchange

Definitions

  • the present invention relates to a method for treating an edible oil, to an oil so prepared and to margarine produced from the said oil.
  • An oil suitable for use in margarine manufacture is conventionally prepared from a mixture of triglycerides obtained from a vegetable, animal and/or a marine source by full or partial hydrogenation of any unsaturated fatty acids present.
  • Other methods of raising the melting point of a triglyceride mixture and, hence, its solid phase content at ambient temperature are, however, known.
  • One of these methods is so-called directed interesterification of the triglyceride mixture and is for example described, mainly in relation to plastic shortenings, by Eckey in his US Patent Specification No. 2,442,532.
  • the method comprises the addition of a catalyst to the oil mixture to cause random redistribution of the fatty acids, followed by cooling to a temperature at which at least one of the triglycerides present crystallises out of solution.
  • the said triglyceride or triglycerides formed by the random action of the catalyst and crystallising out of solution cause the statistical distribution of the interesterification products formed to be upset. Further high melting triglyceride is thus preferentially formed in an attempt to restore the equilibrium and continues to crystallise.. Once sufficient of the solid triglyceride has formed to bring the mixture to an overall desired solid phase content the reaction is stopped.
  • the all-liquid triglyceride mixture can, for example prior to interesterification, be first slightly cooled to crystallise some of the high melting triglyceride which subsequently acts as seed crystals.
  • UK Patent Specification No. 1,381,721 describes a process for directed interesterification of glyceride esters in which the mixture is alternately subjected, at least three times, to a temperature below the cloud point of a randomised mixture of the triglycerides, followed by a temperature above the cloud point of the mixture.
  • suitable margarine oil can be prepared from, for example, sunflower oil, after only 24 hours of so-called temperature cycling.
  • European Patent Application No. 79 103419 Publication No. 0,009,207 describes another directed interesterification process suitable for oils high in pufa in which temperature cycling occurs in a number of closely specified heating and cooling steps.
  • European Patent Application No. 82 301200 we described a method for treating a triglyceride oil in which the reaction rates attained, as measured by increase in solid fat content, are comparable to those obtained employing temperature cycling techniques.
  • the method described in EP 82 301200 comprises subjecting an oil rich in pufa and having a certain safa (saturated fatty acid) content-to directed interesterification under isothermal conditions.
  • the absence of temperature cycling requirements obviates the need for a succession of closely monitored and controlled different steps and thus leads to a cost reduction.
  • a method for treating an edible oil having triglycerides .rich in linoleic acid characterised in that the oil has a p u fa (polyunsaturated fatty acid) content of at least 60% and a safa (saturated fatty acid) content of between 12.5% and 16%, the method comprising bringing the oil into contact with an interesterification catalyst, cooling the reaction mixture at a cooling rate within the range of from about 5°C per minute to about 5°C per second to a temperature at which directed interesterification will occur and maintaining the reaction mixture under isothermal conditions at said temperature.
  • the present invention extends to oils treated by the present process and to margarine prepared from the said oils.
  • oil and “fat” are used interchangeably.
  • isothermal conditions we mean a temperature which is maintained substantially constant. Slight fluctuations may occur without deviating from the present invention.
  • fatty acids is taken to mean fatty acid moieties forming part of the triglycerides.
  • the reaction mixture is.preferably cooled at the present cooling rate from a temperature at which the interesterification catalyst is activated.
  • the activation temperature suitably lies within the range of from 45°C to 75°C. Where an activation temperature in the region of 70°C is selected the temperature need only be maintained momentarily. Where however an activation temperature is selected in the region of 50°C the reaction mixture is preferably maintained at this temperature for a few minutes before cooling commences.
  • Suitable catalysts for use in the present process include sodium ethoxide, potassium ethoxide, sodium methoxide, potassium methoxide and sodium/potassium alloys.
  • the controlled cooling step can for example be performed by employing a heat exchanger such as a plate heat exchanger.
  • the edible oil used in the present process may consist of one or more naturally occurring oils.
  • at least a part of the safa content of the oil comprises hydrogenated fatty acids.
  • the hydrogenated fatty ⁇ acids comprise 3 to 5% of the edible oil subjected to the present process.
  • the pufa content of the edible oil is preferably provided in total by linoleic acid.
  • the edible oil can comprise a blend of oils comprising one or more, preferably naturally occurring, oils having a high pufa content and one or more oils having a high safa content.
  • “high” we mean at least 35wt%, preferably at least 50 wt%, more preferably at least 70 wt%.
  • the oil having a high safa content can for example be a fully or partially hydrogenated oil and may be a fully or partially hydrogenated sample of the oil having a high pufa content. It may alternatively comprise a hydrogenated fat randomly interesterified with another fat.
  • an oil having a high pufa content is mixed with an oil high in safa to produce a blend of oils having the required fatty acid composition.
  • the blend of oils comprises from 95 to 97% naturally occurring oil having a high pufa content and 5 to 3% oil having a high safa content.
  • the process can and preferably is performed in the absence of any solvent.
  • a suitable temperature for performing the directed interesterification step with both sunflower oil and safflower seed oil has been found to lie in the range of from about -5°C to about 12°C, preferably from about 0°C to 8°C and is most preferably about 3°C at which temperature the triglycerides crystallising out of solution comprise substantially a mixture of trisaturated glycerides and mono unsaturated triglycerides.
  • the present process it is possible to produce an oil which can be employed in the manufacture of margarine as the sole fatty ingredient in the fatty phase, the oil having a ratio of polyunsaturated fatty acids to saturated fatty acids (p/s ratio) of at least 3.75.
  • the fat blends are selected within the limits of the present invention to achieve a p/s ratio of at least 4 and more preferably of at least 4.5.
  • the blend of oils contains at least 65% pufa and between 12.5 and 15% safa.
  • the mixture of oil and catalyst was passed through a plate heat exchanger at a controlled rate of cooling to attain a temperature of 3'C. The mixture was then retained at 3°C for at least 24 hours. Samples were taken periodically from the reaction mixture and assessed for their solid fat content at 3'C. N 20 values of the same samples were assessed after destruction of the catalyst. Interesterification reaction was stopped by addition of water.
  • the interesterified oil should exhibit an N value of at least 4, preferably at least 5.
  • the interesterified oil subjected to an initial cooling rate of 0.5°C/s reaches an N 20 value of 5 within 24 hours or less.
  • Interesterification of the comparative reaction mixture for a total time of 60 hours was necessary to achieve a N 20 value of 5.
  • Example 2 Employing an oil blend of 4.5 wt% sunflower oil hardened to a melting point of 69°C and 95.5 wt% safflower seed oil, as in Example 1, together with 0.8 wt% NaOEt the effect of different temperatures for the isothermal directed interesterification was investigated. In each case the procedure of Example 1 was followed, employing a cooling rate of 0.5°C/s.
  • Each of the oils prepared in Examples 1, 3 and 4 embodying the present invention were suitable for use in manufacture of margarine according to conventional practice.
  • the present oils are preferably used in manufacture of margarine as soon as possible after their treatment.

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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)
  • Edible Oils And Fats (AREA)
  • Fats And Perfumes (AREA)
EP83305127A 1982-09-06 1983-09-05 Verfahren zur Umesterung eines essbaren Öls Withdrawn EP0105622A3 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8225343 1982-09-06
GB8225343 1982-09-06

Publications (2)

Publication Number Publication Date
EP0105622A2 true EP0105622A2 (de) 1984-04-18
EP0105622A3 EP0105622A3 (de) 1984-10-17

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP83305127A Withdrawn EP0105622A3 (de) 1982-09-06 1983-09-05 Verfahren zur Umesterung eines essbaren Öls

Country Status (1)

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EP (1) EP0105622A3 (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0209176A1 (de) * 1985-07-09 1987-01-21 Unilever N.V. Fette und essbare Emulsionen mit einem hohen Gehalt an Cis-polyungesättigten Fettsäuren
US20080107791A1 (en) * 2005-07-01 2008-05-08 Martek Biosciences Corporation "Polyunsaturated Fatty Acid-Containing Oil Product and Uses and Production Thereof"

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0009207A1 (de) * 1978-09-14 1980-04-02 N.V. Safinco Verfahren zur gelenkten Umesterung eines Triglyceridöls oder einer Triglyceridölmischung
EP0050418A1 (de) * 1980-09-19 1982-04-28 NABISCO BRANDS, Inc. Verfahren zur Herstellung einer Speisefettzusammensetzung
EP0060139A2 (de) * 1981-03-11 1982-09-15 Unilever Plc Verfahren zur Behandlung eines Speiseöls

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0009207A1 (de) * 1978-09-14 1980-04-02 N.V. Safinco Verfahren zur gelenkten Umesterung eines Triglyceridöls oder einer Triglyceridölmischung
EP0050418A1 (de) * 1980-09-19 1982-04-28 NABISCO BRANDS, Inc. Verfahren zur Herstellung einer Speisefettzusammensetzung
EP0060139A2 (de) * 1981-03-11 1982-09-15 Unilever Plc Verfahren zur Behandlung eines Speiseöls

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0209176A1 (de) * 1985-07-09 1987-01-21 Unilever N.V. Fette und essbare Emulsionen mit einem hohen Gehalt an Cis-polyungesättigten Fettsäuren
US20080107791A1 (en) * 2005-07-01 2008-05-08 Martek Biosciences Corporation "Polyunsaturated Fatty Acid-Containing Oil Product and Uses and Production Thereof"

Also Published As

Publication number Publication date
EP0105622A3 (de) 1984-10-17

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Inventor name: KEULEMANS, CORNELIS NICOLAAS MARIA

Inventor name: ROZENDAAL, ADRIANUS