EP3428255B1 - Verfahren zur herstellung von raffiniertem palmfett/-öl und verfahren zur reduzierung glycidol, 3-chlorpropan-1,2-diol und fettsäureestern davon und/oder diglyceriden in raffinierten palmfett/-öl - Google Patents

Verfahren zur herstellung von raffiniertem palmfett/-öl und verfahren zur reduzierung glycidol, 3-chlorpropan-1,2-diol und fettsäureestern davon und/oder diglyceriden in raffinierten palmfett/-öl Download PDF

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EP3428255B1
EP3428255B1 EP17762978.9A EP17762978A EP3428255B1 EP 3428255 B1 EP3428255 B1 EP 3428255B1 EP 17762978 A EP17762978 A EP 17762978A EP 3428255 B1 EP3428255 B1 EP 3428255B1
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oil
palm
based fat
fat
raw material
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EP3428255A4 (de
EP3428255A1 (de
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Hiroyuki KOZUI
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Nisshin Oillio Group Ltd
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Nisshin Oillio Group Ltd
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B3/00—Refining fats or fatty oils
    • C11B3/12—Refining fats or fatty oils by distillation

Definitions

  • the present invention relates a method of producing a refined palm-based fat and/or oil, and a method of reducing glycidol, 3-chloropropane-1,2-diol, and fatty acid esters thereof, and/or diglyceride in the refined palm-based fat and/or oil.
  • Fats and/or oils contain trace components which may be implicated in physiology activities. These trace components include glycidol, 3-chloropropane-1,2-diol, fatty acid esters thereof.
  • the above trace components are suspected to be linked with nutritional problems, but unlikely constitute a direct threat to health as long as they are in those levels where they are included in fats and/or oils such as plant oils which have a good track record in ingestion through diets over a period of many years. In line with this, the tolerable upper intake level and other standards are not established. However, due to the demands for safer fats and/or oils, various methods of reducing the aforementioned components in fats and/or oils have been proposed.
  • Glycidol, 3-chloropropane-1,2-diol, and fatty acid esters thereof are known to be generated during a deodorizing step and other.
  • diglyceride is a known agent responsible for 3-chloropropane-1,2-diol (Nonpatent Document 1). It is recognized that a high concentration of 3-chloropropane-1,2-diol tends to be present in diglyceride-rich fats and/or oils, particularly in refined palm-based fats and/or oils (palm oil, palm kernel oil).
  • Patent Document 1 provides a method of reducing glycidol, 3-chloropropane-1,2-diol, fatty acid esters thereof, in fats and/or oils such as palm oil, the method including: bleaching a deodorized oil with white clay at a pH of 5 to 7; and further performing deodorization.
  • Patent Document 2 provides a method of controlling an increase in glycidol and fatty acid esters thereof, the method including: performing deodorization at a high temperature and a high vapor amount.
  • Non-Patent Document 1 LWT-Food Science and Technology 42 (2009) 1751-1754
  • WO2015/073359 discloses obtaining a refined fat and/or oil by performing short-path distillation treatment.
  • this document does not disclose feeding rate per unit area of an evaporation surface.
  • glycidol may not be sufficiently reduced in the deodorizing step due to prolonged exposure of a fat and/or oil to a high temperature. Therefore, there have been demands for a method capable of reducing generation of glycidol in a step other than the deodorizing step.
  • An object of the present invention is to provide a method of producing a refined palm-based fat and/or oil in which the contents of glycidol, 3-chloropropane-1,2-diol, and fatty acid esters thereof, and/or diglyceride can be reduced.
  • a method of producing a refined palm-based fat and/or oil in which the contents of glycidol, 3-chloropropane-1,2-diol, and fatty acid esters thereof, and/or diglyceride can be reduced.
  • the method of produce according to an embodiment of the present invention includes a step of performing thin-film distillation treatment of a raw material palm-based fat and/or oil at a temperature condition of 190 °C or more and 290°C or less to obtain a refined palm-based fat and/or oil.
  • a temperature condition of 190 °C or more and 290°C or less to obtain a refined palm-based fat and/or oil.
  • a raw material palm-based fat and/or oil is subjected to thin-film distillation treatment.
  • thin-film distillation treatment means that a raw material palm-based fat and/or oil is allowed to form a thin-film, and heated under a reduced pressure to effect evaporation.
  • a residue (a thin-film distillated fat and/or oil) in which a distillate is separated from the raw material palm-based fat and/or oil can be obtained through the above treatment.
  • the distillate may contain fatty acid, monoglyceride, and/or diglyceride.
  • the residue may contain triglyceride.
  • refined palm-based fat and/or oil refers to a palm-based fat and/or oil (a thin-film distillated fat and/or oil) subjected to at least thin-film distillation treatment.
  • the temperature condition for the thin-film distillation treatment in an embodiment of the present invention corresponds to a temperature at an evaporation surface of a thin-film distillator. That is, the phase "the temperature condition for thin-film distillation treatment is 190 °C or more and 290°C or less" means that the temperature at an evaporation surface of a thin-film distillator is 190 °C or more and 290°C or less.
  • the temperature condition for thin-film distillation treatment corresponds to an evaporator tube temperature when the thin-film distillation treatment is performed with a short-path distillator.
  • a temperature condition of 155°C or more for thin-film distillation treatment can remove thermally unstable substances, high-boiling point substances, included in a raw material palm-based fat and/or oil while efficiently suppressing generation of a trace component such as glycidol, 3-MCPD, and fatty acid esters thereof in the raw material palm-based fat and/or oil.
  • the temperature condition for thin-film distillation treatment is 190°C or more.
  • a temperature condition of 290°C or less for thin-film distillation treatment enables efficient distillation of a fat and/or oil while suppressing generation of a trace component such as glycidol, 3-MCPD, and fatty acid esters thereof, which tend to be generated at a high temperature condition.
  • the temperature condition for thin-film distillation treatment is preferably 270°C or less, more preferably 250°C or less.
  • the degree of vacuum in an embodiment of the present invention is preferably close to 0 (zero) Pa because a trace component such as glycidol, 3-MCPD, and fatty acid esters thereof; thermally unstable substances; high-boiling point substances; can be removed more easily.
  • the thin-film distillation treatment in an embodiment of the present invention may be preferably performed under a degree of vacuum of 1.0 Pa or less, more preferably 0.5 Pa or less, and even more preferably 0.3 Pa or less.
  • degree of vacuum as used herein is expressed in accordance with the absolute pressure. The value is expressed relative to the absolute vacuum which is considered as zero, and represents how close to the ideal vacuum state (the absolute vacuum).
  • the processing time for thin-film distillation treatment refers to a period of time while a fat and/or oil stays on an evaporation surface of a thin-film distillator.
  • the processing time may be preferably 1 second or more, more preferably 3 seconds or more in order to effect sufficient distillation.
  • the processing time for thin-film distillation treatment is preferably 5 minutes or less, more preferably 3 minutes or less, even more preferably 1 minute or less, and most preferably 30 seconds or less in order to reduce heat effects on a raw material palm-based fat and/or oil.
  • the processing time for thin-film treatment is related to the processing rate for thin-film treatment.
  • the processing rate for thin-film treatment can be expressed in terms of the "oil feeding rate per unit area of an evaporation surface.”
  • the term "oil feeding rate per unit area of an evaporation surface” as used herein refers to a value obtainable by dividing the feeding rate of a raw material palm-based oil/fat per hour by the area of the evaporation surface.
  • the "oil feeding rate per unit area of an evaporation surface” in an embodiment of the present invention is 2.00 ⁇ 10 -3 L/h ⁇ cm 2 or more, preferably 7.00 ⁇ 10 -3 L/cm 2 or more in order to reduce heat effects on a raw material palm-based fat and/or oil. Further, the "oil feeding rate per unit area of an evaporation surface” is 10.0 ⁇ 10 -3 L/h.cm 2 or less in order to effect sufficient distillation.
  • the types of thin-film distillation include molecular distillation which is performed under high vacuum ( ⁇ 0.1 Pa) and in which a condenser is arranged within a distance shorter than the mean free path of evaporating molecules; and short-path distillation which is performed at 0.1 Pa or more and in which a condenser is arranged at around a distance equal to the mean free path of evaporating molecules.
  • the short-path distillation treatment is preferably performed in an embodiment of the present invention in view of high efficiency of distillation.
  • a thin-film distillator used in thin-film distillation treatment evaporators of falling liquid film, centrifugal, rising liquid film, wiped film, may be used. Wiped film evaporators are preferred because the residence time of a raw material palm-based fat and/or oil within a thin-film distillator can be short enough to reduce heat effects on a raw material palm-based fat and/or oil.
  • a material of an evaporation surface of a thin-film distillator but those made of glass or stainless steel may be used.
  • timing to perform thin-film distillation treatment in a refinement step of a palm-based fat and/or oil is not particular limitation.
  • a raw material palm-based fat and/or oil may be pre-treated through a refinement step other than thin-film distillation treatment, or unrefined.
  • a raw material palm-based fat and/or oil pre-treated through a deodorizing step is preferred because the contents of glycidol, 3-chloropropane-1,2-diol, and fatty acid esters thereof, and diglyceride can be reduced more easily by thin-film distillation treatment.
  • a raw material palm-based fat and/or oil without pre-treatment in a deodorizing step may also be used.
  • the content of diglyceride may be reduced more easily by thin-film distillation treatment, and a deodorizing step may be then performed after the thin-film distillation treatment to effect more efficient reduction of the contents of glycidol, 3-chloropropane-1,2-diol, and fatty acid esters thereof.
  • thin-film distillation treatment may be performed at any timing after the respective refinement step (one or more of a degumming step, a deacidifying step, a water-washing step, a bleaching step, a deodorizing step, a fractionating step).
  • the resulting fat and/or oil obtained after thin-film distillation treatment may be directly distributed as a refined palm-based fat and/or oil, or may be subjected to an additional refinement step.
  • the raw material palm-based fat and/or oil is a palm-based fat and/or oil obtained through a deodorizing step
  • the palm-based fat and/or oil may be subjected to a fractionating step after thin-film distillation treatment.
  • the raw material palm-based fat and/or oil is an unrefined palm-based fat and/or oil
  • the resulting fat and/or oil after thin-film distillation treatment may be directly distributed as a refined palm-based fat and/or oil, or may be subjected to an additional refinement step.
  • each refinement step a degumming step, a deacidifying step, a water-washing step, a bleaching step, a deodorizing step, a fractionating step
  • conditions commonly used in refinement of fats and/or oils may be used.
  • Palm-based fats and/or oils use for an embodiment the present invention include fats and/or oils from palm.
  • palm-based fats and/or oils include, for example, palm oil, palm kernel oil, fractionated oils of palm oil, fractionated oils of palm kernel oil, hydrogenated oils of palm oil, hydrogenated oils of palm kernel oil, hydrogenated oils of fractionated oils of palm oil, hydrogenated oils of fractionated oils of palm kernel oil, and transesterified oils thereof.
  • fractionated oils of palm oil include super olein, palm olein, palm mid fraction, and palm stearin.
  • Fractionated oils of palm kernel oil include palm kernel olein and palm kernel stearin.
  • the raw material palm-based fat and/or oil may be subjected to the aforementioned thin-film distillation treatment, but palm-based fats and/or oils may be used which are pre-treated through a refinement step (a degumming step, a deacidifying step, a water-washing step, a bleaching step, a deodorizing step, a fractionating step, and/or the like) other than thin-film distillation treatment, or unrefined palm-based fats and/or oils may be used.
  • the raw material palm-based fat and/or oil is preferably a palm-based fat and/or oil pre-treated through a deodorizing step.
  • the method of refining a fat and/or oil may be either chemical refinement (chemical refining) or physical refinement (physical refining).
  • chemical refining a crude oil obtained by squeezing/extracting plant as a raw material is refined by performing degumming treatment, alkali deacidification treatment, bleaching treatment, dewaxing treatment, deodorizing treatment to obtain a refined fat and/or oil.
  • physical refinement a crude oil is refined by performing degumming treatment, non-alkali deacidification treatment such as distillation, bleaching treatment, deodorizing treatment to obtain a refined fat and/or oil.
  • RBD Refined Bleached Deodorized
  • the iodine value is preferably less than 58 in view of having less unsaturated fatty acids, less generation of trans-fatty acids, and high oxidation stability.
  • the main component of a raw material palm-based fat and/or oil is glyceride, and other components, for example, plant sterol, lecithin, antioxidant components (tocopherol), coloring components may be contained.
  • the method of produce according to an embodiment of the present invention can provide a refined palm-based fat and/or oil having reduced contents of glycidol, 3-chloropropane-1,2-diol, and fatty acid esters thereof, and diglyceride.
  • the total amount of glycidol and fatty acid esters thereof (in terms of glycidol) in a refined palm-based fat and/or oil can be reduced to 50% or less, more preferably 35% or less, and more preferably 20% or less of the total amount of glycidol and fatty acid esters thereof (in terms of glycidol) in a raw material palm-based fat and/or oil.
  • the total amount of 3-chloropropane-1,2-diol and fatty acid esters thereof (in terms of 3-chloropropane-1,2-diol) in a refined palm-based fat and/or oil can be reduced to 95% or less, more preferably 90% or less, and more preferably 60% or less of the total amount of 3-chloropropane-1,2-diol and fatty acid esters thereof (in terms of 3-chloropropane-1,2-diol) in a raw material palm-based fat and/or oil.
  • the total amount of diglyceride in a refined palm-based fat and/or oil can be reduced to 65% or less, preferably 50% or less, and more preferably 45% or less of the total amount of diglyceride in a raw material palm-based fat and/or oil.
  • the acid value, peroxide value of a refined palm-based fat and/or oil can also be reduced. Therefore, the method of produce according to an embodiment of the present invention can provide a highly refined fat and/or oil.
  • the color value (a value computed in accordance with the method described below in Examples) of a refined palm-based fat and/or oil obtained by the method of produce according to an embodiment of the present invention preferably differs from that of a raw material palm-based fat and/or oil by ⁇ 2 and more preferably by ⁇ 1, and even more preferably it is substantially the same as that of a raw material palm-based fat and/or oil.
  • the contents of glycidol, 3-chloropropane-1,2-diol, and fatty acid esters thereof, and diglyceride in a fat and/or oil as well as the acid value, peroxide value, and color value thereof may be determined according to the methods described in Examples.
  • distillate percentage refers to a percentage of a distillate over the total amount of the residue and distillate withdrawn.
  • residue percentage refers to a percentage of a residue over the total amount of the residue and distillate withdrawn.
  • the raw material palm-based fat and/or oil before the short-path distillation treatment, and the residues after the short-path distillation treatment (which correspond to a refined palm-based fat and/or oil) were investigated for their physical properties and compositions.
  • MCPD-FS total amount of 3-MCPD, glycidol, and fatty acid esters thereof in terms of 3-MCPD
  • an internal standard (a 20 ⁇ g/mL solution of 3-MCPD-d5) was added to 100 mg of each refined fat and/or oil, and then 1 mL of a sodium methoxide solution (0.5 mol/L methanol) was added. The reaction was allowed at room temperature for saponification decomposition. To this, 3 mL of brine (20%) having a trace amount of acetic acid and 3 mL of hexane were then added and mixed. Subsequently, hexane was removed.
  • an internal standard a 20 ⁇ g/mL solution of 3-MCPD-d5
  • a sodium methoxide solution 0.5 mol/L methanol
  • an internal standard (a 20 ⁇ g/mL solution of 3-MCPD-d5) was added to 100 mg of each refined fat and/or oil, and then 1 mL of a sodium methoxide solution (0.5 mol/L methanol) was added. The reaction was allowed at room temperature for saponification decomposition. To this, 3 mL of aqueous sodium bromide (50%) having a trace amount of acetic acid and 3 mL of hexane were then added and mixed. Subsequently, hexane was removed.
  • an internal standard a 20 ⁇ g/mL solution of 3-MCPD-d5
  • a sodium methoxide solution 0.5 mol/L methanol
  • True MCPD in the table below represent the percentage of True MCPD in each refined palm-based fat and/or oil relative to True MCPD in a raw material palm-based fat and/or oil.
  • True MCPD in a refined palm-based fat and/or oil (3.2 mg/kg) is about 94.1% relative to True MCPD in a raw material palm-based fat and/or oil (3.4 mg/kg).
  • the amount of glycidol in each refined fat and oil (the total amount of glycidol and fatty acid esters thereof in terms of glycidol) was computed based on the following formula.
  • Amount of glycidol MCPD ⁇ FS ⁇ True MCPD ⁇ 0.67 wherein "0.67" is a value obtained by dividing the molecular weight (74.1) of glycidol by the molecular weight (110.54) of 3-MCPD.
  • the numerical values in the parentheses under the item "glycidol” in the table below represent the percentage of the amount of glycidol in each refined palm-based fat and/or oil relative to the amount of glycidol in a raw material palm-based fat and/or oil.
  • the amount of glycidol in a refined palm-based fat and/or oil (0.2 mg/kg) is about 33.3% relative to the amount of glycidol in a raw material palm-based fat and/or oil (0.6 mg/kg).
  • the numerical values in the parentheses under the item "diglyceride” in the table below represent the percentage of the amount of diglyceride in each refined palm-based fat and/or oil relative to the amount of diglyceride in a raw material palm-based fat and/or oil.
  • the amount of diglyceride in a refined palm-based fat and/or oil (7.5 mass%) is about 94.9% relative to the amount of diglyceride in a raw material palm-based fat and/or oil (7.9 mass%).
  • the method of produce according to an embodiment of the present invention can reduce values of all of MCPD-FS, True MCPD, glycidol, and diglyceride, and thus can reduce the amounts of glycidol, 3-chloropropane-1,2-diol, and fatty acid ester thereof, and diglyceride in a palm-based fat and/or oil.
  • the method of produce according to an embodiment of the present invention was also able to reduce the acid values and the peroxide value.
  • the following treatment was performed using a short-path distillator Model KD6 (UIC GmbH; stainless-steel evaporation surface; 600 cm 2 ; condensation surface: 600 cm 2 ; maximum flow rate: 14 L/hr) instead of the short-path distillator Model KDL5 used in Examples 1 to 4.
  • the short-path distillation treatment was performed at a temperature of an evaporation tube of 270°C and at an altered feeding rate of the raw material palm-based fat and/or oil.
  • the "oil feeding rate per unit area of an evaporation surface" in Table 3 represents a value obtained by dividing the feeding rate of the raw material palm-based fat and/or oil per hour by the area (in this example, 600 cm 2 ) of the evaporation surface.
  • the raw material palm-based fat and/or oil before the short-path distillation treatment, and the residues after the short-path distillation treatment from Examples 5 to 9 were investigated for their physical properties and compositions as in Examples 1 to 4. Further, the raw material palm-based fat and/or oil before the short-path distillation treatment, and the residues after the short-path distillation treatment ware measured for chromaticity as described below to compute their color values. The results are shown in Table 4.
  • Y value, R value Chromaticity
  • Table 4 shows that similarly to the results from Examples 1 to 4, values of all of MCPD-FS, True MCPD, glycidol, and diglyceride can also be reduced in Examples 5 to 9, and thus the amounts of glycidol, 3-chloropropane-1,2-diol, and fatty acid esters thereof, and diglyceride in a palm-based fat and/or oil can be reduced.
  • the following treatment was performed as in Examples 5 to 9 using a short-path distillator Model KD6.
  • a raw material palm-based fat and/or oil (an RBD palm oil, iodine value 52) was introduced to an evaporation surface of the short-path distillator Model KD6, and thin-film distillation treatment (in this example, short-path distillation treatment) was performed under the conditions shown in Table 5.
  • the short-path distillation treatment was performed at a "feeding rate per unit area of an evaporation surface" of 7.20 ⁇ 10 -3 L/h ⁇ cm 2 and at an altered temperature of an evaporation tube.
  • Example 10 Example 11
  • Example 12 Evaporation tube temperature (°C) 210 230 250 290 Internal condenser temperature (°C) 60 60 60 60 60 60 Degree of vacuum (Pa) 0.01 0.01 0.01 0.02 Distillate percentage (% by mass) 0 1.4 3.2 31.6 Residue percentage (% by mass) 100 98.6 96.8 68.4 Oil feeding rate per unit area of an evaporation surface ( ⁇ 10 -3 L/h ⁇ cm 2 ) 7.20 7.20 7.20 7.20 7.20
  • Table 6 shows that similarly to the results from Examples 1 to 9, values of all of MCPD-FS, True MCPD, glycidol, and diglyceride can also be reduced in Examples 10 to 13, and thus the amounts of glycidol, 3-chloropropane-1,2-diol, and fatty acid esters thereof, and diglyceride in a palm-based fat and/or oil can be reduced.

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Claims (7)

  1. Verfahren zur Herstellung von raffiniertem Fett und/oder Öl auf Palmbasis, wobei das Verfahren einen Schritt der Durchführung einer Dünnschicht-Destillation eines rohen Fetts und/oder Öls auf Palmbasis unter Temperaturbedingungen von 190 °C oder darüber und 290 °C oder darunter, einem Vakuumgrad nahe 0,3 Pa oder darunter, und einer Ölzufuhrrate pro Flächeneinheit einer Verdampfungsoberfläche von 2,00 × 10-3 l/h · cm2 oder mehr und 10 × 10-3 1/h · cm2 oder weniger umfasst, um das raffinierte Fett und/oder Öl auf Palmbasis zu erhalten, wobei die Gesamtmenge an Diglycerid in dem raffinierten Fett und/oder Öl auf Palmbasis 65 % oder weniger der Gesamtmenge an Diglycerid in dem rohen Fett und/oder Öl auf Palmbasis beträgt.
  2. Verfahren zur Herstellung von raffiniertem Fett und/oder Öl auf Palmbasis nach Anspruch 1, wobei die Gesamtmenge an Glycidol und Fettsäureestern davon, ausgedrückt als Glycidol, in dem raffinierten Fett und/oder Öl auf Palmbasis 50 % oder weniger der Gesamtmenge an Glycidol und Fettsäureestern davon, ausgedrückt als Glycidol, in dem rohen Fett und/oder Öl auf Palmbasis beträgt.
  3. Verfahren zur Herstellung von raffiniertem Fett und/oder Öl auf Palmbasis nach Anspruch 1 oder 2, wobei die Gesamtmenge an 3-Chlorpropan-1,2-diol und Fettsäureestern davon, ausgedrückt als 3-Chlorpropan-1,2-diol, in dem raffinierten Fett und/oder Öl auf Palmbasis 95 % oder weniger der Gesamtmenge an 3-Chlorpropan-1,2-diol und Fettsäureestern davon, ausgedrückt als 3-Chlorpropan-1,2-diol, in dem rohen Fett und/oder Öl auf Palmbasis beträgt.
  4. Verfahren zur Herstellung von raffiniertem Fett und/oder Öl auf Palmbasis nach einem der Ansprüche 1 bis 3, wobei das rohe Fett und/oder Öl auf Palmbasis durch einen Desodorisierungsschritt vorbehandelt wird.
  5. Verfahren zur Herstellung von raffiniertem Fett und/oder Öl auf Palmbasis nach einem der Ansprüche 1 bis 4, wobei der Vakuumgrad in der Dünnschicht-Destillationsbehandlung < 0,1 Pa ist.
  6. Verfahren zur Herstellung von raffiniertem Fett und/oder Öl auf Palmbasis nach einem der Ansprüche 1 bis 5, wobei die Dünnschicht-Destillationsbehandlung eine Kurzweg-Destillationsbehandlung ist.
  7. Verfahren zur Herstellung von raffiniertem Fett und/oder Öl auf Palmbasis nach einem der Ansprüche 1 bis 6, wobei ein Jodwert des rohen Fetts und/oder Öls auf Palmbasis weniger als 58 beträgt.
EP17762978.9A 2016-03-11 2017-02-27 Verfahren zur herstellung von raffiniertem palmfett/-öl und verfahren zur reduzierung glycidol, 3-chlorpropan-1,2-diol und fettsäureestern davon und/oder diglyceriden in raffinierten palmfett/-öl Active EP3428255B1 (de)

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JP2016047999 2016-03-11
PCT/JP2017/007478 WO2017154638A1 (ja) 2016-03-11 2017-02-27 精製パーム系油脂の製造方法、並びに、精製パーム系油脂中のグリシドール、３－クロロプロパン－１，２－ジオール、及びこれらの脂肪酸エステル、及び／又はジグリセリドの低減方法

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EP3428255A1 EP3428255A1 (de) 2019-01-16
EP3428255A4 EP3428255A4 (de) 2019-08-21
EP3428255B1 true EP3428255B1 (de) 2022-03-30

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SG11202002426YA (en) * 2017-09-19 2020-04-29 Cargill Inc Infant food product
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WO2017154638A1 (ja) 2017-09-14
JPWO2017154638A1 (ja) 2018-09-13

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