EP3428255A1 - Method for producing refined palm-based fat/oil, and method for reducing glycidol, 3-chloropropane-1,2-diol and fatty acid esters thereof and/or diglycerides in refined palm-based fat/oil - Google Patents

Method for producing refined palm-based fat/oil, and method for reducing glycidol, 3-chloropropane-1,2-diol and fatty acid esters thereof and/or diglycerides in refined palm-based fat/oil Download PDF

Info

Publication number
EP3428255A1
EP3428255A1 EP17762978.9A EP17762978A EP3428255A1 EP 3428255 A1 EP3428255 A1 EP 3428255A1 EP 17762978 A EP17762978 A EP 17762978A EP 3428255 A1 EP3428255 A1 EP 3428255A1
Authority
EP
European Patent Office
Prior art keywords
oil
palm
based fat
glycidol
fat
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.)
Granted
Application number
EP17762978.9A
Other languages
German (de)
French (fr)
Other versions
EP3428255A4 (en
EP3428255B1 (en
Inventor
Hiroyuki KOZUI
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.)
Nisshin Oillio Group Ltd
Original Assignee
Nisshin Oillio Group Ltd
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=59789201&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP3428255(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Nisshin Oillio Group Ltd filed Critical Nisshin Oillio Group Ltd
Publication of EP3428255A1 publication Critical patent/EP3428255A1/en
Publication of EP3428255A4 publication Critical patent/EP3428255A4/en
Application granted granted Critical
Publication of EP3428255B1 publication Critical patent/EP3428255B1/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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

  • glycidol and the like 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 and the like 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.
  • the present investors found that the above problems can be solved by adjusting a temperature condition for thin-film distillation treatment in a method of producing a refined palm-based fat and/or oil including the thin-film distillation treatment. Then, the present invention has been completed. Specifically, the present invention can provide the followings.
  • 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 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, and the like.
  • the residue may contain triglyceride and the like.
  • 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 155°C or more and 290°C or less" means that the temperature at an evaporation surface of a thin-film distillator is 155°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, and the like 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 preferably 160°C or more, more preferably 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. It is noted that for a palm-based fat and/or oil rich in unsaturated fatty acid, for example, a palm-based fat and/or oil having an iodine value of 58 or more, thin-film distillation treatment may be performed at less than 175°C in order to reduce generation of trans-fatty acid.
  • 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; and the like 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 may be preferably 2.00 ⁇ 10 -3 L/h ⁇ cm 2 or more, 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.
  • the "oil feeding rate per unit area of an evaporation surface” may be preferably 12.0 ⁇ 10 -3 L/h ⁇ cm 2 or less, more preferably 10.0 ⁇ 10 -3 L/cm 2 or less in order
  • 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 there is no particular limitation for a thin-film distillator used in thin-film distillation treatment, but evaporators of falling liquid film, centrifugal, rising liquid film, wiped film, and the like 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, and the like).
  • 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 and the like
  • 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, and the like
  • 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, and the like.
  • 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 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 and the like), coloring components and the like 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 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 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 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.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Microbiology (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)
  • Edible Oils And Fats (AREA)

Abstract

The present invention addresses the problem of providing a method for producing a refined palm-based fat and/or oil whereby the contents of glycidol, 3-chloropropane-1,2-diol and fatty acid esters thereof and/or diglycerides can be reduced. Provided is a method for producing a refined palm-based fat and/or oil that comprises a step for treating a starting palm-based fat and/or oil by thin film distillation at a temperature of 155-290oC inclusive to give the refined palm-based fat and/or oil, wherein the total amount of glycidol and fatty acid esters thereof, said total amount being calculated by regarding glycidol and fatty acid esters thereof as glycidol, in the obtained refined palm-based fat and/or oil is not more than 50% relative to the total amount of glycidol and fatty acid esters thereof, said total amount being calculated by regarding glycidol and fatty acid esters thereof as glycidol, in the starting palm-based fat and/or oil.

Description

    TECHNICAL FIELD
  • 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.
    • BACKGROUND ART
  • 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, and the like. 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 and the like 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. Moreover, diglyceride is a known agent responsible for 3-chloropropane-1,2-diol and the like (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, and the like). Accordingly, Patent Document 1, for example, provides a method of reducing glycidol, 3-chloropropane-1,2-diol, fatty acid esters thereof, and the like 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.
    • Patent Document 1: Japanese Unexamined Patent Application, Publication No. 2014-047290
    • Patent Document 2: Japanese Unexamined Patent Application, Publication No. 2013-112761
    • Non-Patent Document 1: LWT-Food Science and Technology 42(2009)1751-1754
    DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention
  • However, glycidol and the like 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 and the like in a step other than the deodorizing step.
  • The present invention is made in view of the aforementioned circumstances. 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.
    • Means for Solving the Problems
  • The present investors found that the above problems can be solved by adjusting a temperature condition for thin-film distillation treatment in a method of producing a refined palm-based fat and/or oil including the thin-film distillation treatment. Then, the present invention has been completed. Specifically, the present invention can provide the followings.
    1. (1) A method of producing a refined palm-based fat and/or oil, the method including a step of performing thin-film distillation treatment of a raw material palm-based fat and/or oil at a temperature condition of 155°C or more and 290°C or less to obtain the refined palm-based fat and/or oil, the total amount of glycidol and fatty acid esters thereof in terms of glycidol in the refined palm-based fat and/or oil being 50% or less of the total amount of glycidol and fatty acid esters thereof in terms of glycidol in the raw material palm-based fat and/or oil.
    2. (2) A method of producing a refined palm-based fat and/or oil, the method including a step of performing thin-film distillation treatment of a raw material palm-based fat and/or oil of 155°C or more and 290°C or less to obtain the refined 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 the refined palm-based fat and/or oil being 95% 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 the raw material palm-based fat and/or oil.
    3. (3) A method of producing a refined palm-based fat and/or oil, the method including a step of performing thin-film distillation treatment of a raw material palm-based fat and/or oil at a temperature condition of 155°C or more and 290°C or less to obtain the refined palm-based fat and/or oil,
      the total amount of diglyceride in the refined palm-based fat and/or oil being 65% or less of the total amount of diglyceride in the raw material palm-based fat and/or oil.
    4. (4) The method of producing a refined palm-based fat and/or oil according to any one of (1) to (3), wherein the raw material palm-based fat and/or oil is pre-treated through a deodorizing step.
    5. (5) The method of producing a refined palm-based fat and/or oil according to any one of (1) to (4), wherein the degree of vacuum in the thin-film distillation treatment is 1.0 Pa or less.
    6. (6) The method of producing a refined palm-based fat and/or oil according to any one of (1) to (5), wherein the thin-film distillation treatment is short-path distillation treatment.
    7. (7) The method of producing a refined palm-based fat and/or oil according to any one of (1) to (6), wherein the iodine value of the raw material palm-based fat and/or oil is less than 58.
    8. (8) A method of reducing glycidol, 3-chloropropane-1,2-diol, and fatty acid esters thereof, and/or diglyceride in a refined palm-based fat and/or oil, the method including performing thin-film distillation treatment of a raw material palm-based fat and/or oil at a temperature condition of 155°C or more and 290°C or less.
    Effects of the Invention
  • According to an embodiment of the present invention, provided is 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.
    • PREFERRED MODE FOR CARRYING OUT THE INVENTION
  • Below, the embodiments of the present invention will be described, but the present invention shall not be limited to the following embodiments.
  • 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 155°C or more and 290°C or less to obtain a refined palm-based fat and/or oil. Below, the thin-film distillation treatment and palm-based fats and/or oils used for an embodiment of the present invention will be described in detail.
    • [Thin-film distillation treatment]
  • According to an embodiment of the present invention, a raw material palm-based fat and/or oil is subjected to thin-film distillation treatment. The term "thin-film distillation treatment" as used herein 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, and the like. The residue may contain triglyceride and the like. The term "refined palm-based fat and/or oil" as used herein 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.
  • After conducting extensive studies, the present investors found that generation of glycidol, 3-chloropropane-1,2-diol, and fatty acid esters thereof can be reduced by adjusting a temperature condition to 155°C or more and 290°C or less when thin-film distillation treatment of a raw material palm-based fat and/or oil is performed. It is noted that hereinafter "3-chloropropane-1,2-diol" may also be referred to as "3-MCPD."
  • 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 155°C or more and 290°C or less" means that the temperature at an evaporation surface of a thin-film distillator is 155°C or more and 290°C or less. For example, 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, and the like 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. In view of an improved efficiency of distillation, the temperature condition for thin-film distillation treatment is preferably 160°C or more, more preferably 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. In view of further reduced generation of such a trace component, the temperature condition for thin-film distillation treatment is preferably 270°C or less, more preferably 250°C or less. It is noted that for a palm-based fat and/or oil rich in unsaturated fatty acid, for example, a palm-based fat and/or oil having an iodine value of 58 or more, thin-film distillation treatment may be performed at less than 175°C in order to reduce generation of trans-fatty acid.
  • 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; and the like can be removed more easily. Specifically, 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.
  • It is noted that the "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. There is no particular limitation for the processing time, but it may be preferably 1 second or more, more preferably 3 seconds or more in order to effect sufficient distillation. Further, 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 may be preferably 2.00×10-3 L/h·cm2 or more, more preferably 7.00×10-3 L/cm2 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" may be preferably 12.0×10-3 L/h·cm2 or less, more preferably 10.0×10-3 L/cm2 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.
  • There is no particular limitation for a thin-film distillator used in thin-film distillation treatment, but evaporators of falling liquid film, centrifugal, rising liquid film, wiped film, and the like 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. There is no particular limitation for a material of an evaporation surface of a thin-film distillator, but those made of glass or stainless steel may be used.
  • There is no particular limitation for the timing to perform thin-film distillation treatment in a refinement step of a palm-based fat and/or oil.
  • As described below, 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. In this case, 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.
  • For a raw material palm-based fat and/or oil pre-treated through a refinement step other than thin-film distillation treatment, 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, and the like). 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. For example, when the raw material palm-based fat and/or oil is a palm-based fat and/or oil obtained through a deodorizing step and the like, the palm-based fat and/or oil may be subjected to a fractionating step after thin-film distillation treatment.
  • When 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.
  • There is no particular limitation for the conditions for each refinement step (a degumming step, a deacidifying step, a water-washing step, a bleaching step, a deodorizing step, a fractionating step, and the like) other than thin-film distillation treatment, but conditions commonly used in refinement of fats and/or oils may be used.
    • [Raw material palm-based fat and/or oil]
  • Palm-based fats and/or oils use for an embodiment the present invention include fats and/or oils from palm. Specifically, 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, and the like. It is noted that 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.
  • There is no particular limitation for the raw material palm-based fat and/or oil to 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. As described above, the raw material palm-based fat and/or oil is preferably a palm-based fat and/or oil pre-treated through a deodorizing step. There is no particular limitation for the method of refining a fat and/or oil, but it may be either chemical refinement (chemical refining) or physical refinement (physical refining). It is noted that in the former chemical refinement, 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. In contrast, in the latter 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. It is noted that a fat and/or oil pre-treated through a degumming step, a bleaching step, a deodorizing step is called an RBD (Refined Bleached Deodorized) oil.
  • There is no particular limitation for the properties of a raw material palm-based fat and/or oil, but 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 and the like), coloring components and the like may be contained.
    • [Determination of contents of glycidol, 3-chloropropane-1,2-diol, and fatty acid esters thereof, and diglyceride in refined palm-based fat and/or oil]
  • 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.
  • Specifically, in the method of produce according to an embodiment of the present invention, 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. Further, 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. Moreover, 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.
  • Furthermore, in the method of produce according to an embodiment of the present invention, 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.
  • Still further, in the method of produce according to an embodiment of the present invention, significant coloring of a refined palm-based fat and/or oil can be prevented. 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.
    • EXAMPLES
  • Below, the present invention will be described specifically with reference to Examples, but the present invention shall not be limited to these Examples.
    • <Examples 1 to 4>
  • A raw material palm-based fat and/or oil (RBD palm oil, iodine value = 52) was introduced to an evaporation surface of a short-path distillator Model KDL5 (UIC GmbH; glass evaporation surface: 480 cm2; condensation surface: 650 cm2; maximum flow rate: 1 L/hr), and thin-film distillation treatment (in this example, short-path distillation treatment) was performed under the conditions shown in Table 1. It is noted that the residence time (that is, the processing time of thin-film distillation treatment) of the raw material palm-based fat and/or oil on the evaporation surface of the short-path distillator was set in the range from 5 seconds to 30 seconds.
  • A residue and distillate obtained after performing the short-path distillation treatment under the above conditions were withdrawn. It is noted that the "operation time" in Table 1 refers to the total operation time of the short-path distillator. The term "distillate percentage" refers to a percentage of a distillate over the total amount of the residue and distillate withdrawn. The term "residue percentage" refers to a percentage of a residue over the total amount of the residue and distillate withdrawn. [Table 1]
    Table 1
    Example 1 Example 2 Example 3 Example 4
    Operation time (minutes) 65 65 65 65
    Evaporation tube temperature (°C) 160 200 225 250
    Internal condenser temperature (°C) 45 45 45 50
    Degree of vacuum (Pa) 6.0 0.1 0.1 0.1
    Distillate percentage (% by mass) 0.2 0.3 2.3 8.9
    Residue percentage (% by mass) 99.8 99.7 97.7 91.1
    Cold trap (% by mass) 0.0 0.0 0.0 0.0
    Feeding rate (g/h) 495.3 507.0 503.4 512.1
  • 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.
  • The results are shown in Table 2.
    • [Quantification of MCPD-FS]
  • The total amount of 3-MCPD, glycidol, and fatty acid esters thereof in terms of 3-MCPD (the above total amount is referred to as "MCPD-FS") in each refined fat and/or oil was quantified in accordance with the German official method (DGF Standard Methods C-III 18 (09)).
  • Specifically, 50 µL of an internal standard (a 20 µg/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. This was then derivatized with 250 µL of aqueous phenylboric acid (25%), and extracted with 2 mL of hexane, and then measured with an instrument for gas chromatography-mass spectrometry. A chromatogram obtained from the above measurement with an instrument for gas chromatography-mass spectrometry was used to compare the ionic strength of 3-MCPD with that of the internal standard 3-MCPD-d5. Then the total amount of 3-MCPD, glycidol, and fatty acid esters thereof in a fat and/or oil was computed in terms of free 3-MCPD.
    • [Quantification of true MCPD]
  • The total amount of 3-MCPD and fatty acid esters of 3-MCPD in terms of 3-MCPD (the above total amount is referred to as "True MCPD") in each refined fat and/or oil was quantified in accordance with the German official method (DGF Standard Methods C-III 18 (09)).
  • Specifically, 50 µL of an internal standard (a 20 µg/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. This was then derivatized with 500 µL of aqueous phenylboric acid (12.5%), and extracted with 2 mL of hexane, and then measured with an instrument for gas chromatography-mass spectrometry. A chromatogram obtained from the above measurement with an instrument for gas chromatography-mass spectrometry was used to compare the ionic strength of 3-MCPD with that of the internal standard 3-MCPD-d5. Then the total amount of 3-MCPD and fatty acid esters of 3-MCPD in a glyceride composition was computed in terms of free 3-MCPD.
  • It is noted that the numerical values in the parentheses under the item "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. For example, with reference to Example 1, 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).
    • [Calculation of amount of glycidol]
  • Using the values for MCPD-FS and True MCPD determined according to the above method, 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
    Figure imgb0001
     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.
  • It is noted that 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. For example, with reference to Example 1, 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).
    • [Acid value]
  • Measurement was performed in accordance with "Standard Methods for the Analysis of Fats, Oils and Related Materials 2.3.1-1996: Acid value," Japan Oil Chemists' Society Ed.
    • [Peroxide value]
  • Measurement was performed in accordance with "Standard Methods for the Analysis of Fats, Oils and Related Materials 2.5.2.1-2013: Peroxide value," Japan Oil Chemists' Society Ed.
    • [Quantification of amount of diglyceride]
  • Measurement was performed in accordance with AOCS "Official Method Cd 11b-91, Determination of Mono- and Diglycerides by Capillary Gas Chromatography."
  • It is noted that 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. For example, with reference to Example 1, 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%). [Table 2]
    Table 2
    Raw material palm oil Example 1 Example 2 Example 3 Example 4
    MCPD-FS (mg/kg) 4.3 3.5 3.0 1.9 0.8
    True MCPD (mg/kg) 3.4 3.2 (94.1) 2.8 (82.4) 1.7 (50) 0.7 (20.6)
    Glycidol (mg/kg) 0.6 0.2 (33.3) 0.1 (16.7) 0.1 (16.7) 0.1 (16.7)
    Acid value 0.06 0.03 0.02 0.03 0.02
    Peroxide value 0.4 0.3 0.2 0.2 0.1
    Diglyceride (% by mass) 7.9 7.5 (94.9) 7.0 (88.6) 5.1 (64.6) 3.3 (41.8)
  • As shown in Table 2, 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.
    • <Examples 5 to 9>
  • The following treatment was performed using a short-path distillator Model KD6 (UIC GmbH; stainless-steel evaporation surface; 600 cm2; condensation surface: 600 cm2; maximum flow rate: 14 L/hr) instead of the short-path distillator Model KDL5 used in Examples 1 to 4. 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 3. Specifically, 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. It is noted that 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 cm2) of the evaporation surface. [Table 3]
    Table 3
    Example 5 Example 6 Example 7 Example 8 Example 9
    Evaporation tube temperature (°C) 270 270 270 270 270
    Internal condenser temperature (°C) 60 60 60 60 60
    Degree of vacuum (Pa) 0.01 0.01 0.01 0.10 0.31
    Distillate percentage (% by mass) 36.8 13.2 10.7 5.8 4.3
    Residue percentage (% by mass) 63.2 86.8 89.3 94.2 95.7
    Oil feeding rate per unit area of an evaporation surface (×10-3L/h▪cm2) 2.40 6.00 7.20 9.60 11.5
  • 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 (which correspond to a refined palm-based fat and/or oil) 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.
    • [Calculation of color value]
  • Chromaticity (Y value, R value) was measured in accordance with "Standard Methods for the Analysis of Fats, Oils and Related Materials 2.2.1-1996: Lovibond method," Japan Oil Chemists' Society Ed, and the obtained chromaticity was used to compute a color value (a value of Y + 10R). A Lovibond colorimeter (cell length: 133.4 mm) was used for the measurement. [Table 4]
    Table 4
    Raw material palm-based fat and/or oil Example 5 Example 6 Example 7 Example 8 Example 9
    MCPD-FS (mg/kg) 3.1 0.3 0.7 0.8 1.1 1.4
    True MCPD (mg/kg) 2.2 0.1 (4.5) 0.5 (22.7) 0.6 (27.3) 0.9 (40.9) 1.1 (50.0)
    Glycidol (mg/kg) 0.6 0.1 (16.7) 0.1 (16.7) 0.1 (16.7) 0.1 (16.7) 0.2 (33.3)
    Acid value 0.05 0.02 0.02 0.02 0.02 0.02
    Diglyceride (% by mass) 7.2 2.6 (36.1) 4.1 (56.9) 2.9 (40.3) 3.8 (52.7) 6.3 (87.5)
    Color value 28 48 32 30 30 30
  • 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.
    • <Examples 10 to 13>
  • 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. Specifically, 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·cm2 and at an altered temperature of an evaporation tube. [Table 5]
    Table 5
    Example 10 Example 11 Example 12 Example 13
    Evaporation tube temperature (°C) 210 230 250 290
    Internal condenser temperature (°C) 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 (×10-3L/h▪cm2) 7.20 7.20 7.20 7.20
  • 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 10 to 13 (which correspond to a refined palm-based fat and/or oil) were investigated for their physical properties (including color values) and compositions as in Examples 5 to 9. The results are shown in Table 6. [Table 6]
    Table 6
    Raw material palm oil Example 10 Example 11 Example 12 Example 13
    MCPD-FS (mg/kg) 3.1 2.1 1.9 1.3 0.5
    True MCPD (mg/kg) 2.2 1.9 (86.4) 1.5 (68.2) 1.1 (50.0) 0.4 (18.2)
    Glycidol (mg/kg) 0.6 0.1 (16.7) 0.1 (16.7) 0.1 (16.7) 0.1 (16.7)
    Acid value 0.05 0.03 0.02 0.02 0.02
    Diglyceride (% by mass) 7.2 7.0 (97.2) 6.1 (84.7) 4.8 (66.7) 1.9 (26.4)
    Color value 28 28 26 28 38
  • 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.

Claims (8)

  1. A method of producing a refined palm-based fat and/or oil, the method comprising a step of performing a thin-film distillation treatment of a raw material palm-based fat and/or oil at a temperature condition of 155°C or more and 290°C or less to obtain the refined palm-based fat and/or oil,
    the total amount of glycidol and fatty acid esters thereof in terms of glycidol in the refined palm-based fat and/or oil being 50% or less of the total amount of glycidol and fatty acid esters thereof in terms of glycidol in the raw material palm-based fat and/or oil.
  2. A method of producing a refined palm-based fat and/or oil, the method comprising a step of performing thin-film distillation treatment of a raw material palm-based fat and/or oil at a temperature condition of 155°C or more and 290°C or less to obtain the refined 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 the refined palm-based fat and/or oil being 95% 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 the raw material palm-based fat and/or oil.
  3. A method of producing a refined palm-based fat and/or oil, the method comprising a step of performing thin-film distillation treatment of a raw material palm-based fat and/or oil at a temperature condition of 155°C or more and 290°C or less to obtain the refined palm-based fat and/or oil,
    the total amount of diglyceride in the refined palm-based fat and/or oil being 65% or less of the total amount of diglyceride in the raw material palm-based fat and/or oil.
  4. The method of producing a refined palm-based fat and/or oil according to any one of claims 1 to 3, wherein the raw material palm-based fat and/or oil is pre-treated through a deodorizing step.
  5. The method of producing a refined palm-based fat and/or oil according to any one of claims 1 to 4, wherein the degree of vacuum in the thin-film distillation treatment is 1.0 Pa or less.
  6. The method of producing a refined palm-based fat and/or oil according to any one of claims 1 to 5, wherein the thin-film distillation treatment is short-path distillation treatment.
  7. The method of producing a refined palm-based fat and/or oil according to any one of claims 1 to 6, wherein an iodine value of the raw material palm-based fat and/or oil is less than 58.
  8. A method of reducing glycidol, 3-chloropropane-1,2-diol, and fatty acid esters thereof, and/or diglyceride in a refined palm-based fat and/or oil, the method comprising performing thin-film distillation treatment of a raw material palm-based fat and/or oil at a temperature condition of 155°C or more and 290°C or less.
EP17762978.9A 2016-03-11 2017-02-27 Method for producing refined palm-based fat/oil, and method for reducing glycidol, 3-chloropropane-1,2-diol and fatty acid esters thereof and/or diglycerides in refined palm-based fat/oil Active EP3428255B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2016047999 2016-03-11
PCT/JP2017/007478 WO2017154638A1 (en) 2016-03-11 2017-02-27 Method for producing refined palm-based fat/oil, and method for reducing glycidol, 3-chloropropane-1,2-diol and fatty acid esters thereof and/or diglycerides in refined palm-based fat/oil

Publications (3)

Publication Number Publication Date
EP3428255A1 true EP3428255A1 (en) 2019-01-16
EP3428255A4 EP3428255A4 (en) 2019-08-21
EP3428255B1 EP3428255B1 (en) 2022-03-30

Family

ID=59789201

Family Applications (1)

Application Number Title Priority Date Filing Date
EP17762978.9A Active EP3428255B1 (en) 2016-03-11 2017-02-27 Method for producing refined palm-based fat/oil, and method for reducing glycidol, 3-chloropropane-1,2-diol and fatty acid esters thereof and/or diglycerides in refined palm-based fat/oil

Country Status (4)

Country Link
EP (1) EP3428255B1 (en)
JP (1) JP6581715B2 (en)
MY (1) MY185581A (en)
WO (1) WO2017154638A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023122596A1 (en) * 2021-12-21 2023-06-29 Cargill, Incorporated Process for removing impurities from vegetable oil
EP4001384A4 (en) * 2019-07-17 2023-07-26 The Nisshin OilliO Group, Ltd. Method for producing refined fat/oil
US11814601B2 (en) 2017-11-02 2023-11-14 The Nisshin Oillio Group, Ltd. Method for reducing content of saturated hydrocarbon, and refined palm-based oils and/or fats

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2020003050A (en) * 2017-09-19 2020-07-27 Cargill Inc Infant food product.

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010248340A (en) * 2009-04-14 2010-11-04 Kaneka Corp Palm oil and fat, and method for producing the same
JP5700503B2 (en) * 2009-09-07 2015-04-15 日清オイリオグループ株式会社 Glyceride composition and method for producing the glyceride composition
JP6385634B2 (en) * 2011-11-30 2018-09-05 日清オイリオグループ株式会社 Oil and fat manufacturing method
KR101394644B1 (en) * 2012-05-22 2014-05-12 주식회사농심 Method for Preparing Low Bound 3-MCPD Edible Oil
WO2015057139A1 (en) * 2013-10-14 2015-04-23 Aak Ab Mitigation of 2-mcpd, 3-mcpd, esters therof and glycidyl esters in vegetable oil
CN105793403A (en) * 2013-11-14 2016-07-20 卡吉尔公司 Removal of unwanted propanol components

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11814601B2 (en) 2017-11-02 2023-11-14 The Nisshin Oillio Group, Ltd. Method for reducing content of saturated hydrocarbon, and refined palm-based oils and/or fats
EP4001384A4 (en) * 2019-07-17 2023-07-26 The Nisshin OilliO Group, Ltd. Method for producing refined fat/oil
WO2023122596A1 (en) * 2021-12-21 2023-06-29 Cargill, Incorporated Process for removing impurities from vegetable oil

Also Published As

Publication number Publication date
EP3428255A4 (en) 2019-08-21
WO2017154638A1 (en) 2017-09-14
MY185581A (en) 2021-05-23
EP3428255B1 (en) 2022-03-30
JPWO2017154638A1 (en) 2018-09-13
JP6581715B2 (en) 2019-09-25

Similar Documents

Publication Publication Date Title
EP3068854B2 (en) Removal of unwanted propanol components
EP3428255B1 (en) Method for producing refined palm-based fat/oil, and method for reducing glycidol, 3-chloropropane-1,2-diol and fatty acid esters thereof and/or diglycerides in refined palm-based fat/oil
US11814601B2 (en) Method for reducing content of saturated hydrocarbon, and refined palm-based oils and/or fats
US11891584B2 (en) Oils without unwanted contaminants
EP2471897A1 (en) Method for reducing chloropropanols and formative substance thereof, glycidol fatty acid esters, in glyceride oils
EP2891706A1 (en) Method for manufacturing refined oil or fat
JP5858712B2 (en) Method for producing thin film evaporation process fats and oils
WO2016113922A1 (en) Fat composition for use in infant formula
WO2013080648A1 (en) Method for producing fat or oil
WO2015146248A1 (en) Production method for purified palm oil and fat
KR101394644B1 (en) Method for Preparing Low Bound 3-MCPD Edible Oil
JPWO2017033674A1 (en) Method for producing soybean oil, method for producing mixed oil, and method for suppressing photopic odor of soybean oil
JP5924755B2 (en) Method for producing glyceride composition
EP3556833B1 (en) Method for producing fat/oil composition
JP7280731B2 (en) Method for producing refined fats and oils, and method for producing tocopherols
WO2018043701A1 (en) Fat composition for use in infant formula
WO2013018430A1 (en) Method for producing glyceride composition
WO2013145398A1 (en) Method for manufacturing glyceride composition and method for assessing necessity of second refining step for glyceride composition after first refining step

Legal Events

Date Code Title Description
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE

PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

17P Request for examination filed

Effective date: 20180903

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

DAV Request for validation of the european patent (deleted)
DAX Request for extension of the european patent (deleted)
A4 Supplementary search report drawn up and despatched

Effective date: 20190724

RIC1 Information provided on ipc code assigned before grant

Ipc: C11B 3/12 20060101AFI20190718BHEP

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: EXAMINATION IS IN PROGRESS

17Q First examination report despatched

Effective date: 20201112

TPAC Observations filed by third parties

Free format text: ORIGINAL CODE: EPIDOSNTIPA

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: GRANT OF PATENT IS INTENDED

TPAC Observations filed by third parties

Free format text: ORIGINAL CODE: EPIDOSNTIPA

INTG Intention to grant announced

Effective date: 20211028

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE PATENT HAS BEEN GRANTED

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

REG Reference to a national code

Ref country code: CH

Ref legal event code: EP

REG Reference to a national code

Ref country code: DE

Ref legal event code: R096

Ref document number: 602017055244

Country of ref document: DE

REG Reference to a national code

Ref country code: AT

Ref legal event code: REF

Ref document number: 1479204

Country of ref document: AT

Kind code of ref document: T

Effective date: 20220415

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

REG Reference to a national code

Ref country code: LT

Ref legal event code: MG9D

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220330

Ref country code: RS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220330

Ref country code: NO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220630

Ref country code: LT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220330

Ref country code: HR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220330

Ref country code: BG

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220630

REG Reference to a national code

Ref country code: NL

Ref legal event code: MP

Effective date: 20220330

REG Reference to a national code

Ref country code: AT

Ref legal event code: MK05

Ref document number: 1479204

Country of ref document: AT

Kind code of ref document: T

Effective date: 20220330

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LV

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220330

Ref country code: GR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220701

Ref country code: FI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220330

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220330

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SM

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220330

Ref country code: SK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220330

Ref country code: RO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220330

Ref country code: PT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220801

Ref country code: ES

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220330

Ref country code: EE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220330

Ref country code: CZ

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220330

Ref country code: AT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220330

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: PL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220330

Ref country code: IS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220730

Ref country code: AL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220330

REG Reference to a national code

Ref country code: DE

Ref legal event code: R026

Ref document number: 602017055244

Country of ref document: DE

PLBI Opposition filed

Free format text: ORIGINAL CODE: 0009260

PLAX Notice of opposition and request to file observation + time limit sent

Free format text: ORIGINAL CODE: EPIDOSNOBS2

26 Opposition filed

Opponent name: CARGILL, INCORPORATED

Effective date: 20221213

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220330

PLBB Reply of patent proprietor to notice(s) of opposition received

Free format text: ORIGINAL CODE: EPIDOSNOBS3

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220330

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MC

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20220330

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

REG Reference to a national code

Ref country code: BE

Ref legal event code: MM

Effective date: 20230228

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20230227

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20230227

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20230228

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20230228

REG Reference to a national code

Ref country code: IE

Ref legal event code: MM4A

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20230227

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20230227

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20230227

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20230228

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20240219

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: IT

Payment date: 20240228

Year of fee payment: 8

Ref country code: FR

Payment date: 20240222

Year of fee payment: 8