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WO2011081119A1 - Procédé permettant de réguler la production de chloropropanols et de substances formant du chloropropanol dans des huiles et des graisses de triglycérides - Google Patents

Procédé permettant de réguler la production de chloropropanols et de substances formant du chloropropanol dans des huiles et des graisses de triglycérides Download PDF

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Publication number
WO2011081119A1
WO2011081119A1 PCT/JP2010/073500 JP2010073500W WO2011081119A1 WO 2011081119 A1 WO2011081119 A1 WO 2011081119A1 JP 2010073500 W JP2010073500 W JP 2010073500W WO 2011081119 A1 WO2011081119 A1 WO 2011081119A1
Authority
WO
WIPO (PCT)
Prior art keywords
oil
fats
chloropropanols
glyceride
oils
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.)
Ceased
Application number
PCT/JP2010/073500
Other languages
English (en)
Japanese (ja)
Inventor
雅充 栗山
晴康 木田
仁美 尾森
太 横溝
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.)
Fuji Oil Co Ltd (fka Fuji Oil Holdings Inc)
Original Assignee
Fuji Oil Co 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
Application filed by Fuji Oil Co Ltd filed Critical Fuji Oil Co Ltd
Priority to JP2011547681A priority Critical patent/JPWO2011081119A1/ja
Publication of WO2011081119A1 publication Critical patent/WO2011081119A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • 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
    • C11B3/006—Refining fats or fatty oils by extraction
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
    • A23D9/02—Other edible oils or fats, e.g. shortenings or cooking oils characterised by the production or working-up
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment

Definitions

  • the present invention relates to a method for inhibiting the production of chloropropanols and their forming substances in glyceride oils and fats.
  • Chloropropanol is a general term for substances in which chlorine is bonded to propanol, but 3-chloropropanediol, which is one of these substances, has conventionally been produced in small quantities as a by-product when mainly producing amino acid solutions such as soy sauce. In addition, it is said that it is formed by the presence of lipids and salt in the process of cooking food.
  • Non-Patent Document 1 Korean Patent Document 1
  • Non-Patent Document 2 glycidol fatty acid esters are present as forming substances in the process of producing chloropropanols in glyceride oils.
  • An object of the present invention is to provide a method for suppressing the production of chloropropanols such as 3-chloropropanediol and 3-chloropropanediol fatty acid ester and glycidol fatty acid ester which is a forming substance thereof in glyceride fats and oils.
  • chloropropanols such as 3-chloropropanediol and 3-chloropropanediol fatty acid ester and glycidol fatty acid ester which is a forming substance thereof in glyceride fats and oils.
  • the inventors of the present invention increase the chloropropanols and their forming substances in glyceride fats and oils through a process in which the fats and oils are heated, such as decolorization and deodorization, based on causative substances present in trace amounts in glyceride fats and oils.
  • oil raw materials or glyceride fats and oils before heat treatment were mixed with a solvent in the presence of water, and the solvent was removed after separating the fats and solvent fractions.
  • the present invention (1) purifies the oil obtained by mixing the oil raw material or glyceride fat before heating with a solvent in the presence of water, separating the aqueous phase from the fat / solvent phase, and then removing the solvent.
  • the heat treatment is a step in which the oil raw material or the glyceride fat is heated to 200 ° C. or higher (1).
  • the solvent is a nonpolar solvent.
  • chloropropanols such as 3-chloropropanediol and 3-chloropropanediol fatty acid ester and glycidol fatty acid ester which is a forming substance thereof in glyceride oils and fats.
  • oil raw material used in the present invention examples include oil seeds such as soybean, rapeseed, sesame, safflower, cottonseed, peanut, rice bran, corn germ, or olive or palm oil.
  • examples of the glyceride fats and oils include soybean oil, rapeseed oil, sesame oil, safflower oil, cottonseed oil, peanut oil, or rice oil, corn oil, olive oil, and palm oil unrefined fat And crude oil and fat obtained by filtering and centrifuging unpurified oil and fat.
  • the glyceride fat used in the present invention is other than vegetable oils such as soybean oil, rapeseed oil, safflower oil, corn oil, sunflower oil, cottonseed oil, rice oil, olive oil, palm oil, coconut oil, palm kernel oil, sesame oil.
  • vegetable oils such as soybean oil, rapeseed oil, safflower oil, corn oil, sunflower oil, cottonseed oil, rice oil, olive oil, palm oil, coconut oil, palm kernel oil, sesame oil.
  • animal fats such as beef tallow, pork tallow and fish oil.
  • the method of the present invention can be carried out in a step of obtaining crude palm oil from oil palm pulp or a step before refining the crude palm oil.
  • the method of the present invention is characterized in that it is applied to oily raw materials or glyceride oils before heat treatment. This is based on the knowledge that causative substances present in oily raw materials or glyceride fats and oils are heated to change into chloropropanols and their forming substances. Therefore, in the method of the present invention, it is necessary that the causative substance present in the oily raw material or glyceride fat has a heating history that does not change to chloropropanols and their forming substances.
  • the oil raw material or glyceride oils and fats before the heat treatment It is important to apply to.
  • the heat treatment means heating to a high temperature at which the causative substance present in the oily raw material or glyceride fat is changed to chloropropanols and its forming substance as described above.
  • a heat treatment such as a step in which fats and oils are heated to 200 ° C. or higher can be exemplified. Therefore, by performing the method of the present invention before the refining process in which the oil raw material or glyceride fat is heated to 200 ° C. or higher, the production of chloropropanols and its forming substances in the glyceride fat can be suppressed.
  • the method of the present invention is characterized in that the oily raw material and glyceride oil / fat before heat treatment are mixed with a solvent in the presence of water to separate the aqueous phase from the oil / fat / solvent phase.
  • Chloropropanols in glyceride oils and glycidol fatty acid esters which are the substances that form them, are thought to be produced when oils and fats are heated to a high temperature with water-soluble substances such as chloride salts remaining in the oils and fats. .
  • water-soluble substances such as chloride salts in oil raw materials or glyceride fats and oils migrate to the water phase, and water-soluble substances can be removed from the oil / fat and solvent phases. Become.
  • the solvent used for mixing in the presence of water it is preferable to use a highly hydrophobic nonpolar solvent such as hexane in order to improve separation of the aqueous phase and the oil / fat / solvent phase.
  • a highly hydrophobic nonpolar solvent such as hexane
  • the present invention can also be carried out by mixing with a solvent in the presence of moisture contained in the oil raw material in the step of extracting oil from the oil raw material.
  • the amount of water required is 0.1% by weight or more, preferably 50% by weight or more, more preferably 200% by weight, based on the glyceride oil. If it is too small, removal of water-soluble substances in glyceride oils and fats to the aqueous phase tends to be insufficient. Further, the amount of the necessary solvent is 10% by weight or more, preferably 50% by weight or more, more preferably 200% by weight with respect to the glyceride oil.
  • the glyceride fats and oils obtained by the method of the present invention are difficult to produce chloropropanols and their forming substances, and it is possible to obtain purified fats and oils with a low content of chloropropanols and their forming substances by decolorizing and deodorizing. it can.
  • the glyceride fats and oils obtained by the method of the present invention have a reduced content of 3-chloropropanediol and 3-chloropropanediol fatty acid esters that are chloropropanols, and glycidol fatty acid esters that form the chloropropanols.
  • the content of propanols and glycidol fatty acid esters which are substances forming the propanols is measured by the following method with reference to the following literature. (Determination of total 3-chloropropane-1,2-diol (3-MCPD) in editable oils by cleavage of MCPD esters with sodium method. Eur. J. Lipid Sci.
  • 0.1 g of fat / oil is dissolved in 1 ml of t-butyl methyl ether, 250 ⁇ l of 20 ⁇ g / ml internal standard substance (3-MCPD-d 5 ethyl acetate solution) is added, and NaOCH 3 solution (0.5 mol / l NaOCH 3 in MeOH) is added. Mix with 1 ml and let stand at room temperature for 10 minutes. Subsequently, 3 ml of hexane, 3 ml of NaCl solution (NaCl 200 g / water 1 l) and 0.1 ml of glacial acetic acid are added, and after stirring, the upper layer is removed.
  • the upper layer is subjected to GS-MS analysis.
  • GC-MS is quantified using molecular ion peaks m / z 196 (3-MCPD) and m / z 201 (3-MCPD-d 5 ).
  • the above method is adopted as a method for measuring 3-chloropropanediol fatty acid ester and glycidol fatty acid ester, which is a forming substance, in Germany (Deutsche Gesellchaft fur Fettsch: DGF). Hydrolyzes 3-chloropropanediol fatty acid ester and its forming substance glycidol fatty acid ester in fats and oils, all 3-chloropropanediol fatty acid ester and its forming substance glycidol fatty acid ester as 3-MCPD Measuring. “With this method, another compounds forming 3-MCPD under the conditions of the anomalous areal and detected three-MCPD esters”. (Ester-bound 3-chloropropane-1,2-diol (3-MCPD esters) and 3-MCPD forming subnets: DGF Standard Methods Section C-Fats / C-III 18 (09))
  • % in an example means a basis of weight.
  • Comparative Example 2 The RBD palm oil obtained in Comparative Example 1 was decolorized at 2% by weight of white clay at 110 ° C. and 20 Torr for 10 minutes, and further deodorized at 250 ° C. and 2 Torr for 90 minutes. The content of chloropropanols and the substances forming the purified palm oil was 4.7 ppm.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Microbiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention porte sur un procédé qui permet de réguler la production de chloropropanols, tels que le 3-chloropropanediol et les esters d'acides gras 3-chloropropanediols, et de substances formant du chloropropanol dans des huiles et des graisses de triglycérides. Selon l'invention, on régule la production de chloropropanols, tels que le 3-chloropropanediol et les esters d'acides gras 3-chloropropanediols, et de substances formant du chloropropanol dans les huiles et les graisses en mélangeant des matières premières huiles comestibles non chauffées ou des huiles et des graisses de triglycérides en présence d'un solvant et d'eau, en séparant les fractions huiles et graisses des fractions solvant, en enlevant le solvant et en purifiant l'huile et la graisse obtenues.
PCT/JP2010/073500 2009-12-29 2010-12-27 Procédé permettant de réguler la production de chloropropanols et de substances formant du chloropropanol dans des huiles et des graisses de triglycérides Ceased WO2011081119A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2011547681A JPWO2011081119A1 (ja) 2009-12-29 2010-12-27 グリセリド油脂中のクロロプロパノール類及びその形成物質の生成を抑制する方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2009299021 2009-12-29
JP2009-299021 2009-12-29

Publications (1)

Publication Number Publication Date
WO2011081119A1 true WO2011081119A1 (fr) 2011-07-07

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PCT/JP2010/073500 Ceased WO2011081119A1 (fr) 2009-12-29 2010-12-27 Procédé permettant de réguler la production de chloropropanols et de substances formant du chloropropanol dans des huiles et des graisses de triglycérides

Country Status (2)

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JP (1) JPWO2011081119A1 (fr)
WO (1) WO2011081119A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013018412A1 (fr) * 2011-07-29 2013-02-07 日清オイリオグループ株式会社 Composition glycéridique purifiée et son procédé de production
JP2016169391A (ja) * 2011-07-29 2016-09-23 日清オイリオグループ株式会社 パーム系油脂

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06330080A (ja) * 1993-05-19 1994-11-29 Ueda Seiyu Kk 油脂中のコレステロール除去方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4139398C1 (fr) * 1991-11-29 1993-01-14 Siegfried Prof. Dr. 8525 Uttenreuth De Peter
JP2965525B2 (ja) * 1997-04-01 1999-10-18 協同組合エーオーツー 食用梅油およびその製造方法
JP2002294274A (ja) * 2001-03-29 2002-10-09 Nof Corp 高純度グリコシルセラミドおよびその製造方法
JP2006028466A (ja) * 2004-07-16 2006-02-02 Tsukishima Shokuhin Kogyo Kk 油脂の精製方法

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06330080A (ja) * 1993-05-19 1994-11-29 Ueda Seiyu Kk 油脂中のコレステロール除去方法

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
KUSTERS, M. ET AL.: "Rapid and Simple Micromethod for the Simultaneous Determination of 3-MCPD and 3-MCPD Esters in Different Foodstuffs", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 58, no. 11, 2010, pages 6570 - 6577 *
SVEJKOVSKA, B. ET AL.: "Formation and Decomposition of 3-Chloropropane-1,2-diol Esters in Models Simulating Processed Foods", CZECH JOURNAL OF FOOD SCIENCES, vol. 24, no. 4, 2006, pages 172 - 179 *
ZELINKOVA, Z. ET AL.: "Fatty acid esters of 3- chloropropane-1,2-diol in edible oils", FOOD ADDITIVES AND CONTAMINANTS, vol. 23, no. 12, 2006, pages 1290 - 1298, XP009125455, DOI: doi:10.1080/02652030600887628 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013018412A1 (fr) * 2011-07-29 2013-02-07 日清オイリオグループ株式会社 Composition glycéridique purifiée et son procédé de production
JP5216942B1 (ja) * 2011-07-29 2013-06-19 日清オイリオグループ株式会社 精製グリセリド組成物及び該精製グリセリド組成物の製造方法
JP2016169391A (ja) * 2011-07-29 2016-09-23 日清オイリオグループ株式会社 パーム系油脂

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