WO2012065790A1 - Method for producing refined vegetable oil - Google Patents

Method for producing refined vegetable oil Download PDF

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Publication number
WO2012065790A1
WO2012065790A1 PCT/EP2011/067816 EP2011067816W WO2012065790A1 WO 2012065790 A1 WO2012065790 A1 WO 2012065790A1 EP 2011067816 W EP2011067816 W EP 2011067816W WO 2012065790 A1 WO2012065790 A1 WO 2012065790A1
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WIPO (PCT)
Prior art keywords
oil
esters
ppm
less
chloropropane
Prior art date
Application number
PCT/EP2011/067816
Other languages
French (fr)
Inventor
Krishnadath Bhaggan
Jeanine Luvelle Werleman
Original Assignee
Loders Croklaan B.V.
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Application filed by Loders Croklaan B.V. filed Critical Loders Croklaan B.V.
Priority to US13/988,052 priority Critical patent/US20130302881A1/en
Priority to JP2013539179A priority patent/JP2014501808A/en
Priority to NZ610679A priority patent/NZ610679A/en
Priority to CN2011800551507A priority patent/CN103261386A/en
Priority to EP17204754.0A priority patent/EP3327105B1/en
Priority to CA2817992A priority patent/CA2817992C/en
Priority to DK11779116.0T priority patent/DK2640813T3/en
Priority to EP11779116.0A priority patent/EP2640813B1/en
Publication of WO2012065790A1 publication Critical patent/WO2012065790A1/en

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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
    • C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter
    • 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
    • C11B3/003—Refining fats or fatty oils by enzymes or microorganisms, living or dead
    • 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
    • C11B3/02—Refining fats or fatty oils by chemical reaction
    • C11B3/04—Refining fats or fatty oils by chemical reaction with acids
    • 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
    • C11B3/10—Refining fats or fatty oils by adsorption

Definitions

  • This invention relates to a method, in particular to a method for producing a refined vegetable oil. http://www.ilsi. org/Europe/Publications/Final%20version%203%20MCPD%20esters.p df discloses that certain foodstuffs may contain 3-chloropropane-1 ,2-diol (3-MCPD) and esters. Esters are typically esters of fatty acids, including C12-C24 straight chain, saturated or unsaturated carboxylic acids.
  • a method of producing a refined, bleached and deodorised vegetable oil which comprises degumming a vegetable oil, bleaching the degummed oil and deodorising the bleached oil, wherein the degumming, bleaching and deodorising conditions are selected to reduce the content of 3-chloropropane-1 ,2-diol and esters thereof in the deodorised oil to less than 8 ppm.
  • the invention provides a method of reducing the content of 3- chloropropane-1 ,2-diol and esters thereof of in a refined, bleached and deodorised vegetable oil, which comprises degumming a vegetable oil, bleaching the degummed oil and deodorising the bleached oil, wherein at least one of the degumming, bleaching and deodorising conditions are selected to reduce the content of 3- chloropropane-1 ,2-diol and esters thereof in the deodorised oil to less than 8 ppm.
  • the invention also provides a non-interesterified, refined, bleached, degummed and deodorised palm oil, or a fraction thereof, having a content of 3-chloropropane-1 ,2- diol and esters thereof of less than 8 ppm.
  • the invention provides a method for reducing the formation of 3- chloropropane-1 ,2-diol and esters thereof comprising: degumming a vegetable oil using a degumming agent comprising citric acid, bleaching the degummed oil in the presence of a natural bleaching agent, and deodorising the bleached oil at a temperature of less than 260 °C.
  • a further aspect of the invention is a process for reducing the levels of 3- chloropropane-1 ,2-diol and esters thereof in a vegetable oil, such as palm oil, which comprises treating the oil with a base.
  • Esters of 3-chloropropane-1 ,2-diol are typically esters of fatty acids, including C12- C24 straight chain saturated or unsaturated carboxylic acids.
  • the vegetable oil is typically an edible oil.
  • the vegetable oil comprises or is palm oil.
  • Palm oil, fractions of palm oil or blends of palm oil and/or its fractions may be used in the invention.
  • Oils derived from palm include palm oil, palm oil stearin, palm olein, palm kernel oil, palm kernel stearin and palm kernel olein and mixtures thereof.
  • the degumming is preferably carried out using a degumming agent comprising citric acid. More preferably, the degumming agent comprises a mixture of citric acid and phosphoric acid. The amount of phosphoric acid preferably ranges from 0 to 50% by weight based on total citric and phosphoric acids.
  • deodorisation is carried out at a temperature of less than 260 °C, more preferably at a temperature of from 180 °C to 255 °C, even more preferably from 200 °C to 250 °C.
  • a temperature of less than 260 °C more preferably at a temperature of from 180 °C to 255 °C, even more preferably from 200 °C to 250 °C.
  • General methods and apparatus for deodorising vegetable oils are well-known to those skilled in the art.
  • Bleaching is preferably carried out using a natural, non-activated bleaching agent.
  • the bleaching agent may comprise a mixture of a natural, non-activated bleaching agent and optionally an acid activated bleaching earth in an amount of up to 75% by weight of the total weight of bleaching agent.
  • Natural, non-activated bleaching agents are generally minerals occurring in nature that have not been chemically modified or treated, for example by activation with acid or alkali.
  • Preferred natural non-activated bleaching agents are clays, such as clays that have an intergrowth of two or more materials. More preferably, the natural non-activated bleaching agents are based on an intergrowth of hormite and smectite minerals.
  • Smectite clays include clays such as montmorillonite and bentonite. They have a layered or plate-like structure and are characterized by substitutions of metal ions within their structure, and are therefore electrically unbalanced.
  • Hormite or attapulgite is a magnesium aluminium silicate clay of very fine particle size with a chain instead of a sheet structure.
  • Natural non-activated bleaching agents that comprise an intergrowth of hormite and smectite minerals may be intermediate in structure between that of bentonite and attapulgite, with lamellae and tubules forming a three dimensional, porous network.
  • the method comprises: degumming a vegetable oil using a degumming agent comprising citric acid, optionally together with phosphoric acid,
  • the content of 3-chloropropane-1 ,2-diol and esters thereof in the deodorised oil produced by the methods and process of the invention is preferably reduced to less than 6 ppm, such as less than 5 ppm, or less than 4 ppm, or less than 3 ppm, or less than 2 ppm.
  • the method comprises: degumming a vegetable oil using a degumming agent comprising citric acid, optionally together with phosphoric acid,
  • deodorising the bleached oil at a temperature of less than 260 °C, wherein the oil is interesterified.
  • the method may comprise a step of treating the oil with a base, such as sodium hydroxide or sodium methoxide, to reduce the levels of 3-chloropropane-1 ,2-diol and esters thereof.
  • a base such as sodium hydroxide or sodium methoxide
  • the invention provides a process for reducing the levels of 3-chloropropane-1 ,2-diol and esters thereof in a vegetable oil, such as palm oil, which comprises treating the oil with a base.
  • Suitable bases include sodium hydroxide and sodium methoxide.
  • the oil produced by this process may be treated in the bleaching and/or deodorising steps of the methods of the invention i.e., bleaching the oil and/or deodorising the bleached oil, wherein the bleaching and/or deodorising conditions are selected to reduce the content of 3-chloropropane-1 ,2-diol and esters thereof in the deodorised oil to less than 8 ppm, preferably reduced to less than 6 ppm, such as less than 5 ppm, or less than 4 ppm, or less than 3 ppm, or less than 2 ppm.
  • the invention provides a process for reducing the levels of 3- chloropropane-1 ,2-diol and esters thereof in a vegetable oil, such as palm oil, which comprises treating the oil with an enzyme.
  • Suitable enzymes are lipases, for example Lipase G (from Pennicilium camembertii).
  • the oil produced by this process may be treated in the bleaching and/or deodorising steps of the methods of the invention i.e., bleaching the oil and/or deodorising the bleached oil, wherein the bleaching and/or deodorising conditions are selected to reduce the content of 3- chloropropane-1 ,2-diol and esters thereof in the deodorised oil to less than 8 ppm preferably reduced to less than 6 ppm, such as less than 5 ppm, or less than 4 ppm, or less than 3 ppm, or less than 2 ppm.
  • RBD PO contains 3- MCPD esters at level of higher than 10 ppm.
  • RBD PO 1200 gram of RBD PO is treated with 0.07% (wt) NaOMe (sodium methoxide) at 1 0°C and reduced pressure ( ⁇ 2 mbar), for 30 min. After this, water is added to the reaction mixture and any soap formed during the treatment is washed out. The almost soap-free oil is then bleached using standard bleaching conditions (1-1.5% bleaching earth at 90°C) and finally deodorized at 200°C for 4hrs. In the refined treated PO the level 3-MCPD esters is reduced to below 2 ppm.
  • NaOMe sodium methoxide
  • Palm Olein (POf IV 64; 16.8 ppm 3-MCPD's) is heated to 110°C while stirring at average speed.
  • the oil is then dried by applying vacuum and 0.1%(w/w) of NaOCH 3 is added.
  • the obtained reaction mixture is stirred under vacuum for an additional 30 minutes and the NaOCH 3 is deactivated by adding citric acid.
  • the treated oil is further refined by means of standard refining process.
  • the deodorization is carried out at lower temperature (180°C -210°C).
  • Example 3 Refining of cPO - effect of type of acid during dequmming cPO (crude Palm Oil) is physically refined according to the following conditions: 1 kg of cPO is heated to 105°C and 0.08%(w/w) of acid is added and stirred for 15 minutes at atmospheric pressure. After this, bleaching earth is added and the suspension is stirred under 100-250 mbar for 30 minutes. Hereafter, the oil is filtered and deodorized at 255°C for 4hrs.
  • Acid used for the degumming step - 75% H3PO4 solutions (Acid A)
  • Palm olein POf IV 64; 16.7 ppm 3-MCPD's
  • the temperature of the obtained emulsion is set to 40°C.
  • 0.05% (w/w) of Lipase G Pennicilium camembertii
  • the reaction mixture is settled and the water phase discharged.
  • the oil phase is washed with demineralized water in order to remove residual enzyme and dried after wards by applying vacuum.
  • the dried oil is further refined according to standard conditions.
  • the deodorization is carried out at lower temperature (200°C, 8 hours).

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Microbiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biochemistry (AREA)
  • Fats And Perfumes (AREA)
  • Edible Oils And Fats (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

A method of producing a refined, bleached and deodorised vegetable oil comprises degumming a vegetable oil, bleaching the degummed oil and deodorising the bleached oil, wherein the degumming, bleaching and deodorising conditions are selected to reduce the content of 3-chloropropane-1,2-diol and esters thereof in the deodorised oil to less than 8 ppm.

Description

METHOD FOR PRODUCING REFINED VEGETABLE OIL
This invention relates to a method, in particular to a method for producing a refined vegetable oil. http://www.ilsi. org/Europe/Publications/Final%20version%203%20MCPD%20esters.p df discloses that certain foodstuffs may contain 3-chloropropane-1 ,2-diol (3-MCPD) and esters. Esters are typically esters of fatty acids, including C12-C24 straight chain, saturated or unsaturated carboxylic acids.
There is a need to reduce or eliminate the presence of 3-MCPD and/or its esters in vegetable oils and foodstuffs containing them.
According to the invention, there is provided a method of producing a refined, bleached and deodorised vegetable oil which comprises degumming a vegetable oil, bleaching the degummed oil and deodorising the bleached oil, wherein the degumming, bleaching and deodorising conditions are selected to reduce the content of 3-chloropropane-1 ,2-diol and esters thereof in the deodorised oil to less than 8 ppm.
In another aspect, the invention provides a method of reducing the content of 3- chloropropane-1 ,2-diol and esters thereof of in a refined, bleached and deodorised vegetable oil, which comprises degumming a vegetable oil, bleaching the degummed oil and deodorising the bleached oil, wherein at least one of the degumming, bleaching and deodorising conditions are selected to reduce the content of 3- chloropropane-1 ,2-diol and esters thereof in the deodorised oil to less than 8 ppm.
The invention also provides a non-interesterified, refined, bleached, degummed and deodorised palm oil, or a fraction thereof, having a content of 3-chloropropane-1 ,2- diol and esters thereof of less than 8 ppm.
In another aspect, the invention provides a method for reducing the formation of 3- chloropropane-1 ,2-diol and esters thereof comprising: degumming a vegetable oil using a degumming agent comprising citric acid, bleaching the degummed oil in the presence of a natural bleaching agent, and deodorising the bleached oil at a temperature of less than 260 °C. A further aspect of the invention is a process for reducing the levels of 3- chloropropane-1 ,2-diol and esters thereof in a vegetable oil, such as palm oil, which comprises treating the oil with a base.
Esters of 3-chloropropane-1 ,2-diol are typically esters of fatty acids, including C12- C24 straight chain saturated or unsaturated carboxylic acids.
The vegetable oil is typically an edible oil. Preferably, the vegetable oil comprises or is palm oil. Palm oil, fractions of palm oil or blends of palm oil and/or its fractions may be used in the invention. Oils derived from palm include palm oil, palm oil stearin, palm olein, palm kernel oil, palm kernel stearin and palm kernel olein and mixtures thereof.
The degumming is preferably carried out using a degumming agent comprising citric acid. More preferably, the degumming agent comprises a mixture of citric acid and phosphoric acid. The amount of phosphoric acid preferably ranges from 0 to 50% by weight based on total citric and phosphoric acids.
Preferably, deodorisation is carried out at a temperature of less than 260 °C, more preferably at a temperature of from 180 °C to 255 °C, even more preferably from 200 °C to 250 °C. General methods and apparatus for deodorising vegetable oils are well-known to those skilled in the art.
Bleaching is preferably carried out using a natural, non-activated bleaching agent. The bleaching agent may comprise a mixture of a natural, non-activated bleaching agent and optionally an acid activated bleaching earth in an amount of up to 75% by weight of the total weight of bleaching agent.
Natural, non-activated bleaching agents are generally minerals occurring in nature that have not been chemically modified or treated, for example by activation with acid or alkali.
Preferred natural non-activated bleaching agents are clays, such as clays that have an intergrowth of two or more materials. More preferably, the natural non-activated bleaching agents are based on an intergrowth of hormite and smectite minerals. Smectite clays include clays such as montmorillonite and bentonite. They have a layered or plate-like structure and are characterized by substitutions of metal ions within their structure, and are therefore electrically unbalanced. Hormite or attapulgite is a magnesium aluminium silicate clay of very fine particle size with a chain instead of a sheet structure. Natural non-activated bleaching agents that comprise an intergrowth of hormite and smectite minerals may be intermediate in structure between that of bentonite and attapulgite, with lamellae and tubules forming a three dimensional, porous network.
Therefore, in one preferred embodiment, the method comprises: degumming a vegetable oil using a degumming agent comprising citric acid, optionally together with phosphoric acid,
bleaching the degummed oil in the presence of a natural, non-activated bleaching agent, and
deodorising the bleached oil at a temperature of less than 260 °C.
The content of 3-chloropropane-1 ,2-diol and esters thereof in the deodorised oil produced by the methods and process of the invention is preferably reduced to less than 6 ppm, such as less than 5 ppm, or less than 4 ppm, or less than 3 ppm, or less than 2 ppm.
Levels of 3-chloropropane-1 ,2-diol and esters thereof in the oils can be determined by the GC-MS method described in DGF Standard Methods at http://www.dgfett.de/methods/c-iii 18%20 09 e14.pdf.
Optionally, the oil is interesterified as part of the method. Interesterification may contribute to reducing the levels of 3-chloropropane-1 ,2-diol and esters thereof. The interesterification may be carried out in the presence of a base, such as sodium methoxide.
In another embodiment, the method comprises: degumming a vegetable oil using a degumming agent comprising citric acid, optionally together with phosphoric acid,
bleaching the degummed oil, preferably in the presence of a natural, non- activated bleaching agent, and
deodorising the bleached oil at a temperature of less than 260 °C, wherein the oil is interesterified.
The method may comprise a step of treating the oil with a base, such as sodium hydroxide or sodium methoxide, to reduce the levels of 3-chloropropane-1 ,2-diol and esters thereof.
In another aspect, therefore, the invention provides a process for reducing the levels of 3-chloropropane-1 ,2-diol and esters thereof in a vegetable oil, such as palm oil, which comprises treating the oil with a base. Suitable bases include sodium hydroxide and sodium methoxide. The oil produced by this process may be treated in the bleaching and/or deodorising steps of the methods of the invention i.e., bleaching the oil and/or deodorising the bleached oil, wherein the bleaching and/or deodorising conditions are selected to reduce the content of 3-chloropropane-1 ,2-diol and esters thereof in the deodorised oil to less than 8 ppm, preferably reduced to less than 6 ppm, such as less than 5 ppm, or less than 4 ppm, or less than 3 ppm, or less than 2 ppm.
In a further aspect the invention provides a process for reducing the levels of 3- chloropropane-1 ,2-diol and esters thereof in a vegetable oil, such as palm oil, which comprises treating the oil with an enzyme. Suitable enzymes are lipases, for example Lipase G (from Pennicilium camembertii). The oil produced by this process may be treated in the bleaching and/or deodorising steps of the methods of the invention i.e., bleaching the oil and/or deodorising the bleached oil, wherein the bleaching and/or deodorising conditions are selected to reduce the content of 3- chloropropane-1 ,2-diol and esters thereof in the deodorised oil to less than 8 ppm preferably reduced to less than 6 ppm, such as less than 5 ppm, or less than 4 ppm, or less than 3 ppm, or less than 2 ppm.
The following non-limiting examples illustrate the invention and do not limit its scope in any way. In the examples and throughout this specification, all percentages, parts and ratios are by weight unless indicated otherwise. Examples
Example 1
Crude palm oil is physically refined using standard refining conditions to obtain RBD (R = refined; B = bleached; D = deodorized) palm oil (PO). The RBD PO contains 3- MCPD esters at level of higher than 10 ppm.
1200 gram of RBD PO is treated with 0.07% (wt) NaOMe (sodium methoxide) at 1 0°C and reduced pressure (< 2 mbar), for 30 min. After this, water is added to the reaction mixture and any soap formed during the treatment is washed out. The almost soap-free oil is then bleached using standard bleaching conditions (1-1.5% bleaching earth at 90°C) and finally deodorized at 200°C for 4hrs. In the refined treated PO the level 3-MCPD esters is reduced to below 2 ppm.
Example 2
1 kg of Palm Olein (POf IV 64; 16.8 ppm 3-MCPD's) is heated to 110°C while stirring at average speed. The oil is then dried by applying vacuum and 0.1%(w/w) of NaOCH3 is added. The obtained reaction mixture is stirred under vacuum for an additional 30 minutes and the NaOCH3 is deactivated by adding citric acid. The treated oil is further refined by means of standard refining process. The deodorization is carried out at lower temperature (180°C -210°C).
By this treatment about 75% of the 3-MCPD esters are reduced to give a level of
2 ppm
Example 3: Refining of cPO - effect of type of acid during dequmming cPO (crude Palm Oil) is physically refined according to the following conditions: 1 kg of cPO is heated to 105°C and 0.08%(w/w) of acid is added and stirred for 15 minutes at atmospheric pressure. After this, bleaching earth is added and the suspension is stirred under 100-250 mbar for 30 minutes. Hereafter, the oil is filtered and deodorized at 255°C for 4hrs.
Acid used for the degumming step: - 75% H3PO4 solutions (Acid A)
- 50% Citric acid solution (Acid B)
By using Acid B in the degumming step a reduction of formation of 14% of 3-MCPD esters is achieved (7.9 ppm 3-MCPD's) instead of using Acid A (9 ppm 3-MCPD's).
Example 4. Reduction of 3-MCPD esters by enzymatic treatment
To 1 kg of Palm olein (POf IV 64; 16.7 ppm 3-MCPD's) is added 25%(w/w) of demineralized water and the temperature of the obtained emulsion is set to 40°C. To this emulsion is added 0.05% (w/w) of Lipase G (Pennicilium camembertii) and the mixture is stirred for 24 hours. After this the temperature is increased to 80°C in order to deactivate the enzyme. The reaction mixture is settled and the water phase discharged. The oil phase is washed with demineralized water in order to remove residual enzyme and dried after wards by applying vacuum.
The dried oil is further refined according to standard conditions. The deodorization is carried out at lower temperature (200°C, 8 hours).
By this process the 3-MCPD ester content is reduced to 1.9 ppm.

Claims

1. A method of producing a refined, bleached and deodorised vegetable oil which comprises degumming a vegetable oil, bleaching the degummed oil and deodorising the bleached oil, wherein the degumming, bleaching and deodorising conditions are selected to reduce the content of 3-chloropropane-1 ,2-diol and esters thereof in the deodorised oil to less than 8 ppm.
2. A method of reducing the content of 3-chloropropane-1,2-diol and esters thereof of in a refined, bleached and deodorised vegetable oil, which comprises degumming a vegetable oil, bleaching the degummed oil and deodorising the bleached oil, wherein at least one of the degumming, bleaching and deodorising conditions are selected to reduce the content of 3-chloropropane-1 ,2-diol and esters thereof in the deodorised oil to less than 8 ppm.
3. Method as claimed in Claim 1 or Claim 2, wherein the vegetable oil comprises palm oil or a fraction thereof.
4. Method as claimed in any one of the preceding claims, wherein the degumming is carried out using a degumming agent comprising citric acid.
5. Method as claimed in Claim 4, wherein the degumming agent comprises a mixture of citric acid and phosphoric acid.
6. Method as claimed in any one of the preceding claims, wherein deodorisation is carried out at a temperature of less than 260 °C.
7. Method as claimed in any one of the preceding claims, wherein deodorisation is carried out at a temperature of from 180 °C to 255 °C.
8. Method as claimed in any one of the preceding claims, wherein bleaching is carried out using a natural, non-activated bleaching agent.
9. Method as claimed in any one of the preceding claims, wherein the content of 3-chloropropane-1 ,2-diol and esters thereof in the deodorised oil is reduced to less than 4 ppm.
10. Method as claimed in any one of the preceding claims, wherein the content of 3-chloropropane-1 ,2-diol and esters thereof in the deodorised oil is reduced to less than 2 ppm.
11. Non-interesterified, refined, bleached, degummed and deodorised palm oil, or a fraction thereof, having a content of 3-chloropropane-1 ,2-diol and esters thereof of less than 8 ppm.
12. Palm oil or fraction thereof as claimed in Claim 11 having a content of 3- chloropropane-1 ,2-diol and esters thereof of less than 4 ppm.
13. Palm oil or fraction thereof as claimed in Claim 11 having a content of 3- chloropropane-1 ,2-diol and esters thereof of less than 2 ppm.
14. Food product comprising a palm oil or fraction thereof according to any one of Claims 11 to 13.
PCT/EP2011/067816 2010-11-19 2011-10-12 Method for producing refined vegetable oil WO2012065790A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
US13/988,052 US20130302881A1 (en) 2010-11-19 2011-10-12 Method for producing refined vegetable oil
JP2013539179A JP2014501808A (en) 2010-11-19 2011-10-12 Process for producing refined vegetable oil
NZ610679A NZ610679A (en) 2010-11-19 2011-10-12 Method for producing refined vegetable oil
CN2011800551507A CN103261386A (en) 2010-11-19 2011-10-12 Method for producing refined vegetable oil
EP17204754.0A EP3327105B1 (en) 2010-11-19 2011-10-12 Process for producing refined vegetable oil
CA2817992A CA2817992C (en) 2010-11-19 2011-10-12 Method for producing refined vegetable oil
DK11779116.0T DK2640813T3 (en) 2010-11-19 2011-10-12 Method for producing refined vegetable oil
EP11779116.0A EP2640813B1 (en) 2010-11-19 2011-10-12 Method for producing refined vegetable oil

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GBGB1019639.2A GB201019639D0 (en) 2010-11-19 2010-11-19 Method
GB1019639.2 2010-11-19

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EP (3) EP2640813B1 (en)
JP (1) JP2014501808A (en)
CN (1) CN103261386A (en)
CA (1) CA2817992C (en)
DK (3) DK3070154T3 (en)
ES (1) ES2773789T3 (en)
GB (1) GB201019639D0 (en)
NZ (1) NZ610679A (en)
WO (1) WO2012065790A1 (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013093093A1 (en) 2011-12-23 2013-06-27 Loders Croklaan B.V. Method of treating a vegetable oil
WO2014012548A1 (en) * 2012-07-18 2014-01-23 Aarhuskarlshamn Ab Reduction of mcpd-compounds in refined plant oil for food
EP2640813B1 (en) 2010-11-19 2016-06-01 Loders Croklaan B.V. Method for producing refined vegetable oil
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WO2019007918A1 (en) 2017-07-07 2019-01-10 Bunge Loders Croklaan B.V. Process for the preparation of a hydrogenated fat composition
WO2019139533A1 (en) * 2018-01-09 2019-07-18 Aak Ab Physical refining process for palm oil
EP3385360B1 (en) 2011-02-10 2021-03-31 Cargill, Incorporated Process for reducing the 3-mcpd content in refined oils

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6467134B2 (en) * 2014-01-31 2019-02-06 花王株式会社 Oil composition
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WO2021262466A1 (en) * 2020-06-24 2021-12-30 Cargill, Incorporated Oil processing
US11992822B2 (en) 2021-07-19 2024-05-28 Active Minerals International, Llc Thermally activated bleaching clay product for oil bleaching

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0936266A1 (en) * 1998-02-13 1999-08-18 Lipidia Holding S.A. Refining of edible oil retaining maximum antioxidative potency

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS54111507A (en) * 1978-02-17 1979-08-31 Kiyadobarii Indeia Ltd Method of degumming fatty acid glyceride
BE1007151A3 (en) * 1993-06-18 1995-04-11 Tirtiaux Fractionnement Degumming method of fats and fats obtained.
US7226771B2 (en) * 2002-04-19 2007-06-05 Diversa Corporation Phospholipases, nucleic acids encoding them and methods for making and using them
CN1737094A (en) * 2004-08-17 2006-02-22 王朝阳 Edible oil continuous filtration fining process
SE530258C2 (en) * 2006-02-15 2008-04-15 Alfa Laval Corp Ab A process for refining fats and oils
ES2671172T3 (en) 2007-02-28 2018-06-05 Loders Croklaan B.V. Process to produce a glyceride composition
JP4249250B1 (en) * 2008-07-31 2009-04-02 水澤化学工業株式会社 Method for refining transesterified oil
JPWO2010050449A1 (en) 2008-10-28 2012-03-29 日清オイリオグループ株式会社 Palm oil, deodorized distillate and method for producing them
DE102008060059A1 (en) 2008-12-02 2010-06-10 Süd-Chemie AG Method for reducing the 3-MCPD content in refined vegetable oils
JPWO2010126136A1 (en) 2009-04-30 2012-11-01 不二製油株式会社 Method for inhibiting the formation of chloropropanols and their forming substances in glyceride oils
JPWO2011055732A1 (en) * 2009-11-06 2013-03-28 不二製油株式会社 Method for reducing chloropropanols and substances formed in glyceride oils and fats
AU2010325890A1 (en) 2009-12-04 2012-06-07 Archer Daniels Midland Company Glycidyl ester reduction in oil
JP2011144343A (en) * 2009-12-15 2011-07-28 Kao Corp Manufacturing method of refined oil and fat
IN2012DN05212A (en) 2009-12-15 2015-10-23 Kao Corp
JP5706094B2 (en) * 2010-03-31 2015-04-22 花王株式会社 Oil composition
CN102334563B (en) * 2010-07-16 2015-03-25 丰益(上海)生物技术研发中心有限公司 Method for controlling content of 3-chloro-1,2-propanediol or ester thereof in oil
GB201019639D0 (en) 2010-11-19 2010-12-29 Loders Croklaan Bv Method

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0936266A1 (en) * 1998-02-13 1999-08-18 Lipidia Holding S.A. Refining of edible oil retaining maximum antioxidative potency

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
FRANKE K ET AL: "Influence of chemical refining process and oil type on bound 3-chloro-1,2-propanediol contents in palm oil and rapeseed oil", LWT- FOOD SCIENCE AND TECHNOLOGY, ACADEMIC PRESS, UNITED KINGDOM, vol. 42, no. 10, 1 December 2009 (2009-12-01), pages 1751 - 1754, XP026502436, ISSN: 0023-6438, [retrieved on 20090527], DOI: 10.1016/J.LWT.2009.05.021 *
ZUZANA ZELINKOVÃ Â ET AL: "Occurrence of 3-chloropropane-1,2-diol fatty acid esters in infant and baby foods", EUROPEAN FOOD RESEARCH AND TECHNOLOGY ; ZEITSCHRIFT FÜR LEBENSMITTELUNTERSUCHUNG UND -FORSCHUNG A, SPRINGER, BERLIN, DE, vol. 228, no. 4, 15 October 2008 (2008-10-15), pages 571 - 578, XP019702891, ISSN: 1438-2385 *

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