WO2013163112A1 - Procédés perfectionnés de fractionnement - Google Patents

Procédés perfectionnés de fractionnement Download PDF

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Publication number
WO2013163112A1
WO2013163112A1 PCT/US2013/037678 US2013037678W WO2013163112A1 WO 2013163112 A1 WO2013163112 A1 WO 2013163112A1 US 2013037678 W US2013037678 W US 2013037678W WO 2013163112 A1 WO2013163112 A1 WO 2013163112A1
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Prior art keywords
palm oil
palm
oil
fraction
fractionation
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PCT/US2013/037678
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English (en)
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Nils HINRICHSEN
Phil Hogan
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Archer Daniels Midland Company
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Publication of WO2013163112A1 publication Critical patent/WO2013163112A1/fr

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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
    • C11B3/02—Refining fats or fatty oils by chemical reaction
    • C11B3/06—Refining fats or fatty oils by chemical reaction with bases
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
    • 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

  • the present approach relates to methods for producing fats and oils. Specifically, the present approach pertains to methods for producing fractions of palm oil having low levels of monochSoropropanediol contaminants and glycido! ester contaminants and methods for making the fractions.
  • the content of GE and MCPD in crude palm oil before physical refining is typically low, and may be below defection limits.
  • the exposure of oil to the elevated temperatures and/or long treatment times used in the physical refining process used to remove free fatty acids from palm oil problematically results in the formation of MCPD,
  • the level of MCPD in palm oil after physical refining is typically 1-5 ppm. but may be much higher.
  • MCPD concentrates MCPD in the more liquid fraction, called an "olein" fraction.
  • additional fractionation steps such as second stage, third stage, and fourth stage fractionations can concentrate the MCPD in further olein fractions, such as second oiein and third oiein fractions.
  • Palm oil fractions frequently require bleaching and deodorization.
  • the deodorization process is similar to the physical refining process, and in deodorization the palm fractions are subjected to further temperature stress.
  • the content of GE and MCPD and i paim fractions frequently increases further during bleaching and deodorization.
  • Palm oil fractions such as palm olein, have been categorize as food oils having high levels (greater than 4 mg/kg) of MCPD (Larsen, J. C, "3-MCPD Esters in Food Products/' Summary Report of a Workshop held in February 2009 in Brussels, Belgium, International Life Sciences Institute).
  • MCPD than are available by conventional physical refining of paim oil.
  • Figure 1 shows a scheme for selected methods of palm oil
  • Fraction names and Iodine values (IV) are not limiting but are typical of some grades of fractions.
  • Figure 2 shows a scheme for a method of palm oil fractionation described in Example 5.
  • Fraction names and Iodine values (IV) are not limiting but are typical of some grades of fractions.
  • the present approach relates to producing compositions of palm oil fractions having low levels of GE and CPD contaminants.
  • Crude oi means unprocessed oil after it has been extracted from vegetable or animal raw materia!. Crude oils normally need refining to render them fit for human consumption.
  • deodorization means steam distillation of refined oil to remove impurities.
  • oils include but are not limited to soybean oil, canoSa oil, corn oil, sunflower oil, palm oil, palm kernel oil, and saffiower oil, and fractions of any thereof.
  • alkali refining means removing free fatty acids from oil by contacting with a solutio of alkali and removal of resulting fatty acid soaps that form from the bulk of triaeySglyceroSs.
  • Alkali refined oil may be, but not always, subsequently bleached and deodorized before being considered to be edible grade.
  • physical refining means high temperature steam distillation of oil under conditions which remove most free fatty acids while keeping the bulk of triacylgl cerols intact. Physical refining is similar to deodorization, except physical refining is often carried out to remove free fatty acids in addition to the impurities removed by deodorization. Physical refining is typically carried out at temperatures of 240- 270 °C.
  • palm fraction means a component of palm oil obtained from fractionation of palm oil.
  • fractionation means a physical separation process applied to fats or oils resulting in fractions of the fat or oil having different
  • compositions include by cooling under defined conditions until a solid forms. Further filtration or decanting of the cooled fat results in fat being split into at least a low melting liquid fraction ⁇ olein) and a higher-melting solid fraction (stearin). Fractionation can take place in the absence (dry fractionation) or presence (wet fractionation) of an additional solvent, such as acetone, liquid vegetable oil, or hexane. Fractionation is carried out by cooling oil until crystals form (stearin), then filtering the cooled oil to separate the liquid olein from the stearin crystals.
  • the stearin crystals ma retain liquid olein in the interstitial space in and among crystals, and stearin ma be subjected to pressing to remove the retained olein.
  • Fractionation parameters include the rate of cooling, the final cooling temperature, the duration of holding at a given temperature, the diameters and distribution of perforations in filter screens, and the amount and duration of pressure that is optionally applied to stearin.
  • the temperatures and pressures needed for fractionation are varied according to the properties of the starting materials and desired products according to procedures widely known to those of the art.
  • Olein and stearin refer to the two fractions obtained in a fractionation step.
  • Olein refers to the fraction having a higher iodine value and “stearin” refers to the fraction having a lower iodine value.
  • Olein fractions are enriched in oil components having a lower melting point than either the unfractionated oil or the stearin fraction and are thus softer that the corresponding stearin fraction.
  • Olein is predominantly liquid oil at a fractionation temperature, and stearin is predominantly solid oil at fractionaiton temperatures.
  • Generaily the iodine value of an olein fraciion is higher than the iodine value of the.
  • palm stearin means a palm fraction enriched in palm oil components having a higher melting point than the unfractionated palm oil from which it was obtained, or ⁇ is predominantly solid oii at the filtration temperature.
  • the iodine value of a stearin fraction is lower than the iodine value of the oil or fraction from which it was derived.
  • the yields of olein and stearin from a given filtration step can be varied within relatively broad ranges.
  • the yield of stearin can comprise 10- 90 weight percent of the starting material; the corresponding yield of olein will comprise 90- 10 weight percent of the starting material, so that the weights of the stearin and olein will sum to approximately the weight of the starting material.
  • Each olein or stearin fraction can be designated with a number indicating the iodine value of the fraction. Palm fractionators often develop their own unique terminology for each fraction. However, regardless of any other names ascribed to a fraction, the question of which fraction from a fractionation step is the stearin or the olein can be answered by comparing their iodine values.
  • first stage fractionation or “primary fractionation” means fractionation of an oil that has not been previously subjected to a fractionation step.
  • a stearin fraction and an olein fraction are obtained. Palm fractionators often refer to the first olein as “palm olein” and the first stearin as “hard stearin.”
  • palm olein or “first olein” refer to the olein fraction obtained in a first fractionation.
  • hard stearin or “first stearin” refer to the stearin obtained in a first stage fractionation of palm oil.
  • a first olein obtained in first stage fractionation first oiein may have an IV of 56 and can thus be denoted “oiein 56.”
  • the corresponding stearin may have an IV of 33 and can thus be denoted "stearin 33.”
  • fractionation means fractionation of a first oiein fraction or a first stearin fraction that has been obtained in a first fractionation step.
  • first oiein (palm o!ein) from first stage fractionation can be fractionated in a second stage fractionation to form a second oiein fraction and a second stearin fraction.
  • double fractionated oiein means a second oiein resulting from the second stage fractionation of a first oiein.
  • Second oiein is enriched in unsaturated oils relative to first oiein, and the iodine value of doub!e fractionated oiein (second oiein) is higher than the iodine va!ue of the palm oiein ⁇ first oiein) from which it was derived.
  • Second oiein may also be called “super oiein,” or “double oiein,” and may have an iodine value of 64, in which case it may be called “oiein 64" or "olein(64)".
  • second stearin is enriched in saturated oils relative to first oiein, and the iodine value of second stearin is lower than the iodine value of both the first oiein from which it was derived and the second oiein.
  • Second stearin may also be cailed "soft PMF,” “soft palm mid fraction” or “sPMF” and may have an !V of 45, in which case it may be called "sP F(45)".
  • third stage fractionation means fractionation of a fraction that has bee obtained in a second fractionation step, such as a second stearin or a second oiein.
  • a second stearin resulting from second stage fractionation is subjected to third stage fractionation, the resulting oiein is called “third oiein.”
  • a third oiein having an iodine value of 49 may be called
  • a third stearin is also formed in third stage fractionation; for example, a third stearin having an iodine value of 30 may be called “hard palm mid fraction (30).”
  • fourth stage fractionation means fractionation of a third oiein or third stearin that has been obtained in a third fractionation step.
  • a third oiein such as PMF(49)
  • the resulting fourth oiein fraction having an iodine value of 54 is called “oiein fiussig(54)”
  • the resulting fourth stearin fraction having an iodine value of 39 is called “palm mid fraction ⁇ 39)" or H P F ⁇ 39)”.
  • MCPD is a contaminant that occurs in food in its non-esterified (diol) form
  • MCPD esters means a monoester or diester (with fatty acids) of MCPD, MCPD esters are contaminants that occur in food in an esterified (with fatty acids) form.
  • glycidol ester refers to a fatty acid ester of giycidol. Giycidol esters are contaminants that occur in food in an esterified (with fatty acids) form.
  • iodine value refers to a measure of the unsaturation of fats and oils and is expressed in terms of the number of centigrams of iodine absorbed per gram of sample (% iodine absorbed). Higher iodine values indicate a more liquid fraction having a greater degree of unsaturation (greater number of double bonds).
  • One non-limiting aspect of the present disclosure is directed to a composition comprising a palm oi! fraction, wherein the palm oil fraction contains less than two parts per million of at least one of a MCPD or a GE, less than 1.5 parts per million of at least one of a MCPD or a GE, less than one part per million of at least one of a MCPD or a GE, less than 0.5 parts per million of at least one of a MCPD or a GE, less than 0.1 parts per million of at least one of a MCPD or a GE, or is below the limit of detection of a detection method.
  • the detection is carried out according to a method selected from the group consisting of the 3 ⁇ in ⁇ 1 method of SGS Hamburg and the DGF Standard Method C-fV 18 (10).
  • the palm oil fractions are produced from a starting palm oil containing greater than 1.5% free fatty acids.
  • One non-limiting aspect of the present disclosure is directed to the palm oil fractions produced by alkali refining palm oil to obtain refined palm oil, and fractionating the refined palm oil in one or more fractionation steps to obtain two or more palm fractions.
  • the refined oil is produced by subjecting the oil to acid treatment before alkali refining.
  • fractions may be bleached.
  • One non-limiting aspect of the present disclosure is directed to a deodorized palm oil fraction, wherein the deodorized palm oil fraction contains less than two parts per million of at least one of a MCPD or a GE, less than 1.5 parts per million of at least one of a MCPD or a GE, less than one part per million of at least one of a MCPD or a GE, less than 0,5 parts per million of at least one of a MCPD or a GE, less than 0.1 parts per million of at least one of a MCPD or a GE,
  • One non- limiting aspect of the present disclosure is directed to deodorized palm oil fraction wherein at least one of a MCPD or a GE of the deodorized palm oil fraction is below detection limits of a detection method.
  • the detection is carried out according to a method selected from the group consisting of the 3 ⁇ in ⁇ 1 method of SGS Hamburg and the DGF Standard Method C-iV 18 (10).
  • the deodorized palm fraction comprises a fraction resulting from at least one of a first stage fractionation, a second stage fractionation, a third stage fractionation, and a fourth stage
  • One non-limiting aspect of the present disclosure is directed to deodorized palm oil fraction wherein the deodorized paim fraction comprises a palm mid fraction resulting from fourth stage fractionation of palm oil.
  • One non-limiting aspect of the present disclosure is directed to a method of producing palm oil fractions wherein a starting palm oil is alkali refined (chemically refined) to obtain refined palm oil, and fractionated in one or more fractionation steps to obtain two or more palm fractions, such as palm olein and palm stearin, wherein the level of MCPD in the palm fractions is less than one part per million or the level of GE in the palm fractions is less than one part per million.
  • the starting palm oil may contain greater than 1.5% free fatty acids before alkali refining.
  • the refined oil is produced by subjecting the oil to acid treatment before alkali refining
  • paim fractions may be subjected to further fractionation, forming further fractions reduced in a MCPD, such as hard stearin, super stearin, soft stearin, soft palm mid fraction, super olein, hard palm mid fraction, oieins, top o!ein, stearin(33), hard stearin(35), olein(56), palm olein(56), olein(64), super olein(64), sPMF(45), soft PMF(45), super stearin (40), PMF(49), hard palm mid fraction(30), PMF ⁇ 30), olein flussig(54) !
  • a MCPD such as hard stearin, super stearin, soft stearin, soft palm mid fraction, super olein, hard palm mid fraction, oieins, top o!ein, stearin(33),
  • the level of a MCPD in these further palm fractions is less than two parts per million of at least one of a MCPD or a GE, less than ,5 parts per million of at least one of a MCPD or a GE, less than one part per million of at least one of a MCPD or a GE, less than 0.5 parts per million of at least one of a MCPD, and iess than 0.1 parts per million of at least one of a MCPD.
  • One non-iimiting aspect of the present disclosure is directed to deodorized paim oil fraction wherein at least one of a MCPD or a GE of the deodorized paim oil fraction is below detection limits of a detection method.
  • any of these fractions may be further subjected to bleaching, deodorizing, or bleaching and deodorizing to obtain bleached, deodorized, or bleached and deodorized paim fractions.
  • the MCPD levels of the bleached, deodorized, or bleached and deodorized palm fractions may be iess than two parts per million of at least one of a MCPD or a GE, less than 1.5 parts per million of at ieast one of a MCPD or a GE, less than one part per million of at least one of a MCPD or a GE, less than 0.5 parts per million of at ieast one of a MCPD, and iess than 0,1 parts per million of at Ieast one of a MCPD.
  • One non-limiting aspect of the present disciosure is directed to deodorized palm oil fraction wherein at least one of a MCPD or a GE of the
  • deodorized palm oil fraction is below detection limits of a detection method, including the 3-in-1 method of SGS Hamburg, Germany and the DGF Standard Method C-iV 18 (10).
  • products may be obtained by the methods outlined herein, and products obtained by the methods outlined herein may be used, for example in food fat, food ingredients, frying oil, blending oil, biscuits, bakery, cookies, margarine, fried foods, shortenings, infant formulas, chocolate spreads, confectioneries, coffee whitener, filled miik, biscuit cream, cookie cream, and coating fats.
  • Residence time in the deodorizer was 60 minutes. After cooling, physically refined palm oil was obtained.
  • fractionation of physically-refined palm oil was carried out in a one-iiter jacketed vessel equipped with an overhead double-paddie scraped-surface stirrer operated at 3 RPM.
  • the temperature of the palm oil was controlled using a circulating cooling bath to circulate cold water through the jacket of the vessel.
  • the temperature of the fat in the vessel was monitored with a calibrated temperature probe.
  • Physicaliy- refined palm oil was heated to 62X and homogenized, and 800 grams of the palm oil was added to the fractionating batch vessel. The vessel temperature was set to 55 C C.
  • the physicaf!y-refined palm oil was subjected to the procedure outlined in Table 1. Table 1.
  • Table 1 First stage fractionation procedure, _
  • palm fractions (28.5 weight percent palm stearin and 71.5 weight percent palm olein).
  • the palm stearin and palm olein were separately bleached with 1 % clay at 70 °C and deodorized.
  • the levels of 3-MCPD, 2-MCPD, and GE were determined by during the process using the DGF Standard Method "3 ⁇ in-1 method," SGS Germany GmbH, Hamburg, Germany (Table 3).
  • the starting palm oil contained 5.4% free fatty acids, and the free fatty acid level after alkali refining was substantially reduced.
  • starting palm oil was alkali refined to obtain palm stearin and palm olein having MCPD levels of less than one part per million of 3- MCPD and 2-MCPD and GE before bleaching, after bieaching. in fact, the levels of 2- MCPD, 3-MCPD and GE were below the detection limits of the detection method.
  • bleached and deodorized palm oil fractions containing less than one part per million of MCPD and less than one part per million GE were obtained.
  • the bleached and deodorized first olein contained less than one part per million of MCPD and the level of GE of the first olein was below the detection limit of the 3-in-1 method of SGS Hamburg, Germany.
  • Palm fractions containing less than one part per million of MCPD and less than one part per million GE were obtained.
  • the levels of 3-MCPD, 2-GE and MCPDs in palm stearin and palm olein obtained by first stage fractionation of alkali- refined palm oil were at or below the detection limits of the DGF Standard Method "3- in-1 method.”
  • the levels of GE and MCPD after subsequent deodorizaiion of the palm stearin and palm olein are expected to be less than one part per million of MCPD as demonstrated in Example 2 (Table 3).
  • the cooled first olein was vacuum filtered through black ribbon filter paper (12 - 25 microns) at room temperature to obtain palm fractions.
  • a second stearin fraction (soft PMF(55), 69 weight percent) and a second olein fraction (double fractionated olein(59), 31 weight percent were obtained.
  • the iodine value and levels of MCPD and GE were determined (Table 7).
  • Palm fractions containing less than one part per million of MCPD and less than one part per million GE were obtained.
  • the second stearin fraction (soft PMF ⁇ 55)) obtained by second stage fractionation of first olein (oIein(56)) from alkali- refined palm oil did not contain any detectable amounts of 3-MCPD, 2-MCPD or GE when tested by the DGF Standard Method "3-in-1 method,"
  • the second oiein fraction (double fractionated ofein(59)) obtained by second stage fractionation of first olein (olein(56)) from alkali-refined palm oil contained only 0.12 ppm 3-MCPD and did not contain any detectable amounts of 2-MCPD o GE when tested by the DGF Standard Method "3-ii>1 method.”
  • the levels of GE and MCPD after subsequent deodorization of the soft PMF(55) and doubie fractionated oiein(59) are expected each to be less than one part per miilion of MCPD as demonstrated in
  • Palm oil containing 5.5 % free fatty acid was alkaii refined
  • Example 2 substantially as outlined in Example 2 except that the crude palm oil was not subjected to an acid treatment step before the alkali refining step. Alkali-refining of crude palm oil (about 5 kg, ADM, Hamburg, Germany) was carried out after
  • First stage fractionation of alkali-refined, bleached palm oil was carried out substantially as outlined in Example 1.
  • the cooled alkali-refined, bleached palm oil was vacuum-filtered through black ribbon filter paper (12 - 25 microns) at room temperature to obtain palm fractions (207 weight percent palm stearin and 79.3 weight percent palm oiein).
  • the palm fractions were deodorized for 3 hours at 220 °C.
  • the firstm stearin and first olein were tested for 3-MCPD, 2-MCPD, GEs, and free fatty acids (Table 8).
  • the levels of 3-MCPD and GE were determined by the 3-irv1 method of SGS Hamburg, Germany at SGS Germany GmbH, Hamburg, Germany,
  • first stearin containing less than one part per million of MCPD and less than one part per million GE was obtained after deodorizing the palm stearin.
  • the corresponding first olein contained slightly more than one part per million of MCPD and less than one part per million GE.
  • exemplary yields of stearin ⁇ 35) ranged from 10-30 weight percent of the starting paim oil, with
  • PMF(30) ranged from 15-35 weight percent of the starting sPMF ⁇ 45), with corresponding exemplary yields of PMF(49) ranging from 85-65 weight percent of the starting Soft FMF(45).
  • the 3-MCPD content of the starting Soft PMF(45) was 1.0 ppm, and fractionation resulted in PMF(30) containing 0.8 ppm 3-MCPD and PMF(49) containing 1.1 ppm 3-MCPD.
  • exemplary yields of P F(39) ranged from 20-50 weight percent of the starting P F(49) ; with corresponding exemplary yields of Olein flussig(54) ranging from 80-50 weight percent of the starting PMF(49).
  • the 3-MCPD content of the starting P F(49) was 1.1 ppm, and fractionation resulted in PMF ⁇ 39) containing 0.6 ppm 3-MCPD and Olein flussig(54) containing 1.3 ppm 3-MCPD.
  • PMF ⁇ 39 0.6 ppm 3-MCPD
  • Olein flussig(54) 1.3 ppm 3-MCPD.

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  • Wood Science & Technology (AREA)
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Abstract

L'invention concerne des fractions d'huile de palme ayant un faible taux d'au moins l'un parmi les esters de monochloropropanediol et de glycidol et les procédés se rapportant à celles-ci. L'huile de palme de départ est soumise à un raffinage par un alcali pour réduire le taux d'acides gras libres, et l'huile de palme raffinée par un alcali est soumise à au moins une étape de fractionnement. Les fractions pauvres en esters de monochloropropanediol et de glycidol sont obtenues de cette façon. Ces fractions peuvent être soumises à un blanchiment ou à un blanchiment et une désodorisation pour obtenir des fractions blanchies ou des fractions blanchies et désodorisées pauvres en esters de monochloropropanediol et de glycidol.
PCT/US2013/037678 2012-04-27 2013-04-23 Procédés perfectionnés de fractionnement WO2013163112A1 (fr)

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WO2019175258A1 (fr) * 2018-03-14 2019-09-19 Societe Des Produits Nestle S.A. Purification mécanique d'huiles de triacylglycéride
CN110257169A (zh) * 2019-06-12 2019-09-20 深圳精益油脂技术有限公司 一种制备低缩水甘油酯及低3-mcpd酯含量的棕榈油的方法
WO2020126117A1 (fr) * 2018-12-19 2020-06-25 Societe Des Produits Nestle S.A. Prévention de la formation de mcpde dans les huiles de triacylglycérides
WO2020236076A1 (fr) * 2019-05-21 2020-11-26 Aak Ab Composition de matière grasse comestible améliorée
WO2022076464A1 (fr) * 2020-10-06 2022-04-14 Archer Daniels Midland Company Raffinage d'huile physique modifiée à traitement alcalin intégré
RU2816877C2 (ru) * 2019-05-21 2024-04-08 Aak Аб Улучшенная композиция пищевых жиров

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US11672258B2 (en) 2015-08-25 2023-06-13 Dsm Ip Assets B.V. Refined oil compositions and methods for making
WO2019175258A1 (fr) * 2018-03-14 2019-09-19 Societe Des Produits Nestle S.A. Purification mécanique d'huiles de triacylglycéride
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WO2020126117A1 (fr) * 2018-12-19 2020-06-25 Societe Des Produits Nestle S.A. Prévention de la formation de mcpde dans les huiles de triacylglycérides
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