WO1995026391A1 - Fractionnement d'huiles triglycerides - Google Patents
Fractionnement d'huiles triglycerides Download PDFInfo
- Publication number
- WO1995026391A1 WO1995026391A1 PCT/EP1995/001038 EP9501038W WO9526391A1 WO 1995026391 A1 WO1995026391 A1 WO 1995026391A1 EP 9501038 W EP9501038 W EP 9501038W WO 9526391 A1 WO9526391 A1 WO 9526391A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil
- triglyceride
- crystallisation
- process according
- phase
- Prior art date
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
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0083—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils with addition of auxiliary substances, e.g. cristallisation promotors, filter aids, melting point depressors
Definitions
- the present invention is concerned with a process for fractionating triglyceride oils.
- the fractionation (fractional crystallisation) of triglyceride oils is described by Gunstone, Harwood and Padley in The Lipid Handbook, 1986 edition, pages 213-215.
- triglyceride oils are mixtures of various triglycerides having different melting points.
- the composition of triglyceride oils may be modified e.g. by separating from them by crystallisation a fraction having a different melting point or solubility.
- One fractionation method is the so-called dry fractionation process which comprises cooling the oil until a solid phase crystallises and separating the crystallised phase from the liquid phase.
- the liquid phase is denoted as olein fraction, while the solid phase is denoted as stearin fraction.
- the separation of the phases is usually carried out by filtration, optionally applying some kind of pressure.
- the solids content of the stearin fraction is denoted as the separation efficiency. For the dry fractionation of palm oil it seldom surpasses 50 wt.% . This is detrimental to the quality of the stearin as well as to the yield of the olein.
- Dry fractionation is a process which is cheaper and more environmentally friendly than solvent fractionation. For dry fractionation an increase of separation efficiency is therefore much desired.
- crystallisation modifying substance e.g. sucrose fatty acid esters, described in US 3,059,010 and fatty acid esters of glucose and derivatives, described in US 3,059,011. These crystallisation modifiers are effective in speeding up the crystallisation rate but are not reported to increase the separation efficiency. They do not even allude to such an effect.
- crystallisation modifiers e.g. as described in US 3,158,490 when added to kitchen oils have the effect that solid fat crystallisation is prevented or at least retarded.
- Other types of crystallisation modifiers particularly referred to as crystal habit modifiers, are widely used as an ingredient for mineral fuel oils in which waxes are prone to crystallize at low temperatures.
- US 3,536,461 teaches the addition of a crystal habit modifier to fuel oil with the effect that the cloud point (or pour point) temperature is lowered far enough to prevent crystal precipitation. Or, alternatively, the solids are induced to crystallize in a different habit so that the crystals when formed can pass fuel filters without clogging them.
- crystal habit modifiers are actually able to change the habit of the crystallized triglyceride fat crystals in a way such that after crystallization the crystals, the stearin phase, can be more effectively separated from the liquid phase, the olein phase.
- Publications describing such crystal habit modifiers are e.g. GB 1 015 354 or US 2,610,915 where such effect is accomplished by the addition of small amounts of a polymerisation product of esters of vinyl alcohol or of a substituted vinyl alcohol and in co- pending PCT application WO 95/04122 by the addition of esterified copolymers of maleic anhydride and styrene.
- US 3,059,008 describes the use of dextrin derivatives for the same purpose.
- the invention relates to a process for separating solid fatty material crystallised from a triglyceride oil, which comprises the steps: a. heating the oil until no longer a substantial amount of solid triglyceride is present in the oil, b. cooling and crystallising the triglyceride oil resulting in a solid stearin phase besides a liquid olein phase and c. recovering the stearin phase by separating it from the.
- crystallisation modifying substance is added to said triglyceride oil or to a solution of said triglyceride oil in an inert solvent, characterized in that the crystallisation modifying substance is a monoglyceride or diglyceride of fatty acids optionally esterified with citric acid.
- the oil to be fractionated is mixed with the crystallisation modifying substance (the additive) before crystallisation starts, preferably before the oil is heated or dissolved in the solvent so that all solid triglyceride fat and preferably also the modifying substance is liquefied. Then the oil or solution is cooled to the chosen crystallisation temperature.
- a suitable temperature range for e.g. palm oil is 15-35°C.
- To each temperature belongs a specific composition of the olein and stearin phases. Crystallisation proceeds at the chosen temperature until the crystallised oil stabilises to a constant solid phase content. The crystallisation time increases when more solid phase is desired and the temperature is lowered. Usual times are in the range of 4-16 hours.
- the oil may remain quiescent or is stirred, e.g. with a gate stirrer.
- the improvement in separation efficiency may depend on the mode of crystallisation, either stagnant or stirred. Often good results are obtained with " stagnant crystallisation rather than with stirred crystallisation. From the point of view of process economy, however, stirred crystallization is preferred.
- the stearin and olein phases may be separated by filtration but for an effective separation of the solid from the liquid phase generally a membrane filter press is used, which allows higher pressures. Suitable pressures are 3-50 bar, exerted for about 20-200 minutes. However, already with a low or moderate pressure the stearin phase obtained according to the present invention is easily and with a high efficiency separated from the olein. As a rule it takes about 30-60 minutes to get a proper separation of both phases.
- the solids content of the crystal slurry before separation and of the stearin phase obtained after separation is measured according to the known pulse NMR method (ref. Fette, Seifen, Anstrichstoff 1978, J3C), nr. 5, pp. 180- 186) .
- the effect of the invention is believed to be caused by alteration of the crystal structure or crystal habit of the stearin under the influence of the additives. These might interfere in different ways with the growth of the various crystal faces.
- the effect of the presence of the mono- or diglyceride additives is that the crystals and crystal aggregates formed in the oil are conspicuously different from the crystals obtained without those crystallisation modifying substances. These crystals and aggregates can be filtered more effectively in that the stearin fraction retains less of the olein fraction even at low or moderate filtration pressure. The altered crystallisation results therefore in a considerable increase of the separation efficiency.
- the present process for obtaining stearin with increased solid levels is characterised by the use of crystallisation modifying substances which are mono- or diglycerides of fatty acids.
- the ester group preferably is situated at either or both of the terminal carbon atoms of the glyceryl moiety.
- the remaining hydroxyl group(s) have been esterified with citric acid, preferably 0.5 - 2 mol equivalents, so that a part or all the hydroxyl groups have been esterified.
- the mono- or diglycerides used in the invention may be derived from a single fatty acid, such as glycerol monopalmitate, mono-oleate or dipalmitate, but usually these are derived from various fatty acids with a distribution which reflects the fatty acid distribution of the edible fat used for the preparation of the mono- or diglyceride.
- the process preferably is carried out as a dry fractionation process.
- the process can be applied on triglyceride oils containing relatively high melting fat, for which fractionation is desired such as palm oil, palm kernel oil, shea oil, coconut oil, cottonseed oil, butter oil, hardened rapeseed oil, hardened soybean oil or fractions of these oils.
- the process is particularly useful for fractionating palm oil.
- the palm oil might be crude, but generally a refined quality is used.
- Palm oil contains fully saturated triglycerides SSS.
- the palm oil to be fractionated preferably has a SSS content ⁇ 8.5 wt.%, more preferably 7-8.5 wt.% and the palmitic acid : oleic acid ratio preferably is less than 1.17, more preferably 1.08-1.16.
- the crystallisation modifying substance is suitably applied in an amount of 0.005 - 5 wt.%, preferably 0.01-2 wt.% on the total amount of oil.
- the mono- or diglycerides to be used according to the invention can be prepared using common methods for preparing such well known products.
- the crystallisation modifying substances of the present invention are generally known and marketed as emulsifiers under various trade names such as DimodanTM.
- the citric esters are obtained using standard methods e.g. by treating the monoglycerides under proper esterifying conditions with 0.5 - 2 mol equivalents citric acid. The obtained citric ester is neutralised. Such product is marketed as an emulsifier by e.g. GRINDSTED under the trade name AcidanTM.
- a major advantage of the present crystallisation modifying substances is that they have acquired the status of permitted food ingredients and therefore may be used for the fractionation of edible oils.
- a sample was prepared containing 1000 g of palm oil
- Acidan CNTM is a neutralised citric acid ester of monoglyceride made from edible, refined, hydrogenated fat as marketed by GRINDSTED, Brabrand, Denmark.
- PO palm oil (neutralised, bleached, deodorised, having a SSS content of 8 wt.% and a palmitic acid : oleic acid ratio of 1.12)
- Admul GLPTM monoacylglyceride esterified with lactic acid (ex Quest)
- Tween 60TM a sorbitan ester (ex Quest)
- Admul DatemTM monoacylglyceride esterified with diacetyltartaric acid (ex Quest)
- Admul ACTM monoacylglyceride esterified with acetic acid (ex Quest)
- Acidan TM is a neutralised citric acid ester of a fatty acid monoglyceride made from edible fat (ex GRINDSTED)
- the additive is a mono- or diglyceride esterified with another acid than citric acid, as in comparison examples C, D and E, no increase of the solid phase content during dry fractionation is achieved.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (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
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP95913146A EP0753038B1 (fr) | 1994-03-29 | 1995-03-20 | Fractionnement d'huiles triglycerides |
DK95913146T DK0753038T3 (da) | 1994-03-29 | 1995-03-20 | Fraktionering af triglyceridolier |
DE69519019T DE69519019T2 (de) | 1994-03-29 | 1995-03-20 | Glycerid-öl fraktionierung |
CA002186767A CA2186767C (fr) | 1994-03-29 | 1995-03-20 | Fractionnement d'huiles triglycerides |
AU20721/95A AU679850B2 (en) | 1994-03-29 | 1995-03-20 | Fractionation of triglyceride oils |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP94200822 | 1994-03-29 | ||
EP94200822.8 | 1994-03-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1995026391A1 true WO1995026391A1 (fr) | 1995-10-05 |
Family
ID=8216750
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1995/001038 WO1995026391A1 (fr) | 1994-03-29 | 1995-03-20 | Fractionnement d'huiles triglycerides |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP0753038B1 (fr) |
AU (1) | AU679850B2 (fr) |
CA (1) | CA2186767C (fr) |
DE (1) | DE69519019T2 (fr) |
DK (1) | DK0753038T3 (fr) |
ES (1) | ES2151052T3 (fr) |
WO (1) | WO1995026391A1 (fr) |
ZA (1) | ZA952576B (fr) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000019832A1 (fr) | 1998-10-02 | 2000-04-13 | Cargill, Incorporated | Huiles vegetales riches en acide stearique |
US6162934A (en) * | 1997-02-06 | 2000-12-19 | Lipton, Division Of Conopco, Inc. | Fractionation of triglyceride fats |
US6475548B2 (en) * | 2000-06-15 | 2002-11-05 | Lipton, Division Of Conopco, Inc. | Preparation of a blend of triglycerides |
US6713117B1 (en) | 1998-10-02 | 2004-03-30 | Dharma Kodali | Vegetable oil having elevated stearic acid content |
WO2011080530A1 (fr) * | 2009-12-29 | 2011-07-07 | Aceites Y Grasas Vegetales S.A. | Fractions d'huile de palme à faible teneur en constituants saturés et leur procédé d'obtention |
WO2013036096A1 (fr) | 2011-09-09 | 2013-03-14 | Sime Darby Malaysia Berhad | Procédé pour la production d'huile de triacylglycérol |
WO2019175256A1 (fr) * | 2018-03-14 | 2019-09-19 | Societe Des Produits Nestle S.A. | Purification d'huiles triacylglycéridiques |
EP3294851B1 (fr) | 2015-05-13 | 2021-02-17 | Margildi EHF. | Frigélisation d'huile de poisson |
CN113574153A (zh) * | 2018-12-19 | 2021-10-29 | 雀巢产品有限公司 | 通过辅助洗涤纯化三酰基甘油酯油 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3059010A (en) * | 1961-09-21 | 1962-10-16 | Procter & Gamble | Fat crystallization process |
GB1015354A (en) * | 1962-06-20 | 1965-12-31 | Chemetron Corp | Separation of mixtures of fats and fatty acids |
JPS5543170A (en) * | 1978-09-22 | 1980-03-26 | Kao Corp | Separating fatty material |
SU1722377A1 (ru) * | 1989-11-28 | 1992-03-30 | Заготовительно-Сбытовой Научно-Производственный Кооператив "Агропромнаука Ссср" | Способ производства восстановленного сливочного масла |
-
1995
- 1995-03-20 CA CA002186767A patent/CA2186767C/fr not_active Expired - Fee Related
- 1995-03-20 DK DK95913146T patent/DK0753038T3/da active
- 1995-03-20 EP EP95913146A patent/EP0753038B1/fr not_active Expired - Lifetime
- 1995-03-20 ES ES95913146T patent/ES2151052T3/es not_active Expired - Lifetime
- 1995-03-20 WO PCT/EP1995/001038 patent/WO1995026391A1/fr active IP Right Grant
- 1995-03-20 DE DE69519019T patent/DE69519019T2/de not_active Expired - Fee Related
- 1995-03-20 AU AU20721/95A patent/AU679850B2/en not_active Ceased
- 1995-03-29 ZA ZA952576A patent/ZA952576B/xx unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3059010A (en) * | 1961-09-21 | 1962-10-16 | Procter & Gamble | Fat crystallization process |
GB1015354A (en) * | 1962-06-20 | 1965-12-31 | Chemetron Corp | Separation of mixtures of fats and fatty acids |
JPS5543170A (en) * | 1978-09-22 | 1980-03-26 | Kao Corp | Separating fatty material |
SU1722377A1 (ru) * | 1989-11-28 | 1992-03-30 | Заготовительно-Сбытовой Научно-Производственный Кооператив "Агропромнаука Ссср" | Способ производства восстановленного сливочного масла |
Non-Patent Citations (8)
Title |
---|
CHEMICAL ABSTRACTS, vol. 84, no. 4, 16 February 1976, Columbus, Ohio, US; abstract no. 42219, I. NIIYA ET AL: "EFFECTS OF EMULSIFIERS ON THE CRYSTAL GROWTH OF EDIBLE SOLID FATS" * |
DATABASE WPI Week 8019, Derwent World Patents Index; AN 80-33709 * |
DATABASE WPI Week 9309, Derwent World Patents Index; AN 93-074294 * |
H. BIRNBAUM: "THE MONOGLYCERIDES - MANUFACTURE, CONCENTRATION, DERIVATIVES AND APPLICATIONS", BAKER'S DIGEST, vol. 55, no. 6, pages 6 - 18 * |
K. PLAYER: "EMULSIFIER APPLICATION FOR CONFECTIONERY PRODUCTS", THE MANUFACTURING CONFECTIONER, vol. 66, no. 110, pages 61 - 65 * |
L. KOSLOVSKY: "SALAD OIL AND EDIBLE FATS FROM PALM OIL BY A NEW FRACTIONAL CRYSTALLIZATION METHOD IN ISOPROPYL ALCOHOL", OLEAGINEUX, vol. 29, no. 8, pages 421 - 426 * |
N. GARTI ET AL: "CRYSTAL STRUCTURE MODIFICATIONS OF TRISTEARIN BY FOOD EMULSIFIERS", JAOCS, vol. 59, no. 4, pages 181 - 185 * |
NIPPON SHOKUHIN KOGYO GAKKAI-SHI, vol. 20, no. 5, pages 191 - 198 * |
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6162934A (en) * | 1997-02-06 | 2000-12-19 | Lipton, Division Of Conopco, Inc. | Fractionation of triglyceride fats |
WO2000019832A1 (fr) | 1998-10-02 | 2000-04-13 | Cargill, Incorporated | Huiles vegetales riches en acide stearique |
US6713117B1 (en) | 1998-10-02 | 2004-03-30 | Dharma Kodali | Vegetable oil having elevated stearic acid content |
US6994882B2 (en) | 1998-10-02 | 2006-02-07 | Cargill, Incorporated | Vegetable oil having elevated stearic acid content |
US6475548B2 (en) * | 2000-06-15 | 2002-11-05 | Lipton, Division Of Conopco, Inc. | Preparation of a blend of triglycerides |
WO2011080530A1 (fr) * | 2009-12-29 | 2011-07-07 | Aceites Y Grasas Vegetales S.A. | Fractions d'huile de palme à faible teneur en constituants saturés et leur procédé d'obtention |
AU2012305047B2 (en) * | 2011-09-09 | 2015-11-26 | Sime Darby Malaysia Berhad | A method for producing triacylglycerol oil |
CN103906831A (zh) * | 2011-09-09 | 2014-07-02 | 森达美马来西亚有限公司 | 用于生产三酰甘油的油的方法 |
WO2013036096A1 (fr) | 2011-09-09 | 2013-03-14 | Sime Darby Malaysia Berhad | Procédé pour la production d'huile de triacylglycérol |
EP3294851B1 (fr) | 2015-05-13 | 2021-02-17 | Margildi EHF. | Frigélisation d'huile de poisson |
WO2019175256A1 (fr) * | 2018-03-14 | 2019-09-19 | Societe Des Produits Nestle S.A. | Purification d'huiles triacylglycéridiques |
CN111818804A (zh) * | 2018-03-14 | 2020-10-23 | 雀巢产品有限公司 | 三酰基甘油酯油的纯化 |
JP2021516712A (ja) * | 2018-03-14 | 2021-07-08 | ソシエテ・デ・プロデュイ・ネスレ・エス・アー | トリアシルグリセリド油の精製 |
US11352585B2 (en) | 2018-03-14 | 2022-06-07 | Societe Des Produits Nestle S.A. | Purification of triacylglyceride oils |
CN113574153A (zh) * | 2018-12-19 | 2021-10-29 | 雀巢产品有限公司 | 通过辅助洗涤纯化三酰基甘油酯油 |
US20220081643A1 (en) * | 2018-12-19 | 2022-03-17 | Societe Des Produits Nestle S.A. | Purification of triacylglyceride oils by auxiliary washing |
US11629310B2 (en) * | 2018-12-19 | 2023-04-18 | Societe Des Produits Nestle S.A. | Purification of triacylglyceride oils by auxiliary washing |
CN113574153B (zh) * | 2018-12-19 | 2024-06-11 | 雀巢产品有限公司 | 通过辅助洗涤纯化三酰基甘油酯油 |
Also Published As
Publication number | Publication date |
---|---|
ES2151052T3 (es) | 2000-12-16 |
AU2072195A (en) | 1995-10-17 |
ZA952576B (en) | 1996-09-30 |
DE69519019D1 (de) | 2000-11-09 |
DK0753038T3 (da) | 2000-10-30 |
EP0753038B1 (fr) | 2000-10-04 |
CA2186767A1 (fr) | 1995-10-05 |
CA2186767C (fr) | 2001-10-16 |
DE69519019T2 (de) | 2001-05-17 |
EP0753038A1 (fr) | 1997-01-15 |
AU679850B2 (en) | 1997-07-10 |
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