AU679850B2 - Fractionation of triglyceride oils - Google Patents
Fractionation of triglyceride oilsInfo
- Publication number
- AU679850B2 AU679850B2 AU20721/95A AU2072195A AU679850B2 AU 679850 B2 AU679850 B2 AU 679850B2 AU 20721/95 A AU20721/95 A AU 20721/95A AU 2072195 A AU2072195 A AU 2072195A AU 679850 B2 AU679850 B2 AU 679850B2
- Authority
- AU
- Australia
- Prior art keywords
- oil
- triglyceride
- crystallisation
- process according
- phase
- 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
Links
- 239000003921 oil Substances 0.000 title claims description 40
- 238000005194 fractionation Methods 0.000 title claims description 22
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 title claims description 21
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims description 51
- 238000002425 crystallisation Methods 0.000 claims description 40
- 235000019198 oils Nutrition 0.000 claims description 39
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 25
- 230000008569 process Effects 0.000 claims description 22
- 235000019482 Palm oil Nutrition 0.000 claims description 19
- 239000002540 palm oil Substances 0.000 claims description 19
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 15
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 12
- 229930195729 fatty acid Natural products 0.000 claims description 12
- 239000000194 fatty acid Substances 0.000 claims description 12
- 150000004665 fatty acids Chemical class 0.000 claims description 10
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 8
- 239000003346 palm kernel oil Substances 0.000 claims description 8
- 235000019865 palm kernel oil Nutrition 0.000 claims description 8
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 4
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 4
- 239000005642 Oleic acid Substances 0.000 claims description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 4
- 235000021314 Palmitic acid Nutrition 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 4
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 2
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims description 2
- 235000014121 butter Nutrition 0.000 claims description 2
- 239000003240 coconut oil Substances 0.000 claims description 2
- 235000019864 coconut oil Nutrition 0.000 claims description 2
- 235000012343 cottonseed oil Nutrition 0.000 claims description 2
- 239000002385 cottonseed oil Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 239000013078 crystal Substances 0.000 description 19
- 238000000926 separation method Methods 0.000 description 18
- 239000012071 phase Substances 0.000 description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 239000000654 additive Substances 0.000 description 12
- 235000019197 fats Nutrition 0.000 description 12
- 239000007790 solid phase Substances 0.000 description 12
- 230000000996 additive effect Effects 0.000 description 9
- 239000003607 modifier Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 7
- -1 sucrose fatty acid esters Chemical class 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 4
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- PTHLSIBOMNYSIS-UHFFFAOYSA-N 5-(4-aminophenyl)-8-chloro-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol Chemical compound C1N(C)CCC2=CC(Cl)=C(O)C=C2C1C1=CC=C(N)C=C1 PTHLSIBOMNYSIS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- HFJHNGKIVAKCIW-UHFFFAOYSA-N Stearyl monoglyceridyl citrate Chemical compound OCC(O)CO.OC(=O)CC(O)(CC(O)=O)CC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O HFJHNGKIVAKCIW-UHFFFAOYSA-N 0.000 description 3
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- QHZLMUACJMDIAE-UHFFFAOYSA-N 1-monopalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)CO QHZLMUACJMDIAE-UHFFFAOYSA-N 0.000 description 2
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 235000019961 diglycerides of fatty acid Nutrition 0.000 description 2
- 235000012041 food component Nutrition 0.000 description 2
- 239000005417 food ingredient Substances 0.000 description 2
- 239000000295 fuel oil Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 235000019960 monoglycerides of fatty acid Nutrition 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- DNISEZBAYYIQFB-PHDIDXHHSA-N (2r,3r)-2,3-diacetyloxybutanedioic acid Chemical compound CC(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(C)=O DNISEZBAYYIQFB-PHDIDXHHSA-N 0.000 description 1
- GFAZGHREJPXDMH-UHFFFAOYSA-N 1,3-dipalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCC GFAZGHREJPXDMH-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- QTNOUYPLTBNDOZ-UHFFFAOYSA-N 2,3-di(octadecanoyloxy)propyl octadecanoate;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC QTNOUYPLTBNDOZ-UHFFFAOYSA-N 0.000 description 1
- 240000001889 Brahea edulis Species 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- JEJLGIQLPYYGEE-UHFFFAOYSA-N glycerol dipalmitate Natural products CCCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCCCC JEJLGIQLPYYGEE-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 235000021243 milk fat Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000005457 triglyceride group Chemical group 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
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
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)
Description
Fractionation of triglyceride oils
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. Generally 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 major problem encountered with phase separation in the dry fractionation process is the inclusion of a lot of liquid olein fraction in the separated stearin fraction. The olein fraction is thereby entrained in the inter- and
intracrystal spaces of the crystal mass of the stearin fraction. Therefore the separation of the solid from the liquid fraction is only partial.
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.
For the related solvent fractionation process, where the fat to be fractionated is crystallised from e.g. a hexane or acetone solution, separation efficiencies may be up to
95%.
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.
It is known to interfere with the crystallisation by adding to a crystallising oil a substance which will be generally indicated as crystallisation modifying substance. The presence of small quantities of such a substance in the cooling oil may accelerate, retard or inhibit crystallisation. In certain situations the above substances are more precisely indicated as crystal habit modifiers. Known crystallisation modifiers are 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.
Other 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. Other 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. None of them has appeared to be ideal with respect to high separation efficiency and fitness to be used for the preparation of food ingredients. SU 1722377 (DERWENT 93-074294) discloses that fatty acid monoglycerides influence the crystallisation of milk fat. Chemical Abstracts 84, (1976) 42219 deals specifically with monoglycerides of unsaturated fatty acids which accelerate the crystallization of hardened vegetable oils. Fatty acid monoglycerides which have been esterified with citric acid and which are marketed under the name Acidan™ have shown to modify the crystallization rate of triglyceride fat, particularly glycerol tristearin (J. Am. Oil. Chem. Soc. 59, (1982) p. 181-185).
STATEMENT OF INVENTION
It has been found that in triglyceride fat fractionation monoglycerides or diglycerides of fatty acids are suited to enhance the separation efficiency. Accordingly 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. olein phase, where before crystallisation starts a 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.
DETAILS OF THE INVENTION
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. During crystallisation 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, Anstrichmittel 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. At microscopic inspection 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. Optionally 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.
Generally, the best results are obtained when the length of the fatty acid side-chains match the length of the fatty acid chains of the desired stearin phase. Matching chains should have the same or about the same number of carbon atoms. Therefore, when palm oil is fractionated, preferred fatty acids are C14, C16 and C18 fatty acids. 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.
Although the invention is useful for solvent fractionation or detergent fractionation, 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 Dimodan™.
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 Acidan™.
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.
Example l
Dry fractionation of palm oil
A sample was prepared containing 1000 g of palm oil
(neutralised, bleached, deodorised, having a SSS content of 8 wt.% and a palmitic acid : oleic acid ratio of 1.12) and
1 g (0.1%) of Acidan CN™ * . The sample was heated and stirred at 65°C until completely liquefied (no solid phase content) and then slowly cooled. Crystallisation proceeded in a thermostated cabin in a stagnant mode at the chosen temperature of 23°C until a constant solid phase content was reached. The sample was filtered and pressed at 12 bar in a membrane filter press for 30 minutes. After filtration and pressing, the solid phase content of the cake was measured and also the weight of the filtrate (the olein phase) . The stearin yield is the weight of the crystal mass remaining on the filter expressed as a percentage of the feed. Table I shows the measured solid phase content of the slurry, the increase of the solid phase content of the stearin-cake and the olein yield.
Acidan CN™ is a neutralised citric acid ester of monoglyceride made from edible, refined, hydrogenated fat as marketed by GRINDSTED, Brabrand, Denmark.
Examples 2-6
Dry fractionation of palm oil and palm kernel oil
The dry fractionation process of example 1 is repeated with different additives and two oils (palm kernel oil and palm oil) . The palm kernel oil samples have been pressed at 6 bar, the palm oil ones at 12 bar. The ingredients and the results are summarized in Table I.
Before filtration samples contained the same amount of solid fat ((12% for palm oil, 25% for palm kernel oil). The results of Table I show that the stearin fractions of the crystallisation modifying substance containing samples 1-6 have retained considerably less olein than the stearin fractions of comparison samples A-D.
TABLE I
Ex. Additive Add. Fat Slurry Incre Olein wt.% (1) SPC 2) ase % yield wt.% (3) wt.%
1 Acidan™ (8) 0.16 PO 12 80 80
2 Acidan™ (8) 0.16 PK 25 10 50
3 Glycerol 0.1 PO 12 29 70 monopaImitate
4 Glycerol 0.1 PK 25 20 48 monopalmitate
5 Glycerol mono- 0.1 PO 12 29 70 oleate
6 Glycerol 0.1 PO 12 20 68 dipalmitate
Comparison examples
A No additive - PO 12 0 (9) 60
B No additive - PK 25 0 (10 45
C Admul GLP™ 4) 3.0 PO 12 0 40
D Admul 0.05 PO 12 n.d. n.d. Datem™ (6)
E Admul AC™ (7) 0.16 PO 12 n.d. n.d.
F Tween 60™ (5) 1.0 PO 12 -3 58
n.d. not determined: separation of stearin and olein phases not possible
(1) PK = palm kernel oil
PO = palm oil (neutralised, bleached, deodorised, having a SSS content of 8 wt.% and a palmitic acid : oleic acid ratio of 1.12)
(2) SPC = solid phase content before stearin/olein
separation
(3) increase of solid phase content of stearin phase (SE) compared with crystallization without additive (comparison examples A and B)
(4) Admul GLP™ = monoacylglyceride esterified with lactic acid (ex Quest)
(5) Tween 60™ = a sorbitan ester (ex Quest)
(6) Admul Datem™ = monoacylglyceride esterified with diacetyltartaric acid (ex Quest)
(7) Admul AC™ = monoacylglyceride esterified with acetic acid (ex Quest)
(8) Acidan ™ is a neutralised citric acid ester of a fatty acid monoglyceride made from edible fat (ex GRINDSTED)
(9) Separation efficiency of palm oil without additive ??
(10) Separation efficiency of palmkernel oil without additive ??
When 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.
When using another well known emulsifier as additive as in example F even a negative effect is observed.
Claims (7)
1. Process for separating solid fatty material from a partially crystallised 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 olein phase, where before crystallisation starts a 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.
2. Process according to claim 1, characterised in that the mono- or diglyceride has been esterified with citric acid using 0.5 - 2 mol equivalents of citric acid per mol mono- or diglyceride.
3. Process according to claim 1 or 2, characterised in that the process is applied as a dry fractionation process.
4. Process according to any one of claims 1-3, characterised in that the triglyceride oil to be fractionated is shea oil, coconut oil, cottonseed oil, butter oil, hardened rapeseed oil, hardened soybean oil or fractions of these oils, but preferably is palm oil or palm kernel oil.
5. Process according to claim 4, characterised in that the palm oil to be fractionated has a SSS content < 8.5 wt.%.
6. Process according to claims 4 or 5, characterised in that the palm oil to be fractionated has a palmitic acid : oleic acid ratio < 1.17.
7. Process according to any one of claims 1-6, characterised in that the crystallisation modifying substance is used in an amount of 0.005-5 wt.%, preferably 0.01-2 wt.% on the total amount of oil.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP94200822 | 1994-03-29 | ||
| EP94200822 | 1994-03-29 | ||
| PCT/EP1995/001038 WO1995026391A1 (en) | 1994-03-29 | 1995-03-20 | Fractionation of triglyceride oils |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2072195A AU2072195A (en) | 1995-10-17 |
| AU679850B2 true AU679850B2 (en) | 1997-07-10 |
Family
ID=8216750
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU20721/95A Ceased AU679850B2 (en) | 1994-03-29 | 1995-03-20 | Fractionation of triglyceride oils |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0753038B1 (en) |
| AU (1) | AU679850B2 (en) |
| CA (1) | CA2186767C (en) |
| DE (1) | DE69519019T2 (en) |
| DK (1) | DK0753038T3 (en) |
| ES (1) | ES2151052T3 (en) |
| WO (1) | WO1995026391A1 (en) |
| ZA (1) | ZA952576B (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU720939B2 (en) * | 1997-02-06 | 2000-06-15 | Unilever Plc | Fractionation of triglyceride fats |
| JP2002526046A (en) | 1998-10-02 | 2002-08-20 | カーギル インコーポレイテッド | Vegetable oil with high stearic acid content |
| US6713117B1 (en) | 1998-10-02 | 2004-03-30 | Dharma Kodali | Vegetable oil having elevated stearic acid content |
| BR0111588B1 (en) * | 2000-06-15 | 2011-12-13 | processes for the preparation of a triglyceride fat suitable for the structuring of a liquid vegetable oil and for the preparation of a fat phase, food product, and use of a fat mixture. | |
| WO2011080530A1 (en) * | 2009-12-29 | 2011-07-07 | Aceites Y Grasas Vegetales S.A. | Palm oil fractions with low concentration of saturates and production method thereof |
| MY169820A (en) * | 2011-09-09 | 2019-05-16 | Sime Darby Plantation Berhad | A method for producing triacylglycerol oil |
| IS2978B (en) | 2015-05-13 | 2017-09-15 | Margildi Ehf. | Winterization of fish oil |
| WO2019175256A1 (en) * | 2018-03-14 | 2019-09-19 | Societe Des Produits Nestle S.A. | Purification of triacylglyceride oils |
| US11629310B2 (en) * | 2018-12-19 | 2023-04-18 | Societe Des Produits Nestle S.A. | Purification of triacylglyceride oils by auxiliary washing |
| CN117024278A (en) * | 2023-08-21 | 2023-11-10 | 赞宇科技集团股份有限公司 | Crystallization assisting agent and application thereof, and method for removing palmitic acid triglyceride by crystallization decrement |
Citations (3)
| 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 |
| SU1722377A1 (en) * | 1989-11-28 | 1992-03-30 | Заготовительно-Сбытовой Научно-Производственный Кооператив "Агропромнаука Ссср" | Method for production of reclaimed creamery butter |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5543170A (en) * | 1978-09-22 | 1980-03-26 | Kao Corp | Separating fatty material |
-
1995
- 1995-03-20 EP EP95913146A patent/EP0753038B1/en not_active Expired - Lifetime
- 1995-03-20 ES ES95913146T patent/ES2151052T3/en not_active Expired - Lifetime
- 1995-03-20 DE DE69519019T patent/DE69519019T2/en not_active Expired - Fee Related
- 1995-03-20 DK DK95913146T patent/DK0753038T3/en active
- 1995-03-20 AU AU20721/95A patent/AU679850B2/en not_active Ceased
- 1995-03-20 CA CA002186767A patent/CA2186767C/en not_active Expired - Fee Related
- 1995-03-20 WO PCT/EP1995/001038 patent/WO1995026391A1/en not_active Ceased
- 1995-03-29 ZA ZA952576A patent/ZA952576B/en unknown
Patent Citations (3)
| 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 |
| SU1722377A1 (en) * | 1989-11-28 | 1992-03-30 | Заготовительно-Сбытовой Научно-Производственный Кооператив "Агропромнаука Ссср" | Method for production of reclaimed creamery butter |
Also Published As
| Publication number | Publication date |
|---|---|
| DE69519019T2 (en) | 2001-05-17 |
| WO1995026391A1 (en) | 1995-10-05 |
| DE69519019D1 (en) | 2000-11-09 |
| DK0753038T3 (en) | 2000-10-30 |
| EP0753038A1 (en) | 1997-01-15 |
| AU2072195A (en) | 1995-10-17 |
| CA2186767A1 (en) | 1995-10-05 |
| EP0753038B1 (en) | 2000-10-04 |
| CA2186767C (en) | 2001-10-16 |
| ES2151052T3 (en) | 2000-12-16 |
| ZA952576B (en) | 1996-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |