EP0185524A2 - Edible fats - Google Patents
Edible fats Download PDFInfo
- Publication number
- EP0185524A2 EP0185524A2 EP85309086A EP85309086A EP0185524A2 EP 0185524 A2 EP0185524 A2 EP 0185524A2 EP 85309086 A EP85309086 A EP 85309086A EP 85309086 A EP85309086 A EP 85309086A EP 0185524 A2 EP0185524 A2 EP 0185524A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- process according
- fraction
- glycerides
- fat
- interesterification
- 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.)
- Granted
Links
- 239000003925 fat Substances 0.000 title claims description 20
- 125000005456 glyceride group Chemical group 0.000 claims abstract description 47
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- 235000019197 fats Nutrition 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 150000003626 triacylglycerols Chemical class 0.000 claims abstract description 10
- 235000019871 vegetable fat Nutrition 0.000 claims abstract description 10
- 235000014121 butter Nutrition 0.000 claims abstract description 7
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 3
- 229930195729 fatty acid Natural products 0.000 claims abstract description 3
- 239000000194 fatty acid Substances 0.000 claims abstract description 3
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 3
- 102000004882 Lipase Human genes 0.000 claims abstract 2
- 108090001060 Lipase Proteins 0.000 claims abstract 2
- 238000009884 interesterification Methods 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 16
- 238000005194 fractionation Methods 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 9
- 238000011084 recovery Methods 0.000 claims description 4
- 238000001640 fractional crystallisation Methods 0.000 claims description 3
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 235000004936 Bromus mango Nutrition 0.000 claims 1
- 241000631153 Diploknema butyracea Species 0.000 claims 1
- 240000007228 Mangifera indica Species 0.000 claims 1
- 235000014826 Mangifera indica Nutrition 0.000 claims 1
- 235000015076 Shorea robusta Nutrition 0.000 claims 1
- 240000000665 Simarouba glauca Species 0.000 claims 1
- 235000009184 Spondias indica Nutrition 0.000 claims 1
- 239000012188 paraffin wax Substances 0.000 claims 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 abstract description 14
- 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 abstract description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 102000004190 Enzymes Human genes 0.000 description 11
- 108090000790 Enzymes Proteins 0.000 description 11
- 238000002844 melting Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229940110456 cocoa butter Drugs 0.000 description 4
- 235000019868 cocoa butter Nutrition 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 230000008707 rearrangement Effects 0.000 description 4
- 150000004670 unsaturated fatty acids Chemical group 0.000 description 4
- 235000019482 Palm oil Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002540 palm oil Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 241000228245 Aspergillus niger Species 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 241001516747 Pentadesma Species 0.000 description 1
- 241000235403 Rhizomucor miehei Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 235000019879 cocoa butter substitute Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000004671 saturated fatty acids Chemical group 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
Definitions
- This invention relates to hard butters and their preparation from edible fats.
- Processes for the production of cocoa butter substitutes and extender fats from these alternative sources generally include fractionation steps in which these more valuable glycerides are separated from others with less desirable melting attributes, notably trisaturated glycerides and mono-saturated and tri-unsaturated triglycerides, but also asymmetric disaturated glycerides, where these can be separated.
- the separation is usually effected by fractional crystallisation, particularly from a solvent such as acetone or hexane, the more highly saturated glycerides being removed in a higher-melting or stearin fraction, and the more highly unsaturated glycerides being removed in a lower-melting or olein fraction.
- These less desirable fractions may constitute as much as half the original fat and command a much lower premium than the hard butter fraction.
- the present invention proposes a process for the recovery of hard butters from vegetable fats, in which a vegetable fat containing substantial amounts of symmetrical disaturated triglycerides of C 16 and C 18 fatty acids is fractionated to recover the said glycerides by separating at least a more highly unsaturated, lower-melting olein fraction, which is mixed with a substantially saturated C 16 /C 18 triglyceride fat, preferably by re-combining with an upper-melting , stearin fraction also separated from the vegetable fat, and the mixture interesterified in the presence of an enzyme catalyst which is preferably selectively active in the outer positions only of glycerides, i.e. the 1- and 1,3-positions or alpha-positions of the glycerides, to yield further quantities of symmetrical disaturated glycerides.
- an enzyme catalyst which is preferably selectively active in the outer positions only of glycerides, i.e. the 1- and 1,3-positions or alpha-position
- the olein fraction consists of glycerides having an unsaturated fatty acid residue in the 2-position, all these are theoretically capable of conversion by interesterification under the influence of the enzyme catalyst to symmetrical disaturated triglycerides, provided only that sufficient glycerides are present in the blends, for example in the upper-melting or stearin fraction with which it is preferably combined, containing saturated fatty acid residues in the alpha or 1,3-positions that are vulnerable to the catalyst for effecting interesterification with the more highly unsaturated glycerides.
- trisaturated glycerides may undergo interesterification with tri-unsaturated glycerides to provide 1-saturated di-unsaturated glycerides and these in turn to 1,3-disaturated glycerides, under the influence of the selective action of the catalyst.
- the trisaturated glycerides themselves convert correspondingly to asymmetric disaturated mono-unsaturated glycerides and symmetric di-unsaturated glycerides, i.e. 1,3-diunsaturated, 2-saturated glycerides.
- the interesterified glycerides may be separated as in conventional fractionation processes, to recover a fraction consisting essentially of symmetrical disaturated glycerides for use as a cocoa butter replacement fat.
- the more highly unsaturated glycerides in the interesterification mixture including in particular the symmetrical 1,3-di-unsaturated glycerides, form a lower-melting oleine fraction.
- Any unreacted trisaturated glycerides may be separated if necessary in a top fraction, and recycled for further interesterification with any asymmetric disaturated glycerides, whether these appear in a stearin or olein fraction separated from the symmetrical disaturated fraction.
- the mixture of interesterified glycerides may be separately fractionated or recombined with feedstock in the fractionation step of the process.
- the feedstock may be introduced into either unit and may thus be fractionated first, in admixture with the entire interesterification output, or interesterified first together with the recycled interesterified fractions from which the symmetrical disaturated glycerides have been removed.
- a purge may also be necessary of the symmetrical di-unsaturated glycerides to avoid build-up of this intractable material in the recycled composition.
- Rearrangement catalyst may also be used to convert this material and return it in a more tractable form, for example, a non-selective catalyst, a 2-selective catalyst, or one which is selectively active to saturated but not unsaturated fatty acid residues.
- a particular advantage of continuous operation is that the interesterification need be of relatively short duration since the interesterification can be incomplete for each pass through the unit. Enzyme interesterification is generally substantially slower than interesterification under the influence of inorganic catalysts which are also used at much higher temperatures. By continuous recycling however, the residence time in the interesterification step need be sufficient only to provide a significant improvement in the yield of the desired glycerides, without necessarily reaching equilibrium.
- the invention also includes recovery of the product from the rearrangement step, without fractionation or recycle, particularly for the preparation of hardstock fat which is then blended with liquid glyceride oils, to provide a composition suitable for margarine or other emulsion food spreads, or the fat may be used in ice-cream.
- Fractionation steps carried out in accordance with the invention may be conventional, either by solvent fractionation using acceptable solvent, for example acetone, hexane or nitroparaffins or ambient gases in liquid condition under pressure. Fractionation may also at least in part be dry without solvents and may then be aided as in the so-called Lanza process, by the use of surfactant aqueous dispersions for facilitating separation of liquid and solid phases during fractionation. Preferably the fractionation is carried out however in acetone at temperatures from 15 to -5°C or in hexane at temperatures from 10°C to -20 c C.
- acceptable solvent for example acetone, hexane or nitroparaffins or ambient gases in liquid condition under pressure.
- Fractionation may also at least in part be dry without solvents and may then be aided as in the so-called Lanza process, by the use of surfactant aqueous dispersions for facilitating separation of liquid and solid phases during fractionation.
- the fractionation is carried out however in ace
- Suitable enzymes which are active to catalyse interesterification only in the outer positions of glyceride molecules include, for example, Aspergillus niger and Mucor michei. These enzyme catalysts ensure that the unsaturated fatty acid residue in the 2-position of the glycerides of the lower-melting fraction remain unaffected by the interesterification, to provide a foundation for the production in that reaction of the desired symmetrical disaturated glycerides for the mid-fraction. Enzyme catalysts are particularly preferred for this process, but other catalysts may of course be adopted provided they show selective interesterification at the alpha-positions only.
- the interesterification reaction may be carried out in solvents which leave the catalyst unaffected, particularly hexane for enzyme catalysts, or without solvent and the reaction may be batchwise or continuous, the catalyst in the latter event being preferably fixed in a reaction vessel through which the reaction burden comprising the mixed upper- and lower-melting fractions are passed.
- Enzyme catalysts may be pre-activated by contact with water and they may be supported on a suitable carrier, as described in our patent specification GB 1577933.
- the water content may be obtained during the reaction, to predetermined limits in accordance with our patent specification (GB abandoned but EP 64855) by the use of humectants and/or other means for removing water from the reaction phase.
- the water content is preferably not more than 2% of the reaction mass, including solvent, and particularly not more than 1%.
- the water activity A w is preferably less than 50% during reaction.
- Enzyme catalysts may also however be used in polyhydric alcohol solution to maintain a very low water content.
- the water content is preferably low enough to minimise the extent of hydrolysis taking place with the production of partial glycerides. These may however be removed by selective adsorption means using silica-type adsorbents.
- Suitable fats include in particular palm oil but also shea, sal, pentadesma oil and of course cocoa butter itself, may all be processed in accordance with the present invention.
- Vegetable oils and fats are used since these contain an abundance of unsaturated fatty acid residues in the 2-position of their glycerides. Mixtures of oils and fats may be used and a fat which is deficient in trisaturated glycerides may be mixed with another containing them, or hydrogenated to provide sufficient for the interesterification reaction.
- the oils are refined before use as feedstock in the present invention and both neutralised and un-neutralised oils and fats may be used.
- the miscella containing 500ppm of water, was fed at 3 litres per hour through the reactor which contained 0.7 kg of catalyst.
- the residence time in the reactor was approximately 30 minutes and the reaction was carried out at 55°C.
- Solvent was distilled from the product which was then recrystallised from acetone, first at 20°C and then at 5°C to recover a mid-fraction, this is compared in the accompanying Table with a sample of mid-fraction obtained by crystallisation from unmodified palm oil.
- the composition is also given in the Table of the feedstock blend and its components.
- the olein and stearin fractions derived from the reaction product were found to be essentially similar in composition to these, the triglyceride analyses being determined by silver-phase HPLC methods.
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- Chemical & Material Sciences (AREA)
- General 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)
- Edible Oils And Fats (AREA)
- Fats And Perfumes (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
- This invention relates to hard butters and their preparation from edible fats.
- The eating quality of chocolate fat and other hard butter compositions containing cocoa butter is attributable to the presence in this fat of a high proportion of symmetrical disaturated triglycerides, principally the 2-oleyl glycerides of palmitic and stearic acid. Various substitute fats which have been proposed as an alternative to this expensive fat similarly contain more or less substantial quantities of these triglycerides. Processes for the production of cocoa butter substitutes and extender fats from these alternative sources generally include fractionation steps in which these more valuable glycerides are separated from others with less desirable melting attributes, notably trisaturated glycerides and mono-saturated and tri-unsaturated triglycerides, but also asymmetric disaturated glycerides, where these can be separated. The separation is usually effected by fractional crystallisation, particularly from a solvent such as acetone or hexane, the more highly saturated glycerides being removed in a higher-melting or stearin fraction, and the more highly unsaturated glycerides being removed in a lower-melting or olein fraction. These less desirable fractions may constitute as much as half the original fat and command a much lower premium than the hard butter fraction.
- Interesterification of fats and glyceride oils by methods using enzyme rearrangement catalysts have been described in GB 1577933. EP 69599 discloses fractionation of fats with rearrangement of the glycerides in the fractions obtained, followed if desired with fractionation of the product, to recovery more highly symmetrical glycerides, particularly for the preparation of cocoa butter replacement fats.
- The present invention proposes a process for the recovery of hard butters from vegetable fats, in which a vegetable fat containing substantial amounts of symmetrical disaturated triglycerides of C16 and C18 fatty acids is fractionated to recover the said glycerides by separating at least a more highly unsaturated, lower-melting olein fraction, which is mixed with a substantially saturated C16/C18 triglyceride fat, preferably by re-combining with an upper-melting , stearin fraction also separated from the vegetable fat, and the mixture interesterified in the presence of an enzyme catalyst which is preferably selectively active in the outer positions only of glycerides, i.e. the 1- and 1,3-positions or alpha-positions of the glycerides, to yield further quantities of symmetrical disaturated glycerides.
- Since the greatest proportion of the olein fraction consists of glycerides having an unsaturated fatty acid residue in the 2-position, all these are theoretically capable of conversion by interesterification under the influence of the enzyme catalyst to symmetrical disaturated triglycerides, provided only that sufficient glycerides are present in the blends, for example in the upper-melting or stearin fraction with which it is preferably combined, containing saturated fatty acid residues in the alpha or 1,3-positions that are vulnerable to the catalyst for effecting interesterification with the more highly unsaturated glycerides. For example, trisaturated glycerides may undergo interesterification with tri-unsaturated glycerides to provide 1-saturated di-unsaturated glycerides and these in turn to 1,3-disaturated glycerides, under the influence of the selective action of the catalyst. The trisaturated glycerides themselves convert correspondingly to asymmetric disaturated mono-unsaturated glycerides and symmetric di-unsaturated glycerides, i.e. 1,3-diunsaturated, 2-saturated glycerides.
- The interesterified glycerides may be separated as in conventional fractionation processes, to recover a fraction consisting essentially of symmetrical disaturated glycerides for use as a cocoa butter replacement fat. The more highly unsaturated glycerides in the interesterification mixture, including in particular the symmetrical 1,3-di-unsaturated glycerides, form a lower-melting oleine fraction. Any unreacted trisaturated glycerides may be separated if necessary in a top fraction, and recycled for further interesterification with any asymmetric disaturated glycerides, whether these appear in a stearin or olein fraction separated from the symmetrical disaturated fraction.
- The mixture of interesterified glycerides may be separately fractionated or recombined with feedstock in the fractionation step of the process. In a continuous operation in which feedstock is introduced to, and a symmetrical disaturated glyceride fraction removed from, circulation through fractionation and interesterification units, the feedstock may be introduced into either unit and may thus be fractionated first, in admixture with the entire interesterification output, or interesterified first together with the recycled interesterified fractions from which the symmetrical disaturated glycerides have been removed. In continuous operations in which feedstock is introduced and a symmetrical disaturated fraction removed, a purge may also be necessary of the symmetrical di-unsaturated glycerides to avoid build-up of this intractable material in the recycled composition. Rearrangement catalyst may also be used to convert this material and return it in a more tractable form, for example, a non-selective catalyst, a 2-selective catalyst, or one which is selectively active to saturated but not unsaturated fatty acid residues. A particular advantage of continuous operation is that the interesterification need be of relatively short duration since the interesterification can be incomplete for each pass through the unit. Enzyme interesterification is generally substantially slower than interesterification under the influence of inorganic catalysts which are also used at much higher temperatures. By continuous recycling however, the residence time in the interesterification step need be sufficient only to provide a significant improvement in the yield of the desired glycerides, without necessarily reaching equilibrium.
- The invention also includes recovery of the product from the rearrangement step, without fractionation or recycle, particularly for the preparation of hardstock fat which is then blended with liquid glyceride oils, to provide a composition suitable for margarine or other emulsion food spreads, or the fat may be used in ice-cream.
- Fractionation steps carried out in accordance with the invention may be conventional, either by solvent fractionation using acceptable solvent, for example acetone, hexane or nitroparaffins or ambient gases in liquid condition under pressure. Fractionation may also at least in part be dry without solvents and may then be aided as in the so-called Lanza process, by the use of surfactant aqueous dispersions for facilitating separation of liquid and solid phases during fractionation. Preferably the fractionation is carried out however in acetone at temperatures from 15 to -5°C or in hexane at temperatures from 10°C to -20cC.
- Suitable enzymes which are active to catalyse interesterification only in the outer positions of glyceride molecules include, for example, Aspergillus niger and Mucor michei. These enzyme catalysts ensure that the unsaturated fatty acid residue in the 2-position of the glycerides of the lower-melting fraction remain unaffected by the interesterification, to provide a foundation for the production in that reaction of the desired symmetrical disaturated glycerides for the mid-fraction. Enzyme catalysts are particularly preferred for this process, but other catalysts may of course be adopted provided they show selective interesterification at the alpha-positions only. The interesterification reaction may be carried out in solvents which leave the catalyst unaffected, particularly hexane for enzyme catalysts, or without solvent and the reaction may be batchwise or continuous, the catalyst in the latter event being preferably fixed in a reaction vessel through which the reaction burden comprising the mixed upper- and lower-melting fractions are passed. Enzyme catalysts may be pre-activated by contact with water and they may be supported on a suitable carrier, as described in our patent specification GB 1577933. The water content may be obtained during the reaction, to predetermined limits in accordance with our patent specification (GB abandoned but EP 64855) by the use of humectants and/or other means for removing water from the reaction phase. The water content is preferably not more than 2% of the reaction mass, including solvent, and particularly not more than 1%. In particular, the water activity Aw is preferably less than 50% during reaction. Enzyme catalysts may also however be used in polyhydric alcohol solution to maintain a very low water content. The water content is preferably low enough to minimise the extent of hydrolysis taking place with the production of partial glycerides. These may however be removed by selective adsorption means using silica-type adsorbents.
- Suitable fats include in particular palm oil but also shea, sal, pentadesma oil and of course cocoa butter itself, may all be processed in accordance with the present invention. Vegetable oils and fats are used since these contain an abundance of unsaturated fatty acid residues in the 2-position of their glycerides. Mixtures of oils and fats may be used and a fat which is deficient in trisaturated glycerides may be mixed with another containing them, or hydrogenated to provide sufficient for the interesterification reaction. Preferably the oils are refined before use as feedstock in the present invention and both neutralised and un-neutralised oils and fats may be used.
- Equal parts by weight of olein and stearin fractions obtained by the acetone fractionation of palm oil to remove a palm mid-fraction, were combined and the blend was dissolved in 3 times its own weight of hexane and interesterified using as interesterification catalyst a 1, 3-specific enzyme derived from a Mucor miehei organism supported on a diatomaceous earth in a packed bed reactor and activated with water before use. The miscella, containing 500ppm of water, was fed at 3 litres per hour through the reactor which contained 0.7 kg of catalyst. The residence time in the reactor was approximately 30 minutes and the reaction was carried out at 55°C.
- Solvent was distilled from the product which was then recrystallised from acetone, first at 20°C and then at 5°C to recover a mid-fraction, this is compared in the accompanying Table with a sample of mid-fraction obtained by crystallisation from unmodified palm oil. The composition is also given in the Table of the feedstock blend and its components. The olein and stearin fractions derived from the reaction product were found to be essentially similar in composition to these, the triglyceride analyses being determined by silver-phase HPLC methods.
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT85309086T ATE61390T1 (en) | 1984-12-17 | 1985-12-13 | EDIBLE FATS. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8431789 | 1984-12-17 | ||
GB8431789A GB2170506B (en) | 1984-12-17 | 1984-12-17 | Edible fats |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0185524A2 true EP0185524A2 (en) | 1986-06-25 |
EP0185524A3 EP0185524A3 (en) | 1987-07-15 |
EP0185524B1 EP0185524B1 (en) | 1991-03-06 |
Family
ID=10571300
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP85309086A Expired - Lifetime EP0185524B1 (en) | 1984-12-17 | 1985-12-13 | Edible fats |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP0185524B1 (en) |
JP (1) | JPS61179299A (en) |
AT (1) | ATE61390T1 (en) |
AU (1) | AU568035B2 (en) |
DE (1) | DE3582030D1 (en) |
GB (1) | GB2170506B (en) |
SE (1) | SE8505956L (en) |
ZA (1) | ZA859618B (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4883684A (en) * | 1988-07-01 | 1989-11-28 | The Procter & Gamble Company | Functional hardstock fat composition |
EP0457401A1 (en) * | 1990-05-17 | 1991-11-21 | Unilever N.V. | Mid-fraction production by fractional crystallization with stearin and olein fraction recycling to interesterification |
EP0519542A1 (en) * | 1991-06-17 | 1992-12-23 | Unilever N.V. | Combined fractionation, refining and interesterification process |
US5288619A (en) * | 1989-12-18 | 1994-02-22 | Kraft General Foods, Inc. | Enzymatic method for preparing transesterified oils |
EP0882797A2 (en) * | 1997-06-04 | 1998-12-09 | Unilever N.V. | Preparation of symmetrical triglycerides aba |
WO2002041698A1 (en) * | 2000-11-21 | 2002-05-30 | Unilever N.V. | Edible spread containing a natural fat phase |
EP1676484A1 (en) * | 1996-06-26 | 2006-07-05 | Loders Croklaan B.V. | Non-trans, non-temper filling fats |
US7442531B2 (en) * | 2003-07-09 | 2008-10-28 | The Nisshin Oillio Group, Ltd. | Method for producing symmetric triglycerides |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL8501957A (en) * | 1985-07-09 | 1987-02-02 | Unilever Nv | FATS AND EDIBLE EMULSIONS, IN PARTICULAR DIET WITH HIGH CONTENT OF CIS-POLY-UNSATURATED FATTY ACIDS. |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2035359A (en) * | 1978-11-21 | 1980-06-18 | Fuji Oil Co Ltd | Producing a cacao butter substitute by transesterification of fats and oils |
EP0034065A2 (en) * | 1980-02-07 | 1981-08-19 | Unilever Plc | Cocoa butter substitute |
EP0069599A1 (en) * | 1981-07-08 | 1983-01-12 | Unilever Plc | Edible fat process |
EP0079986A1 (en) * | 1981-11-19 | 1983-06-01 | Fuji Oil Company, Limited | Method for the modification of fats and oils |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1418759A1 (en) * | 1960-03-18 | 1969-05-08 | E F Drew & Co Inc | Method and apparatus for isolating a hard fat product from a glycero oil |
JPS57111398A (en) * | 1980-12-29 | 1982-07-10 | Asahi Denka Kogyo Kk | Ester exchange process for oils and fats |
AU544682B2 (en) * | 1981-11-18 | 1985-06-13 | Fuji Oil Company Limited | Method for modification of fats and oils |
IE54838B1 (en) * | 1982-04-30 | 1990-02-28 | Unilever Plc | Improvements in and relating to interesterification of triglycerides of fatty acids |
-
1984
- 1984-12-17 GB GB8431789A patent/GB2170506B/en not_active Expired
-
1985
- 1985-12-13 EP EP85309086A patent/EP0185524B1/en not_active Expired - Lifetime
- 1985-12-13 DE DE8585309086T patent/DE3582030D1/en not_active Expired - Fee Related
- 1985-12-13 AT AT85309086T patent/ATE61390T1/en active
- 1985-12-16 AU AU51275/85A patent/AU568035B2/en not_active Expired - Fee Related
- 1985-12-16 SE SE8505956A patent/SE8505956L/en not_active Application Discontinuation
- 1985-12-17 JP JP60285955A patent/JPS61179299A/en active Pending
- 1985-12-17 ZA ZA859618A patent/ZA859618B/en unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2035359A (en) * | 1978-11-21 | 1980-06-18 | Fuji Oil Co Ltd | Producing a cacao butter substitute by transesterification of fats and oils |
EP0034065A2 (en) * | 1980-02-07 | 1981-08-19 | Unilever Plc | Cocoa butter substitute |
EP0069599A1 (en) * | 1981-07-08 | 1983-01-12 | Unilever Plc | Edible fat process |
EP0079986A1 (en) * | 1981-11-19 | 1983-06-01 | Fuji Oil Company, Limited | Method for the modification of fats and oils |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4883684A (en) * | 1988-07-01 | 1989-11-28 | The Procter & Gamble Company | Functional hardstock fat composition |
US5288619A (en) * | 1989-12-18 | 1994-02-22 | Kraft General Foods, Inc. | Enzymatic method for preparing transesterified oils |
EP0457401A1 (en) * | 1990-05-17 | 1991-11-21 | Unilever N.V. | Mid-fraction production by fractional crystallization with stearin and olein fraction recycling to interesterification |
EP0519542A1 (en) * | 1991-06-17 | 1992-12-23 | Unilever N.V. | Combined fractionation, refining and interesterification process |
EP1676484A1 (en) * | 1996-06-26 | 2006-07-05 | Loders Croklaan B.V. | Non-trans, non-temper filling fats |
EP0882797A2 (en) * | 1997-06-04 | 1998-12-09 | Unilever N.V. | Preparation of symmetrical triglycerides aba |
EP0882797A3 (en) * | 1997-06-04 | 2000-09-27 | Unilever N.V. | Preparation of symmetrical triglycerides aba |
WO2002041698A1 (en) * | 2000-11-21 | 2002-05-30 | Unilever N.V. | Edible spread containing a natural fat phase |
US6777018B2 (en) | 2000-11-21 | 2004-08-17 | Lipton, Division Of Conopco, Inc. | Edible spread containing a natural fat phase |
US7118773B2 (en) | 2000-11-21 | 2006-10-10 | Lipton, Divison Of Conopco, Inc. | Edible spread containing a natural fat phase |
US7442531B2 (en) * | 2003-07-09 | 2008-10-28 | The Nisshin Oillio Group, Ltd. | Method for producing symmetric triglycerides |
Also Published As
Publication number | Publication date |
---|---|
EP0185524B1 (en) | 1991-03-06 |
GB2170506B (en) | 1989-08-23 |
AU568035B2 (en) | 1987-12-10 |
JPS61179299A (en) | 1986-08-11 |
AU5127585A (en) | 1986-06-26 |
ATE61390T1 (en) | 1991-03-15 |
ZA859618B (en) | 1987-08-26 |
SE8505956D0 (en) | 1985-12-16 |
GB8431789D0 (en) | 1985-01-30 |
EP0185524A3 (en) | 1987-07-15 |
GB2170506A (en) | 1986-08-06 |
DE3582030D1 (en) | 1991-04-11 |
SE8505956L (en) | 1986-06-18 |
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