WO2006108754A1 - Le procede de recuperation et d'utilisation de diglycerides - Google Patents

Le procede de recuperation et d'utilisation de diglycerides Download PDF

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Publication number
WO2006108754A1
WO2006108754A1 PCT/EP2006/060833 EP2006060833W WO2006108754A1 WO 2006108754 A1 WO2006108754 A1 WO 2006108754A1 EP 2006060833 W EP2006060833 W EP 2006060833W WO 2006108754 A1 WO2006108754 A1 WO 2006108754A1
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Prior art keywords
process according
fractionation
diglyceride
diglycerides
glycerol
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PCT/EP2006/060833
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English (en)
Inventor
Flemming SPARSØ
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Danisco A/S
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Publication of WO2006108754A1 publication Critical patent/WO2006108754A1/fr

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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
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/08—Refining
    • C11C1/10—Refining by distillation
    • 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
    • C11B3/12—Refining fats or fatty oils by distillation
    • 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

Definitions

  • the invention relates to a process for recovering diglycerides.
  • the invention also relates to the use of the process for producing of target diglycerides according to customer requirements.
  • the invention is advantageously used for producing diglyceride distillate with a diglyceride content of 80% or more.
  • partial glycerides depend on the ratio and type of fatty acid chains in the molecule. Therefore, partial glycerides are used in several ways in the food, nutraceutical, pharmaceutical and plastic/polymer industry depending on their properties.
  • Partial glycerides are compounds of the formula
  • R 1 , R 2 , and R 3 represent hydrogen and the other represent fatty acid residues.
  • Partial glycerides with one fatty acid residue are monoglycerides and partial glycerides with two iatty acid residues are diglycerides.
  • Glycerides having fatty acid residues at all three R positions are triglycerides. Most natural fats of both vegetable and animal origin are triglycerides.
  • EP 0307154 discloses an enzymatic method for preparing a diglyceride from a saturated or unsaturated fatty acid having 4 to 22 carbon atoms, or a lower alcohol ester thereof, and glycerol, which comprises the step of reacting at least 1.5 moles of the fatty acid or lower alcohol ester thereof with one mole of glycerol in the presence of an immobilized lipase or an endo-lipase that reacts with glycerides preferentially at their 1st or 3rd position, while water or lower alcohol produced by the reaction is removed under reduced pressure.
  • WO 03/060139 discloses an enzymatic process for the production of diglycerides which comprises reacting a fatty acid or lower alkyl ester thereof with glycerin in the presence of an immobilized partial glyceride lipase while removing water or lower alcohol, which is generated upon reaction, out of the reaction system.
  • EP 10005517 disclosed a process for producing diglycerides comprising the steps of conducting a partial hydrolysis of a fat or oil to obtain a partial hydro lyzate having 67 to 96 % by weight of decomposed fatty acids and being inhibited from discolouring and, without distillation, then esterifying the partial hydrolyzate with glycerol.
  • WO 03/029392 discloses a chemical method for producing 1,3-diglyceride oils.
  • the method comprises mixing triglyceride containing oil with glycerol and a catalyst comprising an alkali metal salt or alkali earth metal salt of a mono-carboxylic acid or a dicarboxylic acid, or a mixture thereof, to achieve glycerolysis, wherein 1,3-diglyceride oil is produced.
  • the diglyceride oil product is cleaned by the removal of monoglycerides by molecular distillation at 200 to 210 °C and 0.001 to 0.010 millibars (0.1-1 Pa).
  • an additional molecular distillation step could increase the purity and improve the colour of the diglyceride product by removing a triglyceride residue containing catalyst.
  • the present inventors have found that the process described by Erciyes et al. is difficult to operate on an industrial scale since there is a tendency for the pressure to rise above the indicated low level. It has now been found that it is possible to provide an industrially advantageous process which does not need to perform the distillation at the suggested low pressure. On the contrary, the inventors have found that when diglycerides are distilled on an industrial scale, a technically more advantageous process is provided by the use of a higher pressure than in said prior art. Thus, the present process comprises an industrially useful process for recovering diglycerides. Summary of the invention
  • the present invention concerns a process for recovering diglycerides.
  • the process is suitable for being operated on an industrial scale.
  • the process is defined in the appended claims.
  • the present invention also concerns the industrial use of said process for supplying customers with their desired target diglycerides in a technically feasible way.
  • the use is defined in the appended claims.
  • the invention also relates to a process for producing a diglyceride distillate with a minimum diglyceride content of 80 %, preferably 85 %, more preferably 90 % by weight. It is also possible to recover monoglycerides as a further product of the present fractionation process.
  • the contents of the claims are considered as being part of this specification.
  • diglycerides are recovered by fractionating a glyceride mixture of mono-, di- and triglycerides on an industrial scale in at least two fractionation steps at temperatures above 150 0 C and pressures between 0.15 and 10 Pa, wherein one of said steps separates triglycerides from mono- and/or diglycerides at a temperature between 220 and 300 0 C and the other one of said steps separates monoglycerides from di- and/or triglycerides at a temperature between 150 and 250 0 C, and recovering diglycerides as a product of said fractionation steps.
  • the triglyceride-separating step is typically performed at a temperature of 240 to 280 0 C.
  • the monoglyceride-separating step is typically performed at a temperature of 180 to 240 0 C.
  • Target diglycerides as well as optional monoglycerides having different content of fatty acids are recoverable from said two fractionation means, respectively, as end products.
  • the process of the invention may, in addition to the actual diglyceride recovery steps, also contain an additional purification step in order to increase the purity of the diglyceride product.
  • this purification step preferably comprises a third fractionation step, which is performed on the diglyceride product.
  • the third fractionation may remove monoglyceride or triglyceride.
  • the fractionation is performed at a temperature of 150 to 250 0 C, preferably 180 to 240 0 C, in order to effectively remove monoglycerides from said diglyceride product.
  • At least one of said fractionation steps is performed in a fractionation means, such as a distillation unit, like a short path distillation column, a falling film short path evaporator, a centrifugal still and/or a high vacuum wiped film evaporator, preferably a short path distillation column.
  • a fractionation means such as a distillation unit, like a short path distillation column, a falling film short path evaporator, a centrifugal still and/or a high vacuum wiped film evaporator, preferably a short path distillation column.
  • Fractionation steps are preferably performed in one or in two or more separate short path distillation columns.
  • a fluid from one of the columns is treated in another fractionation means at a temperature above 150 °C.
  • the target diglycerides, as well as optional monoglycerides are obtained in high purity.
  • the composition of the feed mixture is preferably designed to provide a glyceride mixture containing the desired diglyceride and/or monoglyceride molecules.
  • the specific fractionation process of the invention provides the final diglycerides for the intended use, such as for food ingredient, nutritional, nutraceutical and for pharmaceutical use, use as additive for plastics and polymers as well as for other uses.
  • the process of this invention makes it possible to produce diglycerides in a substantially pure form for the interested industry to test. In this way the present invention makes it possible to provide new diglycerides, which have potentially useful and surprising properties.
  • a mixture of glycerides is fractionated in order to obtain the desired diglycerides.
  • the mixture of glycerides used as a feed stream in the present invention may be prepared in any conventional manner.
  • the mixture may be provided by transesterification of glycerol and triglycerides in a reaction system using conventional chemistry and/or enzymatic process, by enzymatic or chemical esterification of glycerol with fatty acids.
  • the person skilled in the art will be aware of other ways to provide mixtures of partial glycerides for the feed mixture.
  • the glycerides comprising the feed stream may be provided e.g. by transesterification of glycerol and triglycerides containing the desired fatty acid moieties of the desired product partial glycerides.
  • the mixture obtained from a conventional or enzymatic esterification process contains a mixture of glycerides comprising a different number of fatty acids depending on the feeds used for the process as well as on the used process itself.
  • the composition of the feed stream may be optimised by selecting the ratio between glycerol and triglycerides in the reaction to provide the highest yield in kg/hr of the desired product in the fractionation according to the invention.
  • the present process requires the removal of glycerol prior to the actual fractionation of the partial glycerides.
  • enzymatic techniques it is, for instance, possible to obtain partial glycerides containing polyunsaturated fatty acids.
  • the enzymatic techniques also make it possible to provide a more exact distribution of partial glycerides.
  • the enzymatic techniques make it possible to produce partial glyceride mixtures wherein the concentration of essential fatty acids e.g. polyunsaturated fatty acids like linoleic, ⁇ -linolenic acid, DHA and EPA is higher than in a partial glyceride mixture owing from chemical transesterification or esterification reactions.
  • the composition of the final product is controlled mainly by the temperature used in the fractionation steps.
  • the monoglyceride, diglyceride and triglyceride molecules are separated from the mixture in an order and in fractions which depend on the temperature used in the fractionation step in question.
  • the number of the fractionation steps is selected according to the desired purity of diglyceride end product.
  • the fatty acids in the glyceride mixture are derived from natural or hydrogenated or selectively hydrogenated oils and fats including oils and fats having vegetable, animal or micro organism origin or mixtures thereof.
  • the fatty acids of the present invention are preferably C8 to C30 saturated or unsaturated, cyclic or branched or hydroxyl fatty acids. More preferably, the fatty acids are saturated C 8 to C30 acids, most preferably saturated C12 to C24 acids.
  • the acids may be selected according to the desired known properties of the product which may be low caloric or other nutritional use, pharmaceutical use, use in plastics etc. The acids may also be selected according to a pattern for obtaining target diglycerides with unknown properties which may prove beneficial in any field of industry.
  • Saturated long chain fatty acids include e.g octanoic, decanoic, lauric, myristic, palmitic, stearic, arachidicic, behenic, lignoceric acid, etc.
  • Unsaturated long chain fatty acids include palmitoleic, oleic, gadoleic, arachidonic acids and polyunsaturated fatty acids (PUFA) such as linoleic, ⁇ -linolenic, DHA (C22:6 ⁇ 3) and EPA (C20:5 ⁇ 3) etc.
  • PUFA polyunsaturated fatty acids
  • Fatty acids included in glycerides from animal or vegetable oils and fats and micro-organisms such as lard, tallow, palm, rapeseed, soybean, cottonseed, linseed, sunflower, coconut, palm kernel, fish, algae etc.
  • the fat and oils may be hydrogenated, selectively hydrogenated or non hydrogenated.
  • Preferable fatty acids are Cl 2 to C24 acids, like palmitic, stearic and behenic acids.
  • the diglyceride used in the specification and claims means a partial glyceride having two fatty acid chains.
  • the monoglyceride contains one fatty acid chain.
  • the triglyceride has three fatty acid chains.
  • At least one of the fractionation steps is preferably performed at a temperature above 220 °C, preferably between 220 and 300 °C, whereby the yield of the monoglyceride and diglyceride fractions is improved and whereby the diglyceride concentration of the diglyceride fraction is increased.
  • the temperature used in said step is preferably between 240 and 280 °C.
  • the pressure in the fractionation step is lowered, preferably to a value between 0.15 and 10 Pa more preferably to a value of 0.15 to 5 Pa.
  • the fractionation is performed in two steps which improves the product purity and enables obtaining distilled products having more than 80 % by weight diglycerides at a high yield.
  • the glyceride percentage in the present specification and claims is calculated by weight of the total product, while in the prior art, diglyceride purity is often calculated as the percentage of diglyceride based on the sum of diglyceride and triglyceride.
  • the feed glyceride mixture is tailored accordingly to provide a suitable end product after fractionation.
  • the present invention enables the obtaining of a product having a purity, which is higher than the purity obtainable in the prior art.
  • the purity of the monoglyceride and/or diglyceride product of the present invention is preferably at least about 80 %, more preferably at least about 85 %, most preferably at least about 90 % by weight of the respective glyceride product.
  • a mixture of glycerides obtainable from most conventional partial glyceride production processes is suitable for being treated in the process according to the present invention.
  • the mixture contains glycerol, this should be substantially removed before the mixture is subjected to the process of the invention.
  • the mono-, di- and triglycerides are each separated from the mixture in an order, which depends on the flow design of the process as well as on the temperatures used in the process.
  • the process according to the invention may be designed using conventional separation and fractionation equipment, such as distillation means and evaporators. Short path distillation units are preferred as separation means.
  • the process preferably also includes strippers for further purification of the products.
  • the two fractionation steps are performed in two separate fractionation means. It is, however, also possible to provide the two fractionation means in one and the same physical equipment. Thus it is possible to provide one short path distillation column, which has two or more separate heat sections. The separate sections may operate at different temperatures, thus providing distinct fractionation steps. The columns and/or sections may be provided with separate distillate residue collection points for recovery of the different triglycerides.
  • the fractionation is most preferably performed in at least two separate short path distillation columns. Depending on the desired product composition the distillation is performed at a selected temperature and with a flow design that gives the desired composition. In case short path distillation columns are used in the process according to the present invention, the fractionation is generally operated according to one of two main principles.
  • both the mono- and the diglycerides are distilled off on the first column at temperatures above about 220 °C, preferably between 240 and 280 °C and then the monoglycerides are removed from the distillate on the second column at temperatures from about 150 to 250 °C, preferably between 180 and 240 °C.
  • the monoglycerides and diglycerides obtained are preferably each further purified in separate steps after the fractionation.
  • Another preferred way to operate the columns of the process according to the invention is to distil the majority of the monoglycerides on the first column. Then the diglycerides are distilled from the remaining mixture on the second column. A diglyceride content of more than about 80 %, preferably more than 85 %, more preferably above about 90 % by weight is obtained with the rest being substantially monoglycerides and/or triglycerides.
  • the temperature in the second column is between 220 and 300 °C, preferably between 240 and 280 °C. A higher purity of the diglyceride is obtained if a third fractionation step is used.
  • the respective monoglyceride and diglyceride products from the fractionation means are preferably stripped with water vapour in packed columns in order to ensure a good organoleptic quality and remove any traces of glycerol.
  • the present invention makes it possible to design diglycerides, and optionally monoglycerides, for any desired need and also for testing for potential beneficial properties.
  • the process of the invention can thus be used for providing of target diglycerides and/or monoglycerides having a controlled composition, said use comprising the steps of
  • triglycerides are separated at a temperature of 220 to 300 0 C, typically at 240 to 280 0 C.
  • Monoglycerides are separated at a temperature of 150 to 250 0 C, typically at 180 to 240 0 C.
  • the target diglycerides are then recovered at high purity.
  • the target di- and/or monoglyceride(s) is/are preferably recovered at a purity above 80 %, more preferably above 85 %, most preferably above 90 % by weight.
  • the target fatty acid(s) and/or composition of the target di- and/or monoglyceride are also defined in response to customer requirements.
  • the partial glycerides obtained by the present invention may be used e.g. in nutritional compositions in nutraceuticals and pharmaceuticals, etc.
  • the partial glycerides may also be used in various food industry applications, e.g. in low caloric products, in baked products, cooking oils, coatings and snack food products, as well as for emulsifiers, plasticizers, antistatic additive for plastic/polymers etc.
  • the diglyceride obtained may be mixed with one or more ingredients for end products, and if desired the mixed diglyceride and ingredient(s) are processed into a respective end product.
  • the partial glycerides of the present invention may be incorporated in a composition comprising a thermoplastic polymer.
  • a typical thermoplastic polymer may be or comprise a polycarbonate.
  • Polycarbonates are understood to include both homo- and copolycarbonates as well as aromatic and non-aromatic polycarbonates.
  • the polycarbonates may be linear or branched. A portion of the carbonate groups in the polycarbonate may be replaced by aromatic dicarboxylic acid ester groups.
  • the partial glycerides/products of the present invention may be used as - or in the preparation of - a food.
  • the term "food” is used in a broad sense - and covers food for humans as well as food for animals (i.e. a feed). In a preferred aspect, the food is for human consumption.
  • the term “food ingredient” or “feed ingredient” includes a formulation, which is or can be added to functional foods or foodstuffs as a nutritional supplement.
  • functional food means food, which is capable of providing not only a nutritional effect, but is also capable of delivering a further beneficial, preferably health effect to consumer.
  • nutraceuticals Some functional foods are nutraceuticals.
  • the term "nutraceutical” means a food which is capable of providing not only a nutritional effect and/or a taste satisfaction, but is also capable of delivering a therapeutic (or other beneficial) effect to the consumer. Nutraceuticals cross the traditional dividing lines between foods and medicine.
  • the partial glycerides/products of the present invention may also be used in pharmaceutical preparations or for combination into foodstuffs in order to provide some pharmaceutical effect.
  • the partial glycerides/products of the present invention may be used in conjunction with one or more of: a pharmaceutically acceptable carrier, a pharmaceutically acceptable diluent, a pharmaceutically acceptable excipient, a pharmaceutically acceptable adjuvant, a pharmaceutically active ingredient.
  • emulsifier refers to an ingredient (e.g. a food product ingredient) that prevents the separation of emulsions.
  • the present invention enables the production of novel compounds having properties, which are not yet known. Because the present invention provides new possibilities to obtain partial glycerides with desired composition, new and hitherto unknown partial glycerides with new and surprising properties may be produced. Thus, the present invention makes it possible to prepare partial glycerides which could be beneficial for lowering cholesterol absorption, reducing fatty tissue, reducing tumor growth rate, enhancing renal, liver or colon function or reducing the risk of infections, etc.
  • Figure 1 discloses a fractionation system for the process according to the present invention.
  • Figure 2 discloses another fractionation system for the process according to the present invention.
  • a mixture 1 of glycerides obtained from a conventional or non-conventional reaction system is supplied to a first stripping column 2 where substantially all of the glycerol is removed from the reaction mixture 1 at a temperature of about 150-240 °C and a pressure of about 10-1000 Pa depending on the amount of glycerol in the reaction mixture 1.
  • a temperature of about 150-240 °C and a pressure of about 10-1000 Pa depending on the amount of glycerol in the reaction mixture 1.
  • about 1-30 % by weight preferably about 5-20 % of the mixture is stripped off. It is preferred to remove as much as possible of the glycerol and the feed to the next step generally contains less than 2 weight-% preferably less than 1 weight-% glycerol most preferably less than 0.5 weight-%.
  • the stripped glycerol 3 may be recycled back to the process for preparing the mixture 1 of partial glycerides.
  • the glycerol-stripped mixture of glycerides from the first stripping column 2 is used as a feed mixture 4 according to the invention.
  • the feed mixture is first fed into a first short path distillation unit 5.
  • the temperature of the feed is preferably adjusted to about 140-200 °C before feeding into the short path distillation unit.
  • the first short path distillation is performed at a temperature of 220 °C to 300 °C, preferably at a temperature of 240 °C to 280 °C in order to distill both the mono- and diglycerides.
  • the pressure in the distillation unit is about 0.15-10 Pa. Triglycerides are not distilled under these conditions and the residue 6 containing the triglycerides is removed and may be recycled as a feed into the reaction for preparing the mixture 1 of partial glycerides.
  • the distillate 7 containing both mono- and diglycerides is then supplied to a second short path distillation unit 8.
  • the temperature used in the second short path distillation unit is about 150- 250 °C, preferably 180-240 °C, in order to distill the monoglycerides.
  • the pressure in the distillation unit is about 0.15-10 Pa.
  • the residue 10 from the second short path distillation unit 8 is recovered as a product containing mostly diglycerides. It is preferably fed to a second stripping column 14 through a heat exchanger. This stripping unit purifies the diglycerides and removes the odors.
  • the temperature of the column is about 180-240 °C and the pressure is about 10-1000 Pa.
  • the residue 15 contains finished product comprising diglycerides at a high yield and desired purity.
  • the distillate 9 from the second short path distillation unit 8 may be supplied into a third stripping column 11 for the purification of the product.
  • the temperature of such a column is about 180-240 °C and the pressure is about 10-1000 Pa.
  • the residue 13 contains finished product comprising monoglycerides at a high yield and desired purity.
  • a mixture 1 of partial glycerides obtained from a conventional or non-conventional reaction system is supplied to a first stripping column 2 where substantially all glycerol is removed from the reaction mixture 1 at a temperature of about 150-240 °C depending on the amount of glycerol in the reaction mixture.
  • the glycerol-stripped mixture of glycerides is used as a feed mixture 4 to a first short path distillation unit 5.
  • the temperature of the feed is adjusted to about 140-200 °C.
  • the first short path distillation is performed at a temperature of about 180-240 °C.
  • the pressure in the distillation unit is about 0.15-10 Pa.
  • the monoglycerides are distilled off the mixture at this stage.
  • the distillate 7 from the first short path distillation having a temperature of about 40-100 °C may be supplied to a second stripping column 14 for purification.
  • the temperature of the column is about 180-240 °C and the pressure is about 10-1000 Pa.
  • the distillate is removed and the residue 15 contains finished product comprising purified monoglycerides.
  • the residue 6 from the first short path distillation unit 5 is heated to a temperature of about 140- 200 °C. It is then supplied to a second short path distillation unit 8.
  • the temperature used in the second short path distillation unit is about 220-300 °C, preferably about 240-280 °C.
  • the pressure in the distillation unit is about 0.15-10 Pa.
  • the residue 10 contains the triglycerides which may be discarded or recycled as a feed into the reaction for preparing the mixture 1 of partial glycerides.
  • the distillate 9 from the second short path distillation unit 8, having a temperature of about 40- 100 °C may be supplied to a third stripping column 11 for purification.
  • the temperature of the column is about 180-240 °C and the pressure is about 10-1000 Pa.
  • the stripped part 12 is removed and the residue 13 contains finished product comprising diglycerides.
  • the temperature and/or flow of the distillation are selected depending on the desired product composition. This is controlled by the distillation cut defined as the distillate flow rate in kg/hr divided by the feed flow rate in kg/hr.
  • the mixture of glycerides used as a feed into the fractionation process affects the amount of different partial glycerides obtained as well.
  • a glyceride mixture based on a transesterification of glycerol and safflower oil having the following composition (%) after substantially removing the excess glycerol: glycerol 0.3 free fatty acid 0.6 monoglyceride 42.8 diglyceride 45.2 triglyceride 11.5
  • the rest was a residue with the following composition (%): glycerol 0.0 free fatty acid 0.1 monoglyceride 1.8 diglyceride 29.3 triglyceride 68.9
  • the distillate was treated further in a second distillation in a short path distillation column at 205 0 C and a pressure of 0.15 Pa. 52.4 % was removed as distillate.
  • the composition (%) of the distillate was glycerol 0.3 free fatty acid 0.1 monoglyceride 96.1 diglyceride 3.5 triglyceride 0.0
  • the residue from the second fractionation was recovered as a high purity diglyceride product.
  • the distillate was treated further in a second distillation in a short path distillation column at 205 0 C and a pressure of 0.15 Pa. 52.8 % was removed as distillate.
  • the composition (%) of the distillate was glycerol 0.3 free fatty acid 0.6 monoglyceride 89.2 diglyceride 9.9 triglyceride 0.0
  • the residue from the second fractionation was recovered as a high purity diglyceride product.
  • the residue was treated further in a second distillation in a short path distillation column at 245 0 C and a pressure of 0.3 Pa. 47.5 % was removed as distillate.
  • the composition (%) of the distillate was glycerol 0.0 free fatty acid 0.2 monoglyceride 16.3 diglyceride 83.4 triglyceride 0.1
  • the distillate from the second fractionation was recovered as a diglyceride product.
  • a glyceride mixture substantially free of glycerol was subjected to a two-step fractionation in accordance with the invention.
  • the glyceride mixture was obtained from a reaction between glycerol and fully hydrogenated rapeseed oil (consisting approximately 90% stearic acid).
  • the first fractionation the partial glyceride mixture with the following composition (in weight
  • This product was recovered as a diglyceride product.
  • the residue from the second fractionation had the following composition (%): monoglyceride 0 diglyceride 50 triglyceride 50
  • the diglyceride product obtained in Example 2 and containing 87.4 % by weight of diglyceride and 10.0 % by weight of triglyceride is subjected to a third fractionation step to increase its purity.
  • the fractionation is performed in a short path distillation column at a temperature of 280 °C and a pressure of 0.2 Pa. 55 % of the feed is recovered as a high purity diglyceride distillate having a diglyceride content of 95 % by weight.
  • the diglyceride product obtained in Example 2 and containing 87.4 % by weight of diglyceride and 2.5 % by weight of monoglyceride is subjected to a third fractionation step to increase its purity.
  • the fractionation is performed in a short path distillation column at a temperature of 200 °C and a pressure of 0.15 Pa. 90 % of the feed is recovered as a high purity diglyceride residue having a diglyceride content of 89 % by weight.

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Abstract

La présente invention porte sur un procédé de récupération de diglycérides qui consiste à fractionner un mélange glycéride de mono, -di et triglycérides, à échelle industrielle, dans au moins deux étapes de fractionnement, à des températures supérieures à 150 °C et à des pressions comprises entre 0,15 et 10 Pa. L'une des étapes consiste à séparer les triglycérides des mono- et/ou diglycérides, et une autre des étapes consiste à séparer les monoglycérides des di- et/ou triglycérides. Les diglycérides sont récupérés sous forme d'un produit des étapes de fractionnement. Le procédé peut être utilisé dans l'obtention de diglycérides cibles ayant une composition régulée d'acides gras.
PCT/EP2006/060833 2005-04-08 2006-03-17 Le procede de recuperation et d'utilisation de diglycerides WO2006108754A1 (fr)

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FI20055158 2005-04-08
FI20055158A FI20055158A (fi) 2005-04-08 2005-04-08 Menetelmä diglyseridien talteenottamiseksi ja sen käyttö

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011021107A2 (fr) 2009-08-20 2011-02-24 Danisco A/S Procédé
WO2020058898A1 (fr) * 2018-09-20 2020-03-26 Sabic Global Technologies B.V. Préparation d'acides gras à partir d'huiles
CN112661645A (zh) * 2020-12-31 2021-04-16 佳力士添加剂（海安）有限公司 一种高纯度单甘酯的提纯方法及装置

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WO2011021107A2 (fr) 2009-08-20 2011-02-24 Danisco A/S Procédé
US8846793B2 (en) 2009-08-20 2014-09-30 Dupont Nutrition Biosciences Aps Process
WO2020058898A1 (fr) * 2018-09-20 2020-03-26 Sabic Global Technologies B.V. Préparation d'acides gras à partir d'huiles
CN112661645A (zh) * 2020-12-31 2021-04-16 佳力士添加剂（海安）有限公司 一种高纯度单甘酯的提纯方法及装置

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