EP2627423A1 - Device and method for distilling temperature-sensitive substances - Google Patents

Device and method for distilling temperature-sensitive substances

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Publication number
EP2627423A1
EP2627423A1 EP11763590.4A EP11763590A EP2627423A1 EP 2627423 A1 EP2627423 A1 EP 2627423A1 EP 11763590 A EP11763590 A EP 11763590A EP 2627423 A1 EP2627423 A1 EP 2627423A1
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EP
European Patent Office
Prior art keywords
distillation
dha
epa
hpa
film evaporator
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.)
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Application number
EP11763590.4A
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German (de)
French (fr)
Inventor
Peter Horlacher
Dieter Hietsch
Jörg SCHWARZER
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Cognis IP Management GmbH
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Cognis IP Management GmbH
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Priority to EP11763590.4A priority Critical patent/EP2627423A1/en
Publication of EP2627423A1 publication Critical patent/EP2627423A1/en
Withdrawn legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/14—Fractional distillation or use of a fractionation or rectification column
    • B01D3/143—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step
    • B01D3/148—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step in combination with at least one evaporator
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D1/00—Evaporating
    • B01D1/06—Evaporators with vertical tubes
    • B01D1/065—Evaporators with vertical tubes by film evaporating

Definitions

  • the present invention relates to a device for the distillation of mixtures containing temperature-sensitive substances, the device comprising a thin-film evaporator and a fractionating column, and wherein the disproportionateierkolonne is placed on the distillate output of Dünn fürverdarnpfers, and wherein the disproportionateierkolonne has at least 3 theoretical plates, and wherein the pressure loss of the fractionation column in operation at a F-factor of 1 Pa 1/2 is a maximum of 3 hPa (3 mbar). Furthermore, the present invention relates to a method for the distillation of mixtures containing temperature-sensitive substances, characterized in that the method is carried out in the device according to the invention.
  • the polyunsaturated fatty acids and their derivatives for example their methyl esters or ethyl esters, are of interest.
  • Polyunsaturated fatty acids are fatty acids containing at least two double bonds. These include, for example, linoleic acid, alpha-linolenic acid, gamma-linolenic acid and arachidonic acid. Polyunsaturated fatty acids have at least five carbon atoms. In the following, polyunsaturated fatty acids are understood in particular to mean those which have at least six C atoms. Omega-3 fatty acids are also among the polyunsaturated fatty acids. EPA and DHA are special omega-3 fatty acids.
  • EPA is the abbreviation for (5Z, 8Z, 11Z, 14Z, 17Z) -eicosa-5,8,11,14,17-pentaenoic acid.
  • DHA is the abbreviation for (4Z, 7Z, 10Z, 13Z, 16Z, 19Z) docosa-4,7, 10,13,16,19-hexaenoic acid.
  • Polyunsaturated fatty acids may be included as part of Food, dietary supplements or so-called functional foods. They can also be used in the pharmaceutical sector, for example in the case of EPA and DHA for the therapy or prophylaxis of coronary heart disease. They are usually used as glycerol esters, ie as part of fats. But you can also as free fatty acids or in the form of esters, eg. As ethyl esters, are used.
  • Polyunsaturated fatty acids especially EPA and DHA may be derived from natural sources, e.g. B. from fish oil, are obtained.
  • natural sources e.g. B. from fish oil
  • processes for the enrichment of polyunsaturated fatty acids, in particular of EPA and / or of DHA are required, by means of which polyunsaturated fatty acids, in particular EPA and / or DHA natural sources such.
  • B. fish oil can be enriched.
  • DE 969103 discloses the accumulation of EPA and DHA from solid sodium soaps by using organic solvents in which the sodium soaps are not soluble but the other adjunct substances.
  • GB 719 513 discloses a process in which soaping of fats and oils gives soaps which in turn are converted into solid substances. Then the unsaturated soaps are dissolved with water-miscible organic solvents.
  • the European patent application with the application number 10001000 discloses a method for the enrichment of EPA and DHA.
  • the enrichment of ethyl esters of EPA and DHA by short path distillation is known from the prior art, for. Harald Breivik in "Long-Chain Omega-3 Specialty Oils", Volume 21 (2007) in The Oily Press Lipid Libary, pp. 111-140, which also describes other methods of enrichment for EPA and DHA and derivatives of EPA and EPA DHA discloses, for example, urea complexation, processes using supercritical solvents, and enzymatic enrichment processes.
  • the present invention is based on the object of providing a further apparatus and a further method for the distillation of temperature-sensitive substances.
  • the device according to the invention and the inventive method for the distillation of temperature-sensitive substances can be used in general.
  • an enrichment of the temperature-sensitive substances, depending on the present substance mixture, either as a top product or as the bottom product of the distillation can be achieved.
  • the F-factor whose unit is Pa 1/2, is described, for example, in Ullmann 's Encyclopedia of Industrial Chemistry, online version, release 2010, 7th Edition, in the chapter “Distillation, 2nd Equipment” under point 2.2, pages 3 to 6 explained.
  • the fractionation column is a structured mass transfer packing column.
  • Columns with structured mass transfer packaging are explained, for example, in Ullmann's Encyclopedia of Industrial Chemistry, online version, release 2010, 7th Edition, in the section "Distillation, 2nd Equipment” under point 3, pages 12 to 21 ,
  • the thin film evaporator is a wiped film evaporator. In one embodiment of the present invention, the thin film evaporator is a wiped rotary evaporator.
  • Thin-film evaporators are described, for example, in Ulimann's Encyclopedia of Industrial Chemistry, online version, Release 2010, 7th Edition, in the chapter “Heat Exchange” under point 2.2.2.1, pages 22 to 25.
  • the inventive method is carried out so that the F-factor is at most 2 Pa 1 2 , preferably at most 1.5 Pa 1 2 , in particular at most 1.1 Pa 1 2 .
  • the device according to the invention is designed such that it is possible to feed an entraining agent into the thin-film evaporator.
  • Suitable entrainers are, in particular, water, steam, nitrogen or carbon dioxide.
  • the process according to the invention is accordingly carried out in one embodiment of the present invention in such a way that an entrainer, which may in particular be water, steam, nitrogen or carbon dioxide, is fed into the thin-film evaporator.
  • the entraining agent may serve to facilitate the separation by distillation of the components of the substance mixture containing temperature-sensitive substances and thus to contribute to avoiding the thermal decomposition of the temperature-sensitive substances.
  • the present invention has been particularly developed by the example of polyunsaturated fatty acids and their derivatives, in particular the example of the methyl esters or ethyl esters of EPA and DHA.
  • the device according to the invention and the method according to the invention can also be transferred to other temperature-sensitive substances or used for their enrichment or purification.
  • the process according to the invention makes it possible to produce highly enriched EPA and / or DHA products starting from fish oils.
  • the EPA and / or DHA products produced by the process according to the invention can be used in the pharmaceutical sector in the dietary supplement market and as so-called "infant nutrition" for Child nutrition can be used.
  • the inventive method allows in the case of distillation of a mixture containing EPA and DHA, among other fatty acids from fish oils, or in a distillation of methyl esters or ethyl esters of said fatty acid mixtures, the production of highly enriched EPA and DHA products. There is a far-reaching depletion of DHA in the distillate and a far-reaching enrichment of DHA in the residue.
  • the method according to the invention has many advantages. Particular mention should be made of short residence times of the temperature-sensitive substances to be distilled. Further to mention are high yields and a simplified process compared to the known molecular distillation. In addition, a decomposition of the temperature-sensitive substances to be distilled, as might occur in conventional distillation columns for fractional distillation, is largely avoided.
  • the largely decomposition-free distillation of temperature-sensitive substances is particularly possible with the device according to the invention and with the method according to the invention, since relatively short fractionation columns with a relatively large diameter can be used, and because the process can be carried out at low throughput and at low head vacuum.
  • a distillation apparatus according to the invention was used as described below in key words. The following operating parameters were used:
  • Bottom Evaporator Thin-film evaporator made of glass with a diameter of 55 mm and a length of the evaporation surface of 430 mm (about 0.074 m 2 )
  • Heating with thermal oil between 175 and 200 ° C (preferably 190-195 ° C)
  • the mixture of substances prior to the distillation consisted of about 90-95% of fatty acid ethyl esters of chain lengths C 14 to C24 having a different number of double bonds and from 5 to 10% of mono-, di- and triglycerides of the same fatty acids.
  • EPA ethyl and DHA ethyl esters were included in the mixture.
  • the lower-boiling compounds enriched in the distillation in the distillate, the higher-boiling compounds remained in the distillation bottoms.
  • the division into the two shares was controlled in particular by the amount of heat introduced. Particularly easy to influence was the division of the EP A ethyl ester on distillate and residue.
  • cut means distillation cut
  • the cut indicates the proportion of distillate to residue
  • eg means in the first line of the following table "Distillate cut 46%” and “residue cut 54%” that the proportion of distillate is 46% and the proportion of residue 54% of the starting material.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention relates to a device for distilling substance mixtures that contain temperature-sensitive substances. The device comprises a thin layer evaporator and a fractionation column, and the fractionation column is placed on the distillate outlet of the thin layer evaporator. The fractionation column has at least three theoretical trays, and the loss of pressure of the fractionation column is maximally 3 hPa (3 mbar) during operation at an F-factor of 1 Pa1/2. The invention further relates to a method for distilling substance mixtures that contain temperature-sensitive substances, characterized in that the method is carried out in the device according to the invention.

Description

Vorrichtung und Verfahren zur Destillation temperaturempfindlicher Stoffe  Apparatus and process for the distillation of temperature-sensitive substances
Die vorliegende Erfindung betrifft eine Vorrichtung zur Destillation von Stoffgemischen, die temperaturempfindliche Stoffe enthalten, wobei die Vorrichtung einen Dünnschichtverdampfer und eine Fraktionierkolonne umfasst, und wobei die Fraktionierkolonne auf den Destillatausgang des Dünnschichtverdarnpfers aufgesetzt ist, und wobei die Fraktionierkolonne mindestens 3 theoretische Böden hat, und wobei der Druckverlust der Fraktionierkolonne im Betrieb bei einem F-Faktor von 1 Pa1/2 maximal 3 hPa (3 mbar) beträgt. Weiterhin betrifft die vorliegende Erfindung ein Verfahren zur Destillation von Stoffgemischen, die temperaturempfindliche Stoffe enthalten, dadurch gekennzeichnet, dass das Verfahren in der erfindungsgemäßen Vorrichtung durchgeführt wird. The present invention relates to a device for the distillation of mixtures containing temperature-sensitive substances, the device comprising a thin-film evaporator and a fractionating column, and wherein the Fraktionierkolonne is placed on the distillate output of Dünnschichtverdarnpfers, and wherein the Fraktionierkolonne has at least 3 theoretical plates, and wherein the pressure loss of the fractionation column in operation at a F-factor of 1 Pa 1/2 is a maximum of 3 hPa (3 mbar). Furthermore, the present invention relates to a method for the distillation of mixtures containing temperature-sensitive substances, characterized in that the method is carried out in the device according to the invention.
Vorrichtungen und Verfahren zur Destillation temperaturempfindlicher Stoffe sind bekannt. Die Kurzwegdestillation, auch Molekulardestillation genannt, ist ein Beispiel für ein solches Verfahren. Als Vorrichtungen für die Destillation temperaturempfindlicher Stoffe kommen zum Beispiel Dünnschichtverdampfer in Betracht. Zu beidem finden sich Nachweise in dem online- Chemielexikon Römpp Online, Version 3.7 unter den Stichworten „Destillation" und „Dünnschichtverdampfer". Devices and methods for the distillation of temperature-sensitive substances are known. Short path distillation, also called molecular distillation, is an example of such a process. Suitable devices for the distillation of temperature-sensitive substances are, for example, thin-film evaporators. For both, there is evidence in the online chemistry dictionary Römpp Online, version 3.7 under the keywords "distillation" and "thin-film evaporator".
Unter den temperaturempfindlichen Stoffen sind insbesondere die mehrfach ungesättigten Fettsäuren und deren Derivate, zum Beispiel deren Methylester oder Ethylester, von Interesse. Of the temperature-sensitive substances, in particular the polyunsaturated fatty acids and their derivatives, for example their methyl esters or ethyl esters, are of interest.
Mehrfach ungesättigte Fettsäuren sind Fettsäuren, die mindestens zwei Doppelbindungen enthalten. Dazu gehören zum Beispiel Linolsäure, alpha-Linolensäure, gamma-Linolensäure und Arachidonsäure. Mehrfach ungesättigte Fettsäuren haben mindestens fünf C-Atome. Im Folgenden werden unter mehrfach ungesättigten Fettsäuren insbesondere solche verstanden, die mindestens sechs C-Atome haben. Auch Omega-3 -Fettsäuren gehören zu den mehrfach ungesättigten Fettsäuren. EPA und DHA sind spezielle Omega-3 -Fettsäuren. Polyunsaturated fatty acids are fatty acids containing at least two double bonds. These include, for example, linoleic acid, alpha-linolenic acid, gamma-linolenic acid and arachidonic acid. Polyunsaturated fatty acids have at least five carbon atoms. In the following, polyunsaturated fatty acids are understood in particular to mean those which have at least six C atoms. Omega-3 fatty acids are also among the polyunsaturated fatty acids. EPA and DHA are special omega-3 fatty acids.
EPA ist die Abkürzung für (5Z,8Z, 1 1 Z, 14Z, 17Z)-Eicosa-5,8, 11 , 14, 17-pentaensäure. DHA ist die Abkürzung für (4Z,7Z, 10Z, 13Z, 16Z, 19Z)-Docosa-4,7, 10,13,16,19-hexaensäure. EPA is the abbreviation for (5Z, 8Z, 11Z, 14Z, 17Z) -eicosa-5,8,11,14,17-pentaenoic acid. DHA is the abbreviation for (4Z, 7Z, 10Z, 13Z, 16Z, 19Z) docosa-4,7, 10,13,16,19-hexaenoic acid.
Mehrfach ungesättigte Fettsäuren, insbesondere EPA und DHA, können als Bestandteil von Nahrungsmitteln, in Nahrungsergänzüngsmitteln (Englisch: dietary Supplements) oder in so genanntem Functional Food eingesetzt werden. Sie können auch im Pharmabereich eingesetzt werden, im Falle von EPA und DHA zum Beispiel zur Therapie oder Prophylaxe koronarer Herzerkrankungen. Sie werden meist als Glycerinester, also als Bestandteil von Fetten eingesetzt. Sie können aber auch als freie Fettsäuren oder in Form von Estern, z. B. Ethylestern, eingesetzt werden. Polyunsaturated fatty acids, especially EPA and DHA, may be included as part of Food, dietary supplements or so-called functional foods. They can also be used in the pharmaceutical sector, for example in the case of EPA and DHA for the therapy or prophylaxis of coronary heart disease. They are usually used as glycerol esters, ie as part of fats. But you can also as free fatty acids or in the form of esters, eg. As ethyl esters, are used.
Mehrfach ungesättigte Fettsäuren, insbesondere EPA und DHA können aus natürlichen Quellen, z. B. aus Fischöl, gewonnen werden. Um mehrfach ungesättigte Fettsäuren, insbesondere EPA und DHA in hoher Konzentration zur Verfügung zu stellen, sind Verfahren zur Anreicherung von mehrfach ungesättigten Fettsäuren, insbesondere von EPA und/oder von DHA erforderlich, mittels derer mehrfach ungesättigte Fettsäuren, insbesondere EPA und/oder DHA, aus natürlichen Quellen wie z. B. Fischöl angereichert werden können. Polyunsaturated fatty acids, especially EPA and DHA may be derived from natural sources, e.g. B. from fish oil, are obtained. In order to provide polyunsaturated fatty acids, in particular EPA and DHA in a high concentration, processes for the enrichment of polyunsaturated fatty acids, in particular of EPA and / or of DHA, are required, by means of which polyunsaturated fatty acids, in particular EPA and / or DHA natural sources such. B. fish oil can be enriched.
Die Anreicherung von mehrfach ungesättigten Fettsäuren durch Kristallisationsverfahren ist aus dem Stand der Technik bekannt. The accumulation of polyunsaturated fatty acids by crystallization processes is known from the prior art.
Acta Chemica Scandinavia 17 (1963) No. 10, Seiten 2622 bis 2627:„Fractionation of Linseed Oil Fatty Acids by Crystallisation" offenbart eine Kristallisation in zwei Stufen, wobei die erste bei - 25°C und die zweite bei - 40°C erfolgt. Als Medium wird Methanol verwendet. Durch diesen Prozess kann eine Anreicherung an C 18:2 erzielt werden. Acta Chemica Scandinavia 17 (1963) no. 10, pages 2622 to 2627: "Fractionation of Linseed Oil Fatty Acids by Crystallization" discloses a crystallization in two stages, the first at -25 ° C and the second at -40 ° C. Methanol is used as the medium Process, an enrichment of C 18: 2 can be achieved.
DE 969 103 offenbart die Anreicherung von EPA und von DHA ausgehend von festen Natriumseifen durch Verwendung von organischen Lösungsmitteln, in denen die Natriumseifen nicht löslich sind, jedoch die anderen Begleitsubstanzen. DE 969103 discloses the accumulation of EPA and DHA from solid sodium soaps by using organic solvents in which the sodium soaps are not soluble but the other adjunct substances.
GB 719 513 offenbart ein Verfahren, bei dem durch Verseifen von Fetten und Ölen Seifen erhalten werden, die wiederum in feste Substanzen umgewandelt werden. Dann werden mit wassermischbaren organischen Lösungsmitteln die ungesättigten Seifen gelöst. GB 719 513 discloses a process in which soaping of fats and oils gives soaps which in turn are converted into solid substances. Then the unsaturated soaps are dissolved with water-miscible organic solvents.
Auch die europäische Patentanmeldung mit der Anmeldungsnummer 10001000 (internes Aktenzeichen der Cognis IP Management GmbH: C 3494) offenbart ein Verfahren zur Anreicherung von EPA und DHA. Auch die Anreicherung von Ethylestern von EPA und DHA mittels Kurzwegdestillation ist aus dem Stand der Technik bekannt, z. B. aus Harald Breivik in„Long-Chain Omega-3 Speciality Oils", Volume 21 (2007) in The Oily Press Lipid Libary, Seiten 111-140. Hier werden auch weitere Anreicherungsverfahren für EPA und DHA bzw. für Derivate von EPA und DHA offenbart, z. B. die Harnstoffkomplexierung, Verfahren unter Nutzung von überkritischen Lösungsmitteln und enzymatische Anreicherungsverfahren. Also, the European patent application with the application number 10001000 (internal file number of Cognis IP Management GmbH: C 3494) discloses a method for the enrichment of EPA and DHA. The enrichment of ethyl esters of EPA and DHA by short path distillation is known from the prior art, for. Harald Breivik in "Long-Chain Omega-3 Specialty Oils", Volume 21 (2007) in The Oily Press Lipid Libary, pp. 111-140, which also describes other methods of enrichment for EPA and DHA and derivatives of EPA and EPA DHA discloses, for example, urea complexation, processes using supercritical solvents, and enzymatic enrichment processes.
Der vorliegenden Erfindung liegt die Aufgabe zu Grunde, eine weitere Vorrichtung und ein weiteres Verfahren zur Destillation temperaturempfindlicher Stoffe bereit zu stellen. The present invention is based on the object of providing a further apparatus and a further method for the distillation of temperature-sensitive substances.
Diese Aufgabe wird gelöst durch die Vorrichtung und durch das Verfahren gemäß den unabhängigen Patentansprüchen. Dabei kann die erfindungsgemäße Vorrichtung und das erfindungsgemäße Verfahren zur Destillation temperaturempfindlicher Stoffe allgemein verwendet werden. Durch die Destillation kann eine Anreicherung der temperaturempfindlichen Stoffe, je nach vorliegendem Stoffgemisch, entweder als Kopfprodukt oder als Sumpfprodukt der Destillation erreicht werden. Natürlich kann auch von einer Reinigung oder Abtrennung statt von einer Destillation oder Anreicherung der temperaturempfindlichen Stoffe gesprochen werden. This object is achieved by the device and by the method according to the independent claims. In this case, the device according to the invention and the inventive method for the distillation of temperature-sensitive substances can be used in general. By the distillation, an enrichment of the temperature-sensitive substances, depending on the present substance mixture, either as a top product or as the bottom product of the distillation can be achieved. Of course, it is also possible to speak of a purification or separation instead of a distillation or enrichment of the temperature-sensitive substances.
Der F-Faktor, dessen Einheit Pa1/2 ist, wird zum Beispiel in Ullmann's Encyclopedia of Industrial Chemistry, online- Version, Release 2010, 7th Edition, im Kapitel„Distillation, 2. Equipment" unter Punkt 2.2, Seiten 3 bis 6 erläutert. The F-factor, whose unit is Pa 1/2, is described, for example, in Ullmann 's Encyclopedia of Industrial Chemistry, online version, release 2010, 7th Edition, in the chapter "Distillation, 2nd Equipment" under point 2.2, pages 3 to 6 explained.
Die Unteransprüche haben besondere Ausführungsformen der vorliegenden Erfindung zum Gegenstand. The subclaims relate to particular embodiments of the present invention.
In einer Ausführungsform der vorliegenden Erfindung ist die Fraktionierkolonne eine Kolonne mit strukturierter Stoffaustauschpackung. Kolonnen mit strukturierter Stoffaustauschpackung (Englisch: „structured packings") werden zum Beispiel in Ullmann's Encyclopedia of Industrial Chemistry, online- Version, Release 2010, 7th Edition, im Kapitel„Distillation, 2. Equipment" unter Punkt 3, Seiten 12 bis 21 erläutert. In one embodiment of the present invention, the fractionation column is a structured mass transfer packing column. Columns with structured mass transfer packaging are explained, for example, in Ullmann's Encyclopedia of Industrial Chemistry, online version, release 2010, 7th Edition, in the section "Distillation, 2nd Equipment" under point 3, pages 12 to 21 ,
In einer Ausführungsform der vorliegenden Erfindung ist der Dünnschichtverdampfer ein gewischter Dünnschichtverdampfer (Englisch: wiped film evaporator). In einer Ausführungsform der vorliegenden Erfindung ist der Dünnschichtverdampfer ein gewischter Rotationsdünnschichtverdampfer. In one embodiment of the present invention, the thin film evaporator is a wiped film evaporator. In one embodiment of the present invention, the thin film evaporator is a wiped rotary evaporator.
Dünnschichtverdampfer werden zum Beispiel in Ulimann 's Encyclopedia of Industrial Chemistry, online-Version, Release 2010, 7th Edition, im Kapitel„Heat Exchange" unter Punkt 2.2.2.1, Seiten 22 bis 25 erläutert. Thin-film evaporators are described, for example, in Ulimann's Encyclopedia of Industrial Chemistry, online version, Release 2010, 7th Edition, in the chapter "Heat Exchange" under point 2.2.2.1, pages 22 to 25.
In einer Ausfuhrungsform der vorliegenden Erfindung wird das erfindungsgemäße Verfahren so durchgeführt, dass der F-Faktor höchstens 2 Pa1 2 , bevorzugt höchstens 1,5 Pa1 2, insbesondere höchstens 1,1 Pa1 2, ist. In one embodiment of the present invention, the inventive method is carried out so that the F-factor is at most 2 Pa 1 2 , preferably at most 1.5 Pa 1 2 , in particular at most 1.1 Pa 1 2 .
In einer Ausführungsform der vorliegenden Erfindung ist die erfindungsgemäße Vorrichtung so ausgeführt, dass es möglich ist, in den Dünnschichtverdampfer ein Schleppmittel einzuspeisen. Als Schleppmittel kommen insbesondere Wasser, Wasserdampf, Stickstoff oder Kohlendioxid in Frage. Das erfindungsgemäße Verfahren wird entsprechend in einer Ausführungsform der vorliegenden Erfindung so ausgeführt, dass in den Dünnschichtverdampfer ein Schleppmittel eingespeist wird, das insbesondere Wasser, Wasserdampf, Stickstoff oder Kohlendioxid sein kann. Das Schleppmittel kann insbesondere dazu dienen, die destillative Trennung der Komponenten des Stoffgemisches, das temperaturempfindliche Stoffe enthält, zu erleichtern und also dazu beizutragen, die thermische Zersetzung der temperaturempfindlichen Stoffe zu vermeiden. In one embodiment of the present invention, the device according to the invention is designed such that it is possible to feed an entraining agent into the thin-film evaporator. Suitable entrainers are, in particular, water, steam, nitrogen or carbon dioxide. The process according to the invention is accordingly carried out in one embodiment of the present invention in such a way that an entrainer, which may in particular be water, steam, nitrogen or carbon dioxide, is fed into the thin-film evaporator. In particular, the entraining agent may serve to facilitate the separation by distillation of the components of the substance mixture containing temperature-sensitive substances and thus to contribute to avoiding the thermal decomposition of the temperature-sensitive substances.
Die vorliegende Erfindung wurde insbesondere an dem Beispiel von mehrfach ungesättigten Fettsäuren und deren Derivaten, insbesondere an dem Beispiel der Methylester oder der Ethylester von EPA und von DHA entwickelt. Die erfindungsgemäße Vorrichtung und das erfindungsgemäße Verfahren können aber auch auf andere temperaturempfindliche Stoffe übertragen bzw. für deren Anreicherung oder Reinigung angewandt werden. The present invention has been particularly developed by the example of polyunsaturated fatty acids and their derivatives, in particular the example of the methyl esters or ethyl esters of EPA and DHA. However, the device according to the invention and the method according to the invention can also be transferred to other temperature-sensitive substances or used for their enrichment or purification.
Das erfindungsgemäße Verfahren ermöglicht insbesondere die Herstellung von hoch angereicherten EPA- und/oder DHA-Produkten ausgehend von Fischölen. In particular, the process according to the invention makes it possible to produce highly enriched EPA and / or DHA products starting from fish oils.
Die nach dem erfindungsgemäße Verfahren hergestellten EPA- und/oder DHA-Produkte können im Pharmabereich im Nahrungsergänzungsmittelmarkt und als so genannte„Infant Nutrition" zur Kinderernährung verwendet werden. The EPA and / or DHA products produced by the process according to the invention can be used in the pharmaceutical sector in the dietary supplement market and as so-called "infant nutrition" for Child nutrition can be used.
Das erfindungsgemäße Verfahren erlaubt im Falle der Destillation eines Gemisches, welches EPA und DHA neben anderen Fettsäuren aus Fischölen enthält, oder bei einer Destillation von Methylestern oder von Ethylestem der genannten Fettsäuregemische die Herstellung von hoch angereicherten EPA- und DHA-Produkten. Dabei erfolgt eine weit reichende Abreicherung von DHA im Destillat und eine weit reichende Anreicherung von DHA im Rückstand. The inventive method allows in the case of distillation of a mixture containing EPA and DHA, among other fatty acids from fish oils, or in a distillation of methyl esters or ethyl esters of said fatty acid mixtures, the production of highly enriched EPA and DHA products. There is a far-reaching depletion of DHA in the distillate and a far-reaching enrichment of DHA in the residue.
Das erfindungsgemäße Verfahren hat viele Vorteile. Insbesondere zu nennen sind kurze Verweilzeiten der zu destillierenden temperaturempfindlichen Stoffe. Weiterhin zu nennen sind hohe Ausbeuten und ein vereinfachter Prozess verglichen mit der bekannten Molekulardestillation. Außerdem wird eine Zersetzung der zu destillierenden temperaturempfindliche Stoffe, wie sie in klassischen Destillationskolonnen zur fraktionierten Destillation vorkommen könnte, weitestgehend vermieden. The method according to the invention has many advantages. Particular mention should be made of short residence times of the temperature-sensitive substances to be distilled. Further to mention are high yields and a simplified process compared to the known molecular distillation. In addition, a decomposition of the temperature-sensitive substances to be distilled, as might occur in conventional distillation columns for fractional distillation, is largely avoided.
Die weitestgehend zersetzungsfreie Destillation temperaturempfindlichen Stoffe ist mit der erfindungsgemäßen Vorrichtung und mit dem erfindungsgemäßen Verfahren insbesondere deshalb möglich, weil hier relativ kurze Fraktionierkolonnen mit einem relativ großen Durchmesser zum Einsatz kommen können, und weil das Verfahren bei geringem Durchsatz und bei niedrigem Kopfvakuum durchgeführt werden kann. The largely decomposition-free distillation of temperature-sensitive substances is particularly possible with the device according to the invention and with the method according to the invention, since relatively short fractionation columns with a relatively large diameter can be used, and because the process can be carried out at low throughput and at low head vacuum.
Beispiele: Examples:
Destillation von Fettsäureethylestern Distillation of fatty acid ethyl esters
% bedeuten im folgenden GC -Flächenprozent der Fettsäureethylester (GC = Gaschromatographie). % in the following mean GC area percent of the fatty acid ethyl esters (GC = gas chromatography).
Es wurde eine erfindungsgemäße Destillationsapparatur verwendet wie sie im Folgenden in Stichworten beschrieben ist. Dabei wurden die im folgenden angegebenen Betriebsparameter verwendet: A distillation apparatus according to the invention was used as described below in key words. The following operating parameters were used:
• Vakuumanlage: Drehschieberpumpe Kopfdruck ca. 0,6-0,7 mbar (lmbar = 1 hPa) • Vacuum system: rotary vane pump head pressure approx. 0.6-0.7 mbar (lmbar = 1 hPa)
• Verspiegelte Fraktionierkolonne aus Glas (Dewar) mit einem Packungsdurchmesser von 75 mm, Packungslänge 510 mm, Packungstyp Sulzer BX • Reflected glass fractionating column (Dewar) with a packing diameter of 75 mm, packing length 510 mm, packing type Sulzer BX
• Kolonnenkopf mit Totalkondensator und getaktetem Rücklaufteiler  • Column head with total condenser and clocked reflux divider
(Rücklaufverhältnis 1 :1)  (Reflux ratio 1: 1)
• Sumpfverdampfer: Dünnschichtverdampfer aus Glas mit einem Durchmesser von 55 mm und einer Länge der Verdampfungsfläche von 430 mm (ca. 0,074 m2) Bottom Evaporator: Thin-film evaporator made of glass with a diameter of 55 mm and a length of the evaporation surface of 430 mm (about 0.074 m 2 )
• Beheizung mit Wärmeträgeröl: zwischen 175 und 200°C (bevorzugt 190-195°C) • Heating with thermal oil: between 175 and 200 ° C (preferably 190-195 ° C)
• Substanzzufuhr (sog.„Feed") aus Tropftrichter ca. 300 ml/h • Substance supply (so-called "feed") from the dropping funnel approx. 300 ml / h
• Das Anfahrprodukt aus dem Sumpf wurde getrennt gehalten, bis Kopfprodukt anfiel • The start-up product from the sump was kept separate until top product was obtained
• Das Abfahrprodukt = Packungsinhalt wurde mit dem Sumpfprodukt kombiniert • The shutdown product = package contents was combined with the bottoms product
Das Stoffgemisch vor der Destillation bestand zu ca. 90 - 95 % aus Fettsäurethylestern der Kettenlängen C 14 bis C24 mit einer unterschiedlichen Anzahl an Doppelbindungen und zu 5 - 10 % aus Mono-, Di- und Triglyceriden derselben Fettsäuren. Insbesondere waren EPA-Ethyler und DHA-Ethylester in dem Gemisch enthalten. Die leichter siedenden Verbindungen reicherten sich bei der Destillation im Destillat an, die höher siedenden Verbindungen verblieben im Destillationssumpf. Die Aufteilung in die beiden Anteile wurde insbesondere durch die eingebrachte Wärmemenge gesteuert. Besonders gut beeinflussbar war die Aufteilung der EP A- Ethylester auf Destillat und Rückstand. The mixture of substances prior to the distillation consisted of about 90-95% of fatty acid ethyl esters of chain lengths C 14 to C24 having a different number of double bonds and from 5 to 10% of mono-, di- and triglycerides of the same fatty acids. In particular, EPA ethyl and DHA ethyl esters were included in the mixture. The lower-boiling compounds enriched in the distillation in the distillate, the higher-boiling compounds remained in the distillation bottoms. The division into the two shares was controlled in particular by the amount of heat introduced. Particularly easy to influence was the division of the EP A ethyl ester on distillate and residue.
Folgende Ergebnisse wurden erhalten. Dabei bedeutet„Cut" Destillationsschnitt, Der Cut gibt den Anteil an Destillat zu Rückstand an. Z. B. bedeutet in der ersten Zeile der folgenden Tabelle „Destillat Cut 46%" und„Rückstand Cut 54%", dass der Anteil Destillat 46% und der Anteil Rückstand 54% des Ausgangsproduktes beträgt. The following results were obtained. In this case, "cut" means distillation cut, the cut indicates the proportion of distillate to residue, eg means in the first line of the following table "Distillate cut 46%" and "residue cut 54%" that the proportion of distillate is 46% and the proportion of residue 54% of the starting material.
Versuch "Feed" Destillat Rückstand Try "Feed" distillate residue
EPA DHA Cut EPA DHA Cut EPA DHA EPA DHA Cut EPA DHA Cut EPA DHA
EE3322_ 1 35,9% 25,9% 46% 52,7% 0,0% 54% 17,0% 50,2%EE3322_ 1 35.9% 25.9% 46% 52.7% 0.0% 54% 17.0% 50.2%
EE3322_ 2 34,4% 23,7% 51% 42,8% 0,0% 49% 27,5% 39,5%EE3322_ 2 34.4% 23.7% 51% 42.8% 0.0% 49% 27.5% 39.5%
EE3426_ 1 36,6% 25,7% 46% 53,7% 0,0% 54% 18,5% 46,8%EE3426_ 1 36.6% 25.7% 46% 53.7% 0.0% 54% 18.5% 46.8%
EE1050_ _1 17,4% 53,6% 19% 8,1% 0,0% 81% 11,6% 64,8%EE1050_ _1 17.4% 53.6% 19% 8.1% 0.0% 81% 11.6% 64.8%
EE1050_ 2 16,6% 51 ,9% 28% 43,0% 0,1% 72% 1 1,4% 62,9%EE1050_ 2 16.6% 51, 9% 28% 43.0% 0.1% 72% 1 1.4% 62.9%
EE1020_ \ 12,9% 20,8% 67% 1,2% 0,0% 33% 12,0% 63,2%EE1020_ \ 12.9% 20.8% 67% 1.2% 0.0% 33% 12.0% 63.2%
EE1020_ 2 13,0% 21 ,2% 65% 3,9% 0,2% 35% 16,3% 58,7% EE1020_ 2 13.0% 21, 2% 65% 3.9% 0.2% 35% 16.3% 58.7%
Diese Ergebnisse zeigen, dass man im Destillat eine EPA-Anreicherung erzielen konnte, ohne gleichzeitig DHA mit überzudestillieren. Damit bietet sich also die Möglichkeit EPA-reiche Destillate herzustellen. Es lassen sich aber auch DHA-reiche Konzentrate mit hoher Ausbeute realisieren. Es konnte keine thermische Zersetzung der Produkte festgestellt werden. These results show that in the distillate an EPA enrichment could be achieved without simultaneously distilling over DHA. This offers the possibility to produce EPA-rich distillates. But it can also realize DHA-rich concentrates with high yield. No thermal decomposition of the products could be detected.

Claims

Eine Vorrichtung zur Destillation von Stoffgemischen, die temperaturempfindliche Stoffe enthalten, wobei die Vorrichtung einen Dünnschichtverdampfer und eine Fraktionierkolonne umfasst, und wobei die Fraktionierkolonne auf den Destillatausgang des Dünnschichtverdampfers aufgesetzt ist, und wobei die Fraktionierkolonne mindestens 3, bevorzugt mindestens 5, theoretische Böden hat, und wobei der Druckverlust der Fraktionierkolonne im Betrieb bei einem F-Faktor von 1 Pa maximal 3 hPa (3 mbar), bevorzugt maximal 2 hPa, insbesondere maximal 1 hPa, beträgt. An apparatus for the distillation of mixtures containing temperature-sensitive substances, the apparatus comprising a thin-film evaporator and a fractionating column, and wherein the fractionating column is placed on the distillate output of the thin-film evaporator, and wherein the fractionation has at least 3, preferably at least 5, theoretical plates, and wherein the pressure loss of the fractionation in operation at an F-factor of 1 Pa maximum 3 hPa (3 mbar), preferably at most 2 hPa, in particular at most 1 hPa.
Die Vorrichtung nach Anspruch 1, wobei die Fraktionierkolonne eine Kolonne mit strukturierter Stoffaustauschpackung ist. The apparatus of claim 1, wherein the fractionating column is a structured mass transfer packing column.
Die Vorrichtung nach Anspruch 1 oder 2, wobei der Dünnschichtverdampfer ein gewischter Dünnschichtverdampfer oder ein Rotationsdünnschichtverdampfer ist. The device of claim 1 or 2, wherein the thin film evaporator is a wiped thin film evaporator or a rotary thin film evaporator.
Die Vorrichtung nach einem der vorherigen Ansprüche, wobei die Vorrichtung es ermöglicht, das zu trennende Stoffgemisch in den Dünnschichtverdampfer einzuspeisen. The device according to one of the preceding claims, wherein the device makes it possible to feed the substance mixture to be separated into the thin-film evaporator.
Die Vorrichtung nach einem der vorherigen Ansprüche, wobei die Vorrichtung es ermöglicht, das zu trennende Stoffgemisch in die Fraktionierkolonne einzuspeisen, wobei die Einspeisung bevorzugt in die Kolonnenmitte möglich ist. The device according to one of the preceding claims, wherein the device makes it possible to feed the substance mixture to be separated into the fractionation column, wherein the feed is preferably possible in the middle of the column.
Die Vorrichtung nach einem der vorherigen Ansprüche, wobei die Vorrichtung weiterhin eine Pumpe zur Erzeugung eines Vakuums in der Vorrichtung umfasst, wobei die Pumpe bevorzugt so gestaltet ist, dass ein Vakuum von 3 hPa oder einem geringeren Druck, bevorzugt 2 hPa oder einem geringeren Druck, insbesondere 1 hPa oder einem geringeren Druck, erreicht werden kann. The apparatus of any of the preceding claims, wherein the apparatus further comprises a pump for generating a vacuum in the apparatus, the pump being preferably configured to provide a vacuum of 3 hPa or lower pressure, preferably 2 hPa or lower pressure, in particular 1 hPa or a lower pressure can be achieved.
Ein Verfahren zur Destillation von Stoffgemischen, die temperaturempfindliche Stoffe enthalten, dadurch gekennzeichnet, dass das Verfahren in einer Vorrichtung gemäß einem der Ansprüche 1 bis 6 durchgeführt wird A process for the distillation of mixtures containing temperature-sensitive substances, characterized in that the process is carried out in a device according to one of claims 1 to 6
8. Das Verfahren nach Anspruch 7, wobei das Stoffgemisch mehrfach ungesättigte Fettsäuren oder deren Methylester oder deren Ethylester enthält. 8. The method of claim 7, wherein the mixture contains polyunsaturated fatty acids or their methyl esters or their ethyl esters.
9. Das Verfahren nach Anspruch 8, wobei das Stoffgemisch omega-3 -Fettsäuren oder deren Methylester oder deren Ethylester enthält 9. The method of claim 8, wherein the mixture contains omega-3 fatty acids or their methyl esters or their ethyl esters
10. Das Verfahren nach Anspruch 9, wobei das Stoffgemisch EPA und DHA, beide als freie Fettsäure, enthält. The method of claim 9, wherein the composition comprises EPA and DHA, both as free fatty acid.
11. Das Verfahren nach Anspruch 10, wobei das Stoffgemisch durch Isolierung der freien Fettsäuren aus einem Fischöl erhalten wurde. 11. The method of claim 10, wherein the mixture of substances was obtained by isolating the free fatty acids from a fish oil.
12. Das Verfahren nach Anspruch 9, wobei das Stoff gemisch EPA und DHA, beide in Form ihrer Ethylester, enthält. 12. The method of claim 9, wherein the substance mixture contains EPA and DHA, both in the form of their ethyl esters.
13. Das Verfahren nach Anspruch 12, wobei das Stoffgemisch durch Überführung der freien Fettsäuren aus einem Fischöl in ihre Ethylester erhalten wurde. 13. The method of claim 12, wherein the mixture of substances was obtained by converting the free fatty acids from a fish oil into their ethyl esters.
14. Das Verfahren nach einem der Ansprüche 10 bis 13, wobei nach der Destillation ein Produkt erhalten wird, das mindestens 30 Gew.-%, bevorzugt mindestens 40 Gew.-%, EPA und höchstens 10 Gew.-%, bevorzugt höchstens 5 Gew.-%, DHA (jeweils berechnet als Masse an freier Fettsäure bezogen auf die gesamte Masse des Produkts) enthält. 14. The method according to any one of claims 10 to 13, wherein after the distillation, a product is obtained which is at least 30 wt .-%, preferably at least 40 wt .-%, EPA and at most 10 wt .-%, preferably at most 5 wt .-%, DHA (calculated in each case as the mass of free fatty acid based on the total mass of the product).
15. Das Verfahren nach einem der Ansprüche 10 bis 13, wobei nach der Destillation ein Produkt erhalten wird, das mindestens 45 Gew.-%, bevorzugt mindestens 55 Gew.-%, DHA und höchstens 20 Gew.-%, bevorzugt höchstens 10 Gew.-%, EPA (jeweils berechnet als Masse an freier Fettsäure bezogen auf die gesamte Masse des Produkts) enthält. 15. The method according to any one of claims 10 to 13, wherein after the distillation, a product is obtained, the at least 45 wt .-%, preferably at least 55 wt .-%, DHA and at most 20 wt .-%, preferably at most 10 wt .-%, EPA (calculated in each case as the mass of free fatty acid based on the total mass of the product) contains.
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