EP2627423A1 - Dispositif et procédé de distillation de substances sensibles à la température - Google Patents

Dispositif et procédé de distillation de substances sensibles à la température

Info

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
Authority
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.)
Withdrawn
Application number
EP11763590.4A
Other languages
German (de)
English (en)
Inventor
Peter Horlacher
Dieter Hietsch
Jörg SCHWARZER
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cognis IP Management GmbH
Original Assignee
Cognis IP Management GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Cognis IP Management GmbH filed Critical Cognis IP Management GmbH
Priority to EP11763590.4A priority Critical patent/EP2627423A1/fr
Publication of EP2627423A1 publication Critical patent/EP2627423A1/fr
Withdrawn legal-status Critical Current

Links

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.

Landscapes

  • 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

L'invention concerne un dispositif de distillation de mélanges contenant des substances sensibles à la température. Ledit dispositif comprend un évaporateur à couche mince et une colonne de fractionnement. La colonne de fractionnement est posée sur la sortie de distillat de l'évaporateur à couche mince et elle possède au moins 3 plateaux théoriques, la perte de pression en service de la colonne de fractionnement étant au maximum égale à 3 hPa (3 mbar) à un coefficient F de 1 Pa1/2. En outre, l'invention concerne un procédé de distillation de mélanges contenant des substances sensibles à la température, qui est mis en oeuvre dans le dispositif selon l'invention.
EP11763590.4A 2010-10-13 2011-09-23 Dispositif et procédé de distillation de substances sensibles à la température Withdrawn EP2627423A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP11763590.4A EP2627423A1 (fr) 2010-10-13 2011-09-23 Dispositif et procédé de distillation de substances sensibles à la température

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP10187409 2010-10-13
EP11763590.4A EP2627423A1 (fr) 2010-10-13 2011-09-23 Dispositif et procédé de distillation de substances sensibles à la température
PCT/EP2011/004760 WO2012048792A1 (fr) 2010-10-13 2011-09-23 Dispositif et procédé de distillation de substances sensibles à la température

Publications (1)

Publication Number Publication Date
EP2627423A1 true EP2627423A1 (fr) 2013-08-21

Family

ID=43742385

Family Applications (1)

Application Number Title Priority Date Filing Date
EP11763590.4A Withdrawn EP2627423A1 (fr) 2010-10-13 2011-09-23 Dispositif et procédé de distillation de substances sensibles à la température

Country Status (5)

Country Link
US (1) US20130292242A1 (fr)
EP (1) EP2627423A1 (fr)
AU (1) AU2011316139B2 (fr)
CA (1) CA2814849A1 (fr)
WO (1) WO2012048792A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2661234T3 (es) 2011-03-08 2018-03-28 Cognis Ip Management Gmbh Un procedimiento para la destilación de ésteres de ácidos grasos
KR102117806B1 (ko) 2012-05-14 2020-06-01 닛폰 스이산 가부시키가이샤 환경 오염 물질을 저감시킨 고도 불포화 지방산 또는 고도 불포화 지방산 에틸에스테르 및 그 제조 방법
JP6824038B2 (ja) 2013-12-04 2021-02-03 日本水産株式会社 ジホモ−γ−リノレン酸含有微生物油及びジホモ−γ−リノレン酸含有微生物菌体
CA2995558C (fr) 2015-07-06 2022-07-05 K.D. Pharma Bexbach Gmbh Procede d'obtention d'acides gras libres et/ou d'esters d'acides gras
KR102333313B1 (ko) * 2019-09-27 2021-12-02 씨제이제일제당 (주) 풍미가 강화된 원물 농축액 및 이의 제조 방법
FR3108622B1 (fr) * 2020-03-27 2024-08-23 Polaris Procédé de fractionnement d’acides gras à deux carbones de différence par distillation moléculaire

Citations (7)

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US3644179A (en) * 1967-09-28 1972-02-22 Krems Chemie Gmbh Method and apparatus for continuous fractionation of tall oil and similar mixtures of organic substances with preliminary plural stage thin film evaporation
US4141799A (en) * 1976-08-21 1979-02-27 Bayer Aktiengesellschaft Process for the purification of high-melting organic products
DE4129076A1 (de) * 1991-09-02 1993-03-04 Leuna Werke Ag Verfahren zur reinigung von caprolactam
WO1993019144A1 (fr) * 1992-03-18 1993-09-30 F. Hoffmann-La Roche Ag Esters d'acides gras
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WO2009009271A2 (fr) * 2007-07-06 2009-01-15 Dow Global Technologies Inc. Purification de compositions d'ester gras d'alkyle hydrogéné et hydroformylé

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GB719513A (en) 1951-09-25 1954-12-01 Olav Notevarp Improved process for fractionating highly unsaturated fatty acids from less unsaturated and saturated fatty acids
NL172648B (nl) 1951-09-25 1955-10-15 Shionogi & Co Werkwijze voor het bereiden van een ortho-aminofenylketonderivaat.
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US3644179A (en) * 1967-09-28 1972-02-22 Krems Chemie Gmbh Method and apparatus for continuous fractionation of tall oil and similar mixtures of organic substances with preliminary plural stage thin film evaporation
US4141799A (en) * 1976-08-21 1979-02-27 Bayer Aktiengesellschaft Process for the purification of high-melting organic products
DE4129076A1 (de) * 1991-09-02 1993-03-04 Leuna Werke Ag Verfahren zur reinigung von caprolactam
WO1993019144A1 (fr) * 1992-03-18 1993-09-30 F. Hoffmann-La Roche Ag Esters d'acides gras
US5973173A (en) * 1995-05-26 1999-10-26 Henkel Kommanditgesellschaft Auf Aktien Process for concentrating azelaic acid
DE19605286A1 (de) * 1996-02-13 1997-08-14 Basf Ag Druckverlustarme Gewebepackungen oder gewebeähnliche Packungen mit geordneter Struktur zur Verwendung in Stoffaustauschkolonnen
WO2009009271A2 (fr) * 2007-07-06 2009-01-15 Dow Global Technologies Inc. Purification de compositions d'ester gras d'alkyle hydrogéné et hydroformylé

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Also Published As

Publication number Publication date
US20130292242A1 (en) 2013-11-07
WO2012048792A1 (fr) 2012-04-19
AU2011316139B2 (en) 2016-07-07
CA2814849A1 (fr) 2012-04-19
AU2011316139A1 (en) 2013-05-30

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