EP0576191A2 - Abtrennung von ungesättigten Produkten - Google Patents

Abtrennung von ungesättigten Produkten Download PDF

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Publication number
EP0576191A2
EP0576191A2 EP93304637A EP93304637A EP0576191A2 EP 0576191 A2 EP0576191 A2 EP 0576191A2 EP 93304637 A EP93304637 A EP 93304637A EP 93304637 A EP93304637 A EP 93304637A EP 0576191 A2 EP0576191 A2 EP 0576191A2
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EP
European Patent Office
Prior art keywords
medium
polyunsaturates
compounds
entrapment
separation
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Withdrawn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
EP93304637A
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English (en)
French (fr)
Other versions
EP0576191A3 (de
Inventor
John Boden Cloughley
Hubertus Regtop
Ortwin Bode
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.)
Scotia Holdings PLC
Original Assignee
Scotia Holdings PLC
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 Scotia Holdings PLC filed Critical Scotia Holdings PLC
Publication of EP0576191A2 publication Critical patent/EP0576191A2/de
Publication of EP0576191A3 publication Critical patent/EP0576191A3/de
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
    • C11B7/0008—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents
    • C11B7/0058—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents in solvents or mixtures of solvents of different natures or compositions used in succession
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
    • C11B7/0008—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents
    • C11B7/0033—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents in solvents containing other heteroatoms in their molecule
    • 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
    • C11C1/007—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids using organic solvents

Definitions

  • the invention relates to the separation of unsaturated organic compounds from other such compounds or from saturated compounds.
  • the invention in one aspect lies in a process for fractionating a diverse range of unsaturated compounds.
  • unsaturated compounds examples are eicosanoids, tocopherols, tocotrienols etc.
  • doubly, triply or more highly ethylenically unsaturated compounds such as unsaturated fatty acids, fatty alcohols and the like (polyunsaturates) are separated from those with fewer ethylenic unsaturations or completely saturated, using a selective, liquid entrapment medium.
  • the unsaturated fraction is extracted from the entrapment medium by contacting it with an immiscible release medium, and is normally then recovered from the release medium, though in principle the process can be two stage if for example the unsaturate is not the primarily desired product.
  • the entrapment medium and normally also the release medium are recycled.
  • the invention lies in the entrapment medium itself and its method of preparation. It also lies in the separated products obtained by the process, of which the unsaturates will normally be the more valuable product and indeed may be novel products in the sense of not having been prepared before in purified form.
  • the fraction not selected by the entrapment medium is however equally a product of the process.
  • a particular application of the invention is to fractionate mixtures of polyunsaturated fatty acids and related compounds.
  • the process can be applied successfully to the fatty acids themselves and to their derivatives such as salts, alkyl esters, mono-glycerides, di-glycerides, tri-glycerides, phospholipids and amides as well as to other compounds containing fatty acid carbon chains with unconjugated double bonds, such as the fatty acid alcohols.
  • Mixed glycerides can be fractionated, in particular for example in recovery of the valuable triglyceride dilinoleoyl monogamma linolenoyl glycerol (DLMG) from triglyceride mixtures.
  • DLMG dilinoleoyl monogamma linolenoyl glycerol
  • the sulphones particularly sulpholane, have an unusual combination of properties.
  • Sulpholane otherwise tetramethylene sulphone or tetrahydrothiophene-1,1-dioxide, is is the most common but other available sulphones are 3-sulpholene, otherwise 2,5-dihydrothiophene-1, 1-dioxide and acyclic compounds such as dimethyl sulphone diiodomethyl p-tolyl sulphone and di-(4-hydroxyphenyl) sulphone, otherwise Bisphenol S
  • sulpholane itself is known broadly for use in enriching the unsaturation level in fatty oils (Kirk Othmer, section on “Sulpholanes and Sulphones” p. 964, with references to U.S. Patent 2 360 860 (1944) and Wisniak Br. Chem. Eng. 15(1) 76 (1970).) It is the preferred entrapment medium for use in the process of the present invention.
  • the invention for the first time combines the selective solvency of sulphones for unsaturated fatty acids with the known ability of silver salts and other 'type-b' cations to form reversible pi-complexes with the double bonds of unsaturated compounds.
  • This two-component entrapment medium is the basis of a particularly valuable form of the current invention which provides a continuous, efficient, flexible process for the preparation of products of high quality and purity suitable for the nutritional and pharmaceutical industries.
  • Silver salts such as the nitrate dissolve readily in sulpholane in the presence of a proportion of water, for example in commercial grade sulpholane containing 3 wt% dionised water.
  • silver salts of copper, gold or other metals with incomplete electron shells capable of the required pi-complexing is not excluded.
  • Silver nitrate has a low solubility in anhydrous sulfolane, but a solution of 10g silver nitrate in 100 ml sulfolane water 95:5 by volume can for example be obtained, and similarly a solution of 20g silver nitrate in 100 ml sulfolane water 88:12.
  • the entrapment medium is thus particularly suitably made up of sulpholane, water and silver nitrate.
  • Sulpholane is a viscous, high-boiling, non-toxic, dipolar, aprotic solvent which has selectivity for fatty acids and fatty acid esters depending upon the molecular weight and degree of unsaturation.
  • Silver has been used in the chromatographic separation of unsaturated compounds. However no free solvent system which dissolves silver salts whilst having low solubility for saturated compounds has hitherto been found, and the technical and commercial demands associated with recovery, re-use and re-circulation of silver have remained unsatisfied.
  • the successful application and degree of selectivity of the process depends upon the partition coefficients of the target substance between the feed mixture and the entrapment medium and between the entrapment medium and the release medium.
  • Favourable partition ratios for different target extractives can be obtained by adjusting the entrapment medium, for example as to the amount of water and silver salt used to make up the preferred silver containing sulpholane medium, and by selecting an appropriate release medium with the required solubilising and polarity properties.
  • the silver/sulpholane entrapment medium is very satisfactory in that it allows the separation of fatty acids containing two, three or more double bonds from those that are dienes, monoenes or saturates. Furthermore, a similar level of selectivity is obtained when the fatty acids are present in the much more complex and heterogeneous triglyceride form, of which natural vegetable-seed oils, marine fish oils and fungal biomass oils are composed. For example, in evening primrose oil mixed triglycerides such as DLMG containing one or more triply unsaturated gamma-linolenic acid moeities are selectively concentrated at the expense of triglyceride species containing various permutations of saturated, monoenoic and dienoic acyl groups.
  • the release medium to extract the target polyunsaturated substances from the liquid entrapment medium.
  • the release medium has to be largely immiscible with the entrapment medium and has of course to dissolve the target polyunsaturated fraction; it should also desirably have a low boiling point for ready subsequent separation from the target fraction.
  • Hydrocarbon solvents such as hexane, or petroleum hydrocarbon mixtures, or olefins such as cyclohexene, are suited to many applications of the process and can be selected to give enhanced extraction for a particular extractive by manipulation of partitioning behaviour.
  • Extraction of polyunsaturated fatty acid species with hexane for example is essentially quantitative and the hexane is readily removed and recovered for re-use.
  • the sulpholane/silver medium is also easily freed from excess hexane and is suited to be re-cycled directly.
  • sulpholane has been quoted as the solution component of the entrapment medium because it is commercially available and inexpensive, other sulpholane derivatives can also be used. Mixtures of sulphones with standard organic reagents such as acetone, ethanol and ethyl acetate can also be used successfully as the entrapment medium in the process.
  • the salt component of the entrapment medium need not necessarily be a nitrate.
  • Other soluble salts for example silver tetrafluoroborate and silver trifluoroacetate, can be used.
  • the entrapment medium can also include other cations which form pi-complexes with unsaturated compounds.
  • process of this invention in preferred form may be set out as comprising the following stages:
  • the mixture to be separated is introduced through feed line 1 and admixed vigorously with the entrapment medium, introduced through a separate line 2, in the contact zone 3.
  • the ratio of medium to mixture is between 1:2 and 20:1 and the contact time is between 20 seconds and 100 minutes at temperatures between -80°C and 90°C.
  • Suitable equipment for carrying out this liquid-liquid extraction may comprise an impinging jet mixer, an agitation vessel, a centrifugal extractor, etc. and co-current and counter-current systems can be used.
  • the mixture and the entrapment medium are caused to produce a supernatant raffinate phase and an extract phase which are separately withdrawn respectively through lines 4 and 5.
  • the separation of these two phases may be effected by settling, decantation or centrifugation.
  • the raffinate phase can be fed back to the contacting zone for re-partitioning to separate residual polyunsaturates from non-polyunsaturate species.
  • the extract phase containing the polyunsaturate fraction complexed with the entrapment medium is transferred through line 6 and partitioned against release medium (supplied via line 7) in the contact zone 8.
  • release medium supplied via line 7
  • the same sort of equipment as is indicated above can be used in this second extraction stage and also in the associated phase separation, although the operating conditions may have to be varied.
  • the ratio of releasing medium to entrapment medium/polyunsaturates complex is between 20:1 and 1:5 and contact time is between 20 seconds and 60 minutes at ambient temperature.
  • the extract phase and the raffinate phase are separately withdrawn respectively through lines 9 and 10.
  • the raffinate from this second extraction stage is the entrapment medium and is fed directly back to process with no further treatment required, since the process can tolerate the small amount of release medium required to saturate the entrapment medium.
  • the extract phase containing the low boiling release medium and the product is transferred through line 1 to solvent recovery system where the release medium is removed, condensed and collected.
  • the product can be treated by short path distillation to remove all traces of the release medium. It may be necessary to treat the release medium with brine occasionally to remove silver ions, easily recovered as silver chloride by filtration with subsequent removal of the water by centrifugation.
  • Silver nitrate (10g) was dissolved with heating to 70°C in water (5 ml) and sulpholane (95 ml) added with stirring to form a clear solution from which silver nitrate did not crystallise at room temperature.
  • This stock solution is suitable for most separations and may be re-used more than twenty times in the following examples without degeneration or cross contamination. It is referred to as 95 SAg.
  • Silver nitrate (20g) was dissolved in 12 ml of water at 40°C and sulpholane (88 ml) added with stirring. This solution is referred to as 88 SAg, and is very stable. It is capable of being recycled many times with little fall off in selectivity and separation performance.
  • Refined evening primrose oil was taken, containing 8.2% gamma-linolenic acid in terms of its fatty acid composition and 13.8% of its triglyceride in the form of the isomers of DLMG, and 10g was added to 95 SAg (100 ml) and vigorously shaken for a total contact time of 1 minute. It was then allowed to separate into two distinct layers over a period of 5 minutes. The supernatant raffinate phase consisting of saturated and monoeroic fatty acid containing triglycerides was decanted.
  • the bottom phase consisting of triglycerides containing polyunsaturated fatty acids in the entrapment medium was then contacted with 20 ml of the releasing medium hexane and shaken for 2 minutes. The two phases were allowed to settle for 10 minutes. The supernatant extract phase containing the oil was decanted. A second 20 ml of hexane was added to the 95 SAg phase and the mixture shaken for 2 minutes before allowing to settle for phase separation. The supernatant hexane extract was combined with the first extract and transferred to a solvent recovery vessel where the hexane was removed.
  • the evening primrose oil remaining (2.05g) was enriched in the target polyunsaturated fatty acid gamma-linolenic acid by a factor of 2.9 i.e. the product contained 23.8% gamma-linolenic acid and 50% of its triglycerides as DLMG.
  • Unrefined sardine oil was converted into its fatty acid ethyl esters by transesterification with sodium ethoxide in ethanol at 60°C.
  • the crude ethyl esters were purified by thin-film evaporation at 130°C and 0.03mm pressure to yield a colourless mixture of ethyl esters.
  • a sample of this (10g) was contacted with 88 SAg (80ml) and shaken vigorously for 5 minutes and was then allowed to settle for 20 minutes.
  • the raffinate was decanted and contacted a second time with the entrapment medium (40 ml), vigorously shaken for 5 minutes and allowed to settle for 20 minutes.
  • Eicosapentaenoic acid had been concentrated from 14.8% to 33.4% and docosahexaenoic acid from 7.6% to 13.8%.
  • the total of omega-3 polyunsaturated fatty acids had been increased from 24.8% to 52.9%.
  • Palm oil residue i.e. the material removed during the deodorisation stage of the refining operation was treated with acetone at low temperature to remove the major proportion of fatty acids and triglycerides as a crystal fraction by filtration.
  • the filtrate contained largely sterols, tocopherols and tocotrienols and 10g of this was contacted with 95 SAg (120g) and shaken vigorously for 5 minutes. After allowing 15 minutes for the two phases to form, the upper raffinate phase was decanted.
  • the lower phase was contacted with 250ml hexane, shaken for 10 minutes and allowed to settle for 20 minutes before decanting off the upper extract layer.
  • the product (2.2g) contained 60% tocotrienols, compounds containing three double bonds on the phytyl side chain, of which the gamma species was the predominant. Furthermore, the product recovered from the raffinate above contained 50% tocopherols, similar compounds but containing no double bonds on the phytyl side chain.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
EP9393304637A 1992-06-16 1993-06-15 Abtrennung von ungesättigten Produkten. Withdrawn EP0576191A3 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9212788 1992-06-16
GB929212788A GB9212788D0 (en) 1992-06-16 1992-06-16 Separation of unsaturates

Publications (2)

Publication Number Publication Date
EP0576191A2 true EP0576191A2 (de) 1993-12-29
EP0576191A3 EP0576191A3 (de) 1994-11-02

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ID=10717202

Family Applications (1)

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EP9393304637A Withdrawn EP0576191A3 (de) 1992-06-16 1993-06-15 Abtrennung von ungesättigten Produkten.

Country Status (12)

Country Link
EP (1) EP0576191A3 (de)
JP (1) JPH0649480A (de)
KR (1) KR940000408A (de)
AU (1) AU672405B2 (de)
CA (1) CA2098526A1 (de)
FI (1) FI932737A (de)
GB (1) GB9212788D0 (de)
NO (1) NO300550B1 (de)
NZ (1) NZ247884A (de)
RU (1) RU2124045C1 (de)
TW (1) TW240175B (de)
ZA (1) ZA934243B (de)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997046649A1 (en) * 1996-06-03 1997-12-11 Croda International Plc Treatment of oils
WO2000050547A1 (en) * 1999-02-26 2000-08-31 Monsanto Company Process for separating a triglyceride comprising a docosahexaenoic acid residue from a mixture of triglycerides
EP2330177A1 (de) * 2008-09-10 2011-06-08 Q.P. Corporation Verfahren zur erfassung hoch ungesättigter fettsäurederivate
CN107922307A (zh) * 2015-06-01 2018-04-17 备前化成株式会社 高纯度、高收率的高度不饱和脂肪酸的生产方法
CN110709496A (zh) * 2017-06-14 2020-01-17 日清药业股份有限公司 含有高度不饱和脂肪酸的组合物的制造方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2360860A (en) * 1943-02-08 1944-10-24 Shell Dev Solvent extraction process
DE1946373A1 (de) * 1969-09-12 1972-02-03 Monsanto Co Verfahren zur Trennung von Kohlenwasserstoffen
US3763200A (en) * 1971-09-20 1973-10-02 Exxon Research Engineering Co Complexes of monovalent copper and silver salts derived from fluorocarbon substituted sulfonic acids
FR2179164A1 (de) * 1972-04-07 1973-11-16 Mitsubishi Chem Ind
EP0155097A2 (de) * 1984-02-29 1985-09-18 Babcock-Hitachi Kabushiki Kaisha Verfahren zur Herstellung von Methyl-Ethyl-Keton
US4961881A (en) * 1988-02-17 1990-10-09 Uop Process for separating triglycerides and regenerating absorbent used in said separation process
US5062866A (en) * 1988-10-13 1991-11-05 Exxon Research And Engineering Co. Polymeric membrane and process for separation of aliphatically unsaturated hydrocarbons

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4277412A (en) * 1980-01-02 1981-07-07 The Proctor & Gamble Company Fractionation of triglyceride mixtures
US4305882A (en) * 1980-03-21 1981-12-15 The United States Of America As Represented By The Secretary Of Agriculture Partial argentation resin chromatography for separation of polyunsaturated fatty esters
CA2040925C (en) * 1990-04-24 2000-01-25 Yoshihisa Misawa Method of purifying polyunsaturated aliphatic compounds

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2360860A (en) * 1943-02-08 1944-10-24 Shell Dev Solvent extraction process
DE1946373A1 (de) * 1969-09-12 1972-02-03 Monsanto Co Verfahren zur Trennung von Kohlenwasserstoffen
US3763200A (en) * 1971-09-20 1973-10-02 Exxon Research Engineering Co Complexes of monovalent copper and silver salts derived from fluorocarbon substituted sulfonic acids
FR2179164A1 (de) * 1972-04-07 1973-11-16 Mitsubishi Chem Ind
EP0155097A2 (de) * 1984-02-29 1985-09-18 Babcock-Hitachi Kabushiki Kaisha Verfahren zur Herstellung von Methyl-Ethyl-Keton
US4961881A (en) * 1988-02-17 1990-10-09 Uop Process for separating triglycerides and regenerating absorbent used in said separation process
US5062866A (en) * 1988-10-13 1991-11-05 Exxon Research And Engineering Co. Polymeric membrane and process for separation of aliphatically unsaturated hydrocarbons

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997046649A1 (en) * 1996-06-03 1997-12-11 Croda International Plc Treatment of oils
WO2000050547A1 (en) * 1999-02-26 2000-08-31 Monsanto Company Process for separating a triglyceride comprising a docosahexaenoic acid residue from a mixture of triglycerides
US6399803B1 (en) 1999-02-26 2002-06-04 Omegatech, Inc. Process for separating a triglyceride comprising a docosahexaenoic acid residue from a mixture of triglycerides
EP2330177A1 (de) * 2008-09-10 2011-06-08 Q.P. Corporation Verfahren zur erfassung hoch ungesättigter fettsäurederivate
EP2330177A4 (de) * 2008-09-10 2013-10-16 Q P Corp Verfahren zur erfassung hoch ungesättigter fettsäurederivate
US8680305B2 (en) 2008-09-10 2014-03-25 Q.P. Corporation Method for obtaining polyunsaturated fatty acid derivatives
CN107922307A (zh) * 2015-06-01 2018-04-17 备前化成株式会社 高纯度、高收率的高度不饱和脂肪酸的生产方法
US10196584B2 (en) 2015-06-01 2019-02-05 Bizen Chemical Co., Ltd. Production method of highly unsaturated fatty acid with high purity/high yield
EP3305754A4 (de) * 2015-06-01 2019-02-27 Bizen Chemical Co., Ltd. Verfahren zur herstellung einer hoch ungesättigten fettsäure mit hohem reinheitsgrad bei hoher ausbeute
CN107922307B (zh) * 2015-06-01 2021-01-12 备前化成株式会社 高纯度、高收率的高度不饱和脂肪酸的生产方法
CN110709496A (zh) * 2017-06-14 2020-01-17 日清药业股份有限公司 含有高度不饱和脂肪酸的组合物的制造方法
EP3640317A4 (de) * 2017-06-14 2021-03-03 Nisshin Pharma Inc. Verfahren zur herstellung einer zusammensetzung mit hochgradig ungesättigten fettsäuren

Also Published As

Publication number Publication date
FI932737A (fi) 1993-12-17
JPH0649480A (ja) 1994-02-22
NO932205L (no) 1993-12-17
NO932205D0 (no) 1993-06-15
RU2124045C1 (ru) 1998-12-27
AU672405B2 (en) 1996-10-03
ZA934243B (en) 1994-01-12
TW240175B (de) 1995-02-11
NO300550B1 (no) 1997-06-16
AU4130793A (en) 1993-12-23
FI932737A0 (fi) 1993-06-15
NZ247884A (en) 1995-10-26
GB9212788D0 (en) 1992-07-29
CA2098526A1 (en) 1993-12-17
EP0576191A3 (de) 1994-11-02
KR940000408A (ko) 1994-01-03

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