EP0224798B1 - Verwendung von Alkylglycosiden zur Trennung von Fettsäureestergemischen - Google Patents

Verwendung von Alkylglycosiden zur Trennung von Fettsäureestergemischen Download PDF

Info

Publication number
EP0224798B1
EP0224798B1 EP86116026A EP86116026A EP0224798B1 EP 0224798 B1 EP0224798 B1 EP 0224798B1 EP 86116026 A EP86116026 A EP 86116026A EP 86116026 A EP86116026 A EP 86116026A EP 0224798 B1 EP0224798 B1 EP 0224798B1
Authority
EP
European Patent Office
Prior art keywords
fatty acid
wetting agent
weight
acid ester
solid
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.)
Expired
Application number
EP86116026A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0224798A1 (de
Inventor
Richard Schuh
Manfred Dr. Biermann
Alfred Dr. Struve
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0224798A1 publication Critical patent/EP0224798A1/de
Application granted granted Critical
Publication of EP0224798B1 publication Critical patent/EP0224798B1/de
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C11B7/0091—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils non-solvents, e.g. water wherein the fat or oil is dispersed account a more washing out of fractions is not taken into
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives

Definitions

  • the invention relates to separations of fatty acid ester mixtures occurring in fats and oils by the known crosslinking process using aqueous wetting agent solutions containing alkylglycosides.
  • Natural fats and oils differ in chain length and degree of saturation of their fatty acid ester components and thus also in their physical properties.
  • the melting points of saturated fatty acid esters are above room temperature, while unsaturated fatty acid esters are liquid at room temperature.
  • the separation of fats into solid and liquid components represents a separation into more saturated and more unsaturated parts.
  • a separation into solid and liquid constituents can advantageously be achieved by the so-called cross-linking process, a separation in the presence of aqueous wetting agent-like solutions, the solid portions being absorbed by the aqueous phase by wetting.
  • JP 57/197 discloses mixtures of fatty alcohol sulfate and sorbitan fatty acid esters as wetting agents for separating fatty acids and fats into solid and liquid constituents.
  • the abstracts of Chemical Abstracts CA 100, 123 162v and CA 96, 144 899e describe the crosslinking of fats using wetting agents containing sucrose fatty acid esters or mixtures of sorbitan or polyoxyethylene sorbitan fatty acid esters and fatty acid salts.
  • sorbitan fatty acid esters can be subject to hydrolysis in alkaline media, in particular at higher temperatures, proves disadvantageous when using sorbitan fatty acid esters.
  • the object of the invention was to provide wetting agent solutions which show equally good separation effects of fats and oils in solid and liquid components as wetting agent solutions of the prior art, but which contain hydrolysis-stable substances which are produced from renewable raw materials.
  • aqueous glyceride-containing aqueous wetting agent solutions are particularly suitable for achieving the object according to the invention, although alkyl glycosides and their wetting agent properties have been known for years.
  • the invention accordingly relates to the use of alkylglycosides with up to 24 carbon atoms in the alkyl chain as wetting agents in aqueous wetting agent solutions for separating fatty acid ester mixtures into solid and liquid constituents by the known crosslinking process.
  • Alkylglycoside-containing wetting agent solutions have the great advantage over wetting agent solutions from the prior art in that they are hydrolysis-stable and that the alkylglycosides contained in them represent a known class of substance which can be prepared from renewable raw materials by conventional methods of organic synthesis.
  • the alkyl glycosides used according to the invention are derived in particular from fatty alcohols and sugars.
  • Alkyl glycosides having a Ce, Ce, C 10 , C 12 , C 14 , C 1 e and / or C 18 alkyl radical which are straight-chain or branched, saturated but also mono- or poly-olefinically unsaturated are preferred and can have up to 3 double bonds, for example, or mixtures of such compounds.
  • Alkyl glycosides whose alkyl or alkenyl radical contains 10 to 16 carbon atoms are particularly suitable.
  • both alkyl monoglycosides in which a cyclic sugar residue is attached to the alcohol are suitable, but also oligomers with preferably up to 8, in particular up to 3, glycosidically attached sugar residues, for example glucose or maftose residues.
  • the number of sugar residues is a statistical mean, which is based on the distribution customary for these compounds.
  • Alkyl glycosides based on C1 2 to G4 fatty alcohols and with up to 2.5 glycoside residues can be particularly suitable.
  • aqueous wetting agent solutions containing alkylglycoside contain non-surface-active electrolytes which are inert towards the starting materials.
  • non-surface-active electrolytes include, for example, the water-soluble chlorides, sulfates and nitrates of 1- to 3-valued metals, preferably the alkali, alkaline earth and earth metals.
  • additions of sodium sulfate and / or magnesium sulfate have proven successful.
  • alkyl glycoside-containing aqueous wetting agent solutions are preferably to be understood as meaning electrolyte-containing alkyl glycoside-containing aqueous wetting agent solutions.
  • the effect of the aqueous glyceride-containing wetting agent solutions can be improved by adding unsaturated natural fatty acid salts with more than 14 C atoms, preferably with 16 to 20 C atoms.
  • unsaturated natural fatty acids in the form of their alkali and / or alkaline earth salts, for example potassium oleate, have proven particularly useful.
  • the aqueous wetting agent solutions containing alkylglycoside according to the invention preferably contain 0.5 to 3 percent by weight alkylglycosides, 1 to 20 percent by weight inorganic electrolytes and 0 to 2 percent by weight unsaturated natural fatty acid salts, particularly preferably about 1 percent by weight alkylglycosides, 2 to about 10 percent by weight inorganic electrolytes and 0 to 1.5 Weight percent unsaturated natural fatty acid salts.
  • alkyl glycoside-containing aqueous wetting agent solutions according to the invention are expediently used in amounts such that 50 to 500 g, preferably 50 to 200 g, of wetting agent solution are present per 100 g of fat and / or oil.
  • Fats and oils which can be separated into solid and liquid constituents with the alkyl glycoside-containing aqueous wetting agent solutions according to the invention, are fatty acid ester mixtures of vegetable, animal and / or synthetic origin.
  • the fatty acid ester mixtures of vegetable origin include, for example, coconut, palm kernel and shea fat, palm, cottonseed, olive, soybean, peanut, linseed, rapeseed and castor oil.
  • Fatty acid ester mixtures of animal origin are, for example, butter, chicken and goose fat, lard, mutton and beef tallow, kidney and bone fats as well as the large number of different fish oils, tears, whale oils such as menhaden, herring and sperm oil and cod liver oil.
  • Synthetic fatty acid ester mixtures obtained from the above-mentioned vegetable and / or animal fatty acid ester mixtures by transesterification are also suitable.
  • Fatty acid ester mixtures from which saturated triglyceride portions have been separated are also suitable.
  • the separation of fatty acid ester mixtures is carried out according to the known cross-linking process - see, for example, the literature cited at the beginning - by transferring the starting materials to be separated into a dispersion of liquid and solid particles in aqueous alkylglycoside-containing wetting agent solution, separating this dispersion in 2 phases of different specific weights and separating the solid fatty acid ester components from the aqueous alkyl glycoside-containing wetting agent solution.
  • pulpy mixtures of crystalline and liquid components Since the achievable separation effect into solid and liquid components includes Depending on the nature of the solid fraction crystals, it is advisable to melt the starting mixtures completely and then slowly cool them down to the temperature at which the solid portions crystallize and then the wetting agent solution is to be added.
  • the aqueous wetting agent solution wets the solid components, thus separating them from the liquid fatty acid ester components and suspending them in the aqueous phase.
  • the liquid fatty acid ester components are emulsified in the aqueous phase under the action of the alkyl glycoside-containing solution.
  • the separation of the dispersion into a liquid phase with a lower specific weight, which contains the liquid fatty acid ester components, and into a water phase with a higher specific weight, which contains the solid fatty acid ester components takes place in conventional devices for separating several liquid phases according to their specific weights, for example in separating boxes , Centrifuges, plate separators or hydrocyclones.
  • the solid fatty acid ester constituents suspended in the water phase are advantageously separated from the wetting agent solution by heating the suspension to temperatures above the melting point of the solid fatty acid ester constituents and separating the two resulting liquid phases from one another in a manner known per se, for example by means of separators or centrifuges .
  • the resulting aqueous phase which contains the wetting agent contained in the solid components, is returned to the process. If desired, the solid fatty acid ester components can be washed again with water to completely remove the wetting agent.
  • a wetting agent solution was added, which consists of 205 g of water, 90 g of magnesium sulfate heptahydrate and 4.9 g of 62% alkylglycoside A (corresponding to 1% by weight of active substance in the wetting agent) solution).
  • the mixture was stirred at about 20 ° C. for 20 minutes and then separated in a cup centrifuge (Varifuge st, Heraeus / Christ company) at 4000 revolutions per minute in 5 minutes. It was separated into a wetting agent-free liquid phase and a heavier water phase in which the dispersed solids were.
  • the liquid palm oil constituents had an iodine number (according to Kaufmann) of 60.9, the solid palm oil constituents an iodine number of 37.1 and a rising melting point of 27.8 ° C.
  • the solid fraction was 65 at 20 ° C according to the NMR method (Bruker) Measure the percentage by weight of crystalline components.
  • the liquid and solid components behaved like 84: 16 by weight.
  • the iodine number of the liquid component was 60.1 and that of the solid component 32.8.
  • the rising melting point of the solid palm oil components was 28.4 ° C.
  • 75.4 percent by weight crystalline components could be determined by the NMR method (20 ° C.).
  • the solid fraction was determined by NMR spectroscopy at 20 ° C 59.1 wt .-% crystalline fractions.
  • the solid fraction was determined by the NMR method at 20 ° C 29 wt .-% crystalline fractions.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Health & Medical Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Saccharide Compounds (AREA)
  • Fats And Perfumes (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
EP86116026A 1985-11-29 1986-11-19 Verwendung von Alkylglycosiden zur Trennung von Fettsäureestergemischen Expired EP0224798B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3542226 1985-11-29
DE3542226 1985-11-29

Publications (2)

Publication Number Publication Date
EP0224798A1 EP0224798A1 (de) 1987-06-10
EP0224798B1 true EP0224798B1 (de) 1989-05-24

Family

ID=6287174

Family Applications (1)

Application Number Title Priority Date Filing Date
EP86116026A Expired EP0224798B1 (de) 1985-11-29 1986-11-19 Verwendung von Alkylglycosiden zur Trennung von Fettsäureestergemischen

Country Status (7)

Country Link
EP (1) EP0224798B1 (da)
JP (1) JPS62132531A (da)
DE (1) DE3663532D1 (da)
DK (1) DK551386A (da)
ES (1) ES2003554A6 (da)
GB (1) GB2183669B (da)
MY (1) MY100868A (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4861612A (en) * 1987-02-06 1989-08-29 Kao Corporation Method of separating oleaginous matter into components having various melting points
JP2989682B2 (ja) * 1991-04-04 1999-12-13 花王株式会社 液体脂肪酸及び固体脂肪酸の製造方法
US10188736B2 (en) 2013-09-30 2019-01-29 Enza Biotech Ab Surfactant composition

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB472086A (en) * 1936-08-18 1937-09-16 Schou Herbert Improvements in or relating to the preparation of emulsions
DE1267367C2 (de) * 1963-05-21 1978-04-20 Henkel KGaA, 4000 Dusseldorf Verfahren zur trennung von gemischen aus fluessigen und festen fettsaeuren

Also Published As

Publication number Publication date
MY100868A (en) 1991-05-16
ES2003554A6 (es) 1988-11-01
GB8626285D0 (en) 1986-12-03
GB2183669B (en) 1989-10-04
DK551386A (da) 1987-05-30
DK551386D0 (da) 1986-11-18
DE3663532D1 (en) 1989-06-29
GB2183669A (en) 1987-06-10
JPS62132531A (ja) 1987-06-15
EP0224798A1 (de) 1987-06-10

Similar Documents

Publication Publication Date Title
EP0555776A1 (de) Verfahren zur Isolierung und Reinigung von Fettsäuren und Hydroxyfettsäuren
DE2609705A1 (de) Verfahren zum entschleimen von triglyceridoelen
DE2448233A1 (de) Fettzusammensetzung
DE69811676T2 (de) Verfahren zur verminderung des gehaltes an langkettigen gesättigten fettsäuren in fettsäurezusammensetzungen
CH630403A5 (de) Verfahren zur entfernung von verunreinigungen aus triglyceridoelen.
DE69511435T2 (de) Fraktionierung von triglyceridölen
EP0224798B1 (de) Verwendung von Alkylglycosiden zur Trennung von Fettsäureestergemischen
DE2446775C2 (de) Verfahren zur Zerlegung von Steringemischen in an Campesterin angereicherte Fraktionen und an Sitosterin angereicherte Fraktionen
DE1418884A1 (de) Verfahren zur Herstellung von Fetten,insbesondere von Speisefetten mit einem vom Ausgangsmaterial abweichenden Schmelzverhalten
DE3885118T2 (de) Verfahren zum Trennen von Ölstoffen in Bestandteile mit verschiedenen Schmelzpunkten.
DE1617023C3 (de) Verfahren zum Abtrennen von Fettkristallen aus Fett- bzw. Fettsäuregemischen
DE2309165C2 (de) Verfahren zur Auftrennung eines Gemisches von flüssigen und kristallinen Fettsäuretriglyceriden in zwei Fraktionen
DE2053257C3 (de) Verfahren zur Trennung von Fettsäureestergemischen in Bestandteile verschiedener Schmelzpunkte
DE19906551C1 (de) Verfahren zur Herstellung von Phytosterinen
DD297396A5 (de) Verfahren zur behandlung von fettsaeuren
DE2420623C2 (de) Verfahren zur Trennung von Fettstoffgemischen
DE2100022C3 (de) Verfahren zur Trennung von Fettstoffgemischen in Bestandteile verschiedener Schmelzpunkte
DE977544C (de) Verfahren zur Trennung von Carbonsaeureestergemischen in Bestandteile verschiedener Schmelzpunkte
EP0014439A2 (de) Verfahren zur Trennung von Fettstoffgemischen in Bestandteile verschiedener Schmelzpunkte
DE1692567B2 (de) Verfahren zur herstellung von wasserloeslichen und/oder wasserdispergierbaren phosphatidemulgatoren
DE1267367C2 (de) Verfahren zur trennung von gemischen aus fluessigen und festen fettsaeuren
CH646069A5 (de) Verfahren zur isolierung eines materials aus einer loesung.
DE1107659B (de) Verfahren zur Trennung von Gemischen hoehermolekularer Fettalkohole
DE602005001989T2 (de) Verfahren zur Herstellung von Kalium Salz von Dinitrobenzofuroxan
DE912153C (de) Verfahren zur Entfernung von Wismut aus Blei

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH DE FR IT LI NL SE

17P Request for examination filed

Effective date: 19871106

17Q First examination report despatched

Effective date: 19880713

RBV Designated contracting states (corrected)

Designated state(s): BE DE FR IT NL

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): BE DE FR IT NL

REF Corresponds to:

Ref document number: 3663532

Country of ref document: DE

Date of ref document: 19890629

ET Fr: translation filed
ITF It: translation for a ep patent filed
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
ITTA It: last paid annual fee
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19921130

Year of fee payment: 7

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 19921223

Year of fee payment: 7

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19931026

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19931110

Year of fee payment: 8

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Effective date: 19931130

BERE Be: lapsed

Owner name: HENKEL K.G.A.A.

Effective date: 19931130

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19940601

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Effective date: 19950731

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19950801

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES;WARNING: LAPSES OF ITALIAN PATENTS WITH EFFECTIVE DATE BEFORE 2007 MAY HAVE OCCURRED AT ANY TIME BEFORE 2007. THE CORRECT EFFECTIVE DATE MAY BE DIFFERENT FROM THE ONE RECORDED.

Effective date: 20051119