EP0224798B1 - Use of alkyl glycosides in the separation of fatty acid ester mixtures - Google Patents
Use of alkyl glycosides in the separation of fatty acid ester mixtures Download PDFInfo
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- 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
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- 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.)
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- -1 alkyl glycosides Chemical class 0.000 title claims description 57
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 40
- 229930195729 fatty acid Natural products 0.000 title claims description 40
- 239000000194 fatty acid Substances 0.000 title claims description 40
- 239000000203 mixture Substances 0.000 title claims description 24
- 238000000926 separation method Methods 0.000 title claims description 19
- 229930182470 glycoside Natural products 0.000 title description 14
- 239000007787 solid Substances 0.000 claims description 44
- 239000000080 wetting agent Substances 0.000 claims description 40
- 239000007788 liquid Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000003792 electrolyte Substances 0.000 claims description 6
- 125000003563 glycoside group Chemical group 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 12
- 239000003925 fat Substances 0.000 description 12
- 235000019197 fats Nutrition 0.000 description 12
- 229910052740 iodine Inorganic materials 0.000 description 12
- 239000011630 iodine Substances 0.000 description 12
- 235000019482 Palm oil Nutrition 0.000 description 10
- 239000002540 palm oil Substances 0.000 description 9
- 239000000470 constituent Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000013543 active substance Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 description 3
- 229940061634 magnesium sulfate heptahydrate Drugs 0.000 description 3
- 230000000630 rising effect Effects 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 229940096992 potassium oleate Drugs 0.000 description 2
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- 241000272814 Anser sp. Species 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 241000273930 Brevoortia tyrannus Species 0.000 description 1
- 241000252203 Clupea harengus Species 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 235000012716 cod liver oil Nutrition 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002338 glycosides Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000019514 herring Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
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.
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- 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)
Description
Die Erfindung betrifft Trennungen von in Fetten und Ölen vorkommenden Fettsäureestergemischen nach dem an sich bekannten Umnetzverfahren unter Verwendung alkylglycosidhaltiger wässriger Netzmittellösungen.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.
Natürliche Fette und Öle unterscheiden sich in Kettenlänge und Sättigungsgrad ihrer Fettsäureesterkomponenten und damit auch in ihren physikalischen Eigenschaften. So liegen die Schmelzpunkte gesättigter Fettsäureester oberhalb Raumtemperatur, während ungesättigte Fettsäureester bei Raumtemperatur flüssig sind. Die Trennung von Fetten in feste und flüssige Komponenten stellt eine Auftrennung in stärker gesättigte und stärker ungesättigte Anteile dar.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.
Eine Trennung in feste und flüssige Bestandteile kann in vorteilhafter Weise durch das sogenannte Umnetzverfahren, eine Trennung in Gegenwart wäßriger netzmittelhaftiger Lösungen erreicht werden, wobei die festen Anteile durch Benetzung von der wäßrigen Phase aufgenommen werden.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.
In den Patentschriften DE-PS 977 544, DE-PS 2 053 257 und US 1 326 049 werden Verfahren zur Trennung von Fettsäure- und Fettsäureestergemischen, insbesondere Triglyceridgemischen, in Bestandteile verschiedener Schmelzpunkte mit Hilfe wässriger Netzmittellösungen beschrieben. Diese Netzmittellösungen enthalten beispielsweise Fettalkoholsulfate oder Alkylbenzolsulfonate. Bei Fettsäuretrennungen haben sich Fettalkoholsulfate mit 10 bis 12 Kohlenstoffatomen in der Kette besonders bewährt.In the patents DE-PS 977 544, DE-PS 2 053 257 and US 1 326 049 processes for the separation of fatty acid and fatty acid ester mixtures, in particular triglyceride mixtures, are described in components of different melting points with the aid of aqueous wetting agent solutions. These wetting agent solutions contain, for example, fatty alcohol sulfates or alkylbenzenesulfonates. When separating fatty acids, fatty alcohol sulfates with 10 to 12 carbon atoms in the chain have proven particularly useful.
Aus der JP 57/197 sind Gemische aus Fettalkoholsulfat und Sorbitanfettsäureestern als Netzmittel zur Fettsäure-und Fettrennung in feste und flüssige Bestandteile bekannt. In den Referaten von Chemical Abstracts CA 100. 123 162v und CA 96, 144 899e werden Umnetzungen von Fetten unter Verwendung von Netzmitteln enthaltend Sucrose-Fettsäureester beziehungsweise Gemische aus Sorbitan-oder Polyoxyethylensorbitanfettsäureestern und Fettsäuresalzen beschrieben. Als nachteilig erweist sich jedoch bei Verwendung von Sorbitanfettsäureestem die Tatsache, daß Sorbitanfettsäureester in alkalischen Medien, insbesondere bei höheren Temperaturen, der Hydrolyse unterliegen können.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. However, the fact that 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.
Die Aufgabe der Erfindung bestand in der Bereitstellung von Netzmittellösungen, die gleich gute Trenneffekte von Fetten und Ölen in feste und flüssige Bestandteile wie Netzmittellösungen des Standes der Technik zeigen, die jedoch hydrolysestabile Substanzen enthalten, die aus nachwachsenden Rohstoffen hergestellt werden.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.
Überraschenderweise hat sich jetzt gezeigt, daß Alkylglycosidhaltige, wässrige Netzmittellösungen besonders geeignet sind, die erfindungsgemäße Aufgabe zu lösen, obwohl an sich Alkylglycoside und ihre Netzmitteleigenschaften seit Jahren bekannt sind.Surprisingly, it has now been shown that 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.
Gegenstand der Erfindung ist dementsprechend die Verwendung von Alkylglycosiden mit bis zu 24 C-Atomen in der Alkylkette als Netzmittel in wässrigen Netzmittellösungen zur Trennung von Fettsäureestergemischen in feste und flüssige Bestandteile nach dem an sich bekannten Umnetzverfahren.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.
Alkylglycosid-hahige Netzmittellösungen besitzen gegenüber Netzmittellösungen aus dem Stand der Technik den großen Vorteil, daß sie hydrolysestabil sind und daß die in diesen enthaltenen Alkylglycoside eine bekannte, aus nachwachsenden Rohstoffen nach gängigen Methoden der organischen Synthese herstellbare Substanzklasse darstellen. In diesem Zusammenhang wird auf die US-Patentschriften 3 839 318, 3 707 535 und 3 547828, die deutschen Offenlegungsschriften 30 01 064, 20 36 472, 19 43 689 und 19 05 523 sowie auf die europäische Patentanmeldung 77 167 verwiesen. Die erfindungsgemäß eingesetzten Alkylglycoside leiten sich insbesondere von Fettalkoholen und Zuckern ab. Bevorzugt werden Alkylglycoside mit einem Ce-, Ce-, C10-, C12-, C14-, Cle- und/oder C18-Alkylrest, der geradkettig oder verzweigt, gesättigt aber auch einfach oder mehrfach olefinisch ungesättigt sein und beispielsweise bis zu 3 Doppelbindungen aufweisen kann, oder Mischungen derartiger Verbindungen. Besonders geeignet sind Alkylglycoside deren Alkyl- oder Alkenylrest 10 bis 16 C-Atome enthält. Bezüglich des Saccharidrestes der Alkylglycoside gilt, daß sich sowohl Alkylmonoglycoside, bei denen ein cyclischer Zuckerrest an den Alkohol gebunden ist, eignen, aber auch Oligomere mit vorzugsweise bis zu 8, insbesondere bis zu 3 glycosidisch gebundenen Zuckerresten, beispielsweise Glucose- oder Maftoseresten. Dabei ist die Anzahl der Zuckerreste ein statistischer Mittelwert, dem die bei diesen Verbindungen übliche Verteilung zugrunde liegt. Alkylglycoside auf der Basis von C12- bis G4-Fettalkoholen und mit bis zu 2,5 Glycosidresten können besonders geeignet sein.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. In this connection, reference is made to US Pat. Nos. 3,839,318, 3,707,535 and 3,547,828, German Offenlegungsschriften 30 01 064, 20 36 472, 19 43 689 and 19 05 523 and European patent application 77 167. 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. With regard to the saccharide residue of the alkyl glycosides, 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.
Die Wirkung der alkylglycosidhaltigen wässrigen Netzmittellösungen wird verbessert, wenn sie nichtoberflächenaktive, gegenüber den Ausgangsstoffen inerte Elektrolyte enthalten. Hierzu gehören beispielsweise die wasserlöslichen Chloride, Sulfate und Nitrate von 1- bis 3-wehrwertigen Metallen, vorzugsweise der Alkali-, Erdalkali- und Erdmetalle. Insbesondere haben sich Zu sätze von Natriumsulfat und/oder Magnesiumsulfat bewährt. Im Zusammenhang mit der vorliegenden Erfindung sind unter alkylglycosidhaltigen, wässrigen Netzmittellösungen bevorzugt elektrolythaltige alkylglycosidhaltige wässrige Netzmittellösungen zu verstehen.The effect of the aqueous wetting agent solutions containing alkylglycoside is improved if they contain non-surface-active electrolytes which are inert towards the starting materials. These include, for example, the water-soluble chlorides, sulfates and nitrates of 1- to 3-valued metals, preferably the alkali, alkaline earth and earth metals. In particular, additions of sodium sulfate and / or magnesium sulfate have proven successful. In connection with the present invention, alkyl glycoside-containing aqueous wetting agent solutions are preferably to be understood as meaning electrolyte-containing alkyl glycoside-containing aqueous wetting agent solutions.
Darüber hinaus kann die Wirkung der alkylglycosidhaltigen wässrigen Netzmittellösungen durch einen Zusatz an ungesättigten natürlichen Fettsäuresalzen mit mehr als 14 C-Atomen, vorzugsweise mit 16 bis 20 C-Atomen verbessert werden. Insbesondere haben sich ungesättigte natürliche Fettsäuren in Form ihrer Alkali- und/oder Erdalkalisalze, beispielsweise Kaliumoleat, bewährt.In addition, 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.
Die erfindungsgemäßen alkylglycosidhaltigen wässrigen Netzmittellösungen enthalten bevorzugt 0,5 bis 3 Gewichtsprozent Alkylglycoside, 1 bis 20 Gewichtsprozent anorganische Elektrolyte und 0 bis 2 Gewichtsprozent ungesättigte natürliche Fettsäuresalze, besonders bevorzugt etwa 1 Gewichtsprozent Alkylglycoside, 2 bis etwa 10 Gewichtsprozent anorganische Elektrolyte und 0 bis 1,5 Gewichtsprozent ungesättigte natürliche Fettsäuresalze.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.
Zweckmäßigerweise werden die erfindungsgemäßen alkylglycosidhaltigen wässrigen Netzmittellösungen in solchen Mengen eingesetzt, daß pro 100 g Fett und/oder Öl, 50 bis 500 g, vorzugsweise 50 bis 200 g Netzmittellösung vorhanden sind.The 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.
Fette und Öle, die mit den erfindungsgemäßen alkylglycosidhaltigen wässrigen Netzmittellösungen in feste und flüssige Bestandteile getrennt werden können, sind Fettsäureestergemische pflanzlichen, tierischen und/oder synthetischen Ursprungs.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.
Zu den Fettsäureestergemischen pflanzlichen Ursprungs gehören beispielsweise Kokos-, Palmkern-und Sheafett, Palm-, Baumwollsaat-, Oliven-, Soja-, Erdnuß-, Lein-, Raps- und Rizinusöl. Fettsäureestergemische tierischen Ursprungs sind beispielsweise Butter, Hühner- und Gänsefett, Schweineschmalz, Hammel- und Rindertalg, Nieren- und Knochenfette sowie die große Zahl der verschiedenen Fischöle, Trane, Walöle wie beispielsweise Menhaden-, Herings- und Spermöl und Lebertrane. Weiterhin eignen sich auch synthetische Fettsäureestergemische, die aus den obengenannten pflanzlichen und/oder tierischen Fettsäureestergemischen durch Umesterung erhalten werden. Fettsäureestergemische, von denen gesättigte Triglyceridanteile abgetrennt worden sind, sind ebenfalls geeignet.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.
Die Trennung von Fettsäureestergemischen erfolgt nach dem an sich bekannten Umnetzverfahren - siehe hierzu beispielsweise die eingangs zitierte Literatur - durch Überführen der zu trennenden Ausgangsstoffe in eine Dispersion flüssiger und fester Partikel in wässriger alkylglycosidhaltiger Netzmittellösung, Trennen dieser Dispersion in 2 Phasen verschiedener spezifischer Gewichte und Trennen der festen Fettsäureesterbestandteile aus der wässrigen alkylglycosidhaltigen Netzmittellösung. Zur Herstellung von Dispersionen flüssiger und fester Komponenten in wässrigen alkylglycosidhaltigen Netzmittellösungen setzt man zweckmäßigerweise breiige Gemische aus kristallinen und flüssigen Anteilen ein. Da der erzielbare Trenneffekt in feste und flüssige Bestandteile u.a. von der Beschaffenheit der Festanteilkristalle abhängt, empfiehlt es sich, die Ausgangsgemische vollständig aufzuschmelzen und anschließend langsam auf die Temperatur abzukühlen, bei der die Festanteile auskristallisieren und anschließend die Netzmittellösung zugegeben werden soll.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. For the preparation of dispersions of liquid and solid components in aqueous alkylglycoside-containing wetting agent solutions, it is expedient to use 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.
Die wässrige Netzmittellösung benetzt die festen Komponenten, trennt sie damit von den flüssigen Fettsäureesteranteilen und suspendiert sie in der wässrigen Phase. Die flüssigen Fettsäureesterbestandteile werden unter der Wirkung der alkylglycosidhaltigen Lösung in der wässrigen Phase emulgiert. Die Trennung der Dispersion in eine Flüssigphase mit geringerem spezifischen Gewicht, die die flüssigen Fettsäureesterbestandteile enthält, und in eine Wasserphase mit höherem spezifischem Gewicht, die die festen Fettsäureesterkomponenten enthält, erfolgt in üblichen Einrichtungen zur Trennung mehrerer flüssiger Phasen nach ihren spezifischen Gewichten, beispielsweise in Scheidekästen, Zentrifugen, Tellerseperatoren oder Hydrocyclonen.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.
Die in der Wasserphase suspendierten festen Fettsäureesterbestandteile werden in vorteilhafter Weise von der Netzmittellösung abgetrennt, indem die Suspension auf Temperaturen oberhalb des Schmelzpunktes der festen Fettsäureesterbestandteile erhitzt wird und die beiden entstehenden flüssigen Phasen in an sich bekannter Weise, beispielsweise durch Abscheider oder Zentrifugen, voneinander getrennt werden. Die anfallende wäßrige Phase, die das in den Festanteilen enthaltene Netzmittel enthält, wird in das Verfahren zurückgeführt. Gewünschtenfalls können die festen Fettsäureesterbestandteile noch einmal mit Wasser zur vollständigen Entfernung des Netzmittels gewaschen werden.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.
Folgende Alkylglycoside wurden in wässrigen Netzmittellösungen eingesetzt:
- Alkylglycosid A: Ein C12/C14-Alkyloligoglucosid (Oligomerisierungsgrad 1,5), desssen Alkylreste sich von einem n-DodecanoUn-Tetradecanolgemisch im Gewichtsverhältnis 70 : 30 ableiten.
- Alkylglycosid B: Ein C12/C14-Alkyloligoglucosid (Oligomerisierungsgrad 2,2), dessen Alkylreste sich von einem n-DodecanoVn-Tetradecanolgemisch im Verhältnis 70 : 30 ableiten.
- Alkylglycoside A: A C 12 / C 14 alkyl oligoglucoside (degree of oligomerization 1.5), the alkyl residues of which are derived from an n-dodecanoun-tetradecanol mixture in a weight ratio of 70:30.
- Alkylglycoside B: A C 12 / C 14 alkyl oligoglucoside (degree of oligomerization 2.2), the alkyl residues of which are derived from an n-dodecanoVn-tetradecanol mixture in a ratio of 70:30.
150 g Palmöl wurden bei etwa 40 °C aufgeschmolzen und unter Rühren bei 20 °C über 3 Tage zur Kristallisation gebracht. Zu dem erhaltenen breiigen Gemisch aus flüssigen und festen Bestandteilen wurde eine Netzmittellösung hinzugefügt, die sich aus 205 g Wasser, 90 g Magnesiumsulfatheptahydrat und 4,9 g 62 %igem Alkylglycosid A (entsprechend 1 Gewichtsprozent Aktiv substanz in der Netzmittellösung) zusammensetzte. Die Mischung wurde 20 Minuten bei etwa 20 °C gerührt und anschließend in einer Becherzentrifuge (Varifuge st, Firma Heraeus/Christ) bei 4000 Umdrehungen pro Minute in 5 Minuten getrennt. Es erfolgte Auftrennung in eine netzmittelfreie Flüssigphase und in eine schwerere Wasserphase, in der sich die dispergierten Festanteile befanden.150 g of palm oil were melted at about 40 ° C and brought to crystallization with stirring at 20 ° C for 3 days. To the resulting pulpy mixture of liquid and solid components, 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.
Nach Abtrennung der flüssigen Palmölfraktion wurde die Wasserphase mit den Festanteilen auf etwa 50 °C erhitzt und das geschmolzene Fett durch Zentrifugieren abgetrennt. Die erhaltenen flüssigen und festen Fettsäureesterbestandteile verhielten sich gewichtsmäßig wie 81:19. Die flüssigen Palmölbestandteile besaßen eine Jodzahl (nach Kaufmann) von 60,9, die festen Palmölbestandteile eine Jodzahl von 37,1 und einen Steigschmelzpunkt von 27,8 °C. Im Festanteil wurden nach der NMR-Methode (Bruker) bei 20 °C 65 Gewichtsprozent kristalline Anteile vermessen.After the liquid palm oil fraction had been separated off, the water phase with the solids was heated to about 50 ° C. and the melted fat was separated off by centrifugation. The liquid and solid fatty acid ester components obtained behaved as 81:19 by weight. 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.
Wurde das Alkylglycosid A durch eine gleichgroße Menge an Alkylglucosid B ersetzt und unter sonst gleichen Bedingungen Palmöl in flüssige und feste Bestandteile getrennt, verhielten sich die Flüssig-und Festanteile gewichtsmäßig wie 84 : 16. Die Jodzahl des Flüssiganteils betrug 60,1, die des Festanteils 32,8. Der Steigschmelzpunkt der festen Palmölkomponenten lag bei 28,4 °C. Im Festanteil konnten 75,4 Gewichtsprozent kristalline Anteile nach der NMR-Methode (20 °C) ermittelt werden.If the alkyl glycoside A was replaced by an equal amount of alkyl glucoside B and palm oil was separated into liquid and solid components under otherwise identical conditions, 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. In the solid fraction, 75.4 percent by weight crystalline components could be determined by the NMR method (20 ° C.).
Die Trennung von Kokosöl in feste und flüssige Bestandteile wurde unter den in Beispiel 1 angegebenen Bedingungen durchgeführt. Die Ergebnisse sind in untenstehender Tabelle zusammengefaßt.
150 g Palmöl wurden bei etwa 40 °C aufgeschmolzen und nach Zusatz von 1,5 g Kaliumoleat unter Rühren bei 20 °C über 3 Tage zur Kristallisation gebracht. Anschließend wurde eine Lösung von 90 g Magnesiumsulfatheptahydrat und 5 g 60%igem Alkylglycosid B (entsprechend 3 g Aktivsubstanz) in 205 g Wasser zugesetzt. Die Mischung wurde 20 Minuten bei 20 °C gerührt. Die Trennung erfolgte unter den in Beispiel 1 angegebenen Bedingungen. Die erhaltenen festen und flüssigen Fettsäureesterbestandteile verhielten sich gewichtsmäBig wie 19,5 : 80,5. Jodzahl des Flüssiganteils: 57,6 Jodzahl des Festanteils: 38,3 Steigschmetzpunkt des Festanteils: 27,7 °C150 g of palm oil were melted at about 40 ° C. and, after addition of 1.5 g of potassium oleate, they were brought to crystallization with stirring at 20 ° C. over 3 days. A solution of 90 g of magnesium sulfate heptahydrate and 5 g of 60% alkylglycoside B (corresponding to 3 g of active substance) in 205 g of water was then added. The mixture was stirred at 20 ° C for 20 minutes. The separation was carried out under the conditions given in Example 1. The solid and liquid fatty acid ester components obtained behaved by weight as 19.5: 80.5. Iodine number of the liquid portion: 57.6 Iodine number of the solid portion: 38.3 Rise smear point of the solid portion: 27.7 ° C
Im Festanteil wurden NMR-spektroskopisch bei 20 °C 59,1 Gew.-% kristalline Anteile ermittelt.The solid fraction was determined by NMR spectroscopy at 20 ° C 59.1 wt .-% crystalline fractions.
200 g Schweineschmalz wurden bei etwa 40 °C aufgeschmolzen und unter Rühren wie folgt abgekühlt: 1 Stunde bei 26 °C, 1 Stunde bei 24 °C, 1 Stunde bei 22°C, 1 Stunden bei 21 °C und 3 Stunden bei 20°C. Anschließend wurde eine Netzmittellösung zugefügt, die sich aus 286 g Wasser, 6 g Natriumsulfat, 3 g Natriumoleat und 5 g 60-Gew.-%igem Alkylglycosid B (entsprechend 1 Gew.-% Aktivsubstanz in der Netzmittellösung) zusammensetzte. Die weitere Verfahrensweise entsprach der in Beispiel 1 beschriebenen. Die erhaltenen flüssigen und festen Fettsäureesterbestandteile verhielten sich gewichtsmäßig wie 80,5:19,5.
- Jodzahl des Flüssiganteils: 70,6
- Trübungspunkt des Flüssiganteils: 6 °C
- Jodzahl des Festanteils: 58,3
- Steigschmelzpunkt des Festanteils: 35,9 °C
- Iodine number of the liquid portion: 70.6
- Cloud point of the liquid portion: 6 ° C
- Iodine number of the solid component: 58.3
- Rise melting point of the solid portion: 35.9 ° C
Im Festanteil wurden nach der NMR-Methode bei 20 °C 29 Gew.-% kristalline Anteile ermittelt.The solid fraction was determined by the NMR method at 20 ° C 29 wt .-% crystalline fractions.
Wurde die Trennung von Schweineschmalz unter Verwendung von 300 g einer wäßrigen Netzmittellösung mit 1 Gew.-% Aktivsubstanz des Alkylglycosids B und 5 Gew.-% Magnesiumsulfatheptahydrat nach obiger Vorgehensweise durchgeführt, so wurden Flüssig- und Festanteil im Gewichtsverhältnis 65 : 35 erhalten.
- Jodzahl des Flüssiganteils: 70,5
- Trübungspunkt des Flüssiganteils: 6 °C
- Jodzahl des Festanteils: 51,1
- Steigschmelzpunkt des Festanteils: 38 °C
- Iodine number of the liquid portion: 70.5
- Cloud point of the liquid portion: 6 ° C
- Iodine number of the solid component: 51.1
- Rising melting point of the solid component: 38 ° C
Im Festanteil wurden nach der NMR-Methode bei 20 °C 43 Gew.-% kristalline Anteile ermittelt.In the solid fraction, 43% by weight crystalline portions were determined by the NMR method at 20 ° C.
Claims (6)
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JP (1) | JPS62132531A (en) |
DE (1) | DE3663532D1 (en) |
DK (1) | DK551386A (en) |
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JP2989682B2 (en) * | 1991-04-04 | 1999-12-13 | 花王株式会社 | Method for producing liquid fatty acid and solid fatty acid |
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1986
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GB2183669A (en) | 1987-06-10 |
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