DE1668629A1 - Process for the production of surface-active substances - Google Patents
Process for the production of surface-active substancesInfo
- Publication number
- DE1668629A1 DE1668629A1 DE19671668629 DE1668629A DE1668629A1 DE 1668629 A1 DE1668629 A1 DE 1668629A1 DE 19671668629 DE19671668629 DE 19671668629 DE 1668629 A DE1668629 A DE 1668629A DE 1668629 A1 DE1668629 A1 DE 1668629A1
- Authority
- DE
- Germany
- Prior art keywords
- fatty acid
- acid esters
- carbohydrates
- sucrose
- foam
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/02—Foam dispersion or prevention
- B01D19/04—Foam dispersion or prevention by addition of chemical substances
- B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/06—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical being a hydroxyalkyl group esterified by a fatty acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/08—Polyoxyalkylene derivatives
-
- 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
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
-
- 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
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
Description
Verfahren zur Herstellung eberflächenaktiver Stoffs Zusatz zu Patent-Anm. R 44 242 IVb/12 o Die Erfindung betrifft ein Verfahren zur Herstellung oberflächenaktiver Stoffe, bei dom nach Patent.... (Pat.Anm. Process for the production of surface-active substance Addition to patent application R 44 242 IVb / 12 o The invention relates to a process for the production of surface-active substances Materials, at dom according to patent .... (Pat.
R 44 242 IVb/12 o) in einem einsigen Verfahrensschritt ohne Anwendung eines Lösungsmittels ein oder sohrere Kohlenwasserateffe, ein oder mehrere Fetteäureeater und ein oder mebrere Alkylenoxide in Gegenwart eines Katalynators fUr die Oxyx. alkylierung und die Umesterung miteinander zur Reaktiv gebraoht werden. Die nach diesen Verfahren hergestellten oberflächenaktiven Stoffe Bind ale Dotergenz, Netzmittel, Lösungsvermittler, Emulgator sowohl fUr Emulsionen von Tasser in Öl ale such fUr Emulsionen von 01 in Wasser sowie ale eohaumhemmendes Mittel geeignet, je nach do= Verhältnis, mit dom die Reagensien bei der Herstellung dea oberflächenaktiven Steffea eingesetst werden.R 44 242 IVb / 12 o) in a single process step without application of a solvent, one or more hydrocarbons, one or more fatty acid ethers and one or more alkylene oxides in the presence of a catalyst for the oxyx. alkylation and transesterification with each other to reactive brewed will. The surface-active substances produced by this process bind ale Dotergent, wetting agent, solubilizer, emulsifier both for emulsions from Tasser in oil as well as for emulsions of oil in water as well as all anti-inflammatory agents suitable, depending on the do = ratio, with dom the reagents in the preparation of dea surface-active Steffea can be used.
Der vorliegenden Erfindung liegt die Aufgabe zugrunde, durch disse Verfabron schaumhindernde Mittel su schaffen, die absolut ungiftig sind. Dieze aufgabe wird nach der Erfindung daduroh gelöst, dal lei des einganga gonannten Verfabron die Staffe in einer Mange eingeaetzt werden, die im Verhältnis sun m Gesamtgewicht fUr die Kohlenwaaaerstoffe 5 bis 25%, die Fettsäureester 50 bis 80% und die Alkylenoxide 10 bis 40% beträgt.The present invention is based on the object by this Verabron create anti-foaming agents that are absolutely non-toxic. This task is solved according to the invention daduroh, dal lei of the gonamed Verabron the staffe can be used in an amount corresponding to the ratio of sun m total weight for the carbons 5 to 25%, the fatty acid esters 50 to 80% and the alkylene oxides 10 to 40%.
Ale Kohlenwasserstoff wird vorzugsweise Saccharose in kristalliner Form eingesetzt, beispielsweise in Form von weigem zucker, Rohzucker oder getrockneter Molasse. Wenn der Antell der ohlenwasserstoffe, die in die schaumhindernden Verbindungen eingegeben werden, können ale Sachharose-Lieferant Zwischenprodukte der zuckerherstellung oder der Zuokerraffinierung benutzt werden, wie beispielsweise Dicksaft, Dünnsaft, Sirup oder Melasse.All hydrocarbons are preferably sucrose in crystalline form Form used, for example in the form of white sugar, raw sugar or dried Molasses. If the antell of the hydrocarbons, which in the foam-preventing compounds All Sachharose suppliers can enter intermediate products in sugar production or sugar refining, such as thick juice, thin juice, syrup or molasses.
Es ist nicht ausgeschlossen, andere Kohlenwasserstoffe su verwenden. Beiapielaweiee kdnnte allein odor in einer Misahung mit Saccharose Maltose verwendet werden, die durch eine partielle Amylase-Hydrolyse von Stärke gewonnen wurde.The use of other hydrocarbons is not excluded. Beiapielaweiee could be used alone or in a mixture with sucrose maltose obtained by partial amylase hydrolysis of starch.
Ale Pettäureester werden vorzugsweise lette oder Ole tieriechen oder pflanzlichen Uraprungs aowie Fettsäureester von Methyl- oder Äthylalkehel verwendet, deren Fettsäuren 6 bis 30 Kehlenstoffatome enthalten.All fatty acid esters are preferably lette or ole animal or vegetable origin as well as fatty acid esters of methyl or ethyl alcohol used, whose fatty acids contain 6 to 30 fillet atoms.
Ale Alkylenoxid wird vorzugsweise Athylenexid, Propylenoxid der eine Miechung dieser beiden Oxide verwendet.Ale alkylene oxide is preferably ethylene exide, propylene oxide is the one Used in a mixture of these two oxides.
Geeignete fatalyaatoren eind energanische oder organisohe Basen und basische Salze.Suitable fatalyaatoren and energetic or organic bases and basic salts.
Weitere Einzelheiten und Auegeataltungen der Erfindung sind der folgenden Beachreibung von Beispielen sur Herstellung der ertlndungagem§ßen achaumhemmenden Stoffe su entnehmen : Beispiel 1 In einen Autoklaven werden gleichzeitig 100 g einer Raffinierkläre mit 70° Brix, 500 g Palmöl und 10 g KOH eingegeben und ea wird die Mischung auf eine Temperatur zwischen 100 und 20°C gebracht. Es wird mit Stickstoff und anschließend mit Propylenoxid gespult. Danach wird unter einem Druck von 3 kg/cm2 eine Menge von 430 g Propylenexid hinzugefügt. Nach der Reaktien erbdit man die schaumhindernds Verbindung A der Tafel 1.Further details and embodiments of the invention are as follows See examples for the production of the foam-inhibiting substances Take substances below: Example 1 In an autoclave are simultaneously Enter 100 g of a refining clarifier with 70 ° Brix, 500 g of palm oil and 10 g of KOH and ea the mixture is brought to a temperature between 100 and 20 ° C. It will flushed with nitrogen and then with propylene oxide. After that, under a Pressure of 3 kg / cm2 added an amount of 430 g of propylene exide. After the reactions The foam-preventing connection A of panel 1 is found.
Beispiel 2 Man verfährt wie im Belepiel 1, indem 100 g Saccharose in Form von Rchzucker, 650 g Talg, 10 g KOH und 250 g Propylenoxid eingesetzt werden. Man erhält die schaumhemmende Verbindung B der Tafel 1.Example 2 The procedure is as in Belepiel 1, adding 100 g of sucrose in the form of raw sugar, 650 g of tallow, 10 g of KOH and 250 g of propylene oxide can be used. The foam-inhibiting compound B of Table 1 is obtained.
Beispiel 3 Man verfährt unter Einsatz von 250 g Ablauf ven 76° Brix und 87% Reinheit, 600 g Kakaobutter, 8 g KOH und 250 g Propylenexid wie in Beispiel 1. Man erhält aut dlese Weise die schaumhemmende Verbindung C der Tafel 1.Example 3 The procedure is followed using 250 g of 76 ° Brix drain and 87% purity, 600 g cocoa butter, 8 g KOH and 250 g propylene exide as in example 1. The foam-inhibiting compound C of table 1 is obtained in this manner.
Beispiel 4 Man verfährt wie im Beispiel 1 unter Bineats on 395 g getrockneter Melaase, 540 g Talg, 8 g KOH und 230 g Propylenoxid. Das Ergebnis ist die schaumhemmende Verbindung D der Tafel 1.Example 4 The procedure is as in Example 1, using 395 g of dried bineats Melaase, 540 g tallow, 8 g KOH and 230 g propylene oxide. The result is the anti-foam Connection D of table 1.
Beispiel5 Man verfährt wie im Beispiel 1 unter Einsatz von 100 g unverdnderter Meulasse, 700 g Stearinsäuremethylester, 10 g KOH und 250 g Propylenoxid. Nach der Umestsung des Propylenoxid wird unter RUbron eine Temperatur zwischen 100 und 150°C aufrechterhalten, während der Druck in Autoklaven gesenkt wird, um das Methanol abzudestillieren.Example 5 The procedure is as in Example 1 using 100 g of unchanged Meulasse, 700 g of methyl stearate, 10 g of KOH and 250 g of propylene oxide. After Transesterification of the propylene oxide is a temperature between 100 and 150 ° C under RUbron maintained while the autoclave pressure is lowered to release the methanol to distill off.
Auf dièse Weise wird die schaumhemmende Verbindung E Der Tafel 1 erhalten.In this way the foam-inhibiting compound E of Table 1 is obtained.
Beispiel 6 Man verfährt wie im Beispiel 1 unter Einsatz von 50 g Saccharose, 750 g Talg 10 g KOH und 200 g Äthylenodix, Man erhält die schaumhemmende Verbindung G der Tatel 1.Example 6 The procedure is as in Example 1 using 50 g of sucrose, 750 g tallow 10 g KOH and 200 g Äthylenodix, the foam-inhibiting compound is obtained G of Tatel 1.
Beispiel 7 Man verfährt wid im Beispiel 1 unter Einsatz von 100 g Saccharose, 650 g Palmöl, 10 g KOH, 100 g Athylenoxid und 150 g Propylonesld. Man erhält auf diese Weise die eohaumhemmende Yerbindung I der label 1.Example 7 Example 1 is repeated using 100 g Sucrose, 650 g palm oil, 10 g KOH, 100 g ethylene oxide and 150 g Propylonesld. In this way, the eoha-inhibiting compound I of the label is obtained 1.
Die erfindungagemäßen schaushemmenden Verbindungen können so Verwendung finden, wie sie sind, emulgiert in Waeeer *der godet in einem flüssigen Kohlenwasserstoff. Als flüssiger Kohlenwasserstoff kommen leichtes Heizöl, Gasöl, mobwares Hoirs paraffinische Kohlenwasserstoffe und jedes andere Lösungsmittel in Frange, wie beispielsweise Äthanol, Fuselöle, pflanslicbe oder tieriaohe Ole und dergl.The screen-inhibiting compounds according to the invention can thus be used find them as they are, emulsified in Waeeer * der godet in a liquid hydrocarbon. As a liquid hydrocarbon come light heating oil, gas oil, mobwares hoirs paraffinic Hydrocarbons and any other solvent in Frange, such as Ethanol, fusel oils, vegetable or animal oils and the like.
< Die Tafel 1 gibt dae aohaumheamende V rdgen der naob den Belxplelen 1 bis 7 bergestellten und weiterer Verbindungen nach der Erfindung socle die Zeitdauer ihrer Wirksamkeit wieder. Außerdem antbdlt die Tafel die Verbindungen J und t, die mit den gleichen Bestandteilen, aber unter Verwendung von Anteilen hergestellt sind, die außerhalb der duroh die Erfindung besogenen Grensen liegen. Wie festsustellon ist, lzaaon die eohaumhemmenden Eigeneohaften der orbaltenon Verbindungen bei Verlaaaen der angegebenon Gronsen stark naoh. <The table 1 gives the aohaumheamende claims of the naob den Belxplelen 1 to 7 and further compounds according to the invention as well as the duration their effectiveness again. In addition, the board shows the connections J and t, which are made with the same components but using proportions, which lie outside the limits of what the invention was concerned with. How festsustellon is, lzaaon the eohaum-inhibiting own accountability of the orbaltenon connections at Verlaaaen the statedon Gronsen strongly naoh.
Tafel 1 Schaumhemmende Eingesetzte Stoffe Form der Schaumhe Verbindung Saccharose Fattsäureester Propylenoxid Verwendung Kraft A 7% 50% 43% unverändert 0,059 10% in Wasser 0,50 10% in Kohlenwasserstoffen 0,60 B 10% 65% 25% unverändert 0,03 10% in Wasser 0,27 20% in Kehlenwasserstoffen 0,45 C 15% 60% 25% unverändert 0,14 10% in Wasser 0,51 10% in Kohlenwasserstoffen 0,59 D 23% 54% 23% unverändert 0,06 10% in Wasser 0,50 E 5% 70% 25% unverändert 0,08 F 13% 75% 12% 10% in Kohlenwasserstoffen 0,62 Äthylenexid G 5% 75% 20% unverändert 0,06 H 15% 60% 25% unverändert 0,09 Tafel 1 (Fortsetzung) Schaumbemmende Eingesetzte Stoffe Form der Schaumhemm Verbindung Saccharose Pettsäuresster Athylen-u. Verwendung Kraft Propylenexid I 10% 65% Ä.0. 10% unverändert 0,07 g P.0. 15% Heizöl unverändert 2,14 g nur 20% verminde Propylenexid J 45% 30% 25% unverändert 1,2 g nur 50% verminde K 35% 35% 30% unverändert 0,8 g nur 60% verminde Die sohaumhemmende Kraft und die Zoit ihrer Wirksamkeit wurde naoh der Methode bestimmt, die in dam Aufsatz von Dr. C. Fischer ; "Über ein einfaches Verfabron sur PrUfung von Entschäumern", verdffentlicht in der Zeitsohrift"Zuoker" vom 1. Märs 1953, S. 92 bis 94, beschrieben ist. Naoh dieser Methode wird die schaumhemmende Kraft durch das Gewicht don schaumhommenden Mittels in Gramm gemessen, dan einem Liter der Testflüssigkeit sugefUgt werden muß, um die Bildung von Schaum vollständig su verhindern. Die Zeitdauer der Wirksamkeit des schaumhemmenden Mittels ist die in Minuten ausgedrUckte Zeitspanne, nach der ein Schaum wieder su entstehen beginnt, weil das schaumhemmende Mittel nicht mehr wirksam ist.Table 1 Foam-inhibiting substances used Form of the foam compound Sucrose fatty acid ester propylene oxide Use Kraft A 7% 50% 43% unchanged 0.059 10% in water 0.50 10% in hydrocarbons 0.60 B 10% 65% 25% unchanged 0.03 10% in water 0.27 20% in hydrocarbons 0.45 C 15% 60% 25% unchanged 0.14 10% in water 0.51 10% in hydrocarbons 0.59 D 23% 54% 23% unchanged 0.06 10% in water 0.50 E 5% 70% 25% unchanged 0.08 F 13% 75% 12% 10% in hydrocarbons 0.62 Ethylenexid G 5% 75% 20% unchanged 0.06 H 15% 60% 25% unchanged 0.09 blackboard 1 (continued) Foam-inhibiting substances used Form of the foam-inhibiting compound Sucrose Pettsäuresster Athylen-u. Use Kraft Propylenexide I 10% 65% Ä.0. 10% unchanged 0.07 g P.0. 15% heating oil unchanged 2.14 g only 20% decrease propylene exide J 45% 30% 25% unchanged 1.2 g only 50% decrease K 35% 35% 30% unchanged 0.8 g only 60% decrease The squeeze-restraining power and the zoit of its effectiveness was determined according to the method described in the article by Dr. C. Fischer; "About a simple verification of defoamers ", published in the magazine" Zuoker " dated March 1, 1953, pp. 92 to 94. Naoh this method is the anti-foam Force measured by the weight of the foam absorbing agent in grams, then one Liters of the test liquid must be sugefUgt to complete the formation of foam su prevent. The length of time the anti-foaming agent is effective is that Period of time, expressed in minutes, after which foam begins to arise again, because the anti-foam agent is no longer effective.
Die Prüfung der schaumhemmenden Mittel fand bei einer Temperatur von 20°C statt. Als Testflüssigkeit wurde verdAnnte Melasse mit einem Zuckergehalt von 15° Brix und einem pH-Wert von 12, 5 benutzt.The test of foam inhibitors took place at a temperature of 20 ° C instead. Diluted molasses with a sugar content of 15 ° Brix and a pH of 12.5 are used.
In der folgenden Tafel 2 sind zua Vergleich die schaumhemmende Kraft und die Dauer der Wirksamkeit einiger handelsüblicher schaumhemmender Erzeugnisse dargestellt.The following table 2 shows the foam-inhibiting force for comparison and the duration of the effectiveness of some commercially available anti-foam products shown.
Tafel 2 rzeugnis Schaughemmende Kraft Wirksamkeitsdauer X1 1, 5 g 2 Minuten X2 0,1 g >60 Minuten @X3 0,12 g 8 Minuten X4 0,09 g 12 Minuten X5 0,16 g 5 Minuten X6 0, 13 g 4 Minuten Wie aus dlosem Vergleich hervorgeht, sind die erfindungsgemäßen achaumhemmenden Stoffe aehr aktiv. Die schaumhemmende Kraft ist eehr hoch und die Wirkungsdauer sehr lang, was su einem minimalen 9erbrauch führt. Darüberhinaus sind die erfindungsgemäßen Stoffe auob wegen des 'geringen Promises der eingesetsten Stoffe und der lelchten Durchführbarkeit do Verfahrens wirtschaftlich sehr orteilhaft. Table 2 product anti-foaming power effectiveness time X1 1.5 g 2 minutes X2 0.1 g> 60 minutes @ X3 0.12 g 8 minutes X4 0.09 g 12 minutes X5 0.16 g 5 minutes X6 0.13 g 4 minutes As can be seen from a comparison, those are according to the invention foam-inhibiting substances are very active. The foam-inhibiting power is very high and the Duration of action very long, which leads to minimal use. In addition, are the substances according to the invention also because of the 'low promise of the most used Substances and the low feasibility of the process are economically very beneficial.
Da die nach der Erfindung hergestellten Verbindungen absolut nicht-toxiach sind, sind aie besonders für die Nahrungamittelinduatrie geeignet. So wurden die Staffe mit Erfolg bei der Zuakerherstellung, inabesondere im Schwemmwaaser, bei der Aualaugung, der Kalkung und der Eindampfung, bei der Sacharat-Heratellung, der Destillation und der Hefeerzeugung eingesetzt. Since the compounds prepared according to the invention are absolutely non-toxic are also particularly suitable for the food industry. So they became Help me with success in the production of Zuaker, especially in the Schwemmwaaser the leaching, the liming and the evaporation, in the case of the Sacharat production, the Distillation and yeast production are used.
Claims (12)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
LU49607 | 1965-10-08 | ||
LU50954A LU50954A1 (en) | 1966-04-22 | 1966-04-22 | |
LU54905A LU54905A1 (en) | 1965-10-08 | 1967-11-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1668629A1 true DE1668629A1 (en) | 1971-01-28 |
Family
ID=27350601
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19671668629 Pending DE1668629A1 (en) | 1965-10-08 | 1967-11-28 | Process for the production of surface-active substances |
Country Status (5)
Country | Link |
---|---|
DE (1) | DE1668629A1 (en) |
ES (1) | ES347878A2 (en) |
FR (1) | FR93670E (en) |
LU (1) | LU54905A1 (en) |
NL (1) | NL6716356A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2462184A1 (en) * | 1979-07-31 | 1981-02-13 | Eurand France | Antifoaming silicone oil compsn. for washing powders - is oil mixed with absorbent cpd. and granules coated with cpd. |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5154856A (en) * | 1990-07-27 | 1992-10-13 | Henkel Kommanditgesellschaft Auf Aktien | Process for controlling aqueous media foam employing alkadiene ethers of sugars or alkyl glucosides |
US8877735B2 (en) * | 2004-08-31 | 2014-11-04 | The Procter & Gamble Company | Alkoxylated sucrose esters composition |
-
1967
- 1967-11-17 LU LU54905A patent/LU54905A1/xx unknown
- 1967-11-28 DE DE19671668629 patent/DE1668629A1/en active Pending
- 1967-12-01 ES ES347878A patent/ES347878A2/en not_active Expired
- 1967-12-01 NL NL6716356A patent/NL6716356A/xx unknown
- 1967-12-01 FR FR130733A patent/FR93670E/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2462184A1 (en) * | 1979-07-31 | 1981-02-13 | Eurand France | Antifoaming silicone oil compsn. for washing powders - is oil mixed with absorbent cpd. and granules coated with cpd. |
Also Published As
Publication number | Publication date |
---|---|
FR93670E (en) | 1969-05-02 |
LU54905A1 (en) | 1968-02-08 |
NL6716356A (en) | 1969-05-20 |
ES347878A2 (en) | 1969-02-16 |
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