DE1246252B - Process for the manufacture of new surfactants - Google Patents
Process for the manufacture of new surfactantsInfo
- Publication number
- DE1246252B DE1246252B DEL41823A DEL0041823A DE1246252B DE 1246252 B DE1246252 B DE 1246252B DE L41823 A DEL41823 A DE L41823A DE L0041823 A DEL0041823 A DE L0041823A DE 1246252 B DE1246252 B DE 1246252B
- Authority
- DE
- Germany
- Prior art keywords
- transesterification
- ethylene oxide
- weight
- fatty acid
- manufacture
- 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
-
- 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
-
- 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
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Testing Electric Properties And Detecting Electric Faults (AREA)
- Financial Or Insurance-Related Operations Such As Payment And Settlement (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Int. CL:Int. CL:
C08gC08g
Deutsche Kl.. 39 c-30German class. 39 c-30
Nummer: 1 246 252Number: 1 246 252
Aktenzeichen: L 41823 IV d/39 cFile number: L 41823 IV d / 39 c
Anmeldetag: 25. April 1962 Filing date: April 25, 1962
Auslegetag: 3. August 1967Opened on August 3, 1967
Gegenstand der Erfindung ist ein Verfahren zur Herstellung neuer_ oberflächenaktiver Mittel, durch Umsetzung von Äthylenoxyd mit Hydroxylgruppen enthaltenden Verbindungen in Gegenwart eines alkalischen Katalysators, das dadurch gekennzeichnet ist, daß man 1 Gewichtsteil eines Umesterungsgemisches, das durch Umesterung von natürlichen oder synthetischen Fettsäuretriglyceriden mit Rohrzucker in einem Lösungsmittel in Gegenwart eines alkalischen Katalysators hergestellt worden ist, mit mindestens 1 Gewichtsteil Äthylenoxyd in einem Autoklav auf eine Temperatur von 70 bis 1300C in Gegenwart einer kleinen Menge eines Glycerids erhitzt.The invention relates to a process for the production of new surface-active agents by reacting ethylene oxide with compounds containing hydroxyl groups in the presence of an alkaline catalyst, which is characterized in that 1 part by weight of a transesterification mixture obtained by transesterification of natural or synthetic fatty acid triglycerides with cane sugar in one Solvent has been prepared in the presence of an alkaline catalyst, heated with at least 1 part by weight of ethylene oxide in an autoclave to a temperature of 70 to 130 0 C in the presence of a small amount of a glyceride.
Das erfindungsgemäß verwendete Umesterungsgemisch wird in bekannter Weise durch Umesterung von natürlichen Fettsäuretriglyceriden, wie z. B. Specköl, Talg, Kokosnußöl, Palmöl oder Palmkernöl oder synthetischen Fettsäuretriglyceriden in einem Lösungsmittel mit Rohrzucker in Gegenwart eines alkalischen Katalysators, wie z. B. Alkalimetall hydroxyden und -carbonaten, hergestellt. Während der Reaktion werden ein oder mehrere Säurereste der Glyceride abgespalten und reagieren unter Veresterung mit einer oder mehreren alkoholischen Hydroxylgruppen des Rohrzuckers. Auf diese Weise erzielt man Umesterungsgemische, die je nach der bei der Umesterung anwesenden Menge Rohrzucker verschiedene Mengen an gebundenem Zucker enthalten. Die Umesterungsgemische enthalten verschiedene Mengenanteile von Monoestern von Rohrzucker mit den verschiedenen Fettsäuren des Ausgangsglycerids, den Mono-, oder Diglyceriden oder ihren Gemischen (je nach der aus jedem Mol des Ausgangsglycerids entfernten Menge von Fettsäurerückständen) und im allgemeinen kleine Mengen von nichtumgesetztem Triglycerid. Die erfindungsgemäß verwendeten Umesterungsgemische sind im allgemeinen wasserunlösliche Produkte, die jedoch leicht dispergierbar sind; sie besitzen lyophile Eigenschaften und sind infolgedessen keine besonders guten Emulgiermittel, sondern weisen vielmehr nur geringe Benetzungs- und Reinigungseigenschaften auf.The transesterification mixture used according to the invention is produced in a known manner by transesterification of natural fatty acid triglycerides, such as. B. Bacon oil, tallow, coconut oil, palm oil or palm kernel oil or synthetic fatty acid triglycerides in a solvent with cane sugar in the presence of a alkaline catalyst, such as. B. alkali metal hydroxides and carbonates produced. While During the reaction, one or more acid residues of the glycerides are split off and react with esterification with one or more alcoholic hydroxyl groups of cane sugar. In this way transesterification mixtures are obtained which, depending on the amount of cane sugar present during the transesterification contain different amounts of bound sugar. The transesterification mixtures contain various Quantities of monoesters of cane sugar with the various fatty acids of the starting glyceride, the mono- or diglycerides or their mixtures (depending on the one from each mole of the starting glyceride removed amount of fatty acid residues) and generally small amounts of unreacted Triglyceride. The transesterification mixtures used according to the invention are in general water-insoluble products but which are easily dispersible; they have lyophilic properties and are consequently no particularly good emulsifying agents, but rather only have low wetting and wetting properties Cleaning properties.
Der Trübungspunkt von Polyoxyäthylen-Produkten ist eine besonders wichtige Eigenschaft, wenn sie als
Reinigungs- und Dispergiermittel verwendet werden. Zum Beispiel wird das Färben synthetischer Textilfasern,
die in der Regel bei einer Temperatur über 1000C gefärbt werden, in Anwesenheit nichtionischer
Stoffe, wie z. B. Polyoxyäthylen-Derivaten, durchgeführt. Die bisher bekannten Polyoxyäthylen-Produkte
haben alle die Eigenschaften, bei einer Tem-Verfahren zur Herstellung neuer
oberflächenaktiver MittelThe cloud point of polyoxyethylene products is a particularly important property when used as cleaning and dispersing agents. For example, the dyeing of synthetic textile fibers, which are usually dyed at a temperature above 100 0 C, in the presence of non-ionic substances, such as. B. polyoxyethylene derivatives performed. The previously known polyoxyethylene products all have the properties at a Tem process for the production of new
surfactants
Anmelder:Applicant:
Ledoga S. p. A., Mailand (Italien)Ledoga S. p. A., Milan (Italy)
Vertreter:Representative:
Dr. W. Beil, A. Hoeppener und Dr. H. J. Wolff,Dr. W. Beil, A. Hoeppener and Dr. H. J. Wolff,
Rechtsanwälte,Lawyers,
Frankfurt/M.-Höchst, Adelonstr. 58Frankfurt / M.-Höchst, Adelonstr. 58
Als Erfinder benannt:Named as inventor:
Luciano Nobile, Mailand (Italien)Luciano Nobile, Milan (Italy)
Beanspruchte Priorität:Claimed priority:
Italien vom 29. April 1961 (8060)Italy April 29, 1961 (8060)
peratur unter 1000C (Trübungspunkt) unslöslich zu werden. Aus diesem Grund findet bei den erforderlichen Temperaturbedingungen eine Trübung der gefärbten Faser unter anschließendem Stumpfwerden statt.temperature below 100 0 C (cloud point) to become insoluble. For this reason, under the required temperature conditions, the dyed fiber becomes cloudy with subsequent dulling.
Der Trübungspunkt der erfindungsgemäß hergestellten Produkte liegt dagegen über 1000C. Seine Höhe hängt von der Menge des mit dem Umesterungsgemisch vereinigten Äthylenoxyds ab.The cloud point of the products prepared according to the invention, on the other hand, is above 100 ° C. Its level depends on the amount of ethylene oxide combined with the transesterification mixture.
In den folgenden Beispielen wird die zugeführte Menge Äthylenoxyd in Beziehung zu dem Gewicht des Umesterungsgemisches gesetzt, da es infolge der komplexen Beschaffenheit des Umesterungsgemisches nicht möglich ist, die Mengenverhältnisse stöchiometrisch zu berechnen.In the following examples, the amount of ethylene oxide added is related to the weight of the transesterification mixture, as it is due to the complex nature of the transesterification mixture it is not possible to calculate the proportions stoichiometrically.
Die folgenden Beispiele dienen der Erläuterung der Erfindung.The following examples serve to illustrate the invention.
In einen Autoklav für die Oxyäthylierung werden kg eines Umesterungsgemisches, das unter Verwendung von Speck als Fettsäuretriglycerid erhalten wurde, mit einem Gehalt von 25°/0 gebundenem Zucker, 5 kg raffinierter Talg und 0,150 kg Natriumhydroxyd eingeführt. Das Ganze wird auf 9O0C erhitzt, und während 4 Stunden werden 300 kg Äthylenoxyd eingeführt.In an autoclave for the oxyethylation with a content of 25 ° / 0 bound sugar 5 kg of refined talc and 0.150 kg of sodium hydroxide are introduced kg of a transesterification mixture which has been obtained by using fat as a fatty acid triglyceride. The whole is heated at 9O 0 C for 4 hours and 300 kg of ethylene oxide are introduced.
709 619/705709 619/705
Die Temperatur muß so reguliert werden, daß nach Beendigung der Reaktion eine Höchsttemperatur von 12O0C erreicht ist.The temperature must be regulated so that after completion of the reaction, maximum temperature is reached 12O 0 C.
Das Kondensationsprodukt ist eine hellbraune ölige Flüssigkeit, die in Wasser vollständig und schnell löslich ist und einen Trübungspunkt von 1000C (in 1 °/oiger wäßriger Lösung) hat.The condensation product is a light brown oily liquid which is completely and rapidly soluble in water and has a cloud point of 100 0 C (in 1 ° / o aqueous solution).
Der Versuch vom Beispiel 1 wird wiederholt, wobei ein Umesterungsgemisch, das unter Verwendung von Kokosnußöl als Fettsäuretriglycerid erhalten wurde, mit einem Rohrzuckergehalt von 30°/0 verwendet wird. -Zu 95 kg des Umesterungsgemisches werden 5 kg Palmkernöl und 0,150 kg Kaliumhydroxyd zugesetzt. Die Reaktion wird bei 800C begonnen. Die Äthylenoxydmenge verhält sich zum Gesamtgewicht der weiteren Ausgangsstoffe wie 3:1. Die Endtemperatur ist 12O0C. Die Kondensation dauert insgesamt 5 Stunden.The experiment of Example 1 wherein a transesterification mixture which has been obtained by using coconut oil fatty acid triglyceride as is used with a cane sugar content of 30 ° / 0 is repeated. 5 kg of palm kernel oil and 0.150 kg of potassium hydroxide are added to 95 kg of the transesterification mixture. The reaction is started at 80 0 C. The ratio of the amount of ethylene oxide to the total weight of the other starting materials is 3: 1. The final temperature is 12O 0 C. The condensation takes total of 5 hours.
Das erhaltene Produkt (400 kg) besteht aus einer blaßgelben öligen Flüssigkeit, die in Wasser in Form einer stark schäumenden Lösung vollständig löslich ist und einen Trübungspunkt bei 1020C (l%ige Lösung in Wasser) aufweist.The product obtained (400 kg) consists of a pale yellow oily liquid which is completely soluble in water in the form of a strongly foaming solution and has a cloud point of 102 ° C. (1% solution in water).
Der Versuch vom Beispiel 1 wird wiederholt, jedoch wird das Äthylenoxyd im Verhältnis von 9 :1, bezogen auf das Gesamtgewicht der weiteren Ausgangsstoffe, verwendet. Die Kondensation dauert insgesamt 7 Stunden. Als Endprodukt erhielt man eine weiche, wachsförmige, elfenbeinfarbene Masse, die in Wasser vollständig löslich ist und einen Trübungspunkt vonThe experiment from Example 1 is repeated, but the ethylene oxide is based in a ratio of 9: 1 based on the total weight of the other starting materials. The condensation takes a total of 7 hours. The end product was a soft, waxy, ivory-colored mass that was completely immersed in water is soluble and has a cloud point of
ίο 1100C (l°/oige Lösung in Salzwasser) hat.has ίο 110 0 C (l ° / o solution in salt water).
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT806061 | 1961-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1246252B true DE1246252B (en) | 1967-08-03 |
Family
ID=11125704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEL41823A Pending DE1246252B (en) | 1961-04-29 | 1962-04-25 | Process for the manufacture of new surfactants |
Country Status (3)
| Country | Link |
|---|---|
| AT (1) | AT246174B (en) |
| BE (1) | BE616658A (en) |
| DE (1) | DE1246252B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2701194A1 (en) * | 1993-02-08 | 1994-08-12 | Rhone Poulenc Chimie | Plant-protection compositions containing ethoxylated sucroglycerides |
| WO2006026638A1 (en) | 2004-08-31 | 2006-03-09 | The Procter & Gamble Company | Alkoxylated sucrose esters composition |
| WO2006026639A1 (en) * | 2004-08-31 | 2006-03-09 | The Procter & Gamble Company | Improved synhesis of alkoxylated sucrose esters |
-
1962
- 1962-04-19 BE BE616658A patent/BE616658A/en unknown
- 1962-04-25 DE DEL41823A patent/DE1246252B/en active Pending
- 1962-04-27 AT AT346962A patent/AT246174B/en active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2701194A1 (en) * | 1993-02-08 | 1994-08-12 | Rhone Poulenc Chimie | Plant-protection compositions containing ethoxylated sucroglycerides |
| WO2006026638A1 (en) | 2004-08-31 | 2006-03-09 | The Procter & Gamble Company | Alkoxylated sucrose esters composition |
| WO2006026639A1 (en) * | 2004-08-31 | 2006-03-09 | The Procter & Gamble Company | Improved synhesis of alkoxylated sucrose esters |
Also Published As
| Publication number | Publication date |
|---|---|
| BE616658A (en) | 1962-08-16 |
| AT246174B (en) | 1966-04-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE694178C (en) | Process for the preparation of condensation products which are soluble or easily dispersible in water | |
| DE1288580B (en) | Process for the production of surface-active substances from alcohols, fatty acid esters and alkylene oxides | |
| DE4122530A1 (en) | METHOD FOR PRODUCING FAT SAUCE LIQUID CYLINDERS | |
| DE857948C (en) | Process for the production of neutral esters of carbonic acid | |
| DE1593216C3 (en) | Non-ionic surface-active compounds and processes for their preparation | |
| DE2129425B2 (en) | Process for the production of fatty acid ethanol amides | |
| DE1246252B (en) | Process for the manufacture of new surfactants | |
| DE2327729C3 (en) | ||
| DE69816944T2 (en) | Process for the preparation of an aliphatic amine derivative | |
| DE2327729B2 (en) | TRANSFER CATALYST | |
| DE572867C (en) | Process for the conversion of natural and artificial wax esters or wax mixtures into fatty acids | |
| DE2311344A1 (en) | Process for the production of cold-resistant, liquid fatty acid esters | |
| DE560916C (en) | Soap-like products | |
| DE551403C (en) | Process for the production of emulsions | |
| DE2210347A1 (en) | Bactericidal substance | |
| DE1443016A1 (en) | Method for modifying a polyether polyol | |
| DE565057C (en) | Emulsion wax | |
| DE593709C (en) | Process for the production of sulfonation products of the alcohols corresponding to the higher fatty acids, obtainable by reducing their alkyl esters | |
| DE1018427B (en) | Process for the preparation of esters of 4-chloro-o-tolyloxyacetic acid | |
| AT139102B (en) | Process for melting textile materials. | |
| DE604255C (en) | Process for the production of capillary-active sulfonation products from uncleaved waxes | |
| DE539265C (en) | Process to increase the spinnability of wool | |
| DE630467C (en) | Process for producing a low-water hard emulsion | |
| DE865904C (en) | Process for the production of compounds containing sulfur | |
| DE1125657B (en) | Process for the production of hydraulic fluids |