DE679711C - Process for the production of ethersic acids - Google Patents
Process for the production of ethersic acidsInfo
- Publication number
- DE679711C DE679711C DEB181270D DEB0181270D DE679711C DE 679711 C DE679711 C DE 679711C DE B181270 D DEB181270 D DE B181270D DE B0181270 D DEB0181270 D DE B0181270D DE 679711 C DE679711 C DE 679711C
- Authority
- DE
- Germany
- Prior art keywords
- acids
- production
- ethersic
- homologues
- triethanolamine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000002253 acid Substances 0.000 title claims description 10
- 150000007513 acids Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- -1 alkali metal salts Chemical class 0.000 claims 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 235000011941 Tilia x europaea Nutrition 0.000 description 4
- 239000004571 lime Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001447 alkali salts Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000008233 hard water Substances 0.000 description 2
- 150000003112 potassium compounds Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BIHLHMHULOMJLI-UHFFFAOYSA-N 3-[bis(2-hydroxyethyl)amino]propan-1-ol Chemical compound OCCCN(CCO)CCO BIHLHMHULOMJLI-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- KPFSGNRRZMYZPH-UHFFFAOYSA-M potassium;2-chloroacetate Chemical compound [K+].[O-]C(=O)CCl KPFSGNRRZMYZPH-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/125—Saturated compounds having only one carboxyl group and containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
- C09K23/44—Ether carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Description
Verfahren zur Herstellung von Äthersäuren Es wurde gefunden, daß man die bekannten Alkaliverbindungen des Triäthanolamins und die auf gleiche Weise erhältlichen Alkaliverbindungen seiner Homologen, wie z. B. des Diäthanolpropanolamins oder des Diäthanolbutanolamins, durch Umsetzung mit der äquivalenten Menge oder einem Mehrfachen davon an Monohalogenessigsäure oder Monohalogenpropionsäure bzw. den Alkalisalzen dieser Säuren in Äthersäuren der allgemeinen Formel oder deren Homologen überführen kann. In der Formel ist n = r, 2 oder 3, in =:2, i oder o und die Summe m + n = 3. Die Säuren entstehen zunächst in Form ihrer Alkalisalze und können durch Ansäuern und Abtrennen des entstandenen Alkalihalogenides als solche gewonnen werden. Sie zeichnen sich durch die Fähigkeit aus, Kalkseifen in Wasser in feine Dispersion zu bringen und dadurch unschädlich zu machen, und sind daher besonders als Zusätze zu Wasch-, Netz-, Dispergier- und Durchdringungsmitteln, die in hartem Wasser oder in Chlorkalkbleichbädern verwendet werden sollen, geeignet.Process for the preparation of etheric acids It has been found that the known alkali compounds of triethanolamine and the alkali compounds of its homologues obtainable in the same way, such as, for. B. of diethanolpropanolamine or diethanolbutanolamine, by reaction with the equivalent amount or a multiple thereof of monohaloacetic acid or monohalopropionic acid or the alkali salts of these acids in ether acids of the general formula or can convert their homologues. In the formula n = r, 2 or 3, in =: 2, i or o and the sum m + n = 3. The acids are initially formed in the form of their alkali salts and can be obtained as such by acidifying and separating off the alkali halide formed . They are characterized by the ability to bring lime soaps into fine dispersion in water and thereby render them harmless, and are therefore particularly suitable as additives to detergents, wetting agents, dispersants and penetrants that are to be used in hard water or in chlorinated lime bleach baths , suitable.
Die Umsetzung zwischen den Alkoholaten der Alkylolamine und den halogenessigsauren oder halogenpropionsauren Salzen kann zweckmäßig in einem organischen Lösungsmittel, wie Alkohol, Benzol, Toluol, Äther oder Tetrachlorkohlenstoff, unter Erwärmen am Rückflußkühler oder im Autoklaven vorgenommen werden. Die anorganischen Salze scheiden sich hierbei ab. Aus dem Filtrat können die Salze der Äthersäuren gegebenenfalls nach Einengen gewonnen werden. Beispiel Triäthanolamin wird mit 5o°loiger wäßriger Kalilauge versetzt, wodurch sich die Kaliumverbindung des Triäthanolamins abscheidet, die durch Abschleudern und Trocknen im Vakuum als Trockenprodukt erhaltenwird. 26 Gewichtsteile der Kaliumverbindung des Triäthanolamins und 4o Gewichtsteile monochloressigsaures Kalium werden, in zoo Gewichtsteilen Alkohol suspendiert und mehrere Stunden unter Rückfluß gekocht. Das ausgeschiedene Kaliuinchlorid wird abfiltriext und hierauf das Filtrat eingeengt, bis sich das Alkalisalz der entstandenen Äthersäure ausscheidet. Das Produkt ist für technische Zwecke genügend rein. Nötigenfalls kann es durch Umkristallisieren in bekannter Weise noch weitergereinigt werden.The reaction between the alcoholates of the alkylolamines and the haloacetic or halopropionic salts can expediently be carried out in an organic solvent, such as alcohol, benzene, toluene, ether or carbon tetrachloride, with warming in a reflux condenser or in an autoclave. The inorganic salts separate out here. The salts of the ether acids can optionally be obtained from the filtrate after concentration. Example Triethanolamine is mixed with 50 ° aqueous potassium hydroxide solution, whereby the potassium compound of triethanolamine separates, which is obtained as a dry product by centrifuging and drying in vacuo. 26 parts by weight of the potassium compound of triethanolamine and 40 parts by weight of potassium monochloroacetate are suspended in zoo parts by weight of alcohol and refluxed for several hours. The precipitated potassium chloride is filtered off and the filtrate is then concentrated until the alkali salt of the ether acid formed separates out. The product is sufficiently pure for technical purposes. If necessary, it can be further purified in a known manner by recrystallization.
Die gemäß der Erfindung erhaltenen Äthersäuren können beispielsweise als Zusatz zu Seifen und seifenähnlichen Stoffen aller Art sowie auch zu kalkempfindlichen Farbstoffen zwecks Erhöhung der Beständigkeit gegen hartes Wasser und sonstige kalk- oder magne-`siumsalzhaltige Lösungen verwedet werden.The ether acids obtained according to the invention can, for example as an additive to soaps and soap-like substances of all kinds as well as to lime-sensitive substances Dyes to increase the resistance to hard water and other lime or solutions containing magnesium salts can be used.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB181270D DE679711C (en) | 1937-12-28 | 1937-12-28 | Process for the production of ethersic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB181270D DE679711C (en) | 1937-12-28 | 1937-12-28 | Process for the production of ethersic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE679711C true DE679711C (en) | 1939-08-15 |
Family
ID=7009040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB181270D Expired DE679711C (en) | 1937-12-28 | 1937-12-28 | Process for the production of ethersic acids |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE679711C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2623900A (en) * | 1948-09-01 | 1952-12-30 | Sandoz Ag | Method for the preparation of polyether acetic acids |
-
1937
- 1937-12-28 DE DEB181270D patent/DE679711C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2623900A (en) * | 1948-09-01 | 1952-12-30 | Sandoz Ag | Method for the preparation of polyether acetic acids |
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