DE854509C - Process for the production of surface-active mixed esters - Google Patents
Process for the production of surface-active mixed estersInfo
- Publication number
- DE854509C DE854509C DEB7250D DEB0007250D DE854509C DE 854509 C DE854509 C DE 854509C DE B7250 D DEB7250 D DE B7250D DE B0007250 D DEB0007250 D DE B0007250D DE 854509 C DE854509 C DE 854509C
- Authority
- DE
- Germany
- Prior art keywords
- production
- mixed esters
- water
- butadiene
- active mixed
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/20—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by addition of sulfurous acid or salts thereof to compounds having carbon-to-carbon multiple bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Description
Verfahren zur Herstellung von oberflächenwirksamen Mischestern Es wurde gefunden, daß man aus den hochsiedenden Alkoholgemischen, die bei der Herstellung von ßutadien durch Abspaltung von Wasser aus t, 3-Butylenglykol oder i, 4-Butylenglykol und Abdestillieren des Butadiens und niedrigsiedender Nebenprodukte zurückbleiben, oberflächenwirksame Stoffe erhält, die z. B. als Netz-, Emulgier- und Naschmittel angewandt werden können, wenn man diese Rückstände mit organischen Säuren verestert, die die Einführung wasserlöslich machender Gruppen gestatten, also z. B. ungesättigt sind oder Hydroxylgruppen enthalten, und in die erhaltenen Mischester wasserlöslich machende Gruppen einführt. Die wasserlöslich machenden Gruppen können z. B. durch Anlagerung von Natriumbisulfit an Doppelbindungen im Säurerest der Ester eingeführt "erden. Man kann aber auch in bekannter Weise an die Doppelbindungen Schwefelsäure anlagern. Ungesättigte Säuren, die sich zur Herstellung derartiger ungesättigter Ester eignen, sind beispielsweise Acrylsäure, Methacrylsäure, Maleinsäure, Citraconsäure, Itaconsäure und Aconitsäure. An Stelle der freien Säuren können auch ihre Anhydride verwendet werden. Man kann ferner, wenn die zur Veresterung angewandte Säure Hydroxylgruppen enthält, diese mit mehrbasischen Mineralsäuren verestern oder in sie durch Behandeln mit Alkylenoxyden, z. B. Äthylenoxyd, Polyalkylätherreste einführen. Schließlich können auch zur Veresterung Halogencarbonsäuren herangezogen werden, deren Halogenatome man dann z. B. mit Natriumsulfit gegen den Rest-S O3 Na austauschen kann. Beispiel 185 Teile des durch Veresterung von 98 Teilen Maleinsäureanhydrid mit 35o Teilen eines bei der Herstellung von Butadien aus i, 4-Butylenglykol durch Abspaltung von Wasser und Abdestillieren des Butadiens erhaltenen Alkoholgemisches vom ungefähren Molekulargewicht 16o erhaltenen neutralen Mischesters werden in eine Lösung von 49 Teilen Natriumbisulfit in 12o Teilen Wasser eingetragen und etwa 5 Stunden lang bei 8o bis 9o° gerührt. Dabei geht der Mischester völlig in Lösung, und man erhält eine klare, stark schäumende Lösung von hervorragendem Netzvermögen. Beim Abtreiben des Wassers unter vermindertem Druck erhält man eine schwachgelbe wachsartige Masse.Process for the production of surface active mixed esters Es it was found that the high-boiling alcohol mixtures used in the manufacture of ßutadiene by splitting off water from t, 3-butylene glycol or i, 4-butylene glycol and distilling off the butadiene and low-boiling by-products remain, surface-active substances that z. B. as a wetting agent, emulsifier and snack agent can be used if these residues are esterified with organic acids, which allow the introduction of water-solubilizing groups, e.g. B. unsaturated are or contain hydroxyl groups, and water-soluble in the mixed esters obtained introducing making groups. The water-solubilizing groups can e.g. B. by Addition of sodium bisulfite to double bonds in the acid residue of the ester introduced ". But you can also use sulfuric acid to connect to the double bonds in a known manner attach. Unsaturated acids that are used to produce such unsaturated Suitable esters are, for example, acrylic acid, methacrylic acid, maleic acid, citraconic acid, Itaconic acid and aconitic acid. Instead of the free acids, their anhydrides can also be used be used. Furthermore, if the acid used for the esterification is hydroxyl groups contains, esterifying them with polybasic mineral acids or in them by treating with Alkylene oxides, e.g. B. Ethylene oxide, introduce polyalkyl ether residues. Finally you can Halocarboxylic acids, their halogen atoms, are also used for the esterification one then z. B. can exchange with sodium sulfite for the remaining S O3 Na. example 185 parts of maleic anhydride obtained by esterification of 98 parts with 35o parts one in the production of butadiene from i, 4-butylene glycol by splitting off Water and distilling off the butadiene obtained alcohol mixture from the approximate Molecular weight 16o obtained neutral mixed ester are in a solution of 49 parts of sodium bisulfite in 12o parts of water and added for about 5 hours stirred at 8o to 9o °. The mixed ester goes completely into solution and is obtained a clear, strong foaming solution with excellent wetting properties. When aborting of the water under reduced pressure, a pale yellow, waxy mass is obtained.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB7250D DE854509C (en) | 1944-08-05 | 1944-08-05 | Process for the production of surface-active mixed esters |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB7250D DE854509C (en) | 1944-08-05 | 1944-08-05 | Process for the production of surface-active mixed esters |
Publications (1)
Publication Number | Publication Date |
---|---|
DE854509C true DE854509C (en) | 1952-11-04 |
Family
ID=6955236
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEB7250D Expired DE854509C (en) | 1944-08-05 | 1944-08-05 | Process for the production of surface-active mixed esters |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE854509C (en) |
-
1944
- 1944-08-05 DE DEB7250D patent/DE854509C/en not_active Expired
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