DE639330C - Process for the preparation of capillary-active aliphatic oxyamines - Google Patents
Process for the preparation of capillary-active aliphatic oxyaminesInfo
- Publication number
- DE639330C DE639330C DEB166410D DEB0166410D DE639330C DE 639330 C DE639330 C DE 639330C DE B166410 D DEB166410 D DE B166410D DE B0166410 D DEB0166410 D DE B0166410D DE 639330 C DE639330 C DE 639330C
- Authority
- DE
- Germany
- Prior art keywords
- aliphatic
- oxyamines
- capillary
- preparation
- active aliphatic
- 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
- 125000001931 aliphatic group Chemical group 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 150000003944 halohydrins Chemical class 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000009825 accumulation Methods 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- -1 aliphatic amines Chemical class 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000003945 chlorohydrins Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- YITMLDIGEJSENC-HWKANZROSA-N (e)-hexadec-2-ene Chemical compound CCCCCCCCCCCCC\C=C\C YITMLDIGEJSENC-HWKANZROSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- YITMLDIGEJSENC-UHFFFAOYSA-N Hexadecen Natural products CCCCCCCCCCCCCC=CC YITMLDIGEJSENC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
-
- 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
- C09K23/16—Amines or polyamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von kapillaraktiven aliphatischen Oxyaminen Es wurde gefunden, daß man durch Einwirkung des Ammotliaks oder der niedrigsten aliphatischen Amine auf hochmolekulare aliphatische a-Halogenhydrine, die durch Anlagerung von unterhalogeniger Säure an Olefine mit mindestens 12 Kohlenstoffatomen gewonnen werden, a-Oxyamine in glatter Reaktion und mit sehr guter Ausbeute erhält, die in Form ihrer Salze mit anorganischen oder organischen Säuren außerordentlich leicht in Wasser löslich sind und -ein vorzügliches Schaum- und Emulgierungsvermögen besitzen.Process for the preparation of capillary-active aliphatic oxyamines It has been found that by the action of the Ammotliaks or the lowest aliphatic amines to high molecular weight aliphatic a-halohydrins, which by Addition of hypohalous acids to olefins with at least 12 carbon atoms obtained, a-Oxyamine is obtained in a smooth reaction and with a very good yield, which, in the form of their salts with inorganic or organic acids, are extraordinary are easily soluble in water and have excellent foaming and emulsifying properties own.
Das Verfahren kann beispielsweise folgendermaßen ausgeführt werden. -Beispiel i Ein Gemisch der homologen Olefine von Dodecen bis Eikosen wird durch Behandlung mit der erforderlichen Menge frisch bereiteter, etwa r,5°/oiger Lösung von ünterchloriger Säure unter Kühlen und Rühren in das Gemisch der homologen Chlorhydrine übergeführt. Dieses Gemisch wird mit einem mäßigen Überschuß konzentrierter Diäthylaminlösung und einer Spur Kupfersulfat 16 Stunden auf 22o bis 23o° erhitzt. Aus dem mit Lauge versetzten Umsetzungsgemisch scheiden sich die Diäthylaminofettalkohole als 01 ab. Man wäscht mit Wasser und behandelt dann mit Mineralsäure, wobei die etwa nicht umgesetzten Chlorhydrine ungelöst bleiben. Aus der wässerigen Lösung fällt Lauge die Diäthylaminofettalkohole praktisch rein (z. B. Stickstoffgehalt ber. 447°/0 gef- 438°/o). Die Verbindungen sind gelb bis bräunlich gefärbte klare Öle, die sich in organischen Lösungsmitteln lösen. Während sie in reinem Wasser unlöslich sind, lösen sie sich nach Zufügen von Säure spielend leicht und bilden stark schäumende Lösungen von großer Emulgierungsfähigkeit. Beispiel 2 Hexadecylchlorhydrin, das ähnlich, wie in Beispiel r beschrieben, aus r, 2-Hexadecen und unterchloriger Säure gewonnen wurde, wird mit einem Überschuß von Ammoniale im geschlossenen Gefäß 12 Stunden auf 225 bis 25o° erhitzt. Nach dem Erkalten versetzt man das Umsetzungsgemisch mit Alkalilauge, wäscht die abgeschiedene Base mit Wasser und behandelt sie dann mit Mineralsäure zwecks Abtrennung des etwa nicht umgesetzten Chlorhydrins. Aus der wässerigen Lösung kann das a-Oxyhexadecylamin durch Mineralsäure in praktisch reinem Zustande ausgefällt `werden. Die Eigenschaften dieser Verbindung sind ähnlich wie die der gemäß Beispiel r erhaltenen.The method can be carried out, for example, as follows. Example i A mixture of the homologous olefins from dodecene to eicoses is converted into the mixture of the homologous chlorohydrins by treatment with the required amount of freshly prepared, about 5% solution of hypochlorous acid with cooling and stirring. This mixture is heated to 22o to 23o ° for 16 hours with a moderate excess of concentrated diethylamine solution and a trace of copper sulfate. The diethylamino fatty alcohols separate out as 01 from the reaction mixture to which lye has been added. It is washed with water and then treated with mineral acid, any unreacted chlorohydrins remaining undissolved. Lye and the diethylamino fatty alcohols fall practically pure from the aqueous solution (e.g. nitrogen content above. 447% and 438%). The compounds are yellow to brownish colored clear oils that dissolve in organic solvents. While they are insoluble in pure water, they dissolve easily after adding acid and form strong foaming solutions with great emulsifying properties. EXAMPLE 2 Hexadecylchlorohydrin, which was obtained from r, 2-hexadecene and hypochlorous acid in a manner similar to that described in Example r, is heated to 225 to 250 ° for 12 hours with an excess of ammonia in a closed vessel. After cooling, alkali lye is added to the reaction mixture, the base which has separated out is washed with water and then treated with mineral acid to remove any unreacted chlorohydrin. The a-oxyhexadecylamine can be precipitated in a practically pure state from the aqueous solution by means of mineral acid. The properties of this compound are similar to those obtained in Example r.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB166410D DE639330C (en) | 1933-09-02 | 1933-09-02 | Process for the preparation of capillary-active aliphatic oxyamines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB166410D DE639330C (en) | 1933-09-02 | 1933-09-02 | Process for the preparation of capillary-active aliphatic oxyamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE639330C true DE639330C (en) | 1936-12-03 |
Family
ID=7005659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB166410D Expired DE639330C (en) | 1933-09-02 | 1933-09-02 | Process for the preparation of capillary-active aliphatic oxyamines |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE639330C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2445892A (en) * | 1946-02-05 | 1948-07-27 | Us Agriculture | Amino fatty derivatives |
-
1933
- 1933-09-02 DE DEB166410D patent/DE639330C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2445892A (en) * | 1946-02-05 | 1948-07-27 | Us Agriculture | Amino fatty derivatives |
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