DE559500C - Process for the preparation of quaternary ammonium salts - Google Patents
Process for the preparation of quaternary ammonium saltsInfo
- Publication number
- DE559500C DE559500C DEG73690D DEG0073690D DE559500C DE 559500 C DE559500 C DE 559500C DE G73690 D DEG73690 D DE G73690D DE G0073690 D DEG0073690 D DE G0073690D DE 559500 C DE559500 C DE 559500C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- quaternary ammonium
- mixed
- ammonium salts
- water
- 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
- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 150000004985 diamines Chemical class 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- -1 oleyl diethyl ethylenediamine Chemical compound 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 9
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000005187 foaming Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- CJKRXEBLWJVYJD-UHFFFAOYSA-N N,N'-diethylethylenediamine Chemical compound CCNCCNCC CJKRXEBLWJVYJD-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- JNFLSJUGIONDMJ-UHFFFAOYSA-N 2-n,2-n-diethylpropane-1,2-diamine Chemical compound CCN(CC)C(C)CN JNFLSJUGIONDMJ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VFXMWBGLBNFTSY-UHFFFAOYSA-N n-benzyl-n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCNCC1=CC=CC=C1 VFXMWBGLBNFTSY-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
- VKJCJJYNVIYVQR-UHFFFAOYSA-N 2-(3-bromopropyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCBr)C(=O)C2=C1 VKJCJJYNVIYVQR-UHFFFAOYSA-N 0.000 description 1
- VSLZBNITTUEHIY-UHFFFAOYSA-N 4-[3-(diethylamino)propyl]isoindole-1,3-dione Chemical compound C(C)N(CCCC1=C2C(C(=O)NC2=O)=CC=C1)CC VSLZBNITTUEHIY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- ZALQXZOEIDOLKZ-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)C1=C(N(C)C)C=CC(=C1)N Chemical compound C(CCCCCCCCCCCCCCCCC)C1=C(N(C)C)C=CC(=C1)N ZALQXZOEIDOLKZ-UHFFFAOYSA-N 0.000 description 1
- UWQNMIQOGXRLET-UHFFFAOYSA-N CCN(CC)CCN(C(OC)=O)C(OC)=O Chemical compound CCN(CC)CCN(C(OC)=O)C(OC)=O UWQNMIQOGXRLET-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012435 aralkylating agent Substances 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- AYTWRFAUDPVQAP-UHFFFAOYSA-N n,n'-diethyl-n'-octadecylethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCCCN(CC)CCNCC AYTWRFAUDPVQAP-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
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- 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
- C09K23/18—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/06—Hydrogenosulfates
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/08—Dialkylsulfates; Substituted dialkylsulfates
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung quaternärer Ammoniumsalze Es wurde gefunden, daß man einseitig acylierte Diamine durch Behandlung mit Alkylierungs- oder Aralkylierungsmitteln in quaternäre Ammoniumsalze überführen kann, wobei die Reaktion z. B. bei Verwendung von Oleyldiäthyläthylendiamin und Dimethylsulfat nach folgender Gleichung verläuft: Die neuen Verbindungen besitzen in wäßriger Lösung ausgesprochenen Seifencharakter, den sie auch nach Zusatz eines alkalischen Mittels, wie z. B. Alkali oder Soda, oder einer Säure unverändert beibehalten. Demgegenüber werden die einseitig acylierten Diamine in alkalischer, die gewöhnlichen Fettsäureseifen aber in saurer Lösung ausgefällt. Die neuen Verbindungen vereinigen somit die Vorzüge dieser beiden Klassen. Ihr Anwendungsgebiet ist sehr ausgedehnt; so können sie z. B. als Wasch- und Benetzungsmittel oder als Zusatz zu Farbbädern bei beliebiger alkalischer, saurer oder neutraler Reaktion Verwendung finden.Process for the preparation of quaternary ammonium salts It has been found that one-sided acylated diamines can be converted into quaternary ammonium salts by treatment with alkylating or aralkylating agents, the reaction z. B. when using oleyl diethyl ethylenediamine and dimethyl sulfate proceeds according to the following equation: The new compounds have a pronounced soap character in aqueous solution, which they also after the addition of an alkaline agent, such as. B. alkali or soda, or an acid retained unchanged. In contrast, the diamines acylated on one side are precipitated in an alkaline solution, whereas the usual fatty acid soaps are precipitated in an acidic solution. The new connections thus combine the advantages of these two classes. Their field of application is very extensive; so you can z. B. can be used as a detergent and wetting agent or as an additive to dye baths in any alkaline, acidic or neutral reaction.
Beispiel i 38o Teile Oleyldiäthyläthylendiamin werden mit 142 Teilen jodmethyl gemischt. Unter starker Wärmeentwicklung tritt Umsetzung ein. Das Oleyldiäthyläthylendiaminjodmethylat bildet eine salbenartige Masse. Der Jodgehalt beträgt 24,2 0/p (ber. 24,33). Die Ausbeute ist quantitativ. Das Salz ist in Wasser .sowie in den meisten organischen Lösungsmitteln gut löslich. Durch Schüttehe seiner alkoholischen Lösung mit Silberoxyd wird die Ammoniumbase in Freiheit gesetzt. Man gewinnt sie aus dem Filtrat durch Vertreiben des Lösungsmittels als salbenartige Masse. In Wasser ist die Base leicht löslich; die Lösung reagiert stark alkalisch.Example i 38o parts of oleyl diethyl ethylenediamine are mixed with 142 parts iodomethyl mixed. Reaction occurs with strong heat development. The oleyl diethyl ethylenediamine iodomethylate forms an ointment-like mass. The iodine content is 24.2% / p (calc. 24.33). the Yield is quantitative. The salt is in water, as in most organic ones Solvents easily soluble. By pouring its alcoholic solution with silver oxide the ammonium base is set free. They are recovered from the filtrate Drive off the solvent as an ointment-like mass. The base is light in water soluble; the solution is strongly alkaline.
Beispiel e 38o Teile Oleyldiäthyläthylendiamin werden mit r26 Teilen Dimethylsulfat und 4000 Teilen Wasser kräftig verrührt. Vach etwa i Stunde ist die Reaktion beendet und alles in Lösung gegangen. Die Ausbeute ist quantitativ. Zusatz von Alkali gibt keine Fällung. Beispiel 3 382 Teile Stearyldiäthyläthylendiamin werden geschmolzen und mit i26 Teilen Dimethylsulfat kräftig verrührt. Das Stearyldiäthyläthylendiamindimethylsulfatbildet eine seifenartige Masse. Der Schwefelgehalt beträgt 6,28 °1o (ber. 6,3o). Die Ausbeute ist quantitativ. Die Verbindung ist in Wasser sowie in Alkohol leicht löslich.Example e 38o parts of oleyl diethylethylenediamine are vigorously stirred with 26 parts of dimethyl sulfate and 4000 parts of water. The reaction has ended after about 1 hour and everything has dissolved. The yield is quantitative. The addition of alkali does not result in any precipitation. Example 3 382 parts of stearyl diethyl ethylenediamine are melted and vigorously stirred with i26 parts of dimethyl sulfate. The stearyl diethyl ethylenediamine dimethyl sulfate forms a soap-like mass. The sulfur content is 6.28 ° 1o (cal. 6.3o). The yield is quantitative. The compound is easily soluble in water as well as in alcohol.
B,eispiel4 394Teile Oleyldiäthylpropylendiamin werden mit 1q.2 Teilen jodmethyl gemischt. Es tritt schwache Erwärmung ein. Nach längerem Stehen ist die Bildung des Oleyldiäthylpropylendiaminjodmethylates beendet. Es entsteht eine zähe plastische Masse. Ihr Jodgehalt beträgt 23,61/, (ber. 23,69). Die Ausbeute ist quantitativ. Die Verbindung ist in Wasser sowie in fast allen organischen Lösungsmitteln gut löslich.B, ebeispiel4 394 parts of oleyl diethylpropylenediamine are mixed with 1q.2 parts iodomethyl mixed. Slight heating occurs. After standing for a long time it is Formation of oleyldiethylpropylenediamine iodomethylates ended. The result is a tough one plastic mass. Their iodine content is 23.61 /, (calc. 23.69). The yield is quantitative. The compound is good in water as well as in almost all organic solvents soluble.
Das Oleyldiäthylpropylendiamin wurde durch achtstündiges Erhitzen molekularer Mengen Ölsäure und asymmetrischen Diäthylpropylendiamins im Rohr auf 18o bis 19o° dargestellt.The oleyl diethyl propylenediamine was obtained by heating for eight hours molecular amounts of oleic acid and asymmetric diethylpropylenediamine in the tube 18o to 19o ° shown.
Das asymmetrische Diäthylpropylendiamin wurde seinerseits durchUmsetzcn von y-Brompropylphthalimid mit Diäthylamin und Verseifen des hierbei entstandenen ;J-Diäthylaminopropylphthalimids erhalten. Die Base bildet eine farblose Flüssigkeit vom Kp. i 6o°. Beispiels 38o Teile Oleyldiäthylätliylendiamin werden mit 126,5 Teilen Benzylchlorid gemischt und 8 Stunden auf dem Wasserbade erwärmt. Die zuerst ölige Mischung wird dabei ziihflüssig. Die Ausbeute ist quantitativ. Der Chlorgehalt wurde zu 7,oo °(o gefunden und entspricht der Theorie. Das Oleyldiäthyläthylendiaminchlorbenzylat bildet eine äußerst zähe Masse, die beim Stehen teilweise kristallisiert. Die Verbindung ist in Wasser sowie in Alkohol leicht löslich. Beispiel 6 484 Teile Oleylbenzoyldiäthyläthylendiamin werden mit 126 Teilen Dimethylsulfat vermischt. Die Mischung erwärmt sich stark. Nach dem Erkalten erhält man in quantitativer Ausbeute das Oleylbenzoylaminoäthyldiäthylmethylammoniumsulfomethylat der Formel als sehr zähes, in Wasser lösliches Öl.The asymmetric diethylpropylenediamine was in turn obtained by reacting γ-bromopropylphthalimide with diethylamine and saponifying the resulting; γ-diethylaminopropylphthalimide. The base forms a colorless liquid with a boiling point of 60 °. Example 38o parts of oleyl diethyl ethylenediamine are mixed with 126.5 parts of benzyl chloride and heated on the water bath for 8 hours. The mixture, which was initially oily, becomes viscous. The yield is quantitative. The chlorine content was found to be 7,000 and corresponds to theory. The oleyl diethyl ethylenediamine chlorobenzylate forms an extremely viscous mass which partially crystallizes on standing. The compound is easily soluble in water and alcohol. Example 6 484 parts of oleylbenzoyl diethylethylenediamine are mixed with 126 parts After cooling, the oleylbenzoylaminoethyl diethylmethylammonium sulfomethylate of the formula is obtained in quantitative yield as a very viscous oil that is soluble in water.
Das Oleylbenzoyldiäthy läthylendiamin erhält man, indem man Oleyldiäthyläthylendiamin mit der molekularen Menge Ben;_o#lchlorid mischt. Nach dem Abklingen der starken Erwärmung wird das gebildete ölige Chlorhydrat in Äther gelöst, die Ätherlösung mit Kaliumcarbonat durchgeschüttelt und verdampft. Die gewünschte Base bleibt als Ö1 zurück.The oleylbenzoyl diethylethylenediamine is obtained by adding oleyldiethylethylenediamine mixed with the molecular amount of Ben; _o # oil chloride. After the strong subsides When heated, the oily chlorohydrate formed is dissolved in ether, the ethereal solution shaken with potassium carbonate and evaporated. The desired base remains as Ö1 back.
Beispiel ? 38o Teile- Oleyldiäthyläthylendiamin und 121 Teile Allylbromid werden zusammen vermischt. Nach einiger Zeit beginnt die NIischung unter schwacher Erwärmung dick zu werden. Nach einigen Stunden ist die Realztion beendet. Das entstandene Olevlaminoäthyldiäthylallylammoniumbromid bildet eine dicke, zähe Masse, die sich im@ Wasser zu einer schäumenden Flüssigkeit löst. Diese Lösung ist gegen Säure- und Alkalizusatz unempfindlich. Die Ausbeute ist quantitativ. Beispiel 8 38o Teile Oleyldiäthyläthylendiamin werden mit Zoo Teilen p-Toluolsulfonsäure'sithvlester einige Stunden auf dem Wasserbade erhitzt. Die Reaktion erfolgt unter Dickwerden der Mischung. Das so erhaltene 0leylaminoäthyltriäthylammonium-p-toluolsulfonat bildet eine dicke, zähe Masse. Die Ausbeute ist quantitativ. 48o Teile Diäthylaminoäthyliminodicarbonsäuredimenthylester (Beispiel 4 der Patentschrift 409 780) werden mit 126 Teilen Dimethylsulfat vermischt. Die Reaktion, die bald unter Erwärmung einsetzt, ist in kurzer Zeit beendet. Man erhält ein dickes 0l, das beim Stehen kristallinisch erstarrt. Das Methyldiäthylammoniumäthyliminod ica rbonsäuredimenthylestersulfomethylat bildet eine weiße, harte Masse, die sich in Wasser kolloidal löst. Die Ausbeute ist quantitativ.Example ? 38o parts of oleyl diethyl ethylenediamine and 121 parts of allyl bromide are mixed together. After a while, the mixture begins to thicken under slight warming. Realization is over after a few hours. The resulting Olevlaminoäthyldiäthylallylammoniumbromid forms a thick, viscous mass that dissolves in @ water to form a foaming liquid. This solution is insensitive to the addition of acids and alkali. The yield is quantitative. EXAMPLE 8 38o parts of oleyl diethylethylenediamine are heated with zoo parts of p-toluenesulfonate for a few hours on a water bath. The reaction occurs as the mixture thickens. The oleylaminoethyltriethylammonium p-toluenesulfonate thus obtained forms a thick, viscous mass. The yield is quantitative. 480 parts of dimethyl diethylaminoethyliminodicarboxylate (example 4 of patent specification 409 780) are mixed with 126 parts of dimethyl sulfate. The reaction, which soon sets in when heated, is over in a short time. A thick oil is obtained which solidifies in a crystalline manner on standing. The Methyldiäthylammoniumäthyliminod ica rbonsäuredimenthylestersulfomethylat forms a white, hard mass, which dissolves colloidally in water. The yield is quantitative.
Beispiel wo 407 Teile Stearyl -p - aminodimethylanilin (aus i Mol Stearylchlorid und ' 2 Mol p-Aminodimethylanilin, F. 117°) werden geschmolzen und mit 126 Teilen Dimethylsulfat vermischt. Es erfolgt eine heftige Reaktion, die in kurzer Zeit beendet ist. Das Reaktionsprodukt wird aus iooo Teilen Alkohol umgelöst. Das Ammoniumsalz bildet farblose Kristalle, die bei etwa 97° zu erweichen beginnen, ohne richtig zu schmelzen. Die Ausbeute an nicht umkristallisiertem Produkt ist quantitatit-. Beispiel ii 392 Teile Oleylpiperidyl-N-äthylamid werd2n mit 126 Teilen Dimethvlsulfat vermischt. Unter starker Erwärmung erfolgt in quantitativer Ausbeute die Bildung des quaternären Aminoniumsalzes. Das so erhaltene t.@leylaminoäthylmethylpiperidinifimsulfomethyiat der Formel bildet eine dicke, salbenartige Masse, die sich in Wasser zu einer schäumenden Flüssigkeit löst.Example where 407 parts of stearyl-p-aminodimethylaniline (from 1 mole of stearyl chloride and 2 moles of p-aminodimethylaniline, melting point 117 °) are melted and mixed with 126 parts of dimethyl sulfate. A violent reaction ensues, which ends in a short time. The reaction product is redissolved from 1,000 parts of alcohol. The ammonium salt forms colorless crystals that begin to soften at around 97 ° without actually melting. The yield of non-recrystallized product is quantitative. Example ii 392 parts of oleylpiperidyl-N-ethylamide are mixed with 126 parts of dimethyl sulfate. The quaternary aminonium salt is formed in quantitative yield when heated vigorously. The thus obtained t. @ Leylaminoäthylmethylpiperidinifimsulfomethyiat of the formula forms a thick, ointment-like mass that dissolves in water to form a foaming liquid.
Beispiel 12 434 Teile Oleylcyclohexyläthyläthvlendiamin werden mit 126 Teilen Dimethylsulfat vermischt. Beim Stehen tritt unter schwa-z-her Erwärmung Reaktion ein. Das Oleylaminoäthvlmethvläthvlcvclohexvlammoniumsulfometlivlat der Formel bildet ein dickes Öl, das sich in Wasser zu einer schäumenden Flüssigkeit löst.Example 12 434 parts of oleylcyclohexylethylethylenediamine are mixed with 126 parts of dimethyl sulfate. When standing, a reaction occurs with black warming. The Oleylaminoäthvlmethvläthvlcvclohexvlammoniumsulfometlivlat of the formula forms a thick oil that dissolves in water to form a foaming liquid.
Das Oleylcyclohexyläthyläthylendiamin (dickes öl) wurde durch Erhitzen inolektilarer Mengen Ölsäure und Cyclobexyliitliyläthylendiamin (Kp, 98 bis ioi°) erhalten. Letzteres wurde durch Reduktion des Äthylcvcloliexvlaminoacetonitrils mit \atriuui und absolutem Alkohol dargestellt. @thylev#_lohexylaminoacetonitril vom Kp" 118 bis 12O° bildet sich bei der Umsetzung von Cycloliexyläthylaminhydroclilorid mit Kaliuincvanid und Formaldehyd.The oleylcyclohexylethylethylenediamine (thick oil) was obtained by heating inolectile amounts of oleic acid and cyclobexylethylethylenediamine (boiling point 98 to 10 °). The latter was represented by reduction of the ethylcylolaminexvlaminoacetonitrile with atrium and absolute alcohol. @ thylev # _lohexylaminoacetonitrile with a boiling point of 118 to 12O ° is formed in the reaction of Cycloliexyläthylaminhydroclilorid with Kaliuincvanid and formaldehyde.
Beispiel 13 q.7o Teile Oleyldiäthylbenzylätliylendiamin werden mit
126 Teilen Dimethylsulfat vermischt. Unter starker Erwärmung erhält man in quantitativer
Ausbeute das OleylbenzylaminoäthylmethyldiäthylammoniumsuIfometlivlat von der Formel
Das Oleyldiäthylbenzylätliylendiamin, ein dickes Öl, wurde erhalten durch Erhitzen molekularer Mengen Ölsäure und Diäthylbenzyläthy lendiamin auf 18o bis 2oo°. Das Diäthylbenzyläthylendiamin (Öl vom Kp6,:; 124 bis 125°) entsteht durch Reduktion des Benzylidendiäthyläthylendiamines (Öl vom Kp, 128''), dem Kondensationsprodukt aus Benzaldehyd und asymm. Diäthyläthylendiamin.The oleyl diethylbenzylethylenediamine, a thick oil, was obtained by heating molecular quantities of oleic acid and diethylbenzylethylenediamine to 18o up to 2oo °. The diethylbenzylethylenediamine (oil of bp 6,:; 124 to 125 °) is created by Reduction of benzylidenediethylethylenediamines (oil of bp 128 ''), the condensation product from benzaldehyde and asymm. Diethylethylenediamine.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH559500X | 1927-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE559500C true DE559500C (en) | 1932-09-20 |
Family
ID=4520186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG73690D Expired DE559500C (en) | 1927-07-26 | 1928-06-26 | Process for the preparation of quaternary ammonium salts |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE559500C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2582292A (en) * | 1949-02-03 | 1952-01-15 | White Lab Inc | Preparation of benzal-imino compounds |
| DE762425C (en) * | 1938-07-20 | 1954-03-29 | Chem Fab Von Heyden A G | Process for the preparation of quaternary ammonium compounds containing an acylated benzylamino group |
| US3174985A (en) * | 1961-11-06 | 1965-03-23 | Ciba Ltd | Amine salt of a quaternary ammoniumcontaining acid |
-
1928
- 1928-06-26 DE DEG73690D patent/DE559500C/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE762425C (en) * | 1938-07-20 | 1954-03-29 | Chem Fab Von Heyden A G | Process for the preparation of quaternary ammonium compounds containing an acylated benzylamino group |
| US2582292A (en) * | 1949-02-03 | 1952-01-15 | White Lab Inc | Preparation of benzal-imino compounds |
| US3174985A (en) * | 1961-11-06 | 1965-03-23 | Ciba Ltd | Amine salt of a quaternary ammoniumcontaining acid |
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