DE692927C - Process for the preparation of capillary-active quaternary bases - Google Patents
Process for the preparation of capillary-active quaternary basesInfo
- Publication number
- DE692927C DE692927C DE1933D0066971 DED0066971D DE692927C DE 692927 C DE692927 C DE 692927C DE 1933D0066971 DE1933D0066971 DE 1933D0066971 DE D0066971 D DED0066971 D DE D0066971D DE 692927 C DE692927 C DE 692927C
- Authority
- DE
- Germany
- Prior art keywords
- bases
- capillary
- molecular weight
- preparation
- active quaternary
- 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
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- -1 aliphatic alkyl chlorides Chemical class 0.000 claims description 6
- POTIYWUALSJREP-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline Chemical compound N1CCCC2CCCCC21 POTIYWUALSJREP-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- IXTPCSZJZAKJTO-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a,9,9a,10,10a-tetradecahydroacridine Chemical compound N1C2CCCCC2CC2C1CCCC2 IXTPCSZJZAKJTO-UHFFFAOYSA-N 0.000 claims description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 150000002829 nitrogen Chemical class 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 239000002585 base Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000001348 alkyl chlorides Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 description 3
- BHDDSIBLLZQKRF-UHFFFAOYSA-N 1-dodecylpiperidine Chemical compound CCCCCCCCCCCCN1CCCCC1 BHDDSIBLLZQKRF-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 1
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
- KMWHQYDMBYABKL-UHFFFAOYSA-N 1-iodohexadecane Chemical compound CCCCCCCCCCCCCCCCI KMWHQYDMBYABKL-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/037—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements with quaternary ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Hydrogenated Pyridines (AREA)
Description
Verfahren zur Herstellung kapillaraktiver quartärer Basen Durch R e y,c hl e r (Chemisches -Zenträlblatt 1913 1I, S. i376) ist festgestellt worden, daß die Ammoni:aksubstitutionspro.dukte der höhermolekularen Fettalkohole Seifen sind, welche jedoch die aktive Alkylgruppe nicht wie die gewöhnlichen Seifen an solche Gruppen gebunden enthalten, die in wäßriger Lösung als Anionexi dissoziieren, sondern aktive Kationen bilden. Diese Erzeugnisse werden von R e y c h l e r als invertierte Seifen bezeichnet. Die praktische Erfahrung hat ergeben, -daß- sie zwar für eigentliche Waschzwecke weniger geeignet, jedoch bei andersgearteten Vorgängen, wie z. B. bei der Imprägnierung; Fettung, Avivage u. dgl. von Textilien, ferner beim Abziehen gewisser schwer zu entfernender Farbstoffe von der - Faser, beim Emulgieren -und Demulgieren u. dgl., mit Vorteil .anwendbar sind. Für diese Zwecke sind die alkalibeständigen aliphatischen quartären Ammoniumbasen besonders wertvoll; ihre Herstellung ist .aber sehr schwierig und kostspielig, da sich beispielsweise mit Trimethylamin nur Cetyljodid und Cetylbromid, nicht aber auch Cetylchlorid einwandfrei umsetzen. Aus ringförmige,. tertiären Basen von der Art des Pyridins lassen sich brauchbare quartäre Basen mit Hilfe von Alkylchloriden leichter gewinne;.. Im Vergleich mit den vorgenannten rein aliphatischen Basen sind diese Basen jedoch bedeutend unbeständiger, sie zersetzen sich beispiels«"eise schön in Gegenwart verdünnter Alkalien.Method of Making Capillary Active Quaternary Bases By R e y, c hl e r (Chemisches -Zenträlblatt 1913 1I, p. i376) has been determined that the ammonium substitution products of the higher molecular weight fatty alcohols are soaps which, however, do not have the active alkyl group like the ordinary soaps contain bound groups which dissociate in aqueous solution as anions, but form active cations. These products are known by R e y c h l e r as called inverted soaps. Practical experience has shown -that- they do less suitable for actual washing purposes, but for different types of processes, such as B. in the impregnation; Greasing, finishing and the like of textiles, furthermore when removing certain dyes that are difficult to remove from the fiber, when emulsifying -and demulsifying and the like, are .applicable with advantage. For these purposes the alkali-resistant aliphatic quaternary ammonium bases are particularly valuable; their Production is .but very difficult and costly because, for example, with Trimethylamine only cetyl iodide and cetyl bromide, but not also cetyl chloride perfectly realize. Made of annular,. tertiary bases of the type of pyridine can be Usable quaternary bases can be obtained more easily with the help of alkyl chlorides; .. In comparison with the aforementioned purely aliphatic bases, however, these bases are important more unstable, they decompose, for example, in the presence of more dilute ones Alkalis.
Es wurde nun gefunden, daß sich perhydrierte heterocyclische Basen von der Art des Piperidins mit höhenmolekularen Alkylchloriden ebenfalls leicht zu den N-Alkylpiperidinverbindungen umsetzen lassen und diese ihrerseits wieder mit niedrigen Alkylchloriden, Alkylsulfaten u. dgl. leicht und quantitativ quartäre Ammoniumverbindungen ergeben, die den an ihre textilchemischen Eigenschaften zu stellenden Anforderungen in jeder Beziehung genügen, insbesondere leicht von der Faseraufgenommen werden und gegenüber Alkalien eine .ausgezeichnete Beständigkeit aufweisen. Hierin zeigen sie :eine erheb= licht technische Überlegenheit gegenüber den bekannten, oben bereits erwähnten ringförmigen quartären Basen der Pyridinreihen.It has now been found that perhydrogenated heterocyclic bases of the type of piperidine with higher molecular weight alkyl chlorides also easy let convert to the N-alkylpiperidine compounds and these in turn again with lower alkyl chlorides, alkyl sulfates and the like easily and quantitatively quaternary Ammonium compounds give rise to their chemical properties meet the requirements in every respect, especially slightly from the Fibers are absorbed and an excellent resistance to alkalis exhibit. In this they show: a considerable technical superiority over the known, above-mentioned ring-shaped quaternary bases of the pyridine series.
Neben dem Piperidin kommen als Aus= gangsstoffe für dieses Verfahren andere rÜigförmige perhydrierte Stickstoffbasen, wie Perhydrochinolin und Perhydroacridin, in Betracht. Als - höhenmolekulare Alkylchloride eignen sich neben dem bereits erwähnten Cetylchlorid das Dodecyl-, das Tetradecyl-und das Octadecylchlorid sowie ähnliche höhenmolekulare Alkylrhloride, die mindestens 8 Kohlenstoffatome im Molekül enthalten. Neben den genannten niedrigen Alkylverbindungexi, die zur Anlagerung an die alkylierten Piperidine u. dgl. verwendet werden, kommen auch .andere niedrige Alkylhalogenidv erbindungen in Betracht, vorn denen bekannt ist, daß sie sich mit tertiären Aminen unter Bildung quartärer Ammoniumverbin; dungen umsetzen, wie z. B. Äthylchlorid, Oxy. äthylchlorid oder Äthylenchlorid (vgl. B e i 1'; stein, Handbuch der organischen Chemie. q.. Aufl., 1922, Bd. q., S.278 und 281; 1935, Bd.2o, S. 22o).In addition to piperidine, other volatile perhydrogenated nitrogen bases, such as perhydroquinoline and perhydroacridine, can be used as starting materials for this process. High molecular weight alkyl chlorides, in addition to the cetyl chloride already mentioned, are dodecyl, tetradecyl and octadecyl chloride and similar high molecular weight alkyl chlorides which contain at least 8 carbon atoms in the molecule. In addition to the lower alkyl compounds mentioned, which are used for addition to the alkylated piperidines and the like, other lower alkyl halide compounds are also suitable which are known to combine with tertiary amines to form quaternary ammonium compounds; implement applications, such as B. ethyl chloride, oxy. ethyl chloride or ethylene chloride (cf. B ei 1 '; Stein, Handbuch derorganischen Chemie. q .. Aufl., 1922, vol. q., p.278 and 281; 1935, vol. 20, p. 22o).
Beispiel i 86kg Piperidin werden mit 13okg Cetylchlorid 8 Stunden auf ioo bis 12o° erhitzt. Das wieder erkaltete Umsetzungsgemisch wird darauf durch Filtration von dem entstandenen Piperidinhydrochlorid befreit; in das Filtrat werden langsam, zeitweise unter Kühlung, 65 kg Methylsulfat eingerührt und die Masse gegebenenfalls bis zur Klarlöslichkeit in verdünnter Natronlauge nacherhitzt. Das Umsetzungsgut, welches aus Cetylmethylpiperidiniummethylsulfat besteht, vermag Paraffin, Cetylalkohol, Olivenöl u. dgl. leicht in wäßrige Emulsionen überzuführen, aus denen, insbesondere nach Zugabe von Natriumcarbonat, die Fett- oder Wachsbestandteile durch Faserstoffe leicht absorbiert werden.Example i 86 kg of piperidine are treated with 13 kg of cetyl chloride for 8 hours heated to 100 to 12o °. The reaction mixture, which has cooled down again, is then through The piperidine hydrochloride formed was removed by filtration; in the filtrate slowly, at times with cooling, stirred in 65 kg of methyl sulfate and the mass if necessary Post-heated until clear solubility in dilute sodium hydroxide solution. The implementation good, which consists of cetylmethylpiperidinium methyl sulfate, can paraffin, cetyl alcohol, Olive oil and the like easily converted into aqueous emulsions, from which, in particular After adding sodium carbonate, the fat or wax components are replaced by fibers be easily absorbed.
Beispiel 2 255 kg Piperidin und 102 kg Dodecylchlorid werden im Ölbad 3 Stunden auf i3o° imd i Stunde auf i 4o' erhitzt; hierbei erfolgt eine Umsetzung zu Laurylpiperidin und Piperidinhydrochlorid. 'Das sich aus dem Reaktionsgemisch ausscheidende Piperidi,nchlorhydrat wird abfiltriert und mit Benzol nachgewaschen. Die vereinigten Filtrate werden über festem Kaliumhydroxyd getrocknet, worauf das Benzol abdestilliert und der Rückstand der Vakuumdestillation unterworfen wird. Man erhält reines Laurylpiperidin in 98%iger Ausbeute. 25,3kg Laurylpiperidin werden nunmehr mit 24 kg Äthylenchlorhydrin mehrere Stunden im Ölbad bei 140' am Rückflußkühler .erhitzt. Nach Beendigung der Umsetzung wird das überschüssige Äthylenchlorhydrin abgedampft. Der verbleibende Rückstand, welcher aus 3-Oxyäthyllaurylpiperidiniumchlorid besteht, ist klar in Wasser löslich und kann mit Vorteil zur Herstellung von wäßrigen Ölemulsionen aller Art verwendet werden, welche zur Fettung von Textilien geeignet sind. Durch die Anwesenheit des 3-Oxyäthyllaurylpiperidiniumchlorids auf der Faser wird dabei gleichzeitig eine gewisse bakterizide und fungizide Wirkung erreicht, die den genannten Verbindungen eigen ist. Beispiel 3 2 Mol Perhydrochinolin und i .Mol eines Gemisches von Alkylchloriden, welches in bekannter Weise durch V eresterung mit Salzsäure aus dem durch Reduktion von Kokosölfettsäure gewonnenen Fettalkoholgemisch erhalten wurde, werden im Ölbad 3 bis q. Stunden auf i¢o' erhitzt. Es erfolgt Umsetzung zu dem Gemisch der entsprechenden Alkylperhydrochinoline unter gleichzeitiger Bildung von Perhydrochinolinhydrochlorid. Das Hydrochlorid scheidet sich aus dem Umsetzungsgemisch aus und wird ähnlich wie in Beispiel e daraus abgetrennt. Das als Rückstand verbleibende Gemisch der Alkylperhydrochinoline wird destilliert und ist in guter Ausbeute erhältlich.Example 2 255 kg of piperidine and 102 kg of dodecyl chloride are added in an oil bath Heated to 130 ° for 3 hours and to 14 ° for 1 hour; an implementation takes place here to laurylpiperidine and piperidine hydrochloride. 'That emerges from the reaction mixture The piperidium chlorohydrate which separates out is filtered off and washed with benzene. The combined filtrates are dried over solid potassium hydroxide, whereupon the Benzene is distilled off and the residue is subjected to vacuum distillation. Pure laurylpiperidine is obtained in 98% yield. 25.3kg of laurylpiperidine will be now with 24 kg of ethylene chlorohydrin for several hours in an oil bath at 140 'on the reflux condenser .heated. After completion of the reaction, the excess ethylene chlorohydrin evaporated. The remaining residue, which consists of 3-Oxyäthyllaurylpiperidiniumchlorid exists, is clearly soluble in water and can be used with advantage for the preparation of aqueous Oil emulsions of all kinds are used, which are suitable for greasing textiles are. Due to the presence of 3-Oxyäthyllaurylpiperidiniumchlorids on the fiber a certain bactericidal and fungicidal effect is achieved at the same time, which is peculiar to the compounds mentioned. Example 3 2 moles of perhydroquinoline and i .Mol of a mixture of alkyl chlorides, which in a known manner by esterification with hydrochloric acid from the fatty alcohol mixture obtained by reducing coconut oil fatty acid was obtained, are in the oil bath 3 to q. Heated to i ¢ o 'for hours. Implementation takes place to the mixture of the corresponding alkyl perhydroquinolines with simultaneous formation of perhydroquinoline hydrochloride. The hydrochloride separates out of the reaction mixture and is separated from it in a similar way to example e. That remaining as residue Mixture of the alkyl perhydroquinolines is distilled and is obtainable in good yield.
Das Gemisch der Alkylperhydrochinoline wird mit einem gewissen überschuß an Äthylenchlorhydrin mehrere Stunden am Rückflußkühler im Ölbad erhitzt. Nach Entfernung des überschüssigen Äthylenchlorhydrins erhält man als Umsetzungsprodukt ein Gemisch. hochmolekularer (3-Oxyäthylalkylperhydrochinoliniumchloride, welches zur Herstellung von, Emulsionen organischer, nn Wasser nicht löslicher Flüssigkeiten aller Art dienen kann. An Stelle des Perhydrochi;nolins kann als Ausgangsstoff in gleicher Weise auch das Perhydroacridin verwendet werden.The mixture of alkyl perhydroquinolines is used with a certain excess heated in ethylene chlorohydrin for several hours on the reflux condenser in an oil bath. After removal of the excess ethylene chlorohydrin is obtained as a reaction product as a mixture. high molecular weight (3-Oxyäthylalkylperhydrochinoliniumchloride, which is used for the production of, emulsions of organic liquids of all kinds that are insoluble in water are used can. Instead of perhydroquinoline, the starting material can be used in the same way Perhydroacridine can also be used.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1933D0066971 DE692927C (en) | 1933-11-19 | 1933-11-19 | Process for the preparation of capillary-active quaternary bases |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1933D0066971 DE692927C (en) | 1933-11-19 | 1933-11-19 | Process for the preparation of capillary-active quaternary bases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE692927C true DE692927C (en) | 1940-06-28 |
Family
ID=7059602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1933D0066971 Expired DE692927C (en) | 1933-11-19 | 1933-11-19 | Process for the preparation of capillary-active quaternary bases |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE692927C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1028076B (en) * | 1954-05-26 | 1958-04-17 | Basf Ag | Process for preparing threads from vegetable fibers and products made from them, which are used for fishing nets or similarly claimed finished goods |
-
1933
- 1933-11-19 DE DE1933D0066971 patent/DE692927C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1028076B (en) * | 1954-05-26 | 1958-04-17 | Basf Ag | Process for preparing threads from vegetable fibers and products made from them, which are used for fishing nets or similarly claimed finished goods |
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