PL430023A1 - New ionic liquids with 1-alkyl-1-azonia-4-azabicyclo[2.2.2]octane cation and an anion of natural origin, their preparation and use as antifeedants - Google Patents
New ionic liquids with 1-alkyl-1-azonia-4-azabicyclo[2.2.2]octane cation and an anion of natural origin, their preparation and use as antifeedantsInfo
- Publication number
- PL430023A1 PL430023A1 PL430023A PL43002319A PL430023A1 PL 430023 A1 PL430023 A1 PL 430023A1 PL 430023 A PL430023 A PL 430023A PL 43002319 A PL43002319 A PL 43002319A PL 430023 A1 PL430023 A1 PL 430023A1
- Authority
- PL
- Poland
- Prior art keywords
- alkyl
- azonia
- azabicyclo
- ionic liquids
- anion
- Prior art date
Links
- 239000002608 ionic liquid Substances 0.000 title abstract 3
- 150000001450 anions Chemical class 0.000 title abstract 2
- 230000001887 anti-feedant effect Effects 0.000 title 1
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 abstract 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000005643 Pelargonic acid Substances 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000003957 anion exchange resin Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Przedmiotem wynalazku są nowe ciecze jonowe z kationem 1-alkilo-1-azonia-4-azabicyklo[2.2.2]oktanu zawierającym w podstawieniu alkilowym parzystą ilość atomów węgla - od 4 do 18, o wzorze ogólnym 1, w którym A- oznacza anion kwasu pelargonowego o wzorze 2. Zgłoszenie obejmuje też sposób ich otrzymywania, który polega na tym, że bromek 1-alkilo-1-azonia-4-azabicyklo[2.2.2]oktanu, o wzorze ogólnym 3 rozpuszcza się w wodzie i wprowadza do kolumny wypełnionej silnie zasadową żywicą anionowymienną oraz wodą, dalej eluat zobojętnia się kwasem pelargonowym, rozpuszczonym uprzednio w metanolu, w stosunku stechiometrycznym wodorotlenek 1-alkilo-1-azonia-4-azabicyklo[2.2.2]oktanu do kwasu pelargonowego 1:1, dalej reakcję prowadzi się w wodzie w temperaturze korzystnie 20°C, w czasie od 20 do 30 minut, korzystnie przez 30 minut, po czym rozpuszczalnik odparowuje się pod obniżonym ciśnieniem, a powstały produkt suszy pod obniżonym ciśnieniem w temperaturze od 50 do 55°C, korzystnie 55°C. Przedmiotem zgłoszenia jest także zastosowanie nowych cieczy jonowych jako antyfidanty.The subject of the invention are new ionic liquids with a 1-alkyl-1-azonia-4-azabicyclo [2.2.2] octane cation having an even number of carbon atoms in the alkyl substitution - from 4 to 18, of the general formula 1, in which A- is an anion pelargonic acid of the formula 2. The application also covers the method of their preparation, which consists in dissolving 1-alkyl-1-azonia-4-azabicyclo [2.2.2] octane bromide of the general formula 3 in water and introducing it into the column filled with strongly basic anion exchange resin and water, then the eluate is neutralized with pelargonic acid, previously dissolved in methanol, in a stoichiometric ratio of 1-alkyl-1-azonia-4-azabicyclo [2.2.2] octane hydroxide to pelargonic acid 1: 1, then the reaction carried out in water at a temperature of preferably 20 ° C for 20 to 30 minutes, preferably 30 minutes, then the solvent is evaporated off under reduced pressure and the resulting product is dried under reduced pressure at a temperature of 50 to 55 ° C, preferably 55 ° C. The subject of the application is also the use of new ionic liquids as antifidants.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL430023A PL240029B1 (en) | 2019-05-23 | 2019-05-23 | New ionic liquids with 1-alkyl-1-azonia-4-azabicyclo[2.2.2]octane cation and an anion of natural origin, their preparation and use as antifeedants |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL430023A PL240029B1 (en) | 2019-05-23 | 2019-05-23 | New ionic liquids with 1-alkyl-1-azonia-4-azabicyclo[2.2.2]octane cation and an anion of natural origin, their preparation and use as antifeedants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL430023A1 true PL430023A1 (en) | 2020-11-30 |
| PL240029B1 PL240029B1 (en) | 2022-02-07 |
Family
ID=73551781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL430023A PL240029B1 (en) | 2019-05-23 | 2019-05-23 | New ionic liquids with 1-alkyl-1-azonia-4-azabicyclo[2.2.2]octane cation and an anion of natural origin, their preparation and use as antifeedants |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL240029B1 (en) |
-
2019
- 2019-05-23 PL PL430023A patent/PL240029B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL240029B1 (en) | 2022-02-07 |
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