PL413163A1 - New piperidinium ionic liquids with 2-(2,4-dichlorophenoxy)propionate anion and method for producing them and their application as herbicides - Google Patents
New piperidinium ionic liquids with 2-(2,4-dichlorophenoxy)propionate anion and method for producing them and their application as herbicidesInfo
- Publication number
- PL413163A1 PL413163A1 PL413163A PL41316315A PL413163A1 PL 413163 A1 PL413163 A1 PL 413163A1 PL 413163 A PL413163 A PL 413163A PL 41316315 A PL41316315 A PL 41316315A PL 413163 A1 PL413163 A1 PL 413163A1
- Authority
- PL
- Poland
- Prior art keywords
- dichlorophenoxy
- piperidinium
- ionic liquids
- new
- herbicides
- Prior art date
Links
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 title abstract 4
- 239000002608 ionic liquid Substances 0.000 title abstract 4
- 239000004009 herbicide Substances 0.000 title abstract 3
- -1 2-(2,4-dichlorophenoxy)propionate anion Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000005349 anion exchange Methods 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- KIOAHPKRMDELKS-UHFFFAOYSA-N azanium 2-(2,4-dichlorophenoxy)propanoate Chemical compound [NH4+].[O-]C(=O)C(C)OC1=CC=C(Cl)C=C1Cl KIOAHPKRMDELKS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001805 chlorine compounds Chemical group 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- HBPSMMXRESDUSG-UHFFFAOYSA-N piperidine;hydroiodide Chemical group I.C1CCNCC1 HBPSMMXRESDUSG-UHFFFAOYSA-N 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Przedmiotem zgłoszenia są nowe piperydyniowe ciecze jonowe z anionem 2-(2,4-dichlorofenoksy)propionianowym oraz sposób ich wytwarzania i zastosowanie jako herbicydy. Nowe ciecze jonowe zawierające anion 2-(2,4-dichlorofenoksy)propionianowy o ogólnym 1, w którym K oznacza kation piperydyniowy o wzorze ogólnym 2, w którym R oznacza podstawnik prostołańcuchowy o długości łańcucha węglowego od dwóch do osiemnastu atomów węgla. Sposób ich wytwarzania polega na tym, że czwartorzędowy chlorek, lub bromek, lub jodek piperydyniowy o wzorze ogólnym 3, w którym R oznacza podstawnik alkilowy o długości łańcucha węglowego od dwóch do osiemnastu atomów węgla, poddaje się reakcji wymiany anionu z solą sodową lub potasową, lub litową, lub amonową kwasu 2-(2,4-dichlorofenoksy)propionowego w stosunku molowym czwartorzędowej soli piperydyniowej do soli kwasu od 1:0,9 do 1:1,1, korzystnie 1:1, w temperaturze poniżej 100°C, korzystnie 20°C, w środowisku wodnym lub rozpuszczalniku organicznym z grupy: korzystnie metanol, albo etanol, albo propanol, albo izopropanol, albo butanol, po czym produkt izoluje się, a następnie suszy. Zgłoszenie dotyczy również zastosowania nowych cieczy jonowych zawierających 2-(2,4-dichlorofenoksy)propionianowy oraz kation piperydyniowy jako herbicydów.The subject of the application are new piperidinium ionic liquids with 2- (2,4-dichlorophenoxy) propionate anion as well as the method of their preparation and use as herbicides. New ionic liquids containing 2- (2,4-dichlorophenoxy) propionate anion of general 1, where K is a piperidinium cation of general formula 2, where R is a straight chain substituent with a carbon chain length of two to eighteen carbon atoms. The method of their preparation consists in the fact that the quaternary chloride, or bromide or piperidinium iodide of general formula 3, in which R is an alkyl substituent with a carbon chain length of two to eighteen carbon atoms, is subjected to an anion exchange reaction with a sodium or potassium salt, or lithium or ammonium 2- (2,4-dichlorophenoxy) propionic acid in a molar ratio of the quaternary piperidinium salt to the acid salt from 1: 0.9 to 1: 1.1, preferably 1: 1, at a temperature below 100 ° C, preferably 20 ° C, in an aqueous medium or organic solvent from the group: preferably methanol or ethanol or propanol or isopropanol or butanol, after which the product is isolated and then dried. The application also concerns the use of new ionic liquids containing 2- (2,4-dichlorophenoxy) propionate and piperidinium cation as herbicides.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL413163A PL229881B1 (en) | 2015-07-16 | 2015-07-16 | New piperidinium ionic liquids with 2-(2,4-dichlorophenoxy)propionate anion and method for producing them and their application as herbicides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL413163A PL229881B1 (en) | 2015-07-16 | 2015-07-16 | New piperidinium ionic liquids with 2-(2,4-dichlorophenoxy)propionate anion and method for producing them and their application as herbicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL413163A1 true PL413163A1 (en) | 2017-01-30 |
| PL229881B1 PL229881B1 (en) | 2018-09-28 |
Family
ID=57867732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL413163A PL229881B1 (en) | 2015-07-16 | 2015-07-16 | New piperidinium ionic liquids with 2-(2,4-dichlorophenoxy)propionate anion and method for producing them and their application as herbicides |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL229881B1 (en) |
-
2015
- 2015-07-16 PL PL413163A patent/PL229881B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL229881B1 (en) | 2018-09-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PL402516A1 (en) | Cation ionic liquids [2-(methacryloxy)ethyl]trimethyl ammonium chloride and their method for preparation | |
| PL416323A1 (en) | Methyl alkyl betaine 3,6-dichloro-2-methoxybenzoate, method for obtaining it and application as a herbicide | |
| PL413163A1 (en) | New piperidinium ionic liquids with 2-(2,4-dichlorophenoxy)propionate anion and method for producing them and their application as herbicides | |
| PL415210A1 (en) | Method for obtaining ammonium ionic liquids with cation derivative of betaine and nonenoate anion and their application as herbicides | |
| PL410372A1 (en) | New ammonium ionic liquids, alkoxymethyl[3-(methacryloylamino)propyl]dimetyl-ammonium 4-chloro-2-methylphenoxy)acetates, method for producing them and their application as herbicides | |
| PL410374A1 (en) | New ammonium ionic liquids, alkoxymethyl[3-(methacryloylamino)propyl]dimetyl-ammonium 2,4-dichlorophenoxy)acetates, method for obtaining them and their application as herbicides | |
| PL413162A1 (en) | New ammonium ionic liquids, containing dimethyldodecyl(carboxymethyl)ammonium cation, method for obtaining them and application as disinfectants | |
| PL399974A1 (en) | Ionic liquids with tetramethylene-1,4-bis (alkyldimethylammonium) cation and (4-chloro-2-methylphenoxy) acetate anion and the method of obtaining them | |
| PL416322A1 (en) | Bis(trifluoromethylsulfonyl)imide of alkyl[2-(2-hydroexyethoxy)ethyl]dimethylammonium and method for obtaining them and application as electrolytes | |
| PL419238A1 (en) | Alkyl[2-(2-hydroxyethoxy)ethyl]dimethylammonium 4-chloro-2-methylphenoxyacetates, method for obtaining them and application as herbicides | |
| PL417286A1 (en) | New ionic liquids with alkane-1,X-bis(decyldimethylammonium) cation and acetate anion, method for obtaining them and applications as bactericides | |
| PL412058A1 (en) | Disinfecting and washing agent, containing ionic liquids with benzethonium cation, method for obtaining it and application as a bactericidal medium | |
| PL418890A1 (en) | Alkyl[2-(2-hydroxyethoxy)ethyl]dimethylammonium 3,6-dichloro-2-methoxybenzoates, method for obtaining them and application as herbicides | |
| PL419507A1 (en) | New sweet bis-ammonium salts with alkyl-1,X-bis(decyldimethylammonium) cation and saccharinate anions, method for obtaining them and application as food deterrents | |
| PL420661A1 (en) | New bis-ammonium ionic liquids with alkyl-1,X-bis(bis(2-hydroxyethyl)octadec-9-en-ammonium) cation and method for obtaining them and application as food deterrents | |
| PL417453A1 (en) | New bis-ammonium ionic liquids with alkyl-1,X-bis(bis(2-hydroxyethyl)octadec-9-en ammonium) or bis(ethane)amino-2,2'-bis(bis(2-hydroxyethyl)octadec-9-en ammonium), or butene-1,4-bis(bis(2-hydroxyethyl)octadec-9-en ammonium) cation, method for obtaining them and applications as herbicides | |
| PL417452A1 (en) | Alkyldimethyl(carboxymethyl)ammonium 2-(2,4-dichlorophenoxy)propionates, method for obtaining them and application as a herbicides | |
| PL412742A1 (en) | New di[2-(2,4-dichlorophenoxy)propionates] alkano-1,X-bis(decyl dimethylammonium) bis-ammonium ionic liquids, method for obtaining them and applications as plant protection products | |
| PL417193A1 (en) | New bis-ammonium ionic liquids with alkane-1,X-bis(decyldimethylammonium) cation and formate anion, method for obtaining them and applications as bactericides | |
| PL417806A1 (en) | Ionic liquids with bis-ammonium cation and mandelate anion - method for obtaining them and applications as bactericides | |
| PL416162A1 (en) | New ionic liquids containing N-benzyl-2-(2-hydroxyethoxy)-N, N-dimethylammonium cation and method for obtaining them and application as herbicides | |
| PL415963A1 (en) | Benzethonium phenoxyacetates, method for obtaining them and their application as herbicides | |
| PL410425A1 (en) | New alkoxymethyl di(2-hydroxyethyl)methylammonium ionic liquids with sweet anion and method for producing them | |
| PL422180A1 (en) | New ionic liquids with 1,1,4,7,7-pentamethyl-1,4,7-trialkyl-diethylene-triammonium cation and (4-chloro-2-methylphenoxy)acetate anion, method for obtaining them and applications as herbicides | |
| PL417533A1 (en) | Ionic liquids with (2-bromoethyl)trimethylammonium, (3-bromopropyl)trimethylammonium and (2-bromoethyl)diethylammonium cation and method for obtaining them |