PL416162A1 - New ionic liquids containing N-benzyl-2-(2-hydroxyethoxy)-N, N-dimethylammonium cation and method for obtaining them and application as herbicides - Google Patents
New ionic liquids containing N-benzyl-2-(2-hydroxyethoxy)-N, N-dimethylammonium cation and method for obtaining them and application as herbicidesInfo
- Publication number
- PL416162A1 PL416162A1 PL416162A PL41616216A PL416162A1 PL 416162 A1 PL416162 A1 PL 416162A1 PL 416162 A PL416162 A PL 416162A PL 41616216 A PL41616216 A PL 41616216A PL 416162 A1 PL416162 A1 PL 416162A1
- Authority
- PL
- Poland
- Prior art keywords
- product
- application
- hydroxyethoxy
- benzyl
- ionic liquids
- Prior art date
Links
- 239000002608 ionic liquid Substances 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 239000004009 herbicide Substances 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 4
- 239000000047 product Substances 0.000 abstract 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 abstract 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 abstract 1
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 abstract 1
- 229940087195 2,4-dichlorophenoxyacetate Drugs 0.000 abstract 1
- -1 4-chloro-2-methylphenoxyacetate anion Chemical class 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 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
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-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
- 239000006227 byproduct Substances 0.000 abstract 1
- 150000001805 chlorine compounds Chemical group 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 239000012074 organic phase Substances 0.000 abstract 1
- 239000012071 phase Substances 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
- 238000002360 preparation method Methods 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 239000012429 reaction media Substances 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
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Przedmiotem zgłoszenia są nowe ciecze jonowe, zawierające kation N-benzylo-2-(2-hydroksyetoksy)-N,N-dimetyloamoniowym o wzorze ogólnym 1, gdzie A- oznacza anion 2,4-dichlorofenoksyoctanowy lub 4-chloro-2-metylofenoksyoctanowy o wzorze ogólnym 2. Zgłoszenie obejmuje też sposób ich otrzymywania, który polega na tym, że czwartorzędowy chlorek lub bromek lub jodek N-benzylo-2-(2-hydroksyetoksy)-N,N-dimetyloamoniowy o wzorze ogólnym 3, poddaje się reakcji wymiany anionu z solą litową lub sodową lub potasową kwasu 2,4-dichlorofenoksyoctanowego lub 4-chloro-2-metylofenoksyoctanowego, w stosunku molowym czwartorzędowej soli amoniowej do soli kwasu od 1 : 0,9 do 1 : 1,1, korzystnie 1 : 1, w temperaturze co najmniej 10°C, w środowisku wodnym lub rozpuszczalniku organicznym z grupy: metanol, etanol, propanol, izopropanol, po czym produkt reakcji wydziela się z medium reakcyjnego techniką ekstrakcji dwufazowej za pomocą rozpuszczalnika organicznego z grupy: chloroform lub dichlorometan, po czym oddziela się fazę organiczną, rozpuszczalnik usuwa, a pozostałość będącą produktem suszy się, a następnie do wysuszonego produktu dodaje rozpuszczalnik organiczny z grupy: aceton lub acetonitryl lub metanol lub etanol lub izopropanol, po czym z rozpuszczalnika organicznego odsącza się powstały nieorganiczny produkt uboczny, z przesączu odparowuje się rozpuszczalnik, a produkt reakcji suszy się. W zgłoszeniu znajduje się też zastosowanie nowych cieczy jonowych.The subject of the application are new ionic liquids containing N-benzyl-2- (2-hydroxyethoxy) -N, N-dimethylammonium cation of general formula 1, where A- is 2,4-dichlorophenoxyacetate or 4-chloro-2-methylphenoxyacetate anion general formula 2. The application also includes a method for their preparation, which consists in the N-benzyl-2- (2-hydroxyethoxy) -N, N-dimethylammonium quaternary chloride or bromide or iodide of general formula 3 being subjected to an anion exchange reaction with lithium or sodium or potassium salt of 2,4-dichlorophenoxyacetic acid or 4-chloro-2-methylphenoxyacetic acid, in a molar ratio of the quaternary ammonium salt to the acid salt from 1: 0.9 to 1: 1.1, preferably 1: 1, in at a temperature of at least 10 ° C, in an aqueous medium or an organic solvent from the group: methanol, ethanol, propanol, isopropanol, after which the reaction product is separated from the reaction medium by two-phase extraction technique using an organic solvent from the group: chloroform or di chloromethane, after which the organic phase is separated, the solvent is removed and the product residue is dried, and then the organic product from the group: acetone or acetonitrile or methanol or ethanol or isopropanol is added to the dried product, after which the inorganic product formed is filtered off by-product, the solvent is evaporated from the filtrate and the reaction product is dried. The application also includes the use of new ionic liquids.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL416162A PL230475B1 (en) | 2016-02-17 | 2016-02-17 | New ionic liquids containing N-benzyl-2-(2-hydroxyethoxy)-N, N-dimethylammonium cation and method for obtaining them and application as herbicides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL416162A PL230475B1 (en) | 2016-02-17 | 2016-02-17 | New ionic liquids containing N-benzyl-2-(2-hydroxyethoxy)-N, N-dimethylammonium cation and method for obtaining them and application as herbicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL416162A1 true PL416162A1 (en) | 2017-08-28 |
| PL230475B1 PL230475B1 (en) | 2018-10-31 |
Family
ID=59684498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL416162A PL230475B1 (en) | 2016-02-17 | 2016-02-17 | New ionic liquids containing N-benzyl-2-(2-hydroxyethoxy)-N, N-dimethylammonium cation and method for obtaining them and application as herbicides |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL230475B1 (en) |
-
2016
- 2016-02-17 PL PL416162A patent/PL230475B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL230475B1 (en) | 2018-10-31 |
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