PL421242A1 - New ammonium ionic liquids with tetraalkylammonium cation and 2-(2,4-dichlorophenoxy)propionate anion and method for obtaining them and their application as herbicides - Google Patents
New ammonium ionic liquids with tetraalkylammonium cation and 2-(2,4-dichlorophenoxy)propionate anion and method for obtaining them and their application as herbicidesInfo
- Publication number
- PL421242A1 PL421242A1 PL421242A PL42124217A PL421242A1 PL 421242 A1 PL421242 A1 PL 421242A1 PL 421242 A PL421242 A PL 421242A PL 42124217 A PL42124217 A PL 42124217A PL 421242 A1 PL421242 A1 PL 421242A1
- Authority
- PL
- Poland
- Prior art keywords
- butyl
- substituent
- methyl
- group
- dichlorophenoxy
- Prior art date
Links
- -1 tetraalkylammonium cation Chemical class 0.000 title abstract 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 title abstract 3
- 239000002608 ionic liquid Substances 0.000 title abstract 3
- 239000004009 herbicide Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- 125000001424 substituent group Chemical group 0.000 abstract 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 4
- 125000002704 decyl 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])* 0.000 abstract 4
- 239000003760 tallow Substances 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 abstract 3
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 abstract 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 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 abstract 2
- 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 abstract 2
- 125000001117 oleyl 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])=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])[H] 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 2
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 238000005349 anion exchange Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 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 amoniowe ciecze jonowe z kationem tetraalkiloamoniowym i anionem 2-(2,4-dichlorofenoksy)propionianowym o wzorze ogólnym 1, w których R1 oznacza podstawnik z grupy metyl, lub butyl; R2 oznacza podstawnik z grupy metyl, lub butyl, lub 2-hydroksyetyl, lub 2-chloroetyl; R3 oznacza podstawnik z grupy: uwodorniony tallow lub metyl, lub 2-hydroksyetyl, lub benzyl, lub decyl, lub butyl; R4 oznacza podstawnik z grupy uwodorniony tallow, lub dodecyl, lub oleyl, lub decyl, lub tetradecyl, lub oktadecyl, lub butyl, lub metyl. Zgłoszenie obejmuje też sposób ich otrzymywania, który polega na tym, że halogenek tetraalkiloamoniowy w którym R1 oznacza podstawnik z grupy metyl, lub butyl; R2 oznacza podstawnik z grupy metyl, lub butyl, lub 2-hydroksyetyl, lub 2-chloroetyl; R3 oznacza podstawnik z grupy: uwodorniony tallow, lub metyl, lub 2-hydroksyetyl, lub benzyl, lub decyl, lub butyl; R4 oznacza podstawnik z grupy uwodorniony tallow, lub dodecyl, lub oleyl, lub decyl, lub tetradecyl, lub oktadecyl, lub butyl, lub metyl, poddaje się reakcji wymiany anionu z roztworem wodorotlenku potasu, lub sodu, lub litu, w stosunku molowym od 1 : 0,95 do 1 : 1,05, korzystnie 1 : 1, w środowisku rozpuszczalnika organicznego z grupy: metanol; etanol; izopropanol; acetonitryl, korzystnie w metanolu, w temperaturze otoczenia przez okres korzystnie 5 - 10 minut, po czym usuwa się wytrącony osad nieorganiczny, dalej zobojętniania powstały wodorotlenek tetraalkiloamoniowy kwasem 2-(2,4-dichlorofenoksy)propionowego w stosunku molowym od 0,95 do 1,05, korzystnie 1 : 1, a następnie odparowuje się rozpuszczalnik, a produkt suszy się w temperaturze korzystnie 60°C, pod obniżonym ciśnieniem. Przedmiotem zgłoszenia jest także zastosowanie nowych amoniowych cieczy jonowych z kationem tetraalkiloamoniowym i anionem 2-(2,4-dichlorofenoksy)propionianowym jako herbicydy.The subject of the application are new ammonium ionic liquids with a tetraalkylammonium cation and a 2- (2,4-dichlorophenoxy) propionate anion of general formula 1, wherein R1 is a methyl substituent or butyl; R2 is a substituent from the group methyl, or butyl, or 2-hydroxyethyl or 2-chloroethyl; R3 is a substituent from the group: hydrogenated tallow or methyl, or 2-hydroxyethyl, or benzyl, or decyl, or butyl; R4 is a substituent from the group hydrogenated tallow, or dodecyl, or oleyl, or decyl, or tetradecyl, or octadecyl, or butyl, or methyl. The application also includes a method for their preparation, which consists in that the tetraalkylammonium halide in which R1 is a methyl substituent or butyl; R2 is a substituent from the group methyl, or butyl, or 2-hydroxyethyl or 2-chloroethyl; R3 is a substituent from the group: hydrogenated tallow, or methyl, or 2-hydroxyethyl, or benzyl, or decyl, or butyl; R4 is a substituent from the group hydrogenated tallow, or dodecyl or oleyl or decyl or tetradecyl or octadecyl or butyl or methyl and is subjected to an anion exchange reaction with a solution of potassium, or sodium, or lithium hydroxide in a molar ratio of from 1 : 0.95 to 1: 1.05, preferably 1: 1, in an organic solvent medium from the group: methanol; ethanol; isopropanol; acetonitrile, preferably in methanol, at ambient temperature for a period of preferably 5 - 10 minutes, after which the inorganic precipitate is removed, followed by neutralization of the resulting tetraalkylammonium hydroxide with 2- (2,4-dichlorophenoxy) propionic acid in a molar ratio of 0.95 to 1 , 05, preferably 1: 1, then the solvent is evaporated and the product is dried at a temperature of preferably 60 ° C under reduced pressure. The subject of the application is also the use of new ammonium ionic liquids with a tetraalkylammonium cation and 2- (2,4-dichlorophenoxy) propionate anion as herbicides.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL421242A PL231616B1 (en) | 2017-04-07 | 2017-04-07 | New ammonium ionic liquids with tetraalkylammonium cation and 2-(2,4-dichlorophenoxy)propionate anion and method for obtaining them and their application as herbicides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL421242A PL231616B1 (en) | 2017-04-07 | 2017-04-07 | New ammonium ionic liquids with tetraalkylammonium cation and 2-(2,4-dichlorophenoxy)propionate anion and method for obtaining them and their application as herbicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL421242A1 true PL421242A1 (en) | 2018-10-08 |
| PL231616B1 PL231616B1 (en) | 2019-03-29 |
Family
ID=63688077
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL421242A PL231616B1 (en) | 2017-04-07 | 2017-04-07 | New ammonium ionic liquids with tetraalkylammonium cation and 2-(2,4-dichlorophenoxy)propionate anion and method for obtaining them and their application as herbicides |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL231616B1 (en) |
-
2017
- 2017-04-07 PL PL421242A patent/PL231616B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL231616B1 (en) | 2019-03-29 |
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