PL422180A1 - 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 - Google Patents

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

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Publication number
PL422180A1
PL422180A1 PL422180A PL42218017A PL422180A1 PL 422180 A1 PL422180 A1 PL 422180A1 PL 422180 A PL422180 A PL 422180A PL 42218017 A PL42218017 A PL 42218017A PL 422180 A1 PL422180 A1 PL 422180A1
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Poland
Prior art keywords
methylphenoxy
chloro
pentamethyl
ionic liquids
cation
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PL422180A
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Polish (pl)
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PL232557B1 (en
Inventor
Juliusz Pernak
Monika Akwarska
Katarzyna Marcinkowska
Damian Kaczmarek
Tadeusz Praczyk
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Politechnika Poznańska
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Priority to PL422180A priority Critical patent/PL232557B1/en
Publication of PL422180A1 publication Critical patent/PL422180A1/en
Publication of PL232557B1 publication Critical patent/PL232557B1/en

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Przedmiotem zgłoszenia są nowe ciecze jonowe z kationem 1,1,4,7,7-pentametylo-1,4,7-trialkylodietylenotriamoniowy oraz anionem (4-chloro-2-metylofenoksy)octanowym o wzorze ogólnym 2 gdzie: R oznacza łańcuch alkilowy od ośmiu do czternastu atomów węgla, a A- oznacza anion (4-chloro-2-metylofenoksy)octowy o wzorze 3. Zgłoszenie obejmuje też sposób otrzymywania powyższych cieczy, który polega na tym, że czwartorzędowy tribromek 1,1,4,7,7-pentametylo-1,4,7-trialkylodietylenotriamoniowym o wzorze ogólnym 1, poddaje się reakcji wymiany anionu z solą sodową lub potasową kwasu (4-chloro-2-metylofenoksy)octowego w stosunku molowym czwartorzędowej soli triamoniowej do soli kwasu 1:3, w temperaturze od 25°C do 35°C, korzystnie 25°C, w rozpuszczalniku organicznym z grupy: metanol, etanol lub butanol po czym z rozpuszczalnika organicznego odsącza się powstały nieorganiczny produkt uboczny, z przesączu odparowuje się rozpuszczalnik, następnie produkt reakcji suszy się w temperaturze korzystnie, 70°C pod obniżonym ciśnieniem. Przedmiotem zgłoszenia jest też zastosowanie powyższych nowych cieczy jonowych.The subject of the application are new ionic liquids with a 1,1,4,7,7-pentamethyl-1,4,7-trialkyldiethylenetriammonium cation and an (4-chloro-2-methylphenoxy) acetate anion of general formula 2 where: R is the alkyl chain from eight to fourteen carbon atoms, and A- is (4-chloro-2-methylphenoxy) acetic anion of formula 3. The application also includes a method for obtaining the above liquids, which consists in the fact that the quaternary tribromide 1,1,4,7,7 pentamethyl-1,4,7-trialkyldiethylenetriammonium of general formula 1, anion exchange reaction with (4-chloro-2-methylphenoxy) acetic acid sodium or potassium salt in a molar ratio of quaternary triammonium salt to 1: 3 acid salt in temperature from 25 ° C to 35 ° C, preferably 25 ° C, in an organic solvent from the group: methanol, ethanol or butanol, then the organic inorganic by-product is filtered off from the organic solvent, the solvent is evaporated from the filtrate, then the reaction product is dried at a temperature of preferably 70 ° C under reduced pressure. The subject of the application is also the use of the above new ionic liquids.

PL422180A 2017-07-10 2017-07-10 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 PL232557B1 (en)

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PL422180A PL232557B1 (en) 2017-07-10 2017-07-10 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

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Application Number Priority Date Filing Date Title
PL422180A PL232557B1 (en) 2017-07-10 2017-07-10 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

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PL422180A1 true PL422180A1 (en) 2019-01-14
PL232557B1 PL232557B1 (en) 2019-06-28

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008106107A1 (en) * 2007-02-26 2008-09-04 Dow Agrosciences Llc Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides
PL399974A1 (en) * 2012-07-16 2014-01-20 Politechnika Poznanska Ionic liquids with tetramethylene-1,4-bis (alkyldimethylammonium) cation and (4-chloro-2-methylphenoxy) acetate anion and the method of obtaining them
CN103931651A (en) * 2014-03-27 2014-07-23 胜利油田胜利化工有限责任公司 Preparation method of gemini bis-quaternary ammonium salt bactericide
PL407017A1 (en) * 2014-01-31 2015-08-03 Instytut Ochrony Roślin Bis (ammonium) herbicidal ionic liquids with alkyldiyl-bis (dimethylalkyl ammonium) cations and method for producing them

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008106107A1 (en) * 2007-02-26 2008-09-04 Dow Agrosciences Llc Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides
PL399974A1 (en) * 2012-07-16 2014-01-20 Politechnika Poznanska Ionic liquids with tetramethylene-1,4-bis (alkyldimethylammonium) cation and (4-chloro-2-methylphenoxy) acetate anion and the method of obtaining them
PL407017A1 (en) * 2014-01-31 2015-08-03 Instytut Ochrony Roślin Bis (ammonium) herbicidal ionic liquids with alkyldiyl-bis (dimethylalkyl ammonium) cations and method for producing them
CN103931651A (en) * 2014-03-27 2014-07-23 胜利油田胜利化工有限责任公司 Preparation method of gemini bis-quaternary ammonium salt bactericide

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