MW irradiation and ionic liquids as green tools in hydrolyses and alcoholyses

The optimized HCl-catalyzed hydrolysis of alkyl diphenylphosphinates is described. The reaction times and pseudo-first-order rate constants suggested the iPr > Me > Et ∼ Pr ∼ Bu order of reactivity in respect of the alkyl group of the phosphinates. The MW-assisted p-toluenesulfonic acid (PTSA)...

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Autores principales:	Harsági Nikoletta, Szőllősi Betti, Kiss Nóra Zsuzsa, Keglevich György
Formato:	article
Lenguaje:	EN
Publicado:	De Gruyter 2020
Materias:	phosphinic derivatives hydrolysis alcoholysis microwave irradiation ionic liquids Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/a75b44ad55bd4fc9937fedb24f363eae
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spelling	oai:doaj.org-article:a75b44ad55bd4fc9937fedb24f363eae2021-12-05T14:10:49ZMW irradiation and ionic liquids as green tools in hydrolyses and alcoholyses2191-955010.1515/gps-2021-0001https://doaj.org/article/a75b44ad55bd4fc9937fedb24f363eae2020-12-01T00:00:00Zhttps://doi.org/10.1515/gps-2021-0001https://doaj.org/toc/2191-9550The optimized HCl-catalyzed hydrolysis of alkyl diphenylphosphinates is described. The reaction times and pseudo-first-order rate constants suggested the iPr > Me > Et ∼ Pr ∼ Bu order of reactivity in respect of the alkyl group of the phosphinates. The MW-assisted p-toluenesulfonic acid (PTSA)-catalyzed variation means a better alternative possibility due to the shorter reaction times, and the alkaline hydrolysis is another option. The transesterification of alkyl diphenylphosphinates took place only in the presence of suitable ionic liquids, such as butyl-methylimidazolium hexafluorophosphorate ([bmim][PF6]) and butyl-methylimidazolium tetrafluoroborate ([bmim][BF4]). The application of ethyl-methylimidazolium hydrosulfate ([emim][HSO4]) and butyl-methylimidazolium chloride ([bmim][Cl]) was not too efficient, as the formation of the ester was accompanied by the fission of the O–C bond resulting in the formation of Ph2P(O)OH. This surprising transformation may be utilized in the phosphinate → phosphinic acid conversion.Harsági NikolettaSzőllősi BettiKiss Nóra ZsuzsaKeglevich GyörgyDe Gruyterarticlephosphinic derivativeshydrolysisalcoholysismicrowave irradiationionic liquidsChemistryQD1-999ENGreen Processing and Synthesis, Vol 10, Iss 1, Pp 001-010 (2020)
institution	DOAJ
collection	DOAJ
language	EN
topic	phosphinic derivatives hydrolysis alcoholysis microwave irradiation ionic liquids Chemistry QD1-999
spellingShingle	phosphinic derivatives hydrolysis alcoholysis microwave irradiation ionic liquids Chemistry QD1-999 Harsági Nikoletta Szőllősi Betti Kiss Nóra Zsuzsa Keglevich György MW irradiation and ionic liquids as green tools in hydrolyses and alcoholyses
description	The optimized HCl-catalyzed hydrolysis of alkyl diphenylphosphinates is described. The reaction times and pseudo-first-order rate constants suggested the iPr > Me > Et ∼ Pr ∼ Bu order of reactivity in respect of the alkyl group of the phosphinates. The MW-assisted p-toluenesulfonic acid (PTSA)-catalyzed variation means a better alternative possibility due to the shorter reaction times, and the alkaline hydrolysis is another option. The transesterification of alkyl diphenylphosphinates took place only in the presence of suitable ionic liquids, such as butyl-methylimidazolium hexafluorophosphorate ([bmim][PF6]) and butyl-methylimidazolium tetrafluoroborate ([bmim][BF4]). The application of ethyl-methylimidazolium hydrosulfate ([emim][HSO4]) and butyl-methylimidazolium chloride ([bmim][Cl]) was not too efficient, as the formation of the ester was accompanied by the fission of the O–C bond resulting in the formation of Ph2P(O)OH. This surprising transformation may be utilized in the phosphinate → phosphinic acid conversion.
format	article
author	Harsági Nikoletta Szőllősi Betti Kiss Nóra Zsuzsa Keglevich György
author_facet	Harsági Nikoletta Szőllősi Betti Kiss Nóra Zsuzsa Keglevich György
author_sort	Harsági Nikoletta
title	MW irradiation and ionic liquids as green tools in hydrolyses and alcoholyses
title_short	MW irradiation and ionic liquids as green tools in hydrolyses and alcoholyses
title_full	MW irradiation and ionic liquids as green tools in hydrolyses and alcoholyses
title_fullStr	MW irradiation and ionic liquids as green tools in hydrolyses and alcoholyses
title_full_unstemmed	MW irradiation and ionic liquids as green tools in hydrolyses and alcoholyses
title_sort	mw irradiation and ionic liquids as green tools in hydrolyses and alcoholyses
publisher	De Gruyter
publishDate	2020
url	https://doaj.org/article/a75b44ad55bd4fc9937fedb24f363eae
work_keys_str_mv	AT harsaginikoletta mwirradiationandionicliquidsasgreentoolsinhydrolysesandalcoholyses AT szollosibetti mwirradiationandionicliquidsasgreentoolsinhydrolysesandalcoholyses AT kissnorazsuzsa mwirradiationandionicliquidsasgreentoolsinhydrolysesandalcoholyses AT keglevichgyorgy mwirradiationandionicliquidsasgreentoolsinhydrolysesandalcoholyses
_version_	1718371682454863872

MW irradiation and ionic liquids as green tools in hydrolyses and alcoholyses

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