Synthesis and Extractive Properties of Dialkylaminomethyl-substituted Dialkylamides of Diphenylphosphinoylacetic Acid

Abstract

Dialkylamides of diphenylphosphinoylacetic acids, dialkylaminomethyl-substituted by the methylene group, were prepared by means of the Mannich reaction from diphenyl(dialkylcarbamoylmethyl)-phosphine oxides or by reaction of the latter compounds with tetraethylmethylenediamine. Extractive ability of the obtained compounds toward U(VI) and Pd(II) in nitrate media was studied.Alkylation of dialkylamides of diphenylphosphinoylacetic acid by the methylene group is most commonly complicated by the low CH acidity of methylene protons. For this reason, a-alkyl-substituted dialkylamides of diphenylphosphinoylacetic acid are usually prepared starting from potassium derivatives of corresponding dialkylamides [1] or preliminary synthesized a-alkyl-substituted diphenylphosphinoylacetic acids [2]. In the present work we studied feasibility of direct dialkylaminomethylation of certain ÄÄÄÄÄÄÄÄÄÄÄÄ dialkylamides of diphenylphosphinoylacetic acid for preparing complex-forming agents of a new type.Ethyl (diethoxyphosphinoyl)acetate whose methylene protons exhibit enhanced acidity due to the electron-acceptor effect of the ethoxycarbonyl group reacts with Formalin and diethylamine under Mannich reaction conditions to form a condensation product, diethyl 2,4-bis(diethoxyphosphinoyl)pentane-1,5-dioic acid [3]. (EtO) 2 P(O)CH 2 C(O)OEt + Et 2 NH + CH 2 O 76 (EtO) 2 P(O)CHC(O)OEt g CH 2 g (EtO) 2 P(O)CHC(O)OEt ÄÄÄÄÄÄÄÄÄÄÄÄ Unlike ethyl (diethoxyphosphinoyl)acetate, N,N-dialkyl(diphenylphosphinoyl)acetamides Ph 2 P(O)CH 2 .

Synthesis and investigation of biological activity of phosphorylated amines and amides

“…Compounds I-II [1], III [13], IV [14], VI [15], and VIII [3] were prepared by the known procedures. N,N'-Dicyclohexyl-N,N'-bis(diphenylphosphinoylacetyl) …”

Ligands for f-element extraction used in the nuclear fuel cycle

“…The presence of the amine (CMPO-7) caused a decrease in the extraction of U(VI), Th(IV) and Ln(III) and an increase in the extraction of Pd(II), a fission product that can interfere with the extraction of An and Ln(III). 108 The selectivity for Pd(II) was more pronounced with a triazolyl chain (D Pd = 21 with CMPO-6 and D Pd = 0.05 with DPhDBCMPO), whereas the extraction of U(VI) and Ln(III) was only slightly affected, but the ligand was unable to extract Th(IV). 109 Pre-organisation of two triazolylCMPO units on a benzene platform (Chart 17) increased the selectivity for Pd(II) even more, with D Pd values up to 62 at 3 M HNO 3 .…”

Alkylation and pre-organisation of diglycolamide ligands on flexible platforms for nuclear waste treatment

“…and Ln(III) and an increase in the extraction of Pd(II), a fission product that can interfere with the extraction of An and Ln(III). 108 The selectivity for Pd(II) was more pronounced with a triazolyl chain (DPd = 21 with CMPO-6 and DPd = 0.05 with DPhDBCMPO), whereas the extraction of U(VI) and Ln(III) was only slightly affected, but the ligand was unable to extract Th(IV). 109 …”