Synthesis of diethyl 2-{[3-(triethoxysilyl)propyl]amino}ethylphosphonate

doi:10.26565/2220-637X-2020-34-03

Yuliia I. Chuiko V.N. Karazin Kharkiv National University, School of Chemistry, 4 Svobody sqr., 61022 Kharkiv, Ukraine https://orcid.org/0000-0002-1552-2106
Yuriy V. Kholin V.N. Karazin Kharkiv National University, School of Chemistry, 4 Svobody sqr., 61022 Kharkiv, Ukraine https://orcid.org/0000-0003-1369-741X
Maksim A. Kolosov V.N. Karazin Kharkiv National University, School of Chemistry, 4 Svobody sqr., 61022 Kharkiv, Ukraine https://orcid.org/0000-0002-6714-0513

DOI: https://doi.org/10.26565/2220-637X-2020-34-03

Keywords: 3-aminopropyltriethoxysilane (APTES), alkylation, polycondensation, surface modification

Abstract

Diethyl 2-{[3-(triethoxysilyl)propyl]amino}ethylphosphonate is promising reagent for the modification of silica surface and thus for the creation of chelate adsorbents for extraction of d‑metals ions from water media.

Diethyl 2-{[3-(triethoxysilyl)propyl]amino}ethylphosphonate was synthesized by alkylation of 3-aminopropyltriethoxysilane (APTES) with diethyl vinylphosphonate under quick neat heating. The possible alternative approaches to the synthesis of this compound were investigated (alkylation of APTES and N-acetylAPTES) as well as behavior of APTES towards heating in absolute ethanol and THF. APTES was shown to be not stable in absolute ethanol, that is caused by polycondensation processes. Because of this fact, previously reported protocol of diethyl 2‑{[3‑(triethoxysilyl)propyl]amino}ethylphosphonate synthesis in ethanol turned to be impossible.

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