Polymeric Pseudo-Liquid Membranes from Poly(N-oleylacrylamide)

Abstract

A polymeric pseudo-liquid membrane (PPLM) was constructed from poly(N-oleylacrylamide) (PC18AAm), which exhibited a rubbery state under membrane transport conditions and used as the membrane matrix. In the present study, dibenzo-18-crown-6 (DB18C6) and dibenzo-21-crown-7 (DB21C7) were adopted as transporters for alkali metal ions. KCl was adopted as a model substrate for DB18C6 and CsCl the latter. Chiral transporter, O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide (AAMC) was used as a transporter for chiral separation of a racemic mixture of phenylglycine (Phegly). The l-somer was transported in preference to the antipode. The present study revealed that PPLMs are applicable to membrane transport, such as metal ion transport and chiral separation.

Chiral Separation in Preparative Scale: A Brief Overview of Membranes as Tools for Enantiomeric Separation

“…O-Allyl-N-(9-anthracenylmethyl) cinchonidinium bromide was used as a transporter for chiral separation of a racemic mixture of phenylglycine (7). The L-isomer was transported in preference to the antipode [65].…”

“…A complex is formed between the chiral selector and one enantiomer at the interface of donating and organic solutions, which is then transported through the liquid membrane to another aqueous solution (receiving phase), frequently in the presence of a pH or concentration gradients [26,51]. Several liquid membranes containing different types of chiral selectors, including biomacromolecules such as human serum albumin [61,62] or enzymes [63], chiral crown ethers [64,65], cyclodextrins [66][67][68], chiral small molecules [69][70][71], and calixarenes [72,73], have been reported. Chiral liquid membrane is known as the combination of membrane separation and chiral extraction technology, which can carry out an effective real-time process to extract and recover compounds by a single unit operation.…”

“…In this technique, the chiral selector, which may be either a carrier or a solvent species, is used to introduce enantioselectivity into the separation process. However, the drawback of the liquid membrane is lack of long-term stability; the solvent consisting of membrane solution may evaporate, or the transporter and/or transporter/target molecule complex may be washed out during operation [65].…”

Polymeric Pseudo-Liquid Membranes from Polymethacrylate Derivative Bearing Oligodimethylsiloxane Unit

“…Up to now, six types of liquid membrane has been proposed as durable liquid membranes, such as (1) polymer liquid crystal composite membranes [12,13]; polymer inclusion membranes (PIMs) [14][15][16][17][18][19][20][21][22]; 3organogel membranes [23,24]; (4) stabilization of supported liquid membranes [25,26]; (5) liquid membranes based on ionic liquids [27][28][29]; and (6) polymeric pseudo-liquid membranes (PPLMs) [30][31][32][33][34][35][36][37].…”

“…In the studies on PPLMs, polymeric materials, which show rubbery state and fluidity, were chosen as a membrane matrix dissolving a carrier and were working as a barrier separating source and receiving phases. So far, poly(2-ethylhexyl methacrylate) (P2EHMA), with glass transition temperature (T g ) of -14.3 °C [33], poly(2-ethylhexyl acrylate) (P2EHA) with T g of -60.5 °C [34], poly(dodecyl methacrylate) (PC12MA) with T g of -66.3 °C [35], poly(N-oleylacrylamide) (PC18AAm) with T g of -85.0 °C [37] and poly(octadecyl methacrylate) (PC18MA) with T g of -101.2 °C [36,42] were adopted as membrane matrices for PPLMs.…”