Abstracts Book - IMRC 2018

• SB1-P082
SYNTHESIS AND CHARACTERIZATION OF POLYMER POLOXAMER
F-407 FUNCTIONALIZED WITH TRIPROPYL AND TRIHEPTYL
CITRATES THROUGH WILLIAMSON ETHER SYNTHESIS
Jose Eduardo Hernandez Torres 1 , Ernesto Rivera Becerril 2 , Gerardo Perez Hernandez 2
1 Universidad Autónoma Metropolitana, Posgrado en Ciencias Naturales e Ingenieria, Mexico.
2
Universidad Autónoma Metropolitana, Ciencias Naturales e Ingenieria, Mexico.
Introduction. Poloxamer is a copolymer composed of three nonionic blocks,
formed by a central hydrophobic chain (polyoxypropylene), and two hydrophilic
end chains (polyoxyethylene). The Poloxamer F-407 is widely used as a drug
vehicle or as a confinement matrix. Its physicochemical properties allow to
obtain modified release pharmaceutical systems. In addition, citric acid has
been incorporated in pharmaceutical applications as precursor of new
materials. The objective of this work was functionalizing the poloxamer polymer
F-407 with citrates derived citric acid, which will generate new materials with
potential applications in the confinement and release of drugs. Experimental
Part. The halogenation of poloxamer F-407 (1) was carried out using thionyl
chloride, for two hours at room temperature and acetonitrile as reaction
behavior with dimethylformamide as a catalyst, obtaining the dihalogenated
compound (2). Later 2 was functionalized via the Williamson ether synthesis
reaction using tripropyl or triheptyl citrates in acetone. The reaction was carried
out at room temperature under constant agitation for 6 days, obtaining the
respective functionalized poloxamers (3 and 4). The characterization of the
compounds obtained were determined using FTIR instruments (Brucker Tensor
27) and NMR (FT-NMR (60 MHz) ANASAZI). Results. Yellowish solids were
obtained for compounds 3 and 4. IR spectra show stretches at 1736 and 1740
cm -1 belonging to the carbonyl group and stretching at 1108 and 1100 cm -1
corresponding to the stretching C-O-C for compounds 3 and 4 respectively.
Compound 3: NMR 1 H 1.52 (m, −CH2CH2CH3); 2.74 (sa, -CH2 citric); 3.98 (m, CH2Pr).
NMR 13C 44.1, 80.0, 170.4 and 174.0 ppm. Compound 4: NMR 1 H 1.24 (m,
−CH2CH2CH3); 2.74 (sa, -CH2 citric); 3.94 (m, CH2Hep). NMR 13 C 43.3, 80.1, 170.7,
174.4 ppm. Conclusion. Two new materials were obtained and characterized by
spectroscopic techniques of RMN 1 H, RMN 13 C and IR-TF, next its potential
application in confinement and drug release would be studied.
Keywords: Poloxamer F-407, Functionalization, Tripropyl and triheptyl citrates
Presenting authors email: eduardotorreshd@gmail.com