Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger.
To synthesize high molecular weight poly(propylene fumarate) (PPF), fumaryl chloride and propylene glycol were reacted in the presence of potassium carbonate, which serves as a proton scavenger. Transesterification of the resulting low molecular weight oligomer led to a polymer with greater molecular weight than those from previous reaction methods without requiring the use of a catalyst. According to two-dimensional NMR, the backbone structure of this polymer was as expected and contained no byproducts formed by acid catalyzed addition across the fumarate double bond. Kinetic studies of the transesterification showed that the molecular weight reached a final Mn of 4900 (+/-700) and Mw of 9100 (+/-1300) after 16 h, while the polydispersity index remained below 1.8 throughout the reaction. Thus the PPF synthesized by the new method is of higher molecular weight and greater purity than our previously prepared material.
Peter
S J
SJ
Department of Chemical Engineering, Rice University, Houston, TX 77005-1892, USA.
Suggs
L J
LJ
Yaszemski
M J
MJ
Engel
P S
PS
Mikos
A G
AG
D000215:Acylation; D001843:Bone Cements / Q000138:chemical synthesis / Q000737:chemistry*; D002850:Chromatography, Gel; D016166:Free Radical Scavengers / Q000737:chemistry; D005650:Fumarates / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011126:Polypropylenes / Q000138:chemical synthesis / Q000737:chemistry*; D019946:Propylene Glycol / Q000737:chemistry; D011522:Protons; D017550:Spectroscopy, Fourier Transform Infrared
D001843:Bone Cements; D016166:Free Radical Scavengers; D005650:Fumarates; D011126:Polypropylenes; D011522:Protons; C097850:poly(propylene fumarate); D019946:Propylene Glycol