Ayat Hammad, Alaa Rahhal, Ghadeer Daghash, Meena Basri and Husam M. Younes

College of Pharmacy, Qatar University, Doha, Qatar
Pharmaceutics & Polymeric Drug Delivery Research Laboratory, College of Pharmacy, Qatar University, Doha, Qatar

Abstract:

Objectives: To carry out synthesis and characterization of (2,2-) bis(e-caprolactone-4-yl)-propane known also as bis-caprolactone (BCP) for further use as a crosslinking agent in ring opening polymerization of lactone biocompatible and biodegradable polymers.

Methodology: The 2,2-bis(4- hydroxyhexyl) propane was oxidized to the corresponding dicyclohexyl-4,4’-dione (Diketone) which was further reacted using the Baeyer-Villiger oxidation reaction to form BCP. Both diketone and BCP were fully characterized by 1H and 13C. Nuclear Magnetic Resonance (NMR), Fourier Transform Infrared Spectroscopy (FT-IR), Mass Spectroscopy (MS), Differential Scanning Calorimetry (DSC) and Elemental Analysis (EA) of C, H, N, O.

Results: The NMR and FT-IR confirmed the structure of BCP. The MS analysis resulted in a parent ion peak (M) at m/z=269 that corresponds to the molecular weight of BCP which was also confirmed by EA. The DSC showed a sharp endothermic peak at an onset of 185 oC. The yield was ranging from 65-70% and the purity analysis using DSC indicated a purity of not less than 98%.

Conclusion: A pure BCP was prepared and characterized as a candidate crosslinking agent to be used in ring opening polymerization of lactone biocompatible and biodegradable polymers.