Bench-Scale Synthetic Optimization of 1,2-bis(2-aminophenylthio)ethane (APO-Link) Used in the Production of APO-BMI Resin

Technical Report · Tue Jul 31 00:00:00 EDT 2007

DOI:https://doi.org/10.2172/926448· OSTI ID:926448

Wheeler, Hilary; Densmore, Crystal

The diamine reagent 1,2-bis(2-aminophenylthio)ethane is no longer commercially available but still required for the synthesis of the bismaleimide resin, APO-BMI, used in syntactic foams. In this work, we examined the hydrolysis of benzothiazole followed the by reaction with dichloroethane or dibromoethane. We also studied the deprotonation of 2-aminothiophenol followed by the reaction with dibromoethane. We optimized the latter for scale-up by scrutinizing all aspects of the reaction conditions, work-up and recrystallization. On bench-scale, our optimized procedure consistently produced a 75-80% overall yield of finely divided, high purity product (>95%).

• Research Organization: Honeywell FM&T - Kansas City Plant
• Sponsoring Organization: USDOE - National Nuclear Security Administration (NNSA)
• DOE Contract Number: AC04-01AL66850
• OSTI ID: 926448
• Report Number(s): KCP-613-8347
• Country of Publication: United States
• Language: English