As we teach in our 2-day course “Industrial Phase-Transfer Catalysis”, PTC works well for a variety of oxidations and epoxidations. Such reactions are typically performed under mild conditions and short reaction time. The reaction shown in the diagram was indeed performed under mild reaction conditions of time and temperature with an appropriate pH adjustment until complete conversion of the starting material was achieved.
Why was the isolated yield low? Was it due to the choice of fraction collected during the fractional distillation on the 20 g scale? Was it due to hydrolysis of the ester or ring opening of the epoxide? We don’t know. The reaction conditions appeared to be chosen well. The next process parameter we would screen that might be worthwhile would be a higher hypochlorite concentration.
The authors noted that they synthesized methyl glycidate and ethyl glycidate by following the same procedure, taking more caution with the evaporation stages as the boiling points of these products are low.
PTC Organics has developed highly selective epoxidations with very high throughout. If your company would like to explore licensing PTC Organics’ high-performance epoxidation technology, now contact Marc Halpern at PTC Organics.
About Marc Halpern
Dr. Halpern is founder and president of PTC Organics, Inc., the only company dedicated exclusively to developing low-cost high-performance green chemistry processes for the manufacture of organic chemicals using Phase Transfer Catalysis. Dr. Halpern has innovated PTC breakthroughs for pharmaceuticals, agrochemicals, petrochemicals, monomers, polymers, flavors & fragrances, dyes & pigments and solvents. Dr. Halpern has provided PTC services on-site at more than 260 industrial process R&D departments in 37 countries and has helped chemical companies save > $200 million. Dr. Halpern co-authored five books including the best-selling “Phase-Transfer Catalysis: Fundamentals, Applications and Industrial Perspectives” and has presented the 2-day course “Practical Phase-Transfer Catalysis” at 50 locations in the US, Europe and Asia.
Dr. Halpern founded the journal “Industrial Phase-Transfer Catalysis” and “The PTC Tip of the Month” enjoyed by 2,100 qualified subscribers, now beyond 130 issues. In 2014, Dr. Halpern is celebrating his 30th year in the chemical industry, including serving as a process chemist at Dow Chemical, a supervisor of process chemistry at ICI, Director of R&D at Sybron Chemicals and founder and president of PTC Organics Inc. (15 years) and PTC Communications Inc. (20 years). Dr. Halpern also co-founded PTC Interface Inc. in 1989 and PTC Value Recovery Inc. in 1999. His academic breakthroughs include the PTC pKa Guidelines, the q-value for quat accessibility and he has achieved industrial PTC breakthroughs for a dozen strong base reactions as well as esterifications, transesterifications, epoxidations and chloromethylations plus contributed to more than 100 other industrial PTC process development projects.
Dr. Halpern has dedicated his adult life to his family and to phase-transfer catalysis (in that order!).
