This patent describes oxidative cleavage of oleic acid into two useful lower molecular weight acids and diacids. Previous technology uses two steps including isolation and purification of the catalyst system. This PTC technology enables a one step process with in-situ formation of the catalyst from the quaternary ammonium halide and phosphotungstic acid.
Five phase-transfer catalysts were screened and they all gave 100% conversion at 85 deg C and 5 hours versus only 38% conversion and only about 2% yield of the desired products without the phase-transfer catalyst. Quat chlorides performed slightly better than quat bromide. Cetyl pyridinium chloride which has better surfactant properties than the tetra-n-alkyl quats, gave the highest yield by a few percent.
Surprisingly, 2 mole% phase-transfer catalyst gave higher yield (by about 10%) than either 4 mole% PTC or 1 mole% PTC.
As is common with many water-sensitive PTC applications, the yield passes through a maximum at intermediate rpm. In other words, over-agitation should be avoided in this system.
PTC Organics has an excellent track record in developing low-cost high-performance oxidations using hydrogen peroxide. Now contact Marc Halpern of PTC Organics to explore how we can help improve process performance for your company’s oxidation reactions.
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!).
