The second reaction shown in the diagram is an oxidation of a sulfide to a sulfone using Oxone® (registered trademark of Lanxess Deutschland). Oxone® is a mixture of salts including the active potassium peroxymonosulfate, which is more stable than potassium peroxymonosulfate by itself.
As we teach in our 2-day course “Industrial Phase-Transfer Catalysis,” from an industrial standpoint on a large scale, PTC can preferably be used with hydrogen peroxide to perform the oxidation of sulfides to sulfones. See for example Shintaku, T.; Katsura, T.; Itaya, N. (Sumika Fine Chemicals) 2004, US Patent 6,740,770 or Gargano, G.; Halpern, M.; (Ultraclean Fuel Pty Ltd) US Patent 10,214,697, 26-Feb-2019.
Also as we teach in our 2-day course “Industrial Phase-Transfer Catalysis,” PTC has been used in several oxidations using Oxone® including another oxidation of a sulfide to a sulfone, epoxidation of alkenes and a chiral oxidation (using a chiral auxiliary) shown in the April 2012 PTC Reaction of the Month.
Additional details for this oxidation can be found in the August 2021 PTC Tip of the Month. This includes a discussion that PTC should have been used (or at least considered) for the base-promoted first reaction.
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!).
The second reaction shown in the diagram is an oxidation of a sulfide to a sulfone using Oxone® (registered trademark of Lanxess Deutschland). Oxone® is a mixture of salts including the active potassium peroxymonosulfate, which is more stable than potassium peroxymonosulfate by itself.