Mark Rubino of Vertellus sent us this very interesting article: Brachvogel, R.-C. et al. Self-assembly of dynamic orthoester cryptates. Nat. Commun. 6:7129 doi: 10.1038/ncomms8129 (2015).
The authors innovated a highly effective complexant with affinity for sodium ions between those of 15-crown-5 and 2.2.1 cryptand. This material is an orthoester cryptate in which nine oxygen donors are bound to the metal ion. The orthoester cryptate is stable against water in neutral solution, but susceptible to hydrolysis in the presence of water and acid. This opens up interesting possibilities for creative chemists.
A major reason that this complexant phase-transfer catalyst may be of higher than usual interest to industrial chemists is that it is produced from two relatively inexpensive bulk chemicals, trimethyl orthoacetate and diethylene glycol. Preparation uses trifluoroacetic acid as catalyst and a stoichiometric metal template.
We again express thanks to Mark Rubino for bringing this to our attention.
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!).
