Adogen 464 is a registered trademark of Evonik and is essentially the same material as Aliquat 336 (registered trademark of BASF) which represents methyl tricaprylylammonium chloride. This material has an effective molecular weight of 432 g/mole since the “caprylyl” alkyl groups are a 2:1 molar mixture of octyl to decyl groups. As we teach in our 2-day PTC course, Adogen 464 has an effective C# of 27 and an effective q-value of 1.34.
The patent shown in the figure that issued this month used Adogen 464 for an etherification. Since Adogen 464 has an average of 27 carbon atoms, it distributes nearly exclusively into the toluene phase. This is important for workup. More hydrophilic quaternary ammonium phase-transfer catalysts, such as tetrabutylammonium, would distribute significantly into both the organic and aqueous phases. That affects aqueous waste treatment.
In this patent, tosylate was the leaving group. Tosylate is sometimes a catalyst poison in PTC systems. As we teach in our 2-day PTC course, in cases such as this one, tosylate does not bind irreversibly to the organophilic quat since it is competing for association with the anion of 7-hydroxy-4-(4-bromo-2-fluoroanilino)-6-methoxyquinazoline that contains many carbon atoms, more than tosylate.
If you want to learn how to choose a phase-transfer catalyst like an expert, now register for the public PTC course to be conducted in Prague in October 2019 or bring our highly valuable 2-day PTC course in-house to your company.
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!).
