We need your help.
In the late 1970’s, I saw an abstract of a talk at a conference that claimed to use TDA-1 [Tris(3,6-dioxaheptyl)amine], a polyether, to complex with magnesium and improve a Grignard reaction. I never heard the presentation or saw any other reference to it. I let that abstract slip into the depths of my memory.
This month, a procedure was reported in the patent shown in the diagram that uses catalytic TBAB in this Grignard reaction. I am having a hard time speculating the role of the TBAB.
Our subscribers are more knowledgeable and more intelligent than I. I am asking your help to suggest explanations of why the inventors added TBAB to this reaction. I am assuming that is not something they would do if it worked without TBAB.
Please indicate whether we can or should publish your name and company when you submit your suggested explanations.
Now contact Marc Halpern of PTC Organics to help the PTC community understand this 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!).
