Cocoalkyl benzyl bis[beta-hydroxypropyl] ammonium chloride might not seem like a mainstream phase-transfer catalyst but it was reported for one of the largest commercial PTC processes in history, namely the dehydrochlorination of dichlorobutane to chloroprene, monomer for synthetic rubber. US Patent 4,418,232 describes the use of this phase-transfer catalyst at a level of 1,115 ppm in a continuous process that produce chloroprene in 99.2% yield with only 0.8 mole% NaOH. Example 2 in the patent describes a throughput of 16 tons per hour.
This patent is taught in great detail by Mac Halpern in the 2-day course “Industrial Phase-Transfer Catalysis.”
The composition of cocoalkyl is typically about C18 10%, C16 10-20%, C14 20-30%, C12 40-50% and C10 10%.
Quaternary ammonium cations containing beta-hydroxypropyl and beta-hydroxyethyl groups are known to be used in PTC aldol condensation, PTC borohydride reduction and PTC dehydrohalogenation.
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!).
