Glycidyl esters are an important class of compounds used in a variety of applications from pharmaceuticals to automotive.
The patent cited in the diagram describes the synthesis of glycidyl esters using phase-transfer catalysis, though yields are not reported. The inventor used excess epichlorohydrin as the solvent and tetrabutyl ammonium bromide as the phase-transfer catalyst in this solid-liquid PTC esterification.
It is possible that the bromide of TBAB is forming epibromohydrin in-situ which is co-catalyzing the reaction. The inventor used a reaction time of only 1 hr which is short for this type of esterification. He did not report optimization of moisture level in this system which we speculate would be crucial to achieve the highest productivity at low levels.
The inventor also used PTC for condensations of the glycidyl esters such as that described in Example 5 of the patent.
If your company could benefit from the highest performance esterification technology when reacting carboxylic acids (salts) with alkyl halides, now contact Marc Halpern of PTC Organics to access the best available expertise in PTC nucleophilic esterifications to improve your process performance.
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!).
