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Thomas F. Derosa *, Rosemary Jennejahn
Texaco Research and Environmental Affairs, Beacon, New York 12508
*Correspondence to Thomas F. Derosa, Texaco Research and Environmental Affairs, Beacon, New York 12508
Trimethylsilyl-di-n-butylamine has been used to amidate methyl n-propionate and polymethylmethacrylate (PMMA) in THF. Trimethylsilyl (N-phenyl-p-phenyleneamine) amine was also prepared and used to amidate PMMMA and poly(ethylene-co-propylene)-graft-methylmethacrylate (OCP-graft-MMA) in THF and n-hexane, respectively. Amidations were performed between 55 and 65°C. When trimethylsilyl-di-n-butylamine was reacted with methyl propionate, less than 10% of the corresponding amide was generated because of a competitive aldol condensation. PMMA was smoothly amidated in excess of 60% using either trimethylsilyl(N-phenyl-p-phenyleneamine)amine or trimethylsilyl-di-n-butylamine without detectable competitive side reactions. OCP-graft-MMA was amidated in excess of 90% using a 5 M excess of trimethylsilyl(N-phenyl-p-phenyleneamine)amine in n-hexane.