Abstract
A study has been made of gas evolution during the cure of o-, p-cresols, o- and p-tert-butylphenols, 4-methyl-2-tert-butylphenol and 2,6-di-tert-butylphenol by hexamethylene tetramine. It is shown that at 403–448 K ∼0·5 mole of ammonia is evolved per ortho-position of phenols; under these conditions p-phenols react at a low rate with hexamethylene tetramine. It was found that from 4-methyl-2-tert-butylphenol, with a tritium labelled hydroxyl ∼ 92 wt.% of tritium is evolved in the ammonia. It is shown that N-hydroxybenzyl dihydrobenzoxazines are formed from phenols having one free ortho-position, while polydihydrobenzoxazines are formed from those with two free ortho-positions.
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