The structure and composition of the crude condensation products of 1, 2, 4-trimethylbenzene (1, 2, 4-TMB) with formaldehyde were studied. The crude condensation products were gas chromatographically separated to fraction I and II. IR spectrum of fraction I displayed two adsorption bands at 870cm
-1, characteristic of an one-adjacent hydrogen system, and at 810cm
-1, characteristic of a two-adjacent hydrogen system. Therefore, it was believed that fraction I was composed of 2, 3, 6, 2', 4', 5'-hexamethyldiphenylmethane (2, 3, 6, 2', 4', 5'-HMDPM) and 2, 3, 5, 2', 3', 6'-HMDPM.
Fraction II displayed bands 890-860cm
-1, but didn't displav a band near 810cm
-1. It was believed that fraction II was composed of 2, 4, 5, 2', 4, '5'-HMDPM and 2, 3, 5, 2', 4', 5'-HMDPM. These were also supported by NMR spectra of fraction I and II.
From cracking behaviors of a series of unsymmetric diarylmethanes, it was recognized that the fashion of cleavage between methylene carbon and aryl carbon is determined by the numbers of methyl group and their positions. From these results the hydrocracking behavior of unsymmetric HMDPM was determind, and the compositions of the crude condensation products were estimated as follows.
2, 4, 5, 2', 4', 5'-HMDPM 80-84%, 2, 3, 6, 2, '4', 5'-HMDPM 13-16%, 2, 3, 5, 2', 4', 5'-HMDPM<4%, 2, 3, 5, 2', 3', 6'-HMDPM<2%
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