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TNT: Trinitrotoluenes and Mono and Dinitrotoluenes

TNT: Trinitrotoluenes and Mono and Dinitrotoluenes

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THE THEORETICAL NITRATION OF TOLUENE 27<br />

MNT.<br />

1-2<br />

1-3<br />

1-4<br />

MNT.<br />

1-2<br />

1-3<br />

1-4<br />

GERMAN<br />

DNT.<br />

r1-2-41<br />

\ 1-2-6 /<br />

11-3-4<br />

I 1-2-3<br />

11-2-5<br />

f1-2-41<br />

11-2-6 i<br />

ITALIAN<br />

DNT.<br />

r1-2-41<br />

11-2-6 J<br />

r 1-3-4<br />

| 1-2-3<br />

11-3-6<br />

1-2-4<br />

<strong>TNT</strong>.<br />

1-2-4-6<br />

(1-2-3-4<br />

11-3-4-5<br />

1-2-3-4<br />

1-2-4-5<br />

1-2-4-6<br />

<strong>TNT</strong>.<br />

1-2-4-6<br />

1-2-3-4<br />

1-2-3-4<br />

1-3-4-5<br />

1-2-4-6<br />

The differences in these two schemes are self<br />

evident. The Italian theory is probably correct, in<br />

that much more is known about the behavior of the<br />

various nitrotoluenes on nitration than was known when<br />

the German theory was proposed. In defense of his<br />

theory, Hepp states as follows:<br />

" The theory is, that by nitration of meta nitrotoluene<br />

not less than five of the possible six trinitrotoluenes<br />

are formed. Beilstein <strong>and</strong> Kuhlberg hold<br />

that a trinitrotoluene is formed whose melting-point<br />

is 76 to 80°. They themselves doubt the constitution<br />

of this compound. ' Possibly/ they conclude,

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