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In-Depth Information
CH
3
CH
3
NH
2
CH
2
H
3
C
H
3
C
OH
NH
2
CH
3
NH
CH
3
N
CH
3
N
CH
3
H
3
C
Monomethylamine Monoethylamine Dimethylamine Trimethylamine Dimethylethanolamine
(MMA)
(MEA)
(DMA)
(TMA)
(DMEA)
O
O
H
3
C
S
H
3
C
H
3
C
N
CH
3
H
N
N
N
S
H
3
C
H
3
C
Dimethylformamide
Dimethyldithiocarbamate N-Nitrosodimethylamine
(DMFA)
(DMDC)
(NDMA)
CH
3
O
N
H
3
C
H
3
C
N
H
3
C
N
N
CH
3
N
H
3
C
NH
2
CH
3
H
3
C
NH
Aniline
Dimethylaminobenzene 3-(Dimethylaminomethyl) indole 4-Dimethylaminoantipyrine
(DMAB)
(DMAI)
(DMAP)
Figure 6.33.
Structures of amines.
(TMA) by ferrate(VI) has been examined in detail [305]. Bicarbonate, cyanate,
and nitrogen were the products of the oxidation of MMA. The oxidation of
DMA and TMA resulted in formic and nitrogen as the major products of the
reactions. Fe(IV) was suggested as the reaction
intermediate (Eqs.
6.120-6.122):
2
−
+
(6.120)
FeO
CH NH
→
Fe IV CH NH H O
(
)
+
=
+
3
2
2
2
2
−
+
(6.121)
FeO
CH NH Fe IV HCO-NH
=
→
(
)
+
2
2
2
−
−
.
(6.122)
FeO
+
HCO-NH
→
Fe IV NCO H O
(
)
+
+
2
2
The product studies on the oxidation of aniline have been performed [374-
376]. In a previous study [375], both azobenzene and nitrobenzene products
were demonstrated. When an excess molar amount of ferrate(VI) to aniline
was used, nitrobenzene was the product of the reaction (Eq. 6.123), However,
in excess aniline, azobenzene was formed (Eq. 6.124):
2
−
+
(6.123)
FeO
C H NH
→
Fe II C H NO
(
)
+
5
5
2
5
5
2
2
−
+
.
(6.124)
FeO
C H NH
→
Fe II C H N NC H
(
)
+
=
5
5
2
5
5
5
5
In recent years, spin-trap EPR measurements were performed using
excess amounts of aniline to ferrate(VI) [376]. A free radical mechanism was
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