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C
H
2
O
H
2
O
+
OH C
O
NH
2
H
y
d
r
o
l
y
t
i
c
D
e
g
r
a
d
a
t
i
o
n
T
=
2
5
0
C
S
t
e
p
1
NH
3 +
OH HO
H
2
O
-CO
2
NH
3
S
t
e
p
2
W
a
t
e
r
A
d
d
i
t
i
o
n
T
=
3
0
0
C
HO H
OH HO
H
2
O
H
2
O
H
2
O
H
2
O
H
2
O
Step 2
Water Addition
T=300C
HO
OH
HO OH
HO
OH
OH
S
t
e
p
3
F
r
e
e
R
a
d
i
c
a
l
T
>
3
5
0
C
S
t
e
p
3
F
r
e
e
R
a
d
i
c
a
l
T
>
3
5
0
C
S
t
e
p
3
F
r
e
e
R
a
d
i
c
a
l
T
>
3
5
0
C
H
2
+N
2
N
2
CO
2
+ H
2
O
H
2
O
H. .OH
Saturated Aliphatic Alcohol
Figure 8. Proposed pathway for carbamazepine degradation in sub-and supercritical water
Page 31 of 32
A
c
c
e
p
t
e
d
M
a
n
u
s
c
r
i
p
t
31
H
3
CO
O
OH
NH
CH
3
CH
3
H
2
O
H
2
O
H
2
O
H
2
O
S
t
e
p
1
H
y
d
r
o
l
y
t
i
c
D
e
g
r
a
d
a
t
i
o
n
2
0
0
C
<
T
<
2
5
0
C
CH
2 HO
OH
+
OH
OH OH
NH
3
CH
3
CH
3
HO
+
+
2-Propanol
Glycerine
S
t
e
p
2
W
a
t
e
r
A
d
d
i
t
i
o
n
T
=
3
0
0
C
CH
2 HO
HO H
H
OH
HO
H
S
t
e
p
3
F
r
e
e
R
a
d
i
c
a
l
T
>
3
5
0
C
Saturated Aliphatic Alcohol
H
2
O
H. .OH
S
t
e
p
3
F
r
e
e
R
a
d
i
c
a
l
T
>
3
5
0
C
S
t
e
p
3
F
r
e
e
R
a
d
i
c
a
l
T
>
3
5
0
C
N
2
+ H
2
CO
2
+H
2
O
CO
2
+H
2
O
Figure 9. Proposed pathway for metoprolol degradation in sub-and supercritical water
Page 32 of 32
A
c
c
e
p
t
e
d
M
a
n
u
s
c
r
i
p
t
32
H
2
N
S
O O
NH
N
O
H
2
O
S
t
e
p
1
H
y
d
r
o
l
y
t
i
c
D
e
g
r
a
d
a
t
i
o
n
2
0
0
C
<
T
<
2
5
0
C
H
2
N
HN
O
SO
3
Anyline
S
t
e
p
2
W
a
t
e
r
A
d
d
i
t
i
o
n
T
=
3
0
0
C
OH
H
2
N
OH
S
t
e
p
3
F
r
e
e
R
a
d
i
c
a
l
T
>
3
5
0
C
H
2
O
H. .OH
CO
2
+ H
2
O + N
2
H
2
N
HO
-NH
3
HN
CH
3
O
H
2
O
H
2
N
O
HO
-CO
2
H
2
N
S
t
e
p
2
W
a
t
e
r
A
d
d
i
t
i
o
n
T
=
3
0
0
C
NH
2
OH
+
+
S
t
e
p
3
F
r
e
e
R
a
d
i
c
a
l
T
>
3
5
0
C
H
2
SO
4
Step 3
Free Radical
T>350C
CO
2
+ H
2
O + N
2
Figure 10. Proposed pathway for sulfamethoxazole degradation in sub-and supercritical water