Synthesis of a Novel Disperse Reactive Dye Involving a Versatile Bridge Group for the Sustainable Coloration of Natural Fibers in Supercritical Carbon Dioxide

Table 1. The isolated yields of the dye precursor obtained under different 
conditions.
Parameter
Isolated yield [%]
(i) Solvent dosage of DMF [mL]
a)
5.0
49.64
10.0
50.22
15.0
41.46
20.0
32.99
25.0
26.28
(ii) Molar ratio of reactants (n
1
:n
2
)
b),c)
1:10
50.22
1:1.5
51.09
1:20
51.85
1:2.5
52.55
1:30
53.43
(iii) Dosage of KOH [mmol]
d)
1.0
43.36
2.0
50.22
3.0
51.30
4.0
52.70
5.0
51.39
(iv) Dosage of copper [mmol]
e)
0
54.31
0.1
60.15
0.2
52.70
0.3
52.41
0.4
53.58
(v) Temperature [
°C]
f)
80
31.53
90
60.88
100
60.15
110
56.20
120
55.33
(vi) Time [h]
g)
4.0
42.63
6.0
48.47
8.0
52.41
10.0
60.88
12.0
59.27
a)
Conditions: 2.0 mmol of 1-chloroanthraquinone, N-phenylethylenediamine, 
and KOH, in the presence of 0.2 mmol Cu at 100 
°C under stirring for 
10.0 h; 
b)
(n
1
:n
2
): refers to the molar ratio of 1-chloroanthraquinone 
(n
1
) to N-phenylethylenediamine (n
2
); 
c)
Conditions: the mole ratios of 
1-chloroanthraquinone (n
1,
2.0 mmol) to N-phenylethylenediamine (n
2
) were 1:1, 
1:1.5, 1:2, 1:2.5, and 1:3 in the presence of 0.2 mmol Cu and 10.0 mL DMF at 
100 
°C under stirring for 10.0 h; 
d)
Conditions: 2.0 mmol of 1-chloroanthraquinone 
and 2.0 mmol of N-phenylethylenediamine in the presence of 0.2 mmol Cu 
and 10.0 mL DMF at 100 
°C under stirring for 10.0 h; 
e)
Conditions: 2.0 mmol 
of 1-chloroanthraquinone and 2.0 mmol of N-phenylethylenediamine in 
the presence of 4.0 mmol KOH and 10.0 mL DMF at 100 
°C under stirring 
for 10.0 h; 
f)
Conditions: 2.0 mmol of 1-chloroanthraquinone, 2.0 mmol of 
N-phenylethylenediamine, and 4.0 mmol KOH in the presence of 0.1 mmol 
Cu and 10.0 mL DMF under stirring for 10.0 h; 
g)
Conditions: 2.0 mmol of 
1-chloroanthraquinone, 2.0 mmol of N-phenylethylenediamine, and 4.0 mmol of 
KOH in the presence of 0.1 mmol Cu and 10.0 mL DMF under stirring at 90 
°C.

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