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Green Chemistry
Page 8 of 8
ARTICLE
Journal Name
and dried to give a quantitative yield of the product without further
purification. The remaining mother liquid and PTFE from the above 10 W. Herbst and K. Hung, Industrial Organic Pigments, WILEY-
9 E. Merino, Chem. Soc. Rev., 2011, 40, 3835-3853.
DOI: 10.1039/C8GC03982H
reaction and the washing water from the filtration were combined
VCH Verlag GmbH & Co. KGaA, Weinheim, 2004.
and then used in place of the initial H2O in a second cycle. The 11 Q. Yan, Water & Wastewater Engineering, 2003, 29(5), 40-43.
amounts of acetoacetanilide, 4-methyl-2-nitroaniline, NaNO2 and 2- 12 L. Pereira, In Environmental Protection Strategies for
naphthol were the same as for cycle 1 and the amount of added HCl
was reduced to 1.1 equiv. In total, 11 cycles were conducted in this
manner and all the reaction times from cycle 2 to cycle 11 were 30
Sustainable Development, Strategies for Sustainability, ed. A.
Malik and E. Grohmann, Springer Science+Business Media,
New York, 2012, Chapter 4, 111-162.
min with quantitative yields. The combined volume of the mother 13 A. Reife, T. River and H. Freeman, Text. Chem. Color. Am.
liquid and washing water from the 11th cycle was 15.5 mL. Dyest. Rep., 2000, 32(1), 56-60.
Wastewater and excess HCl recycling in the preparation of 14 J. Safari and Z. Zarnegar, RSC Adv., 2015, 5, 17738-17745.
Pigment Red 3 (10)
A mixture of 4-methyl-2-nitroaniline (1.05 equiv), HCl (3 equiv),
15 M. Velasco, C. Kinen, R. Rossi and L. Rossi, Dyes Pigm., 2011,
90, 259-264.
H2O (8 mL), NaNO2 (1.10 equiv, in 2 mL of H2O) and granular PTFE 16 P. Tundo, A. Loris and M. Selva, Green Chem., 2007, 9, 777-
(2.5 g) was mechanically stirred (400 rpm) at rt. After 20 min, 2- 779.
naphthol (1 g) was added. The reaction was continued for 60 min 17 H. Dabbagh, A. Teimouri and A. Chermahini, Dyes Pigm.,
when TLC indicated the completion of the reaction. After stopping 2007, 73, 239-244.
the reaction, the products were suspended in water while the 18 J. Jin, Z. Wen, J. Long, Y. Wang, T. Matsuura and J. Meng,
granular PTFE precipitated on the bottom of the flask. The Synth. Commun., 2000, 30(5), 829-834.
suspended products were filtered, washed with water (2 mL) and 19 B. Fang and P. Yang, CN Pat., 106752063 A, 2017.
dried to give a quantitative yield of the product without further 20 L. Liu, S. Feng and C. Li, ACS Sustainable Chem. Eng., 2016, 4,
purification. The granular PTFE, mother liquid and washing water
6754-6762.
from the filtration were then combined and used in a second cycle. 21 B. Li and C. Li, J. Org. Chem., 2014, 79, 2242-2254.
The amounts of 4-methyl-2-nitroaniline, NaNO2 and 2-naphthol 22 B. Li and C. Li, J. Org. Chem., 2014, 79, 8271-8277.
reduced to 1.0 equiv. Altogether 11 cycles were conducted in this
tools.
same way. All the reactions were complete in 60 min and had 24 H. Zollinger, Color Chemistry: Syntheses, Properties and
quantitative yields. After the 11th cycle, the combined volume of
the mother liquid and washing water was 17 mL.
Applications of Organic Dyes and Pigments, VCH
Verlagsgesellschaft mbH, Weinheim, 1987.
25 S. Thomas, PCT Int. Appl, 2008101842, 2016.
26 G. Shankarling, P. Deshmukh and A. Joglekar, J. Environ.
Chem. Eng., 2017, 5, 3302-3308.
Conflicts of interest
The authors declare no competing financial interest.
Notes and references
1
K. Hunger, Industrial Dyes: Chemistry, Properties,
Applications, WILEY-VCH Verlag GmbH
& Co. KGaA,
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F. Hamon, F. Pilard, F. Barbot and C. Len, Tetrahedron, 2009,
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Y. He, X. Gu, M. Guo and X. Wang, Opt. Mater., 2008, 31, 18-
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P. Sharma, N. Rane and V. Gurram, Bioorg. Med. Chem. Lett.,
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E. Marchevsky, R. Olsina and C. Marone, Talanta, 1985, 32(1),
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C. Han and X. Song, Yan Liao Sheng Chan Ji Shu (Techniques
in Manufacturing Industrial Pigments), Science Press, Beijing,
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8 | J. Name., 2012, 00, 1-3
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