Reduction of 3-nitro-4-methoxy-acetylaniline to 3-amino-4-methoxy-acetylaniline catalyzed by metallic Cu nanoparticles at low reaction temperature

Chemical Engineering Journal

Volumn 262, Issue , 2015, Pages 427-435

  Feng, Yonghai ^a   Wang, Aili ^a   Yin, Hengbo ^a   Yan, Xiaobo ^a   Shen, Lingqin ^a  

^a JIANGSU UNIVERSITY   (China)

Author keywords

3 Amino 4 methoxy acetanilide; 3 Nitro 4 methoxy acetanilide; Cu nanoparticle; Heterogeneous catalysis; Kinetic

Indexed keywords

ACETANILID; ACTIVATION ENERGY; CATALYSIS; CATALYST ACTIVITY; CATALYST SELECTIVITY; CATALYSTS; KINETICS; NANOPARTICLES; PARTICLE SIZE; REACTION KINETICS; SELECTIVE CATALYTIC REDUCTION;

3-AMINO-4-METHOXY ACETANILIDE; 3-NITRO-4-METHOXY ACETANILIDE; AVERAGE PARTICLE SIZE; CETYL TRIMETHYL AMMONIUM BROMIDES; CHEMICAL REDUCTION METHODS; CU NANO-PARTICLES; METALLIC CU NANOPARTICLES; REACTION KINETIC MODELS;

SYNTHESIS (CHEMICAL);

EID: 84949116577     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2014.09.120     Document Type: Article

References (38)

1. de Noronha R.G., Romăo C.C., Fernandes A.C. Highly chemo- and regioselective reduction of aromatic nitro compounds using the system silane/oxo-rhenium complexes. J. Org. Chem. 2009, 74:6960-6964.
2. Sunwoo K.H., Kim D.C., Shin K.J., Yoo K.H., Kim D.J., Park S.W. Monoazo disperse dyes containing ethyleneimine moieties Part 1: Synthesis and application of some monoazo disperse dyes derived from 3-amino-4-methoxyacetanilide. Dyes Pigments 1999, 41:19-29.
3. Marlic C.A., Motamed S., Quinn B. Structure determination and synthesis of fluoro nissl green: An RNA-binding fluorochrome. J. Org. Chem. 1995, 60:3365-3369.
4. Liu Y., Lu Y., Prashad M., Repic O., Blacklock T.J. A practical and chemoselective reduction of nitroarenes to anilines using activated iron. Adv. Synth. Catal. 2005, 347:217-219.
5. 4 as a catalyst in the conversion of p-nitrophenol to p-aminophenol. Mater. Lett. 2008, 62:3900-3902.
6. Cárdenas-Lizana F., Gómez-Quero S., Jacobs G., Ji Y., Davis B.H., Kiwi-Minsker L., Keane M.A. Alumina supported Au-Ni: surface synergism in the gas phase hydrogenation of nitro-compounds. J. Phys. Chem. C 2012, 116:11166-11180.
7. 3. Catal. Commun. 2008, 9:475-481.
8. Wang A., Yin H., Ren M., Lu H., Xue J., Jiang T. Preparation of nickel nanoparticles with different sizes and structures and catalytic activity in the hydrogenation of p-nitrophenol. New J. Chem. 2010, 34:708-713.
9. Annie J.K., Cecile S., Alan M.A., Shawn D.W. Selective catalytic hydrogenation of nitro groups in the presence of activated heteroaryl halides. J. Org. Chem. 2011, 76:9841-9844.
10. Bawane S.P., Sawant S.B. Hydrogenation of p-nitrophenol to metol using Raney nickel catalyst: Reaction kinetics. Appl. Catal. A: Gen. 2005, 293:162-170.
11. Jiang C., Yin H., Chen Z. Kinetics of ortho-nitrochlorobenzene hydrogenation on platinum/carbon catalyst. Chin. J. Chem. Eng. 2004, 12:652-657.
12. Lara P., Suárez A., Collière V., Philippot K., Chaudret B. Platinum N-heterocyclic carbene nanoparticles as new and effective catalysts for the selective hydrogenation of nitroaromatics. ChemCatChem 2014, 6:87-90.
13. Singh U.K., Krska S.W., Sun Y. Deactivation of heterogeneous hydrogenation catalysts by alcoholic solvents. Org. Process Res. Dev. 2006, 10:1153-1156.
14. Yadav G.D., Mewada R.K. Novelties of azobenzene synthesis via selective hydrogenation of nitrobenzene over nano-fibrous Ag-OMS-2 - mechanism and kinetics. Chem. Eng. J. 2013, 221:500-511.
15. Liu Y., Fang Y., Lu X., Wei Z., Li X. Hydrogenation of nitrobenzene to p-aminophenol using Pt/C catalyst and carbon-based solid acid. Chem. Eng. J. 2013, 229:105-110.
16. Vilella I.M.J., de Miguel S.R., Scelza O.A. Study of the performance of Pt catalysts supported on activated carbon felt and granular carbon for nitrobenzene hydrogenation. Chem. Eng. J. 2005, 114:33-38.
17. Pogorelić I., Filipan-Litvić M., Merkaš S., Ljubić G., Cepanec I., Litvić M. Rapid, efficient and selective reduction of aromatic nitro compounds with sodium borohydride and Raney nickel. J. Mol. Catal. A: Chem. 2007, 274:202-207.
18. Benz M., Prins R. Kinetics of the reduction of aromatic nitro compounds with hydrazine hydrate in the presence of an iron oxide hydroxide catalyst. Appl. Catal. A: Gen. 1999, 183:325-333.
19. Kumarraja M., Pitchumani K. Simple and efficient reduction of nitroarenes by hydrazine in faujasite zeolites. Appl. Catal. A: Gen. 2004, 265:135-139.
20. Lauwiner M., Rys P., Wissmann J. Reduction of aromatic nitro compounds with hydrazine hydrate in the presence of an iron oxide hydroxide catalyst. I. The reduction of monosubstituted nitrobenzenes with hydrazine hydrate in the presence of ferrihydrite. Appl. Catal. A: Gen. 1998, 172:141-148.
21. Furst A., Moor R.E. Reductions with hydrazine hydrate catalyzed by Raney nickel. II. Aromatic nitro compounds to intermediate products. J. Am. Chem. Soc. 1957, 79:5492-5493.
22. 6 and DBU. Tetrahedron 2008, 64:10195-10200.
23. Rahaim R.J., Maleczka R.E. An advantageous route to oxcarbazepine (Trileptal) based on palladium-catalyzed arylations free of transmetallating agents. Org. Lett. 2005, 7:5087-5090.
24. Banik B.K., Mukhopadhyay C., Venkatraman M.S., Becker F.F. A facile reduction of aromatic nitro compounds to aromatic amines by samarium and iodine. Tetrahedron Lett. 1998, 39:7243-7246.
25. Yu C., Liu B., Hu L. Samarium(0) and 1,1'-dioctyl-4,4'-bipyridinium dibromide: a novel electron-transfer system for the chemoselective reduction of aromatic nitro groups. J. Org. Chem. 2001, 66:919-924.
26. Basu M.K., Becker F.F., Banik B.K. Ultrasound-promoted highly efficient reduction of aromatic nitro compounds to the aromatic amines by samarium/ammonium chloride. Tetrahedron Lett. 2000, 41:5603-5606.
27. McLaughlin M.A., Barnes D.M. A practical and selective reduction of nitroarenes using elemental sulfur and mild base. Tetrahedron Lett. 2006, 47:9095-9097.
28. Verho O., Nagendiran A., Tai C.W., Johnston E.V., Bäckvall J. Nanopalladium on amino-functionalized mesocellular foam as an efficient and recyclable catalyst for the selective transfer hydrogenation of nitroarenes to anilines. ChemCatChem 2014, 6:205-211.
29. Rahman A., Jonnalagadda S.B. Swift and selective reduction of nitroaromatics to aromatic amines with Ni-Boride-Silica Catalysts system at low temperature. Catal. Lett. 2008, 123:264-268.
30. 3 nanocatalyst prepared in water-in-oil microemulsion: effects of water-to-surfactant mole ratio and type of reducing agent. Ind. Eng. Chem. Res. 2011, 50:7338-7344.
31. Wunder S., Frank P., Yan L., Yu M., Matthias B. Kinetic analysis of catalytic reduction of 4-nitrophenol by metallic nanoparticles immobilized in spherical polyelectrolyte brushes. J. Phys. Chem. C 2010, 114:8814-8820.
32. Wu F., Qiu L., Ke F., Jiang X. Copper nanoparticles embedded in metal-organic framework MIL-101(Cr) as a high performance catalyst for reduction of aromatic nitro compounds. Inorg. Chem. Commun. 2013, 32:5-8.
33. Neri G., Musolino M.G., Milone C., Visco A.M., Di Mario A. Mechanism of 2,4-dinitrotoluene hydrogenation over Pd/C. J. Mol. Catal. A: Chem. 1995, 95:235-241.
34. Feng Y., Yin H., Wang A., Xie T., Jiang T. Selective hydrogenation of maleic anhydride to succinic anhydride catalyzed by metallic nickel catalysts. Appl. Catal. A: Gen. 2012, 425-426:205-212.
35. Zhang Q., Lu J., Ma L., Lu C., Xu X., Liang Q., Li X. Catalytic hydrogenation for the green synthesis of N-3-amino-4-methoxyphenyl acetamide. Fine Chem. Intermed. 2008, 38:41-43. (Chinese).
36. Ma R., Hu S., Xin J., Hou J., Gou F., Lu R., Lu L. Selective catalytic hydrogenation of 3-nitro-4-methoxyacetanilide. Fine Chem. 2006, 23:1138-1141. (Chinese).
37. Huang X., Wang X., Wang X., Wang X., Tan M., Ding W., Lu X. P123-stabilized Au-Ag alloy nanoparticles for kinetics of aerobic oxidation of benzyl alcohol in aqueous solution. J. Catal. 2013, 301:217-226.
38. Feng Y.H., Yin H.B., Gao D.Z., Wang A.L., Shen L.Q., Meng M.J. Selective oxidation of 1,2-propanediol to lactic acid catalyzed by hydroxylapatite nanorod-supported Au/Pd bimetallic nanoparticles under atmospheric pressure. J. Catal. 2014, 316:67-77.