Transfer hydrogenation of nitroarenes using cellulose filter paper-supported Pd/C by filtration as well as sealed methods

被引:12
作者
Bokov, Dmitry Olegovich [1 ]
Mahmoud, Mustafa Z. [2 ,3 ]
Widjaja, Gunawan [4 ,5 ]
Suksatan, Wanich [6 ]
Chupradit, Supat [7 ]
Altimari, Usama S. [8 ]
Hussein, Hussein Ali [9 ]
Mustafa, Yasser Fakri [10 ]
Kazemnejadi, Milad [11 ]
机构
[1] Sechenov First Moscow State Med Univ, Inst Pharm, 8 Trubetskaya St,Bldg 2, Moscow 119991, Russia
[2] Prince Sattam Bin Abdulaziz Univ, Coll Appl Med Sci, Dept Radiol & Med Imaging, Al Kharj 11942, Saudi Arabia
[3] Univ Canberra, Fac Hlth, Canberra, ACT, Australia
[4] Univ Krisnadwipayana, Postgrad Study, Bekasi, Indonesia
[5] Univ Indonesia, Fac Publ Hlth, Depok, Indonesia
[6] Chulabhorn Royal Acad, HRH Princess Chulabhorn Coll Med Sci, Fac Nursing, Bangkok, Thailand
[7] Chiang Mai Univ, Fac Associated Med Sci, Dept Occupat Therapy, Chiang Mai 50200, Thailand
[8] Al Nisour Univ Coll, Baghdad, Iraq
[9] Al Ayen Univ, Sci Res Ctr, Thi Qar, Iraq
[10] Univ Mosul, Coll Pharm, Dept Pharmaceut Chem, Mosul 41001, Iraq
[11] Shiraz Univ, Coll Sci, Dept Chem, Shiraz 7194684795, Iran
关键词
EX-SITU GENERATION; NITRO-COMPOUNDS; PALLADIUM NANOPARTICLES; CATALYTIC-REDUCTION; EFFICIENT REDUCTION; CHEMICAL-PROPERTIES; HYDRAZINE HYDRATE; AMMONIUM FORMATE; WATER-ADSORPTION; DIP-CATALYST;
D O I
10.1039/d2ra01151d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A reductive filter paper for selective nitro reduction has been prepared by modification of a pristine cellulose filter paper by Pd/C nanoparticles, as a portable catalyst. The reaction was performed in two different set-ups including (i) filtration and (ii) sealed systems, in the presence of ammonium formate and ex situ generated hydrogen gas reducing agents, respectively. In the sealed system in the presence of H-2 gas, the halogenated nitroarenes were completely reduced, while in the filtration system, different derivatives of the nitroarenes were selectively reduced to aryl amines. In both systems, the reduction of nitroarenes to aryl amines was performed with high efficiency and selectivity, comparable to a heterogeneous system. Reaction parameters were comprehensively designed using Design Expert software and then studied. The properties of the catalytic filter paper were studied in detail from the points of view of swellability, shrinkage, reusability, and stability against acidic, alkaline, and oxidative reagents.
引用
收藏
页码:10933 / 10949
页数:17
相关论文
共 70 条
[1]   Transfer hydrogenation of aromatic nitro compounds using polymer-supported formate and Pd-C [J].
Abiraj, K ;
Srinivasa, GR ;
Gowda, DC .
SYNTHETIC COMMUNICATIONS, 2005, 35 (02) :223-230
[2]   Nitroarene reduction: a trusted model reaction to test nanoparticle catalysts [J].
Aditya, Teresa ;
Pal, Anjali ;
Pal, Tarasankar .
CHEMICAL COMMUNICATIONS, 2015, 51 (46) :9410-9431
[3]   An efficient and easily retrievable dip catalyst based on silver nanoparticles/chitosan-coated cellulose filter paper [J].
Ahmad, Ikram ;
Kamal, Tahseen ;
Khan, Sher Bahadar ;
Asiri, Abdullah M. .
CELLULOSE, 2016, 23 (06) :3577-3588
[4]   NiFe2O4@SiO2@ZrO2/SO42-/Cu/Co nanoparticles: a novel, efficient, magnetically recyclable and bimetallic catalyst for Pd-free Suzuki, Heck and C-N cross-coupling reactions in aqueous media [J].
Alavi, Seyyedeh Ameneh G. ;
Nasseri, Mohammad Ali ;
Kazemnejadi, Milad ;
Allahresani, Ali ;
HussainZadeh, Mandi .
NEW JOURNAL OF CHEMISTRY, 2021, 45 (17) :7741-7757
[5]   Alternative catalytic materials: carbides, nitrides, phosphides and amorphous boron alloys [J].
Alexander, Anne-Marie ;
Hargreaves, Justin S. J. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (11) :4388-4401
[6]   Reduction of aromatic and aliphatic nitro groups to anilines and amines with hypophosphites associated with Pd/C [J].
Baron, Marc ;
Metay, Estelle ;
Lemaire, Marc ;
Popowycz, Florence .
GREEN CHEMISTRY, 2013, 15 (04) :1006-1015
[7]   Catalytic transfer reduction of conjugated alkenes and an imine using polymer-supported formates [J].
Basu, B ;
Bhuiyan, MH ;
Das, P ;
Hossain, I .
TETRAHEDRON LETTERS, 2003, 44 (50) :8931-8934
[8]   Preparation and characterization of activated carbon from date stones by physical activation with steam [J].
Bouchelta, Chafia ;
Medjram, Mohamed Salah ;
Bertrand, Odile ;
Bellat, Jean-Pierre .
JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS, 2008, 82 (01) :70-77
[9]   One-pot reductive mono-N-alkylation of aniline and nitroarene derivatives using aldehydes [J].
Byun, Eunyoung ;
Hong, Bomi ;
De Castro, Kathlia A. ;
Lim, Minkyung ;
Rhee, Hakjune .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (25) :9815-9817
[10]   One-pot synthesis of flowerlike Ni7S6 and its application in selective hydrogenation of chloronitrobenzene [J].
Cao, Feng ;
Liu, Ruixia ;
Zhou, Liang ;
Song, ShuYan ;
Lei, YongQian ;
Shi, WeiDong ;
Zhao, Fengyu ;
Zhang, Hongjie .
JOURNAL OF MATERIALS CHEMISTRY, 2010, 20 (06) :1078-1085