Catalytic oxidation of cyclohexane using transition metal complexes of dithiocarbazate Schiff base

被引:73
作者
Alshaheri, Ali Ahmed [1 ]
Tahir, Mohamed Ibrahim Mohamed [1 ]
Rahman, Mohd Basyaruddin Abdul [1 ]
Ravoof, Thahira B. S. A. [1 ]
Saleh, Tawfik A. [2 ]
机构
[1] Univ Putra Malaysia, Dept Chem, Fac Sci, Upm Serdang 43400, Selangor, Malaysia
[2] King Fahd Univ Petr & Minerals, Dept Chem, Dhahran, Saudi Arabia
关键词
Dithiocarbazate Schiff bases; Metal complexes; Cyclohexane; Oxidation; Selectivity; C-H BONDS; IRON; DESULFURIZATION; PEROXIDE; VANADIUM; LIGAND; COPPER;
D O I
10.1016/j.cej.2017.06.116
中图分类号
X [环境科学、安全科学];
学科分类号
08 ; 0830 ;
摘要
Metal complexes of dithiocarbazate Schiff bases (abbreviated as NiSMdiAP, CoSMdiAP, FeSMdiAP, MnSMdiAP and ZnSMdiAP, where SMdiAP represents the Schiff base) were synthesized and characterized using techniques including Fourier transform infrared spectroscopy, nuclear magnetic resonance, H-1 NMR, C-13 NMR, magnetic susceptibility measurements, molar conductivity, ultraviolet-visible spectroscopy, and inductively coupled plasma-optical emission spectrometry. The study focused on the oxidation of cyclohexane by using the metal complexes as catalysts with hydrogen peroxide as the oxidative source under special conditions. These catalysts showed good conversion and high selectivity compared to other Schiff base complexes. The conditions of the oxidation reaction catalysed by these complexes were investigated. Gas chromatography was used to analyse the products of the oxidation reaction of cyclohexane and it showed that cyclohexanol and cyclohexanone are the main products. A copper complex of Schiff base formed from 2,6-diacetyl pyridine and S-methyldithiocarbazate, [CuIISMdiAP] showed the highest level of activity during the screening studies towards cyclohexane oxidation. The time of reaction, temperature, and the concentration of H2O2 as an environmentally friendly oxidant and the catalyst type played an important role in the selectivity and conversion of cyclohexane oxidation. The selectivity of the reaction was 98%. (C) 2017 Elsevier B.V. All rights reserved.
引用
收藏
页码:423 / 430
页数:8
相关论文
共 43 条
[1]   A new manganese(III) complex anchored onto SBA-15 as efficient catalyst for selective oxidation of cycloalkanes and cyclohexene with hydrogen peroxide [J].
Alavi, Sohaila ;
Hosseini-Monfared, Hassan ;
Siczek, Milosz .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2013, 377 :16-28
[2]   Synthesis, characterisation and catalytic activity of dithiocarbazate Schiff base complexes in oxidation of cyclohexane [J].
Alshaheri, Ali Ahmed ;
Tahir, Mohamed Ibrahim Mohamed ;
Rahman, Mohd Basyaruddin Abdul ;
Begum, Thahira ;
Saleh, Tawfik A. .
JOURNAL OF MOLECULAR LIQUIDS, 2017, 240 :486-496
[3]  
[Anonymous], 2009, Angew. Chem. Int. Ed, DOI DOI 10.1002/ANGE.200802672
[4]   Organic-inorganic hybrid catalysts containing new Schiff base for environment friendly cyclohexane oxidation [J].
Antony, R. ;
Manickam, S. Theodore David ;
Karuppasamy, K. ;
Kollu, Pratap ;
Chandrasekar, P. V. ;
Balakumar, S. .
RSC ADVANCES, 2014, 4 (81) :42816-42824
[5]   Synthesis, spectroscopy and thermal behavior of new lead(II) complexes derived from S-methyl/benzyldithiocarbazates (SMDTC/SBDTC): X-ray crystal structure of [Pb(SMDTC)(NO3)2] [J].
Bera, Pulakesh ;
Kim, Chong-Hyeak ;
Seok, Sang Il .
INORGANICA CHIMICA ACTA, 2009, 362 (08) :2603-2608
[6]   Oxo-transfer catalysis from t-BuOOH with C-H bond insertion using tridentate Schiff-base-chelate complexes of ruthenium(III) [J].
Chatterjee, D ;
Mitra, A ;
Shepherd, RE .
INORGANICA CHIMICA ACTA, 2004, 357 (04) :980-990
[7]   ASPECTS OF METHANE CHEMISTRY [J].
CRABTREE, RH .
CHEMICAL REVIEWS, 1995, 95 (04) :987-1007
[8]   Response surface methodology optimization of adsorptive desulfurization on nickel/activated carbon [J].
Danmaliki, Gaddafi I. ;
Saleh, Tawfik A. ;
Shamsuddeen, Abdullahi A. .
CHEMICAL ENGINEERING JOURNAL, 2017, 313 :993-1003
[9]   Effects of bimetallic Ce/Fe nanoparticles on the desulfurization of thiophenes using activated carbon [J].
Danmaliki, Gaddafi I. ;
Saleh, Tawfik A. .
CHEMICAL ENGINEERING JOURNAL, 2017, 307 :914-927
[10]   Selective oxidation of cyclohexane with hydrogen peroxide in the presence of copper pyrophosphate [J].
Du, Ying ;
Xiong, Yonglian ;
Li, Jing ;
Yang, Xiangguang .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2009, 298 (1-2) :12-16