Oxo-vanadium(IV) unsymmetrical Schiff base complex immobilized on γ-Fe2O3 nanoparticles: A novel and magnetically recoverable nanocatalyst for selective oxidation of sulfides and oxidative coupling of thiols

被引:16
作者
Mahdian, Abolfazl [1 ]
Ardakani, Mehdi Hatefi [1 ]
Heydari-Bafrooei, Esmaeil [1 ]
Saeednia, Samira [1 ]
机构
[1] Vali E Asr Univ Rafsanjan, Dept Chem, Fac Sci, Rafsanjan 7718897111, Iran
关键词
magnetic nanocatalyst; oxo-vanadium(IV) complex; sulfide; thiol; gamma-Fe2O3; nanoparticle; CRYSTAL-STRUCTURE;
D O I
10.1002/aoc.6170
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
In this research, an unsymmetrical salen-type oxo-vanadium(IV) complex, [VO(salenac-OH)] (salenac-OH = [9-(2 ',4 '-dihydroxyphenyl)-5,8-diaza-4-methylnona-2,4,8-trienato](-2)), was synthesized and covalently immobilized on the surface of magnetic gamma-Fe2O3 nanoparticles. The resulting gamma-Fe2O3@[VO(salenac-OH)] nanoparticles were characterized by several techniques including Fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD), scanning and transmission electron microscopies (SEM and TEM), energy-dispersive X-ray (EDX) spectroscopy, vibrating sample magnetometry (VSM), thermal gravimetric analysis (TGA), inductively coupled plasma (ICP), and elemental analysis. The prepared gamma-Fe2O3@[VO(salenac-OH)] nanoparticle was utilized as an efficient catalyst for selective oxidation of sulfides to sulfoxides using 30% H2O2 as oxidant and oxidative coupling of thiols into disulfides with urea/H2O2 (UHP) as an oxidizing reagent. The products were achieved with good to excellent yields at room temperature with no over-oxidation of sulfoxides and disulfides to unexpected by-products. This catalyst can be magnetically recovered by applying an external magnet and reused for five continuous cycles in both oxidation reactions without a significant loss in its catalytic activity. Furthermore, the FT-IR spectrum and XRD pattern of the recovered catalyst showed no critical change to those of the fresh one.
引用
收藏
页数:16
相关论文
共 53 条
[1]   Preparation of a novel, efficient, and recyclable magnetic catalyst, γ-Fe2O3@HAp-Ag nanoparticles, and a solvent- and halogen-free protocol for the synthesis of coumarin derivatives [J].
Abbasi, Zahra ;
Rezayati, Sobhan ;
Bagheri, Maryam ;
Hajinasiri, Rahimeh .
CHINESE CHEMICAL LETTERS, 2017, 28 (01) :75-82
[2]  
Amini I., 2020, ASIAN J GREEN CHEM, V4, P51
[3]   A magnetically recoverable γ-Fe2O3 nanocatalyst for the synthesis of 2-phenylquinazolines under solvent-free conditions [J].
Anand, Narani ;
Reddy, Kannapu Hari Prasad ;
Satyanarayana, Tirumalasetty ;
Rao, Kamaraju Seetha Rama ;
Burri, David Raju .
CATALYSIS SCIENCE & TECHNOLOGY, 2012, 2 (03) :570-574
[4]   Synthesis, characterization and catalytic activity of supported vanadium Schiff base complex as a magnetically recoverable nanocatalyst in epoxidation of alkenes and oxidation of sulfides [J].
Bagherzadeh, Mojtaba ;
Bahjati, Mohammad ;
Mortazavi-Manesh, Anahita .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2019, 897 :200-206
[5]   Mn(III) complex supported on Fe3O4 nanoparticles: magnetically separable nanocatalyst for selective oxidation of thiols to disulfides [J].
Bagherzadeh, Mojtaba ;
Haghdoost, Mohammad Mehdi ;
Moghaddam, Firouz Matloubi ;
Foroushani, Behzad Koushki ;
Saryazdi, Setareh ;
Payab, Ebrahim .
JOURNAL OF COORDINATION CHEMISTRY, 2013, 66 (17) :3025-3036
[6]   Nanoparticle supported, magnetically separable vanadium complex as catalyst for selective oxidation of sulfides [J].
Bagherzadeh, Mojtaba ;
Haghdoost, Mohammad Mehdi ;
Shahbazirad, Ayoob .
JOURNAL OF COORDINATION CHEMISTRY, 2012, 65 (04) :591-601
[7]   Vanadium-Schiff base complex covalently bonded on modified MCM-41 as catalyst for asymmetric oxidation of methyl phenyl sulfide [J].
Ben Zid, T. ;
Khedher, I. ;
Ksibi, Z. ;
Fraile, J. M. .
JOURNAL OF POROUS MATERIALS, 2016, 23 (02) :507-516
[8]   Use of Cu(II)-di-Schiff bases as metalloligands in the formation of complexes with Cu(II), Ni(II) and Zn(II) perchlorate [J].
Biswas, Saptarshi ;
Ghosh, Ashutosh .
POLYHEDRON, 2013, 65 :322-331
[9]   An efficient and convenient method for preparation of disulfides from thiols using air as oxidant catalyzed by Co-Salophen [J].
Chai, Pin Ji ;
Li, Yong Shu ;
Tan, Cheng Xia .
CHINESE CHEMICAL LETTERS, 2011, 22 (12) :1403-1406
[10]   Reusable cobalt-phthalocyanine in water: efficient catalytic aerobic oxidative coupling of thiols to construct S-N/S-S bonds [J].
Dou, Yingchao ;
Huang, Xin ;
Wang, Hao ;
Yang, Liting ;
Li, Heng ;
Yuan, Bingxin ;
Yang, Guanyu .
GREEN CHEMISTRY, 2017, 19 (11) :2491-2495