Synthesis, characterization and immobilization of a novel mononuclear vanadium (V) complex on modified magnetic nanoparticles as catalyst for epoxidation of allyl alcohols

Abstract

The 2,4,6‐tris(2‐pyridyl)‐1,3,5‐triazine (tptz) undergoes hydrolysis in the presence of VO(SO4) in an alkaline solution, affording mainly the bis(2‐pyridyl carbonyl)amid) VO2 complex, designated as [VO2(bpca)]. Single‐crystal X‐ray crystallography revealed that the coordination of V in complex is a distorted square‐pyramid coordinated with three nitrogen of bis(2‐pyridyl carbonyl)amid) ligand and two binding oxygen atoms. The prepared complex which successfully supported on modified Fe3O4 nanoparticles using tetraethylorthosilicate (TEOS) and (3‐aminopropyl)trimethoxysilane(APTMS)was designated as Fe3O4@SiO2@APTMS@[VO2(bpca)] complex (nanocatalyst). The complex and nanocatalyst were characterized by means of FT‐IR, XRD, VSM, SEM and TEM. The catalytic activity of [VO2(bpca)] complex and Fe3O4@SiO2@APTMS@complex as catalysts 1 and 2 were evaluated by the epoxidation of geraniol, 3‐methyl‐2‐buten‐1‐ol, trans‐2‐hexen‐1‐ol and 1‐octen‐3‐ol with 70–98% conversions and 95–100% selectivities. Based on the obtained results, the heterogeneity and reusability of the catalyst seems promising. In addition, the in vitro antibacterial activity of [VO2 (bpca)] complex have also been evaluated and compared to the activities of other vanadium complexes, tptz ligand and two standard antibacterial drugs, Nalidixic acid and Vancomycin.

Synthesis of a new schiff base oxovanadium complex with melamine and 2‐hydroxynaphtaldehyde on modified magnetic nanoparticles as catalyst for allyl alcohols and olefins epoxidation

“…Finally, concomitant elimination of tert ‐butanol and epoxide regenerates the catalyst (Scheme ). Since the formation rate of III in the nucleophilic attack of double bond to the oxygen electrophile depends on the number of alkyl substitutions present on the double bonds, it can be concluded that the geraniol which contains a trisubstituted double bonds exhibit the highest epoxidation rate. On the other hand, trans ‐2‐ hexen‐1‐ol and 1‐octen‐3‐ol containing disubstituted and monosubstituted double bonds would undergo epoxidation reactions in lower rates, respectively.…”

“…Finally, comparison of the epoxidation results of geraniol catalyzed by Fe 3 O 4 @SiO 2 @CPTMS@‐Mel‐Naph‐VOcomplex in this work with some previously reported heterogeneous catalysts provided in Table reveals that conversion, selectivity, TON and TOF of our catalysis system is considerable …”

“…Moreover, to modify the stabilization and recycling ability of the homogeneous catalysis systems, they have been immobilized onto the solid supports. Various organic polymers and inorganic materials such as silica, MCM‐41, SBA‐15, zeolites and magnetic nanoparticles have been used as support in heterogeneous catalysis systems. Among them, Fe 3 O 4 magnetic nanoparticles have attracted great interest because of low cost, high surface area, low toxicity and easily separation by applying an external magnetic field .…”

Theoretical Studies of the Zeolite-Y Encapsulated Chlorine-Substituted Copper(II)phthalocyanine Complex on the Formation Glycidol from Allyl Alcohol

“…30−32 The allyl alcohol epoxidation is a big challenge in the industrial point of view because of their wide range of applications in the field of organic synthesis and pharmaceuticals. 33−38 Allyl alcohol undergoes epoxidation and gives glycidol. Glycidol is used as an oil additive, precursor, and stabilizer for the synthesis of novel polymers.…”

Synthesis of bioactive magnetic nanoparticles spiro[indoline‐3,4′‐[1,3]dithiine]@Ni (NO3)2 supported on Fe3O4@SiO2@CPS as reusable nanocatalyst for the synthesis of functionalized 3,4‐dihydro‐2H‐pyran

“…Fe 3 O 4 coated as a magnet core and supported by organic compounds has found a special place in the synthesis of heterogeneous magnetic nanocatalysts as such many relevant studies have been carried out in this regard . In addition, Fe 3 O 4 supported and coated can create complexes with different metals and synthesized magnetic organometallic nanocatalysts . A review of the literature also elaborates on the use of nickel metal in the synthesis of organic compounds .…”