Chiral MnIII(Salen) supported on tunable phenoxyl group modified zirconium poly (styrene-phenylvinylphosphonate)-phosphate as an efficient catalyst for epoxidation of unfunctionalized olefins

邹晓川,; 石开云,; 王存,

doi:10.1016/s1872-2067(14)60064-4

Cited by 15 publications

(7 citation statements)

References 34 publications

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“…Moreover, the immobilized catalysts could be reused at least 10 times without significant loss of activity and enantioselectivity. Furthermore, a point worth emphasizing is that ZPS-PVPA-based catalyst results in remarkable increase of conversion and ee values in the absence of expensive O-coordinating axial additive for the asymmetric epoxidation of olefins [23,24], which is exactly opposite to the literature reported earlier for both homogeneous and heterogeneous systems [25,26]. This novel additive effect was mainly attributed to the support ZPS-PVPA and the axial phenoxyl linker group.…”

Section: Introductionmentioning

confidence: 70%

Chiral MnIII (Salen) Covalently Bonded on Modified ZPS-PVPA and ZPS-IPPA as Efficient Catalysts for Enantioselective Epoxidation of Unfunctionalized Olefins

Zou

Wang

et al. 2017

Polymers

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Chiral Mn III (salen) complex supported on modified ZPS-PVPA (zirconium poly(styrenephenylvinylphosphonate)) and ZPS-IPPA (zirconium poly(styrene-isopropenyl phosphonate)) were prepared using -CH 2 Cl as a reactive surface modifier by a covalent grafting method. The supported catalysts showed higher chiral induction (ee: 72%-83%) compared with the corresponding homogeneous catalyst (ee: 54%) for asymmetric epoxidation of α-methylstrene in the presence of 4-phenylpyridine N-oxide (PPNO) as axial base using NaClO as an oxidant. ZPS-PVPA-based catalyst 1, with a larger pore diameter and surface area, was found to be more active than ZPS-IPPA-based catalyst 2. In addition, bulkier alkene-like indene, was efficiently epoxidized with these supported catalysts (ee: 96%-99%), the results were much higher than those for the homogeneous system (ee: 65%). Moreover, the prepared catalysts were relatively stable and can be recycled at least eight times without significant loss of activity and enantioselectivity.

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Section: Introductionmentioning

confidence: 70%

Chiral MnIII (Salen) Covalently Bonded on Modified ZPS-PVPA and ZPS-IPPA as Efficient Catalysts for Enantioselective Epoxidation of Unfunctionalized Olefins

Zou

Wang

et al. 2017

Polymers

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“…Zirconyl chloride octahydrate, γ-propyl mercaptotrimethoxysilane (MPTMS), tert-butyl hydroperoxide (TBHP, 65%, wt%), and benzoyl peroxide (BPO) were supplied by Alfa Aesar (Tianjian, China). The 1-phenylvinyl phosphonic acid (PVPA) was prepared according to literature [22] and its structures were confirmed by 1 H NMR, 31 P NMR, and FT-IR. 1 H NMR (CDCl3):6.06 (d, 1H), 6.23 (d, 1H), 7.26-7.33 (m, 3H), 7.48 (m, 2H).…”

Section: Methodsmentioning

confidence: 99%

“…The synthesis and characterization of ZPS-PVPA (Scheme 1) has been reported earlier by our group [22].…”

Section: Synthesis Of Zirconium Poly(styrene-phenylvinyl-phosphonate)mentioning

confidence: 99%

Synthesis of Sulfonic Acid-Functionalized Zirconium Poly(Styrene-Phenylvinyl-Phosphonate)-Phosphate for Heterogeneous Epoxidation of Soybean Oil

et al. 2019

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In this paper, a solid acid catalyst (ZPS–PVPA–SO3H) was prepared by anchoring thiol group on zirconium poly(styrene-phenylvinyl-phosphonate)-phosphate (ZPS–PVPA), followed by oxidation of thiol groups to obtain sulfonic acid groups. The solid acid catalyst was characterized by XPS, X-ray, EDS, SEM, and TG-DSC. The successful preparation of sulfonic acid-functionalized ZPS–PVPA was confirmed. Subsequently, the catalytic performance of ZPS–PVPA–SO3H was investigated in the epoxidation of soybean oil. The results demonstrated that ZPS–PVPA–SO3H can effectively catalyze epoxidation of soybean oil with TBHP as an oxidant. Moreover, there was no significant decrease in catalytic activity after 5 repeated uses of the ZPS–PVPA–SO3H. Interestingly, the ZPS–PVPA–SO3H was kept in 2 mol/L of HCl overnight after the end of the seventh reaction, and the catalytic activity was gradually restored during the eighth to tenth cycles.

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“…Heterogeneity of homogeneous catalysts is an important strategy to enable the reuse of expensive chiral catalysts and large-scale synthesis [3]. Common catalytic carrier materials include organic polymer, inorganic solidseries, and organic polystyrene/inorganic hydrogen phosphate (Zr, Al, Zn, Ca) [4][5][6][7][8][9][10][11][12][13][14][15]. Unfortunately, immobilized catalysts still have some deficiencies such as low catalytic efficiency and poor reusability.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of GO-SalenMn and Asymmetric Catalytic Olefin Epoxidation

et al. 2019

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Graphene oxide (GO) was used as a catalyst carrier, and after the hydroxyl group in GO was modified by 3-aminopropyltrimethoxysilane (MPTMS), axial coordination and immobilization with homogeneous chiral salenMnCl catalyst were carried out. The immobilized catalysts were characterized in detail by FT–IR, TG–DSC, XPS, EDS, SEM, X-ray, and AAS, and the successful preparation of GO-salenMn was confirmed. Subsequently, the catalytic performance of GO-salenMn for asymmetric epoxidation of α-methyl-styrene, styrene, and indene was examined, and it was observed that GO-salenMn could efficiently catalyze the epoxidation of olefins under an m-CPBA/NMO oxidation system. In addition, α-methyl-styrene was used as a substrate to investigate the recycling performance of GO-salenMn. After repeated use for three times, the catalytic activity and enantioselectivity did not significantly change, and the conversion was still greater than 99%. As the number of cycles increased, the enantioselectivity and chemoselectivity gradually decreased, but even after 10 cycles, the enantiomeric excess was 52%, which was higher than that of the homogeneous counterpart under the same conditions. However, compared to fresh catalysts, the yield decreased from 96.9 to 55.6%.

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Chiral MnIII(Salen) supported on tunable phenoxyl group modified zirconium poly (styrene-phenylvinylphosphonate)-phosphate as an efficient catalyst for epoxidation of unfunctionalized olefins

Cited by 15 publications

References 34 publications

Chiral MnIII (Salen) Covalently Bonded on Modified ZPS-PVPA and ZPS-IPPA as Efficient Catalysts for Enantioselective Epoxidation of Unfunctionalized Olefins

Chiral MnIII (Salen) Covalently Bonded on Modified ZPS-PVPA and ZPS-IPPA as Efficient Catalysts for Enantioselective Epoxidation of Unfunctionalized Olefins

Synthesis of Sulfonic Acid-Functionalized Zirconium Poly(Styrene-Phenylvinyl-Phosphonate)-Phosphate for Heterogeneous Epoxidation of Soybean Oil

Synthesis of GO-SalenMn and Asymmetric Catalytic Olefin Epoxidation

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