Abstract
Immobilization of organometallic catalyst were attempted by using cyclodextrin-based metal-organic framework (CD-MOF) with the characteristic nanoporous structure. Water-soluble Co(II)TCPP was prepared as an organometallic catalyst and introduced into hydrophilic nanopores in CD-MOF by co-crystallization method. In order to evaluate the catalytic properties of the obtained Co(II)TCPP/CDMOF, the oxidative coupling reaction of creosol was performed. At a catalyst concentration of 0.2 mol%, the catalytic activity of the heterogeneous Co(II)TCPP/CDMOF catalyst was almost the same as that of the homogeneous Co(II)TCPP catalyst. The conversion for Co(II)TCPP/CD-MOF catalyst reached 92% after 2-hour reaction.
Highlights
Organometallic catalysts have been used as homogeneous catalyst in the fields of fine chemical and pharmaceutical industries [1]
Jiang et al [11] performed a creosol coupling reaction using meso-tetra (4methoxyphenyl) porphyrin cobalt (II) [T(p-OMe )PPCo] and stated the conversion of 99% and the yield of 98% after 15 hours reaction under the same experimental conditions. These results indicates that Co(II)TCPP shows almost the same catalytic activity as T(p-OMe)PPCo
Co(II)TCPP could be introduced into the hydrophilic nanopore in cyclodextrin-based metal-organic framework (CD-MOF) crystal by cocrystallization method
Summary
Organometallic catalysts have been used as homogeneous catalyst in the fields of fine chemical and pharmaceutical industries [1]. In the previous paper [4], we succeeded in preparing the CD-MOF in which water-soluble porphyrin (tetrakis (4carboxyphenyl) porphyrin, TCPP) was encapsulated in hydrophilic nanopores by methanol vapour diffusion of methanol to the mixed solution of γCD, KOH and TCPP. The synthesized Co(II)TCPP was added to the γ-CD and KOH solution and Co(II)TCPP/CD-MOF was crystallized by vapor diffusion of methanol. This Co(II)TCPP/CDMOF was used as a heterogeneous catalyst to perform the coupling reaction of 2-methoxy4methylphenol (creosol), and its catalytic activity was investigated. The oxidative coupling of creosol was carried out by using homogeneous Co(II)TCPP or heterogeneous Co(II)TCPP/CD-MOF catalyst in methanol (Scheme 1). HPLC (Shimadzu Corp.) with a reverse phase column (InertSustainTM AQ-C18, GL Sciences Inc.) was used for the analysis of the coupling reaction products
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