Sn-Based Porous Coordination Polymer Synthesized with Two Ligands for Tandem Catalysis Producing 5-Hydroxymethylfurfural

Lutong Jiao,Siyu Sun,Xianling Meng,Peijun Ji

doi:10.3390/catal9090739

Lutong Jiao, Siyu Sun + Show 2 more

Open Access

https://doi.org/10.3390/catal9090739

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Abstract

5-Hydroxymethylfurfural (HMF) is a biomass-derived important platform compound. Developing an efficient catalyst for producing HMF from a biomass source is important. Herein, using the ligands 5-sulfoisophthalic acid (SPA) and imidazole (Imd), a tin-based porous coordination polymer was synthesized, namely SPA-Imd-TinPCP. This novel material possesses a multifunctional catalysis capability. The coordinated tin (IV) can catalyze the isomerization of glucose to fructose. The ligand imidazole, as an additional base site, can catalyze glucose isomerization. The sulfonic group of the ligand SPA can catalyze the dehydration of fructose to HMF. SPA-Imd-TinPCP was used as a catalyst for the conversion of glucose to HMF. HMF yields of 59.5% in dimethyl sulfoxide (DMSO) and 49.8% in the biphasic solvent of water/tetrahydrofuran were obtained. Consecutive use of SPA-Imd-TinPCP demonstrated that, after reusing it five times, there was no significant activity loss in terms of the glucose conversion and HMF yield.

Highlights

The X-ray diffraction (XRD) pattern (Figure 1b) shows intense broad diffraction peaks corresponding to a polymorph made up of partial crystals
The X-ray diffraction (XRD) pattern is in accordance with the transmission electron microscope (TEM) image
The spectra of Energy-disperse spectroscopy (EDS) (Figure 2a) and X-ray photoelectron spectroscopy (XPS) (Figure 2b) show that peaks corresponding to the elements C, O, S, N, and Sn appeared

Summary

Characterization of SPA-Imd-TinPCP

A transmission electron microscope (TEM) image (Figure 1a) shows that SPA-Imd-TinPCP is a polymorph made up of partial crystals. The X-ray diffraction (XRD) pattern (Figure 1b) shows intense broad diffraction peaks corresponding to a polymorph made up of partial crystals. Catalysts 2019, 9, x FOR PEER REVIEW CCaattaallyyssttss22001199,,99,, x73F9OR PEER REVIEW. FFrruuccttoossee ccoonnvveerrssiioonn aanndd HHMMFF yyiieelldd uunnddeerrtthhee ccaattaallyyssiissooff SSPPAA--IImmdd--TTiinnPPCCPP iinn DDMMSSOO ((aa)) aanndd HH2OO//TTHHFF ((vv//vv 11::44)) ((bb)). TThhee wwoorrkkiinngg pprreessssuurreess wweerree 11 aattmm aanndd 55 aattmm ffoorr DDMMSSOO aanndd HH22OO//TTHHFF ssyysstteemmss,, rreessppeeccttiivveellyy Two reaction media were used for the conversion of glucose to HMF under the catalysis of SPA-TImwdo-rTeiancPtCioPn. mFiegduiraew10eareshuosewdsftohrethreescuolntsvienrsDioMn SoOf g. SCyonmthpeasriesdtewmiptherathtuerere(p1o0r0te◦dC)c, aataslyynsth, eSsPisAp-Irmocde-sTsinfrPeCePofshyodwreodfluaodrvicanatcaigde, sanindccluadlciinngaticoantaslyntoict bsteaibniglintye,eadelodw. er synthesis temperature (100 °C), a synthesis process free of hydrofluoric acid, and calcinations not being needed

Experimental Section

Characterization and Measurement

Conversion of Glucose to HMF

Substrate and Product Analysis

Reuse of Catalyst

Conclusions