A direct strategy to synthesize hybrid benzothiazole–carbamate moieties via O-acylation of phenols under metal–organic framework catalysis

Nguyen, Chung Kim; Nguyen, Nguyen B.; Chu, Oanh N.; Dang, Ha V.; Nguyen, Tung T.; Phan, Nam T. S.

doi:10.1039/c7re00067g

Cited by 5 publications

(4 citation statements)

References 42 publications

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“…t BuOOH has been used as an oxidant alongside MOF catalysts previously because MOFs are generally less stable in other peroxides, and it is compatible with both aqueous and organic solvents. [28][29][30] An assigned 1 H NMR spectrum is shown in Figure S3 for reference.…”

Section: Resultsmentioning

confidence: 99%

“…The use of oxygen gas, although more desirable at atmospheric pressure, can lead to significant concerns when pressurised, and especially on industrial scales. t BuOOH has been used as an oxidant alongside MOF catalysts previously because MOFs are generally less stable in other peroxides, and it is compatible with both aqueous and organic solvents [28–30] . An assigned 1 H NMR spectrum is shown in Figure S3 for reference.…”

Section: Resultsmentioning

confidence: 99%

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Oxidation of 5‐Hydroxymethyl Furfural to 2,5‐Furan Dicarboxylic Acid Under Mild Aqueous Conditions Catalysed by MIL‐100(Fe) Metal‐Organic Framework

2022

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We present the use of the redox active MIL-100(Fe) metalorganic framework (MOF) as a catalyst for the oxidation of 5hydroxymethyl furfural (HMF) into 2,5-furan dicarboxylic acid (FDCA) in water. The MOF is synthesised in water alone under mild hydrothermal conditions and 1 H NMR is used to analyse the products of HMF oxidation. The MOF in combination with the co-catalyst TEMPO provides a total selectivity of desired products of 74 % with a maximum FDCA yield of 57 % seen after 24 hours at only 70 °C. The catalyst is recycled ten times with no loss in activity and no evidence of a reduction in the crystallinity of the MOF.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Oxidation of 5‐Hydroxymethyl Furfural to 2,5‐Furan Dicarboxylic Acid Under Mild Aqueous Conditions Catalysed by MIL‐100(Fe) Metal‐Organic Framework

2022

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“…tBuOOH has been favored as an oxidant alongside MOF catalysts in prior studies due to its compatibility with both aqueous and organic solvents, as MOFs are generally less stable in other peroxides. [143] Heating 1.2 mmol of HMF (5 wt %) at 60 °C with tBuOOH and MIL-100(Fe) catalyst resulted in nearly complete HMF consumption (99.8 %) after 72 hours. The total selectivity towards oxidation products peaked at 43 % after 48 hours, with FDCA yield reaching 25 % after 72 hours.…”

Section: Mof Mil-100(fe) Catalyst For Conversion Of 5-hmf To 25-fdcamentioning

confidence: 98%

Catalysts for Biomass Upgrading: Transforming 5‐Hydroxymethyl Furfural into 2,5‐Furan Dicarboxylic Acid for Fine Chemicals, Featuring Mil‐100(Fe) Mof as a Novel Catalyst

Manyepedza,

Makuve

2024

ChemistrySelect

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This review underscores the potential of metal‐organic frameworks (MOFs), exemplified by MIL‐100(Fe), as catalysts in the conversion of 5‐Hydroxymethyl Furfural to 2,5‐Furan Dicarboxylic Acid, which is crucial in bioplastics and value‐added chemical production. MOFs exhibit advantages, including recyclability, stability, and catalytic potential under mild conditions. Despite promising results, MOFs in this application are underexplored compared to traditional metal catalysts. Noble metal catalysts (Au, Pt, and Pd) face challenges such as cost and limited recyclability. Mechanistic studies favor the DFF route, highlighting the oxidation of HMF's hydroxyl group as predominant. Molecular oxygen proves effective for HMF to FDCA transformation, with gold‐based catalysts noted for selectivity. Ongoing industrial efforts by companies like Avantium indicate a shift towards sustainable alternatives. This review highlights research gaps concerning the necessity for custom Metal‐Organic Framework (MOF) catalysts in the transformation of hydroxymethylfurfural (HMF) into 2,5‐furandicarboxylic acid (FDCA). The study recommends, among other things, 1) the adoption of base‐free conversion systems, 2) a focus on large‐scale FDCA manufacturing, prioritizing environmental sustainability despite prevailing cost challenges, and 3) fostering multidisciplinary collaboration. Utilizing advanced engineering software, such as ASPEN HYSYS, is proposed for optimizing these processes and paving the way for the successful industrialization of FDCA in the future.

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“…Over the past few years, carbamate syntheses over several homogeneous and heterogeneous catalysts have been reported, such as Mg 2 Zr x Al 1– x –MMO, 11 Ga 2 O 3 , 12 Mg–Al–Y, 13 Cu-CPO-27, 14 alkali-treated zeolites, 15 Ce–Zn, 16 tungstophosphoric acid (TPA/K30), 17 Mn(OAc) 2 , 18 Pd/ZrO 2 , 19 NaOCH 3 , 20 CuCl 2 /ionic liquids, 21 [BSO 3 HMIm][OTf], 22 Se, 23 AlSBA-15, 24 Zn/SiO 2 , 25 and 3-amino-1,2,4-triazole potassium (KATriz). 26 However, difficulties in homogeneous catalyst separation and low catalytic activity for the heterogeneous catalysts resulted in difficulties in the scale-up process.…”

Section: Introductionmentioning

confidence: 99%

Effective Synthesis of m-Xylylene Dicarbamate via Carbonylation of m-Xylylene Diamine with Ethyl Carbamate over Hierarchical TS-1 Catalysts

et al. 2022

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Carbonylation of m -xylylene diamine (XDA) with ethyl carbamate to produce m -xylylene dicarbamate (XDC), which is the crucial intermediate for the production of m -xylylene diisocyanate (XDI), over the hierarchical TS-1 (HTS-1) zeolite catalyst was studied. The catalysts were characterized by Brunauer–Emmett–Teller, X-ray diffraction, Fourier transform infrared spectroscopy, scanning electron microscopy, and temperature-programed desorption of ammonia techniques systematically. The results showed that the high performance of HTS-1 could be attributed to the weak acidity and high V meso / V total ratio of the catalyst. Impacts of reaction time and reusage on the HTS-1 catalyst were also investigated. Under 6 h and 200 °C, XDA conversion could reach 100% with 88.5% XDC yield. Furthermore, partial loss of Ti active sites with Lewis acidity on the catalyst surface led to the decrease of XDC yield during recycling. Moreover, a possible reaction mechanism for the title reaction was primarily proposed.

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A direct strategy to synthesize hybrid benzothiazole–carbamate moieties via O-acylation of phenols under metal–organic framework catalysis

Abstract: Cu-CPO-27 was used as an efficient recyclable catalyst for the synthesis of benzothiazole–carbamate structures.

Cited by 5 publications

References 42 publications

Oxidation of 5‐Hydroxymethyl Furfural to 2,5‐Furan Dicarboxylic Acid Under Mild Aqueous Conditions Catalysed by MIL‐100(Fe) Metal‐Organic Framework

Oxidation of 5‐Hydroxymethyl Furfural to 2,5‐Furan Dicarboxylic Acid Under Mild Aqueous Conditions Catalysed by MIL‐100(Fe) Metal‐Organic Framework

Catalysts for Biomass Upgrading: Transforming 5‐Hydroxymethyl Furfural into 2,5‐Furan Dicarboxylic Acid for Fine Chemicals, Featuring Mil‐100(Fe) Mof as a Novel Catalyst

Effective Synthesis of m-Xylylene Dicarbamate via Carbonylation of m-Xylylene Diamine with Ethyl Carbamate over Hierarchical TS-1 Catalysts

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