Base-free conversion of glycerol to methyl lactate using a multifunctional catalytic system consisting of Au–Pd nanoparticles on carbon nanotubes and Sn-MCM-41-XS

Tang, Zhenchen; Boer, Dina G.; Syari’ati, Ali; Enache, Mihaela; Rudolf, Petra; Heeres, Hero J.; Pescarmona, Paolo P.

doi:10.1039/c9gc01521c

Cited by 20 publications

(25 citation statements)

References 54 publications

(98 reference statements)

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“…[88] (CC BY-NC 4.0) are more acidic than the respective base, and the ratios of the amounts of the different oxygen-containing FG can then be calculated directly from the base consumption. Boehm titration has been utilized to characterize the FG on different kinds of CNT [106][107][108] as well as on other carbon-based materials like ozone-treated nanodiamonds, carbon NP derived from organic resin, graphite-decorated MnFe 2 O 4 nanocomposites, and natural char nano-and microparticles [109][110][111][112]. To evaluate and standardize Boehm titration regarding accuracy, robustness, repeatability, and precision, Schönherr et al investigated the FG on oxidized multi-walled CNT using different reaction bases, treatment times, and amounts of carbon material [105,113].…”

Section: Boehm Titrationmentioning

confidence: 99%

Analyzing the surface of functional nanomaterials—how to quantify the total and derivatizable number of functional groups and ligands

et al. 2021

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Functional nanomaterials (NM) of different size, shape, chemical composition, and surface chemistry are of increasing relevance for many key technologies of the twenty-first century. This includes polymer and silica or silica-coated nanoparticles (NP) with covalently bound surface groups, semiconductor quantum dots (QD), metal and metal oxide NP, and lanthanide-based NP with coordinatively or electrostatically bound ligands, as well as surface-coated nanostructures like micellar encapsulated NP. The surface chemistry can significantly affect the physicochemical properties of NM, their charge, their processability and performance, as well as their impact on human health and the environment. Thus, analytical methods for the characterization of NM surface chemistry regarding chemical identification, quantification, and accessibility of functional groups (FG) and surface ligands bearing such FG are of increasing importance for quality control of NM synthesis up to nanosafety. Here, we provide an overview of analytical methods for FG analysis and quantification with special emphasis on bioanalytically relevant FG broadly utilized for the covalent attachment of biomolecules like proteins, peptides, and oligonucleotides and address method- and material-related challenges and limitations. Analytical techniques reviewed include electrochemical titration methods, optical assays, nuclear magnetic resonance and vibrational spectroscopy, as well as X-ray based and thermal analysis methods, covering the last 5–10 years. Criteria for method classification and evaluation include the need for a signal-generating label, provision of either the total or derivatizable number of FG, need for expensive instrumentation, and suitability for process and production control during NM synthesis and functionalization. Graphical abstract

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Section: Boehm Titrationmentioning

confidence: 99%

Analyzing the surface of functional nanomaterials—how to quantify the total and derivatizable number of functional groups and ligands

et al. 2021

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“…Partial oxidation of glycerol into trioses (i.e., 1,3-dihydroxyacetone (DHA) and glyceraldehyde (GLAD)) is an attractive catalytic route for the valorization of this compound. Further catalytic conversion of trioses in the presence of alcohols yields the biodegradable alkyl lactates (Scheme 1), which can be employed as green solvents with a wide range of applications [7]. Several catalysts have been reported for this last step, with heterogeneous ones being the preferred option in view of potential industrial application [8][9][10].…”

Section: Introductionmentioning

confidence: 99%

“…Several catalysts have been reported for this last step, with heterogeneous ones being the preferred option in view of potential industrial application [8][9][10]. Typically, the heterogeneous catalysts displaying high activity and selectivity for this reaction contain (mild) Brønsted acid sites for catalyzing the dehydration of dihydroxyacetone or glyceraldehyde to the pyruvic aldehyde intermediate, and Lewis acid sites that promote the subsequent rearrangement with formation of methyl lactate (see Scheme 1) [7,11]. Particularly promising results were obtained with catalysts in which Sn atoms in tetrahedral coordination in a silicate matrix act as the Lewis acids sites, as in Sn-containing zeolites and ordered mesoporous silicates such as Sn-MCM-41 and Sn-SBA-15 [12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

“…If a suitable Sn-containing silicate is combined with a catalyst that is able to promote the dehydrogenative oxidation of glycerol to either dihydroxyacetone or glyceraldehyde, the one-pot conversion of glycerol to methyl lactate (Scheme 1) can be achieved. Indeed, supported metal nanoparticles (e.g., Au, Pd and alloys) have been employed in combination with nanosized Sn-MCM-41 to convert glycerol with high selectivity towards methyl lactate (87% selectivity at 81% glycerol conversion after 4.5 h reaction at 140 • C under 30 bar air) [7]. However, all the heterogeneous catalysts mentioned above were prepared and used in powder format.…”

Section: Introductionmentioning

confidence: 99%

“…Catalytic route from glycerol to methyl lactate (ML) in the presence of methanol (in black). The possible by-products are shown in grey [7,14].…”

Section: Introductionmentioning

confidence: 99%

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Bimetallic Zeolite Beta Beads with Hierarchical Porosity as Brønsted-Lewis Solid Acid Catalysts for the Synthesis of Methyl Lactate

et al. 2021

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Bimetallic zeolite Beta in bead format and containing Al sites with Brønsted acid behavior and Sn, Zr or Hf sites with Lewis acid character, were prepared using a two-step synthetic route. First, zeolite Beta in the format of macroscopic beads (400 to 840 μm) with hierarchical porosity (micropores accessed through meso- and macropores in the range of 30 to 150 nm) were synthesized by hydrothermal crystallization in the presence of anion-exchange resin beads as hard template and further converted into their H-form. Next, the zeolite beads were partially dealuminated using different concentrations of HNO3 (i.e., 1.8 or 7.2 M), followed by grafting with one of the above-mentioned metals (Sn, Zr or Hf) to introduce Lewis acid sites. These bimetallic zeolites were tested as heterogeneous catalysts in the conversion of dihydroxyacetone (DHA) to methyl lactate (ML). The Sn-containing zeolite Beta beads treated by 1.8 M HNO3 and grafted with 27 mmol of SnCl4 (Sn-deAl-1.8-Beta-B) demonstrated the best catalytic activity among the prepared bimetallic zeolite beads, with 99% selectivity and 90% yield of ML after 6 h at 90 °C. This catalyst was also tested in combination with Au-Pd nanoparticles supported on functionalized carbon nanotubes (CNTs) as multifunctional catalytic system for the conversion of glycerol to ML, achieving 29% conversion of glycerol and 67% selectivity towards ML after 4.5 h at 140 °C under 30 bar air. The catalytic results were rationalized by means of a thorough characterization of the zeolitic beads with a combination of techniques (XRD, N2-physisorption, SEM, XRF, TEM, UV-vis spectroscopy and pyridine-FT-IR).

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Recent advances in the utilization of glycerol for the production of lactic acid by catalysis

Wang

Yang

et al. 2022

Biofuels Bioprod Bioref

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In this review, the research progress on catalytic conversion of glycerol to lactic acid or lactate esters and the reaction mechanisms with different catalysis systems are summarized. Both homogeneous catalysts, including inorganic bases and metal complexes, and heterogeneous catalysts, including metal oxides, molecular sieves, polyoxometalates and noble and non‐noble metals, are discussed. In particular, the influence of catalyst components, the physical and chemical properties of the catalysts and additives and solvents on the catalytic performances are highlighted. In comparison, nano‐metal particles or bimetal catalysts could achieve good catalytic performance, in which the alloy and synergistic effects might form under certain conditions. For further improvement of the sustainable transformation of glycerol to lactic acid or lactate esters, attention should still be paid to rational design of novel cost‐effective, high‐efficiency and green catalytic systems. © 2022 Society of Chemical Industry and John Wiley & Sons, Ltd.

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Base-free conversion of glycerol to methyl lactate using a multifunctional catalytic system consisting of Au–Pd nanoparticles on carbon nanotubes and Sn-MCM-41-XS

Abstract: Base-free, multifunctional heterogenous catalytic systems for the highly efficient conversion of glycerol into methyl lactate.

Cited by 20 publications

References 54 publications

Analyzing the surface of functional nanomaterials—how to quantify the total and derivatizable number of functional groups and ligands

Analyzing the surface of functional nanomaterials—how to quantify the total and derivatizable number of functional groups and ligands

Bimetallic Zeolite Beta Beads with Hierarchical Porosity as Brønsted-Lewis Solid Acid Catalysts for the Synthesis of Methyl Lactate

Recent advances in the utilization of glycerol for the production of lactic acid by catalysis

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