Milligram-scale, temperature-controlled ball milling to provide an informed basis for scale-up to reactive extrusion

Andersen, Joel; Starbuck, Hunter; Current, Tia; Martin, S. T.; Mack, James

doi:10.1039/d1gc02174e

Cited by 25 publications

(21 citation statements)

References 46 publications

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“…Furthermore, the translation from ball-milling to reactive extrusion is often not straightforward, and we hope this review may act as a starting point guide for end users looking to engage in continuous mechanochemistry, and the wealth of opportunities this currently under-utilised technique has to offer. 49…”

Section: Conclusion and Future Outlookmentioning

confidence: 99%

Continuous flow mechanochemistry: reactive extrusion as an enabling technology in organic synthesis

Bolt¹,

Leitch²,

Jones

et al. 2022

Chem. Soc. Rev.

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Section: Conclusion and Future Outlookmentioning

confidence: 99%

Continuous flow mechanochemistry: reactive extrusion as an enabling technology in organic synthesis

Bolt¹,

Leitch²,

Jones

et al. 2022

Chem. Soc. Rev.

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“…Nearly identical kinetic profiles for the solution and milling reactions were subsequently obtained by Andersen et al when the temperature of the milling assembly was held constant at 60 °C, verifying the influence of temperature on the reaction. 100 The Emmerling group utilized a combination of ex situ XRPD and Raman spectroscopy with extremely high sampling frequency to monitor the mechanochemical formation of a MOF from bismuth(III) nitrate (HIm) and 1,4-benzenedicarboxylic acid (1,4-bdc), as well as of the cocrystallization of indometacin (ind) with carbamazepine (cbz). 101 A high temporal resolution of 10 s enabled the detection of a crystalline intermediate within the first minute of milling for the formation of the bismuth framework (Figure 13).…”

Section: Ex Situ Analysis At Multiple Time Points (Stepwise Analysis)...mentioning

confidence: 99%

“…The cohesive state is thought to facilitate reactant diffusion, as well as enable wrapping of the reaction mixture around the milling ball (the “snowballing” effect) to form a shell that leads to enhanced reaction mixture heating. Nearly identical kinetic profiles for the solution and milling reactions were subsequently obtained by Andersen et al when the temperature of the milling assembly was held constant at 60 °C, verifying the influence of temperature on the reaction …”

Section: Monitoring Milling Reactionsmentioning

confidence: 99%

Methods for Monitoring Milling Reactions and Mechanistic Studies of Mechanochemistry: A Primer

Julien

Friščić

2022

Crystal Growth & Design

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Mechanochemistry by ball milling is garnering significant attention as an efficient and versatile means of chemical synthesis which minimizes the need for solvents and reduces the amount of energy required to conduct many molecular transformations. Understanding milling reactions often requires monitoring the reaction of solid forms, with little or ideally no disruption of the milling process. Herein, we provide a broad but succinct summary of how different ex situ and the more recently developed in situ techniques have been applied to monitor mechanochemical reactions, revealing reaction pathways and the mechanisms driving different solid-state molecular and materials transformations by milling. The rapidly evolving field of monitoring milling reactions has already revolutionized our understanding of mechanochemical reactions, revealing complex self-assembled phases as intermediates in catalytic and other types of synthesis through ball milling. The multitude of recently reported techniques for investigating ball milling reactions, many of which are touched upon in this summary, promise to dramatically increase the pace of mechanochemical reaction development and the understanding of solid-state chemistry.

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“…This setup was used to synthesize different derivatives containing urea and amido groups, 63 nucleophilic aromatic substitutions (S N Ar) products, 63 and prebiotic oligomerization of amino acids. 64 Moreover, high-temperature ball milling on a laboratory scale was exploited in the scale-up of the syntheses of S N Ar and Knoevenagel reactions, 65 as well as agrochemicals based on urea and gypsum cocrystals, 66 using the continuous mechanochemical manufacturing by twin-screw extrusion. The mentioned examples demonstrate the versatility of mechanochemical synthesis and showcase a wide range of substrates.…”

Section: ■ Introductionmentioning

confidence: 99%

Sustainable Synthesis of Diamondoid Ethers by High-Temperature Ball Milling

Alić

Stolar

Štefanić

et al. 2023

ACS Sustainable Chem. Eng.

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Diamondoids have emerged as promising carbon-based nanomaterial building blocks because of their unique combination of exceptional properties and availability for selective functionalization. Until now, the chemical functionalization of diamondoids was primarily based on solution methods. However, the limited solubility of diamondoid derivatives and their tendency to sublimate at even slightly elevated temperatures made it difficult to prepare more extensive diamondoid scaffolds. Here, we present the first mechanochemical synthesis of several diamondoid ethers differing in the type, size, and number of their hydrocarbon cage subunits. We found that the efficient preparation of these ethers is enabled solely by high-temperature ball milling conditions and does not proceed under ambient conditions. When compared to the conventional synthesis of the same ether derivatives, the calculated green chemistry metrics showed the enormous sustainability benefits of the mechanochemical synthesis. The mechanochemical approach includes shorter reaction times, a green inorganic base, a simplified workup procedure, comparable or superior reaction yields, and the elimination of solvents in the synthesis. Furthermore, crystal structures obtained from single-crystal X-ray diffraction experiments confirmed the molecular structures of the target products and gave insight into their intermolecular interactions in the solid state. From the perspective of the future applicability of these materials in nanotechnology, the cost and sustainability of their preparation are paramount. We demonstrated herein that mechanochemistry is a viable option for this challenge.

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Milligram-scale, temperature-controlled ball milling to provide an informed basis for scale-up to reactive extrusion

Abstract: Over the last several years, chemists and engineers have identified the utility of using twin-screw extruders for performing large-scale organic chemistry mechanochemically. This equipment is convenient as it is familiar...

Cited by 25 publications

References 46 publications

Continuous flow mechanochemistry: reactive extrusion as an enabling technology in organic synthesis

Continuous flow mechanochemistry: reactive extrusion as an enabling technology in organic synthesis

Methods for Monitoring Milling Reactions and Mechanistic Studies of Mechanochemistry: A Primer

Sustainable Synthesis of Diamondoid Ethers by High-Temperature Ball Milling

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