Synthesis of ionic liquids in micro-reactors—a process intensification study

Waterkamp, Daniel A.; Heiland, Michael; Schlüter, Michael; Sauvageau, Janelle; Beyersdorff, Tom; Thöming, Jorg

doi:10.1039/b616882e

Cited by 88 publications

(84 citation statements)

References 11 publications

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“…Typically, quaternization reactions are highly exothermic reactions. It has been reported that the heat of reaction for 1-methylimidazole and 1-bromobutane is -96 kJ mol -1 by Waterkamp et al 20 They estimated the adiabatic temperature for a run-away reaction for this system to be 48…”

Section: Reactions: Solvent or Solvent-less?mentioning

confidence: 96%

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Kinetics and solvent effects in the synthesis of ionic liquids: imidazolium

Schleicher

Scurto

2009

Green Chem.

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Ionic liquids (ILs) are being considered as a promising class of potentially environmentally-friendly ("green") solvents and materials for use in a variety of applications. However, ionic liquids are conventionally synthesized by batch, without known kinetics, in non-sustainable solvents. For ILs to be a truly "green" technology for widespread use, they must themselves be made in a correspondingly benign manner for low cost, as enabled by process development. This investigation will illustrate the kinetics and large solvent effects in the synthesis of 1-hexyl-3-methyl-imidazolium bromide in 10 different solvents: acetone, acetonitrile, 2-butanone, chlorobenzene, dichloromethane, dimethyl sulfoxide (DMSO), ethyl formate, ethyl lactate, methanol, and cyclopentanone. The kinetic rate constant for the synthesis in DMSO is over an order-of-magnitude larger than that in methanol. While the kinetic rate of these type of S N 2 reactions is generally known to increase with solvent "polarity", multi-parameter solvent descriptors, e.g. of Kamlet and Taft, are required to quantify these effects in a Linear Solvation Energy Relationship. These relationships are used with environmental and toxicity databases, such as the Rowan Solvent Selection Table, to rapidly optimize the solvent for favorable kinetics and minimal human and environmental impact.

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Section: Reactions: Solvent or Solvent-less?mentioning

confidence: 96%

“…20 This amount of heat release can cause a number of safety concerns along with poor quality product. Burrell et al 21 investigated synthesis of larger scale quantities (~1 kg) of ILs and warn: "Caution: [this] reaction is exothermic and cooling is advisable for large scale reactions".…”

Section: Reactions: Solvent or Solvent-less?mentioning

confidence: 99%

Kinetics and solvent effects in the synthesis of ionic liquids: imidazolium

Schleicher

Scurto

2009

Green Chem.

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“…Although many processes have been developed to decrease the production cost of ILs (Estager et al, 2007;Waterkamp et al, 2007) COO] did not dissolve the wood flour; however, facile extraction of the lignin was achieved. A strong inverse relationship was found between the effectiveness of cellulase-catalyzed hydrolysis of wood flour cellulose and both lignin content and cellulose crystallinity.…”

Section: Reuse Of [Emim][ch 3 Coo] To Pretreat Wood Flourmentioning

confidence: 99%

Ionic liquid‐mediated selective extraction of lignin from wood leading to enhanced enzymatic cellulose hydrolysis

Lee

Doherty

Linhardt

et al. 2008

Biotech & Bioengineering

848

571

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Lignocellulose represents a key sustainable source of biomass for transformation into biofuels and bio-based products. Unfortunately, lignocellulosic biomass is highly recalcitrant to biotransformation, both microbial and enzymatic, which limits its use and prevents economically viable conversion into value-added products. As a result, effective pretreatment strategies are necessary, which invariably involves high energy processing or results in the degradation of key components of lignocellulose. In this work, the ionic liquid, 1-ethyl-3-methylimidazolium acetate ([Emim][CH 3 COO]), was used as a pretreatment solvent to extract lignin from wood flour. The cellulose in the pretreated wood flour becomes far less crystalline without undergoing solubilization. When 40% of the lignin was removed, the cellulose crystallinity index dropped below 45, resulting in >90% of the cellulose in wood flour to be hydrolyzed by Trichoderma viride cellulase. [Emim] [CH 3 COO] was easily reused, thereby resulting in a highly concentrated solution of chemically unmodified lignin, which may serve as a valuable source of a polyaromatic material as a value-added product.

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“…Waterkamp et al [60] presented a process to intensify the synthesis of 1-butyl-3-methylimidazolium bromide ([BMIM]Br) by using a continuously operating microreactor system ( Figure 7 ). The reaction unit is composed of a microstructured mixer of 450 mm channel width and with an inner diameter ranging from 2 to 6 mm, allowing a production rate of 9.3 kg [BMIM]Br per day.…”

Section: Production Of Ionic Liquidsmentioning

confidence: 99%

Process intensification in green synthesis

Kumar

Nigam

2012

Green Processing and Synthesis

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In the past few decades there has been an extensive increase in the research for green synthesis processes due to environmental concerns, industrial safety and sustainable development, which makes it an attractive alternative to the conventional synthesis processes. The interest of researchers in the green synthesis processes highlights the importance of understanding the mechanism and the fundamental differences between the different processes. The number of publications in the fi eld of " Green Synthesis " in journals, proceedings, patents, etc. has increased by almost 20 times from 2001 to 2010. The published reports are mainly concerned with green synthesis with catalytic processes, less harmful solvents and process intensifi ed techniques. In the present article, the technological development efforts in the area of green synthesis are summarized. Various techniques for green synthesis process intensifi cation are discussed, e.g., mixers, microreactors, spin disc reactor, oscillated fl ow reactors, microwave irradiation, ultrasonication, multifunctional membranes and coiled fl ow inverter. The applications of green synthesis processes for biofuel, nanoparticle, ionic liquids and pharmaceutical production are also discussed.

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Synthesis of ionic liquids in micro-reactors—a process intensification study

Cited by 88 publications

References 11 publications

Kinetics and solvent effects in the synthesis of ionic liquids: imidazolium

Kinetics and solvent effects in the synthesis of ionic liquids: imidazolium

Ionic liquid‐mediated selective extraction of lignin from wood leading to enhanced enzymatic cellulose hydrolysis

Process intensification in green synthesis

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