Development of a Supported Ionic Liquid Phase (SILP) Catalyst for Slurry‐Phase Friedel–Crafts Alkylations of Cumene

Joni, J.; Haumann, Marco; Wasserscheid, Peter

doi:10.1002/adsc.200800672

Cited by 61 publications

(27 citation statements)

References 37 publications

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“…Initially [140,141]. The time required to reach 80% conversion was six times shorter with SILP, compared to the liquid-liquid biphasic reaction using the same ionic liquid.…”

Section: Silp and Scillmentioning

confidence: 97%

Lewis Acidic Ionic Liquids

Brown

Hogg

Swadźba‐Kwaśny

2017

Topics in Current Chemistry Collections

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Until very recently, the term Lewis acidic ionic liquids (ILs) was nearly synonymous with halometallate ILs, with a strong focus on chloroaluminate(III) systems. The first part of this review covers the historical context in which these were developed, speciation of a range of halometallate ionic liquids, attempts to quantify their Lewis acidity, and selected recent applications: in industrial alkylation processes, in supported systems (SILPs/SCILLs) and in inorganic synthesis. In the last decade, interesting alternatives to halometallate ILs have emerged, which can be divided into two subsections: (1) liquid coordination complexes (LCCs), still based on halometallate species, but less expensive and more diverse than halometallate ionic liquids, and (2) ILs with main-group Lewis acidic cations. The two following sections cover these new liquid Lewis acids, also highlighting speciation studies, Lewis acidity measurements, and applications.

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“…Initially [140,141]. The time required to reach 80% conversion was six times shorter with SILP, compared to the liquid-liquid biphasic reaction using the same ionic liquid.…”

Section: Silp and Scillmentioning

confidence: 97%

Lewis Acidic Ionic Liquids

Brown

Hogg

Swadźba‐Kwaśny

2017

Topics in Current Chemistry Collections

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“…Joni et al developed a well-defined and optimized pretreatment of silica support materials prior to impregnation with an acidic chloroaluminate IL [88]. A solution of n([C 2 C 1 Im]Cl)/n(AlCl 3 ) = 1/2 and DCM was contacted with the calcined silica.…”

Section: Supported Ionic Liquid Phase (Silp) Catalysismentioning

confidence: 99%

“…These SILP catalysts were successfully tested in the slurry-phase Friedel-Crafts alkylation of cumene and in the continuous gas-phase isopropylation of cumene and toluene. The catalysts operated with constant high selectivity and unchanged catalytic activity for 210 h time-on-stream [88,89].…”

Section: Supported Ionic Liquid Phase (Silp) Catalysismentioning

confidence: 99%

Ionic Liquids in Catalysis

2014

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Ionic liquids (ILs), salts with melting points below 100°C, represent a fascinating class of liquid materials typically characterized by an extremely low vapor pressure. Besides their application as new solvents or as electrolytes for electrochemical purposes, there are two important concepts of using ILs in catalysis: Liquid-liquid biphasic catalysis and IL thin film catalysis. Liquid-liquid biphasic catalysis enables either a very efficient manner to apply catalytic ILs, e.g. in Friedel-Crafts reactions, or to apply ionic transition metal catalyst solutions. In both cases, phase separation after reaction allows an easy separation of reaction products and catalyst re-use. One problem of liquidliquid biphasic catalysis is mass transfer limitation. If the chemical reaction is much faster than the liquid-liquid mass transfer the latter limits the overall reaction rate. This problem is overcome in IL thin film catalysis where diffusion pathways and thus the characteristic time of diffusion are short. Here, Supported Ionic Liquid Phase (SILP) and Solid Catalyst with Ionic Liquid Layer (SCILL) are the two most important concepts. In both, a high surface area solid substrate is covered with a thin IL film, which contains either a homogeneously dissolved transition metal complex for SILP, or which modifies catalytically active surface sites at the support for SCILL. In each concept, interface phenomena play a very important role: These may concern the interface of an IL phase with an organic phase in the case of liquidliquid biphasic catalysis. For IL thin film catalysis, the interfaces of the IL with the gas phase and with catalytic nanoparticles and/or support materials are of critical importance. It has recently been demonstrated that these interfaces and also the bulk of ILs can be investigated in great detail using surface science studies, which greatly contributed to the fundamental understanding of the catalytic properties of ILs and supported IL materials. Exemplary results concerning the IL/vacuum or IL/gas interface, the solubility and surface enrichment of dissolved metal complexes, the IL/support interface and the in situ monitoring of chemical reactions in ILs are presented.

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“…observed that the performance of the Rh‐catalysed hydroformylation using propene was strongly linked to ionic liquid loading on the silica support 8a. In addition, following optimisation of the acidic chloroaluminate SILP catalyst for a slurry phase Friedel–Crafts alkylation of cumene, a critical ionic liquid loading value was found to be necessary to overcome the neutralisation of the chloroaluminate with the surface silanol groups on the silica 19…”

Section: Resultsmentioning

confidence: 99%

Asymmetric Carbon‐Carbon Bond Forming Reactions Catalysed by Metal(II) Bis(oxazoline) Complexes Immobilized using Supported Ionic Liquids

et al. 2011

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A series of bis(oxazoline) metal(II) complexes has been supported on silica and carbon supports by non-covalent immobilisation using an ionic liquid. The catalytic performance of these solids was compared for the enantioselective Diels-Alder reaction between N-acryloyloxazolidinone and cyclopentadiene and the Mukaiyama-aldol reaction between methyl pyruvate and 1-methoxy-1-trimethylsilyloxypropene. In both reactions the enantioselectivity was strongly influenced by the choice of support displaying enantioselectivies (ee values) up to 40% higher than those conducted under homogeneous reaction conditions.

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Development of a Supported Ionic Liquid Phase (SILP) Catalyst for Slurry‐Phase Friedel–Crafts Alkylations of Cumene

Cited by 61 publications

References 37 publications

Lewis Acidic Ionic Liquids

Lewis Acidic Ionic Liquids

Ionic Liquids in Catalysis

Asymmetric Carbon‐Carbon Bond Forming Reactions Catalysed by Metal(II) Bis(oxazoline) Complexes Immobilized using Supported Ionic Liquids

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