Tailoring ionic liquid catalysts: structure, acidity and catalytic activity of protonic ionic liquids based on anionic clusters, [(HSO4)(H2SO4)x]− (x = 0, 1, or 2)

Matuszek, Karolina; Chrobok, Anna; Coleman, Fergal; Seddon, Kenneth R.; Swadźba‐Kwaśny, Małgorzata

doi:10.1039/c4gc00415a

Cited by 82 publications

(87 citation statements)

References 33 publications

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“…Similarly, in ionic liquids formed by proton transfer from acids to bases, hydrogen-bonded complex anions and cations, can be generated in addition to simple ions following the equilibria shown below: 4 H À A Ð …”

Section: Acid-base Mixturesmentioning

confidence: 99%

Association and liquid structure of pyridine–acetic acid mixtures determined from neutron scattering using a ‘free proton’ EPSR simulation model

McCune

Turner

Coleman

et al. 2015

Phys. Chem. Chem. Phys.

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The liquid structure of pyridine-acetic acid mixtures have been investigated using neutron scattering at various mole fractions of acetic acid, χHOAc = 0.33, 0.50, and 0.67 and compared to the structures of neat pyridine and acetic acid. Data has been modelled using empirical potential structure refinement (EPSR) with a 'free proton' reference model, which has no prejudicial weighting towards either the existence of molecular or ionised species. Analysis of the neutron scattering results shows the existence of hydrogen-bonded acetic acid chains with pyridine inclusions, rather than the formation of an ionic liquid by proton transfer.

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Section: Acid-base Mixturesmentioning

confidence: 99%

Association and liquid structure of pyridine–acetic acid mixtures determined from neutron scattering using a ‘free proton’ EPSR simulation model

McCune

Turner

Coleman

et al. 2015

Phys. Chem. Chem. Phys.

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“…4,5 At a fundamental level, these solutions are interesting as complex fluids with a dense network of hydrogen bonds.…”

Section: Solutions Of Acids In Ionic Liquidsmentioning

confidence: 99%

“…6 Table 1 for the list of abbreviations used in this work) were reported to contain a dense network of H-bonds between all charged species. 10 Similarly, ionic liquids formed by proton transfer between an acid and a base, with the acid in excess, have been shown to form complex anions, for example [F(HF) x ] -, 11 [tfa(Htfa)] -, 6 [HSO 4 (H 2 SO 4 ) x ] -, 5 and a wide range of carboxylate-carboxylic acid clusters. 1,12,13 Poorly ionic mixtures of 1-methylpyrrolidine and acetic acid were shown to contain polymeric [OAc(HOAc) x ] -anions.…”

Section: Solutions Of Acids In Ionic Liquidsmentioning

confidence: 99%

Brønsted acids in ionic liquids: how acidity depends on the liquid structure

McCune

Petković

et al. 2014

Phys. Chem. Chem. Phys.

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“…In recent years, ionic liquids have attracted much interest for their unique properties such as non-volatility, non-flammability, high chemical and thermal stability. [11][12][13][14][15] [AlCl3] would result in high activity. These kinds of ionic liquid catalysts could not be reused for many times because of their moisture sensitivity.…”

Section: Introductionmentioning

confidence: 99%

Durability enhanced ionic liquid catalyst for Friedel–Crafts reaction between benzene and 1-dodecene: insight into catalyst deactivation

Wan

Zhang

et al. 2015

RSC Adv.

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Friedel-Craft alkylation of benzene with 1-dodecene, which is an important reaction of synthetic detergent, was studied using the catalyst of [bmim][TFSI]/AlCl3 (1-butyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide/AlCl3). These ionic liquid catalysts show biphasic behaviors at specific condition. Active site species and Lewis acidity were determined by NMR and acetonitrile probe FT-IR. NMR spectroscopy investigations indicated that "Coordinated" and "uncoordinated"[TFSI]existed in the ionic liquid catalyst system sumultaneity, while tetrahedral 4-coordinate Al2Cl7was the main active specie for Friedel-Craft alkylation. The complexation [AlClx(TFSI)y]tend to decompose and release 4-coordinated Al2Cl7and [TFSI] -. The phase behaviors study of the ionic liquid [bmim][TFSI]/AlCl3 demonstrated that the upper phase could be used as an efficient heterogeneous catalyst when AlCl3/IL≥1.5. Due to the presence of anion [TFSI]around active sites, especially [TFSI]at "uncoordinated" state, ionic liquid formed a stable and hydrophobic chemical environment, which enhanced catalysts durability. The influence of various reaction conditions including catalyst reusability on the alkylation reaction was studied, and the potential reasons to catalyst deactivation were discussed. The highest 2-LAB selectivity was more than 50% when 1-dodecene conversion was nearly 100%. Comparing with liquid or solid acid catalyst, ionic liquid catalysts have many advantages in perspectives concerning energy and environmental.

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Tailoring ionic liquid catalysts: structure, acidity and catalytic activity of protonic ionic liquids based on anionic clusters, [(HSO₄)(H₂SO₄)_x]⁻ (x = 0, 1, or 2)

Abstract: The speciation of a family of inexpensive, easily prepared protonic ionic liquids, their physico-chemical properties and their performance as catalysts in the model esterification reaction have been correlated.

Cited by 82 publications

References 33 publications

Association and liquid structure of pyridine–acetic acid mixtures determined from neutron scattering using a ‘free proton’ EPSR simulation model

Association and liquid structure of pyridine–acetic acid mixtures determined from neutron scattering using a ‘free proton’ EPSR simulation model

Brønsted acids in ionic liquids: how acidity depends on the liquid structure

Durability enhanced ionic liquid catalyst for Friedel–Crafts reaction between benzene and 1-dodecene: insight into catalyst deactivation

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