Matthew Lui - Academia.edu (original) (raw)

Papers by Matthew Lui

Applied Catalysis B-environmental, May 1, 2023

Chemsuschem, Aug 16, 2016

An easily prepared masked N-heterocyclic carbene, 1,3-dimethylimidazolium-2-carboxylate (DMI-CO2 ... more An easily prepared masked N-heterocyclic carbene, 1,3-dimethylimidazolium-2-carboxylate (DMI-CO2 ), was investigated as a "green" and inexpensive organocatalyst for the alkylation of phenols. The process made use of various low-toxicity and renewable alkylating agents, such as dimethyl- and diethyl carbonate, in a focused microwave reactor. DMI-CO2 was found to be a very active catalyst and excellent yields of a range of aryl alkyl ethers were obtained under relatively benign conditions. The observed difference in the conversion behavior of phenol methylation, in the presence of either the carbene or 1,8-diazabicycloundec-7-ene (DBU) catalyst, was rationalized on the basis of mechanistic investigations. The primary mode of action for the N-heterocyclic carbene is nucleophilic catalysis. Activation of the dialkyl carbonate electrophile results in concomitant evolution of an organo-soluble alkoxide, which deprotonates the phenolic starting material. In contrast, DBU is initially protonated by the phenol and thus consumed. Subsequent regeneration and participation in nucleophilic catalysis only becomes significant after some phenolate alkylation occurs.

Chemcatchem, Jun 26, 2017

The catalytic depolymerization of Kraft lignin in supercritical ethanol was explored in the prese... more The catalytic depolymerization of Kraft lignin in supercritical ethanol was explored in the presence of Mo2C-and MoS2-based catalysts. At 280 °C, Mo2C and Mo2C/Al2O3 afforded aromatic yields of 425 and 419 mg/g lignin, respectively: amongst the highest yields reported to date. Ionic-liquid-assisted delamination of MoS2 resulted in highly active catalysts, capable of quantitative conversion of lignin at the expense of aromatic yield (ca 186 mg/g lignin). Across all the catalysts studied, between 0.04 wt% and 0.38 wt% of molybdenum leached into solution under supercritical conditions, according to ICP analyses (corresponding to 27-570 µg of molybdenum in the reaction supernatant). A small contribution to the molybdenum in solution comes from the reactor itself (Hastelloy C contains 16 wt% Mo). Analysis of a depolymerization performed with fresh Kraft lignin and the soluble portion of the reaction mixture from a previous reactor run indicated that the leached species were neither active enough to afford the high conversions observed, nor selective enough to give high yields of aromatic products. In conjunction with the ICP data and differential chemoselectivities of the Mo2C-and MoS2-based catalysts, these results suggest that the bulk of the catalysis is heterogeneous.

ACS Sustainable Chemistry & Engineering, Jan 16, 2019

In this study, the extractive desulfurization of model fuel oil with ionic liquids (ILs) has been... more In this study, the extractive desulfurization of model fuel oil with ionic liquids (ILs) has been studied in an attempt to gain insights into the dominant forces controlling the extraction efficien...

European Journal of Organic Chemistry, Nov 26, 2018

A facile process for the methylation of phloroglucinol using environmentally friendly dimethyl ca... more A facile process for the methylation of phloroglucinol using environmentally friendly dimethyl carbonate as methylating agent and solvent is described. Widely available and inexpensive solid acids have been used as catalysts to promote this transformation. H-Y zeolite proved particularly selective for monomethylation, hence it has been used for the convenient preparation of methoxyresorcinol (MR), with only limited co-production of dimethoxyphenol (DMP). Conversely, the use of tungstosilic acid on silica easily afforded DMP in excellent isolated yield.

Energy & Fuels, Dec 9, 2016

Ionic Liquids (ILs) have been suggested as useful extractants of aromatic nitrogencontaining comp... more Ionic Liquids (ILs) have been suggested as useful extractants of aromatic nitrogencontaining compounds (N-compounds) from fuel oils. In this systematic study, ILs based on common cations and anions are employed as extractants of the archetypical N-compounds pyridine and indole from a model oil consisting of decane and toluene. The performance of these ILs as extractants of N-compounds is compared and rationalized. It is demonstrated that the cation and anion sizes (offering more surface area for extractants to interact) are the major

ChemSusChem, 2021

Dimethyl sulfide, a major byproduct of the Kraft pulping process, was used as an inexpensive and ... more Dimethyl sulfide, a major byproduct of the Kraft pulping process, was used as an inexpensive and sustainable catalyst/co‐reagent (methyl donor) for various methylations with dimethyl carbonate (as both reagent and solvent), which afforded excellent yields of O‐methylated phenols and benzoic acids, and mono‐C‐methylated arylacetonitriles. Furthermore, these products could be isolated using a remarkably straightforward workup and purification procedure, realized by dimethyl sulfide‘s neutral and distillable nature and the absence of residual salts. The likely mechanisms of these methylations were elucidated using experimental and theoretical methods, which revealed that the key step involves the generation of a highly reactive trimethylsulfonium methylcarbonate intermediate. The phenol methylation process represents a rare example of a Williamson‐type reaction that occurs without the addition of a Brønsted base.

ChemSusChem, 2020

Using lignin model compounds with relevant key characteristic structural features, the reaction p... more Using lignin model compounds with relevant key characteristic structural features, the reaction pathways of α-O-4 arylether linkages under hydrothermal conditions were elucidated. Our experimental results and computational modelling suggest that the α-O-4 linkages in lignin undergo catalyzed hydrolyses and eliminations to give phenolic and alkenylbenzene derivatives as major products in subcritical water. The decreased relative permittivity of water at these high temperatures and pressures facilitates the elimination reactions. The alkyl group on the α-carbon and the methoxy groups on the phenyl rings both have positive effects on the rate of conversion of α-O-4 linkages in native lignin.

ACS Sustainable Chemistry & Engineering, 2019

In this study, the extractive desulfurization of model fuel oil with ionic liquids (ILs) has been... more In this study, the extractive desulfurization of model fuel oil with ionic liquids (ILs) has been studied in an attempt to gain insights into the dominant forces controlling the extraction efficien...

European Journal of Organic Chemistry, 2018

A facile process for the methylation of phloroglucinol using environmentally friendly dimethyl ca... more A facile process for the methylation of phloroglucinol using environmentally friendly dimethyl carbonate as methylating agent and solvent is described. Widely available and inexpensive solid acids have been used as catalysts to promote this transformation. H‐Y zeolite proved particularly selective for monomethylation, hence it has been used for the convenient preparation of methoxyresorcinol (MR), with only limited co‐production of dimethoxyphenol (DMP). Conversely, the use of tungstosilicic acid on silica easily afforded DMP in excellent isolated yield.

ChemSusChem, May 29, 2017

Using both experimental and computational methods, focusing on intermediates and model compounds,... more Using both experimental and computational methods, focusing on intermediates and model compounds, some of the main features of the reaction mechanisms that operate during the hydrothermal processing of lignin were elucidated. Key reaction pathways and their connection to different structural features of lignin were proposed. Under neutral conditions, subcritical water was demonstrated to act as a bifunctional acid/base catalyst for the dissection of lignin structures. In a complex web of mutually dependent interactions, guaiacyl units within lignin were shown to significantly affect overall lignin reactivity.

ChemCatChem, 2017

The catalytic depolymerization of Kraft lignin in supercritical ethanol was explored in the prese... more The catalytic depolymerization of Kraft lignin in supercritical ethanol was explored in the presence of Mo2C-and MoS2-based catalysts. At 280 °C, Mo2C and Mo2C/Al2O3 afforded aromatic yields of 425 and 419 mg/g lignin, respectively: amongst the highest yields reported to date. Ionic-liquid-assisted delamination of MoS2 resulted in highly active catalysts, capable of quantitative conversion of lignin at the expense of aromatic yield (ca 186 mg/g lignin). Across all the catalysts studied, between 0.04 wt% and 0.38 wt% of molybdenum leached into solution under supercritical conditions, according to ICP analyses (corresponding to 27-570 µg of molybdenum in the reaction supernatant). A small contribution to the molybdenum in solution comes from the reactor itself (Hastelloy C contains 16 wt% Mo). Analysis of a depolymerization performed with fresh Kraft lignin and the soluble portion of the reaction mixture from a previous reactor run indicated that the leached species were neither active enough to afford the high conversions observed, nor selective enough to give high yields of aromatic products. In conjunction with the ICP data and differential chemoselectivities of the Mo2C-and MoS2-based catalysts, these results suggest that the bulk of the catalysis is heterogeneous.

ChemSusChem, Sep 8, 2016

An easily prepared masked N-heterocyclic carbene, 1,3-dimethylimidazolium-2-carboxylate (DMI-CO2 ... more An easily prepared masked N-heterocyclic carbene, 1,3-dimethylimidazolium-2-carboxylate (DMI-CO2 ), was investigated as a "green" and inexpensive organocatalyst for the alkylation of phenols. The process made use of various low-toxicity and renewable alkylating agents, such as dimethyl- and diethyl carbonate, in a focused microwave reactor. DMI-CO2 was found to be a very active catalyst and excellent yields of a range of aryl alkyl ethers were obtained under relatively benign conditions. The observed difference in the conversion behavior of phenol methylation, in the presence of either the carbene or 1,8-diazabicycloundec-7-ene (DBU) catalyst, was rationalized on the basis of mechanistic investigations. The primary mode of action for the N-heterocyclic carbene is nucleophilic catalysis. Activation of the dialkyl carbonate electrophile results in concomitant evolution of an organo-soluble alkoxide, which deprotonates the phenolic starting material. In contrast, DBU is initi...

Energy & Fuels, 2016

Ionic Liquids (ILs) have been suggested as useful extractants of aromatic nitrogencontaining comp... more Ionic Liquids (ILs) have been suggested as useful extractants of aromatic nitrogencontaining compounds (N-compounds) from fuel oils. In this systematic study, ILs based on common cations and anions are employed as extractants of the archetypical N-compounds pyridine and indole from a model oil consisting of decane and toluene. The performance of these ILs as extractants of N-compounds is compared and rationalized. It is demonstrated that the cation and anion sizes (offering more surface area for extractants to interact) are the major

ACS Sustainable Chemistry & Engineering, 2019

Structural Chemistry, 2016

Dry gamma-valerolactone (GVL) is stable for several weeks at 150°C and its thermal decomposition ... more Dry gamma-valerolactone (GVL) is stable for several weeks at 150°C and its thermal decomposition only proceeds in the presence of appropriate catalysts. Since GVL does not react with water up to 60°C for several weeks, it could be used as a green solvent at mild conditions. At higher temperatures, GVL reacts with water to form 4-hydroxyvaleric acid (4-HVA) and reaches the equilibrium in a few days at 100°C. Aqueous solutions of acids (HCl and H 2 SO 4) catalyze the ring opening of GVL even at room temperature, which leads to the establishment of an equilibrium between GVL, water, and 4-HVA. Although the 4-HVA concentration would be below 4 mol% in the presence of acids, it could be higher than the concentration of a reagent or a catalyst precursor, not to mention a catalytically active species. The latter could be especially worrisome as 4-HVA could be an excellent bi-or even a tri-dentate ligand for transition metals. Aqueous solution of bases (NaOH and NH 4 OH) also catalyzes the reversible ring opening of GVL. While in the case of NaOH, the product is the sodium salt of 4-hydroxyvalerate, the reversible reaction of GVL, with NH 4 OH results in the formation of 4-hydroxyvaleric amide. The reversible ring opening of (S)-GVL in the presence of HCl or NaOH has no effect on the stability of the chiral center.

Org. Chem. Front., 2014

Nonafluoro-t-butyl propyl (1), allyl (2), and propargyl (3) ethers as well as 1,2-bis(nonafluoro-... more Nonafluoro-t-butyl propyl (1), allyl (2), and propargyl (3) ethers as well as 1,2-bis(nonafluoro-t-butoxy)ethane (4), 1,3-bis(nonafluoro-t-butoxy)-propane (5), and 1,4-bis(nonafluoro-t-butoxy)-butane (6) were prepared by the reaction of sodium nonafluoro-t-butoxide (7) with the corresponding alkyl halides in good yields. Their fluorous partition coefficients and toxicity were also investigated. Computational studies have shown that 4, 5 and 6 exist in a monomeric form in MeOH–CF3C6F11 and they likely aggregate to form oligomers in PhCH3–CF3C6F11.

Chemical Science, 2011

ABSTRACT Solvents and solutions are ubiquitous in chemistry. For instance, in synthesis the solve... more ABSTRACT Solvents and solutions are ubiquitous in chemistry. For instance, in synthesis the solvent allows reagents to mix intimately so that reactions between these may occur. Consequently, understanding how solutes behave in solutions has been one of the major themes of chemistry throughout its history. Ionic liquids (liquid salts) are an exciting recent addition to the range of available solvents. Here we show that these solvents interact with dissolved salts to give solutions that are completely different from those of salts in either traditional organic solvents or water. Observations of these ideal salt solutions will require new models of solvation and polarity and have the potential to lead to new chemical processes.

Applied Catalysis B-environmental, May 1, 2023

Chemsuschem, Aug 16, 2016

An easily prepared masked N-heterocyclic carbene, 1,3-dimethylimidazolium-2-carboxylate (DMI-CO2 ... more An easily prepared masked N-heterocyclic carbene, 1,3-dimethylimidazolium-2-carboxylate (DMI-CO2 ), was investigated as a "green" and inexpensive organocatalyst for the alkylation of phenols. The process made use of various low-toxicity and renewable alkylating agents, such as dimethyl- and diethyl carbonate, in a focused microwave reactor. DMI-CO2 was found to be a very active catalyst and excellent yields of a range of aryl alkyl ethers were obtained under relatively benign conditions. The observed difference in the conversion behavior of phenol methylation, in the presence of either the carbene or 1,8-diazabicycloundec-7-ene (DBU) catalyst, was rationalized on the basis of mechanistic investigations. The primary mode of action for the N-heterocyclic carbene is nucleophilic catalysis. Activation of the dialkyl carbonate electrophile results in concomitant evolution of an organo-soluble alkoxide, which deprotonates the phenolic starting material. In contrast, DBU is initially protonated by the phenol and thus consumed. Subsequent regeneration and participation in nucleophilic catalysis only becomes significant after some phenolate alkylation occurs.

Chemcatchem, Jun 26, 2017

The catalytic depolymerization of Kraft lignin in supercritical ethanol was explored in the prese... more The catalytic depolymerization of Kraft lignin in supercritical ethanol was explored in the presence of Mo2C-and MoS2-based catalysts. At 280 °C, Mo2C and Mo2C/Al2O3 afforded aromatic yields of 425 and 419 mg/g lignin, respectively: amongst the highest yields reported to date. Ionic-liquid-assisted delamination of MoS2 resulted in highly active catalysts, capable of quantitative conversion of lignin at the expense of aromatic yield (ca 186 mg/g lignin). Across all the catalysts studied, between 0.04 wt% and 0.38 wt% of molybdenum leached into solution under supercritical conditions, according to ICP analyses (corresponding to 27-570 µg of molybdenum in the reaction supernatant). A small contribution to the molybdenum in solution comes from the reactor itself (Hastelloy C contains 16 wt% Mo). Analysis of a depolymerization performed with fresh Kraft lignin and the soluble portion of the reaction mixture from a previous reactor run indicated that the leached species were neither active enough to afford the high conversions observed, nor selective enough to give high yields of aromatic products. In conjunction with the ICP data and differential chemoselectivities of the Mo2C-and MoS2-based catalysts, these results suggest that the bulk of the catalysis is heterogeneous.

ACS Sustainable Chemistry & Engineering, Jan 16, 2019

In this study, the extractive desulfurization of model fuel oil with ionic liquids (ILs) has been... more In this study, the extractive desulfurization of model fuel oil with ionic liquids (ILs) has been studied in an attempt to gain insights into the dominant forces controlling the extraction efficien...

European Journal of Organic Chemistry, Nov 26, 2018

A facile process for the methylation of phloroglucinol using environmentally friendly dimethyl ca... more A facile process for the methylation of phloroglucinol using environmentally friendly dimethyl carbonate as methylating agent and solvent is described. Widely available and inexpensive solid acids have been used as catalysts to promote this transformation. H-Y zeolite proved particularly selective for monomethylation, hence it has been used for the convenient preparation of methoxyresorcinol (MR), with only limited co-production of dimethoxyphenol (DMP). Conversely, the use of tungstosilic acid on silica easily afforded DMP in excellent isolated yield.

Energy & Fuels, Dec 9, 2016

Ionic Liquids (ILs) have been suggested as useful extractants of aromatic nitrogencontaining comp... more Ionic Liquids (ILs) have been suggested as useful extractants of aromatic nitrogencontaining compounds (N-compounds) from fuel oils. In this systematic study, ILs based on common cations and anions are employed as extractants of the archetypical N-compounds pyridine and indole from a model oil consisting of decane and toluene. The performance of these ILs as extractants of N-compounds is compared and rationalized. It is demonstrated that the cation and anion sizes (offering more surface area for extractants to interact) are the major

ChemSusChem, 2021

Dimethyl sulfide, a major byproduct of the Kraft pulping process, was used as an inexpensive and ... more Dimethyl sulfide, a major byproduct of the Kraft pulping process, was used as an inexpensive and sustainable catalyst/co‐reagent (methyl donor) for various methylations with dimethyl carbonate (as both reagent and solvent), which afforded excellent yields of O‐methylated phenols and benzoic acids, and mono‐C‐methylated arylacetonitriles. Furthermore, these products could be isolated using a remarkably straightforward workup and purification procedure, realized by dimethyl sulfide‘s neutral and distillable nature and the absence of residual salts. The likely mechanisms of these methylations were elucidated using experimental and theoretical methods, which revealed that the key step involves the generation of a highly reactive trimethylsulfonium methylcarbonate intermediate. The phenol methylation process represents a rare example of a Williamson‐type reaction that occurs without the addition of a Brønsted base.

ChemSusChem, 2020

Using lignin model compounds with relevant key characteristic structural features, the reaction p... more Using lignin model compounds with relevant key characteristic structural features, the reaction pathways of α-O-4 arylether linkages under hydrothermal conditions were elucidated. Our experimental results and computational modelling suggest that the α-O-4 linkages in lignin undergo catalyzed hydrolyses and eliminations to give phenolic and alkenylbenzene derivatives as major products in subcritical water. The decreased relative permittivity of water at these high temperatures and pressures facilitates the elimination reactions. The alkyl group on the α-carbon and the methoxy groups on the phenyl rings both have positive effects on the rate of conversion of α-O-4 linkages in native lignin.

ACS Sustainable Chemistry & Engineering, 2019

In this study, the extractive desulfurization of model fuel oil with ionic liquids (ILs) has been... more In this study, the extractive desulfurization of model fuel oil with ionic liquids (ILs) has been studied in an attempt to gain insights into the dominant forces controlling the extraction efficien...

European Journal of Organic Chemistry, 2018

A facile process for the methylation of phloroglucinol using environmentally friendly dimethyl ca... more A facile process for the methylation of phloroglucinol using environmentally friendly dimethyl carbonate as methylating agent and solvent is described. Widely available and inexpensive solid acids have been used as catalysts to promote this transformation. H‐Y zeolite proved particularly selective for monomethylation, hence it has been used for the convenient preparation of methoxyresorcinol (MR), with only limited co‐production of dimethoxyphenol (DMP). Conversely, the use of tungstosilicic acid on silica easily afforded DMP in excellent isolated yield.

ChemSusChem, May 29, 2017

Using both experimental and computational methods, focusing on intermediates and model compounds,... more Using both experimental and computational methods, focusing on intermediates and model compounds, some of the main features of the reaction mechanisms that operate during the hydrothermal processing of lignin were elucidated. Key reaction pathways and their connection to different structural features of lignin were proposed. Under neutral conditions, subcritical water was demonstrated to act as a bifunctional acid/base catalyst for the dissection of lignin structures. In a complex web of mutually dependent interactions, guaiacyl units within lignin were shown to significantly affect overall lignin reactivity.

ChemCatChem, 2017

The catalytic depolymerization of Kraft lignin in supercritical ethanol was explored in the prese... more The catalytic depolymerization of Kraft lignin in supercritical ethanol was explored in the presence of Mo2C-and MoS2-based catalysts. At 280 °C, Mo2C and Mo2C/Al2O3 afforded aromatic yields of 425 and 419 mg/g lignin, respectively: amongst the highest yields reported to date. Ionic-liquid-assisted delamination of MoS2 resulted in highly active catalysts, capable of quantitative conversion of lignin at the expense of aromatic yield (ca 186 mg/g lignin). Across all the catalysts studied, between 0.04 wt% and 0.38 wt% of molybdenum leached into solution under supercritical conditions, according to ICP analyses (corresponding to 27-570 µg of molybdenum in the reaction supernatant). A small contribution to the molybdenum in solution comes from the reactor itself (Hastelloy C contains 16 wt% Mo). Analysis of a depolymerization performed with fresh Kraft lignin and the soluble portion of the reaction mixture from a previous reactor run indicated that the leached species were neither active enough to afford the high conversions observed, nor selective enough to give high yields of aromatic products. In conjunction with the ICP data and differential chemoselectivities of the Mo2C-and MoS2-based catalysts, these results suggest that the bulk of the catalysis is heterogeneous.

ChemSusChem, Sep 8, 2016

An easily prepared masked N-heterocyclic carbene, 1,3-dimethylimidazolium-2-carboxylate (DMI-CO2 ... more An easily prepared masked N-heterocyclic carbene, 1,3-dimethylimidazolium-2-carboxylate (DMI-CO2 ), was investigated as a "green" and inexpensive organocatalyst for the alkylation of phenols. The process made use of various low-toxicity and renewable alkylating agents, such as dimethyl- and diethyl carbonate, in a focused microwave reactor. DMI-CO2 was found to be a very active catalyst and excellent yields of a range of aryl alkyl ethers were obtained under relatively benign conditions. The observed difference in the conversion behavior of phenol methylation, in the presence of either the carbene or 1,8-diazabicycloundec-7-ene (DBU) catalyst, was rationalized on the basis of mechanistic investigations. The primary mode of action for the N-heterocyclic carbene is nucleophilic catalysis. Activation of the dialkyl carbonate electrophile results in concomitant evolution of an organo-soluble alkoxide, which deprotonates the phenolic starting material. In contrast, DBU is initi...

Energy & Fuels, 2016

Ionic Liquids (ILs) have been suggested as useful extractants of aromatic nitrogencontaining comp... more Ionic Liquids (ILs) have been suggested as useful extractants of aromatic nitrogencontaining compounds (N-compounds) from fuel oils. In this systematic study, ILs based on common cations and anions are employed as extractants of the archetypical N-compounds pyridine and indole from a model oil consisting of decane and toluene. The performance of these ILs as extractants of N-compounds is compared and rationalized. It is demonstrated that the cation and anion sizes (offering more surface area for extractants to interact) are the major

ACS Sustainable Chemistry & Engineering, 2019

Structural Chemistry, 2016

Dry gamma-valerolactone (GVL) is stable for several weeks at 150°C and its thermal decomposition ... more Dry gamma-valerolactone (GVL) is stable for several weeks at 150°C and its thermal decomposition only proceeds in the presence of appropriate catalysts. Since GVL does not react with water up to 60°C for several weeks, it could be used as a green solvent at mild conditions. At higher temperatures, GVL reacts with water to form 4-hydroxyvaleric acid (4-HVA) and reaches the equilibrium in a few days at 100°C. Aqueous solutions of acids (HCl and H 2 SO 4) catalyze the ring opening of GVL even at room temperature, which leads to the establishment of an equilibrium between GVL, water, and 4-HVA. Although the 4-HVA concentration would be below 4 mol% in the presence of acids, it could be higher than the concentration of a reagent or a catalyst precursor, not to mention a catalytically active species. The latter could be especially worrisome as 4-HVA could be an excellent bi-or even a tri-dentate ligand for transition metals. Aqueous solution of bases (NaOH and NH 4 OH) also catalyzes the reversible ring opening of GVL. While in the case of NaOH, the product is the sodium salt of 4-hydroxyvalerate, the reversible reaction of GVL, with NH 4 OH results in the formation of 4-hydroxyvaleric amide. The reversible ring opening of (S)-GVL in the presence of HCl or NaOH has no effect on the stability of the chiral center.

Org. Chem. Front., 2014

Nonafluoro-t-butyl propyl (1), allyl (2), and propargyl (3) ethers as well as 1,2-bis(nonafluoro-... more Nonafluoro-t-butyl propyl (1), allyl (2), and propargyl (3) ethers as well as 1,2-bis(nonafluoro-t-butoxy)ethane (4), 1,3-bis(nonafluoro-t-butoxy)-propane (5), and 1,4-bis(nonafluoro-t-butoxy)-butane (6) were prepared by the reaction of sodium nonafluoro-t-butoxide (7) with the corresponding alkyl halides in good yields. Their fluorous partition coefficients and toxicity were also investigated. Computational studies have shown that 4, 5 and 6 exist in a monomeric form in MeOH–CF3C6F11 and they likely aggregate to form oligomers in PhCH3–CF3C6F11.

Chemical Science, 2011

ABSTRACT Solvents and solutions are ubiquitous in chemistry. For instance, in synthesis the solve... more ABSTRACT Solvents and solutions are ubiquitous in chemistry. For instance, in synthesis the solvent allows reagents to mix intimately so that reactions between these may occur. Consequently, understanding how solutes behave in solutions has been one of the major themes of chemistry throughout its history. Ionic liquids (liquid salts) are an exciting recent addition to the range of available solvents. Here we show that these solvents interact with dissolved salts to give solutions that are completely different from those of salts in either traditional organic solvents or water. Observations of these ideal salt solutions will require new models of solvation and polarity and have the potential to lead to new chemical processes.