Ionic Liquids as Phase-Transfer Catalysts: Etherification Reaction of 1-Octanol with 1-Chlorobutane

Abstract

Various ionic liquids have been examined along with some traditional phase-transfer catalysts, such as Aliquat reagents, in a standard liquid−liquid phase-transfer catalysis (LLPTC) reaction. A standard O-alkylation LLPTC reaction was chosen because of its relatively high yields and low incident of reaction side products. As expected, quaternary tetraalkyl ammonium catalysts all resulted in high conversion to product. Aliquat HTA-1, a high temperature phase-transfer catalyst normally used in nonaqueous reactions, resulted in yields only slightly higher than the noncatalyzed reaction. Substituted pyrrolidinium salts had relatively good catalytic activity, while substituted pyridinium and imidazolium catalysts showed either very little or no catalytic activity. Catalysts with fixed cationic charges resulted in high conversion for the etherification reactions; however, compounds with an aromatic π-bonding system were not suitable as phase-transfer catalysts.

Thiazolium‐Based Catalysts for the Etherification of Benzylic Alcohols under Solvent‐Free Conditions

“…Recently, Firouzabadi and co-workers reported the etherification of different classes of alcohols using catalytic amounts of the heteropolyacid AlPW 12 O 40 . [18][19][20][21] Elegant catalytic methods for etherification reactions are represented by the use of transition metals. Reductive etherification from carbonyl compounds can be achieved using organosilanes and Lewis acid catalysts such as BiCl 3 [12] or FeCl 3 .…”

Sunflower oil methanolisys and glycerol ketalisation: stepwise production of biofuels and additives with 3-methylimidazolium hydrogensulphate as catalyst

“…Some characteristics of these Brönsted acids brought our attention, for instance, their capacity to form hydrogen bonds with suitable Lewis bases 12 suggested that they should easily interact with glycerides and their derivatives. Also, the known ability of imidazol ionic liquids to serve as phase transfer agents 13 should be helpful to keep in contact the hard to mix substances of different polarities. These qualities prompted us to use the easily prepared Brönsted acidic 3-methylimidazolium hydrogensulfate as catalyst for a) the transesterification of sunflower oil, and b) the ketalisation of glycerol with acetone, two reactions which suffer from the poor solubility of triglycerides in methanol, and glycerol in acetone.…”

“…These qualities prompted us to use the easily prepared Brönsted acidic 3-methylimidazolium hydrogensulfate as catalyst for a) the transesterification of sunflower oil, and b) the ketalisation of glycerol with acetone, two reactions which suffer from the poor solubility of triglycerides in methanol, and glycerol in acetone. The known poor catalytic effect of imidazolium cations in etherification reactions 13 indicated that more drastic reaction conditions should be used, if the intended transesterification and ketalisation reactions were to be properly performed. Fortunately, we found that these extreme conditions resumed to methanol or acetone reflux temperatures, with reaction times up to 24 h, two factors that do not imparted the development of the combined processes.…”

Quaternary Ammonium and Phosphonium Ionic Liquids in Chemical and Environmental Engineering

“…Bender et al (2010) evaluated a series of ILs including Aliquat ® 336 as phase transfer catalysts for the etherification reaction of 1-octanol with 1-chlorobutane. The conversions ranged from 87-96% with Aliquat ® 336 catalysts.…”