Facile synthesis of fructone from ethyl acetoacetate and ethylene glycol catalyzed by SO3H-functionalized Brønsted acidic ionic liquids

Acidic Ionic Liquids

“…There are attempts to correlate calculated H 0 values of BAILs with catalysis activities in chemical reactions such as, Pechmann condensation, hydration of alkynes, Fischer indole synthesis, coupling of epoxides and CO 2 , alcoholysis of furfural alcohol to alkyl levulinates, esterification, − fructone synthesis, 2-phenylbenzimidazole synthesis, degradation of lignin model compounds, acetal synthesis and dehydration of fructose . In one instance H 0 values of a series of BAILs have been corelated to the yields and conversions in the synthesis of methylene diphenyl dimethyl carbamate (4,4′-MDC) from methyl N -phenyl carbamate (MPC) and formaldehyde (HCHO) as shown in Table .…”

“…Acetalization is another acid catalyzed reaction tested with BAILs, where (4-butylsulfonic)-triethylammonium hydrogensulfate [(HSO 3 ) 4 C 4 (C 2 ) 3 N]­[HSO 4 ] was reported to give excellent yields in the production of fructone via the acetalization reaction of ethyl acetoacetate with ethylene glycol. , The condensation of glycerol, a platform chemical from renewable materials with benzaldehyde to generate cyclic acetals has been investigated using BAIL catalysts. Evidence was presented for the formation of a product mixture with 4-hydroxymethyl-2-phenyl-1,3-dioxolane and 5-hydroxyl-2-phenyl-1,3-dioxane as cis and trans stereoisomers.…”

Preparation and testing of ceasium Brønsted ion-exchanged Al-SBA-15 supported heteropoly acid as heterogeneous catalyst in the fructone fragrancy synthesis

“…Fructone (also known as 2,4-dimethyl-2-ethylacetoacetate-1,2-dioxolan) is a synthetic apple fragrancy synthesised from the acetalisation reaction of ethyl acetoacetate (EAA) and diols substances using acid catalysts. Because of the commonly known disadvantages related to homogeneous acid catalysts such as difficult to separate and recover from the products, not be able to reuse, highly corrosive, expensive durable reactors are required [1,2], heterogeneous catalysts for fructone fragrancy synthesis such as SO3Hfunctionalised carbon [3], copolymer of p-toluenesulfonic acid and p-formaldehyde [4], mesoporous Al-SBA-15 [5] and ultra-stable Y zeolite supported heteropoly acid [6], and a type of ionic liquid catalyst as SO3Hfunctionalized BAILs [7] have been developed for easy recovery and reuse. Among these effective studied catalysts, the heteropoly acid (HPA) in α-Keggin form (H3PW12O40) has been of great interests due to the high acidity of this catalyst and its possibility to be heterogenised using various methods such as precipitation [8][9][10][11][12], hybridisation [13][14][15][16], dispersion [17][18][19][20][21], encapsulation [6,22,23], tethering [24][25][26] and grafting [27,28].…”

Conductivity, Viscosity, Spectroscopic Properties of Organic Sulfonic Acid solutions in Ionic Liquids

“…Sulfonic acids in ILs have various applications. First, sulfonic acid-based AILs have been used as solvents and catalysts for Fischer esterification reactions and for alcohol, amine, and starch acetylation reactions [10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26]. When AILs are used in these reactions, they are "bi-functional", as solvents and homogeneous catalysts.…”