64357-65-9Relevant academic research and scientific papers
Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream
Liu, Guangchang,Xu, Bo
, p. 869 - 872 (2018)
We have developed a metal and halogen-free Friedel–Crafts acylation protocol with virtually no waste stream generation. We propose a hydrogen bonding donor solvent will form a hydrogen bonding network and may provide significant rate enhancement for Friedel–Crafts reactions. Trifluoroacetic acid is one of the strongest H-bond donor solvents, which is also volatile and can be easily recovered by distillation without need for reaction workup. Our protocol is a ‘green’ Friedel–Crafts acylation process: 1) the catalyst can be recovered and reused; 2) using halogen free starting material (carboxylic acids anhydride or carboxylic acids); 3) no need for aqueous reaction work-up; 4) minimum or no waste steam generation.
Chloroindate(III) ionic liquids: Recyclable media for Friedel-Crafts acylation reactions
Earle, Martyn J.,Hakala, Ullastiina,Hardacre, Christopher,Karkkainen, Johanna,McAuley, Barry J.,Rooney, David W.,Seddon, Kenneth R.,Thompson, Julian M.,Waehaelae, Kristina
, p. 903 - 905 (2007/10/03)
Chloroindate(III) ionic liquids are versatile reaction media for Friedel-Crafts acylation reactions; the system is catalytic and totally recyclable, using an aqueous workup, with no leaching of the indium into the product phase. The Royal Society of Chemistry 2005.
Friedel-crafts benzoylation of alkylbenzenes with brazoic anhydride catalyzed by solid superacids
Nakamura, Hideo,Arata, Kazushi
, p. 1893 - 1896 (2007/10/03)
The liquid-solid phase benzoylation of mono-alkylbenzenes with methyl, ethyl, propyl, and butyl groups and xylenes was carried out with benzoic anhydride at 100-110°C over solid superacids: SO4/ZrO 2, WO3/ZrO2, and SO4/ HfO 2. The reactivity ratio obtained by the competitive method of reaction over WO3/ZrO2 was 1 to 4.6 for toluene to p-xylene and 1.1:10:1 among o-, m-, and p-xylenes, respectively. Although the SO4/ZrO2 catalyst gave high yields of 92 and 97% for toluene and ethylbenzene in a 3:7 distribution of o- and p-isomers, respectively, low yields were observed with propyl and butylbenzenes over the catalyst: that is, 5 and 2% for propylbenzene and isopropylbenzene, 14% for isobutylbenzene, and trace yields for butylbenzene, s-butylbenzene, and t-butylbenzene, respectively. The usual Friedel-Crafts benzoylation using AlCl3 was examined in the present alkylbenzenes in order to confirm the low reactivity of both propyl and butylbenzenes. The results were similar to those with the SO4/ZrO2 catalyst; that is, the yields at 0°C for 1 h were 37, 21, 6, 1, 0, 3, and 2% for toluene, ethylbenzene, propylbenzene, isopropylbenzene, butylbenzene, s-butylbenzene, and t-butylbenzene, respectively, showing an unexpected result where there was no distinction between homogeneous and heterogeneous conditions.
