335097-03-5Relevant academic research and scientific papers
Synthesis of tertiary and quaternary amine derivatives from wood resin as chiral NMR solvating agents
Laaksonen, Tiina,Heikkinen, Sami,W?h?l?, Kristiina
, p. 20873 - 20886 (2015/12/23)
Chiral tertiary and quaternary amine solvating agents for NMR spectroscopy were synthesized from the wood resin derivative (+)-dehydroabietylamine (2). The resolution of enantiomers of model compounds [Mosher's acid (3) and its n-Bu4N salt (4)] (guests) by (+)-dehydroabietyl-N,N-dimethylmethanamine (5) and its ten different ammonium salts (hosts) was studied. The best results with 3 were obtained using 5 while with 4 the best enantiomeric resolution was obtained using (+)-dehydroabietyl-N,N-dimethylmethanaminium bis(trifluoromethane-sulfonimide) (6). The compounds 5 and 6 showed a 1:1 complexation behaviour between the host and guest. The capability of 5 and 6 to recognize the enantiomers of various α-substituted carboxylic acids and their n-Bu4N salts in enantiomeric excess (ee) determinations was demonstrated. A modification of the RES-TOCSY NMR pulse sequence is described, allowing the enhancement of enantiomeric discrimination when the resolution of multiplets is insufficient.
Biomass derived ionic liquids: Synthesis from natural organic acids, characterization, toxicity, biodegradation and use as solvents for catalytic hydrogenation processes
Ferlin, Nadège,Courty, Matthieu,Gatard, Sylvain,Spulak, Marcel,Quilty, Brid,Beadham, Ian,Ghavre, Mukund,Hai?, Annette,Kümmerer, Klaus,Gathergood, Nicholas,Bouquillon, Sandrine
, p. 6150 - 6161 (2013/07/25)
Ionic liquids with natural organic derived anions (l-lactate, l-tartrate, malonate, succinate, l-malate, pyruvate, d-glucuronate, d-galacturonate) were easily prepared from tetrabutylammonium hydroxide and an excess of the corresponding acid with good yields. Their characterization was realized through classical NMR, IR, and elemental analysis techniques; their viscosity and TGA (thermogravimetric analysis) parameters were also determined. These ionic liquids showed good performance and recyclability in the selective catalytic hydrogenation of 1,5-cyclooctadiene (1,5-COD) into cyclooctene (COD) at room temperature under atmospheric H2 pressure. Antimicrobial toxicity assays toward a large panel of bacteria and fungi strains were also completed and biodegradation studies (Closed Bottle test, 28 days) were also performed.
Chiral ionic liquids improved the asymmetric cycloaddition of CO 2 to epoxides
Zhang, Suling,Huang, Yongzhong,Jing, Huanwang,Yao, Weixuan,Yan, Peng
supporting information; experimental part, p. 935 - 938 (2010/04/23)
The new catalyst system of chiral SalenCo(OAc)/chiral ionic liquid was developed to catalyze the asymmetric cycloaddition reaction of CO2 and epoxides yielding the chiral cyclic carbonates. The synergistic effect between them is discussed.
