Epoxidation of Soybean Oil Catalyzed by Deep Eutectic Solvents Based on the Choline Chloride–Carboxylic Acid Bifunctional Catalytic System
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Abstract:
Deep eutectic solvents based on choline chloride–carboxylic acids, as a low-cost effective bifunctional catalyst, were successfully used to catalyze epoxidation of soybean oil with peroxyformic acid as the oxygen supplier under solvent-free conditions. The influence of reaction temperature and time on the epoxidation process evaluated by 1H nuclear magnetic resonance (NMR) quantitative analysis was extensively investigated. The optimal mild conditions were 50 °C and 8 h for choline chloride–oxalic acid dihydrate with 88.80% conversion of double bonds and a high selectivity of 93.86%. Meanwhile, choline chloride–malonic acid at 50 °C for 10 h exhibited better catalytic performance, 90.87% selectivity versus only 83.52% in the choline chloride–citric acid monohydrate system for 8 h. The epoxy products analyzed simultaneously by 1H NMR and the titration method were characterized in Fourier transform infrared, 13C NMR, and thermogravimetric analysis. The results suggested choline chloride–oxalic acid dihydrate with a favorable recyclability was more efficient for the promotion of epoxidation of soybean oil.Keywords:
Choline chloride
Oxalic Acid
Deep eutectic solvent
Thermogravimetric analysis
A series of 3-substituted-2-thioxo-2,3-dihydroquinazolin-4(1H)-ones and 6-iodo-3-substituted-2-thioxo-2,3-dihydroquinazolin-4(1H)-ones were synthesized in choline chloride/urea deep eutectic solvent. Substituted 2-mercapto-4(3H)-quinazolinones were synthesized from anthranilic acid or 5-iodoanthranilic acid and appropriate isothiocyanates in good to excellent yields. Isolation of final product was easy and required no further purification. Synthesis of these compounds was rapid, selective, and catalyst free, while preparation of deep eutectic solvent was easy, components are readily available, cheap, and environmentally friendly.
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Deep eutectic solvent
Environmentally Friendly
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Choline chloride
Deep eutectic solvent
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The HKUST-1 MOF can not only be synthesized in the green deep eutectic solvent reline (choline chloride/urea 1 : 2) but also converts, upon heating in reline, to a 2D non-porous structure incorporating chloride anions.
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Choline chloride
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Deep eutectic solvent of choline chloride-urea was used as a sustainable pre-treatment media prior mechanical nanofibrillation of wood cellulose.
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Deep eutectic solvent
Choline
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The structure of 1 : 2 choline chloride : urea (reline) deep eutectic solvent has been determined, showing extensive hydrogen bonding between all species.
Choline chloride
Deep eutectic solvent
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A series of 13 aryl indeno[2′,1′:5,6]pyrido[2,3- d]pyrimidine-2,4,6-(3 H,5 H,11 H)-triones, eight of which are new, were synthesised regioselectively in high yields by a three-component reaction of 1,3-indanedione, an araldehyde and 6-aminopyrimidin-2,4(1 H,3 H)-dione in the presence of a deep eutectic solvent comprised of choline chloride/urea (1:2) as the catalyst. The reaction conditions were mild and did not require additional catalysts. Given the inexpensive, nontoxic and recyclable nature of the deep eutectic solvent, these reaction conditions are simple to carry out and environmentally friendly.
Choline chloride
Deep eutectic solvent
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