5459-98-3Relevant articles and documents
Efficient Synthesis of Cyclic Carbonates from Unsaturated Acids and Carbon Dioxide and their Application in the Synthesis of Biobased Polyurethanes
Martínez, Javier,de la Cruz-Martínez, Felipe,Martínez de Sarasa Buchaca, Marc,Fernández-Baeza, Juan,Sánchez-Barba, Luis F.,North, Michael,Castro-Osma, José A.,Lara-Sánchez, Agustín
, p. 460 - 468 (2021/04/06)
Bio-derived furan- and diacid-derived cyclic carbonates have been synthesized in high yields from terminal epoxides and CO2. Furthermore, four highly substituted terpene-derived cyclic carbonates were isolated in good yields with excellent diastereoselectivity in some cases. Eleven new cyclic carbonates derived from 10-undecenoic acid under mild reaction conditions were prepared, providing the corresponding carbonate products in excellent yields. The catalyst system also performed the conversion of an epoxidized fatty acid n-pentyl ester into a cyclic carbonate under relatively mild reaction conditions (80 °C, 20 bar, 24 h). This bis(cyclic carbonate) was obtained in high yields and with different cis/trans ratios depending on the co-catalyst used. An allyl alcohol by-product was only observed as a minor product when bis(triphenylphosphine)iminium chloride was used as co-catalyst. Finally, two cyclic carbonates were used as building blocks for the preparation of non-isocyanate poly(hydroxy)urethanes by reaction with 1,4-diaminobutane.
Synthesis, characterization, and evaluation of 10-undecenoic acid-based epithio derivatives as multifunctional additives
Geethanjali, Gorla,Padmaja, Korlipara V.,Sammaiah, Arukali,Prasad, Rachapudi B. N.
, p. 11505 - 11511 (2015/02/19)
Novel epithio compounds from alkyl epoxy undecanoates (n-alkyl, C1, C4, and C6; isoalkyl, C3, C4, and C8) were synthesized using an ammonium thiocyanate in ionic liquid 1-methylimidazolium tetrafluoroborate/H2O (2:1) solvent system in 85-90% yields by gas chromatographic (GC) analysis. The synthesized products were characterized by 1H and 13C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy (FTIR), gas chromatography, and GC mass spectral (GC-MS) analyses and evaluated for their antioxidant, extreme pressure (EP), and antiwear (AW) properties in three different base oils, namely, epoxy jatropha fatty acid n-butyl esters (EJB), di-2-ethylhexyl sebacate (DOS), and mineral oil (S-105). Among the synthesized products, n-butyl epithio undecanoate exhibited superior antioxidant property (229.2 °C) compared to butylated hydroxytoluene (BHT, 193.8 °C) in base oil DOS and comparable performance in EJB and S-105 base oils. All of the epithio derivatives exhibited significantly enhanced weld point for the base oils EJB and DOS at 2 wt % level and displayed moderate enhancement in S-105 base oil. Methyl epithio undecanoate at 0.6% concentration exhibited considerable improvement in the wear scar of DOS base oil. The synthesized epithio derivatives have potential as multifunctional additives in lubricant formulations.
Convenient formation of 4-hydroxyalk-2-en-1-one functionality via a Knoevenagel-type carbon chain elongation reaction of aldehyde with 1-arylsulfinylalkan-2-one
Nokami,Kataoka,Shiraishi,Osafune,Hussain,Sumida
, p. 1228 - 1232 (2007/10/03)
A highly functionalized four-carbon unit, 4-hydroxyalk-2-en-1-one functionality [R2CH(OH)CH= CHCOR1], was conveniently prepared by a reaction of an aldehyde (R2CH2CHO) with a 1-(arylsulfinyl)alkan-2-one [ArS(O)CH2COR1] in the presence of diethylamine (Knoevenagel condition). Other functional groups, such as carbonyl and hydroxy groups, in both of the alkyl chains (R1, R2) did not prevent this reaction. This reaction was used to conveniently prepare (±)-(11E)-13-hydroxy-10-oxooctadec-11-enoic acid (14), having cytotoxic activity, and its analogues from undec-10-enoic acid in good yield.
