5962-42-5Relevant articles and documents
Synthesis of Carboxylic Acids by Palladium-Catalyzed Hydroxycarbonylation
Sang, Rui,Kucmierczyk, Peter,Dühren, Ricarda,Razzaq, Rauf,Dong, Kaiwu,Liu, Jie,Franke, Robert,Jackstell, Ralf,Beller, Matthias
supporting information, p. 14365 - 14373 (2019/09/06)
The synthesis of carboxylic acids is of fundamental importance in the chemical industry and the corresponding products find numerous applications for polymers, cosmetics, pharmaceuticals, agrochemicals, and other manufactured chemicals. Although hydroxycarbonylations of olefins have been known for more than 60 years, currently known catalyst systems for this transformation do not fulfill industrial requirements, for example, stability. Presented herein for the first time is an aqueous-phase protocol that allows conversion of various olefins, including sterically hindered and demanding tetra-, tri-, and 1,1-disubstituted systems, as well as terminal alkenes, into the corresponding carboxylic acids in excellent yields. The outstanding stability of the catalyst system (26 recycling runs in 32 days without measurable loss of activity), is showcased in the preparation of an industrially relevant fatty acid. Key-to-success is the use of a built-in-base ligand under acidic aqueous conditions. This catalytic system is expected to provide a basis for new cost-competitive processes for the industrial production of carboxylic acids.
PHOSPHONYLATION BY TETRAPHOSPHORUS HEXOXIDE
Schuelke, Ulrich
, p. 623 - 626 (2007/10/02)
The general usefulness of P4O6 as starting material for the preparation of inorganic and organic phosphorus compounds is demonstrated by reactions of P4O6 with nucleophilic and electrophilic compounds.
Complexation Properties of Phosphonocarboxylic Acids in Aqueous Solutions
Farmer, Richard M.,Heubel, P.-H.C.,Popov, Alexander I.
, p. 523 - 532 (2007/10/02)
The concentration formation constants of phosphonoacetic acid (PAA) complexes with the Ca(2+) and Mg(2+) ions were determined in aqueous solution at 25 deg C by potentiometric and coulometric titrations at different ionic strengths and were extrapolated to I = 0 in order to obtain thermodynamic values of the formation constants.Complexes were formed by the completely deprotonated Kf(ML) and monoprotonated Kf(MHL) forms of the PAA anion.The respective values for the complexes are: log Kf(CaL) = 4.68 +/- 0.03, log Kf(CaHL) = 2.61 +/- 0.08; log Kf(MgL) = 5.58 +/- 0.09, log Kf(MgHL) = 3.0 +/- 0.3.The enthalpy and entropy of complexation for the deprotonated Ca(2+) and Mg(2+) PAA species, determined from the temperature dependence of the log Kf(ML), are: ΔHo(Ca) = 0.6 +/- 0.2 kcal-mol-1, ΔSo(Ca) = 21.4 +/- 0.6 cal-mol-1-K-1, ΔHo(Mg) = 3.0 +/- 0.7 kcal-mol-1, and ΔSo(Mg) = 35 +/- 2 cal-mol-1-K-1.It is seen therefore, that the complexes are entropy stabilized but enthalpy destabilized.Formation constants were also determined for Ca(2+) and Mg(2+) complexes with PAA analogs, phosphonoformic and 3-phosphonopropionic acids and the complexation of PAA was also studied at a single ionic strength, with Na(1+), Ag(1+), Tl(1+), Sr(2+), Ba(2+), Cd(2+), Cu(2+), and Pb(2+) ions.
