54248-02-1Relevant 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.
REACTION BEHAVIOR OF CARBON-CARBON AND CARBON-HYDROGEN BONDS IN SUPER ACIDS. CARBOXYLATION OF ALKYL METHYL KETONES WITH CARBON MONOXIDE AND WATER
Yoneda, Norihiko,Sato, Haruhiko,Fukuhara, Tsuyoshi,Takahashi, Yukio,Suzuki, Akira
, p. 19 - 20 (2007/10/02)
In a HF-SbF5 solution at -20 -ca.30 deg C under atmospheric pressure, ketones having alkyl groups with five or more carbon atoms underwent the reaction to give corresponding oxo carboxylic acids without any β-scission processes which occur readily in alkyl cations derived by protolysis of alkalnes with seven or more carbon atoms.Tertiary C-H bond located at δ or further away from the oxo group in the substrates could react exclusively to give (ω-1)-oxo-2,2-dimethyl carboxylic acids at -20 deg C.