51238-94-9Relevant academic research and scientific papers
Direct synthesis of adipic acid esters via palladium-catalyzed carbonylation of 1,3-dienes
Yang, Ji,Liu, Jiawang,Neumann, Helfried,Franke, Robert,Jackstell, Ralf,Beller, Matthias
, p. 1514 - 1517 (2020/01/08)
The direct carbonylation of 1,3-butadiene offers the potential for a more cost-efficient and environmentally benign route to industrially important adipic acid derivatives. However, owing to the complex reaction network of regioisomeric carbonylation and isomerization pathways, a selective practical catalyst for this process has thus far proven elusive. Here, we report the design of a pyridyl-substituted bidentate phosphine ligand (HeMaRaphos) that, upon coordination to palladium, catalyzes adipate diester formation from 1,3-butadiene, carbon monoxide, and butanol with 97% selectivity and 100% atom-economy under industrially viable and scalable conditions (turnover number > 60,000). This catalyst system also affords access to a variety of other di- and triesters from 1,2- and 1,3-dienes.
The synthesis of di-carboxylate esters using continuous flow vortex fluidics
Britton, Joshua,Dalziel, Stuart B.,Raston, Colin L.
, p. 2193 - 2200 (2016/04/19)
A vortex fluidic device (VFD) is effective in mediating the synthesis of di-esters at room temperature. Processing under ambient conditions allows for a simple and efficient synthesis, whilst operating under continuous flow addresses scalability. The rotational speed of the sample tube and the flow rate were critical variables during reaction optimization, and this relates to the behaviour of the fluid flow at a molecular level. Whilst at specific rotational speeds the tube imparts a vibrational response into the fluid flow, the flow rate dictates residence time and the ability to maintain high levels of shear stress. The combination of mechanically induced vibrations, rapid micromixing, high levels of shear stress and water evaporation results in yields up to 90% for 3.25 minutes or less residence time. These results are key for devising greener and more efficient processes both mediated by the VFD and other continuous flow platforms.
Oxidation of cycloalkanones with hydrogen peroxide: an alternative route to the Baeyer-Villiger reaction. Synthesis of dicarboxylic acid esters
Terent'ev, Alexander O.,Platonov, Maxim M.,Kashin, Alexey S.,Nikishin, Gennady I.
, p. 7944 - 7948 (2008/12/21)
The acid-catalyzed oxidation of cycloalkanones C5-C8 and C12 with hydrogen peroxide in alcohols was performed, and dicarboxylic acid esters were obtained as the major products in 53-70% yields. In the first step, geminal bishydroperoxides are generated from five-to-seven-membered cyclic ketones. The Baeyer-Villiger reaction is a side process accompanied by the formation of ω-hydroxycarboxylic acid esters.
Process for the preparation of pimelic esters
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, (2008/06/13)
A method is provided for the preparation of a pimelic ester of the formula: STR1 wherein R1 and R2 may be identical or different, and are linear or branched saturated alkyl substituents having from 1 to 10 carbons or araliphatic radicals having 7 to 10 carbon atoms; R3 is H or a hydrocarbon radical of one to six carbon atoms, and n is an integer of from 0 to 3; wherein the method entails: reacting a salt, formed from reaction of a 2-oxocyclohexanecarboxylic ester with a strong base, with an alcohol at a temperature of 50°-250° C., to cause ring opening.
