16090-77-0Relevant articles and documents
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.
Selective monoesterification of dicarboxylic acids catalysed by ion-exchange resins
Nishiguchi, Takeshi,Ishii, Yasuhiro,Fujisaki, Shizuo
, p. 3023 - 3027 (2007/10/03)
Symmetrical dicarboxylic acids with 4-14 carbon atoms gave selectively the corresponding monoesters in high yields in the transesterification catalysed by strongly acidic ion-exchange resins in ester-hydrocarbon mixtures. It was found that the rate of the esterification of the dicarboxylic acids is much higher than that of the monocarboxylic acids formed. This result can explain the high selectivity for the monoester formation and can also be explained by the existence of an aqueous layer on the surface of the resins. This method of selective esterification is quite simple and practical. The Royal Society of Chemistry 1999.
Convenient selective monoesterification of α, ω-dicarboxylic acids catalyzed by ion-exchange resins
Saitoh, Masahiko,Fujisaki, Shizuo,Ishii, Yasuhiro,Nishiguchi, Takeshi
, p. 6733 - 6736 (2007/10/03)
Symmetric dicarboxylic acids, ranging from pentanedioic acid to tetradecanedioic acid, gave selectively the corresponding monoesters in high yields in the transesterification catalyzed by strongly acidic ion-exchange resins in ester/octane mixtures.
Cosmetic composition
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, (2008/06/13)
A composition suitable for topical application to mammalian skin or hair for inducing, maintaining or increasing hair growth comprises: (i) a first chemical inhibitor chosen from proteoglycanase inhibitors, glycosaminoglycanase inhibitors, glycosaminoglycan chain cellular uptake inhibitors or mixtures thereof; and (ii) a cosmetically acceptable vehicle for the chemical inhibitor; provided that when the first chemical inhibitor is a weak inhibitor, such that a 1 mM aqueous solution of the inhibitor reduces proteoglycanase activity, glycosaminoglycanase activity or cellular uptake of glycosaminoglycan chains, by from 5 to 50%, in accordance with at least one of the assay tests as herein described, then there is also present in the composition a second chemical inhibitor and/or an activity enhancer. When minoxidil is the sole chemical inhibitor, then the activity enhancer is a penetration enhancer chosen from a limited number of materials, including certain esters and cationic polymers. The total amount of chemical inhibitor present in the composition is sufficient to increase hair growth in the rat, when said composition is applied topically thereto, by at least 10% more than that obtainable using a control composition from which the said inhibitors have been omitted.
PALLADIUM(0) AND RHODIUM(I) CATALYSIS OF THE CARBONYLATION OF UNACTIVATED BROMIDES
Hashem, Khaled E.,Woell, James B.,Alper, Howard
, p. 4879 - 4880 (2007/10/02)
Alkyl, vinyl, and aromatic bromides react with organoborates and carbon monoxide, in the presence of catalytic quantities of 1,5-hexadienerhodium(I) chloride dimer and tetrakis(triphenylphosphine)palladium(0), to give carboxylic esters in good yields.
