7268-65-7Relevant academic research and scientific papers
Linear semicrystalline polyesters from fatty acids by complete feedstock molecule utilization
Quinzler, Dorothee,Mecking, Stefan
, p. 4306 - 4308 (2010)
(Figure Presented) Complete and linear incorporation of fatty acids into polyesters is achieved by isomerizing carbonylation to give polymerization- quality diesters and their polycondensation with the corresponding diols obtained by reduction. The strictly linear and long-chain hydrocarbon nature of these polyesters results in a high degree of crystallinity and melting behavior akin to common thermoplastics.
A new route to α,ω-diamines from hydrogenation of dicarboxylic acids and their derivatives in the presence of amines
Shi, Yiping,Kamer, Paul C. J.,Cole-Hamilton, David J.
supporting information, p. 5460 - 5466 (2017/11/22)
A new and selective route for the synthesis of polymer precursors, primary diamines or N-substituted diamines, from dicarboxylic acids, diesters, diamides and diols using a Ru/triphos catalyst is reported. Excellent conversions and yields are obtained under optimised reaction conditions. The reactions worked very well using 1,4-dioxane as solvent, but the greener solvent, 2-methyl tetrahydrofuran, also gave very similar results. This method provides a potential route to converting waste biomass to value added materials. The reaction is proposed to go through both amide and aldehyde pathways.
Polymer precursors from catalytic reactions of natural oils
Furst, Marc R. L.,Goff, Ronan Le,Quinzler, Dorothee,Mecking, Stefan,Botting, Catherine H.,Cole-Hamilton, David J.
experimental part, p. 472 - 477 (2012/04/10)
Dimethyl 1,19-nonadecanedioate is produced from the methoxycarbonylation of commercial olive, rapeseed or sunflower oils in the presence of a catalyst derived from [Pd2(dba)3], bis(ditertiarybutylphosphinomethyl)benzene (BDTBPMB) and methanesulphonic acid (MSA). The diester is then hydrogenated to 1,19-nonadecanediol using Ru/1,1,1-tris-(diphenylphosphinemethyl)ethane (triphos). 1,19-Nonadecadienoic acid is hydrogenated to short chain oligoesters, which can themselves be hydrogenated to 1,19-nonadecanol by hydrogenation in the presence of water.
α,ω-functionalized C19 monomers
Walther, Guido,Deutsch, Jens,Martin, Andreas,Baumann, Franz-Erich,Fridag, Dirk,Franke, Robert,K?ckritz, Angela
experimental part, p. 1052 - 1054 (2012/04/11)
High-oleic sunflower oil, a renewable resource, is efficiently incorporated into a sustainable and green chemical process: the synthesis of α,ω-functionalized C19 monomers. These monomers, derived from dimethyl 1,19-nonadecanedioate as a novel platform chemical, may find use as feedstock materials for the polymer industry.
Long-chain linear C19 and C23 monomers and polycondensates from unsaturated fatty acid esters
Stempfle, Florian,Quinzler, Dorothee,Heckler, Ilona,Mecking, Stefan
experimental part, p. 4159 - 4166 (2012/05/04)
Isomerizing alkoxycarbonylation of methyl oleate and ethyl erucate, respectively, yielded dimethyl 1,19-nonadecanedioate and diethyl 1,23-tricosanedioate in >99% purity. With [κ2-(P P)Pd(OTf)][OTf] as a defined catalyst precursor (PP = 1,2-bis[(di-tert- butylphosphino)methyl]benzene) the reaction can be carried out without the need for additional added diphosphine. Saponification of the diesters yielded 1,19-nonadecanedicarboxylic acid and 1,23-tricosanedicarboxylic acid in >99% purity. By ruthenium-catalyzed reduction of the diesters with H2, 1,19-nonadecanediole and 1,23-tricosanediole were formed in high yield and purity (>99%). From the latter, 1,19-nonadecanediamine and 1,23-tricosanediamine were generated. Polyesters with commercially available shorter-chain petrochemical or renewable diols exhibit high melting points due to the crystallizable long-chain methylene segments from the dicarboxylic acid component, e.g., poly[1,6-hexadiyl-1,23-tricosanedioate] Tm 92, Tc 75 °C. Thermal properties of novel long-chain polyamides are reported.
