title: Aliphatic long-chain C20 polyesters from olefin metathesis.
abstract: Self-metathesis of undecenoic acid with [(PCy3)2Cl2Ru=CHPh] (2), followed by exhaustive hydrogenation yielded pure 1,20-eicosanedioic acid (5) (>99%) free of side-products from isomerization. Polycondensation with eicosane-1,20-diol (6), formed by reduction of the diol, yielded polyester 20,20 (Tm = 108 °C). By comparison, the known ADMET polymerization of undec-10-enyl undec-10-enoate (7), and subsequent exhaustive polymer-analogous hydrogenation yielded a polyester (poly-8) with irregular structure of the ester groups in the polymer chain (-O(C=O)- vs. -C(=O)O-) (Tm = 103 °C). Hydrogenation of secondary dispersions of poly-7 yielded aqueous dispersions of the long-chain aliphatic polyester poly-8.
authors.affiliation: Chair of Chemical Materials Science, Department of Chemistry Universitätsstrasse 10, 78457 Konstanz, Germany.
authors.forename: Justyna
authors.initials: J
authors.lastname: Trzaskowski
authors.forename: Dorothee
authors.initials: D
authors.lastname: Quinzler
authors.forename: Christian
authors.initials: C
authors.lastname: Bährle
authors.forename: Stefan
authors.initials: S
authors.lastname: Mecking
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D006865:Hydrogenation; D011091:Polyesters / Q000138:chemical synthesis*; D058105:Polymerization; D012277:Ricinoleic Acids / Q000737:chemistry; D014476:Undecylenic Acids / Q000737:chemistry*
chemical_list: D000475:Alkenes; D011091:Polyesters; D012277:Ricinoleic Acids; D014476:Undecylenic Acids; C030521:ricinoleic acid; C538763:undecylenic acid