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Aliphatic Long‐Chain C 20 Polyesters from Olefin Metathesis
Author(s) -
Trzaskowski Justyna,
Quinzler Dorothee,
Bährle Christian,
Mecking Stefan
Publication year - 2011
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201100319
Subject(s) - polyester , diol , metathesis , polymer chemistry , polymerization , condensation polymer , isomerization , polymer , chemistry , aqueous solution , olefin metathesis , acyclic diene metathesis , organic chemistry , materials science , catalysis
Self‐metathesis of undecenoic acid with [(PCy 3 ) 2 Cl 2 RuCHPh] ( 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 ( T m = 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(CO) vs. C(O)O) ( T m = 103 °C). Hydrogenation of secondary dispersions of poly ‐7 yielded aqueous dispersions of the long‐chain aliphatic polyester poly‐ 8 .
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