We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Catalytic Oxyfunctionalization of Methyl 10-undecenoate for the Synthesis of Step-Growth Polymers.
- Authors
Czapiewski, Marc; Meier, Michael A. R.
- Abstract
An efficient synthesis strategy for the preparation of two renewable polyesters and one renewable polyamide via catalytic oxyfunctionalization of methyl 10-undecenoate, a castor oil derived platform chemical, is described. The keto-fatty acid methyl ester (keto-FAME) is synthesized applying a cocatalyst-free Wacker oxidation process using a high-pressure reactor system. For this purpose, catalytic amounts of palladium chloride are used in the presence of a dimethylacetamide/water mixture and molecular oxygen as sole reoxidant. The thus derived AB monomers (hydroxy-esters, amine-ester) are synthesized from the obtained keto-FAME through Baeyer-Villiger oxidation and subsequent transesterification, reduction, or reductive amination, respectively. The resulting AB step-growth monomers are then studied in homopolymerizations using 1,5,7-triazabicyclo[ 4.4.0]dec-5-ene, DBU, and titanium(IV) isopropoxide as transesterification catalyst, yielding polymers with molecular weights (Mn) up to 15 kDa. The polyesters and the polyamide are carefully characterized by FTIR, SEC, ¹H-NMR spectroscopy, and differential scanning calorimetry analysis.
- Subjects
POLYCONDENSATION; POLYESTERS; PALLADIUM catalysts; CASTOR oil; FATTY acids; METHYL formate
- Publication
Macromolecular Chemistry & Physics, 2017, Vol 218, Issue 16, p1
- ISSN
1022-1352
- Publication type
Article
- DOI
10.1002/macp.201700153