Undecylenic acid: A tunable bio-based synthon for materials applications

Synthesis and properties of allyl terminated renewable non-isocyanate polyurethanes (NIPUs) and polyureas (NIPUreas) and study of their photo-crosslinking

“…Three main approaches have been described: (i) The reaction of diamines with five-membered bicyclocarbonates leading to poly(hydroxylurethane)s [4][5][6][7][8][9][10][11][12][13][14][15][16][17]; (ii) the self-polycondensation of AB-type fatty monomers bearing hydroxyl and acyl azide groups, in the presence or absence of catalyst. The heating of acyl azide groups led to in situ formation of isocyanate groups via Curtius rearrangement [18][19][20][21]; (iii) the polycondensation by transurethanization consisting in the reaction between dicarbamates and diols, in the presence of a catalyst, especially 1,5,7-triazabicyclo [4.4.0]dec-5-ene (TBD) [22,23].…”

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO2 Utilization

“…This two-step procedure was preferred to the reaction of FDCA with epihalohydrins to avoid the formation of oligomeric byproducts (Scheme 11). [132] UA was treated with GD, leadingt of ormation of a vicinal diol, and with diethylc arbonate (DEC), leading to 2i. Synthesis of 4e from biomass-derived HMF.…”

“…[131] 4g was preparedb yP lasseraud and co-workerss tarting from undecylenic acid (UA), at erminally unsaturated fatty acid that can be obtained from the pyrolysis of the ricinoleic acid chains of castor oil (Scheme 12, route a). [132] UA was treated with GD, leadingt of ormation of a vicinal diol, and with diethylc arbonate (DEC), leading to 2i. Ruthenium-catalyzed self-metathesis of 2i led to 4g for application in PHUs synthesis.…”

“…Scheme12. Synthesis of 4g by two different approaches reported by Plasseraud and co-workers (Ref [132][133]…”

Self‐Metathesis of 10‐Undecen‐1‐Ol with Ru‐Amine‐Based Complex for Preparing the Soft Segment and Chain Extender of Novel Castor Oil‐Based Polyurethanes

“…Castor oil and its derivatives have been used to prepare PUs with good mechanical properties, comparable to those from petrochemical PU, and may find applications as wood adhesives, flexible foams, and hard elastomers . 10‐undecen‐1‐ol can be obtained from castor oil or ricinoleic acid by pyrolysis under vacuum and reduction with LiAlH 4 at 0 °C . The utilization of renewable resources favors environmental sustainability …”