US EPA

4944638 

Journal Article 

Isomerization-hydroboration-oxidation strategy: Access to long chain AB- and AA-type oleyl based monomers and polymers thereof 

Sane, P; Lebarbe, T; Grau, E; Cramail, H 

2016 

1 

European Journal of Lipid Science and Technology
ISSN: 1438-7697
EISSN: 1438-9312 

Wiley Subscription Services, Inc. 

118 

11 (Nov 2016) 

1620 

English 

10.1002/ejlt.201600064 

WOS:000387397700002 

 



A strategy to convert by isomerization-hydroboration-oxidation reaction the internal double bond of oleic acid to a terminal alcohol function, leading to linear long-chain [alpha],[omega]-difunctional substrates has been investigated. Using this strategy, oleic acid-based AB- and AA-monomers were prepared and characterized by FTIR-ATR and NMR spectroscopy. Thermoplastic aliphatic linear polyesters, polycarbonates, and polyurethanes were then synthesized by reacting the so-formed bio-based monomers via polycondensation in bulk, using 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as an organocatalyst. Thus, starting from easily available bio-based starting compound, the synthesis of linear long methylene chain aliphatic polyesters, polycarbonates, and polyurethanes (by isocyanate free route) is reported. The structural and thermal characterizations of the synthesized polymers were performed by means of NMR, SEC, DSC, and TGA experiments.


Practical applications: The objective of the work is to obtain long methylene sequence alpha, omega difunctional fatty acid-based substrates that can be used as original monomers.


A strategy to convert by isomerization-hydroboration-oxidation reaction the internal double bond of oleic acid to a terminal alcohol function, leading to linear long-chain [alpha],[omega]-difunctional substrates is described. 

Fatty acids; Alcohol; Oxidation