Metathetic alkenolysis of unsaturated units in polymers and copolymers––application to the synthesis of epoxy-functionalized oligomers and organic compounds

Depolymerization of 20% epoxidized cis-1,4-polybutadiene was carried out through alkenolysis of the butadiene repeat units (B) using 4-octene as depolymerizing agent (DA) and bis(tricyclohexyl phosphine)benzylidene ruthenium (IV) dichloride ( 1) as catalyst. The average molecular weight of the depol...

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Bibliographic Details
Published in:European polymer journal 2004-11, Vol.40 (11), p.2611-2616
Main Authors: Thanki, Paragkumar N., Reyx, Danièle, Campistron, Irène, Laguerre, Albert, Singh, Raj Pal
Format: Article
Language:English
Subjects:
Applied sciences
Chemical reactions and properties
Constructive degradation
Degradation
Epoxidized polybutadiene
Exact sciences and technology
Functional dienes
Grubbs catalyst
Metathesis alkenolysis
Organic polymers
Physicochemistry of polymers
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Summary:Depolymerization of 20% epoxidized cis-1,4-polybutadiene was carried out through alkenolysis of the butadiene repeat units (B) using 4-octene as depolymerizing agent (DA) and bis(tricyclohexyl phosphine)benzylidene ruthenium (IV) dichloride ( 1) as catalyst. The average molecular weight of the depolymerization products was determined by NMR, and SEC, and their constituents were identified by GC MS. Cis-4-octene was found more efficient in performing the depolymerization as compared to its trans isomer. Besides dodeca-4,8-diene and hexadeca-4,8,12-triene, 2,3-di[3-heptenyl]-oxirane with a cis oxirane configuration was clearly characterized. Beside the DA to B mole ratio, the catalyst to double bond mole ratio was observed as the major factor controlling the molecular weight of the depolymerization products and the 2,3-di[3-heptenyl]-oxirane yields.
ISSN:0014-3057
1873-1945
DOI:10.1016/j.eurpolymj.2004.06.029