Journal
MACROMOLECULAR RAPID COMMUNICATIONS
Volume 32, Issue 17, Pages 1338-1342Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/marc.201100104
Keywords
cascade reaction; cyclohexadiene (CHD); isomerization; metathesis; renewable resources
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Funding
- American Chemical Society
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Synthesis and subsequent polymerization of renewable 1,3-cyclohexadiene (1,3-CHD) from plant oils is reported via metathesis and isomerization reactions. The metathesis reaction required no plant oil purification, minimal catalyst loading, no organic solvents, and simple product recovery by distillation. After treating soybean oil with a ruthenium metathesis catalyst, the resulting 1,4-cyclohexadiene (1,4-CHD) was isomerized with RuHCl(CO)(PPh3)(3). The isomerization reaction was conducted for 1 h in neat 1,4-CHD with [1,4-CHD]/[RuHCl(CO)(PPh3)(3)] ratios as high as 5 000. The isomerization and subsequent polymerization of the renewable 1,3-CHD was examined as a two-step sequence and as a one-step cascade reaction. The polymerization was catalyzed with nickel(II) acetylacetonate/methaluminoxane in neat monomer, hydrogenated d-limonene, and toluene. The resulting polymers were characterized by FTIR, DSC, and TGA.
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