Synthesis and polymerization of renewable 1,3-cyclohexadiene using metathesis, isomerization, and cascade reactions with late-metal catalysts

Robert Timothy Mathers, Michael J. Shreve, Etan Meyler, Krishnan Damodaran, David F. Iwig, Diana J. Kelley

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

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)(PPh 3) 3] ratios as high as 5 000. The isomerization and subsequent polymerization of the renewable 1,3-CHDwas 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.

Original languageEnglish (US)
Pages (from-to)1338-1342
Number of pages5
JournalMacromolecular Rapid Communications
Volume32
Issue number17
DOIs
StatePublished - Sep 1 2011

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Isomerization
Plant Oils
Metals
Polymerization
Carbon Monoxide
Catalysts
Soybean oil
Soybean Oil
Ruthenium
Toluene
Nickel
Distillation
Organic solvents
Purification
Polymers
Monomers
Recovery
1,3-cyclohexadiene
1,4-cyclohexadiene
Oils

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

Cite this

Mathers, Robert Timothy ; Shreve, Michael J. ; Meyler, Etan ; Damodaran, Krishnan ; Iwig, David F. ; Kelley, Diana J. / Synthesis and polymerization of renewable 1,3-cyclohexadiene using metathesis, isomerization, and cascade reactions with late-metal catalysts. In: Macromolecular Rapid Communications. 2011 ; Vol. 32, No. 17. pp. 1338-1342.
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Synthesis and polymerization of renewable 1,3-cyclohexadiene using metathesis, isomerization, and cascade reactions with late-metal catalysts. / Mathers, Robert Timothy; Shreve, Michael J.; Meyler, Etan; Damodaran, Krishnan; Iwig, David F.; Kelley, Diana J.

In: Macromolecular Rapid Communications, Vol. 32, No. 17, 01.09.2011, p. 1338-1342.

Research output: Contribution to journalArticle

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