Details

Project TitleBiorenewable, alpha-Pinene-Derived Monomer for Metathesis Polymerization
Track Code2015-120
Short Description

Northwestern researchers have developed an alternative method for using α-pinene as a monomer precursor for ROMP #chemical #additives #coatings #methods #materials #adhesives

Abstract

Northwestern researchers have developed an alternative method for using α-pinene as a monomer precursor for ROMP, a process traditionally known to produce significantly fewer byproducts with higher catalytic rates compared to other types of catalyzed polymerizations.  α-Pinene is the most abundant monoterpene present in nature and plays crucial roles in many biological, atmospheric, and industrial processes. Similar to other readily accessed and biorenewable terpenes, α-pinene is widely used in both the fine chemical and polymer industries. More specifically, the Lewis acid-catalyzed polymerization of α-pinene has found a variety of uses in industrial applications such as adhesives, plastics and rubbers.  α-Pinene is not suitable for ROMP due to the congested methyl-substituted olefin that hampers the polymerization reaction.  However, deleting the methyl substituent results in the less congested precursor, apopinene, which is suitable for subsequent polymerization reactions. Apopinene reacts with ruthenium-based metathesis catalysts to provide an all trans-polymer with a low polydispersity index and molecular weights in the 1100 to 15,600 g·mol−1 range (9−127 monomer units).  Northwestern researchers have developed a novel process to easily prepare apopinene in one-step from myrtenal or two-steps from α-pinene, both of which are naturally abundant. By utilizing this unique method, apopinene may find future use as a new biorenewable precursor for the sustainable production of ROMP-based materials and opens the opportunity to manufacture new families of polymers.

 
TagsCHEMICAL: additives, CHEMICAL: coatings, CHEMICAL: methods, MATERIALS: adhesives
 
Posted DateOct 27, 2016 3:28 PM

Inventor(s)

Massimiliano Delferro

Franz M Geiger

Benjamin F. Strick

Regan J. Thomson*

Applications

  • Rubber Additives
  • Lubricants
  • Adhesives
  • Coatings & Films
  • Sealants

Advantages

  • Abundance of α-pinene in nature
  • Potential expansion of product portfolio from readily available monomers
  • Easy preparation of apopinene from both α-pinene or myrtenal

Publications

Strick BF, Delferro M, Geiger FM, Thomson RJ (2015) Investigations into Apopinene as a Biorenewable Monomer for Ring-Opening Metathesis Polymerization. ACS Sustainable Chem. Eng.  3: 1278−1281.

IP Status

A provisional US patent application has been filed for the catalytic process and method of use.

Marketing Contact

Zachary Brown, PhD

Invention Associate

(p) 847.491.4629

(e) zachary.brown@northwestern.edu