Office for Technology Commercialization

Methacrylate and Lactone Monomers Recycled from Renewable Malic Acid-Based Polyester

Technology #20180118

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Malic Acid Polymer
Thomas R. Hoye, PhD
Professor, College of Science and Engineering
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Managed By
Larry Micek
Technology Licensing Officer 612-624-9568
Patent Protection

Provisional Patent Application Filed
A Carbomethoxylated Polyvalerolactone from Malic Acid: Synthesis and Divergent Chemical Recycling
ACS Macro Letters, 2018, 7, pp 143–147
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Non-confidential Summary [DOCX]

Versatile Malic Acid-Based Lactone Monomer and Polyester

Malic acid is converted in two steps to 4-carboxymethylvalerolactone (CMVL), which can be polymerized to make a polyester. The polymer can be chemically recycled, via two different pathways, into two different monomers. One de-polymerization mechanism yields the original, renewable monomer, CMVL feedstock, and the other cleaves the polyester to create a methacrylate derivative that can be polymerized radically to afford a new polymethacrylate. This is a rare, perhaps first, example of a polymer that shows two independent chemical recycling pathways to two different classes of monomers.

Polymers can be Chemically Recycled

Current methods of disposing of plastics are commonly unsustainable and contribute to detrimental environmental and economic effects. To mitigate these effects, this new technology uses chemical or feedstock recycling, where a polymer is broken down into its monomer constituents for use in re-manufacture of polymers as a pure feedstock. The process is unique in that it uses readily available, abundant and inexpensive malic acid to form carboalkoxylated valerolactone polymers that can be chemically recycled by two independent pathways. Unlike other traditional bio-based polyesters, recycling monomer synthesis conditions can be tuned to make polymers of varying glass transition points by adjusting carbon chain length and position of functional groups on the monomer variations.


  • Renewable monomer synthesized from malic acid in two steps
  • Chemically recyclable by either of two independent pathways
  • Multiple polymers may be further synthesized allowing for variation of important polymer properties such as glass transition point


  • Tunable recycling stream supporting production of monomers
  • Plastics
  • Elastomers
  • Packaging
  • Adhesives
  • Coatings

Phase of Development - Concept

Interested in Licensing?
The University relies on industry partners to scale up technologies to large enough production capacity for commercial purposes. The license is available for this technology and would be for the sale, manufacture or use of products claimed by the issued patents. Please contact Larry Micek to share your business needs and technical interest in this technology and if you are interested in licensing the technology for further research and development.