Office for Technology Commercialization
http://www.research.umn.edu/techcomm
612-624-0550

Process to Manufacture Branched Caprolactone

Technology #2019-011

Questions about this technology? Ask a Technology Manager

Download Printable PDF

Image Gallery
Process chemistries for the conversion of p-cresol to 4-methyl-ε-caprolactoneOxidation Reactor, R-2, Economic PerformanceHydrogenation (B-1, R-1 & F-1), ketone purification (C-1 & C-2), ketone oxidation (R-2, D-1 & C-4), and caprolactone purification (C-3 & C-5)
Categories
Researchers
Paul Dauenhauer, PhD
Associate Professor, Chemical Engineering Materials Science
External Link (www.cems.umn.edu)
Marc Hillmyer, PhD
Professor, Department of Chemistry
External Link (chem.umn.edu)
Managed By
Larry Micek
Technology Licensing Officer 612-624-9568
Patent Protection

Provisional Patent Application Filed
Publications
Techno-Economic Analysis of a Chemical Process to Manufacture Methyl-ε-Caprolactone from Cresols
ACS Sustainable Chem. Eng., Publication Date (Web): September 28, 2018

Two-stage process manufactures methyl-ε-caprolactone (MCL)

A cost effective, new two-stage chemical process manufactures methyl-ε-caprolactone (MCL) from cresol, a fossil or bio-renewable feedstock. Details for designing a process optimized for net present value (including unit operation design of two reactors, distillation and integrated heat transfer) were determined via process simulation. The two-reaction process first hydrogenates cresol to methyl-cyclohexanone, which is then followed by Baeyer-Villiger oxidation to MCL. Improvements in overall selectivity via catalytic performance of the Baeyer-Villiger oxidation catalyst boost the overall economics of the process, rendering it a low-cost process broadly applicable to multiple classes of alkyl-phenol feedstocks. The novel process can manufacture MCL for use in polymer/plastics.

Combines all reaction, separation and purification operations

Polymers related to poly-ε-caprolactone (PCL), which have many biomedical and industrial field applications, could be derived from biobased starting materials, but the challenge has been finding a cost effective route to the starting monomer. This new process uses already-existing chemistry in a brand new way, putting all reaction, separation and purification operations together in a cost-competitive manner. The result is a high yield and inexpensive method of producing 4-methyl-ε-caprolactone (and other alkyl caprolactones) from lignin or petroleum-based starting materials.

Phase of Development

  • Proof of concept. Simulation models with technical description of chemical process conditions and unit connectivity with economic analysis.

Benefits

  • Low-cost process; potential for extremely lucrative chemical product
  • High process yield potential
  • Broadly applicable to multiple classes of alkyl-phenol feedstocks
  • Aspen model based technoeconomic analysis available

Features

  • Manufactures methyl-ε-caprolactone (MCL) (and other alkyl caprolactones) from biobased cresol, lignin or petroleum based starting materials
  • Two-stage chemical process
  • Baeyer-Villiger oxidation catalyst improves overall selectivity
  • Combines all reaction, separation and purification operations together

Applications

  • Chemicals/polymers
  • Caprolactone
  • Monomers
  • Methyl-e-caprolactone (MCL) manufacture


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.