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Ring-opening metathesis polymerization

Type of chain-growth polymerisation reaction involving cyclic olefins

Summary

Type of chain-growth polymerisation reaction involving cyclic olefins

In polymer chemistry, ring-opening metathesis polymerization (ROMP) is a type of chain-growth polymerization involving olefin metathesis. The reaction is driven by relieving ring strain in cyclic olefins. A variety of heterogeneous and homogeneous catalysts have been developed for different polymers and mechanisms. Heterogeneous catalysts are typical in large-scale commercial processes, while homogeneous catalysts are used in finer laboratory chemical syntheses. Organometallic catalysts used in ROMP usually have transition metal centres, such as tungsten, ruthenium, titanium, etc., with organic ligands.

Heterogeneous catalysis

:[[File:Polynbornene.svg|thumb|center|404px|ROMP reaction giving [[polynorbornene]]. Like most commercial alkene metathesis processes, this reaction does not employ a well-defined molecular catalyst.]] Heterogeneous catalysis consists of catalysts and substrates in different physical states. The catalyst is typically in solid phase. The mechanism of heterogeneous ring-opening metathesis polymerization is still under investigation.

Ring-opening metathesis polymerization of cyclic olefins has been commercialized since the 1970s. Examples of polymers produced on an industrial level through ROMP catalysis are Vestenamer, Norsorex and ZEONEX, among others.

Mechanism

The mechanism of homogeneous ring-opening metathesis polymerization is well-studied. It is similar to any olefin metathesis reaction. Initiation occurs by forming an open coordination site on the catalyst. Propagation happens via a metallacycle intermediate formed after a 2+2 cycloaddition. When using a G3 catalyst, 2+2 cycloaddition is the rate determining step.

Frontal ring-opening metathesis polymerization

Frontal ring-opening metathesis polymerization (FROMP) is a variation of ROMP. It is a polymerization system that reacts via a cascading reaction front after application of a trigger to kick off the reaction in a localized zone. One example of this system is the FROMP of dicyclopentadiene with a Grubbs' catalyst initiated by heat.

References

References

  1. Buchmeiser, Michael R.. (2009-01-28). "Ring-Opening Metathesis Polymerization". Wiley.
  2. (2009-01-28). "Thermodynamics and Kinetics of Ring-Opening Polymerization". Wiley.
  3. (2009-09-23). "Functional end groups for polymers prepared using ring-opening metathesis polymerization". Nature Chemistry.
  4. (2001-01-26). "Kirk-Othmer Encyclopedia of Chemical Technology". Wiley.
  5. (2008). "Polymers: chemistry and physics of modern materials". CRC Press.
  6. (March 2019). "Well-Defined Alkyne Metathesis Catalysts: Developments and Recent Applications". Chemistry – A European Journal.
  7. (2024-04-19). "PhotoROMP: The Future Is Bright". ACS Catalysis.
  8. Mol, J. C.. (2004-04-13). "Industrial applications of olefin metathesis". Journal of Molecular Catalysis A: Chemical.
  9. Hyatt, Michael G.. (2019-11-06). "Mechanistic and Kinetic Studies of the Ring Opening Metathesis Polymerization of Norbornenyl Monomers by a Grubbs Third Generation Catalyst". Journal of the American Chemical Society.
  10. Pojman, J.A.. (2012). "Frontal Polymerization". Elsevier.
  11. (2017-04-13). "Grubbs-inspired metathesis in the Moore group". Journal of Polymer Science Part A: Polymer Chemistry.
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This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

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