Catalytic Decomposition of Long‐Chain Olefins to Propylene via Isomerization‐Metathesis Using Latent Bicyclic (Alkyl)(Amino)Carbene‐Ruthenium Olefin Metathesis Catalysts
Open accessAbstract
One of the most exciting scientific challenges today is the catalytic degradation of non‐biodegradable polymers into value‐added chemical feedstocks. The mild pyrolysis of polyolefins, including high‐density polyethylene (HDPE), results in pyrolysis oils containing long‐chain olefins as major products. In this paper, novel bicyclic (alkyl)(amino)carbene ruthenium (BICAAC−Ru) temperature‐activated latent olefin metathesis catalysts, which can be used for catalytic decomposition of long‐chain olefins to propylene are reported. These thermally stable catalysts show significantly higher selectivity to propylene at a reaction temperature of 75 °C compared to second generation Hoveyda–Grubbs or CAAC−Ru catalysts under ethenolysis conditions. The conversion of long‐chain olefins (e.g., 1‐octadecene or methyl oleate) to propylene via isomerization‐metathesis is performed by using a (RuHCl)(CO)(PPh 3 ) 3 isomerization co‐catalyst. The reactions can be carried out at a BICAAC−Ru catalyst loading as low as 1 ppm at elevated reaction temperature (75 °C). The observed turnover number and turnover frequency are as high as 55 000 and 10 000 mol propylene mol catalyst −1 h −1 , respectively.
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- Authors
- Nagyházi, M., Lukács, Á., Turczel, G., Hancsók, J., Valyon, J., Bényei, A., Kéki, S., & Tuba, R.
- Affiliations
- Budapest University of Technology and Economics (HU)
- Institute of Materials and Environmental Chemistry (HU)
- University of Pannonia (HU)
- University of Debrecen (HU)
- Corresponding author
- Tuba, Róbert
- ORCID
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2022-05-19
- Volume
- 61
- Issue
- 28
- Pages
- e202204413-e202204413
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- PMC
- PMC9400880
- OpenAlex
- W4223945494
- Cited by
- 54
- References
- 48
- Citations by year
- 2026: 4 · 2025: 21 · 2024: 14 · 2023: 8 · 2022: 7
- FWCI
- 4.76
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- Angewandte Chemie International Edition (publishedVersion, cc-by)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- Repository of the Academy's Library (Library of the Hungarian Academy of Sciences) (acceptedVersion)
- University of Debrecen Electronic Archive (University of Debrecen) (submittedVersion, cc-by)
- Funders
- Nemzeti Kutatási Fejlesztési és Innovációs Hivatal (NKFI NN-128368, TKP-108-9/PALY-2021)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Synthetic Organic Chemistry Methods
- Physical Sciences › Chemistry › Organic Chemistry › Organometallic Complex Synthesis and Catalysis
- Physical Sciences › Chemical Engineering › Process Chemistry and Technology › Carbon dioxide utilization in catalysis
- Keywords
- long-chain olefins, propylene production, olefin metathesis, latent catalysts, ruthenium olefin metathesis catalysts, bio-oil, high-density polyethylene, ethenolysis, methyl oleate, 1-octadecene, catalyst loading
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