Catalytic deconstruction of waste polyethylene with ethylene to form propylene
Open accessAbstract
The conversion of polyolefins to monomers would create a valuable carbon feedstock from the largest fraction of waste plastic. However, breakdown of the main chains in these polymers requires the cleavage of carbon–carbon bonds that tend to resist selective chemical transformations. Here, we report the production of propylene by partial dehydrogenation of polyethylene and tandem isomerizing ethenolysis of the desaturated chain. Dehydrogenation of high-density polyethylene with either an iridium-pincer complex or platinum/zinc supported on silica as catalysts yielded dehydrogenated material containing up to 3.2% internal olefins; the combination of a second-generation Hoveyda-Grubbs metathesis catalyst and [PdP( t Bu) 3 (μ-Br)] 2 as an isomerization catalyst selectively degraded this unsaturated polymer to propylene in yields exceeding 80%. These results show promise for the application of mild catalysis to deconstruct otherwise stable polyolefins.
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Degradation of P7 in the presence of ethylene and stoichiometric HG II yielded telechelic macromonomers capped with vinyl ends.
“Thus, the degradation ability of P7 was examined in the presence of E and stoichiometric HG II following previously reported procedure.24 Telechelic macromonomers capped with vinyl ends were harvested (Table S3, entry 1; Figure S1).18”
From Installing a Trigger to Upcycle High-Density Polyethylene (2024) · cites this paper as [24]
The ethenolysis passage (indexed section labeled Abstract; page unavailable) reports cleavage of unsaturated HDPE using ethylene and a second-generation Hoveyda–Grubbs catalyst, supporting the cited procedure. It does not report an experiment on P7 or the harvesting of vinyl-capped telechelic macromonomers, and it specifies 3.6 mol % catalyst rather than a stoichiometric amount. In the citing sentence, the product claim is attached to a different citation. (LLM, conf=0.85)
Experimental — accuracy not yet measuredThe structure of P7 is consistent with the most advantageous structure for a recyclable polyethylene.
“For copolymer P7, with E content increasing up to 97.6%, BD inserts in the discrete 1,4-regularity in major (1,4:1,2 = 1.9:0.5%), and CC units disappear completely (similar to P8, Table 1, entries 7 and 8), which is consistent with the most advantageous structure for a recyclable PE.24”
From Installing a Trigger to Upcycle High-Density Polyethylene (2024) · cites this paper as [24]
The paper’s discussion of PE degradation (section labeled Abstract; page unavailable) reports that internal olefins enable conversion to propylene, while high unsaturation and branching reduce yields. That supports the general rationale for a lightly unsaturated, predominantly linear PE structure, but the paper does not evaluate P7 or establish its specific 1,4-butadiene content and absence of CC units as the most advantageous structure for recyclability. (LLM, conf=0.84)
Experimental — accuracy not yet measuredFor P7, with E content up to 97.6%, butadiene inserts in discrete 1,4-regularity in major proportion (1,4:1,2 = 1.9:0.5%), and CC units disappear completely.
“For copolymer P7, with E content increasing up to 97.6%, BD inserts in the discrete 1,4-regularity in major (1,4:1,2 = 1.9:0.5%), and CC units disappear completely (similar to P8, Table 1, entries 7 and 8), which is consistent with the most advantageous structure for a recyclable PE.24”
From Installing a Trigger to Upcycle High-Density Polyethylene (2024) · cites this paper as [24]
The paper reports that less-branched HDPE gave higher propylene yields than LDPE and that highly unsaturated polymers gave lower yields (passages [8] and [2], section labeled Abstract; page unavailable). This supports the general relevance of polymer structure to chemical recycling, but it does not establish that P7’s particular butadiene arrangement is the most advantageous structure, nor does it report P7’s composition or CC-unit result. (LLM, conf=0.83)
Experimental — accuracy not yet measuredValorization of plastics yields new chemicals rather than original monomer feedstocks.
“Valorization of plastics is an alternative approach to recapture resources but yields new chemicals rather than original monomer feedstocks”
From Chemically recyclable polyolefin-like multiblock polymers (2023) · cites this paper as [7]
The Abstract reports converting polyethylene to propylene, a different chemical from polyethylene’s original ethylene feedstock. That supports this example of valorization, but the claim generalizes the outcome to plastics as a whole; the paper also describes processes that regenerate monomers for repolymerization. (LLM, conf=0.83)
Experimental — accuracy not yet measuredIsomerizing ethenolysis of Aging-P7 gave propylene in a yield of 70.3%, comparable to the result obtained using dehydrogenated PE.
“First, isomerizing ethenolysis (I/E) was conducted to give propylene in a yield of 70.3% (Figures 4A and S16), comparable to the result obtained using the dehydrogenated PE.24”
From Installing a Trigger to Upcycle High-Density Polyethylene (2024) · cites this paper as [24]
In polyethylene, C=C bonds in the main chain act as weak sites that can initiate controllable cleavage via oxidation and metathesis reactions, enabling upcycling into liquid fuels, value-added precursors, or propylene monomer.
“Creating unsaturated C=C bonds into PE main chains to break the homogeneous stable C–C bonds, which are “weak” sites to initiate controllable cleavage via oxidation and metathesis reactions to realize upcycling PE into liquid fuels17,18 or value-added precursors19−23 and even propylene monomer24−26 provides a sustainable development route for PE (Scheme 1b).”
From Installing a Trigger to Upcycle High-Density Polyethylene (2024) · cites this paper as [24]
Both TET and V sequences are undesired structures for recyclable polyethylene.
“Both the TET and V sequences are undesired structures for recyclable PE.24”
From Installing a Trigger to Upcycle High-Density Polyethylene (2024) · cites this paper as [24]
The Abstract discusses difficulties recycling mixed polyethylene and reports that branching and unsaturation can reduce propylene yields during catalytic deconstruction. Searches for “TET sequence” and “V sequence” found no passage identifying those sequences or saying both are undesirable in recyclable PE; the cited copy does not address the specific claim. (LLM, conf=0.77)
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- Authors
- Conk, R. J., Hanna, S., Shi, J. X., Yang, J., Ciccia, N. R., Qi, L., Bloomer, B. J., Heuvel, S., Wills, T., Su, J., Bell, A. T., & Hartwig, J. F.
- Affiliations
- Lawrence Berkeley National Laboratory (US)
- University of California, Berkeley (US)
- Corresponding author
- Conk, Richard J.
- Hanna, Steven
- Hartwig, John F.
- ORCID
- Venue
- Science
- Published
- 2022-09-30
- Volume
- 377
- Issue
- 6614
- Pages
- 1561-1566
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- PMC
- PMC11723507
- OpenAlex
- W4298006419
- Cited by
- 420
- References
- 36
- Citations by year
- 2026: 80 · 2025: 149 · 2024: 112 · 2023: 71 · 2022: 8
- FWCI
- 32.35
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- Science (publishedVersion)
- PubMed (publishedVersion)
- PubMed Central (acceptedVersion)
- eScholarship (California Digital Library) (submittedVersion)
- Funders
- National Science Foundation (DEAC02-05CH11231)
- U.S. Department of Energy (-AC02-05CH11231, 05CH11231, DE AC02 05CH11231, DE-AC02-)
- National Institutes of Health (1s10od024998-01, DE-AC02–05CH11231)
- Office of Science (DEAC02–05CH11231, AC02-05CH11231, DE-AC02, 05CH11231)
- Basic Energy Sciences (DE-AC02, 05CH11231, DE-AC02-05CH11231., AC02–05CH11231)
- Lawrence Berkeley National Laboratory (AC02‐05CH11231, DE-AC02-05CH11231, 05CH11231)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Organometallic Complex Synthesis and Catalysis
- Physical Sciences › Chemical Engineering › Catalysis › Catalysis and Oxidation Reactions
- Physical Sciences › Materials Science › Polymers and Plastics › Polymer crystallization and properties
- Keywords
- propylene production, waste plastic recycling, ethenolysis, tandem catalysis, iridium pincer complexes, internal olefins, carbon feedstock
- MeSH terms
- Alkenes, Carbon, Catalysis, Ethylenes, Iridium, Platinum, Polyenes, Silicon Dioxide, Waste Management, Polyethylene
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