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Title: Aliphatic amines from waste polyolefins by tandem pyrolysis, hydroformylation, and reductive amination

Journal Article · · Green Chemistry
DOI: https://doi.org/10.1039/d4gc01013b · OSTI ID:2345934
ORCiD logo [1]; ORCiD logo [2];  [3]; ORCiD logo [4];  [4];  [3]; ORCiD logo [4];  [4]; ORCiD logo [4];  [3]; ORCiD logo [2]; ORCiD logo [3]
  1. Univ. of Wisconsin, Madison, WI (United States); University of Wisconsin-Madison Department of Chemical and Biological Engineering
  2. National Renewable Energy Laboratory (NREL), Golden, CO (United States). Renewable Resources and Enabling Sciences Center
  3. Univ. of Wisconsin, Madison, WI (United States)
  4. Iowa State Univ., Ames, IA (United States)
+ Show Author Affiliations

Pyrolysis of waste plastics can produce a product mixture with a high concentration of olefins (>50 wt%). The olefins, as building blocks in the petroleum industry, are potential precursors for valuable commodity chemicals with higher values (>$2000 per ton). In this work, we produce aldehydes by hydroformylation of the olefins present in pyrolysis oil from colored post-consumer recycled high-density polyethylene (PCR-HDPE). The obtained aldehydes in the oil are then converted into aliphatic amines via reductive amination with a Ru/C catalyst. The aminated oil was characterized by multiple analytical chemistry techniques including elemental analysis, nuclear magnetic resonance spectroscopy, high-resolution liquid chromatography-mass spectrometry, and gas chromatography-mass spectrometry with a Polyarc flame ionization detector. The concentration of metals in the PCR-HDPE and oil changes during the tandem processes, showing limited effects of these elements (e.g., Al, Ca, Fe, Mg, Ti, Zn) on hydroformylation and reductive amination. Additionally, we demonstrated that reductive amination of aldehydes with varied carbon numbers and branching properties can be achieved in the presence of a complex mixture, including paraffins and aromatics. Finally, the results indicate that waste plastics have the potential to serve as a renewable source for mono and di aliphatic amines, thereby diminishing reliance on fossil feedstocks as the current primary amine source.

Research Organization:
Univ. of Wisconsin, Madison, WI (United States); Alliance for Sustainable Energy, LLC (United States)
Sponsoring Organization:
USDOE Office of Energy Efficiency and Renewable Energy (EERE), Office of Sustainable Transportation. Bioenergy Technologies Office (BETO)
Grant/Contract Number:
EE0009285; AC36-08GO28308
OSTI ID:
2345934
Alternate ID(s):
OSTI ID: 2341352; OSTI ID: 2349287
Journal Information:
Green Chemistry, Journal Name: Green Chemistry Journal Issue: 15 Vol. 26; ISSN 1463-9262
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
waste plastics
upcycling
hydroformylation
reductive amination
aliphatic amines
catalysis