Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

Bioenabled Platform to Access Polyamides with Built-In Target Properties

Journal Article · · Journal of the American Chemical Society
DOI:https://doi.org/10.1021/jacs.2c01397· OSTI ID:1978472

The diversification of platform chemicals is key to today’s petroleum industry. Likewise, the flourishing of tomorrow’s biorefineries will rely on molecules with next-generation properties from biomass. Herein, we explore this opportunity with a novel approach to monomers with custom property enhancements. Cyclic diacids with alkyl and aromatic decorations were synthesized from muconic acid by Diels-Alder cycloaddition and copolymerized with hexamethylenediamine and adipic acid to yield polyamides with built-in hydrophobicity and flame retardancy. Testing shows a 70% reduction in water uptake and doubling of char production while largely retaining other key properties of the parent Nylon-6,6. In conclusion, the present approach can be generalized to access a wide range of performance-advantaged polyamides.

Research Organization:
Iowa State University, Ames, IA (United States)
Sponsoring Organization:
USDOE Office of Energy Efficiency and Renewable Energy (EERE), Office of Sustainable Transportation. Bioenergy Technologies Office (BETO)
Grant/Contract Number:
EE0008492
OSTI ID:
1978472
Journal Information:
Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 22 Vol. 144; ISSN 0002-7863
Publisher:
American Chemical Society (ACS)Copyright Statement
Country of Publication:
United States
Language:
English

References (33)

Biodegradable and Bio-Based Polymers: Future Prospects of Eco-Friendly Plastics journal January 2015
Production of Diethyl Terephthalate from Biomass-Derived Muconic Acid journal November 2015
Combining Metabolic Engineering and Electrocatalysis: Application to the Production of Polyamides from Sugar journal January 2016
Molecular Firefighting—How Modern Phosphorus Chemistry Can Help Solve the Challenge of Flame Retardancy journal August 2018
H 2 ‐Free Re‐Based Catalytic Dehydroxylation of Aldaric Acid to Muconic and Adipic Acid Esters journal November 2020
Efficient Catalysts for the Green Synthesis of Adipic Acid from Biomass journal January 2021
Biorenewable blends of polyamide‐4,10 and polyamide‐6,10 journal April 2016
Bio Adipic Acid Production from Sodium Muconate and Muconic Acid: A Comparison of two Systems journal June 2019
A Robust Strategy for Sustainable Organic Chemicals Utilizing Bioprivileged Molecules journal April 2019
Sustainable, Stereoregular, and Optically Active Polyamides via Cationic Polymerization of ε-Lactams Derived from the Terpene β-Pinene journal March 2017
Some basic aspects of flame resistance of polymeric materials journal August 1975
Glass transition temperature in nylons journal December 1976
Flame retardancy mechanisms of aluminium phosphinate in combination with melamine polyphosphate and zinc borate in glass-fibre reinforced polyamide 6,6 journal August 2007
Analysis of the Amorphous and Interphase Influence of Comononomer Loading on Polymer Properties toward Forwarding Bioadvantaged Copolyamides journal August 2021
Electrochemical Conversion of Muconic Acid to Biobased Diacid Monomers journal May 2016
Computational Framework for the Identification of Bioprivileged Molecules journal December 2018
Step-growth polymerization journal November 1981
Biobased chiral semi-crystalline or amorphous high-performance polyamides and their scalable stereoselective synthesis journal January 2020
The battle for the “green” polymer. Different approaches for biopolymer synthesis: bioadvantaged vs. bioreplacement journal January 2014
Adipic acid production from lignin journal January 2015
Catalytic routes towards acrylic acid, adipic acid and ε-caprolactam starting from biorenewables journal January 2015
cis,cis-Muconic acid: separation and catalysis to bio-adipic acid for nylon-6,6 polymerization journal January 2016
Sustainable terpene-based polyamides via anionic polymerization of a pinene-derived lactam journal January 2018
Bioprivileged molecules: creating value from biomass journal January 2017
Biomass-derived monomers for performance-differentiated fiber reinforced polymer composites journal January 2017
cis,cis-Muconic acid isomerization and catalytic conversion to biobased cyclic-C 6 -1,4-diacid monomers journal January 2017
Heterogeneous Diels–Alder catalysis for biomass-derived aromatic compounds journal January 2017
Muconic acid isomers as platform chemicals and monomers in the biobased economy journal January 2020
Trends in the Diels–Alder reaction in polymer chemistry journal January 2021
Solvent-driven isomerization of cis,cis-muconic acid for the production of specialty and performance-advantaged cyclic biobased monomers journal January 2020
Electrochemical hydrogenation of bioprivilegedcis,cis-muconic acid totrans-3-hexenedioic acid: from lab synthesis to bench-scale production and beyond journal January 2021
Biobased Terephthalic Acid Technologies: A Literature Review journal April 2014
Novel Random Copolymers of Poly(butylene 1,4-cyclohexane dicarboxylate) with Outstanding Barrier Properties for Green and Sustainable Packaging: Content and Length of Aliphatic Side Chains as Efficient Tools to Tailor the Material’s Final Performance journal August 2018