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Design of closed-loop recycling production of a Diels–Alder polymer from a biomass-derived difuran as a functional additive for polyurethanes

Journal Article · · Green Chemistry
DOI:https://doi.org/10.1039/d1gc02865k· OSTI ID:1978793
 [1];  [2];  [2];  [3]
  1. Univ. of Wisconsin, Madison, WI (United States); OSTI
  2. Univ. of Wisconsin, Madison, WI (United States)
  3. Univ. of Wisconsin, Madison, WI (United States); Great Lakes Bioenergy Research Center (GLBRC), Madison, WI (United States)
+ Show Author Affiliations

Acetalization of biomass-derived 5-hydroxymethyl furfural (HMF) with pentaerythritol produced a difuran (HPH) monomer in the presence of an acid catalyst. A recyclable polymer was then synthesized by Diels–Alder reaction of bismaleimide and the HMF-derived difuran (HPH). A polyurethane, produced from the Diels–Alder polymer has a higher glass transition temperature than a polyurethane, produced from ethylene glycol. The polyurethane, containing Diels–Alder polymer also has a self-healing ability. The Diels–Alder polymer could be hydrolyzed in acidic acetate buffer at 60 °C to produce the monomers for recycling. Each produced monomer was separated by solvent extraction, and the extracted monomers were recovered in different solvent fractions, such as aqueous, ethyl acetate, and acetone fractions. Techno economic analysis was used to assess the minimum selling price ($$\$$14.1$ per kg) for the primary production of Diels–Alder polymer at a feed capacity of 400 tons per year. The economic viability of the primary recovery process for the most expensive recovered monomer, bismaleimide, was assessed by calculating the minimum selling price of the bismaleimide ($$\$$15.2$ per kg). In conclusion, a circular closed-loop recycling production process for the Diels–Alder polymer was developed and this approach can produce the Diels–Alder polymer at $8.2 per kg when the feed capacity was 40 ktons per year.

Research Organization:
Univ. of Wisconsin, Madison, WI (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division (CSGB); National Institutes of Health (NIH); USDOE Office of Science (SC), Biological and Environmental Research (BER)
Grant/Contract Number:
SC0014058; SC0018409
OSTI ID:
1978793
Alternate ID(s):
OSTI ID: 1822539
Journal Information:
Green Chemistry, Journal Name: Green Chemistry Journal Issue: 23 Vol. 23; ISSN 1463-9262
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

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