Tert-Amyl Alcohol-Mediated Deconstruction of Polyurethane for Polyol and Aniline Recovery

Martin B. Johansen; Bjarke S. Donslund; Steffan K. Kristensen; Anders T. Lindhardt; Troels Skrydstrup

doi:10.1021/acssuschemeng.2c02797

Tert-Amyl Alcohol-Mediated Deconstruction of Polyurethane for Polyol and Aniline Recovery

Martin B. Johansen, Bjarke S. Donslund, Steffan K. Kristensen^*, Anders T. Lindhardt, Troels Skrydstrup^*

^*Corresponding author for this work

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

Abstract

Polyurethane (PU) is a highly engineered and cross-linked polymer found in a plethora of materials such as mattresses, shoes, windmills, and insulation of refrigerating appliances and buildings. Because of PU's inherent stability, chemical recycling is difficult and often affords a secondary feed with different characteristics and properties compared to the original input. In this work, a simple chemical recycling of PU via a solvolysis process using tert-amyl alcohol both as the solvent and reagent is demonstrated. The devised methodology is showcased for the deconstruction of 20 different PU materials with examples of all four cornerstones of PU (rigid solid, rigid foamed, flexible foamed, and flexible solid). The solvolysis affords both polyol and dianiline fractions, constituting monomeric precursors of PU. The methodology is used for the depolymerization of 50 g flexible PU foam affording a polyol within specification of the original virgin polyol (OH value) and an aniline fraction isolated as the precipitated di-HCl salt with a combined mass recovery of 89 wt%. As the solvolysis process provides access to both the polyol and the aniline precursors of the original isocyanate of PU, the procedure presented in this study could pave the way toward a viable circular economy for PU. A further potential utilization of the method is showcased by valorization of a waste stream from split-phase glycolysis, which is another promising method for recovering polyol from flexible PU foam. Finally, preliminary mechanistic investigations are undertaken to probe the intriguing utility of a hindered tertiary alcohol in a solvolysis procedure.

Original language	English
Journal	ACS Sustainable Chemistry and Engineering
Volume	10
Issue	34
Pages (from-to)	11191-11202
Number of pages	12
ISSN	2168-0485
DOIs	https://doi.org/10.1021/acssuschemeng.2c02797
Publication status	Published - Aug 2022

Keywords

base chemicals
chemical recycling
circular plastic economy
end-of-life
polymer deconstruction
polyurethane
solvolysis

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@article{a8e1b3b11275495cb610749206047bfd,

title = "Tert-Amyl Alcohol-Mediated Deconstruction of Polyurethane for Polyol and Aniline Recovery",

abstract = "Polyurethane (PU) is a highly engineered and cross-linked polymer found in a plethora of materials such as mattresses, shoes, windmills, and insulation of refrigerating appliances and buildings. Because of PU's inherent stability, chemical recycling is difficult and often affords a secondary feed with different characteristics and properties compared to the original input. In this work, a simple chemical recycling of PU via a solvolysis process using tert-amyl alcohol both as the solvent and reagent is demonstrated. The devised methodology is showcased for the deconstruction of 20 different PU materials with examples of all four cornerstones of PU (rigid solid, rigid foamed, flexible foamed, and flexible solid). The solvolysis affords both polyol and dianiline fractions, constituting monomeric precursors of PU. The methodology is used for the depolymerization of 50 g flexible PU foam affording a polyol within specification of the original virgin polyol (OH value) and an aniline fraction isolated as the precipitated di-HCl salt with a combined mass recovery of 89 wt%. As the solvolysis process provides access to both the polyol and the aniline precursors of the original isocyanate of PU, the procedure presented in this study could pave the way toward a viable circular economy for PU. A further potential utilization of the method is showcased by valorization of a waste stream from split-phase glycolysis, which is another promising method for recovering polyol from flexible PU foam. Finally, preliminary mechanistic investigations are undertaken to probe the intriguing utility of a hindered tertiary alcohol in a solvolysis procedure.",

keywords = "base chemicals, chemical recycling, circular plastic economy, end-of-life, polymer deconstruction, polyurethane, solvolysis",

author = "Johansen, {Martin B.} and Donslund, {Bjarke S.} and Kristensen, {Steffan K.} and Lindhardt, {Anders T.} and Troels Skrydstrup",

note = "Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",

year = "2022",

month = aug,

doi = "10.1021/acssuschemeng.2c02797",

language = "English",

volume = "10",

pages = "11191--11202",

journal = "ACS Sustainable Chemistry and Engineering",

issn = "2168-0485",

publisher = "American Chemical Society",

number = "34",

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Tert-Amyl Alcohol-Mediated Deconstruction of Polyurethane for Polyol and Aniline Recovery. / Johansen, Martin B.; Donslund, Bjarke S.; Kristensen, Steffan K. et al.
In: ACS Sustainable Chemistry and Engineering, Vol. 10, No. 34, 08.2022, p. 11191-11202.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

TY - JOUR

T1 - Tert-Amyl Alcohol-Mediated Deconstruction of Polyurethane for Polyol and Aniline Recovery

AU - Johansen, Martin B.

AU - Donslund, Bjarke S.

AU - Kristensen, Steffan K.

AU - Lindhardt, Anders T.

AU - Skrydstrup, Troels

PY - 2022/8

Y1 - 2022/8

N2 - Polyurethane (PU) is a highly engineered and cross-linked polymer found in a plethora of materials such as mattresses, shoes, windmills, and insulation of refrigerating appliances and buildings. Because of PU's inherent stability, chemical recycling is difficult and often affords a secondary feed with different characteristics and properties compared to the original input. In this work, a simple chemical recycling of PU via a solvolysis process using tert-amyl alcohol both as the solvent and reagent is demonstrated. The devised methodology is showcased for the deconstruction of 20 different PU materials with examples of all four cornerstones of PU (rigid solid, rigid foamed, flexible foamed, and flexible solid). The solvolysis affords both polyol and dianiline fractions, constituting monomeric precursors of PU. The methodology is used for the depolymerization of 50 g flexible PU foam affording a polyol within specification of the original virgin polyol (OH value) and an aniline fraction isolated as the precipitated di-HCl salt with a combined mass recovery of 89 wt%. As the solvolysis process provides access to both the polyol and the aniline precursors of the original isocyanate of PU, the procedure presented in this study could pave the way toward a viable circular economy for PU. A further potential utilization of the method is showcased by valorization of a waste stream from split-phase glycolysis, which is another promising method for recovering polyol from flexible PU foam. Finally, preliminary mechanistic investigations are undertaken to probe the intriguing utility of a hindered tertiary alcohol in a solvolysis procedure.

AB - Polyurethane (PU) is a highly engineered and cross-linked polymer found in a plethora of materials such as mattresses, shoes, windmills, and insulation of refrigerating appliances and buildings. Because of PU's inherent stability, chemical recycling is difficult and often affords a secondary feed with different characteristics and properties compared to the original input. In this work, a simple chemical recycling of PU via a solvolysis process using tert-amyl alcohol both as the solvent and reagent is demonstrated. The devised methodology is showcased for the deconstruction of 20 different PU materials with examples of all four cornerstones of PU (rigid solid, rigid foamed, flexible foamed, and flexible solid). The solvolysis affords both polyol and dianiline fractions, constituting monomeric precursors of PU. The methodology is used for the depolymerization of 50 g flexible PU foam affording a polyol within specification of the original virgin polyol (OH value) and an aniline fraction isolated as the precipitated di-HCl salt with a combined mass recovery of 89 wt%. As the solvolysis process provides access to both the polyol and the aniline precursors of the original isocyanate of PU, the procedure presented in this study could pave the way toward a viable circular economy for PU. A further potential utilization of the method is showcased by valorization of a waste stream from split-phase glycolysis, which is another promising method for recovering polyol from flexible PU foam. Finally, preliminary mechanistic investigations are undertaken to probe the intriguing utility of a hindered tertiary alcohol in a solvolysis procedure.

KW - base chemicals

KW - chemical recycling

KW - circular plastic economy

KW - end-of-life

KW - polymer deconstruction

KW - polyurethane

KW - solvolysis

UR - http://www.scopus.com/inward/record.url?scp=85136704289&partnerID=8YFLogxK

U2 - 10.1021/acssuschemeng.2c02797

DO - 10.1021/acssuschemeng.2c02797

M3 - Journal article

AN - SCOPUS:85136704289

SN - 2168-0485

VL - 10

SP - 11191

EP - 11202

JO - ACS Sustainable Chemistry and Engineering

JF - ACS Sustainable Chemistry and Engineering

IS - 34

ER -

Tert-Amyl Alcohol-Mediated Deconstruction of Polyurethane for Polyol and Aniline Recovery

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