Upcycling of Waste Plastics into Carboxylic Acids for Biodegradable Surfactants

Li, Houqian; Tipton, Brandon W.; Aboukeila, Hesham; Mendoza, Enner A.; Alzailaie, Abdulrahman; Yan, Tianwei; Landis, Clark R.; Weston, Javen S.; Grady, Brian P.; Huber, George W.

doi:10.1002/anie.202517471

Title: Upcycling of Waste Plastics into Carboxylic Acids for Biodegradable Surfactants

Journal Article · Fri Oct 17 00:00:00 UTC 2025 · Angewandte Chemie (International Edition)

DOI: https://doi.org/10.1002/anie.202517471 · OSTI ID:3374882

^[1]; Tipton, Brandon W. ^[1];

^[2];

^[1]; Alzailaie, Abdulrahman ^[1]; Yan, Tianwei ^[1]; Landis, Clark R. ^[1]; Weston, Javen S. ^[3]; Grady, Brian P. ^[2];

^[1]

University of Wisconsin-Madison, WI (United States)
University of Oklahoma, Norman, OK (United States)
University of Tulsa, OK (United States)

This work outlines a process for producing high‐purity (>95%) carboxylate surfactants from post‐consumer recycled high‐density polyethylene (PCR‐HDPE). The approach involves the thermal depolymerization of PCR‐HDPE via pyrolysis, followed by fractional distillation to isolate C9–C14 olefins. These olefins undergo hydroformylation using cobalt carbonyl catalysts to generate aldehydes, which are subsequently oxidized to carboxylic acids using Pinnick oxidation under mild aqueous‐phase conditions. Neutralization of the resulting carboxylic acids with sodium hydroxide produces plastic‐derived carboxylate surfactants (PDCs) in the form of sodium carboxylates. Subsequent purification steps ensure surfactant‐grade purity and enable accurate assessment of physicochemical properties. The resulting PDCs are evaluated for critical micelle concentration (CMC), foamability, surface tension reduction, and calcium ion tolerance, demonstrating competitive behavior with conventional anionic carboxylate surfactants. This route provides a sustainable alternative for surfactant production, reducing reliance on fossil‐derived feedstocks and valorizing plastic waste streams through chemical upcycling.

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Research Organization:: University of Oklahoma, Norman, OK (United States); University of Tulsa, OK (United States); University of Wisconsin-Madison, WI (United States)

Sponsoring Organization:: National Science Foundation (NSF); USDOE Office of Energy Efficiency and Renewable Energy (EERE), Office of Sustainable Transportation. Bioenergy Technologies Office (BETO)

Grant/Contract Number:: EE0009285

OSTI ID:: 3374882

Journal Information:: Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Journal Issue: 50 Vol. 64; ISSN 1521-3773; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

References (31)

Catalytic Oxidation of Organic Substrates by Molecular Oxygen and Hydrogen Peroxide by Multistep Electron Transfer—A Biomimetic Approach Piera, Julio; Bäckvall, Jan-E. Angewandte Chemie International Edition, Vol. 47, Issue 19 https://doi.org/10.1002/anie.200700604	journal	April 2008
Surfactant mixtures: A short review Grady, Brian P. Journal of Surfactants and Detergents, Vol. 26, Issue 3 https://doi.org/10.1002/jsde.12642	journal	November 2022
Effect of Protonation on the Solution and Phase Behavior of Aqueous Sodium Myristate Wen, Xinyun; Franses, Elias I. Journal of Colloid and Interface Science, Vol. 231, Issue 1 https://doi.org/10.1006/jcis.2000.7156	journal	November 2000
A comparison of the ethoxylation of a fatty alcohol, fatty acid, and dimethiconol O’Lenick, Anthony J.; Parkinson, Jeffrey K. Journal of the American Oil Chemists' Society, Vol. 73, Issue 1 https://doi.org/10.1007/BF02523449	journal	January 1996
Fractional distillation of biocrude from hydrothermal liquefaction of microalgae: Upgrading of fuel properties Liu, Tonggui; Yang, Longsheng; Jiao, Huiting Algal Research, Vol. 68 https://doi.org/10.1016/j.algal.2022.102888	journal	November 2022
Catalytic behaviour of nickel and iron metal contaminants of an FCC catalyst after oxidative and reductive thermal treatments Tangstad, E.; Andersen, A.; Myhrvold, E. M. Applied Catalysis A: General, Vol. 346, Issue 1-2 https://doi.org/10.1016/j.apcata.2008.05.022	journal	August 2008
Structural features and surfactant properties of core–shell type micellar aggregates formed by gemini piperidinium surfactants Bhadani, Avinash; Okano, Tomoaki; Ogura, Taku Colloids and Surfaces A: Physicochemical and Engineering Aspects, Vol. 494 https://doi.org/10.1016/j.colsurfa.2015.11.073	journal	April 2016
Synthesis, chemistry, physicochemical properties and industrial applications of amino acid surfactants: A review Tripathy, Divya B.; Mishra, Anuradha; Clark, James Comptes Rendus. Chimie, Vol. 21, Issue 2 https://doi.org/10.1016/j.crci.2017.11.005	journal	February 2018
Pyrolysis–gasification of plastics, mixed plastics and real-world plastic waste with and without Ni–Mg–Al catalyst Wu, Chunfei; Williams, Paul T. Fuel, Vol. 89, Issue 10 https://doi.org/10.1016/j.fuel.2010.05.032	journal	October 2010
Vacuum fractional distillation of biocrude oil and the immobilization of harmful metal Li, Hugang; Tian, Chunyan; Lu, Jianwen Fuel, Vol. 326 https://doi.org/10.1016/j.fuel.2022.125013	journal	October 2022
Carboxymethylation of polysaccharides: Synthesis and bioactivities Chakka, Vara Prasad; Zhou, Tao International Journal of Biological Macromolecules, Vol. 165 https://doi.org/10.1016/j.ijbiomac.2020.10.178	journal	December 2020
Estimation of diffusion coefficients by using a linear correlation between the diffusion coefficient and molecular weight Valencia, Drochss P.; González, Felipe J. Journal of Electroanalytical Chemistry, Vol. 681 https://doi.org/10.1016/j.jelechem.2012.06.013	journal	August 2012
Opportunities and challenges for the application of post-consumer plastic waste pyrolysis oils as steam cracker feedstocks: To decontaminate or not to decontaminate? Kusenberg, Marvin; Eschenbacher, Andreas; Djokic, Marko R. Waste Management, Vol. 138 https://doi.org/10.1016/j.wasman.2021.11.009	journal	February 2022
Carbon nanotubes production from real-world waste plastics and the pyrolysis behaviour Zhu, Yuan; Miao, Jie; Zhang, Yingrui Waste Management, Vol. 166 https://doi.org/10.1016/j.wasman.2023.05.002	journal	July 2023
Condensation Oligomers with Sequence Control but without Coupling Reagents and Protecting Groups via Asymmetric Hydroformylation and Hydroacyloxylation Foarta, Floriana; Landis, Clark R. The Journal of Organic Chemistry, Vol. 81, Issue 22 https://doi.org/10.1021/acs.joc.6b02210	journal	November 2016
Pinnick Oxidation on Scale: Process Development of a BDK Inhibitor Arcari, Joel T.; Buckley, Catherine; Buzon, Leanne M. Organic Process Research & Development, Vol. 28, Issue 7 https://doi.org/10.1021/acs.oprd.4c00177	journal	July 2024
Experimental Investigation of Foam Flooding Using Anionic and Nonionic Surfactants: A Screening Scenario to Assess the Effects of Salinity and pH on Foam Stability and Foam Height Emami, Hassan; Ayatizadeh Tanha, Abbas; Khaksar Manshad, Abbas ACS Omega, Vol. 7, Issue 17 https://doi.org/10.1021/acsomega.2c00314	journal	April 2022
Green and Efficient: Oxidation of Aldehydes to Carboxylic Acids and Acid Anhydrides with Air Liu, Kai-Jian; Fu, Yu-Ling; Xie, Long-Yong ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 4 https://doi.org/10.1021/acssuschemeng.7b04400	journal	March 2018
Tandem Hydroformylation/Hydrogenation of Alkenes to Normal Alcohols Using Rh/Ru Dual Catalyst or Ru Single Component Catalyst Takahashi, Kohei; Yamashita, Makoto; Nozaki, Kyoko Journal of the American Chemical Society, Vol. 134, Issue 45 https://doi.org/10.1021/ja307998h	journal	November 2012
Size and Shape of Detergent Micelles Determined by Small-Angle X-ray Scattering Lipfert, Jan; Columbus, Linda; Chu, Vincent B. The Journal of Physical Chemistry B, Vol. 111, Issue 43 https://doi.org/10.1021/jp073016l	journal	November 2007
Effect of Hydrophobic Chain Length of Surfactants on Enthalpy−Entropy Compensation of Micellization Chen, Li-Jen; Lin, Shi-Yow; Huang, Chiung-Chang The Journal of Physical Chemistry B, Vol. 102, Issue 22 https://doi.org/10.1021/jp9804345	journal	May 1998
Correcting for a Density Distribution: Particle Size Analysis of Core–Shell Nanocomposite Particles Using Disk Centrifuge Photosedimentometry Fielding, Lee A.; Mykhaylyk, Oleksandr O.; Armes, Steven P. Langmuir, Vol. 28, Issue 5 https://doi.org/10.1021/la204841n	journal	January 2012
Development of a Greener Hydroformylation Process Guided by Quantitative Sustainability Assessments Xie, Zhuanzhuan; Subramaniam, Bala ACS Sustainable Chemistry & Engineering, Vol. 2, Issue 12 https://doi.org/10.1021/sc500483f	journal	November 2014
Expanding plastics recycling technologies: chemical aspects, technology status and challenges Li, Houqian; Aguirre-Villegas, Horacio A.; Allen, Robert D. Green Chemistry, Vol. 24, Issue 23 https://doi.org/10.1039/D2GC02588D	journal	January 2022
Aliphatic amines from waste polyolefins by tandem pyrolysis, hydroformylation, and reductive amination Li, Houqian; Cuthbertson, Amy A.; Alamer, Ahmad Amer Green Chemistry, Vol. 26, Issue 15 https://doi.org/10.1039/D4GC01013B	journal	January 2024
The Effects of Polyolefin Structure and Source on Pyrolysis-Derived Plastic Oil Composition Wu, Jiayang; Jiang, Zhen; Cecon, Victor S. Green Chemistry https://doi.org/10.1039/D4GC04029E	journal	January 2024
Sodium borohydride in carboxylic acid media: a phenomenal reduction system W. Gribble, Gordon Chemical Society Reviews, Vol. 27, Issue 6 https://doi.org/10.1039/a827395z	journal	January 1998
Hydroformylation of pyrolysis oils to aldehydes and alcohols from polyolefin waste Li, Houqian; Wu, Jiayang; Jiang, Zhen Science, Vol. 381, Issue 6658 https://doi.org/10.1126/science.adh1853	journal	August 2023
Dependence of Micelle Size and Shape on Detergent Alkyl Chain Length and Head Group Oliver, Ryan C.; Lipfert, Jan; Fox, Daniel A. PLoS ONE, Vol. 8, Issue 5 https://doi.org/10.1371/journal.pone.0062488	journal	May 2013
A Novel Approach to Stabilize Foam Using Fluorinated Surfactants Kamal, Muhammad Shahzad Energies, Vol. 12, Issue 6 https://doi.org/10.3390/en12061163	journal	March 2019
Fischer–Tropsch Synthesis for Light Olefins from Syngas: A Review of Catalyst Development Yahyazadeh, Arash; Dalai, Ajay K.; Ma, Wenping Reactions, Vol. 2, Issue 3 https://doi.org/10.3390/reactions2030015	journal	July 2021

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