Biodegradability and Toxicity of Cellobiosides and Melibiosides

David E. Hogan, Fei Tian, Scott W. Malm, Laurel L. Kegel, Lajos Z. Szabó, Anoop S. Hunjan, Jeanne E. Pemberton, Walter T. Klimecki, Robin Polt, Raina M. Maier

Research output: Contribution to journalArticlepeer-review

Abstract

In 2014, almost 16 million tons of surfactants were used globally for cleaning and industrial applications. As a result, massive quantities disperse into environmental compartments every day. There is great market interest in developing highly biodegradable, less-toxic, and renewable alternatives to currently used petroleum-based surfactants. Glycolipid surfactants, composed of a sugar headgroup and lipid tail, are effective surfactants and emulsifiers with a high tolerance to electrolytes and are easily tailored to address specific needs. The green synthesis and surfactant characteristics of a suite of cellobiosides and melibiosides were recently described. The biodegradability and toxicity of 1°-alkyl-O-cellobiosides, 2°-alkyl-O-cellobiosides, and 1°-alkyl-O-melibiosides with straight-chain alkyl tails of 8, 10, and 12 are reported in this study. Biodegradability was assessed by quantifying mineralization (CO2 evolution). All of the glycosides were inherently biodegradable and most were readily biodegradable according to OECD and US environmental protection agency (EPA) definitions. The Microtox acute toxicity assay showed both chain length and headgroup had significant effects on toxicity, but most of the molecules were practically nontoxic according to EPA definitions with EC50 values >100 mg L−1. Cytotoxicity to human lung (H1299) and keratinocyte cell lines (HaCaT) was measured by xCELLigence and MTS assays. Cytotoxicity values were comparable to similar glycosides previously reported. IC50 values were determined but in general, exceeded surfactant concentrations that are found in the environment. These data demonstrate the promising nature of these molecules as green alternatives to petrochemical surfactants.

Original languageEnglish (US)
Pages (from-to)715-724
Number of pages10
JournalJournal of Surfactants and Detergents
Volume23
Issue number4
DOIs
StatePublished - Jul 1 2020

Keywords

  • Biodegradability
  • Cellobioside
  • Glycosides
  • Melibioside
  • Surfactants
  • Toxicity

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Physical and Theoretical Chemistry
  • Surfaces, Coatings and Films

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