Synthesis of Butyl-Exchanged Polyoxymethylene Ethers as Renewable Diesel Blendstocks with Improved Fuel Properties

Daniel Ruddy, Martha Arellano-Trevino, Danielle Bartholet, Anh To, Andrew Bartling, Frederick Baddour, Teresa Alleman, Earl Christensen, Gina Fioroni, Cameron Hays, Jon Luecke, Junqing Zhu, Charles McEnally, Lisa Pfefferle, Kenneth Reardon, Thomas Foust

Research output: Contribution to journalArticlepeer-review

9 Scopus Citations

Abstract

Methyl-terminated polyoxymethylene ethers (MM-POMEs), having the formula CH3O−(CH2O)n−CH3 (n = 3−5), are a high-cetane, low-sooting group of oxygenates that have recently attracted attention as potential diesel blendstocks. Despite these attractive fuel properties, MM-POMEs have shortcomings due to their low energy density and high water solubility. Guided by a computational fuel property assessment for POMEs with longer end-groups, the most promising improvements in the desired compression ignition fuel properties were observed for butyl-terminated POMEs. Here, an acid-catalyzed transacetalization reaction was developed to exchange the methyl end-groups of MM-POMEs (n = 3−6) with butyl end-groups. The reaction utilizes an ion-exchange resin as the acid catalyst at mild reaction conditions of 60 °C and atmospheric pressure. Approximately 100 mL of butyl-exchanged POMEs in the diesel boiling range were produced, enabling laboratory-scale fuel property testing. The butyl-terminated POME mixture possesses the advantaged fuel properties of the parent MM-POMEs (low-soot, high-cetane) while exhibiting improved energy density (lower heating value (LHV) of 30 MJ/kg) and substantially reduced water solubility (7.3 g/L) compared to the parent MM-POME mixture (LHV of 19 MJ/kg, water solubility of 258 g/L).

Original languageAmerican English
Pages (from-to)6266-6273
Number of pages8
JournalACS Sustainable Chemistry and Engineering
Volume9
Issue number18
DOIs
StatePublished - 10 May 2021

Bibliographical note

Publisher Copyright:
© 2021 American Chemical Society

NREL Publication Number

  • NREL/JA-5100-79006

Keywords

  • Bio-derived blendstocks
  • Lower heating value
  • Polyoxymethylene ethers
  • Transacetalization
  • Water solubility

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