Kinetics and pathways for an algal phospholipid (1,2-dioleoyl-sn-glycero-3- phosphocholine) in high-temperature (175-350 °c) water

Shujauddin Changi, Adam J. Matzger, Phillip E. Savage

Research output: Contribution to journalArticle

25 Scopus citations

Abstract

We examined the behavior of 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) in high-temperature water at 175, 200, 225, and 350 °C. DOPC hydrolyzed to give oleic acid and a number of phosphorus-containing products. The hydrolysis was catalyzed by oleic and phosphoric acids, which were also reaction products. DOPC formed 1-acyl and 2-acyl lyso-phosphatidylcholine (LPC) along with oleic acid as primary products. LPC subsequently formed other phosphorus-containing intermediates, which finally led to phosphoric acid as the ultimate P-containing product. At 350 °C, phosphoric acid and oleic acid were the only products observed. We observed an ester of oleic acid and glycerol (9-octadecenoic-2,3- dihydroxypropyl ester), which likely formed via the hydrolysis of LPC. A reaction network is proposed to explain the formation of the observed products. A quantitative kinetics model based on the proposed pathways was consistent with the experimental data.

Original languageEnglish (US)
Pages (from-to)2856-2867
Number of pages12
JournalGreen Chemistry
Volume14
Issue number10
DOIs
StatePublished - Oct 2012

All Science Journal Classification (ASJC) codes

  • Environmental Chemistry
  • Pollution

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