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Issue 10, 2012
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Kinetics and pathways for an algal phospholipid (1,2-dioleoyl-sn-glycero-3-phosphocholine) in high-temperature (175–350 °C) water

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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.

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

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Publication details

The article was received on 26 Apr 2012, accepted on 10 Jul 2012 and first published on 10 Jul 2012


Article type: Paper
DOI: 10.1039/C2GC35639B
Citation: Green Chem., 2012,14, 2856-2867
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    Kinetics and pathways for an algal phospholipid (1,2-dioleoyl-sn-glycero-3-phosphocholine) in high-temperature (175–350 °C) water

    S. Changi, A. J. Matzger and P. E. Savage, Green Chem., 2012, 14, 2856
    DOI: 10.1039/C2GC35639B

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