Mechanistic study of maleic anhydride grafting onto fatty double bonds using mass spectrometry

Rapid Communications in Mass Spectrometry : RCM
Corinne Loutelier-BourhisCatherine M Lange

Abstract

The grafting of maleic anhydride onto fatty C=C double bonds is a well-known and used method to functionalize triglyceride molecules. Nevertheless, grafted products are not actually structurally well defined. In this work, the thermal grafting of maleic anhydride onto (un)saturated fatty acid esters without the use of an initiator was characterized in order to determine the nature of the products formed during this reaction. Complementary spectrometric techniques, ESI-MS(n) (ion-trap mass spectrometer), IMS-MS(n) (Q-IMS-TOFMS) and GC/MS, were used to identify the grafted products which were prepared using either ethyl oleate (EtO) or methyl linoleate (MeL) as model molecules and maleic anhydride (MA). Lithiated adducts were investigated since they yield useful structural information when subjected to collision-induced dissociation (CID) in tandem mass spectrometry. A high number of products are formed during MA grafting and various reaction types could occur. Radical addition of maleic anhydride followed by combination or elimination reactions led to succinic and maleic anhydride grafting, respectively. The addition occurred with or without double-bond shift; the resulting derivatives showed succinic and maleic anhydride branch...Continue Reading

References

Jul 1, 1955·British Journal of Industrial Medicine·J P GILMAN, S D VESSELINOVITCH
Sep 24, 2004·Rapid Communications in Mass Spectrometry : RCM·Kevin GilesRobert H Bateman
Apr 11, 2006·Applied Microbiology and Biotechnology·J O Metzger, U Bornscheuer
Jan 8, 2009·Rapid Communications in Mass Spectrometry : RCM·Eric C Y ChanLin Tang Goh
Apr 1, 1990·Journal of the American Society for Mass Spectrometry·J S CrockettR T Holman

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Citations

May 15, 2015·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Kyun Joo ParkDo Hyun Kim

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