Mechanisms of flash pyrolysis of ether lipids isolated from the green microalga Botryococcus braunii race A

Gelin, François; Gatellier, J.-P.L.A.; Damsté, Jaap S. Sinninghe; Metzger, Pierre; Derenne, Sylvie; Largeau, Claude; Leeuw, J.W. de

doi:10.1016/0165-2370(93)80006-l

Cited by 41 publications

(8 citation statements)

References 28 publications

(1 reference statement)

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“…Analysis of the degradation products of the model compounds revealed that the position and nature of functional groups in the alkyl chain dictate the series of pyrolysis products formed. Recognition of these specific degradation products and their mode of formation can provide clues to the chemical structures The thermal degradation mechanisms proposed for several model compounds in this study confirmed the results obtained by the Curie-point pyrolysis of ether lipids isolated from the green microalga BotrJ)coccus hraunii [8]. Spectroscopic techniques (IR, 'H NMR and "C NMR) and chemolysis experiments, such as ozonolysis, elucidated the structures of two types of ether lipids isolated from two different strains of this microalga [36].…”

Section: Discussionsupporting

confidence: 72%

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Curie-point pyrolysis of sodium salts of functionalized fatty acids

Hartgers

Damsté

Leeuw

1995

Journal of Analytical and Applied Pyrolysis

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Selected sodium salts of functionalized fatty acids were subjected to Curie-point pyrolysis and their pyrolysis products subsequently analyzed by gas chromatography/mass spectrometry in order to study the thermal dissociation mechanisms of lipid moieties in bio-and geomacromolecules.Pyrolysis of the sodium salts of hydroxy and keto acids yields in each case a methylketone as the major product, which is generated via a concerted, six-membered ring rearrangement triggered by the functionality in the alkyl chain. The thermal dissociation of alkylbenzene and alkylthiophene moieties proceeds mainly via hydrogen abstraction at the Xand ;I-carbon atoms, followed by /I-scission.The ratios of the main product pairs, i.e. styrene/toluene and vinylthiophene/2-methylthiophene, are largely controlled by radical mobility during pyrolysis. The major fragmentation pathway of monounsaturated alkyl chains is /I-cleavage adjacent to the double bond. The identification of both Z and E isomers of alkenes in the pyrolysates demonstrates that the initial stereospecifity of the double bond is not retained during pyrolysis. The formation of linear alkylbenzenes from non-phenylic precursor moieties (e.g. diunsaturated fatty acids) shows that specific alkylbenzenes in Curie-point pyrolysates are not always derived from monoaromatic precursors. The addition of organic or mineral matter suppresses these secondary processes. The extension of the model compound results to the recognition of specific types of pyrolysis products and their relevance to the reconstruction of structures of lipid moieties in natural biomacromolecules in kerogens and coals are discussed.

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Section: Discussionsupporting

confidence: 72%

“…Their structural relationship is revealed by similar types of pyrolysis products, i.e. aldehydes and ketones, which are generated via analogous degradation pathways [8]. For example, octadecanal is proposed to result from a-cleavage adjacent to the hydroxyl group.…”

Section: Discussionmentioning

confidence: 99%

Curie-point pyrolysis of sodium salts of functionalized fatty acids

Hartgers

Damsté

Leeuw

1995

Journal of Analytical and Applied Pyrolysis

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“…To date, studies conducted to evaluate the pyrolytic characteristics of algae have primarily focused on microalgae such as Dunaliella (Ginzburg, 1993;Minowa et al, 1995), Botryococcus braunii (Gelin et al, 1993;Dote et al, 1994), Spirulina platensis (Peng et al, 2001), Chlorella protothecoides (Peng et al, 2001;Miao and Wu, 2004;Xu et al, 2006) and Nannochloris sp. UTEX LB1999 (Yamaberi et al, 1998).…”

Section: Introductionmentioning

confidence: 99%

Evaluation of the pyrolytic and kinetic characteristics of Enteromorpha prolifera as a source of renewable bio-fuel from the Yellow Sea of China

Chen

Zhao

et al. 2010

Chemical Engineering Research and Design

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“…The ketones can be formed, upon pyrolysis, by homolytic cleavage of ether bonds (Gelin et al, 1993(Gelin et al, , 1994, which participate in the macromolecular network of many algaenans Derenne et al, 1989;Gelin et al, 1996). The isoprenoid ketone 6,10,14-trimethyl-2-pentadecanone may originate from a similar isoprenoid algaenan to that mentioned above (see Behar et al, 1995).…”

Section: Sources Of the Pyrolysis Productsmentioning

confidence: 99%

Changes in kerogen composition across an oxidation front in Madeira Abyssal Plain turbidites as revealed by pyrolysis GC-MS

Damsté¹,

Hoefs²,

Leeuw³

et al. 1998

Proceedings of the Ocean Drilling Program, 157 Scientific Results

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Isolated kerogens from Madeira Abyssal Plain turbidite samples were qualitatively and semiquantitatively studied by means of analytical pyrolysis for the effect of oxygen exposure on organic matter preservation. The initial organic matter in the turbidite is very homogeneous and relatively high and offers an ideal case for the study of oxygen effects on organic matter preservation without the usual complications of varying sources or sedimentation rates and bioturbation. From all four studied turbidites, one sample from the oxidized part of the turbidite was compared with two samples from the unoxidized part. The aliphatic character of the kerogens after postdepositional oxidation has increased significantly, as revealed by the abundance of the n-alkanes and n-alk-1-enes in the oxidized turbidite. At the same time, the contribution of the isoprenoid alkanes and alkenes and the alkylthiophenes to the pyrolysate has decreased significantly. The relative abundances of alkylbenzenes, alkylnaphthalenes, alkylphenols, alkylindenes, and alkan-2-ones in the pyrolysates have remained relatively constant upon oxidation. The alkylbenzene, alkylphenol, alkylnaphthalene, n-alkane, and n-alk-1-ene, isoprenoid alkane, and alkene internal distributions are substantially altered in the oxidized samples. This study shows that postdepositional oxidation of sedimentary organic matter by oxygen is far more severe than by sulfate alone. Furthermore, it is clear that oxidation of the organic matter is, to a significant degree, selective.

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Mechanisms of flash pyrolysis of ether lipids isolated from the green microalga Botryococcus braunii race A

Cited by 41 publications

References 28 publications

Curie-point pyrolysis of sodium salts of functionalized fatty acids

Curie-point pyrolysis of sodium salts of functionalized fatty acids

Evaluation of the pyrolytic and kinetic characteristics of Enteromorpha prolifera as a source of renewable bio-fuel from the Yellow Sea of China

Changes in kerogen composition across an oxidation front in Madeira Abyssal Plain turbidites as revealed by pyrolysis GC-MS

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