Formation of long-chain ketones in archaeological pottery vessels by pyrolysis of acyl lipids

Raven, AM; Bergen, PF van; Stott, AW; Dudd, Stephanie N.; Evershed, Richard P.

doi:10.1016/s0165-2370(97)00036-3

Cited by 133 publications

(131 citation statements)

References 21 publications

Supporting

Mentioning

115

Contrasting

Unclassified

Order By: Relevance

“…It is probable that the chemistry of a pottery fabric, including the presence of metal ions such as iron and copper within the clay, will affect the formation and preservation of residues. There is evidence for this in the formation of ketones in heated fats when metal oxides are present in the ceramic fabric (23,24). Formation and preservation of residues may also be affected by the physical nature of the ceramic (coarseness, degree of firing etc).…”

Section: Residue Formation and Preservationmentioning

confidence: 99%

Organic Residues in Archaeology: The Highs and Lows of Recent Research

Steele

2013

ACS Symposium Series

View full text Add to dashboard Cite

The analysis of organic residues from archaeological materials has become increasingly important to our understanding of ancient diet, trade and technology. Residues from diverse contexts have been retrieved and analysed from the remains of food, medicine and cosmetics to hafting material on stone arrowheads, pitch and tar from shipwrecks, and ancient manure from soils. Research has brought many advances in our understanding of archaeological, organic residues over the past two decades. Some have enabled very specific and detailed interpretations of materials preserved in the archaeological record. However there are still areas where we know very little, like the mechanisms at work during the formation and preservation of residues, and areas where each advance produces more questions rather than answers, as in the identification of degraded fats. This chapter will discuss some of the significant achievements in the field over the past decade and the ongoing challenges for research in this area.1341280_File000001_20903114.docPrinted 7/19/2013 2

show abstract

Section: Residue Formation and Preservationmentioning

confidence: 99%

Organic Residues in Archaeology: The Highs and Lows of Recent Research

Steele

2013

ACS Symposium Series

View full text Add to dashboard Cite

show abstract

“…As it can be seen in (Fig 8) 14-heptacosanone, a symmetric mid chain ketone after γ-H transfer and six centre rearrangement to form dominant 1-dodecene and enol product, 2-hydroxy-1-pentadecene, which by keto-enol tautomerism, form 2-pentadecanone [34,36]. The resulting ketone, 2-pentadecanone then undergoes the same mechanism to produce 1-dodecene.…”

Section: Pyrolysis Mechanisms Of Calcium Magnesium and Sodium Salts mentioning

confidence: 90%

“…The formation of 2-pentadecanone and 1-dodecene proceeds by a γ-hydrogen transfer mechanism [34,36]. As it can be seen in (Fig 8) 14-heptacosanone, a symmetric mid chain ketone after γ-H transfer and six centre rearrangement to form dominant 1-dodecene and enol product, 2-hydroxy-1-pentadecene, which by keto-enol tautomerism, form 2-pentadecanone [34,36].…”

Section: Pyrolysis Mechanisms Of Calcium Magnesium and Sodium Salts mentioning

confidence: 93%

See 1 more Smart Citation

Organic compound-mineral interactions: Using flash pyrolysis to monitor the adsorption of fatty acids on calcite

Zafar

Watson

Weiß

et al. 2017

Journal of Analytical and Applied Pyrolysis

View full text Add to dashboard Cite

Fatty acids are near ubiquitous organic compounds in living organisms in the Earth's biosphere. Following death of an organism in the marine environment its fatty acids may survive descent to the sea bed where they can be juxtaposed with minerals. The aim of this study was to investigate the interaction of fatty acids with the common marine mineral calcite. Adsorption of tetradecanoic acid (C14) on calcite results in a sigmoidal or "s" isotherm. Flash pyrolysis experiments were conducted on samples of fatty acid adsorbed onto calcite and were compared with similar experiments on pure fatty acid and on salts of a fatty acid. Flash pyrolysis of pure tetradecanoic acid generated unsaturated and saturated hydrocarbons and a series of unsaturated and saturated low molecular weight fatty acids.Flash pyrolysis of free tetradecanoic acid salt produced saturated and unsaturated hydrocarbons, an aldehyde and a homologous series of saturated and unsaturated ketones, one of which was a symmetrical mid chain ketone (14-heptacosanone). Flash pyrolysis data from adsorbed tetradecanoic acid samples suggested that adsorption is analogous to the formation of the calcium salt of tetradecanoic acid. A key characteristic of the flash pyrolysis products of adsorbed fatty acids and fatty acid salts was the production of ketones with higher molecular weights than the starting fatty acids. Ketonisation was not observed from the flash pyrolysis of pure acid which implied the catalytic significance of the calcite mineral surface.The abundance of hydrocarbons relative to ketones in the pyrolysates negatively correlated with the proportion of fatty acids adsorbed to the surface of calcite. The ability to use flash pyrolysis to diagnose the nature of fatty acid interactions with mineral surfaces provides a valuable tool for monitoring the fate of these important lipids at the Earth's surface as they pass into the geosphere and are subjected to diagenetic processes.

show abstract

“…However, further studies of cooking of leafy vegetables of an Early Bronze Age cooking vessel show that the three major saturated long-chain ketones (the C 31 , C 33 and C 35 ) in the total lipids extract have δ 13 C values of -26.8, -26.5 and -25.9‰ respectively (Raven et al 1997). These compounds are too enriched (c. 10‰) in 13 C to be derived from epicuticular leaf waxes of Brassica oleracea (-35.4‰).…”

Section: Evershed 2009; Regert 2011)mentioning

confidence: 96%