Trimethylsulfonium hydroxide as derivatization reagent for the chemical investigation of drying oils in works of art by gas chromatography

Dron, Julien; Linke, Robert; Rosenberg, Erwin; Schreiner, Manfred

doi:10.1016/j.chroma.2004.06.013

Cited by 36 publications

(29 citation statements)

References 26 publications

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“…For both GC's, injection and detection were performed at 2758C and the column temperature was set at 1808C. Before analyses, the products were transmethylated according to a published procedure [22] using trimethylsulfonium hydroxide (0.25 M in methanol). A typical product (100 mg) was dissolved in methyl tert-butyl ether (5 mL).…”

Section: Methodsmentioning

confidence: 99%

Synthesis and properties of highly branched Jatropha curcas L. oil derivatives

Daniel

Ardiyanti

Schuur

et al. 2011

Euro J Lipid Sci & Tech

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The synthesis and properties of a number of novel branched Jatropha curcas L. oil (JO) derivatives containing vicinal di-ester units in the fatty acid chains are reported. Both the length (acetyl vs. hexanoyl) and the stereochemistry of the vicinal di-ester units (cis vs. trans) were varied. The compounds were prepared by two different synthetic approaches using catalytic chemistry. The first approach involves epoxidation of JO using a Sharpless epoxidation with methyltrioxorhenium as the catalyst to give epoxidized JO (1), followed by an esterification reaction with the corresponding anhydrides using ammonium-12-molybdophosphate (AMP) as catalyst to give trans-di-esters of JO (4a, 4b). The second approach is based on the dihydroxylation of JO using either the Prilezhaev method, resulting in trans-diols of JO (2), or the Upjohn method using osmium tetroxide as catalyst to give cis-diols of JO (3). In subsequent steps, the diols were esterified with acetic-or hexanoic anhydride using dimethylaminopyridine as catalyst to produce the corresponding cis-and trans-di-esters of JO (5a, 5b, 6). The best cold flow properties (lowest pour-and cloud point, crystallization and melting temperature) were obtained for JO with hexanoyl branches in a trans orientation (5b, pour point of À148C, melting point of À58C, and crystallization temperature of À258C) and these values are considerably better than for the JO source.Practical applications: Jatropha curcas L. oil (JO) is a toxic oil with potential applications not only as a green biodiesel but also as a feedstock for the oleochemical industry. The toxicity prohibits the use in food products but does not interfere with technical applications. Here we report studies on the synthesis of interesting JO derivatives (epoxidized, dihydroxylated, and branched compounds) that could be useful starting materials for a range of derivatives with a broad application perspective. The branched JO derivatives with vicinal di-ester units in the fatty acid chains have cold flow properties (pour-and cloud point, melting point and crystallization temperature) considerably better than the original JO. In addition, the oxidative stability was also improved significantly. These novel branched JO derivatives may have interesting applications as cold-flow improvers for biodiesel or as biolubricants.

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Section: Methodsmentioning

confidence: 99%

Synthesis and properties of highly branched Jatropha curcas L. oil derivatives

Daniel

Ardiyanti

Schuur

et al. 2011

Euro J Lipid Sci & Tech

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“…a wide range of substances, such as for the identification of oils, resins and hydrocarbons simultaneously [18,19]. The intention by using this procedure is to investigate the additives, which could be present in Chinese ink sticks.…”

Section: Sample Preparationmentioning

confidence: 99%

Characterization of the materials used in Chinese ink sticks by pyrolysis-gas chromatography–mass spectrometry

Wei

Fang

Cao

et al. 2011

Journal of Analytical and Applied Pyrolysis

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“…Most of the literature related to the TMSH is associated with the determination of lipids, fatty acids or triglycerides including waxes and their related compounds. TMPAH and/or TMSH were used for methylation of organic materials in artworks [34,37], determination carbamate pesticides [38], for O-methyl derivatives from lipids containing hydroxyl groups [39] and for methylation of lipids [40].…”

Section: Thermally Assisted Methylation By Trimethylsulfonium Hydroxidementioning

confidence: 99%

Thermally assisted methylation and subsequent silylation of scheduled acids of chemical weapon convention for on-site analysis and its comparison with the other methods of methylation

Amphaisri

Palit

Mallard

2011

Journal of Chromatography A

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Trimethylsulfonium hydroxide as derivatization reagent for the chemical investigation of drying oils in works of art by gas chromatography

Cited by 36 publications

References 26 publications

Synthesis and properties of highly branched Jatropha curcas L. oil derivatives

Synthesis and properties of highly branched Jatropha curcas L. oil derivatives

Characterization of the materials used in Chinese ink sticks by pyrolysis-gas chromatography–mass spectrometry

Thermally assisted methylation and subsequent silylation of scheduled acids of chemical weapon convention for on-site analysis and its comparison with the other methods of methylation

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