Derivatization with acetic anhydride: Applications to the analysis of biogenic amines and psychiatric drugs by gas chromatography and mass spectrometry

Baker, Glen B.; Coutts, Ronald T.; Holt, Andrew

doi:10.1016/1056-8719(94)90076-0

Cited by 22 publications

(5 citation statements)

References 51 publications

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“…The location of the hydroxyl groups was confirmed by performing GC-MS analyses of effluent extracts that had been derivatized with aqueous acetic anhydride. This derivatization technique is specific for phenolic hydroxyl substituents and does not result in the acetylation of alkyl hydroxyl substituents (17). The mass spectrum for a hydroxylated degradation product of acetochlor and the spectrum for its acetylated derivatized complement are shown in Figure 6 as an example.…”

Section: Resultsmentioning

confidence: 99%

Degradation of Chloroacetanilide Herbicides by Anodic Fenton Treatment

Friedman

Lemley

2006

J. Agric. Food Chem.

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Anodic Fenton treatment (AFT) is an electrochemical treatment employing the Fenton reaction for the generation of hydroxyl radicals, strong oxidants that can degrade organic compounds via hydrogen abstraction. AFT has potential use for the remediation of aqueous pesticide waste. The degradation rates of chloroacetanilides by AFT were investigated in this work, which demonstrates that AFT can be used to rapidly and completely remove chloroacetanilide herbicides from aqueous solutions. Acetochlor, alachlor, butachlor, metolachlor, and propachlor were treated by AFT, and parent compound concentrations were analyzed over the course of the treatment time. Degradation curves were plotted and fitted by the AFT kinetic model for each herbicide, and AFT model kinetic parameters were used to calculate degradation rate constants. The reactivity order of these five active ingredients toward hydroxyl radical was acetochlor approximately metolachlor > butachlor approximately alachlor > propachlor. Treatment of the chloroacetanilides by AFT removed the parent compounds but did not completely mineralize them. However, AFT did result in an increase in the biodegradability of chloroacetanilide aqueous solutions, as evidenced by an increase in the 5-day biochemical oxygen demand to chemical oxygen demand ratio (BOD5/COD) to>0.3, indicating completely biodegradable solutions. Several degradation products were formed and subsequently degraded, although not always completely. Some of these were identified by mass spectral analyses. Among the products, isomers of phenolic and carbonyl derivatives of parent compounds were common to each of the herbicides analyzed. More extensively oxidized products were not detected. Degradation pathways are proposed for each of the parent compounds and identified products.

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Section: Resultsmentioning

confidence: 99%

Degradation of Chloroacetanilide Herbicides by Anodic Fenton Treatment

Friedman

Lemley

2006

J. Agric. Food Chem.

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“…The light end typically comprises DMAE and TMEDA, while the heavy end typically consists of N,N-dimethylglucamine and 4-dimethylamino-1,2,3-butanetriol. The latter are subject to acetylation, as used for alcohol and amino groups in drug analysis prior to analysis [30]. The carbon balance, based on the carbon atoms from the reactant glucose, could be closed for at least 75% in every experiment, with a single exception for the experiment where the catalyst to glucose ratio was the lowest and degradation reactions were most prominent.…”

Section: Parameter Estimationmentioning

confidence: 99%

Kinetics of homogeneous and heterogeneous reactions in the reductive aminolysis of glucose with dimethylamine

Poissonnier

Pelckmans

Waes³

et al. 2018

Applied Catalysis B: Environmental

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“…Derivatization reactions ranging from silylation to alkylation to acylation have constituted useful modifications for polar compounds in the analytical chemist's toolbox for use in GC-MS analyses [4][5][6]. In our field of study, these reactions have experienced exhaustive use in accomplishing the modification of compounds related to the chemical weapons convention (CWC) [7][8][9]. Nevertheless, an analyte's polarity and thus low propensity to volatilize is not the only characteristic that may prevent its detection by GC-MS. One such example is pinacolyl alcohol (PA, 3,3-dimethyl-2-butanol, CAS No: 464-07-3) that due to its low molecular weight (MW = 102) and early elution time during routine GC-MS analysis (RT ~ 4.1 min), it is a challenging analyte to detect, particularly in situations where more abundant interferences with similar or equal retention times are present.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Use of carbonyldiimidazole as a derivatization agent for the detection of pinacolyl alcohol, a forensic marker for Soman, by EI‐GC–MS and LC‐HRMS in official OPCW proficiency test matrices

Valdez,

Kaseman,

Dreyer

et al. 2024

Journal of Forensic Sciences

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Pinacolyl alcohol (PA), a key forensic marker for the nerve agent Soman (GD), is a particularly difficult analyte to detect by various analytical methods. In this work, we have explored the reaction between PA and 1,1′‐carbonyldiimidazole (CDI) to yield pinacolyl 1H‐imidazole‐1‐carboxylate (PIC), a product that can be conveniently detected by gas chromatography–mass spectrometry (GC–MS) and liquid chromatography‐high‐resolution mass spectrometry (LC‐HRMS). Regarding its GC–MS profile, this new carbamate derivative of PA possesses favorable chromatographic features such as a sharp peak and a longer retention time (RT = 16.62 min) relative to PA (broad peak and short retention time, RT = 4.1 min). The derivative can also be detected by LC‐HRMS, providing an avenue for the analysis of this chemical using this technique where PA is virtually undetectable unless present in large concentrations. From a forensic science standpoint, detection of this low molecular weight alcohol signals the past or latent presence of the nerve agent Soman (GD) in a given matrix (i.e., environmental or biological). The efficiency of the protocol was tested separately in the analysis and detection of PA by EI‐GC–MS and LC‐HRMS when present at a 10 μg/mL in a soil matrix featured in the 44th PT and in a glycerol‐rich liquid matrix featured in the 48th Official Organization for the Prohibition of Chemical Weapons (OPCW) Proficiency Test when present at a 5 μg/mL concentration. In both scenarios, PA was successfully transformed into PIC, establishing the protocol as an additional tool for the analysis of this unnatural and unique nerve agent marker by GC–MS and LC‐HRMS.

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Derivatization with acetic anhydride: Applications to the analysis of biogenic amines and psychiatric drugs by gas chromatography and mass spectrometry

Cited by 22 publications

References 51 publications

Degradation of Chloroacetanilide Herbicides by Anodic Fenton Treatment

Degradation of Chloroacetanilide Herbicides by Anodic Fenton Treatment

Kinetics of homogeneous and heterogeneous reactions in the reductive aminolysis of glucose with dimethylamine

Use of carbonyldiimidazole as a derivatization agent for the detection of pinacolyl alcohol, a forensic marker for Soman, by EI‐GC–MS and LC‐HRMS in official OPCW proficiency test matrices

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