The acetalization of glyoxal by vicinal diols

Sangsari, Farid Hamedi; Chastrette, F.; Chastrette, M.; Blanc, A.; Mattioda, G.

doi:10.1002/recl.19901090103

Cited by 5 publications

(2 citation statements)

References 15 publications

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“…The effective gas/particle phase equilibrium constants correlate with the hydroxyl groups per molecule of the aerosol material, suggesting that other uptake mechanisms besides hydration and oligomerization of glyoxal are operative. Nucleophilic attacks on glyoxal by alcohols have been observed in the bulk phase ,– . Direct chemical reaction with seed aerosol materials cannot explain all the observed glyoxal uptake, however.…”

Section: Resultsmentioning

confidence: 99%

Uptake of Glyoxal by Organic and Inorganic Aerosol

Corrigan

Hanley

Haan

2008

Environ. Sci. Technol.

101

116

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The uptake of glyoxal by a variety of organic and inorganic aerosol types was examined in a Teflon chamber. Rapid glyoxal uptake was observed for all liquid-phase aerosols at all relative humidity levels tested (< 5 to 50% RH). Even for aerosol with known water content, Henry's Law cannot predict glyoxal uptake: H* > (3 +/- 1.5) x 10(8) mol kg(-1) atm(-1) for l-tartaric acid, H* > (1 +/- 0.5) x 10(8) for dl-malic acid and H* = (2 +/- 1) x 10(7) for malonic acid aerosol. Other liquid-phase aerosol particles containing amine functional groups (arginine, aspartic acid, and glutamic acid) took up even more glyoxal (H* > 3 x 10(8)). The trend of higher glyoxal uptake onto aerosol containing more nucleophilic organic compounds suggests that glyoxal is reacting with organic compounds in the aerosol phase. Solid-phase aerosol showed RH-dependent glyoxal uptake, likely due to the existence of surface water layers. However, particle growth rates were the highestfor sodium sulfate aerosol. For organic aerosol, growth rates correlated with the acidity of the carboxylic acid groups of the aerosol material, suggesting that glyoxal uptake is enhanced by mildly acidic conditions.

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Section: Resultsmentioning

confidence: 99%

Uptake of Glyoxal by Organic and Inorganic Aerosol

Corrigan

Hanley

Haan

2008

Environ. Sci. Technol.

101

116

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“…[3][4][5] To gain a better insight into the network of glyoxal-treated cotton, 13 C-NMR studies of the reaction of glyoxal with diols in solution were also conducted. 14,15 Because glyoxal is a difunctional aldehyde, the formation of bis acetals or bis semiacetals can be taken into consideration. 16 However, to date it is not possible to differentiate between this two possibilities.…”

Section: Resultsmentioning

confidence: 99%

Quantitative evaluation of cotton‐bound glyoxal in the presence of glycols

Schramm

Rinderer

2003

J of Applied Polymer Sci

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Cotton fabric is modified chemically to convey crease resistance to the cellulosic material by means of an appropriate crosslinking agent. For this purpose glyoxal was tested as a nonformaldehyde durable press agent. The cotton-bound glyoxal can be quantified by means of isocratic HPLC, whereby the glyoxal-treated fabric is hydrolyzed by a NaOH solution. During this pretreatment glyoxal is extracted from the cellulosic sample and converted into glycolate by an internal Cannizzaro reaction. The addition of glycols such as ethylene glycol or diethylene glycol into the formulation results in a remarkable decrease of the amount of glyoxal that is detected. This phenomenon can be explained by the fact that the glycol reacts with the glyoxal, thus hampering the internal Cannizzaro reaction. The acidic hydrolysis and the alkaline hydrolysis provide the same results, thus indicating that the alkaline treatment removes all the cotton-bound glyoxal.

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ChemInform Abstract: The Acetalization of Glyoxal by Vicinal Diols.

Sangsari

Chastrette

et al. 1990

ChemInform

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206 ChemInform Abstract The structure and stereochemistry of products obtained from hemiacetalization and acetalization of glyoxal (I) with various diols are established by 13C NMR. Hemiacetalization of (I) with 1,2-ethanediol, cis-1,2-cyclohexanediol or trans-1,2-cyclohexanediol yields the dioxanediols (II)-(IV) regardless of the diol reacted. The course of acetalization depends on the structure of the diol: 1,2-ethanediol or cis-1,2-cyclohexanediol yield mixtures containing mostly the dioxolanes (V) or (VI), while trans-1,2-cyclohexanediol affords only the tetraoxadecalins (VII) and (VIII). The isomer ratios of the products depend on the reaction conditions.

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The acetalization of glyoxal by vicinal diols

Cited by 5 publications

References 15 publications

Uptake of Glyoxal by Organic and Inorganic Aerosol

Uptake of Glyoxal by Organic and Inorganic Aerosol

Quantitative evaluation of cotton‐bound glyoxal in the presence of glycols

ChemInform Abstract: The Acetalization of Glyoxal by Vicinal Diols.

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