107-22-2

Basic information

• Product Name: 1,2-Ethanedione
• Synonyms: Biformyl;sell glyoxal;Glyoxylaldehyde;Diformyl;Glyfix CS 50;Permafresh 114;Glyoxal, Biformyl, Oxalaldehyde;Daicel GY 60;Gohsezal P;oxaldehyde;Oxalaldehyde;Ethanedial;Glyoxal 40%;GLYOXAL, 29.2%;Glyoxal Solution;Glyoxal water solution 30%
• CAS NO: 107-22-2
• Molecular Formula: C2H2O2
• Molecular Weight: 58.03608
• EINECS: 203-474-9
• Mol File: 107-22-2.mol
• Article Data: 52

Chemical Properties

• Melting Point: -14℃
• Boiling Point: 50 °C at 760 mmHg
• Flash Point: 104°C
• Appearance: white or off-white crystalline powder
• Density: 1.032 g/cm³
• Vapor Pressure: 292mmHg at 25°C
• Refractive Index: 1.337
• Water Solubility: miscible
• CAS DataBase Reference: 1,2-Ethanedione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Ethanedione(107-22-2)
• EPA Substance Registry System: 1,2-Ethanedione(107-22-2)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R20:; R36/38:; R43:; R68:
• Safety Statements: S36/37:
• Hazardous Substances Data: 107-22-2(Hazardous Substances Data)

Usage

General Description

1,2-Ethanedione, also known as acetyl methyl carbinol or methyl acetyl ketone, is a chemical compound with the molecular formula C3H4O2. It is a colorless, volatile liquid with a strong, pungent odor. 1,2-Ethanedione is commonly used as a building block in the synthesis of various chemicals and pharmaceuticals. It is also used in the production of various food flavorings and fragrances. However, 1,2-Ethanedione has been identified as a potential respiratory and skin irritant and has been classified as a hazardous substance. It is important to handle and store this chemical with caution to prevent any adverse health effects.

InChI:InChI=1/C2H2O2/c3-1-2-4/h1-2H

Upstream product

• 56-23-5 tetrachloromethane 
• 128-08-5 N-Bromosuccinimide 
• 121-44-8 triethylamine 
• 50-00-0 formaldehyd 
• 922-69-0 1,1-dimethoxyethylene 
• 4294-45-5 DL-threo-β-hydroxyaspartic acid 
• 127-65-1 chloroamine-T 
• 67-66-3 chloroform 
• 581-40-8 2,3-dimethylnaphthalene 
• 95-63-6 1,2,4-Trimethylbenzene 
• 107-21-1 ethylene glycol 
• 75-07-0 acetaldehyde 
• 56-81-5 glycerol 
• 646-06-0 1,3-DIOXOLANE 

Downstream Products

• 75793-17-8 2-phenyl-5-[1-furan-2-yl-meth-(Z)-ylidene]-3,5-dihydro-imidazol-4-one 
• 64158-25-4 2,2'-dimethylhydrobenzoin 
• 100728-71-0 2-p-tolyl-pteridin-4-ylamine 
• 100382-46-5 8-benzyl-8H-pteridin-2-one 
• 30834-76-5 glyoxal-bis(4-dimethylaminophenylimine) 
• 75-07-0 acetaldehyde 
• 15719-64-9 methylammonium carbonate 
• 5173-28-4 1,2-di-p-tolylethane-1,2-diol 
• 1433-78-9 glyoxal-bis-(2-hydroxy-5-nitro-phenylimine) 
• 67992-31-8 N-Cyclohexyl-N-(2-hydroxyethyl)-aminoessigsaeure 
• 67992-35-2 4-cyclohexyl-2,3-epoxy-morpholine 
• 67992-39-6 3,3'-dicyclohexyl-octahydro-[2,2']bioxazolyl 
• 1072-12-4 glycolaldehyde bis(thiosemicarbazone) 

Relevant articles and documents

Glycolaldehyde Production from Ethylene Glycol with Immobilized Alcohol Oxidase and Catalase

An enzymatic method for glycolaldehyde production from ethylene glycol was investigated using immobilized alcohol oxidase and catalase. Those enzymes were immobilized onto Chitopearl BCW 3501. When only alcohol oxidase was immobilized onto it, the apparent activity was 190 units/g in wet gel using methanol as the substrate. Tris-HCl buffer (1.5 M; pH 9.0) was selected based on a high stability of glycolaldehyde and a low production of glyoxal as a by-product. Under the optimum conditions, 0.97 M glycolaldehyde was formed from 1.0 M ethylene glycol and the ratio of glyoxal to glycolaldehyde was less than 1%.

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Glucose oxidation to formic acid and methyl formate in perfect selectivity

We report the highly remarkable discovery that glucose oxidation catalysed by polyoxometalates (POMs) in methanolic solution enables formation of formic acid and methyl formate in close to 100percent combined selectivity, thus with only negligible sugar oxidation to CO2. In detail, we report oxidation of a methanolic glucose solution using H8[PV5Mo7O40] (HPA-5) as catalyst at 90 °C and 20 bar O2 pressure. Experiments with 13C-labelled glucose confirm unambiguously that glucose is the only source of the observed formic acid and methyl formate formation under the applied oxidation conditions. Our results demonstrate a very astonishing solvent effect for the POM-catalysed glucose oxidation. In comparison to earlier work, a step-change in product yield and selectivity is achieved by applying an alcoholic reaction medium. The extremely high combined yields of formic acid and methyl formate greatly facilitate product isolation as low-boiling methyl formate (bp = 32 °C) can simply be isolated from the reaction mixture by distillation.

Study of the atmospheric chemistry of 2-formylcinnamaldehyde

2-Formylcinnamaldehyde is a significant product of the reaction of naphthalene with OH radicals, and its photolysis and gas-phase reactions with O3, NO3 radicals, and OH radicals have been investigated in this work. 2-Formylcinnamaldehyde was observed to undergo photolysis by black lamps, with a photolysis rate of 0.14 × J(NO2), where J(NO2) is the NO2 photolysis rate. The measured rate constants for the reactions of 2-formylcinnamaldehyde with O3, NO3 radicals, and OH radicals (in units of cm3 molecule-1 s-1) were 1.8 × 10-18, 4.3 × 10-14, and 2.1 × 10-11, respectively, with those for the O3 and NO3 reactions being for the E-isomer. 2-Formylcinnamaldehyde was observed to undergo significant adsorption and desorption from the reaction chamber Teflon film walls, and the photolysis rate and rate constants are subject to significant uncertainties. In the atmosphere, the dominant chemical loss processes for 2-formylcinnamaldehyde will be photolysis during daylight hours and reaction with NO3 radicals during nighttime. Phthaldialdehyde and glyoxal were observed as products of the OH radical and O3 reactions, and photolysis of E-2- formylcinnamaldehyde led to formation of Z-2-formylcinnamaldehyde plus two other molecular weight 160 isomers. The present results are compared with previous literature data, and reaction mechanisms are discussed.

Aqueous Photochemistry of Glyoxylic Acid

Aerosols affect climate change, the energy balance of the atmosphere, and public health due to their variable chemical composition, size, and shape. While the formation of secondary organic aerosols (SOA) from gas phase precursors is relatively well understood, studying aqueous chemical reactions contributing to the total SOA budget is the current focus of major attention. Field measurements have revealed that mono-, di-, and oxo-carboxylic acids are abundant species present in SOA and atmospheric waters. This work explores the fate of one of these 2-oxocarboxylic acids, glyoxylic acid, which can photogenerate reactive species under solar irradiation. Additionally, the dark thermal aging of photoproducts is studied by UV-visible and fluorescence spectroscopies to reveal that the optical properties are altered by the glyoxal produced. The optical properties display periodicity in the time domain of the UV-visible spectrum of chromophores with absorption enhancement (thermochromism) or loss (photobleaching) during nighttime and daytime cycles, respectively. During irradiation, excited state glyoxylic acid can undergo α-cleavage or participate in hydrogen abstractions. The use of 13C nuclear magnetic resonance spectroscopy (NMR) analysis shows that glyoxal is an important intermediate produced during direct photolysis. Glyoxal quickly reaches a quasi-steady state as confirmed by UHPLC-MS analysis of its corresponding (E) and (Z) 2,4-dinitrophenylhydrazones. The homolytic cleavage of glyoxylic acid is proposed as a fundamental step for the production of glyoxal. Both carbon oxides, CO2(g) and CO(g) evolving to the gas-phase, are quantified by FTIR spectroscopy. Finally, formic acid, oxalic acid, and tartaric acid photoproducts are identified by ion chromatography (IC) with conductivity and electrospray (ESI) mass spectrometry (MS) detection and 1H NMR spectroscopy. A reaction mechanism is proposed based on all experimental observations.

Formation of glyoxal by oxidative dehydrogenation of ethylene glycol

Iron(III) phosphates doped with a very small amount of molybdenum(VI) were found to be effective as catalysts for a vapor-phase oxidative dehydrogenation of ethylene glycol to glyoxal. The effects of the molybdenum(VI) content and of the reaction variable

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Characterization of precursors and elucidation of the reaction pathway leading to a novel coloured 2H,7H,8aH-pyrano[2,3-b]pyran-3-one from pentoses by quantitative studies and application of 13C-labelling experiments

The intensely coloured (1R,8aR)- and (1S,8aR)-4-(2-furyl)-7-[(2-furyl)methylidene]-2-hydroxy-2H,7H,8aH-pyrano[2,3-b]pyran-3-one (1a/1b) have recently been identified among the main coloured compounds formed in the presence of pentoses. To clarify its formation pathway, quantitative studies on the effectivity of certain carbohydrate degradation products as precursors of 1a/1b were performed indicating the 3-deoxypentose-2-ulose, furan-2-carboxaldehyde and hydroxyacetaldehyde as the penultimate precursors of the colourant. In addition, a labelling experiment with [13C1]-xylose was performed to elucidate how these precursors are transformed into 1a/1b. Copyright (C) 1998 Elsevier Science Ltd.

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Mechanism and Product Distribution of the O3-Initiated Degradation of (E)-2-Heptenal, (E)-2-Octenal, and (E)-2-Nonenal

The O3-molecule initiated degradation of three 2-alkenals (E)-2-heptenal, (E)-2-octenal, and (E)-2-nonenal has been investigated in a 1080 L quartz-glass environmental chamber at 298 ± 2 K and atmospheric pressure of synthetic air using in situ FTIR spectroscopy to monitor the reactants and products. The experiments were performed in the absence of an OH scavenger. The molar yields of the primary products formed were glyoxal (49 ± 4) % and pentanal (34 ± 3) % from the reaction of (E)-2-heptenal with O3, glyoxal (41 ± 3) % and hexanal (39 ± 3) % from the reaction of (E)-2-octenal with O3, and glyoxal (45 ± 3) % and heptanal (46 ± 3) % from the reaction of (E)-2-nonenal with O3. The residual bands in the infrared product spectra for each of the studied reactions are attributed to 2-oxoaldehyde compounds. Based on the observed products, a general mechanism for the ozonolysis reaction of long chain unsaturated aldehydes is proposed, and the results are compared with the available literature data.

Photocatalysis by illuminated titania: Oxidation of hydroquinone and p-benzoquinone

Photocatalytic oxidation of hydroquinonc and p-benzoquinone, the main intermediates which are formed in the process of phenol oxidation on irradiated titania, was studied. The reaction proceeds via several steps. Some of the intermediates were detected by HPLC and GC-MS: ethanedial, glycerol, and 1,2,4-trihydroxybenzene. Under illumination in the presence of TiO2, p-benzoquinone initially transforms partly to hydroquinone, partly oxidizes to unidentified intermediates. The residue, about 4% of the concentration of hydroquinone, undergoes slow oxidation together with the hydroquinone. The rate of hydroquinone photooxidation shows 1st order behaviour.

Gas-phase reaction of ozone with trans-2-hexenal, trans-2-hexenyl acetate, ethylvinyl ketone, and 6-methyl-5-hepten-2-one

The gas-phase reaction of ozone with the unsaturated oxygenates trans-2-hexenal, trans-2-hexenyl acetate, ethylvinyl ketone, and 6-methyl-5-hepten-2-one, which are components of biogenic emissions and/or close structural homologues thereof, has been investigated at atmospheric pressure and ambient temperature (286-291 K) and humidity (RH = 55 ± 10%). Reaction rate constants, in units of 10-18 cm3 molecule-1 s-1, are 1.28 ± 0.28 for trans2-hexenal, 21.8 ± 2.8 for trans-2-hexenyl acetate, and 394 ± 40 for 6-methyl-5-hepten-2-one. Carbonyl product formation yields, measured with sufficient cyclohexane added to scavenge the hydroxyl radical, are 0.53 ± 0.06 for n-butanal and 0.56 ± 0.04 for glyoxal from trans-2-hexenal, 0.47 ± 0.02 for n-butanal and 0.58 ± 0.14 for 1-oxoethyl acetate from trans-2-hexenyl acetate, 0.55 ± 0.07 for formaldehyde and 0.44 ± 0.03 for 2-oxobutanal from ethylvinyl ketone, and 0.28 ± 0.02 for acetone from 6-methyl-5-hepten-2-one. Reaction mechanisms are outlined and the atmospheric persistence of the compounds studied is briefly discussed.

Pillared H-MCM-36 mesoporous and H-MCM-22 microporous materials for conversion of levoglucosan: Influence of varying acidity

Catalytic transformation of levoglucosan (1-6-anhdyro-β-d- glucopyranose) was carried out in a fixed bed reactor at 573 K over H-MCM-22 and pillared H-MCM-36 with different acidities. The yield of the products, phases and product distribution was influenced mainly by the acidity of the zeolite catalysts. Oxygenated species were the main liquid product, consisting foremost of aldehydes and furfural. The formation of the liquid products was higher over MCM-36 pillared materials than over MCM-22 for all the oxygenated species except acetone. The deactivation due to coking was less severe over the pillared materials compared to the microporous precursor. However, it was possible to successfully regenerate the spent zeolites without changing the structure.

PROCESSES FOR PREPARING C-4 SUGARS AND KETOSE SUGARS

Various processes for preparing C4 aldoses and/or ketones thereof are described. Various processes are described for preparing C4 aldoses and/or ketones thereof from feed compositions comprising glycolaldehyde. Also, various processes for preparing useful downstream products and intermediates, such as erythritol and erythronic acid, from the C4 aldoses and/or ketones thereof are described.

Simultaneous generation of acrylamide, β-carboline heterocyclic amines and advanced glycation ends products in an aqueous Maillard reaction model system

The simultaneous formation of acrylamide; β-carboline heterocyclic amines (HAs): harmane and norharmane; and advanced glycation end products (AGEs) (Nε-(carboxymethyl)lysine (CML) and Nε-(carboxyethyl)lysine (CEL)) was analyzed based on an aqueous model system. The model systems included lysine–glucose (Lys/Glu), asparagine–glucose (Asn/Glu), tryptophan–glucose (Trp/Glu), and a mixture of these amino acids (Mix/Glu). Only AGEs were generated when heated at 100 °C, Asn and Trp competed with Lys for glucose and methylglyoxal (MGO), and glyoxal (GO) decreased AGE content. The k value of CML, CEL, and acrylamide decreased when heated at 130 °C, whereas that of harmane increased in the Mix/Glu, owing to the competition between Lys and Asn for glucose, GO, and MGO. Harmane preferably formed via the Pictet–Spengler condensation between Trp and acetaldehyde, which further reduced acrylamide formation via the acrolein pathway.