Fact-checked by Grok 2 weeks ago

Glyoxal

Glyoxal, chemically known as ethanedial, is the simplest aliphatic dialdehyde with the molecular formula C₂H₂O₂ and the structure OHC–CHO.^[1] It appears as a pale yellow, hygroscopic liquid or crystalline solid, with a melting point of 15 °C, a boiling point of 51 °C, and high solubility in water, alcohols, and ethers; commercially, it is most often supplied as a 40% aqueous solution to prevent polymerization and dimerization.^[1] This reactive compound plays a dual role as an industrial chemical and a biological metabolite, distinguished by its bifunctional aldehyde groups that enable cross-linking and condensation reactions.^[2] Industrially, glyoxal is produced primarily through the gas-phase catalytic oxidation of ethylene glycol using silver or copper catalysts at elevated temperatures, yielding high-purity product in an integrated process from ethylene.^[1] Alternative methods include the nitric acid oxidation of acetaldehyde, though the ethylene glycol route dominates due to efficiency and scalability.^[1] Its applications are diverse: as a cross-linking agent, it insolubilizes starches and celluloses in paper coatings, textile finishes, and leather tanning to enhance durability and wrinkle resistance; it also serves as an intermediate in synthesizing pharmaceuticals, resins, dyes, and biocides.^[2] In the oil and gas sector, glyoxal functions as a corrosion inhibitor and scale control agent in water treatment.^[1] In biochemistry, glyoxal arises endogenously from lipid peroxidation, glycolysis, and the degradation of glucose or ascorbic acid, acting as a potent glycating agent that forms advanced glycation end-products (AGEs) through non-enzymatic reactions with proteins, lipids, and nucleic acids.^[3] These AGEs contribute to oxidative stress, inflammation, and tissue damage in conditions such as diabetes, aging, and chronic kidney disease, with glyoxal-derived cross-links implicated in vascular complications and protein dysfunction.^[4] Despite its toxicity as a skin and respiratory irritant, glyoxal's biodegradability (over 90% under OECD guidelines) supports its environmental profile in controlled applications.^[5]

Production

Industrial production

Glyoxal was first prepared in 1856 by the German-British chemist Heinrich Debus through the oxidation of ethanol with nitric acid.^[6] The primary industrial route for glyoxal production is the gas-phase oxidation of ethylene glycol, known as the Laporte process, which involves air oxidation at temperatures of 200–300°C in the presence of catalysts such as silver or copper.^[7]^[8] This catalytic dehydrogenation yields glyoxal according to the reaction:

\ce{HOCH2CH2OH + O2 -> OCHCHO + 2 H2O}

An alternative method is the liquid-phase oxidation of acetaldehyde using nitric acid.^[6] Global production capacity for glyoxal is concentrated among a few major producers, with BASF operating the largest facility in Ludwigshafen, Germany, at approximately 60,000 tons per year; additional sites are located in the United States and China. Global production is estimated at around 430,000 tons annually as of 2025, with major producers including BASF, WeylChem, and Chinese firms like Haihang Industry.^[9] Following synthesis, glyoxal is purified by distillation under reduced pressure to produce stable 40% aqueous solutions, as the pure compound readily undergoes polymerization to form a solid hydrate.^[10]

Laboratory synthesis

Glyoxal can be synthesized in the laboratory through the oxidation of acetaldehyde using selenious acid (H₂SeO₃) as the oxidant. In a typical procedure, paraldehyde (the cyclic trimer of acetaldehyde) is reacted with selenious acid in a mixture of dioxane and acetic acid at 65–80°C for several hours, followed by steam distillation, treatment with lead acetate to remove selenium, and purification via the bisulfite adduct to yield glyoxal bisulfite in 72–74% yield based on selenious acid.^[11] The overall transformation can be represented by the catalyzed aerobic oxidation equation:

$2 \ce{CH3CHO} + \ce{O2} \rightarrow 2 \ce{OCHCHO} + 2 \ce{H2O}

This method provides a feasible route for small-scale preparation, though it requires careful handling due to the toxicity of selenium compounds.^[12] Another laboratory route involves the ozonolysis of benzene, which cleaves the aromatic ring to form glyoxal upon reductive workup. Benzene is dissolved in a solvent such as acetic acid or a mixture with nitromethane and ozonized at low temperatures (-5°C to 40°C), followed by reduction with dimethyl sulfide or acidified iodide ions, affording glyoxal in yields of 50–75% based on ozone absorption.^[13] This approach is particularly useful for obtaining glyoxal without selenium-based reagents.^[14] Anhydrous glyoxal, which is monomeric and volatile, is prepared by dehydrating the commercial glyoxal dihydrate (or trimer dihydrate) through heating with phosphorus pentoxide (P₄O₁₀) at approximately 150°C under vacuum, followed by condensation of the vapors in a cold trap. This distillation removes water and prevents polymerization, yielding pure anhydrous glyoxal as a yellow liquid.^[15] Due to glyoxal's strong tendency to oligomerize, especially in the presence of moisture or at elevated temperatures, laboratory syntheses are conducted under inert atmospheres (e.g., nitrogen) and at low temperatures to maintain the monomeric form and ensure high purity.^[16] These conditions minimize side reactions and facilitate handling of the reactive dialdehyde.

Properties

Physical properties

Glyoxal has the molecular formula C₂H₂O₂, corresponding to the structural formula OHCCHO, and a molar mass of 58.036 g/mol.^[1] In its solid state, glyoxal forms white crystals below 15 °C, transitioning to a light yellow liquid at room temperature due to its low melting point. The vapor phase exhibits a distinctive green color. It possesses a weak, sour odor characteristic of many aldehydes.^[1] The melting point of glyoxal is 15 °C, while its boiling point is 51 °C, at which point it undergoes decomposition rather than stable vaporization. Commercially, glyoxal is typically supplied as a 40% aqueous solution, which has a density of 1.27 g/mL at 20 °C and boils at approximately 104 °C.^[1]^[17] Glyoxal demonstrates high solubility in water, enabling the preparation of stable 40% solutions for industrial use, and it is fully miscible with alcohols and ethers, reflecting its polar nature.^[1] The volatility of glyoxal in aqueous environments is quantified by its temperature-dependent Henry's law constant, given by

K_H = 4.19 \times 10^5 \times \exp\left[\frac{6.22 \times 10^4}{R} \times \left(\frac{1}{T} - \frac{1}{298}\right)\right] \ \mathrm{M \cdot atm^{-1}},

where R is the gas constant and T is the temperature in Kelvin; this indicates moderate partitioning into the gas phase under ambient conditions.^[18]

Chemical properties

Glyoxal (CHOCHO) is the simplest dialdehyde, consisting of two formyl groups attached to adjacent carbon atoms in a planar trans configuration, which is the thermodynamically favored isomer due to minimal steric hindrance between the carbonyl groups.^[1]^[19] This planarity facilitates conjugation between the two carbonyl moieties, influencing its spectroscopic properties; the C=O stretching vibrations appear as strong bands near 1700 cm⁻¹ in the infrared spectrum, characteristic of unconjugated aldehydes but slightly shifted due to the vicinal arrangement.^[20] The carbonyl groups in glyoxal are highly electrophilic, rendering the molecule prone to nucleophilic addition reactions typical of aldehydes. It undergoes aldol condensations with enolizable carbonyl compounds, forming β-hydroxy aldehydes or α,β-unsaturated carbonyls under basic or acidic conditions.^[1] Additionally, glyoxal readily forms acetals with alcohols in the presence of acid catalysts, protecting the aldehyde functions, and reacts with primary amines to yield imines (Schiff bases) or, in excess amine, cyclic heterocycles such as imidazoles via double condensation.^[1] These reactions highlight its utility in synthetic chemistry, where the dual functionality allows for bis-functionalization products. In the absence of stabilizers, glyoxal exhibits a strong tendency to self-condense, particularly in anhydrous conditions, leading to the formation of cyclic dimers (e.g., dioxolane structures) and higher oligomers through acetal-like linkages between carbonyls.^[1] This polymerization occurs rapidly even at low temperatures without water, resulting in yellow, viscous products that complicate handling of the pure compound.^[21] Glyoxal can also be oxidized at one or both carbonyls to glyoxylic acid (CHOCOOH) using mild oxidants like dilute nitric acid, or fully to oxalic acid under stronger conditions; conversely, catalytic hydrogenation or electrochemical reduction converts it to ethylene glycol (HOCH₂CH₂OH).^[1]^[22] A representative example of its reactivity is the acid-catalyzed condensation with urea, which produces glyoxal-urea polymers used in resins:

\text{OCHCHO} + 2 \text{CO(NH}_2\text{)}_2 \rightarrow \text{cyclic urea-glyoxal resin}

This reaction proceeds via initial imine formation followed by cyclization and cross-linking, yielding water-soluble adhesives with low formaldehyde content.^[23]

Speciation in aqueous solution

Glyoxal is commercially supplied as a 40% aqueous solution containing hydrated oligomers, which is stabilized—typically with mineral acids or polyhydroxy polymers such as starch or polyvinyl alcohol—to inhibit polymerization during storage and handling.^[24]^[8] In aqueous media, glyoxal exists in a dynamic equilibrium involving multiple species: the free monomeric dialdehyde (OHCCHO), the dihydrate (gem-diol, (HO)_2CHCH(OH)_2), and cyclic oligomers including dimers (such as 2-(dihydroxymethyl)-1,3-dioxolane-4,5-diol) and trimers (such as bis(1,3-dioxolane) structures).^[24] These forms arise from reversible hydration of the aldehyde groups and subsequent cyclization reactions between hydrated molecules.^[25] The primary hydration reaction is represented by the equilibrium

\ce{OHCCHO + 2 H2O ⇌ (HO)2CHCH(OH)2}

with both stepwise hydration constants being large (K_hyd1 ≈ 6 × 10³ M^-1 and K_hyd2 ≈ 40 M^-1 at 298 K), strongly favoring the dihydrate over the free aldehyde.^[26] This equilibrium is essentially pH-independent in neutral to acidic conditions but shifts toward the free form with increasing temperature, as the endothermic dehydration becomes more favorable. Speciation depends markedly on concentration: below 1 M, the solution is dominated by the monomeric species and their hydrates, with minimal oligomerization; above 1 M, dimers and higher oligomers prevail due to intermolecular cyclization, as indicated by an oligomerization equilibrium constant on the order of 10³ M^-1.^[27] In the commercial 40% solution (approximately 8.8 M), oligomers constitute a significant fraction, contributing to its stability and viscosity.^[24] Nuclear magnetic resonance (NMR) spectroscopy provides key insights into this speciation, showing distinct ¹H and ¹³C chemical shifts for the free aldehyde versus hydrated forms. At room temperature (25 °C), UV-visible spectroscopy confirms that less than 0.02% of glyoxal remains as the free dialdehyde, with roughly 98% distributed between monohydrate and dihydrate forms in dilute solutions, underscoring the near-complete hydration under ambient conditions.^[28]

Biological and environmental roles

Biochemical reactivity

Glyoxal is generated endogenously through multiple pathways, including lipid peroxidation during oxidative stress, degradation of glycolytic intermediates, and breakdown of glycated proteins.^[29] It arises from the non-enzymatic oxidation of lipids, where reactive oxygen species cleave polyunsaturated fatty acids to form α-oxoaldehydes like glyoxal.^[30] In glycolysis, glyoxal forms as a byproduct from the degradation of intermediates such as dihydroxyacetone phosphate and glyceraldehyde-3-phosphate, often linked to the metabolism of methylglyoxal.^[29] Additionally, protein oxidation, particularly involving serine residues, contributes to its production via oxidative cleavage.^[30] In biological systems, glyoxal exhibits high reactivity as a dicarbonyl compound, primarily engaging in non-enzymatic glycation reactions with nucleophilic amino acid residues in proteins, leading to the formation of advanced glycation end-products (AGEs). It preferentially modifies arginine residues to produce imidazolone derivatives, such as glyoxal-hydroimidazolone (G-H1), through a condensation reaction that releases water. This process can be represented as:

\text{OCHCHO} + \text{[Arg](/page/ARG)} \rightarrow \text{imidazolone derivative} + \text{H}_2\text{O}

^[31] Glyoxal also reacts with lysine residues to form Nε-(carboxymethyl)lysine (CML), a stable AGE marker, and with cysteine thiols to generate thioether adducts or disulfide-linked modifications, all of which alter protein structure and function.^[32]^[33] These glycation events contribute to protein misfolding, impaired enzymatic activity, and cellular dysfunction by promoting cross-linking and aggregation.^[29] Glyoxal induces DNA damage by glycating nucleobases, particularly guanine, to form cyclic adducts like glyoxal-guanine (gG), which distort the DNA helix and impede replication and transcription.^[34] These lesions arise from the nucleophilic attack of the guanine exocyclic amino group on one carbonyl of glyoxal, followed by cyclization. Repair of such glyoxal-derived DNA adducts has been proposed to be mediated by the DJ-1 protein (also known as Park7), reported as a deglycase that hydrolyzes the modified base, though recent studies suggest its role may be more indirect through detoxification of precursors, preventing mutagenesis and genomic instability.^[35]^[36] The biochemical reactivity of glyoxal has significant health implications, particularly in oxidative stress-related pathologies. Elevated glyoxal levels exacerbate diabetic complications, such as nephropathy, by accelerating AGE formation in renal tissues, leading to glomerular damage and fibrosis.^[37] In Alzheimer's disease, glyoxal promotes the aggregation of β-amyloid peptides and tau proteins through glycation, contributing to neurofibrillary tangles and plaque formation.^[38] Furthermore, glyoxal-driven oxidative stress and AGE accumulation are linked to cellular senescence and aging, as it induces reactive oxygen species production and mitochondrial dysfunction in various cell types.^[39]

Natural occurrences

Glyoxal serves as an endogenous metabolite in biological systems, primarily formed through the auto-oxidation of glucose and lipid peroxidation processes.^[40] Its production is notably elevated in conditions such as diabetes, where oxidative stress enhances its synthesis from these metabolic pathways.^[41] In the atmosphere, glyoxal exists as a trace gas, originating from primary sources like biomass burning and vehicle emissions, as well as secondary formation via the oxidation of volatile organic compounds such as isoprene and acetylene.^[42]^[43]^[44] Tropospheric concentrations typically range from 0 to 200 parts per trillion (ppt) in remote areas, rising to up to 1 parts per billion (ppb) in urban and polluted environments due to intensified emissions and photochemical activity.^[44] Beyond Earth, glyoxal has been identified in simulations of interstellar ice chemistry and as a potential component in cometary materials, though direct detections remain tentative.^[45]^[46] On Earth, it also forms as a byproduct of the Maillard reaction during the cooking of carbohydrate- and fat-rich foods.^[47] Global mapping of atmospheric glyoxal relies on satellite remote sensing techniques, such as those employing the Ozone Monitoring Instrument (OMI) aboard the Aura satellite and the TROPOspheric Monitoring Instrument (TROPOMI) aboard Sentinel-5 Precursor, which enable detection of column densities and identification of emission hotspots.^[48] Glyoxal exhibits a short atmospheric lifetime of approximately 2–3 hours, primarily due to rapid removal via photolysis and reactions with hydroxyl (OH) radicals.^[49]

Applications

In materials and textiles

Glyoxal functions as a versatile cross-linking agent in the paper industry, where it reacts with starch or casein in surface coatings to enhance the mechanical strength, wet resistance, and printability of paper and board products. By forming stable bonds with hydroxyl groups in these biopolymers, glyoxal improves the cohesion and durability of coatings, making it particularly valuable for specialty papers used in packaging and printing applications.^[50]^[51]^[52] In the textile sector, glyoxal condenses with urea and formaldehyde to produce resins like N,N'-dimethylol-4,5-dihydroxyethyleneurea (DMDHEU), which are applied as permanent press finishes to impart wrinkle resistance and dimensional stability to cellulosic fabrics such as cotton. These finishes cross-link cellulose fibers, enabling smooth-drying properties and durability through repeated laundering, with DMDHEU accounting for approximately 90% of easy-care treatments due to its effectiveness and stability. Eco-friendly variants leverage glyoxal to minimize formaldehyde emissions, offering lower-toxicity alternatives that align with regulatory demands for reduced volatile organic compounds in apparel production.^[53]^[54] Glyoxal also plays a key role in polymer applications, serving as a solubilizer for resins and a cross-linker for polyvinyl alcohol (PVA) in the formulation of adhesives and films. In PVA-based systems, glyoxal reacts with hydroxyl groups to create networked structures, boosting tensile strength, thermal stability, and water resistance, which are essential for wood adhesives, barrier coatings, and flexible films used in packaging.^[55]^[56] Typically applied as a 40% aqueous solution, glyoxal is incorporated into formulations via padding or coating methods and then cured at 100–150°C to promote the formation of cyclic acetal linkages, which provide the durable cross-linked network without requiring harsh conditions. This process ensures efficient bonding while maintaining material integrity. It is also used in leather tanning to enhance durability.^[57]^[58]^[55]^[1] The demand for glyoxal in materials and textiles significantly drives market growth, particularly in sustainable packaging and apparel sectors, where its role in eco-friendly cross-linking supports biodegradable alternatives and aligns with global shifts toward green chemistry, projecting a compound annual growth rate of 4.4% through 2035.^[59]^[60]

In organic synthesis

Glyoxal serves as a versatile building block in organic synthesis, particularly for constructing heterocyclic compounds through condensation reactions with amines and amides. It is a key precursor in the synthesis of imidazoles, pyrazines, and pyrroles, enabling the formation of these rings via multi-component reactions. For instance, the Debus-Radziszewski imidazole synthesis involves the condensation of glyoxal with ammonia and a carbonyl compound, such as an aldehyde or ketone, to yield substituted imidazoles. This reaction proceeds under mild conditions, typically in aqueous or alcoholic media, and is widely employed for preparing biologically active heterocycles. The general equation for imidazole formation is:

\ce{OHCCHO + 2 NH3 + RCOCH3 -> imidazole derivative}

where R represents an alkyl or aryl substituent.^[61] In pyrazine synthesis, glyoxal reacts with 1,2-diamines, such as o-phenylenediamine, to form quinoxalines, which are fused pyrazine systems, often in the presence of a bisulfite adduct to enhance yields. This approach is valuable for accessing pyrazine derivatives used in agrochemicals and pharmaceuticals. Similarly, glyoxal participates in pyrrole synthesis through copper-catalyzed annulation reactions with secondary amines and other components, generating N,O-hemiacetal intermediates that cyclize to substituted pyrroles. These methods highlight glyoxal's utility in assembling nitrogen-containing heterocycles central to medicinal chemistry.^[62]^[63] Glyoxal-derived imidazoles are important intermediates in pharmaceutical synthesis, particularly for antihistamines and antifungals. The imidazole moiety is incorporated into drugs like cimetidine, an H2-receptor antagonist used as an antihistamine for treating acid-related disorders, and miconazole, an antifungal agent targeting ergosterol biosynthesis in fungi. These applications leverage the heterocycle's ability to mimic natural ligands and interact with biological targets. Although direct synthesis of alloxan (a diabetogenic agent used in research) from glyoxal and urea is not standard, related condensations of glyoxal with ureas produce imidazoimidazole derivatives that serve as precursors to pyrimidine-based pharmaceuticals.^[64] In the production of dyes and pigments, glyoxal functions as a chemical intermediate.^[1] Beyond small-molecule synthesis, glyoxal is employed in histology as a fixative for electron microscopy, where it cross-links proteins via its aldehyde groups without causing significant distortion or masking of antigens. This property allows superior preservation of ultrastructure and enhances immunoreactivity compared to formaldehyde, making it ideal for high-resolution imaging and immunohistochemical studies. A 3% glyoxal solution in acetate buffer penetrates tissues rapidly and maintains cellular morphology effectively.^[65]^[66]

In other industrial applications

Glyoxal is used as a corrosion inhibitor and scale control agent in water treatment for the oil and gas sector.^[1]

Safety and toxicology

Health hazards

Glyoxal exhibits moderate acute toxicity upon ingestion, with an oral LD50 in rats ranging from 2.2 to 5 g/kg, indicating relatively low immediate lethality compared to more potent toxins.^[67] Dermal absorption is limited, as evidenced by a rabbit dermal LD50 exceeding 10 g/kg, though the compound remains an irritant to skin, causing moderate redness and inflammation upon contact.^[68] It also irritates the eyes, leading to redness, pain, and potential corneal damage, and the respiratory tract, where vapors or aerosols provoke coughing, throat irritation, and nasal discomfort.^[68] In terms of genotoxicity, glyoxal is directly mutagenic in vitro, forming DNA adducts such as imidazopurinones and inducing chromosomal aberrations in bacterial and mammalian cell lines without requiring metabolic activation.^[24] Chronic exposure to glyoxal can lead to skin sensitization, manifesting as allergic contact dermatitis characterized by eczematous reactions upon re-exposure, particularly in occupational settings like healthcare.^[67] As a precursor to advanced glycation end products (AGEs), it promotes protein glycation, which may contribute to carcinogenic potential by fostering chronic inflammation and cellular proliferation, though long-term animal studies show no direct carcinogenicity.^[69] In diabetes, elevated glyoxal levels drive glycation of extracellular matrix proteins, resulting in vascular endothelial damage, fibrosis, and impaired wound healing.^[70] The Cosmetic Ingredient Review (CIR) Expert Panel, in its 2017 assessment, concluded that glyoxal is safe for use in nail products at concentrations up to 1.25%, citing moderate oral toxicity and insufficient data for broader cosmetic applications.^[67] Inhalation poses risks of lung irritation from vapors, with the American Conference of Governmental Industrial Hygienists (ACGIH) establishing a threshold limit value (TLV) of 0.1 mg/m³ as a time-weighted average to prevent respiratory sensitization.^[68]

Handling and regulations

Glyoxal, particularly in its common 40% aqueous solution form, requires careful storage to maintain stability and prevent unwanted reactions. It should be kept in a cool environment below 25°C in tightly closed containers to avoid polymerization, which can be triggered by heat or exposure to strong acids and bases. High-density polyethylene (HDPE) containers are recommended for storage due to their compatibility with the solution.^[58]^[71]^[1] Safe handling of glyoxal involves the use of personal protective equipment (PPE), including chemical-resistant gloves, safety goggles, and protective clothing, to prevent skin and eye contact. Work areas must be well-ventilated to minimize inhalation of vapors, which can cause respiratory irritation. In the event of spills, the area should be ventilated, non-sparking tools used for cleanup, and the material absorbed with inert substances; neutralization with sodium bisulfite can be employed for small spills to form a less hazardous adduct before disposal.^[72]^[73]^[74] The 40% aqueous solution of glyoxal presents a low fire hazard, with a flash point exceeding 100°C, rendering it non-flammable under standard conditions. If involved in a fire, it may release toxic fumes including carbon oxides; appropriate extinguishing media include water spray, carbon dioxide, dry chemical, or alcohol-resistant foam, while avoiding direct water streams on large spills to prevent runoff.^[75]^[76]^[77] Glyoxal is regulated under various frameworks due to its sensitizing and potential genotoxic properties. In the European Union, it is classified as a skin sensitizer (Skin Sens. 1, H317: May cause an allergic skin reaction) under the CLP Regulation, and it is registered under REACH with restrictions under the Cosmetics Regulation limiting its use in cosmetics to a maximum concentration of 0.01% (100 ppm) in finished products. In the United States, glyoxal is listed on the EPA's Toxic Substances Control Act (TSCA) inventory, requiring reporting for certain manufacturing and import activities. The International Agency for Research on Cancer (IARC) has not classified glyoxal as a carcinogen, though it is monitored for in vitro genotoxicity, with evidence of mutagenic potential in category 3 under EU guidelines.^[78]^[1] Environmentally, glyoxal is readily biodegradable but exhibits moderate toxicity to aquatic life, with an LC50 for fish (e.g., Leuciscus idus) in the range of 65–272 mg/L over 96 hours. It should be disposed of as hazardous waste in accordance with local regulations to prevent release into waterways.^[79]^[80]^[81]

References

[1]
Glyoxal | OHCCHO | CID 7860 - PubChem - NIH
Glyoxal is the dialdehyde that is the smallest possible and which consists of ethane having oxo groups on both carbons.
[2]
Glyoxal | 107-22-2 - ChemicalBook
Aug 21, 2025 · Glyoxal (CAS 107-22-2) information, including chemical properties, structure, melting point, boiling point, density, formula, molecular ...
[3]
Investigating the Glycating Effects of Glucose, Glyoxal and ... - Nature
Jun 13, 2018 · Glycation is the non-enzymatic reaction between reducing sugars, such as glucose, and proteins, lipids or nucleic acids, producing Advanced ...
[4]
Formation of glyoxal, methylglyoxal and 3-deoxyglucosone in the ...
Early glycation is thought to involve the reaction of glucose with N-terminal and lysyl side chain amino groups to form Schiff's base and fructosamine adducts.
[5]
[PDF] BASF Glyoxal Brochure
Glyoxal is readily biodegradable by showing more than 90% decrease of dissolved organic carbon according to. OECD guidelines 301 C-E and 303 A. Accreditation ...
[6]
Oxidation of acetaldehyde to glyoxal by nitric acid
The liquid phase oxidation of acetaldehyde or paraldehyde by aqueous nitric acid to glyoxal was investigated in a stainless steel autoclave maintained under ...
[7]
Subpart YY - Caprolactam, Glyoxal, and Glyoxylic Acid Production
Aug 6, 2025 · This source category applies to any facility that produces caprolactam (C 6 H 11 NO), glyoxal (C 2 H 2 O 2 ), or glyoxylic acid (C 2 H 2 O 3 ).
[8]
glyoxal production - Europe - ecoQuery - Ecoinvent
The gas-phase oxidation of ethylene glycol by atmospheric oxygen in the presence of dehydrogenation catalysts (metallic copper or silver) represents the basis ...
[9]
Glyoxal Market Size, Growth Report, Forecast 2025–2030
Jul 23, 2025 · The glyoxal market is moderately concentrated. BASF leverages 60,000 tons of captive capacity in Germany and a new Zhanjiang line to ...<|separator|>
[10]
Glyoxal Market Size, Share & Growth Report 2032 - SNS Insider
In the U.S., glyoxal is primarily used in textiles, oil & gas, paper, and personal care for applications including crosslinking, intermediate synthesis, and as ...<|control11|><|separator|>
[11]
US2463030A - Process of purifying glyoxal - Google Patents
Water may be distilled from such solutions under reduced pressure, and if the distillation is carried to dryness, a solid polymeric glyoxai hydrate remains.
[12]
glyoxal bisulfite - Organic Syntheses Procedure
The most feasible are the oxidation of acetaldehyde by nitric,, or selenious acid; the hydrolysis of dichlorodioxane; and the hydrolysis of the product ...
[13]
https://patents.google.com/patent/US3637860A/en
[14]
US3637860A - Process of preparing glyoxal - Google Patents
The reaction of benzene with ozonized oxygen has long been recognized as leading to the formation of glyoxal. Although several studies have been reported on the ...
[15]
Glyoxal from Ozonolysis of Benzene - ACS Publications
This article is cited by 6 publications. Tong Pan, Pingfan Li. Sulfur-Mediated Formal Allylic C–H Cyclopropanation of α-Methylstyrenes.
[16]
[PDF] Secondary Organic Aerosol-Forming Reactions of Glyoxal with ...
Mar 12, 2009 · Gas-phase glyoxal was generated by heating equal masses of glyoxal trimer dihydrate and phosphorus pentoxide to 150 °C and trapping the yellow- ...Missing: paper | Show results with:paper
[17]
Glyoxal - Sciencemadness Wiki
Sep 27, 2020 · Glyoxal can be prepared by careful oxidation of ethanol with nitric acid. Another lab route involves oxidation of acetaldehyde with selenous ...Missing: methods | Show results with:methods
[18]
GLYOXAL - CAMEO Chemicals - NOAA
Physical Properties ; Specific Gravity: 1.29 at 68°F (liquid,40% solution) (USCG, 1999) - Denser than water; will sink ; Boiling Point: 124°F at 776 mmHg (NTP, ...
[19]
Effective Henry's law constants of glyoxal, glyoxylic acid, and ...
Jan 6, 2009 · The experimentally determined Henry's law constants are: glyoxal, KH = 4.19 × 105 × exp[(62.2 × 103/R) × (1/T − 1/298)]; glycolic acid, KH = ...Abstract · Introduction · Experimental Section · Results and Discussion
[20]
A theoretical study of the structure of glyoxal - ScienceDirect
Cited by (16) The high-energy conformers are found to be planar for both molecules in agreement with previous calculations. The empirical scale factors ...
[21]
Raman and infrared spectra of solid glyoxal‐d1 and glyoxal‐d2 - Cole
Fundamental frequencies of glyoxal-d2 were observed at 2169, 1709, 1131, 944, 908 and 543 cm−1 and assigned as the CD stretching, CO stretching, CD rocking, ...
[22]
GLYOXAL - Ataman Kimya
Glyoxal was first prepared and named by the German-British chemist Heinrich Debus (1824–1915) by reacting ethanol with nitric acid.
[23]
Mechanistic insight into electrocatalytic glyoxal reduction on copper ...
Glyoxal is not likely a key intermediate of CO 2 reduction to C 2 species, but its electroreduction on Cu yields the commodity chemicals ethylene glycol and ...
[24]
Synthesis, structure, and characterization of glyoxal‐urea ...
Jun 3, 2014 · This means that the reaction between MMU and G or the dehydration condensation reaction of MMU change the 13C chemical shifts in the C O group ...
[25]
Glyoxal (Cicads 57, 2004)
Summary of each segment:
[26]
Oligomer Formation in Evaporating Aqueous Glyoxal and Methyl ...
Both compounds remain primarily in the condensed phase due to oligomer formation when aqueous solution droplets are evaporated, regardless of concentration.Missing: distillation | Show results with:distillation
[27]
Aqueous-phase behavior of glyoxal and methylglyoxal observed ...
Feb 25, 2021 · The recorded C K-edge spectra show that glyoxal is completely hydrated in the dilute aqueous solutions, in line with previous studies.Missing: planar | Show results with:planar
[28]
Secondary Organic Aerosol-Forming Reactions of Glyoxal with ...
Glyoxal takes part in reversible hydration when it enters the condensed phase where it can be oxidized by OH and form oxalic acid. However, at typical ...
[29]
Endogenous alpha-oxoaldehydes and formation of protein and ...
Glyoxal, methylglyoxal and 3-deoxyglucosone are formed by the degradation of glycolytic intermediates, glycated proteins and lipid peroxidation. They are potent ...
[30]
Small reactive carbonyl compounds as tissue lipid oxidation products
Oct 8, 2012 · Small reactive carbonyl compounds (RCCs) such as formaldehyde, acetaldehyde, acrolein, crotonaldehyde, glyoxal ... endogenous formation in tissues ...
[31]
Isolation and Characterization of Advanced Glycation End ... - PubMed
These imidazolone compounds have been shown to originate from the reaction of arginine with glyoxal and methylglyoxal, respectively. A third ninhydrin ...
[32]
Accelerated formation of N epsilon-(carboxymethyl) lysine ... - PubMed
Accelerated formation of N epsilon-(carboxymethyl) lysine, an advanced glycation end product, by glyoxal and 3-deoxyglucosone in cultured rat sensory neurons.
[33]
Parkinsonism-associated protein DJ-1/Park7 is a major ... - PubMed
Jan 16, 2015 · Parkinsonism-associated protein DJ-1/Park7 is a major protein deglycase that repairs methylglyoxal- and glyoxal-glycated cysteine, arginine, and ...
[34]
Glyoxal-guanine DNA adducts: detection, stability and formation in ...
The glyoxal-deoxyguanosine adduct (gG) is formed from alpha ... Glyoxal-guanine DNA adducts: detection, stability and formation in vivo from nitrosamines.
[35]
Guanine glycation repair by DJ-1/Park7 and its bacterial homologs
Jul 14, 2017 · DNA damage induced by reactive carbonyls (mainly methylglyoxal and glyoxal), called DNA glycation, is quantitatively as important as oxidative ...
[36]
Differential effects of glyoxalase 1 overexpression on diabetic ...
Jun 11, 2014 · The reactive dicarbonyls, glyoxal and methylglyoxal (MG), increase in diabetes and may participate in the development of diabetic complications.
[37]
Exploring the Impact of Glyoxal Glycation on β-Amyloid Peptide (Aβ ...
Jun 3, 2021 · To clarify the impact of glycation on Aβ aggregation, we synthesized two glycated Aβ42 peptides by replacing Lys16 and Lys28 with Nε- ...
[38]
Glyoxal Induces Senescence in Human Keratinocytes through ...
In this study, we show that GO treatment provokes oxidative stress by increasing ROS and advanced glycation end-products levels and induces senescence in human ...
[39]
Glucose metabolite glyoxal induces senescence in telomerase ...
Mar 17, 2012 · Besides being a natural physiological metabolite in the auto-oxidation of glucose, GO can alternatively be formed by lipid peroxidation, the ...
[40]
OXALATE FORMATION FROM GLYOXAL IN ERYTHROCYTES - PMC
Glyoxal synthesis is elevated in diabetes, cardiovascular disease and other diseases with significant oxidative stress. Erythrocytes are a good model system ...
[41]
Emissions of Glyoxal and Other Carbonyl Compounds from ...
We report enhancements of glyoxal and methylglyoxal relative to carbon monoxide and formaldehyde in agricultural biomass burning plumes.<|separator|>
[42]
On-road vehicle emissions of glyoxal and methylglyoxal from tunnel ...
Aug 6, 2025 · The direct sources for glyoxal and methylglyoxal from vehicles are still unclear because of only a few investigations in the USA. Here we ...
[43]
Global budgets of atmospheric glyoxal and methylglyoxal, and ...
Aug 2, 2008 · Urban and suburban glyoxal and methylglyoxal concentrations can exceed 1 ppb due to emissions of very short-lived anthropogenic precursors ...
[44]
[PDF] Thermal processing of hydrogenated glyoxal ices under ... - HAL
Nov 17, 2021 · In the present paper, we have investigated the formation of organic residues by probing the thermal evolution of CHOCHO + H solid state reaction ...<|separator|>
[45]
Preparation of Acetylenediol (HOCCOH) and Glyoxal (HCOCHO) in ...
May 21, 2024 · Due to the abundance of carbon monoxide and water in interstellar ices, glyoxal and acetylenediol are suitable candidates for future ...
[46]
Glyoxal in Foods: Formation, Metabolism, Health Hazards, and Its ...
Feb 7, 2024 · Glyoxal is easily produced in diets high in carbohydrates and fats via the Maillard reaction, carbohydrate autoxidation, and lipid peroxidation ...Missing: interstellar medium
[47]
https://pubmed.ncbi.nlm.nih.gov/38284798/
[48]
DOAS measurement of glyoxal as an indicator for fast VOC ...
Apr 21, 2005 · During the day, photolysis and reaction with OH-radicals determine its atmospheric residence time [Atkinson, 2000]. We present the first direct ...
[49]
https://agupubs.onlinelibrary.wiley.com/doi/full/10.1029/2005GL022616
[50]
Cross linking agents for paper binders and paper coated therewith
As a comparison, similar compositions are formulated with glyoxal being employed as the cross-linking agent. Catalyst is added at a 10 percent amount based on ...Missing: industry | Show results with:industry
[51]
Cross-Linking Agents in Three-Component Materials Dedicated to ...
Sep 23, 2024 · Glyoxal has high water solubility and can be easily used as a cross-linking agent for proteins and polysaccharides [33,34,35,36,37]. It has been ...
[52]
Easy Care and Durable Press Finish of Cellulosics | Glyoxal Resins
This chemical is the basis for about 90% of easy-care and durable press finish products on the market. DMDHEU is synthesized from urea, glyoxal and formaldehyde ...
[53]
Assessment of durable press performance of cotton finished with ...
Sep 28, 2017 · DMDHEU is manufactured from urea, glyoxal and formaldehyde, by reacting one molecule of urea with one molecule of glyoxal followed by ...Missing: permanent | Show results with:permanent
[54]
Study on Various Compositions of Polyvinyl Alcohol and Starch ...
The blends have been cross-linked with glyoxal to enhance its properties. The hydroxyl groups of PVA and starch react with glyoxal via formation of acetal bonds ...
[55]
Cross-linked PVOH coatings having enhanced barrier characteristics
The oxygen barrier is a layer of cross-linked polyvinyl alcohol and glyoxal, which exhibits improved barrier characteristics to the transmission of oxygen.
[56]
The Benefits of Glyoxal 40% for Textiles, Paper, and Water Treatment
Glyoxal is an essential ingredient in textile processing, paper manufacturing, oil and gas, and water treatment industries.
[57]
Premium Glyoxal 40% - California Chemical
Chemical Structure & Properties. Glyoxal (OHC-CHO). Glyoxal molecular structure. CAS: 107-22-2 | EC: 203-474-9 | Formula: OHC-CHO. Smallest dialdehyde | MW ...
[58]
Glyoxal Market Size, Share and Growth Statistics - 2035
The global glyoxal market is valued at USD 1.66 billion in 2025. As per Fact.MR analysis, it will grow at a CAGR of 4.4% and reach USD 2.79 billion by 2035.Glyoxal Market Outlook (2025... · Glyoxal Industry Dynamics... · Glyoxal Demand Analysis And...<|separator|>
[59]
Glyoxal Market Global Forecast to 2024 | MarketsandMarkets
The requirement for glyoxal as a crosslinker is expected to grow in the future due to the increasing demand for textiles, paper packaging, footwear, garments, ...Missing: apparel | Show results with:apparel
[60]
Imidazole synthesis - Organic Chemistry Portal
A ketone oxidation, employing catalytic HBr and DMSO, followed by imidazole condensation with aldehydes provides 2,4(5)-disubstituted imidazoles in good yields.
[61]
2,3-Pyrazinedicarboxylic acid. - Organic Syntheses Procedure
Notes. 1. In the absence of sodium bisulfite, aqueous glyoxal solutions react with o-phenylenediamine to give only about 30% yields of quinoxaline together with ...
[62]
One-pot preparation of pyrrole derivatives via the copper-catalyzed ...
The key feature in this annulation is the in-situ generation of an N,O-hemiacetal intermediate from either the glyoxylate or the glyoxal and a secondary amine.
[63]
Synthesis and therapeutic potential of imidazole containing ...
Feb 18, 2021 · Imidazole was first named glyoxaline because the first synthesis has been made by glyoxal and ammonia. It is the basic core of some natural ...
[64]
Yellow, orange benzimidazolone like azo dye making method
The composition principle of yellow and orange benzoglyoxaline ketone azo pigment is seen " kind of pigment dyestuff and application " (Shen Yongjia work, ...
[65]
Glyoxal as an alternative fixative to formaldehyde in immunostaining ...
Nov 16, 2017 · Glyoxal penetrates cells faster than conventional solutions of PFA. Glyoxal fixes and retains more cellular proteins and RNA than PFA.
[66]
Glyoxal fixation: An approach to solve immunohistochemical ... - NIH
Jul 14, 2023 · We found that glyoxal fixation greatly improved antibody penetration and immunoreactivity, uncovering signals for buried molecules by conventional ...
[67]
[PDF] Amended Safety Assessment of Glyoxal as Used in Cosmetics
May 19, 2017 · The polymerization depends on both the pH and the concentration of. Glyoxal in the solution. The main oligomeric forms are the dioxolane dimer ...
[68]
Glyoxal
Summary of each segment:
[69]
Glyoxal damages human aortic endothelial cells by perturbing the ...
Dec 18, 2021 · Exposure to glyoxal was found to be linked to abnormal glutathione activity, the collapse of mitochondrial membrane potential, and the activation of mitogen- ...
[70]
Role of Advanced Glycation End Products in Carcinogenesis ... - NIH
AGEs, when accumulated in tissues, significantly increase the level of inflammation in the body which has long been associated with the development of cancer.
[71]
a role for glyoxal in protein damage in diabetes - PubMed Central
We propose that glyoxal (GO) is a major contributor to extracellular matrix (ECM) damage in diabetes. Here, we review the current knowledge and provide new data ...
[72]
Glyoxal 40 Suppliers, Dealers in Mumbai, India - Shakti Chemicals
Storage Conditions: Store in a cool (5–25 °C), dry, and well-ventilated area, away from heat sources. Avoid direct light to avert oxidative breakdown or ...
[73]
https://www.fishersci.com/store/msds?partNumber=BP1370500&productDescription=GLYOXAL%2BAQUEOUS%2BELEC%2B500ML&vendorId=VN00033897&countryCode=US&language=en
[74]
[PDF] SAFETY DATA SHEET - Fisher Scientific
Sep 12, 2014 · Glyoxal, 40 wt% solution in water. Revision Date 24-Dec-2021. Causes serious eye irritation. May cause an allergic skin reaction. Harmful if ...
[75]
[PDF] AK Scientific, Inc.
Ensure adequate ventilation. ... Precautions for safe handling: Avoid contact with skin, eyes, and personal clothing. ... Glyoxal sodium bisulfite. Page 5 of 5.
[76]
ICSC 1162 - GLYOXAL (40% solution) - INCHEM
The solution in water is a weak acid. Formula: C2H2O2 / OHCCHO Molecular mass: 58.0. Boiling point: 104°C Melting point: -14°C Relative density (water = 1): ...
[77]
[PDF] GLYOXAL 40% - LabelSDS
Dec 4, 2019 · Acute oral toxicity. : Acute toxicity estimate: > 5,000 mg/kg. Components: 107-22-2: Acute inhalation toxicity. : LC50 (Rat): Exposure time: 4 h.
[78]
[PDF] GLYOXAL - CAMEO Chemicals
... oral rat LD50 = 2,020 mg/kg. 3.8 Toxicity by Inhalation: Currently not available. 3.9 Chronic Toxicity: Currently not available. 3.10 Vapor (Gas) Irritant ...
[79]
[PDF] Opinion of the Scientific Committee on Consumer Products (SCCP ...
The equilibrium between monomer and dimer and trimer depends largely on the glyoxal concentration in the aqueous solution: - in a 5% solution, 39% of glyoxal is ...
[80]
[PDF] Revision date: March 2021 1 GLYOXAL This dossier on ... - Santos
Glyoxal exhibits a low concern for toxicity to aquatic organisms, as well as to terrestrial invertebrates and plants. Key physical and chemical properties for ...
[81]
[PDF] Safety data sheet - SMS Rail Lines
Toxicity to fish: LC50 (96 h) > 186 - < 272 mg/l, Leuciscus idus (DIN 38412 Part 15, static). The details of the toxic effect relate to the nominal ...
[82]
[PDF] GLYOXAL CAS N°: 107-22-2
Glyoxal (CAS 107-22-2) has moderate oral toxicity, low dermal toxicity, and can cause skin irritation. It is a sensitizer and has a melting point of -14°C (40% ...Missing: absorption | Show results with:absorption