GLYOXAL
GLYOXAL
Glyoxal
CAS No.: 107-22-2
www.atamankimya.com
Other names: Ethanedial; Biformal; Biformyl; Diformyl; Ethanedione; Glyoxal aldehyde; Glyoxylaldehyde; Oxal; Oxalaldehyde; 1,2-Ethanedione; (CHO)2; Diformal; Ethane-1,2-dione; Ethandial; Aerotex glyoxal 40; ODIX; Protectol GL 40
Synonyms:
diformal
ethandial
ethane dial
ethane-1,2-dial
ethanedial
ethanedione
1,2- ethanedione
gelifundol
glyoxal aldehyde
glyoxylaldehyde
oxalaldehyde
oxaldehyde
Anhydrous glyoxal (CAS No. 107-22-2) has a melting point of about 15 °C.
However, glyoxal is generally available as an aqueous solution (typically containing 30–50% glyoxal) in which hydrated oligomers are present.
Glyoxal is used as a chemical intermediate in the production of pharmaceuticals and dyestuffs, as a cross-linking agent in the production of a range of different polymers, as a biocide, and as a disinfecting agent.
Due to glyoxal’s divergent properties, Glyoxal is highly explored as a crosslinking agent in wood, textile and paper industries; as a sulfur scavenger and biocide in oil and gas applications and as an effective co-biocide agent in disinfection applications used in veterinary and health sectors.
As glyoxal fits well in the sustainability trend, it is likely to become an important chemical intermediate for end-user industries in the future.
Glyoxal 40 % is a colorless to pale yellow and transparent liquid which boils at 104°C.
Glyoxal 40 % is most widely used as a cross-linking agent in the production of permanent press resins for textiles, of moisture resistant glues and adhesives, as well as moisture resistant foundry binders.
Glyoxal 40% is also used to improve the wet strength of paper and the moisture resistance of leather.
Thanks to its versatile properties, glyoxal is the product of choice for various applications.
In textile manufacturing, for example, this efficient crosslinker decreases water uptake in crosslinking cellulose.
In oil recovery, glyoxal crosslinks polymers, thus increasing the viscosity of fracturing fluids.
Glyoxal is also used in the paper, leather and epoxy industries.
In addition to known applications, glyoxal shows potential for new applications which are still in the early stages of development.
Nearly 80% of Glyoxal to be Consumed as a Crosslinking Agent in 2019
Application of glyoxal as a crosslinking agent has remained traditional across multiple end-user industries and the status-quo is expected to continue in the future.
According to the study, nearly 80% of the global glyoxal was consumed as a crosslinking agent.
Glyoxal provides a comprehensive crosslinking solution for a wide range of polymers such as starch, polyacrylamide, cellulose, proteinaceous material and polyvinyl alcohols.
As manufacturers continue to invest more in R&D for the development of biodegradable glyoxal, its application as a crosslinking is likely to grow in the future.
Glyoxal is used as a chemical intermediate in the production of pharmaceuticals and dyestuffs.
Glyoxal is also used in the industrial production of α-hydroxyalkylureas (the addition of glyoxal to urea) and is industrially employed as a cross-linking agent in the production of a range of different polymers, such as textiles (e.g., permanent press fabrics), paper , and proteins .
Glyoxal is used as a biocide and as a disinfecting agent and is present in many products, such as cleansers used for the disinfection of surfaces
Glyoxal is an organic compound with the chemical formula OCHCHO.
Glyoxal is the smallest dialdehyde (a compound with two aldehyde groups).
Glyoxal is a crystalline solid, white at low temperatures and yellow near the melting point (15 °C). The liquid is yellow, and the vapor is green.
Glyoxal (CAS No. 107-22-2; C2H2O2) is also known as ethanedial, diformyl, ethanedione, biformal, and oxal.
At room temperature, anhydrous glyoxal is a liquid, with a melting point of about 15 °C.
Glyoxal crystallizes in its monomeric form to yield yellow, irregular to prism-like crystals.
However, it is generally employed as an aqueous solution (typically containing 30–50% glyoxal), in which hydrated oligomers are present due to nucleophilic addition.
Glyoxal can undertake rotational isomerization between the planar cis and trans conformations, with trans-glyoxal being the more stable isomer
Glyoxal is the dialdehyde that is the smallest possible and which consists of ethane having oxo groups on both carbons.
Glyoxal has a role as a pesticide, an agrochemical, an allergen and a plant growth regulator.
APPLICATION OF GLYOXAL IN CONSTRUCTION INDUSTRY:
Glyoxal 40% had a wide range of uses.
Glyxal can be used in paper industry ,textile industry and intermediate area,ect.
Recently years, Glyoxal 40% also to be widely used in construction industry.
In Construction industry, glyoxal 40% is used as the cement curing agent to improve the solidification strength
To control landslides Glyoxal can be used.Glyoxal prevents the loss of mud
But there are some customers thought the opppsite.
Commonly, the solidification speed is 20 minutes. The setting rate is mainly decided by ethylene glycol(the raw material of glyoxal ).ethylene glycol is anticoagulant and antifreeze. So,the content of ethylene glycol will be directly affects the solidification rate. Commonly, the ethylene glycol content is aroud 1.5% in glyoxal.
Our factory Zhonglan is a professional manufacturer of gly
Coatings
Glyoxal is used to produce glycoluril based amino crosslinking resins for powder coatings, liquid can and coil coatings.
Glyoxal emits less formaldehyde and produce more flexible films compared to other amino crosslinkers.
Electronics
Glyoxal is a building block for the glycidated phenol compound (tetraglycidyl ether of tetrakis(4-hydroxyphenyl) ethane).
This increases stability in epoxy laminates and molding compounds.
Oilfield
The sulfur scavenging property of Glyoxal to act as a H2S scavenger and glyoxal-crosslinked polymers (hydrocolloids) can be used to improve viscosity in oil-drilling fluids.
Oil and gas industry is another important end user landscape for glyoxal market wherein glyoxal is increasingly used in the oil extraction and enhanced oil recovery processes.
Also, glyoxal is used as a sulfur scavenger in the gas sweetening applications.
The oil production activities are growing in developed and developing countries, thereby providing opportunities for glyoxal manufacturers.
Paper
Polymers crosslinked with Glyoxal are used to enhance the wet/dry strength and enable the efficient coating of paper.
Personal care
In cosmetics, Glyoxal-crosslinked polymers (hydrocolloids) improves the viscosity.
Textile
As a crosslinker, Glyoxal is used in antiwrinkle and softening polymer. It is also used as a crosslinker in leather tanning processes
Glyoxal is a kind of fine chemical product with a wide range of applications.
Glyoxal is mainly used in chemical, medicine, paper making, flavor, coating, adhesive and daily-use chemicals.
Glyoxal can be directly synthesized into imidazole, 2-methylimidazole, glyoxalic acid, textile finishing agent, iron-free resin and paper making auxiliaries, etc.
In the textile industry, glyoxal can increase the spinning and anti-wrinkle of cotton, nylon as a fiber treatment agent.
In Japan, 80% consumption of glyoxal is used as a fiber treatment agent. The glyoxal biocide is an insoluble adhesive.
Glyoxal is also used in the leather industry and waterproof matches production.
With consumers demanding non-woven, soft and wrinkle-free clothing, utilization of glyoxal in the textile and apparel sectors is likely to increase in the coming years.
However, with the advent of synthetic fibers, in the long run, application of glyoxal in the textile industry is estimated to decline.
Nearly 27% of the glyoxal consumption was held by the paper & packaging industry in 2018. Glyoxal finds an extensive application as a crosslinker in the paper & packaging industry.
Water
The biocidal effect of glyoxal is used in water treatment
Glyoxal has been traditionally used as a synthetic preservative in the personal care ingredients and cosmetics.
However, formaldehyde-releasing chemical compounds have been assessed for their harmful effects on skin and have been categorized as a carcinogen.
Despite the use of glyoxal as an alternative to formaldehyde, the personal care and cosmetic industry’s increasing preference for natural ingredients is likely to reduce glyoxal utilization in the industry.
Other
Glyoxal is used to crosslink a wide range of other polymers, including starch, cellulose, proteinaceous material, polyacrylamide and polyvinyl alcohols.
In disinfection applications, Glyoxal is a biocidal active ingredient.
Finally, Glyoxal can be used in wood hardening application for improved moisture resistance.
Table 1: Physicochemical properties of glyoxal and its commercially employed aqueous solution (40%).
PROPERTIES OF GLYOXAL
Glyoxal
Relative molecular mass: 58.04
Density: (g/cm3) 1.14 (20 °C) Lide (1995)
Refractive index: 1.3826 (20 °C) Lide (1995)
Melting point: (°C) 15 Brabec (1993)
Boiling point: (°C) 50.4 (101.3 kPa) Lide (1995)
Vapour pressure: (kPa)29.33 (~20 °C) Brabec (1993)
Water solubility (g/litre): 600 (25 °C) Hoechst AG (1994)
40% aqueous solution of glyoxal
Vapour pressure(kPa): 2.03 (20 °C)
Density: (g/cm3) 1.27 (20 °C)
Viscosity: (mPa·s) 5–10 (23 °C)
Setting point (°C): ~ –10
pH of aqueous solution: 2.1–2.7
Glyoxal 40%
Formula : C2H2O2
Physical form
Anhydrous glyoxal is a liquid at ambient temperature; it crystallizes at 15 °C in the form of yellow prismatic crystals.
Molecular weight : 58.04
Solubility: Very soluble in water (600 g/l), miscible in water in all ratios (40% aqueous solution), soluble in ethanol and ethyl ether
Organoleptic properties : Colourless, deliquescent powder (pure substance) colourless liquid (40% solution)
Melting point : 15 C (pure substance), -10vC (40% solution)
Boiling point : 50.4 C (pure substance), 105 C (40% solution)
Vapour pressure : 293.3 hPa at 20 C (pure substance), < 10-4 kPa (40% solution)
Density : 1.14 g/cm3 at 20oC (pure substance), 1.27 g/cm3 (40% solution)
pH : 2.1 – 2.7 (20 C, 40% solution)
Stability : 40% aqueous solution of glyoxal is stable at room temperature at least for 6 months, when stored in dark
Purity, composition, and substance codes
Anhydrous Glyoxal can only be produced in the laboratory and does not exist in a stable form.
Glyoxal is commonly supplied in the form of aqueous solution at 40% (w/w) (expressed in CHOCHO).
Less concentrated forms have been formerly commercialized (essentially at 30% w/w). Very small quantities of an 80% powder are produced (less than 0.1 % of the marketed quantities).
The hydrated monomer (ethane bis-gemdiol) is the main form of glyoxal in aqueous solution.
However this gemdiol tends to polymerize to acetals and semiacetals. The polymerisation depends on both the pH and the concentration of the solution.
The main oligomeric forms are the dioxolane dimer and the bis(dioxolane) trimer.
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 present in the monomer form;
– in a 40% solution, the monomer (I) content amounts to as little as 11% of glyoxal, the dimer (II) and trimer (III) forms being dominant.
The nature of the impurities depends on the synthesis route used. If the process used is the oxidation of acetaldehyde with nitric acid diluted in an aqueous medium, the main impurities are the following:
• <200 ppm formaldehyde
• formic acid, acetic acid, glyoxalin acid and glycolic acid – in total approximately 1500 ppm
If the process used is the oxidation of 1,2-ethanediol with oxygen in the presence of water, glyoxal is mainly contaminated with:
• 5000 ppm hydroxyacetaldehyde
• 1500 ppm 1,2-ethanediol
• approximately 1000-2000 ppm organic acids
Former production processes yielded glyoxal with acid contents of up to 2.1% total acids and 1000 ppm of formaldehyde.
Function and uses
Glyoxal is marketed mainly as a 40% aqueous solution. Glyoxal is used as starting point for the production of a number of other compounds.
The dual functionality and the ability of glyoxal to form heterocyclic compounds are used in the production of resins and for cross-linking functionalized macromolecules such as cellulose, polyacrylamides, polyvinyl alcohol, keratin and other polycondensates.
With cellulose, unstable hemiacetals are obtained in the cold, which irreversibly form acetals when heated in the presence of acid catalysts.
In Annex I of the Cosmetic Directive several cosmetic products using hydroxyl-ethyl cellulose R-types are listed (e.g., creams, emulsions, lotions, gels and oils for skin, face masks, tinted bases, different powders (make-up, after bath, hygienic), hair-care products (tints, bleaches, cleansing and conditioning products), shaving products, sunbathing, tanning etc.).
The maximum glyoxal level is 100 ppm in the cosmetic product. In finished cosmetic products, glyoxal is present only as residual from polymerising reactions.
Odor: characteristic
Use: Glyoxal shows a wide range of activities, e.g. as a versatile crosslinker, as an intermediate for organic syntheses, as a biocide, and as a scavenger for a diverse range of nucleophiles.
Glyoxal is an organic compound with a complex structure. In its liquid state it is yellow in color and when it evaporates it turns to a green colored gas. The compound is often a preferred choice for use in many different types of manufacturing.
The substance is available for purchase to those who use it in the manufacturing of their products.
Chemical Properties
The chemical formula for Glyoxal is OCHCHO or C2H2O2. It’s the smallest dialdehyde which is a more complex structure.
Glyoxal is commonly prepared using the Laporte process or through the liquid-phase oxidation of acetaldehyde with nitric acid.
Glyoxal was first produced commercially in France in 1960.
Since then, there have been many uses found for Glyoxal.
Glyoxal is used in a great many instances as a solubilizer, an agent that increases the solubility of a substance.
For this reason glyoxal is used commonly as an additive to many commercial formulas where increased solubility is desired.
Glyoxal is also known as ethanedial or ethane 1,2-dione. Another common name is Glyoxyladehyde.
It is provided as SDS Glyoxal 40; it has 40% strength.
Glyoxal is a colorless, transparent liquid with a content of 40% plus or minus .5%.
Uses
Glyoxal is used to crosslink starch-based formulas in textile finishes and in coated paper. ,
Glyoxal also used in textile production, leather tanning, cosmetics, epoxy, oil and gas industries and disinfection.
Glyoxylic acid has industrial uses including the curing of wood and wood hardening.
Glyoxal is also used as a fixative in a method of preserving cells for examination under a microscope.
Various concentrations of Glyoxal are used in different types of uses.
There are many specific uses in the manufacturing of various products.
For example, Glyoxal is used in disinfectants that are used both in the health industry and for veterinary hygiene.
When used in cosmetics Glyoxal improves the viscosity of the products. In leather production, glyoxal helps preserve the leather quality.
Glyoxal is often used in epoxy to give it more stability and better performance.
Glyoxal is also accredited for use in the manufacture of food packaging.
It is important to note that it is readily biodegradable when used according to OECD guidelines.
ODIX;Oxal;(CHO)2;GLYOXA;GLYOXAL;DIFORMYL;GLYOXALE;Biformal;Biformyl;Diformal
Chemical Properties: colourless or light yellow liquid
Uses : Permanent-press fabrics; dimensional stabilization of rayon and other fibers. Insolubilizing agent for compounds containing polyhydroxyl groups (polyvinyl alcohol, starch, and cellulosic materials); insolubilizing of proteins (casein, gelatin, and animal glue); embalming fluids; leather tanning; paper coatings with hydroxyethylcellulose; reducing agent in dyeing textiles.
Uses: Glyoxal is used in the production of textiles and glues and in organic synthesis.
Definition: ChEBI: The dialdehyde that is the smallest possible and which consists of ethane having oxo groups on both carbons.
General Description : Yellow crystals melting at15°C. Hence often encountered as a light yellow liquid with a weak sour odor. Vapor has a green color and burns with a violet flame.
Air & Water Reactions: Mixtures with air may explode. Polymerizes quickly on standing, or on contact with a trace of water (possibly a violent reaction), or when dissolved in solvents containing water, [Merck, 502(1968)]. Soluble in water. An aqueous solution contains mono molecular Glyoxal. [Hawley]
Reactivity Profile: Glyoxal reacts vigorously with strong oxidizing agents such as nitric acid. Polymerizes rapidly even at low temperature if anhydrous [Noller]. Aqueous solutions are more stable but also polymerize on standing. Reacts with itself in the presence of base to give glyconates. Undergoes addition and condensation reactions that may be exothermic with amines, amides, aldehydes, and hydroxide-containing materials. Mixing in equal molar portions with any of the following substances in a closed container caused the temperature and pressure to increase: chlorosulfonic acid, oleum, ethyleneimine, nitric acid, sodium hydroxide [NFPA 1991].
Hazard: Mixture of vapor and air may explode. Questionable carcinogen.
Health Hazard: Glyoxal is a skin and eye irritant; the effectmay be mild to severe. Its vapors are irritatingto the skin and respiratory tract. Anamount of 1.8 mg caused severe irritation inrabbits’ eyes. Glyoxal exhibited low toxicityin test subjects. Ingestion may cause somnolenceand gastrointestinal pain.
LD50 value, oral (guinea pigs): 760 mg/kg.
Health Hazard: Inhalation causes some irritation of nose and,40% solution throat. Contact with liquid,40% solution irritates eyes and causes mild irritation of skin; stains skin yellow. (No information available on symptoms of ingestion.)
Fire Hazard: Behavior in Fire: Heat may cause polymerization to a combustible, viscous material.
Safety Profile: Low toxicity by SYN: AEROTEX GLYOXAL 40 ingestion and skin contact. A skin irritant. A powerful reducing agent. May explode on contact with air. Polymerizes violently on contact with water. During storage it may spontaneously polymerize and ignite. Reacts violently with chlorosulfonic acid, ethylene imine, HNO3, oleum, NaOH, can cause violent reactions. Can explode during manufacture. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.
Waste Disposal: Glyoxal is mixed with a combustible solventand burned in a chemical incineratorequipped with an afterburner and scrubber.
Synonyms:
diformal
ethandial
ethane dial
ethane-1,2-dial
ethanedial
ethanedione
1,2- ethanedione
glyoxal aldehyde
glyoxylaldehyde
oxalaldehyde
oxaldehyde
Preferred IUPAC name
Ethanedial
Other names
Glyoxal
Oxaldehyde
oxaldehyde
Oxalaldehyde
CAS Number
107-22-2 check
Properties
Chemical formula: C2H2O2
Molar mass: 58.036 g·mol−1
Density: 1.27 g/cm3
Melting point: 15 °C
Boiling point: 51 °C
Heat capacity (C): 1.044 J/(K·g)
Flash point: −4 °C
Autoignition temperature: 285 °C
Related aldehydes acetaldehyde
glycolaldehyde
propanedial
methylglyoxal
Related compounds glyoxylic acid
glycolic acid
oxalic acid
pyruvic acid
diacetyl
acetylacetone
Ethanedial
107-22-2
Oxalaldehyde
oxaldehyde
Molecular Weight: 58.04 g/mol
Name: oxaldehyde
CAS Number:107-22-2
Other: 83513-30-8
Molecular Weight:58.03634000
Formula:C2 H2 O
Cosmetic Uses: antimicrobial agents
Primary name and/or INCI name: Glyoxal (INCI name)
Chemical names: Ethandial (IUPAC), Biformal, Biformyl, Diformyl, 1,2-Ethandial, Ethanedione, Glyoxalaldehyde, Glyoxal aldehyde, Oxal, Oxalaldehyde, Oxaldehyde, Odix
Trade names and abbreviations: Aerotex Glyoxal 40, Daicel GY 60, Glyfix CS 50, Glyoxal 40, Glyoxal P, Gohsezal P, Odix, Parez 802, Permafresh 144, Protectol GL
CAS : 107-22-2
EINECS : 203-474-9
Glyoxal can undertake rotational isomerization between the planar cis and trans conformations,with trans-glyoxal being the more stable isomer
Suppliers:
Glyoxal 40%
Odor: characteristic
Use: Glyoxal shows a wide range of activities, e.g. as a versatile crosslinker, as an intermediate for organic syntheses, as a biocide, and as a scavenger for a diverse range of nucleophiles.
Odor: characteristic
Use: Glyoxal links a wide range of polymers, e.g. starch, cellulose, proteinaceous material, polyacrylamide, polyvinyl alcohols.
Ethanedial, Oxalaldehyde
Odor: characteristic
Use: Is used as a solubilizer and cross-linking agent in polymer chemistry for: proteins (leather tanning process), collagen, cellulose derivatives (textiles), hydrocolloids, and starch (paper coatings).
Safety Information:
Xn – Harmful.
R 20 – Harmful by inhalation.
R 36/38 – Irritating to skin and eyes.
R 43 – May cause sensitisation by skin contact.
R 68 – Possible risk of irreversible effects.
S 02 – Keep out of the reach of children.
S 20/21 – When using do not eat, drink or smoke.
S 23 – Do not breath fumes.
S 24/25 – Avoid contact with skin and eyes.
S 26 – In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37 – Wear suitable protective clothing and gloves.
Formulations/Preparations:
•commercially available in anhydrous form as crystalline dihydrate, or as a 40% aqueous solution which may contain polymerization inhibitors.
dihydrate grades: 40% solution; pure, solid; vp.
•glyoxal is a dialdehyde supplied commercially as 30% aqueous solution, consisting of mixture of monomeric & polymeric hydrates along with small amounts of impurities which render the solution acid.
•glyoxal can undertake rotational isomerization between the planar cis and trans conformations, with trans-glyoxal being the more stable isomer.
•…it is generally employed as an aqueous solutionin which hydrated oligomers are present due to nucleophilic addition. …some of the most important hydrated derivatives of glyoxal formed by nucleophilic addition in aqueous solutioninclude the monomer ethane-1,1,2,2-tetraol (i), the dimer 2-dihydroxymethyl-(1,3)dioxolane-4,5-transdiol (ii), and the trimer bis(dioxolane) (i.e., 2,2′-bi-1,3-dioxolanyl-4,4′,5,5′-tetraol) (iii) – both cis and trans configurations. however, the proportion of the different structures varies with concentration and ph.
Glyoxal is the dialdehyde that is the smallest possible and which consists of ethane having oxo groups on both carbons. It has a role as a pesticide, an agrochemical and an allergen.
Glyoxal appears as yellow crystals melting at15°C. Hence often encountered as a light yellow liquid with a weak sour odor. Vapor has a green color and burns with a violet flame.
Production
Glyoxal was first prepared and named by the German-British chemist Heinrich Debus (1824–1915) by reacting ethanol with nitric acid.
Commercial glyoxal is prepared either by the gas-phase oxidation of ethylene glycol in the presence of a silver or copper catalyst (the Laporte process) or by the liquid-phase oxidation of acetaldehyde with nitric acid.
The first commercial glyoxal source was in Lamotte, France, started in 1960.
The single largest commercial source is BASF in Ludwigshafen, Germany, at around 60,000 tons per year.
Other production sites exist also in the US and China.
Commercial bulk glyoxal is made and reported as a 40%-strength solution in water.
Laboratory methods
Glyoxal may be synthesized in the laboratory by oxidation of acetaldehyde with selenious acid.
Anhydrous glyoxal is prepared by heating solid glyoxal hydrate(s) with phosphorus pentoxide and condensing the vapors in a cold trap.
Advanced glycation end-products (AGEs) are proteins or lipids that become glycated as the result of a high-sugar diet.
They are a bio-marker implicated in aging and the development, or worsening, of many degenerative diseases, such as diabetes, atherosclerosis, chronic kidney disease, and Alzheimer’s disease.
Applications
Coated paper and textile finishes use large amounts of glyoxal as a crosslinker for starch-based formulations. It condenses with urea to afford 4,5-dihydroxy-2-imidazolidinone, which further reacts with formaldehyde to give the bis(hydroxymethyl) derivative dimethylol ethylene urea, which is used for wrinkle-resistant chemical treatments of clothing, i.e. permanent press.
Glyoxal is used as a solubilizer and cross-linking agent in polymer chemistry.
Glyoxal is a valuable building block in organic synthesis, especially in the synthesis of heterocycles such as imidazoles.
A convenient form of the reagent for use in the laboratory is its bis(hemiacetal) with ethylene glycol, 1,4-dioxane-2,3-diol. This compound is commercially available.
Glyoxal solutions can also be used as a fixative for histology, that is, a method of preserving cells for examining them under a microscope.
Glyoxal and its derivatives are also used in the chemical probing of RNA structure, as they react with free guanines in RNAs.
Glyoxal is supplied typically as a 40% aqueous solution.
Like other small aldehydes, glyoxal forms hydrates. Furthermore, the hydrates condense to give a series of oligomers, some of which remain of uncertain structure.
For most applications, the exact nature of the species in solution is inconsequential.
At least one hydrate of glyoxal is sold commercially, glyoxal trimer dihydrate: [(CHO)2]3(H2O)2 (CAS 4405-13-4).
Other glyoxal equivalents are available, such as the ethylene glycol hemiacetal 1,4-dioxane-trans-2,3-diol (CAS 4845-50-5, m.p. 91–95 °C),
It is estimated that, at concentrations less than 1 M, glyoxal exists predominantly as the monomer or hydrates thereof, i.e., OCHCHO, OCHCH(OH)2, or (HO)2CHCH(OH)2.
At concentrations above 1 M, dimers predominate. These dimers are probably dioxolanes, with the formula [(HO)CH]2O2CHCHO.
Dimer and trimers precipitate as solids from cold solutions.
Other occurrences
Glyoxal has been observed as a trace gas in the atmosphere, e.g. as an oxidation product of hydrocarbons.
Tropospheric concentrations of 0–200 ppt by volume have been reported, in polluted regions up to 1 ppb by volume.
Safety
The LD50 (oral, rats) is 3300 mg/kg, which is very high.
GLYOXAL
Ethanedial
107-22-2
Oxalaldehyde
oxaldehyde
1,2-Ethanedione
Glyoxylaldehyde
Biformal
Biformyl
Diformal
Diformyl
Ethanedial, trimer
Aerotex glyoxal 40
Glyoxal aldehyde
Ethanediol, trimer
Glyoxal, 40%
Glyoxal solutions
C2H2O2
Glyoxal, 29.2%
EINECS 203-474-9
Glyoxal, 40% in water
Ethanedione
CAS-107-22-2
Glyoxal, pure, 40 wt.% solution in water
Glyoxal solution, ~40% in H2O (~8.8 M)
hydroxyketene
oxypolygelatine
Oxypolygelatin
Ethandial
Glycoxal
ethane dial
Glyoxal solution
(oxo)acetaldehyde
2-hydroxyethenone
2-oxoacetaldehyde
ethane-1,2-dial
Protectol GL 40
glyoxal (ethanedial)
ODIX
oxalic acid dihydride
hydroxymethylene ketone
Glyoxal, 40 % Solution
EC 203-474-9
Glyoxal solution, 40.0%
4-01-00-03625 (Beilstein Handbook Reference)
(CHO)2
Glyoxal, Biformyl, Oxalaldehyde
Glyoxal, 40% solution in water
Glyoxal, 40% w/w aq. soln.
Glyoxal solution, 40 wt. % in H2O
1,2-Ethanedione
Other
Aerotex glyoxal 40
Biformal
Biformyl
Diformal
Diformyl
ethandial
ethandial … %
Ethanedial
Glyoxal
glyoxal
Glyoxal, 29.2%
Glyoxal, 40%
glyoxal; ethandial
Glyoxylaldehyde
Oxal
Oxalaldehyde
Translated names
…% glioksalis (lt)
Etaandiaal … % (et)
etan-1,2-dion … % (no)
etandial … % (no)
etandial … % (ro)
etandial … % (sl)
etandial…% (hr)
etandiale…% (it)
etanodial …% (pl)
etanodial…% (pt)
ethandial … % (cs)
Ethandial … % (de)
etándiál (sk)
etándiál …% (hu)
etándiál…% (sk)
Glioksal (hr)
Glioksal (pl)
Glioksal (sl)
glioksal …% (pl)
glioksal…% (hr)
glioksal…% (sl)
Glioksalis (lt)
Glioksāls (lv)
Gliossal (mt)
Gliossale (it)
gliossale…% (it)
Glioxal (es)
Glioxal (pt)
Glioxal (ro)
glioxal … % (ro)
glioxal…% (es)
glioxal…% (pt)
Glioxál (hu)
glioxál …% (hu)
Glyoksaali (fi)
glyoksaali…% (fi)
glyoksal … % (no)
glyoxal (cs)
glyoxal (da)
Glyoxal (de)
Glyoxal (fr)
Glyoxal (nl)
Glyoxal (no)
Glyoxal (sv)
glyoxal … % (cs)
glyoxal à …%; éthanedial à…% (fr)
glyoxal…% (da)
Glyoxal…% (de)
glyoxal…% (nl)
glyoxal…% (sv)
glyoxál…% (sk)
Glükoksaal … % (et)
Glüoksaal (et)
éthanedial…% (fr)
Γλυοξάλη (el)
γλυοξάλη …% (el)
Глиоксал (bg)
глиоксал…% (bg)
етандиал…% (bg)
…% etandialis (lt)
…% etāndiāls (lv)
…% glioksāls (lv)
CAS names: Ethanedial
IUPAC names: 1,2 ethandial
ethandial
ethandial 40%
ethandial … %
Ethanedial
ethanedial
GLYOXAL
Glyoxal
glyoxal
Glyoxal
oxalaldehyde
oxalaldehyde
oxaldehyde
Trade names
1,2-Ethanedial (chemical name)
1,2-Ethanedione
Biformal
Biformyl
Daicel GY 60
Diformyl
Ethanedial (9CI)
Ethanedione
Glyfix CS 50
Glyoxal (8CI)
Glyoxal (common name)
Glyoxal 40 liq
Glyoxal aldehyde
Glyoxylaldehyde
Gohsezal P
Oxal
Oxalaldehyde
Permafresh 114
Protectol GL
Protectol GL 40
Index Number
83513-30-8
Other
CAS number
83513-30-8
Other
Deleted CAS number
1,2-Ethanedione
107-22-2 [RN]
1732463 [Beilstein]
203-474-9 [EINECS]
50NP6JJ975
Diformal
ethandial
Ethanedial [ACD/Index Name]
Ethanedione
Glyfosfin
Glyoxal [Wiki]
MFCD00006957 [MDL number]
Oxalaldehyd [German] [ACD/IUPAC Name]
Oxalaldehyde [ACD/IUPAC Name]
Oxalaldéhyde [French] [ACD/IUPAC Name]
(CHO)2 [Formula]
203-474-9MFCD00006957
40% aqueous solution
4-01-00-03625 (Beilstein Handbook Reference) [Beilstein]
Acetal
Biformal
Biformyl
DIFORMYL
EDO
ethane-1,2-dial
ethane-1,2-dione
Gelifundol
Glyoxal (40per cent w/w in H2O)
glyoxal aldehyde
Glyoxal, 40% in water
Glyoxal, 40% solution in water
Glyoxylaldehyde
GXT
ODIX
oxal
Oxaldehyde
oxaldehyde（库存处理）
Protectol GL 40 [Trade name]
STR01281
trans-glyoxal
UNII:50NP6JJ975
乙二醛 [Chinese]
Natural sources
There are several natural sources of glyoxal.
Thus, glyoxal can be produced biologically as a useful byproduct (i.e., for the generation of hydrogen peroxide required by manganese-dependent peroxidase enzymes;Kersten, 1990) or non-enzymatically by autoxidation of lipids (Hirayama et al., 1984).
Furthermore, it can be produced from a range of abiotic reactions with aromatic compounds in the presence of ozone and/or hydroxyl radicals.
Accordingly, Mopper & Stahovec (1986) detected the formation of glyoxal from humic acids by photochemical reactions in seawater.
Mopper et al.(1991) estimated the photochemical glyoxal formation rates in Sargasso seawater (0–4000 m) to be in the range of 0.4–1.1 nmol carbon/h.
In addition, one can safely assume that natural fires — in analogy with results reported for domestic and residential log fires (Kleindienst et al., 1986; McDonald et al., 2000) — will release glyoxal in addition to other aldehydes.
Ozone can — for example, when applied as a water disinfectant — catalyse the formation of glyoxal from organic carbon present in water (Glaze et al., 1989; Le Lacheur et al., 1991; Lopez et al., 1999)