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CAS Number: 107-22-2
European Community (EC) Number: 203-474-9
Molecular Formula: C2H2O2
Names:
IUPAC names: Oxaldehyde
Preferred IUPAC name: Ethanedial
Other names:
• Glyoxal
• Glyoxaldehyde
• Oxalaldehyde
• Ethanedialdehyde
DESCRIPTION:
Oxalaldehyde is an organic compound with the chemical formula OCHCHO.
Oxalaldehyde is the smallest dialdehyde (a compound with two aldehyde groups).
Oxalaldehyde 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.
Pure Oxalaldehyde is not commonly encountered because Oxalaldehyde is usually handled as a 40% aqueous solution (density near 1.24 g/mL).
Oxalaldehyde forms a series of hydrates, including oligomers.
For many purposes, these hydrated oligomers behave equivalently to Oxalaldehyde.
Oxalaldehyde is produced industrially as a precursor to many products.
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.
Oxalaldehyde is the dialdehyde that is the smallest possible and which consists of ethane having oxo groups on both carbons.
Oxalaldehyde has a role as a pesticide, an agrochemical, an allergen and a plant growth regulator.
Oxalaldehyde is a natural product found in Sesamum indicum with data available.
Oxalaldehyde 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).
Oxalaldehyde is an organic compound with the formula OCHCHO.
Oxalaldehyde is a yellow-colored liquid that evaporates to give a green-colored gas.
Oxalaldehyde is the smallest dialdehyde (two aldehyde groups).
Its structure is more complicated than typically represented because the molecule hydrates and oligomerizes.
Oxalaldehyde is produced industrially as a precursor to many products.
CAS Number: 107-22-2
European Community (EC) Number: 203-474-9
Molecular Formula: C2H2O2
FUNCTION OF OXALALDEHYDE:
Coated paper and textile finishes use large amounts of glyoxal as a crosslinker for starch-based formulations.
Oxalaldehyde condenses with urea to afford 4,5-dihydroxy-2-imidazolidinone, which further reacts with formaldehyde to give the bis(hydroxymethyl) derivative used for wrinkle-resistant chemical treatments.
PROPERTIES OF OXALALDEHYDE:
Chemical formula: C2H2O2
Molar mass: 58.036 g•mol−1
Melting point: 15 °C (59 °F; 288 K)
Boiling point: 51 °C (124 °F; 324 K)
Heat capacity (C): 1.044 J/(K•g)
Flash point: −4 °C (25 °F; 269 K)
Autoignition temperature: 285 °C (545 °F; 558 K)
Molecular Weight: 58.04
XLogP3-AA: -0.4
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 1
Exact Mass: 58.005479302
Monoisotopic Mass: 58.005479302
Topological Polar Surface Area: 34.1 Ų
Heavy Atom Count: 4
Formal Charge: 0
Complexity: 25
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Origin: Synthetic
Shelf life: 6 months from mfg. date
Freight Classification: NMFC 43940 SUB 2 CLASS 85
Kosher Status: Not Kosher
Flash Point: -4 ℃ (25 øF)
Melting Point: 15 ℃ (59 øF)
API: NO
Allergen: NO
Hazmat: YES
Molecular Weight: 58.04 g/mol
APPEARANCE:
Pale yellow to colorless liquid
STORAGE:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature 2 - 8 ℃.
CAS Number: 107-22-2
European Community (EC) Number: 203-474-9
Molecular Formula: C2H2O2
PRODUCTION OF OXALALDEHYDE:
Oxalaldehyde was first prepared and named by the German-British chemist Heinrich Debus (1824–1915) by reacting ethanol with nitric acid.
Commercial Oxalaldehyde 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 Oxalaldehyde 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 Oxalaldehyde is made and reported as a 40% solution in water by weight (approx. 1:5 molar ratio of Oxalaldehyde to water).
LABORATORY METHODS OF OXALALDEHYDE:
Oxalaldehyde may be synthesized in the laboratory by oxidation of acetaldehyde with selenious acid or by ozonolysis of benzene.
Anhydrous Oxalaldehyde is prepared by heating solid glyoxal hydrate(s) with phosphorus pentoxide and condensing the vapors in a cold trap
BIOCHEMISTRY OF OXALALDEHYDE:
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 OF OXALALDEHYDE:
Coated paper and textile finishes use large amounts of Oxalaldehyde 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.
Oxalaldehyde is used as a solubilizer and cross-linking agent in polymer chemistry.
Oxalaldehyde 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.
Oxalaldehyde is commercially available.
Oxalaldehyde solutions can also be used as a fixative for histology, that is, a method of preserving cells for examining them under a microscope.
CAS Number: 107-22-2
European Community (EC) Number: 203-474-9
Molecular Formula: C2H2O2
Speciation in solution:
Oxalaldehyde 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 Oxalaldehyde 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.
SAFETY INFORMATION ABOUT OXALALDEHYDE:
First aid measures:
Description of first aid measures:
General advice : Take off all contaminated clothing immediately.
If inhaled : If breathed in, move person into fresh air.
If symptoms persist, call a physician.
In case of skin contact : In case of contact, immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Call a physician immediately.
In case of eye contact : Rinse immediately with plenty of water, also under the eyelids, for at least 15 minutes.
Call a physician immediately.
If swallowed : Do NOT induce vomiting.
Rinse mouth with water.
Give small amounts of water to drink.
Obtain medical attention.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media : Water
Dry powder:
Foam
Carbon dioxide (CO2)
Special hazards arising from the substance or mixture:
Advice for firefighters:
Further information : Standard procedure for chemical fires.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Personal precautions : Use personal protective equipment.
Environmental precautions:
Environmental precautions : Do not flush into surface water or sanitary sewer system.
Avoid subsoil penetration.
Methods and material for containment and cleaning up:
Methods for cleaning up : Wipe up with absorbent material (e.g. cloth, fleece).
Soak up with inert absorbent material (e.g. sand, silica gel, acid binder, universal binder, sawdust)
Handling and storage:
Precautions for safe handling:
Advice on safe handling : Handle and open container with care.
Advice on protection against fire and explosion: No special protective measures against fire required.
Hygiene measures : Take off all contaminated clothing immediately.
Conditions for safe storage, including any incompatibilities:
Requirements for storage areas and containers: Store in original container.
Further information on storage conditions: Keep away from heat. Keep away from direct sunlight. Keep container tightly closed.
Advice on common storage : Keep away from food and drink.
Exposure controls/personal protection:
Control parameters:
Contains no substances with occupational exposure limit values.
Exposure controls:
Personal protective equipment:
Eye protection : Safety glasses with side-shields
Hand protection : Impervious glovesSplash protection: disposable nitrile rubber gloves e.g. Dermatril (layer thickness: 0.11 mm) made by KCL or gloves from other manufacturers offering the same protection.
Prolonged contact: Butyl rubber gloves e.g. Butoject (>480 Min., layer thickness: 0.70 mm) made by KCL or gloves from other manufacturers offering the same protection.
Skin and body protection : Body protection must be chosen depending on activity and possible exposure, e.g. apron, protecting boots, chemicalprotection suit ( according to EN 14605 in case of splashes or EN ISO 13982 in case of dust).
Respiratory protection : In case of mist, spray or aerosol exposure wear suitable personal respiratory protection and protective suit.
Protective measures : Avoid contact with skin and eyes.
CAS Number: 107-22-2
European Community (EC) Number: 203-474-9
Molecular Formula: C2H2O2
SYNONYMS OF OXALALDEHYDE:
MeSH Entry Terms:
Ethanedial
Ethanedione
Glyoxal
Depositor-Supplied Synonyms:
GLYOXAL
Ethanedial
107-22-2
Oxalaldehyde
oxaldehyde
1,2-Ethanedione
Glyoxylaldehyde
Biformal
Biformyl
Diformal
Diformyl
Oxal
Aerotex glyoxal 40
Glyoxal aldehyde
Ethanedial, trimer
Ethanediol, trimer
DTXSID5025364
CHEBI:34779
Glyoxal, 40% solution in water
50NP6JJ975
NCGC00091228-01
DSSTox_CID_5364
DSSTox_RID_77764
DSSTox_GSID_25364
Glyoxal, 40%
Ethanedione
Glyoxal solutions
CAS-107-22-2
CCRIS 952
Ethane-1,2-dione
ODIX
C2H2O2
HSDB 497
Glyoxal solution, ~40% in H2O (~8.8 M)
Glyoxal, 29.2%
EINECS 203-474-9
Glyoxal, 40% in water
BRN 1732463
hydroxyketene
Ethandial
Glycoxal
ethane dial
UNII-50NP6JJ975
AI3-24108
(oxo)acetaldehyde
ethane-1,2-dial
Protectol GL 40
glyoxal (ethanedial)
MFCD00006957
oxalic acid dihydride
hydroxymethylene ketone
NSC 262684
Glyoxal, 40 % Solution
EC 203-474-9
Glyoxal solution, 40.0%
4-01-00-03625 (Beilstein Handbook Reference)
BIDD:ER0284
(CHO)2
Glyoxal, Biformyl, Oxalaldehyde
CHEMBL1606435
Glyoxal, 40% w/w aq. soln.
STR01281
ZINC8437750
Tox21_111105
Tox21_202517
BBL011519
NSC262684
STL146635
AKOS000119169
Glyoxal solution, 40 wt. % in H2O
NSC-262684
NCGC00260066-01
Glyoxal solution, CP, 40 wt. % in H2O
FT-0626792
G0152
Q413465
J-001740
F2191-0152
Glyoxal solution, ~40% in H2O, for HPLC derivatization
Glyoxal solution, BioReagent, for molecular biology, ~40% in H2O (~8.8 M)
