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107-22-2

Basic Information
CAS No.: 107-22-2
Name: 1,2-Ethanedione
Molecular Structure:
Molecular Structure of 107-22-2 (1,2-Ethanedione)
Formula: C2H2O2
Molecular Weight: 58.0367
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%;
EINECS: 203-474-9
Density: 1.032 g/cm3
Melting Point: -14
Boiling Point: 50 °C at 760 mmHg
Flash Point: 104°C
Solubility: miscible with water
Appearance: white or off-white crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 20-36/38-43-68
Safety: 36/37
Transport Information: UN 1760
PSA: 34.14000
LogP: -0.61580
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Chemistry

Product Name: Glyoxal (CAS NO.107-22-2)

Molecular Formula: C2H2O2
Molecular Weight: 58.04g/mol
Mol File: 107-22-2.mol
EINECS: 203-474-9
Melting Point: -14 °C
Boiling point: 50 °C at 760 mmHg
Storage Temperature: 2-8°C
Density: 1.032 g/cm3
Refractive index:  n20/D 1.409
Water Solubility: miscible
Stability: Stability Combustible. Incompatible with strong oxidizing agents. Strong reducing agent. May polyermize exothermically. Incompatible with air, water, oxygen, peroxides, amides, amines, hydroxy-containing materials, nitric acid, aldehydes. Corrodes many metals.
Surface Tension: 28.2 dyne/cm
Enthalpy of Vaporization: 29.35 kJ/mol
Vapour Pressure: 292 mmHg at 25°C
XLogP3-AA: -0.4
H-Bond Donor: 0
H-Bond Acceptor: 2
Structure Descriptors of Glyoxal (CAS NO.107-22-2):
  IUPAC Name: oxaldehyde
  Canonical SMILES: C(=O)C=O
  InChI: InChI=1S/C2H2O2/c3-1-2-4/h1-2H 
  InChIKey: LEQAOMBKQFMDFZ-UHFFFAOYSA-N
Product Categories: Pharmaceutical Intermediates

Uses

Paper coatings and textiles use large amounts of glyoxal as a crosslinker for starch-based formulations and as a starting material with ureas for wrinkle-resistant chemical treatments. It is used as a solubilizer and cross-linking agent in polymer chemistry:
proteins (leather tanning process)
collagen
cellulose derivatives (textiles)
hydrocolloids
starch (paper coatings)
It 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.

Production

Commercial glyoxal is prepared either by the gas phase oxidation of ethylene glycol in the presence of a silver or copper catalyst or by the liquid phase oxidation of acetaldehyde with nitric acid. Global nameplate capacity is ~220,000 tons, with production rates less, due to over-capacity mostly in Asia. Most production is done via the gas phase oxidation route.
The first commercial glyoxal source was in Lamotte, France, started in 1960 and currently owned by Clariant. The single largest commercial source is BASF in Ludwigshafen, Germany at ~60,000 tons/annum. Only 2 production sites (Geismer, LA and Charlotte, NC) exist in the Americas. Significant recent capacity has been added in China. Commercial bulk glyoxal is made and reported as a 40%-strength solution.
Glyoxal is prepared in the lab by oxidation of acetaldehyde with selenious acid.
The preparation of anhydrous glyoxal entails heating solid glyoxal hydrate(s) with phosphorus pentoxide, as described in 1907 by Harries and Temme: "one heats the mixture of (crude) glyoxal and P4O10 with an open flame and soon observes that, upon blackening of the contents, a mobile green gas, which condenses in the cooled flask as beautiful yellow crystals)."

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 300uL/kg (0.3mL/kg)   National Technical Information Service. Vol. OTS0535072,
guinea pig LD50 oral 760mg/kg (760mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: OTHER CHANGES
Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 259, 1941.
guinea pig LD50 oral 10gm/kg (10000mg/kg)   National Technical Information Service. Vol. OTS0538086,
guinea pig LD50 skin 6600mg/kg (6600mg/kg)   "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 291, 1969.
mouse LD50 intraperitoneal 200mg/kg (200mg/kg)   National Technical Information Service. Vol. AD438-895,
mouse LD50 oral 400mg/kg (400mg/kg) BEHAVIORAL: MUSCLE WEAKNESS National Technical Information Service. Vol. OTS0533618,
mouse LD50 oral 1280mg/kg (1280mg/kg)   National Technical Information Service. Vol. OTS0538086,
rabbit LD50 intraperitoneal 60mg/kg (60mg/kg)   National Technical Information Service. Vol. OTS0535072,
rabbit LD50 intravenous 60mg/kg (60mg/kg)   National Technical Information Service. Vol. OTS0535072,
rabbit LD50 oral > 3175mg/kg (3175mg/kg)   National Technical Information Service. Vol. OTS0538086,
rabbit LD50 skin 10mL/kg (10mL/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

LIVER: OTHER CHANGES
National Technical Information Service. Vol. OTS0535072,
rabbit LD50 skin 10mL/kg (10mL/kg)   Union Carbide Data Sheet. Vol. 11/4/1971,
rabbit LD50 skin 10mL/kg (10mL/kg)   Union Carbide Data Sheet. Vol. 11/12/1965,
rat LC50 inhalation 2410mg/m3/4H (2410mg/m3) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
National Technical Information Service. Vol. OTS0535127,
rat LD50 oral 200mg/kg (200mg/kg) BEHAVIORAL: MUSCLE WEAKNESS National Technical Information Service. Vol. OTS0533618,
rat LD50 oral 2960mg/kg (2960mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
National Technical Information Service. Vol. OTS0535124,
rat LD50 oral 4290mg/kg (4290mg/kg)   Union Carbide Data Sheet. Vol. 11/4/1971,
rat LD50 skin > 2gm/kg (2000mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" National Technical Information Service. Vol. OTS0535506,
rat LDLo intraperitoneal 100mg/kg (100mg/kg)   National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 9, 1953.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Safety Information of Glyoxal (CAS NO.107-22-2):
Hazard Codes: XnHarmful
Risk Statements: 20-36/38-43-68  
R20:Harmful by inhalation. 
R36/38:Irritating to eyes and skin. 
R43:May cause sensitization by skin contact. 
R68:Possible risk of irreversible effects.
Safety Statements: 36/37
S36/37:Wear suitable protective clothing and gloves.
RIDADR: UN 1760
WGK Germany: 1
RTECS: MD2700000

Standards and Recommendations

ACGIH TLV: TWA 0.1 mg/m3 (sensitizer); Not Classifiable as a Human Carcinogen).

Specification

 Glyoxal , its CAS NO. is 107-22-2, the synonyms are 1,2-Ethanedione ; Aerotex glyoxal 40 ; Biformal ; Diformyl ; Ethanedial ; Glyoxylaldehyde ; Oxal ; Oxalaldehyde .