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CAS No.: | 107-22-2 |
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Name: | 1,2-Ethanedione |
Molecular Structure: | |
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: | Xn |
Risk Codes: | 20-36/38-43-68 |
Safety: | 36/37 |
Transport Information: | UN 1760 |
PSA: | 34.14000 |
LogP: | -0.61580 |
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
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.
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)."
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. |
Reported in EPA TSCA Inventory.
Safety Information of Glyoxal (CAS NO.107-22-2):
Hazard Codes: Xn
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
ACGIH TLV: TWA 0.1 mg/m3 (sensitizer); Not Classifiable as a Human Carcinogen).
Glyoxal , its CAS NO. is 107-22-2, the synonyms are 1,2-Ethanedione ; Aerotex glyoxal 40 ; Biformal ; Diformyl ; Ethanedial ; Glyoxylaldehyde ; Oxal ; Oxalaldehyde .