CROTONALDEHYDE
- CAS No.
- 4170-30-3
- Chemical Name:
- CROTONALDEHYDE
- Synonyms
- 2-BUTENAL;BUTENAL;but-2-enal;Crotonaldehyd;2-CROTONALDEHYDE;buten-2-al;2-BUTEN-1-AL;Krotonaldehyd;methylpropenal;CROTINALDEHYDE
- CBNumber:
- CB6733702
- Molecular Formula:
- C4H6O
- Molecular Weight:
- 70.09
- MOL File:
- 4170-30-3.mol
- Modify Date:
- 2024/3/14 15:18:27
| Melting point | −76 °C(lit.) |
|---|---|
| Boiling point | 104 °C(lit.) |
| Density | 0.853 g/mL at 20 °C(lit.) |
| vapor density | 2.41 (vs air) |
| vapor pressure | 32 mm Hg ( 20 °C) |
| refractive index |
n |
| Flash point | 48 °F |
| storage temp. | 2-8°C |
| solubility | Miscible with alcohol, benzene, gasoline, kerosene, solvent naphtha, and toluene (Hawley, 1981) |
| form | Colorless liquid |
| color | Colourless |
| Odor Threshold | 0.023ppm |
| Water Solubility | Soluble in water. (150g/L) at 20°C. |
| Sensitive | Air Sensitive |
| Merck | 13,2624 |
| BRN | 1209254 |
| Henry's Law Constant | 1.92 x 10-5 atm?m3/mol (Buttery et al., 1971) |
| Exposure limits | NIOSH REL: TWA 2 ppm (6 mg/m3), IDLH 50 ppm; OSHA PEL: TWA 2 ppm; ACGIH TLV: ceiling 0.3 ppm (adopted). |
| Stability | Air sensitive. Highly flammable. Readily forms explosive mixtures with air. May polymerize in the presence of acids, alkalies or amines. Uncontrolled polymerisation may lead to a rapid temperature rise. Incompatible with acids, bases, amines, strong oxidizing agents, butadiene, ketones, oxygen. May contain a stabilizer. |
| LogP | 0.6 at 25℃ |
| CAS DataBase Reference | 4170-30-3(CAS DataBase Reference) |
| IARC | 3 (Vol. 63) 1995 |
| EPA Substance Registry System | Crotonaldehyde (4170-30-3) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |      GHS02,GHS05,GHS06,GHS08,GHS09 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H225-H301+H311-H315-H318-H330-H335-H341-H373-H400 | |||||||||
| Precautionary statements | P201-P210-P280-P301+P310+P330-P304+P340+P310-P305+P351+P338+P310 | |||||||||
| Hazard Codes | F,T+,N | |||||||||
| Risk Statements | 11-24/25-26-37/38-41-48/22-50-68 | |||||||||
| Safety Statements | 26-28-36/37/39-45-61-16 | |||||||||
| RIDADR | UN 1143 6.1/PG 1 | |||||||||
| OEB | B | |||||||||
| OEL | TWA: 2 ppm (6 mg/m3) (Aldehydes) | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | GP9625000 | |||||||||
| F | 9-13-23 | |||||||||
| TSCA | Yes | |||||||||
| HazardClass | 6.1(a) | |||||||||
| PackingGroup | I | |||||||||
| Toxicity | LD50 orally in rats: 0.3 g/kg (Smyth, Carpenter) | |||||||||
| IDLA | 50 ppm | |||||||||
| NFPA 704 |
|
CROTONALDEHYDE Chemical Properties,Uses,Production
Chemical Properties
Crotonaldehyde is water-white (turns paleyellow on contact with air) with an irritating, pungent, suffocating odor.
Physical properties
Clear, colorless to straw-colored liquid with a pungent, irritating, suffocating odor. An odor threshold concentration of 23 ppbv was reported by Nagata and Takeuchi (1990). Katz and Talbert (1930) reported experimental detection odor threshold concentrations ranged from 180 to 570 μg/m3 (63 to 200 ppbv).
Uses
Crotonaldehyde is used in organic synthesis, in the manufacture of butyl alcohol and butyraldehyde, and as a warning agent in fuel gases. It is also used in the manufacture of nbutanol and sorbic acid as well as in the production of flavoring agents, surface-active agents, textiles, and insecticidal compounds.
Definition
Commercial crotonaldehyde is the trans isomer.
General Description
A clear colorless to straw colored liquid with a penetrating pungent odor. Flash point 55°F. Density 7.1 lb / gal. Very toxic by inhalation. May polymerize with the release of heat under exposure to heat or contamination. If polymerization takes place inside a container, the container may rupture violently. Less dense than water. Vapors heavier than air.
Air & Water Reactions
Highly flammable. Slightly soluble in water.
Reactivity Profile
CROTONALDEHYDE can react violently with strong oxidizing reagents, e.g., reaction with conc. nitric acid leads to instantaneous ignition [Andrussow, L., Chim. Ind. (Paris), 1961, 86, p. 542]. In contact with strong acids or bases CROTONALDEHYDE will undergo an exothermic condensation reaction. Reaction with 1,3-butadiene is particularly violent [Greenlee, K. W., Chem. Eng. News, 1948, 26, p. 1985]. Crotonaldehyde may rapidly polymerize with ethyl acetoacetate (Soriano, D.S. et al. 1988. Journal of Chemical Education 65:637.).
Hazard
An animal carcinogen. Irritating to eyes, skin, and upper respiratory tract irritant. Flammable, dangerous fire risk. Explosive limits in air 2.9–15.5% by volume. Questionable carcinogen.
Health Hazard
CROTONALDEHYDE is an extreme eye, respiratory, and skin irritant and can cause corneal damage. A 15 minute exposure at 4.1 ppm is highly irritating to the nose and upper respiratory tract and causes tearing. Brief exposure at 45 ppm proved very disagreeable with prominent eye irritation.
Fire Hazard
Flammable/combustible material; may be ignited by heat, sparks or flames. Vapor may travel to a source of ignition and flash back. Container may explode in heat of fire. Vapor explosion and poison hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Readily converted by oxygen to hazardous peroxides and acids and is incompatible with caustics, ammonia, organic amines, mineral acids, and strong oxidizers. Readily resinifies to dimer when pure and slowly oxidizes to crotonic acid. Altered by light and air. Hazardous polymerization may occur. Polymerization may take place at high temperatures.
Safety Profile
Suspected carcinogen with experimental carcinogenic data. Poison by ingestion and inhalation. Mutation data reported. An eye, skin, and mucous membrane irritant. A lachrymating material that can cause corneal burns and is very dangerous to the eyes. Caution: Keep away from heat and open flame. Keep container closed. Use with adequate ventilation. Extremely irritating to eyes, slim, mucous membranes. When necessary, the lachrymatory effect of the vapors may be counteracted by ammonia fumes. Dangerous fire hazard when exposed to heat or flame; can react with oxidizing materials. To fight fire, use alcohol foam, CO2, dry chemical. Reacts violently with 1,3 butadlene. Violent hypergolic reaction with concentrated nitric acid. When heated to decomposition it emits acrid smoke and fumes. See also ALDEHYDES.
Potential Exposure
Crotonaldehyde is used as a warning agent in fuel gases and gas line leaks; as solvent; in Crotonaldehyde 935 chemical warfare; as an intermediate in the manufacture of n-butanol and crotonic and sorbic acids; in resin and rubber antioxidant manufacture; also used as a solvent in mineral oil purification; as an alcohol denaturant.
Carcinogenicity
Similar to acrolein, crotonaldehyde is suspected of having tumorigenic activity and of involvement in the metabolism of N-nitrosopyrrolidine . Nevertheless, it has been proven that crotonaldehyde does have a carcinogenic effect on rats. Indeed, crotonaldehyde and nitrosopyrrolidine (a metabolite of crotonaldehyde) induced neoplastic lesions in the liver, hepatocellular carcinomas, neoplastic nodules, and liver damage when administered orally to rats over long periods of time.
Environmental Fate
Biological. Heukelekian and Rand (1955) reported a 10-d BOD value of 1.30 g/g which is
56.8% of the ThOD value of 2.29 g/g.
Chemical/Physical. Slowly oxidizes in air forming crotonic acid (Windholz et al., 1983). At
elevated temperatures, crotonaldehyde may polymerize (NIOSH, 1997).
Crotonaldehyde undergoes addition of water across the CH=CH bond yielding 3-
hydroxybutanal (Kollig, 1995).
At an influent concentration of 1,000 mg/L, treatment with GAC resulted in effluent
concentration of 544 mg/L. The adsorbability of the carbon used was 92 mg/g carbon (Guisti et
al., 1974).
Shipping
UN1143 Crotonaldehyde or Crotonaldehyde, stabilized, Hazard class: 6.1; Labels: 6.1-Poison Inhalation Hazard, 3-Flammable liquid, Inhalation Hazard Zone B.
Incompatibilities
Vapors may form explosive mixture with air. A strong reducing agent. Readily converted by oxygen to peroxides and acids; heat or contact with alkalis and many other substances may cause polymerization. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, nonoxidizing mineral acids; ammonia, organic amines; aliphatic amines; aromatic amines; 1,3-butadiene, strong bases. Liquid attacks some plastics, rubber, and coatings
Waste Disposal
Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed. May be absorbed on vermiculite and burned in open incinerator or dissolved in solvent and sprayed into incinerator