Acrolein
[CAS# 107-02-8]

Identification

• Classification: Organic raw materials >> Aldehyde
• Name: Acrolein
• Synonyms: 2-Propen-1-one; 2-Propenal; Acrylaldehyde; Acrylic aldehyde
• Molecular Formula: C₃H₄O
• Molecular Weight: 56.06
• CAS Registry Number: 107-02-8
• EC Number: 203-453-4
• SMILES: C=CC=O

Properties

• Density: 0.8389
• Melting point: -87.7 °C
• Boiling point: 52.7 °C
• Refractive index: 1.402
• Flash point: -26 °C
• Water solubility: Soluble. 21.25 g/100 mL

Safety Data

• Hazard Symbols: GHS02;GHS06;GHS05;GHS09 Danger
• Risk Statements: H225-H330-H300-H311-H314-H400-H410
• Safety Statements: P210-P233-P240-P241-P242-P243-P260-P262-P264-P264+P265-P270-P271-P273-P280-P284-P301+P316-P301+P330+P331-P302+P352-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P317-P320-P321-P330-P361+P364-P363-P370+P378-P391-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	2	H225
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	1	H330
Acute toxicity	Acute Tox.	2	H300
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute toxicity	Acute Tox.	3	H301
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	2	H330
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Acute toxicity	Acute Tox.	2	H310
Skin corrosion	Skin Corr.	1A	H314
Specific target organ toxicity - single exposure	STOT SE	3	H335
Carcinogenicity	Carc.	2	H351

• Transport Information: UN 1092

Discovery and Applications

Acrolein, also known by its systematic name propenal, is a highly reactive unsaturated aldehyde with the molecular formula C₃H₄O. It was first identified in the 19th century by the decomposition of fats and glycerol, where it was noted for its strong, pungent odor. Acrolein’s reactivity, due to its conjugated carbonyl and alkene groups, has made it a valuable compound in industrial and chemical applications. Although acrolein was initially considered a byproduct, its unique properties have established it as a precursor for multiple synthetic pathways in modern chemistry.

Structurally, acrolein consists of a three-carbon chain with a double bond between the first and second carbons and an aldehyde group on the first carbon. This structure makes it highly electrophilic, reacting readily with nucleophiles, and susceptible to polymerization. These properties allow acrolein to be an effective intermediate in various synthesis processes, though its reactivity also necessitates careful handling. It is typically produced via the oxidation of propylene, a method that allows for large-scale production with controlled yields.

Acrolein is widely used in the synthesis of methionine, an essential amino acid in animal feed that supports growth and metabolism. In this application, acrolein’s reactivity enables it to form intermediates that are further processed into methionine, making it a vital component of the agricultural industry. Acrolein is also used as a biocide, particularly in water treatment systems, where its potent reactivity can eliminate bacteria, algae, and other organisms. This application is especially common in industrial water systems and oil extraction operations, where acrolein helps maintain system efficiency by preventing microbial growth.

In polymer chemistry, acrolein is a building block for numerous specialty polymers and resins. Through polymerization, acrolein forms polyacrolein, a material with applications in adhesives, coatings, and specialty packaging. Furthermore, acrolein derivatives are used in the production of plastics and synthetic fibers, where they impart desired structural properties. Despite its many applications, acrolein is known for its toxicity and environmental impact, necessitating stringent regulations and careful monitoring in its production and use.

The discovery and development of acrolein have contributed significantly to various fields, including agriculture, polymer science, and industrial water treatment. Its versatility and reactivity continue to drive its importance in chemical synthesis and industry, even as research focuses on safe and sustainable handling practices for this valuable compound.

References

1979. Cyclophosphamide cystitis--identification of acrolein as the causative agent. Biochemical Pharmacology.
DOI: 10.1016/0006-2952(79)90222-3

1979. Interactions of sulfur dioxide and acrolein as sensory irritants. Toxicology and Applied Pharmacology.
DOI: 10.1016/0041-008x(79)90037-1

1991. DNA sequence analysis of spontaneous and beta-methoxy-acrolein-induced mutations in Salmonella typhimurium hisD3052. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis.
DOI: 10.1016/0027-5107(91)90032-j