Acrolein

Base Information

• Chemical Name: Acrolein
• CAS No.: 107-02-8
• Deprecated CAS: 25314-61-8,2360801-60-9
• Molecular Formula: C3H4O
• Molecular Weight: 56.0642
• Hs Code.: 29121900
• European Community (EC) Number: 203-453-4
• ICSC Number: 0090
• NSC Number: 8819
• UN Number: 1092
• UNII: 7864XYD3JJ
• DSSTox Substance ID: DTXSID5020023,DTXSID50526220
• Nikkaji Number: J4.045B,J831.299K
• Wikipedia: Acrolein
• Wikidata: Q342790
• Pharos Ligand ID: Z3ZG1TV59ZXX
• Metabolomics Workbench ID: 50052
• ChEMBL ID: CHEMBL721
• Mol file: 107-02-8.mol

Synonyms:2 Propenal;2-Propenal;Acraldehyde;Acrolein;Acrylaldehyde;Acrylic Aldehyde;Aldehyde, Acrylic;Aldehyde, Allyl;Aldehyde, Ethylene;Allyl Aldehyde;Aqualin;Ethylene Aldehyde

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Chemical Property of Acrolein

Chemical Property:

• Appearance/Colour: colourless to slightly yellow liquid
• Vapor Pressure: 4.05 psi ( 20 °C)
• Melting Point: -87 °C(lit.)
• Refractive Index: n20/D 1.403(lit.)
• Boiling Point: 52.8 °C at 760 mmHg
• Flash Point: -2 °F
• PSA: 17.07000
• Density: 0.795 g/cm³
• LogP: 0.37130
• Storage Temp.: 2-8°C
• Sensitive.: Air & Light Sensitive
• Solubility.: H2O: soluble2 to 3 parts
• Water Solubility.: Soluble. 21.25 g/100 mL
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 56.026214747
• Heavy Atom Count: 4
• Complexity: 30.3
• Transport DOT Label: Poison Inhalation Hazard Flammable Liquid

Purity/Quality:

Safty Information:

• Pictogram(s): F,T+,N,T
• Hazard Codes: F,T+,N,T
• Statements: 11-24/25-26-34-50-26/28-24
• Safety Statements: 23-26-28-36/37/39-45-61-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Other Toxic Gases & Vapors
• Canonical SMILES: C=CC=O
• Inhalation Risk: A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: Lachrymation. The substance is severely irritating to the eyes, skin and respiratory tract. Inhalation of high concentrations may cause lung oedema. The effects may be delayed. Medical observation is indicated.
• Uses: Acrolein (acraldehyde, acrylaldehyde, acrylic aldehyde, allyl aldehyde, propenal, 2-propenal) is another important aldehyde. It is used as a chemical intermediate in many industrial synthetic processes, including in the production of acrylic acid and allyl alcohol. Acrolein may also be used as a biocide and in the production of perfumes and colloidal metals. Residue from industrial emissions and the burning of wood and other organic substrates will contain traces of acrolein. Acrolein is also a constituent of diesel exhaust and photochemical smog. It is also formed during the pyrolysis of cotton and polyethylene and found in cigarette smoke. Much of the human toxicity data is obtained from the formation of acrolein in vivo as a metabolite of the anticancer drug, cyclophosphamide. Acrolein is used as an antimicrobial agentto prevent the growth of microbes againstplugging and corrosion, to control the aquaticweed and algae, in slime control in papermanufacturing, as a tissue fixative, and inleather tanning.Because of its widespread use it occursin the environment—in air and water. Afterformaldehyde it is the second most abundantaldehyde, constituting 5% of total aldehydesin air. Acrolein is one of the toxic gasesproduced in a wood or building fire or whenpolyethylene or other polymer substancesburn (Morikawa 1988; Morikawa and Yanai1986). Firefighters are at greater risk ofexposure to this gas. Acrolein is used in the etherification of food starch up to 0.6% and for the esterification and etherification of food starch up to 0.3% with vinyl acetate up to 7.5%. Acrolein is used in the synthesis of acrylic acid. manufacture of colloidal forms of metals; making plastics, perfumes; warning agent in methyl chloride refrigerant. Has been used in military poison gas mixtures. Used in organic syntheses. Aquatic herbicide. Contact herbicide and algicide; injected in water for the control of submerged and floating weeds in irrigation ditches and canals
• Description: The first time that acrolein was produced as a commercial product was in the 1930s through the vapor-phase condensation of acetaldehyde and formaldehyde. Another method was developed in the 1940s, which involved the vapor-phase oxidation of propylene. In the 1960s, some advances were found in propylene oxidation process by the introduction of bismuth molybdate-based catalysis, and that became the primary method used for the commercial production of acrolein. Some bioproducts formed for this reaction are acrylic acid, carbon oxides, acetaldehyde, acetic acid, formaldehyde, and polyacrolein. In World War I, it was used as a chemical weapon (pulmonary irritant and lachrymatory agent). Commercial acrolein contains 95.5% or more of the compound, the main impurities being water (<3.0% by weight) and other carbonyl compounds (<1.5% by weight), mainly propanol and acetone. Hydroquinone is added as an inhibitor of polymerization (0.1–0.25% by weight).
• Physical properties: Colorless to yellow, clear, watery liquid imparting a very sharp, acrid, pungent, or irritating odor. Odor threshold concentrations reported were 0.11 mg/kg by Guadagni et al. (1963), 0.21 ppmv by Leonardos et al. (1969), and 36 ppbv by Nagata and Takeuchi (1990). In addition, Katz and Talbert (1930) reported an experimental detection odor threshold concentration of 4.1 mg/m3 (1.8 ppmv).

Technology Process of Acrolein

There total 685 articles about Acrolein which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 1.0%

buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) → acrolein (107-02-8,25068-14-8) + 3-Cyclohexene-1-carboxaldehyde (100-50-5,61746-36-9)

Guidance literature:

With oxygen; bis(ethylene)rhodium acetylacetonate; In toluene; at 80 ℃; for 1h; under 37503 Torr;

DOI:10.1002/hlca.19830660119

Reference yield:

bromine (7726-95-6) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → hydrogen bromide (10035-10-6,12258-64-9) + bromoacetic acid (79-08-3) + acrolein (107-02-8,25068-14-8)

Guidance literature:

at 100 ℃;

Reference yield:

polytrimethylene terephthalate → terephthalic acid (100-21-0) + acrolein (107-02-8,25068-14-8)

Guidance literature:

With sulfuric acid; In water; pH=1.3;

upstream raw materials:

(2E,4E)-hexa-2,4-diene

3-chloroprop-1-ene

propene

Tetrahydrofurfuryl alcohol

Downstream raw materials:

2-(N-pyrrolidinyl)bicyclo<3.2.1>octan-8-one

2-(Pyrrolidin-1-yl)bicyclo[3.3.1]nonan-9-on

1,3-butadiene-1-carboxylic acid

4-acetyl-5-oxo-hexanal

Refernces

Mild rhodium(III)-catalyzed cyclization of amides with α,β- unsaturated aldehydes and ketones to azepinones: Application to the synthesis of the homoprotoberberine framework

10.1002/anie.201301426

The key substrate used in this study, N-methoxybenzamide (1a), is an amide with a methoxy group attached to the nitrogen atom. It is key for the initial reaction with a,b-unsaturated aldehydes and ketones. Another amide substrate used in this study, N-methylbenzamide (1b), has a methyl group attached to the nitrogen atom, which affects the reactivity and selectivity of the C-H activation process. N-n-butylbenzamide (1c), an amide with a butyl group attached to the nitrogen atom, demonstrates the versatility of the method towards different alkyl groups. N-benzylbenzamide (1d), an amide with a benzyl group attached to the nitrogen atom, is used to demonstrate the tolerance of the reaction towards aromatic groups. Acrolein (2a), the simplest unsaturated aldehyde used in this study, acts as the electrophilic component in the cyclization process and reacts with the amide to generate the desired azacyclopentane product.

REACTIVITE DES DERIVES ORGANOCUIVREUX VIS-A-VIS DES ALDEHYDES αβ-ETHYLENIQUES

10.1016/S0040-4020(01)92455-X

The research focuses on the reactivity of secondary lithium dialkylcuprates with α,β-ethylenic aldehydes, exploring the formation of 1,2 and 1,4 addition products. The study aims to understand the influence of the cuprate's metal component (magnesium or lithium) and the structure of the aldehydes on the reaction outcomes. The conclusions drawn from the research indicate that secondary alkyl cuprates yield a mixture of 1,2 and 1,4 addition products, while allylic or acetylenic cuprates predominantly yield 1,2 addition products. In contrast, homoallylic, vinylic, and phenyl cuprates exclusively give 1,4 addition products. The research also highlights that chloromagnesium dimethyl cuprate in THF is the most favorable for 1,4 addition. Key chemicals used in the process include various organocuprates and organocopper reagents, such as dialkylcuprates of lithium, methylcopper, and dimethylcuprate of chloromagnesium, as well as α,β-ethylenic aldehydes like acrolein, crotonaldehyde, and methyl-2-pentene-2-al.

10.1021/jo00805a002

The study investigates the reactions of 2-diazoacenaphthenone (1) with various olefins and acetylenes. The researchers found that 1 did not decompose in boiling benzene or toluene but underwent copper-catalyzed thermolysis in boiling toluene to form biacenedione. In boiling xylene, 1 produced biacenedione and a trace amount of acenaphthenequinone ketazine. When 1 reacted with olefins like ethyl acrylate, acrylonitrile, ethyl a-bromoacrylate, and methyl vinyl ketone in refluxing benzene, it yielded spiro[acenaphthenone-2,1'-cyclopropanes] (3a-d, 4a-c, 7) with two stereoisomers for some reactions. Reactions with acrolein, phenylacetylene, and diethyl acetylenedicarboxylate led to the formation of 2'-hydroxymethylspiro[acenaphthenone-2,1'-cyclopropanes] (5, 6) and spiro[acenaphthenone-2,3'(3'H)-pyrazoles] (9, 10). The study also explored the reaction of 1 with bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride, producing spiro[acenaphthenone-2,3'-tricyclooctanedicarboxylic anhydride] (8). The researchers used various analytical techniques to confirm the structures and properties of the synthesized compounds.