4170-30-3 Usage
Description
CROTONALDEHYDE is a clear, colorless to straw-colored liquid with a strong suffocating odor. It is highly flammable and produces toxic vapors at room temperature. It is found naturally in emissions of some vegetation and volcanoes, and many foods contain it in small amounts. It is an important environmental pollutant formed during combustion of carbon-containing fuels and other materials.
Uses
Used in Chemical Industry:
CROTONALDEHYDE is used as an important industrial chemical for the synthesis of tocopherol (vitamin E), the food preservative sorbic acid, and the solvent 3-methylbutanol.
Used in Organic Synthesis:
CROTONALDEHYDE is used as an intermediate in the production of butyl alcohol, butyraldehyde, methoxybutyraldehyde, sorbic acid, maleic acid, crotonic acid, and crotyl alcohol.
Used in Polymer Chemistry:
CROTONALDEHYDE is used as a manufacturing agent for resins and polyvinyl acetals, a solvent for polyvinyl chloride, and a rubber antioxidant that increases rubber strength with ketones.
Used in Agriculture:
CROTONALDEHYDE is used in the preparation of insecticides and fertilizers.
Used in Flavor Production:
CROTONALDEHYDE is used in the production of flavors.
Used as a Warning Agent:
CROTONALDEHYDE is used as a warning agent in fuel gases due to its strong suffocating odor.
Used in the Production of Scorbic Acid:
CROTONALDEHYDE is used as an intermediate for the production of scorbic acid.
Used in the Manufacture of n-Butyl Alcohol:
CROTONALDEHYDE was formerly used in the manufacture of n-butyl alcohol.
Used in the Formation of Emissions:
CROTONALDEHYDE is formed during the combustion of fossil fuels.
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.
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.
Source
Reported in gasoline-powered automobile exhaust at concentrations ranging from 100 to
900 ppb (quoted, Verschueren, 1983).
Gas-phase tailpipe emission rates from California Phase II reformulated gasoline-powered
automobiles with and without catalytic converters were 1.17 and 114 mg/km, respectively
(Schauer et al., 2002).
Schauer et al. (2001) measured organic compound emission rates for volatile organic
compounds, gas-phase semi-volatile organic compounds, and particle phase organic compounds
from the residential (fireplace) combustion of pine, oak, and eucalyptus. The gas-phase emission
rates of crotonaldehyde were 276 mg/kg of pine burned, 177 mg/kg of oak burned, and 198 mg/kg
of eucalyptus burned.
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).
Toxicity evaluation
Crotonaldehyde (steric form not reported) has been identified
as a volatile emission product from the arboreous plant
Chinese arborvitae. It has also been detected in gases emitted
from volcanoes. (E)-Crotonaldehyde is emitted to the atmosphere
from the combustion of wood and in exhaust from
gasoline and diesel engines. It is also released to the environment
from tobacco smoke, polymer combustion, and turbine
exhaust.
(E)-Crotonaldehyde has been detected in drinking water
and wastewater, and in human milk and expired air. If released
to soil, (E)-crotonaldehyde will have very high mobility.
Volatilization of (E)-crotonaldehyde may be important from
moist and dry soil surfaces. Biodegradation studies suggest that
(E)-crotonaldehyde may be biodegradable in soil and water,
especially in anaerobic conditions. (E)-Crotonaldehyde readily
polymerizes; therefore, if it is released to soil or water in a spill
situation, a significant fraction may polymerize. If released to
water, (E)-crotonaldehyde may not adsorb to suspended solids
and sediment.
Check Digit Verification of cas no
The CAS Registry Mumber 4170-30-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,1,7 and 0 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 4170-30:
(6*4)+(5*1)+(4*7)+(3*0)+(2*3)+(1*0)=63
63 % 10 = 3
So 4170-30-3 is a valid CAS Registry Number.
InChI:InChI=1/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2-
4170-30-3Relevant articles and documents
Dual Role of the Rhodium(III) Catalyst in C-H Activation: [4 + 3] Annulation of Amide with Allylic Alcohols to 7-Membered Lactams
Sherikar, Mahadev Sharanappa,Devarajappa, Ravi,Prabhu, Kandikere Ramaiah
supporting information, p. 4625 - 4637 (2021/04/06)
[4 + 3] annulation of primary and secondary benzamide and cinnamamide derivatives using allyl alcohol as a coupling partner catalyzed by Rh(III) is reported, where Rh(III) is playing a dual role of an oxidant and a catalyst for C-H activation. The Rh-catalyst oxidizes allyl alcohol to its carbonyl derivative, and the in situ-generated carbonyl compound reacts with benzamide in the presence of the Rh-catalyst, forming the corresponding alkylated products. Mechanistic studies show that AgSbF6 is also playing a dual role. Apart from being a halide scavenger, AgSbF6 catalyzes the cyclization of the alkylated product, forming the desired lactam. The current method has good synthetic application and is useful for synthesizing a few biologically active compounds that can act as the dopamine D3 receptor ligand, including berberine-like analogues. The deuteration study and control experiments helped us to propose the mechanism.
Rapid, chemoselective and mild oxidation protocol for alcohols and ethers with recyclable N-chloro-N-(phenylsulfonyl)benzenesulfonamide
Badani, Purav,Chaturbhuj, Ganesh,Ganwir, Prerna,Misal, Balu,Palav, Amey
supporting information, (2021/06/03)
Chlorine is the 20th most abundant element on the earth compared to bromine, iodine, and fluorine, a sulfonimide reagent, N-chloro-N-(phenylsulfonyl)benzenesulfonamide (NCBSI) was identified as a mild and selective oxidant. Without activation, the reagent was proved to oxidize primary and secondary alcohols as well as their symmetrical and mixed ethers to corresponding aldehydes and ketones. With recoverable PS-TEMPO catalyst, selective oxidation over chlorination of primary and secondary alcohols and their ethers with electron-donating substituents was achieved. The reagent precursor of NCBSI was recovered quantitatively and can be reused for synthesizing NCBSI.
A study on the cataluminescence of propylene oxide on FeNi layered double hydroxides/graphene oxide
Li, Ming,Hu, Yufei,Li, Gongke
, p. 11823 - 11830 (2021/07/11)
In this work, FeNi layered double hydroxides/graphene oxide (FeNi LDH/GO) was prepared, which exhibits excellent selective cataluminescent performance towards propylene oxide. The selectivity and sensitivity of the cataluminescence (CTL) reaction were investigated in detail. Moreover, the catalytic reaction mechanism, including the intermediate products and the conversion of reactants to products, was discussed based on both the experimental and computational results. Furthermore, the proposed FeNi LDH/GO based CTL sensor was successfully applied for the determination of propylene oxide residue in fumigated raisins, which indicates extensive application potential for rapid food safety evaluation.