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Crotonaldehyde
Crotonaldehyde
Crotonaldehyde
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Crotonaldehyde[1]
Skeletal formula of crotonaldehyde
Ball-and-stick model of (Z)-crotonaldehyde
Names
IUPAC name
(2E)-but-2-enal
Other names
Crotonaldehyde
Crotonic aldehyde
β-Methacrolein
β-Methyl acrolein
2-butenal
Propylene aldehyde
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.021.846 Edit this at Wikidata
EC Number
  • 204-647-1
KEGG
RTECS number
  • GP9499000
UNII
UN number 1143
  • InChI=1S/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2+ checkY
    Key: MLUCVPSAIODCQM-NSCUHMNNSA-N checkY
  • InChI=1/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2+
    Key: MLUCVPSAIODCQM-NSCUHMNNBQ
  • O=C/C=C/C
Properties ((E) isomer)
C4H6O
Molar mass 70.091 g·mol−1
Appearance colourless liquid
Odor pungent, suffocating odor
Density 0.846 g/cm3
Melting point −76.5 °C (−105.7 °F; 196.7 K)
Boiling point 104.0 °C (219.2 °F; 377.1 K)
18% (20 °C)[2]
Solubility very soluble in ethanol, ethyl ether, acetone
soluble in chloroform
miscible in benzene
Vapor pressure 19 mmHg (20 °C)[2]
1.4362
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H225, H301, H310, H311, H315, H318, H330, H335, H341, H373, H400
P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P271, P273, P280, P281, P284, P301+P310, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P320, P321, P322, P330, P332+P313, P361, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
4
3
2
Flash point 13 °C (55 °F; 286 K)
207 °C (405 °F; 480 K)
Explosive limits 2.1–15.5%
Lethal dose or concentration (LD, LC):
600 ppm (rat, 30 min)
1375 ppm (rat, 30 min)
519 ppm (mouse, 2 hr)
1500 ppm (rat, 30 min)[3]
400 ppm (rat, 1 hr)[3]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 2 ppm (6 mg/m3)[2]
REL (Recommended)
 TWA 2 ppm (6 mg/m3)[2]
IDLH (Immediate danger)
 50 ppm[2]
Related compounds
Related alkenals
 Acrolein

cis-3-hexenal
(E,E)-2,4-Decadienal

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common. This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.[4]

Production and reactivity

[edit]

Crotonaldehyde is produced by the aldol condensation of acetaldehyde:

2 CH3CHO → CH3CH=CHCHO + H2O

Crotonaldehyde is a multifunctional molecule that exhibits diverse reactivity. It is a prochiral dienophile.[5] It is a Michael acceptor. Addition of methylmagnesium chloride produces 3-penten-2-ol.[6]

Uses

[edit]
Crotonylidene diurea is a specialty fertilizer.[7]

It is a precursor to many fine chemicals. A prominent industrial example is the crossed aldol condensation with diethyl ketone to give trimethylcyclohexenone, this can be easily converted to trimethylhydroquinone, which is a precursor to the vitamin E.[8] Other derivatives include crotonic acid, 3-methoxybutanol and the food preservative Sorbic acid. Condensation with two equivalents of urea gives a pyrimidine derivative that is employed as a controlled-release fertilizer. [4]

Safety

[edit]

Crotonaldehyde is a potent irritant even at the ppm levels. It is not very toxic, with an LD50 of 174 mg/kg (rats, oral).[4]

See also

[edit]

References

[edit]
[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Crotonaldehyde

View on Grokipedia
from Grokipedia
Crotonaldehyde is an α,β-unsaturated with the molecular formula C₄H₆O and the systematic name (2E)-but-2-enal, existing primarily as the trans in commercial forms; it appears as a clear, colorless to straw-colored liquid with a strong, suffocating and is highly flammable, producing toxic vapors even at . Its key physical properties include a of 104 °C, a of -76 °C, a density of 0.85 g/cm³ at 20 °C, and moderate water solubility of approximately 18 g/100 mL at 20 °C. Industrially, crotonaldehyde is produced mainly through the of followed by , or alternatively by the oxidation of 1,3-butadiene, with global production serving as a versatile intermediate in . Its primary applications include the manufacture of sorbic acid, a widely used and yeast/mold inhibitor in and ; it also serves as a precursor for n-butanol, rubber accelerators, tanning agents, dyes, pesticides, and pharmaceuticals, as well as a warning odorant in fuels and an alcohol denaturant. Naturally occurring in trace amounts in various foodstuffs such as , fruits, and , crotonaldehyde is also generated during incomplete processes, appearing in environmental sources like tobacco smoke, vehicle exhaust, wood smoke, and emissions from burning paper, cotton, or plastics. From a safety perspective, crotonaldehyde is highly reactive, prone to polymerization and peroxide formation upon exposure to air, heat, or light, and it reacts violently with strong oxidizers; occupational exposure limits include a permissible exposure limit (PEL) of 2 ppm (8-hour time-weighted average) set by OSHA. It poses significant health risks as a potent irritant to the eyes, skin, respiratory tract, and mucous membranes, with inhalation potentially causing pulmonary edema at high concentrations (e.g., LC₅₀ of 1,400 ppm for 30 minutes in rats); ingestion or dermal contact can lead to burns and systemic toxicity, with oral LD₅₀ values around 140–206 mg/kg in rodents. Regarding carcinogenicity, the International Agency for Research on Cancer (IARC) classifies crotonaldehyde as possibly carcinogenic to humans (Group 2B) based on strong mechanistic evidence from animal studies showing genotoxic effects and limited human data linking it to exposures in tobacco smoke and combustion byproducts, while the U.S. EPA considers it a possible human carcinogen (Group C). In the environment, it degrades relatively quickly in the atmosphere via reaction with hydroxyl radicals (half-life ~11 hours) or ozone (~15.5 days), but it can persist in water and soil under anaerobic conditions, contributing to contamination near industrial sites or waste disposal areas.

General information

Nomenclature and structure

Crotonaldehyde is the common name for the unsaturated with the molecular formula C₄H₆O and CH₃CH=CHCHO. This compound, also known as crotonic aldehyde, derives its name from , the corresponding , reflecting its historical association in . The IUPAC name is (2E)-but-2-enal for the trans (E) isomer, while the cis (Z) isomer is (2Z)-but-2-enal; commercially, crotonaldehyde is typically supplied as a containing over 95% E-isomer and less than 5% Z-isomer. Structurally, crotonaldehyde features an α,β-unsaturated moiety, where the of the is conjugated with a carbon-carbon , forming a π-system that extends across the . This conjugation enhances its reactivity and imparts prochiral dienophile characteristics, as the can participate in stereoselective cycloadditions while the adjacent chiral centers can be generated asymmetrically. The of crotonaldehyde is 70.091 g·mol⁻¹.

Physical properties

Crotonaldehyde is a clear, colorless to straw-colored liquid that turns pale yellow upon exposure to air and light. It has a pungent, suffocating odor. The compound has a of 0.853 g/cm³ at 20°C. Its is -76.5°C, and the is 104°C at 760 mmHg. Crotonaldehyde exhibits moderate in , approximately 18 g/100 mL at 20°C, and is miscible with organic solvents such as , , acetone, and . The is 30 mmHg at 20°C. Its is 1.437 at 20°C. Due to its conjugated structure, crotonaldehyde shows characteristic UV absorption above 290 nm.

Synthesis

Industrial production

Crotonaldehyde is primarily produced industrially via the of , involving the reaction of two molecules to form an aldol intermediate that subsequently to yield crotonaldehyde and water:
2CH3CHO→CH3CH=CHCHO+H2O2 \mathrm{CH_3CHO} \rightarrow \mathrm{CH_3CH=CHCHO} + \mathrm{H_2O}
This process is catalyzed by basic agents, such as dilute aqueous solutions, under controlled temperature and pressure conditions to favor the dehydration step. An alternative industrial method involves the direct oxidation of 1,3-butadiene using catalysts. Industrial production typically employs liquid-phase processes, where is fed into a reactor with the alkaline catalyst, followed by neutralization with acids like acetic acid to quench the reaction and facilitate separation. Gas-phase variants, utilizing solid catalysts such as Zr-β zeolites, have been developed to enhance selectivity, reduce generation, and enable continuous operation. These methods are often integrated with upstream manufacturing plants, which derive from the of in facilities, optimizing feedstock utilization and cost efficiency. Key producers include Celanese Corporation in the United States, alongside facilities in countries such as , , , and . In 2002, U.S. production was estimated at 450–4,500 tonnes. As of 2023, accounts for approximately 90% of global production capacity with 140,000 metric tons, implying a global capacity of around 155,000 metric tons. The crude reaction mixture undergoes purification primarily through to remove unreacted , water, and heavy byproducts, resulting in a commercial product with 90–99% purity, predominantly the (E)- (>95%) and minimal (Z)- (<5%); stabilizers like 0.1–0.2% butylated hydroxytoluene (BHT) are added to prevent polymerization. Economically, crotonaldehyde production benefits from its role as a versatile intermediate in integrated chemical complexes, but it also emerges as a byproduct in certain petrochemical operations, such as the acetylene-based synthesis of , where it forms via side reactions and requires management to minimize waste. This byproduct status influences process economics by necessitating efficient recovery or treatment strategies in larger-scale petrochemical refineries.

Laboratory methods

Crotonaldehyde was first isolated in the early 19th century through distillation of croton oil, marking its initial discovery as a natural product component. A common laboratory method for preparing crotonaldehyde involves the oxidation of (CH₃CH=CHCH₂OH), a primary allylic alcohol, using selective oxidizing agents that halt at the aldehyde stage. (PCC) in dichloromethane effectively converts crotyl alcohol to crotonaldehyde by forming a chromate ester intermediate, followed by elimination to yield the carbonyl compound, with typical reaction times of 1-2 hours at room temperature. (MnO₂), particularly activated forms, is another mild reagent suitable for allylic alcohols, often employed in neutral solvents like petroleum ether or dichloromethane under reflux, leveraging its specificity for benzylic and allylic systems to avoid over-oxidation. These oxidations typically afford yields of 70-90%, with stereoselectivity favoring the E-isomer when starting from trans-, as the double bond geometry is preserved during the transformation. An alternative laboratory route is the partial hydrogenation of acrolein derivatives or other α,β-unsaturated aldehydes, where controlled addition of hydrogen targets specific double bonds while maintaining the conjugated system, though this method is less routine for small-scale synthesis due to selectivity challenges. The dehydration of the aldol condensation product from provides a versatile small-scale synthesis without industrial-scale optimizations like continuous flow. undergoes base-catalyzed self-condensation to form 3-hydroxybutanal, which readily dehydrates under mildly acidic or thermal conditions to ; for instance, using dilute sodium hydroxide at room temperature followed by acid-catalyzed dehydration yields the product with 70-90% efficiency. This process exhibits high stereoselectivity for the E-isomer, often exceeding 80% due to thermodynamic stability of the trans configuration during dehydration.

Chemical reactivity

Key reactions

Crotonaldehyde, as an α,β-unsaturated aldehyde, exhibits versatile reactivity stemming from its conjugated system, which activates both the carbonyl group and the alkene for nucleophilic attack, cycloadditions, and redox transformations. In Michael additions, crotonaldehyde serves as an acceptor, where nucleophiles add to the β-carbon in a 1,4-conjugate fashion, followed by protonation to yield the saturated aldehyde. For instance, thiols undergo efficient addition under solvent-free or ionic liquid conditions, forming β-thio aldehydes useful in synthesis. Similarly, amines add to produce β-amino aldehydes, often catalyzed for stereoselectivity in asymmetric variants. Crotonaldehyde acts as a dienophile in Diels-Alder cycloadditions, reacting with dienes such as cyclopentadiene to form bicyclic adducts like 3-methylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde, typically under thermal conditions without catalysts due to its electron-deficient alkene. This [4+2] reaction proceeds with endo selectivity in many cases, enabling access to cyclohexene derivatives for natural product synthesis. The aldehyde functionality undergoes standard reductions and oxidations. Selective reduction with NaBH₄ in methanol at 0°C predominantly delivers the allylic alcohol crotyl alcohol via 1,2-addition to the carbonyl, achieving 92% selectivity over the 1,4-saturated product. Oxidation with molecular oxygen, often using metal catalysts in continuous flow, converts crotonaldehyde to crotonic acid in yields up to 58% at 70% conversion, preserving the alkene. Grignard reagents add to the carbonyl of crotonaldehyde in a 1,2-manner, exemplified by the reaction with methylmagnesium chloride in ether at 0°C, yielding 3-penten-2-ol in 81–86% yield after hydrolysis. The conjugation in crotonaldehyde enables regioselectivity in nucleophilic additions: hard nucleophiles like hydride from NaBH₄ or organomagnesium reagents favor 1,2-addition at the carbonyl, while soft nucleophiles such as thiols or enolates prefer 1,4-conjugate addition at the β-carbon, guided by hard-soft acid-base principles.

Polymerization and stability

Crotonaldehyde exhibits a pronounced tendency to self-polymerize, primarily through radical mechanisms initiated by exposure to light or heat, or via acid-catalyzed pathways that lead to dimerization and resin formation. This spontaneous polymerization can generate significant heat and pressure, posing risks of container rupture if not controlled. The process is exacerbated by contamination or prolonged storage without stabilizers, resulting in the formation of viscous resins that diminish the compound's utility. The compound's stability is compromised by sensitivity to air oxidation, which promotes the formation of explosive peroxides over time, particularly when exposed to oxygen without inhibitors. Crotonaldehyde also undergoes decomposition at elevated temperatures, typically above 50°C, releasing acrid fumes and potentially accelerating polymerization. To mitigate these issues, commercial preparations include stabilizers such as butylated hydroxytoluene (BHT) at 0.1% or water at 1%, with alternatives like hydroquinone commonly employed for similar unsaturated aldehydes to inhibit radical initiation. Acetic acid may also be added in certain formulations to suppress acid-catalyzed reactions during storage. Under proper conditions—refrigeration at 2–8°C and protection from light—stabilized crotonaldehyde maintains stability for several months, minimizing discoloration from oxidation and resinification. However, exposure to air, light, or temperatures exceeding room conditions shortens shelf life, leading to yellowing or browning.

Applications

Industrial uses

Crotonaldehyde serves as a key precursor in the industrial production of , which is synthesized by reacting crotonaldehyde with to form a polyester intermediate, followed by decomposition. Sorbic acid is widely used as a preservative in food and beverages to inhibit yeast and mold growth. It is also employed in the synthesis of crotonyl chloride, derived from the oxidation product crotonic acid, which finds applications in manufacturing rubber accelerators and polymers such as those used in tire production and synthetic rubber formulations. As a solvent, crotonaldehyde effectively dissolves vegetable and mineral oils, fats, waxes, natural and synthetic resins, and elemental sulfur, making it valuable in formulations for paints, coatings, and lubricant additives in the chemical and materials industries. In agriculture, crotonaldehyde reacts with urea to form crotonylidene diurea (CDU), a slow-release nitrogen fertilizer that provides sustained nutrient availability to crops over extended periods, reducing leaching and improving soil efficiency. Crotonaldehyde acts as an important intermediate in the synthesis chain for , contributing to large-scale production in the fine chemicals sector.

Pharmaceutical and other uses

Crotonaldehyde serves as a key intermediate in the multi-step synthesis of vitamin E (tocopherol), particularly through its conversion to trimethylhydroquinone, a critical precursor in the production process. This role leverages crotonaldehyde's reactivity as an α,β-unsaturated aldehyde to build the chroman ring structure essential for tocopherol's antioxidant properties. In pharmaceutical applications, it also contributes to the synthesis of other fine chemicals and pharmaceuticals derived from crotonic acid. It is primarily employed in the manufacture of sorbic acid, a widely used yeast and mold inhibitor that preserves products like food and cosmetics. In agriculture, crotonaldehyde acts as an intermediate in the synthesis of pyrethroid insecticides, which are valued for their efficacy in pest control and relatively low mammalian toxicity. These synthetic analogs of natural pyrethrins rely on crotonaldehyde derivatives to form key structural elements that enhance insecticidal activity. Emerging applications include its use as a denaturant in biofuel formulations, where crotonaldehyde's toxicity and pungent odor render ethanol unfit for consumption, complying with regulatory requirements for fuel-grade products. Although crotonaldehyde occurs naturally at low levels in foodstuffs like soybean oils and contributes to flavor profiles through lipid peroxidation, its direct use as a flavoring agent is limited by toxicity concerns. Historically, in the early 20th century, crotonaldehyde found applications in the production of dyes and as a precursor for perfume intermediates, capitalizing on its versatility in organic synthesis before shifting to more specialized roles.

Health and safety

Toxicity and health effects

Crotonaldehyde is highly toxic through multiple exposure routes, with inhalation being the primary concern due to its volatility and vapor formation, while dermal absorption and ingestion are also possible pathways. The substance can penetrate the skin upon direct contact, leading to systemic effects, and oral ingestion exacerbates acute risks. Acute exposure to crotonaldehyde causes severe irritation to the eyes, skin, and respiratory tract at low concentrations, often in the parts per million (ppm) range. The oral LD50 in rats is reported as 174 mg/kg, indicating high acute toxicity via ingestion. Inhalation of vapors produces a burning sensation in the nasal passages and upper respiratory tract, lacrimation, coughing, and bronchoconstriction, potentially progressing to pulmonary edema at higher levels. Eye contact results in corneal damage and severe irritation, while skin exposure causes redness, pain, and burns. The odor threshold is approximately 0.2 ppm, which is suffocating and can induce respiratory distress even before toxic concentrations are reached. Chronic exposure to crotonaldehyde is associated with an increased risk of respiratory diseases, acting as a potent irritant to the lungs and airways over prolonged periods. As an α,β-unsaturated carbonyl compound, it reacts with to form adducts, such as those at the N2 position of deoxyguanosine, contributing to genotoxic effects. These adducts have been detected in lung tissue following exposure, linking the compound to cellular damage in respiratory organs. Crotonaldehyde is classified by the International Agency for Research on Cancer (IARC) as possibly carcinogenic to humans (Group 2B), based on limited evidence of carcinogenicity in experimental animals and strong mechanistic evidence including genotoxicity. It demonstrates mutagenicity in the Ames test using Salmonella typhimurium strains, particularly TA100, indicating its potential to induce point mutations.

Handling precautions

Crotonaldehyde is a highly flammable liquid with a flash point of 13 °C (closed cup) and an autoignition temperature of 232 °C, necessitating storage below 13 °C in approved flammable liquid safety cabinets to minimize fire and explosion risks. In laboratory and industrial settings, operations must occur in well-ventilated areas, such as under a chemical fume hood, to prevent accumulation of explosive vapor-air mixtures, which have lower and upper explosive limits of 2.1% and 15.5% by volume, respectively. Appropriate personal protective equipment (PPE) is essential, including nitrile rubber gloves (minimum thickness 0.4 mm, breakthrough time >30 minutes), chemical-resistant or face shields, and respiratory protection with organic vapor cartridges for concentrations up to 50 ppm; for higher levels or unknown exposures, use a full-facepiece pressure-demand . Full-body protective clothing, such as aprons or suits made from materials resistant to aldehydes, should be worn to prevent and . Crotonaldehyde is incompatible with acids, bases (caustics), strong oxidizers, , , and amines, as these can trigger violent reactions or exothermic ; avoid such materials during handling and storage to prevent hazards. In the event of a spill, evacuate the area, ventilate, and avoid ignition sources; absorb the liquid with an inert material such as or sand, then neutralize residues with a solution before disposal as in accordance with local regulations. Regulatory exposure limits include a NIOSH (REL) and OSHA (PEL) of 2 ppm (6 mg/m³) as an 8-hour time-weighted average, with an immediately dangerous to life or (IDLH) value of 50 ppm; the U.S. Department of Transportation (DOT) classifies crotonaldehyde as a Poison (Zone B), requiring specific placarding and shipping protocols.

Environmental impact

Sources and occurrence

Crotonaldehyde occurs naturally at trace levels in various environmental compartments, primarily through biological emissions and reactions. It is emitted from certain vegetation, such as the Chinese arbor vitae plant (Thuja orientalis), and has been detected in volcanic gases. Additionally, crotonaldehyde forms via atmospheric reactions, including the photooxidation of biogenic volatile organic compounds (VOCs) like from plants. In food sources, it appears in small amounts in , , fruits (e.g., apples, grapes, strawberries, tomatoes), and vegetables (e.g., , , ), often resulting from natural processes. Anthropogenic sources contribute significantly to crotonaldehyde's environmental presence, mainly as a byproduct. It is released from exhaust ( and diesel engines), wood burning, and tobacco smoke, with emissions arising during incomplete oxidation of hydrocarbons. Industrial processes, particularly the of used in its production, also generate emissions, though these are typically controlled at manufacturing sites. These sources elevate crotonaldehyde levels in both outdoor and indoor environments, where indoor air can contain contributions from outdoor infiltration and indoor activities like cooking. As a (VOC), crotonaldehyde exhibits moderate environmental persistence in the atmosphere, with an atmospheric of approximately 11 hours due to degradation via photooxidation by hydroxyl radicals. This process leads to its breakdown into simpler compounds but also contributes to the formation of secondary pollutants, such as and secondary organic aerosols, exacerbating air quality issues. In and , it hydrolyzes or biodegrades relatively quickly, though it can persist longer in anaerobic conditions. Crotonaldehyde is routinely measured in environmental samples using techniques like . In urban air, concentrations typically range from 0.3 to 0.5 ppb, with higher levels (up to several ppb) near or sources. It has been detected in at low levels, around 0.5 μg/L, and in wastewater effluents from industrial discharges. In foods, particularly those processed via the during cooking or frying, concentrations vary; for example, fried potato chips contain 12–25 μg/kg, while heated oils can reach up to 34 mg/kg under extreme conditions. Its presence in indoor air, often 1–2 times higher than outdoor levels due to poor ventilation, underscores its status as a ubiquitous linked to risks from chronic low-level exposure.

Regulations and mitigation

Crotonaldehyde is regulated under the U.S. Clean Air Act Section 112(r) as a regulated substance subject to the Risk Management Program (RMP), requiring facilities handling more than 20,000 pounds to implement prevention programs and emergency response plans to mitigate accidental releases. Production facilities are also subject to National Emission Standards for Hazardous Air Pollutants (NESHAP) if they are major sources of organic emissions under the Hazardous Organic NESHAP (HON). In the European Union, occupational exposure limits for crotonaldehyde in workplace air are established through the Scientific Committee on Occupational Exposure Limits (SCOEL), with recommendations informing indicative limits typically around 0.5–2 ppm (approximately 1.4–5.7 mg/m³) time-weighted average, though specific national implementations vary. Under the (RCRA), crotonaldehyde is classified as a with code U053 when discarded, subjecting it to strict management, storage, and disposal requirements to prevent environmental release. For containing crotonaldehyde, treatment methods include adsorption using to reduce toxicity and enhance biological processes, as well as such as ozonation or to degrade the compound into less harmful byproducts. Mitigation strategies for crotonaldehyde emissions include the use of catalytic converters in , which oxidize aldehydes like crotonaldehyde, achieving 50–80% reduction in exhaust emissions. In industrial settings, wet scrubbers installed on emission stacks capture volatile organic compounds, including crotonaldehyde, through absorption in liquid solutions, often achieving removal efficiencies of 85–90% for similar pollutants. Internationally, the (WHO) provides guidelines for focusing on volatile organic compounds, recommending ventilation and source control to minimize exposure to irritants like aldehydes, though no specific threshold is set for crotonaldehyde. Post-2020 research has advanced biofiltration techniques for crotonaldehyde removal from air streams, with studies demonstrating up to 90% elimination efficiency using mixed-bed biofilters packed with microbial consortia and adsorbents. (Note: Referenced in 2023 reviews for ongoing applicability.) Environmental monitoring of crotonaldehyde relies on gas chromatography-mass spectrometry (GC-MS), which provides sensitive detection in air, , and samples down to parts-per-billion levels, enabling compliance assessment and source tracking.

References

  1. https://pubchem.ncbi.nlm.nih.gov/compound/Crotonaldehyde
  2. https://wwwn.cdc.gov/TSP/ToxFAQs/ToxFAQsDetails.aspx?faqid=948&toxid=197
  3. https://www.tceq.texas.gov/downloads/toxicology/dsd/final/crotonaldehyde.pdf
  4. http://publications.iarc.who.int/Book-And-Report-Series/Iarc-Monographs-On-The-Identification-Of-Carcinogenic-Hazards-To-Humans/Acrolein-Crotonaldehyde-And-Arecoline-2021
  5. https://www.merriam-webster.com/dictionary/crotonaldehyde
  6. https://webbook.nist.gov/cgi/cbook.cgi?ID=C123739
  7. https://www.ncbi.nlm.nih.gov/books/NBK589585/
  8. https://go.drugbank.com/drugs/DB04381
  9. https://www.fishersci.ca/shop/products/crotonaldehyde-predominantly-trans-98-thermo-scientific/p-7043893
  10. https://www.inchem.org/documents/icsc/icsc/eics0241.htm
  11. https://www.osha.gov/sites/default/files/methods/osha-81.pdf
  12. https://cameochemicals.noaa.gov/chemical/4931
  13. https://publications.iarc.who.int/_publications/media/download/2114/1d1543fc5e73dc183431c6d96c4e14ac64fac9ca.pdf
  14. https://papers.ssrn.com/sol3/papers.cfm?abstract_id=4621764
  15. https://www.sciencedirect.com/science/article/abs/pii/S1383586623030319
  16. https://www.celanese.com/products/crotonaldehyde
  17. https://doi.org/10.1016/j.psep.2023.08.090
  18. https://pubs.rsc.org/en/content/articlelanding/2023/re/d2re00251e
  19. https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Alcohols/Reactivity_of_Alcohols/The_Oxidation_of_Alcohols/Oxidation_by_PCC_(pyridinium_chlorochromate)
  20. https://commonorganicchemistry.com/Common_Reagents/Manganese%28IV%29_Dioxide/Manganese%28IV%29_Dioxide.htm
  21. https://onlinelibrary.wiley.com/doi/10.1002/047084289X.rc253
  22. https://pubs.acs.org/doi/10.1021/acscatal.1c01216
  23. https://www.sciencedirect.com/science/article/pii/S0891584921002008
  24. https://www.researchgate.net/figure/Scheme-1-Diels-Alder-reaction-between-cyclopentadiene-and-crotonaldehyde_fig1_256737611
  25. http://orgsyn.org/demo.aspx?prep=CV3P0696
  26. https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(Morsch_et_al.)/19%3A_Aldehydes_and_Ketones-_Nucleophilic_Addition_Reactions/19.13%3A_Conjugate_Nucleophilic_Addition_to_%CE%B1%2C%CE%B2-Unsaturated_Aldehydes_and_Ketones
  27. https://pim-resources.coleparmer.com/sds/56057.pdf
  28. https://www.sigmaaldrich.com/US/en/sds/aldrich/27980
  29. https://www.fishersci.com/store/msds?partNumber=AC427181000
  30. https://patents.google.com/patent/US4296243A/en
  31. https://www.researchgate.net/publication/277692238_Crotonaldehyde_and_Crotonic_Acid
  32. https://www.sigmaaldrich.com/US/en/product/aldrich/27980
  33. https://www.sciencedirect.com/science/article/pii/S1002016017604296
  34. https://www.celanese.com/-/media/Intermediate-Chemistry/Files/Brochures/Crotonaldehyde-Brochure.pdf
  35. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3733701.htm
  36. https://www.sciencedirect.com/topics/pharmacology-toxicology-and-pharmaceutical-science/crotonaldehyde
  37. https://www.futuremarketinsights.com/reports/crotonaldehyde-market
  38. https://godavaribiorefineries.com/industries/biofuels/denaturant/crotonaldehyde-%25E2%2580%2593-85
  39. https://www.industrialchemicals.gov.au/sites/default/files/Crotonaldehyde_Human%2520health%2520tier%2520II%2520assessment.pdf
  40. https://www.ncbi.nlm.nih.gov/books/NBK207868/
  41. https://nj.gov/health/eoh/rtkweb/documents/fs/0538.pdf
  42. https://pubs.acs.org/doi/abs/10.1021/tx060154d
  43. https://publications.iarc.who.int/Book-And-Report-Series/Iarc-Monographs-On-The-Identification-Of-Carcinogenic-Hazards-To-Humans/Acrolein-Crotonaldehyde-And-Arecoline-2021
  44. https://cebs.niehs.nih.gov/cebs/test_article/4170-30-3
  45. https://www.fishersci.com/store/msds?partNumber=AC427181000&productDescription=CROTONALDEHYDE%2B99%252B%2525%2BAC%2B100ML&vendorId=VN00032119&countryCode=US&language=en
  46. https://www.cdc.gov/niosh/npg/npgd0157.html
  47. https://www.medline.com/media/catalog/Docs/MSDS/MSD_SDSD97516.pdf
  48. https://www.chemicalbook.com/msds/Crotonaldehyde-trans-predominantly.pdf
  49. https://www.epa.gov/sites/default/files/2014-11/documents/crotonaldehyde_final_volume6_2007_0.pdf
  50. https://www.ncbi.nlm.nih.gov/books/NBK464378/
  51. https://www.sciencedirect.com/topics/medicine-and-dentistry/crotonaldehyde
  52. https://www.sciencedirect.com/science/article/pii/0048969796052485
  53. https://www.researchgate.net/publication/259764736_Development_of_Three_Stable_Isotope_Dilution_Assays_for_the_Quantitation_of_E-2-Butenal_Crotonaldehyde_in_Heat-Processed_Edible_Fats_and_Oils_as_Well_as_in_Food
  54. https://www.sciencedirect.com/science/article/abs/pii/S1352231005011672
  55. https://www.epa.gov/rmp/list-regulated-substances-under-risk-management-program
  56. https://www.govinfo.gov/content/pkg/FR-1998-05-12/html/98-12579.htm
  57. https://esd.uga.edu/rcra-compliance/epa-hazardous-waste-codes
  58. https://www.sciencedirect.com/science/article/abs/pii/S0957582025013199
  59. https://www.slchemtech.com/news/how-to-treat-aldehyde-containing-wastewater.html
  60. https://zenodo.org/record/8261/files/1307549830-Published_Sasi_Kumar_2011ACSj214.pdf
  61. https://www.epa.gov/sites/default/files/2021-05/documents/wet_and_dry_scrubbers_section_5_chapter_1_control_cost_manual_7th_edition.pdf
  62. https://www.sciencedirect.com/science/article/abs/pii/S1226086X18300418
  63. https://pmc.ncbi.nlm.nih.gov/articles/PMC11503962/
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