1629-58-9

Usage

Uses

Ethyl vinyl ketone is used as a reagent for annulation.
Used in Flavor Industry:
Ethyl vinyl ketone is used as a flavoring agent for its unique aroma and taste characteristics. It has a taste threshold value of 5.0 ppm, which is described as pungent, ethereal, peppery, garlic, onion, fishy, and mustard with a hot nuance.
Used in Food Industry:
Ethyl vinyl ketone is found in various food items such as banana, orange peel oil, grapefruit juice and peel, peach, lean fish, fish oil, chicken fat, black tea, soybean, defatted soybean, lovage leaf, endive, chive, oysters, clam, boiled and cooked beef, kiwifruit, guava, grapes, tomato, butter, and maté. It contributes to the distinct flavor and aroma of these foods.
Used in Chemical Industry:
Ethyl vinyl ketone is used in the synthesis of various chemicals and compounds due to its reactive nature and ability to polymerize readily with heat or in the presence of alkali.

Preparation

By reacting ethylene with a mixture of propionyl chloride, aluminum trichloride and carbon disulfide.

Safety Profile

Poison by intravenous route. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES

InChI:InChI=1/C5H8O/c1-3-5(6)4-2/h3H,1,4H2,2H3

Upstream product

• 32830-97-0 1-chloro-3-pentanone 
• 5371-48-2 3,4,5-pentanetriol 
• 109-67-1 1-penten 
• 616-25-1 1-Penten-3-ol 
• 74-85-1 ethene 
• 79-03-8 propionyl chloride 
• 3536-96-7 vinylmagnesium chloride 
• 123-62-6 propionic acid anhydride 
• 50-00-0 formaldehyd 
• 78-93-3 butanone 
• 91-66-7 N,N-diethylaniline 
• 53931-56-9 2-benzenesulfinyl-pentan-3-one 
• 110-88-3 1,3,5-Trioxan 
• 67-64-1 acetone 

Downstream Products

• 92356-25-7 ethyl-4-(4'-methyl-3'-pentenyl)-3-cyclohexenyl ketone 
• 38820-34-7 2,3,4,4a,9,10-hexahydro-7-methoxy-1,4aβ-dimethyl-2-phenanthrone 
• 58720-45-9 15,15'-didehydro-β,β-caroten-4-one 
• 5920-29-6 3-Ethyl-Δ²-pyrazolin 
• 600-14-6 2,3-Pentanedione 
• 584-02-1 2-pentanol 
• 77828-22-9 2-(3-oxo-pentyl)-cyclohexane-1,3-dione 
• 5257-46-5 2-(1-Propanonyl)Bicyclo<2.2.1>Hept-5-en 
• 33279-05-9 N,N-diethyl-1-amino-3-pentanone 
• 13395-71-6 2,4,4-trimethyl-2-cyclohexenone 
• 95496-05-2 1-(phenylamino)pentan-3-one 
• 14659-66-6 3-phenyl-5-propionylisoxazole 
• 28255-09-6 (RS)-4,7a-dimethyl-2,3,7,7a-tetrahydro-(6H)-indene-1,5-dione 
• 92723-42-7 2-Methyl-4-isopropenyl-4-carbomethoxy-1.3-cyclohexandion 

Relevant academic research and scientific papers

A Convenient Preparation of Ethyl Vinyl Ketone

A four-step synthesis of ethyl vinyl ketone conveniently gives 67percent overall yield.

Products and mechanism of the reaction of chlorine atoms with 3-pentanone in 700-950 Torr of N2/O2 diluent at 297-515 K

The products, kinetics, and mechanism of the reaction Cl + 3-pentanone have been measured by UV irradiation of Cl2/3-pentanone/N2 (O2) mixtures using primarily GC analysis with selected cross checks by FTIR. In the absence of O2, the products are 1- and 2-chloro-3-pentanone with yields of 21 and 78%, respectively. As the temperature is increased, the yield of 1-chloro-3-pentanone increases modestly relative to the 2-chloro-3-pentanone yield. On the basis of this increase, the activation energy for hydrogen abstraction at the 1 position is determined to be 500 (±500) cal mole-1 relative to abstraction at the 2 position. In the presence of 500 ppm of O2 with 900-1000 ppm of Cl2 at 297 K, the yield of 2-chloro- 3-pentanone decreases dramatically from 78 to 2.5%, while the 1-chloro-3-pentanone decreases only modestly from 21 to 17%. The observed oxygenated species are acetaldehyde (59%), 2,3-pentanedione (9%), and propionyl chloride (56%). Increasing the temperature to 420 K (O2 = 500 ppm) suppresses these oxygenated products, and 2-chloro-3-pentanone again becomes the primary product, indicating that the O2 addition reaction to the 2-pentanonyl radical has become reversible. At 500 K and 10 000 ppm O 2, a new product channel opens which forms a small yield (～4%) of ethylvinylketone. Computer modeling of the product yields has been performed to gain an understanding of the overall reaction mechanism in the presence and absence of O2. The reaction of chlorine atoms with 3-pentanone proceeds with a rate constant of 8.1 (±0.8) × 10-11 cm3 molecule-1 s-1 independent of temperature over the range of 297-490 K (Ea = 0 ± 200 cal mole-1). Rate constant ratios of K(C2H 5C(O)CHCH3 + Cl2)/ k(C2H 5C(O)CHCH3 + O2) = 0.0185 ± 0.0037 and k(C2H5C(O)CH2CH + Cl2)/ k(C 2H5CH2C(O)CH2CH2 + O 2) = 2.7 ± 0.4 were determined at 297 K in 800-950 Torr of N2/O2 diluent. In 800-950 Torr of N2/O 2 diluent, the major fate of the alkoxy radical CH 3CH(O)C(O)C2H5 is decomposition to give C 2H5C(O) radicals and CH3CHO. These results show that the chemical mechanisms of the 3-pentanone reactions are very similar to those observed for butanone. In addition, the rate constants of the reactions of chlorine atoms with 1-chloro-3-pentanone [3 (±0.6) x 10-11 over the range of 297-460 K], 2,3-pentanedione [1.4 (±0.3) × 10-11 at 297 K], and ethylvinylketone [1.9 (±0.4) × 10-10 over the range of 297-400 K, decreasing rapidly above 400 K] were measured at ambient pressure.

Methylvinyl Ketone Formation over Synthetic Chrysotile

Selective formation of methylvinyl ketone (MVK) was attained over chrysotile, Mg3(OH)4Si2O5, through aldol condensation reaction between acetone and formaldehyde, the selectivity being 98 percent on both acetone and formaldehyde bases.Synthetic Co2+-substituted chrysotile, CoxMg3-x(OH)4Si2O5 (x= 0.15 or 0.9), catalyzed the reaction between acetone and methanol to give MVK and methylethyl ketone (MEK) with 75 percent selectivity on acetone basis.

The dual role of cis-[RuCl2(dmso)4] in the synthesis of new water-soluble Ru(II)-phosphane complexes and in the catalysis of redox isomerization of allylic alcohols in aqueous-organic biphasic systems

New air-stable, water-soluble Ru(II)-phosphane complexes were synthesized in high purity by the reaction of cis-[RuCl2(dmso)4] with 2 equivalents of 1,3,5-triaza-7-phosphaadamantane (pta) and its N-methyl and N-benzyl derivatives (pta-Me and pta-Bn, respectively). All new complexes were characterized by elementary analysis and spectroscopic methods (NMR, ESI-MS) and the molecular structures of cis-cis-trans-[RuCl2(dmso) 2(pta)2], cis-cis-trans-[RuCl2(dmso) 2(pta-H)2]Cl2 (obtained in acidic solutions) and that of cis-cis-trans-[RuCl2(dmso)2(pta-Me) 2](CF3SO3)2 were determined by single crystal X-ray diffraction. Under mild conditions, cis-[RuCl 2(dmso)4] actively catalyzed the transformation of allylic alcohols into the corresponding ketones with 100% selectivity while in the same reaction the new Ru(II)-pta complexes showed moderate activity and selectivity.

Cu2O-CuO/Chitosan Composites as Heterogeneous Catalysts for Benzylic C?H Oxidation at Room Temperature

Recently, in catalysis, chitosan has been exploited as a macrochelating ligand for metal active species due to the presence of various functional groups in its structure. Moreover, copper-based catalysts are classified as one of the most environmentally friendly catalytic systems and their use for the oxidation of alkylarene has not been established much. Therefore, in this work, the hydrothermal synthesis of copper oxide-chitosan composites as heterogeneous catalysts for the benzylic C?H oxidation of alkylarene was investigated. Characterization results reveal mixed phases of CuO and Cu2O, inferring the ability of chitosan to act as a reducing sugar under the hydrothermal condition. The pre-existing interaction between copper species and chitosan as well as the co-existence of the Cu2O and CuO structures give rise to the efficient performance of the catalysts. The synthesized composites exhibit high activity for the oxidation of fluorene to 9-fluorenone at room temperature and small catalyst loading (1 mol % of Cu, >90 % conversion and 100 % selectivity). Superior TOF was observed, and a good scope of substrates can be converted to corresponding ketones in 48–97 % yields with these copper oxide-chitosan catalysts. In addition, the catalysts can be used for up to nine cycles without significant decrease of the activity.

Palladium mediated one-pot synthesis of 3-aryl-cyclohexenones and 1,5-diketones from allyl alcohols and aryl ketones

One-pot synthesis of Robinson annulated 3-aryl-cyclohexenones from allyl alcohols and ketones using palladium is reported. Long chain aliphatic or aryl substitutions at the C1 position of allyl alcohol result in the formation of 1,5-diketone products. This simple one-pot method avoids the use of highly electrophilic vinyl ketones.

K2S2O8-promoted C-Se bond formation to construct α-phenylseleno carbonyl compounds and α,β-unsaturated carbonyl compounds

A novel K2S2O8-promoted C-Se bond formation from cross-coupling under neutral conditions has been developed. A variety of aldehydes and ketones react well using K2S2O8 as the oxidant in the absence of catalyst and afford desired products in moderate to excellent yields. This protocol provides a very simple route for the synthesis of α-phenylseleno carbonyl compounds and α,β-unsaturated carbonyl compounds.

Changes in the Key Odorants and Aroma Profiles of Hamlin and Valencia Orange Juices Not from Concentrate (NFC) during Chilled Storage

Application of the aroma extract dilution analysis (AEDA) on the volatiles isolated by extraction/SAFE distillation from NFC (not from concentrate) juice from Hamlin oranges revealed 51 odor-active constituents in the flavor dilution (FD) factor range of 8 to 8192 among which vanillin, wine lactone, and (R)-linalool appeared with the highest FD factors. The AEDA applied on the volatile fraction of the same batch of juice stored at 0 °C for 10 months under aseptic conditions showed clear changes in the aroma profile as well as in the FD factors of key odorants. The reduction in the intensity of the citrus-like, pungent, green odor attributes in the aroma profile correlated with the loss of 1-penten-3-one, acetaldehyde, and (Z)-3-hexenal and a clear decrease in hexanal, octanal, nonanal, decanal, and (E,E)-2,4-decadienal. Quantitation done by stabile isotope dilution assays followed by a calculation of odor activity values (ratio of concentration to odor thresholds in citrate buffer) confirmed that the quick loss of 1-penten-3-one and acetaldehyde already within a few weeks and a significant reduction in nearly all aldehydes over the storage time of 10 months were responsible for the changes in the overall aroma profile of the juice. The same approach applied on Hamlin juice from the next harvest year as well as on chilled stored NFC juice from Valencia oranges confirmed the results for another harvest year and another orange variety.

Stereoselective Allylic Alkylation of 1-Pyrroline-5-carboxylic Esters via a Pd/Cu Dual Catalysis

The asymmetric allylation of 1-pyrroline-5-carboxylic esters has been accomplished through a synergistic Pd/Cu catalyst system under mild reaction conditions. The mechanistic studies suggested that (1) nucleophilic attack is the enantiodiscriminating step; (2) the cooperative action of two chiral reactive species, N-metalated azomethine ylides and ?€-allylpalladium, is most likely responsible for its high reactivity and excellent enantioselectivity (up to >99% ee); and (3) the steric hindrance and electronic factors of the allylic electrophiles and imino ester substrates are crucial for the formation of the linear products. A series of 3,4-2H-pyrrole derivatives bearing a quaternary stereogenic center were easily synthesized in high yields and with high to excellent regioselectivity and enantioselectivity.

Expanding the scope of the Babler–Dauben oxidation: 1,3-oxidative transposition of secondary allylic alcohols

We report the catalytic chromium-mediated oxidation of secondary allylic alcohols to give α,β-unsaturated aldehydes with exclusive (E)-stereoselectivity. This facile procedure employs catalytic PCC (5?mol?%) and periodic acid (H5IO6) as a co-oxidant. This transformation occurs specifically with aromatic substituted allyl alcohols containing both electron withdrawing and electron donating substituents as well as a range of functional groups.