Ethyl propyl acrolein

Acrolein (19), Crotonaldehyde (19), and 2-Ethyl-3-propyl acrolein (19) are not compatible with Group 1, Non-... 

CO. CHa, CO2, acetone, ketene. ethene. propene, 1-butene, benzene, toluene, mesitylene. xylene, methyl ethyl ketone, diethyl ketone, methyl-n-propyt ketone, methyl-n-butyl ketone, ethyl vinyl ketone, methyl propenyl ketone (trace), ethyl propyl ketone (trace), 3-methyl-cydopenlanone, cyclohexanone (trace), cyclohexa-2-enone, 2-methyl-cyclohexanone, 1-methyl-cydohexa-1-ene-3-one (trace), acrolein, mesityl oxide, ethanal, propanal. butanal. chain fragments, some monomer... 

Simple alkyl radicals such as methyl are considered to be nonnucleophilic. Methyl radicals are somewhat more reactive toward alkenes bearing electron-withdrawing substituents than towards those with electron-releasing substituents. However, much of this effect can be attributed to the stabilizing effect that these substiments have on the product radical. There is a strong correlation of reaction rate with the overall exothermicity of the reaction. Hydroxymethyl and 2-hydroxy-2-propyl radicals show nucleophilic character. The hydroxymethyl radical shows a slightly enhanced reactivity toward acrylonitrile and acrolein, but a sharply decreased reactivity toward ethyl vinyl ether. Table 12.9 gives some of the reactivity data. 

Ethyl Grignard added chorrosoloctivcly to acrolein (17) in good yield, but iso-propyl Grignard failed to give the reaction. The alternative straieg (6) was successful In this case. 

ETHYLENE GLYCOL ETHYL MERCAPTAN DIMETHYL SULPHIDE ETHYL AMINE DIMETHYL AMIDE MONOETHANOLAMINE ETHYLENEDIAMINE ACRYLONITRILE PROPADIENE METHYL ACETYLENE ACROLEIN ACRYLIC ACID VINYL FORMATE ALLYL CHLORIDE 1 2 3-TRICHLOROPROPANE PROPIONITRILE CYCLOPROPANE PROPYLENE 1 2-DICHLOROPROPANE ACETONE ALLYL ALCOHOL PROPIONALDEHYDE PROPYLENE OXIDE VINYL METHYL ETHER PROPIONIC ACID ETHYL FORMATE METHYL ACETATE PROPYL CHLORIDE ISOPROPYL CHLORIDE PROPANE... 

Cyclohexane Methylcyclohexane Phenol Terpenes Turpentine Alcohols Methyl alcohol Ethyl alcohol 2-propen-l-ol n-Propyl alcohol Isopropyl alcohol n-Butyl alcohol Amyl alcohol Isoamyl alcohol Aldehydes Formaldehyde Acetaldehyde Acrolein... 

Acetamido-4-amino-6-chloro-s-triazine, see Atrazine Acetanilide, see Aniline, Chlorobenzene, Vinclozolin Acetic acid, see Acenaphthene, Acetaldehyde, Acetic anhydride. Acetone, Acetonitrile, Acrolein, Acrylonitrile, Aldicarb. Amyl acetate, sec-Amyl acetate, Bis(2-ethylhexyl) phthalate. Butyl acetate, sec-Butyl acetate, ferf-Butyl acetate, 2-Chlorophenol, Diazinon. 2,4-Dimethylphenol, 2,4-Dinitrophenol, 2,4-Dinitrotoluene, 1,4-Dioxane, 1,2-Diphenylhydrazine, Esfenvalerate. Ethyl acetate, Flucvthrinate. Formic acid, sec-Hexyl acetate. Isopropyl acetate, Isoamyl acetate. Isobutyl acetate, Methanol. Methyl acetate. 2-Methvl-2-butene. Methyl ferf-butvl ether. Methyl cellosolve acetate. 2-Methvlphenol. Methomvl. 4-Nitrophenol, Pentachlorophenol, Phenol. Propyl acetate. 1,1,1-Trichloroethane, Vinyl acetate. Vinyl chloride Acetoacetic acid, see Mevinphos Acetone, see Acrolein. Acrylonitrile. Atrazine. Butane. 

CO, CH4, CO2, acetone, ketene. ethene. propene. 1-butene, benzene, toluene, xylene, cydopentene, methyl ethyl ketone, diethyl ketone, methyl-n-propyl ketone, di-n-propyl ketone, methyl vinyl ketone, methyl Isopropenyl ketone, methyl isopropyl ketone, ethyl vinyl ketone, trace amounts of methyl-n-bulyl ketone, cyclopentanone, cydohexanone. acrolein, ethanal. butanal. chain fragments, some monomer CO. CH4, COj, ketene, 1-butene, propene, acetone, methyl ethyl ketone, methyl n-propyl ketone, 1,4-cyclohexadiene. toluene, l-methy. l.3-cydohexadlene, 2-hexanone, cydopentene, 1-methyl cydopentene. mesityl oxide, xylenes, benzene, ethene, cyclopentanone, 1.3-cyclopentad iene, diethyl ketone, short chain fragments, traces of monomer CO, CH4, COi, ketene, 1-butene, propene, acetone, methyl ethyl ketone, methyl isopropyl ketone, methyl-n-propyl ketone, diethyl ketone, methyl propenyl ketone, 3-hexanone. toluene, 2-hexanone. 1,3-cydopentadiene, cyclopentanone, 2-melhylcydopenlanone, mesityl oxide, xylenes, benzene, propionaldehyde, acrolein, acetaldehyde ethene, short chain fragments, traces of monomer CO, COj, H2O, CH4. acetone, ketene, ethene, propylene, 1-butene, methyl vinyl ketone, benzene, acrylic add, toluene, xylene, short chain fragments such as dimer to octamer with unsaturated and anhydride functionalities... 

The use of ethyl alcohol for the selective reduction of the carbonyl group in unsaturated aldehydes and ketones other than acrolein is illustrated in Table V. Here also, the data listed are the best obtained in a limited number of runs with each compound and do not necessarily represent optimum conditions. As previously stated, in the acrolein-allyl alcohol reaction a small amount of propyl alcohol is found in the products. This side reaction appears to be considerably more important with crotonaldehyde, since the C4 alcohol fraction here contained 27 % butyl alcohol. The relatively high conversion to saturated alcohol is believed to be due in part to unfavorable reaction conditions. With methacrolein and with methyl isopropenyl ketone the saturated alcohol amounted to 5 % of the imsaturated alcohol produced. 

A feature of the acrolein-allyl alcohol reaction is the small but measurable production of propyl alcohol. This product could arise by rearrangement of allyl alcohol to propionaldehyde followed by hydrogen exchange of propionaldehyde with either ethyl alcohol or allyl alcohol. 

Mixed vapors of acrolein and ethyl alcohol were passed over the catalyst in a heated stainless steel tube at atmospheric pressure. Products were condensed and fractionated in a 20-plate bubble tray column. Fractions taken were acetaldehyde, 20-36°, and acrolein-ethyl alcohol, 36-78.4°. At this point water was added to the distillation kettle and an ethyl alcohol-aUyl alcohol-water fraction, 78-95°, was taken overhead. Fractions were analyzed for aldehydes by the hydroxylamine hydrochloride method, for im-saturation by reaction with bromine in aqueous potassium bromide, for alcohol by the nitrite ester method, and for water with Fischer reagent. Propyl alcohol in the water-free allyl alcohol recovered from the azeotrope was calculated by difference from the total alcohol determined by reaction with acetyl chloride and the unsaturated alcohol determined by reaction with aqueous bromine solution. Fresh catalyst was used for each experiment. 

---