Methyl acetate chloride

Acetyl chloride Acetic anhydnde Methyl acetate Acetamide... 

Acetic acid, fp 16.635°C ((1), bp 117.87°C at 101.3 kPa (2), is a clear, colorless Hquid. Water is the chief impurity in acetic acid although other materials such as acetaldehyde, acetic anhydride, formic acid, biacetyl, methyl acetate, ethyl acetoacetate, iron, and mercury are also sometimes found. Water significantly lowers the freezing point of glacial acetic acid as do acetic anhydride and methyl acetate (3). The presence of acetaldehyde [75-07-0] or formic acid [64-18-6] is commonly revealed by permanganate tests biacetyl [431-03-8] and iron are indicated by color. Ethyl acetoacetate [141-97-9] may cause slight color in acetic acid and is often mistaken for formic acid because it reduces mercuric chloride to calomel. Traces of mercury provoke catastrophic corrosion of aluminum metal, often employed in shipping the acid. 

The reaction mechanism and rates of methyl acetate carbonylation are not fully understood. In the nickel-cataly2ed reaction, rate constants for formation of methyl acetate from methanol, formation of dimethyl ether, and carbonylation of dimethyl ether have been reported, as well as their sensitivity to partial pressure of the reactants (32). For the rhodium chloride [10049-07-7] cataly2ed reaction, methyl acetate carbonylation is considered to go through formation of ethyUdene diacetate (33) ... 

The unit has virtually the same flow sheet (see Fig. 2) as that of methanol carbonylation to acetic acid (qv). Any water present in the methyl acetate feed is destroyed by recycle anhydride. Water impairs the catalyst. Carbonylation occurs in a sparged reactor, fitted with baffles to diminish entrainment of the catalyst-rich Hquid. Carbon monoxide is introduced at about 15—18 MPa from centrifugal, multistage compressors. Gaseous dimethyl ether from the reactor is recycled with the CO and occasional injections of methyl iodide and methyl acetate may be introduced. Near the end of the life of a catalyst charge, additional rhodium chloride, with or without a ligand, can be put into the system to increase anhydride production based on net noble metal introduced. The reaction is exothermic, thus no heat need be added and surplus heat can be recovered as low pressure steam. 

CeUulose triacetate is insoluble in acetone, and other solvent systems are used for dry extmsion, such as chlorinated hydrocarbons (eg, methylene chloride), methyl acetate, acetic acid, dimethylformamide, and dimethyl sulfoxide. Methylene chloride containing 5—15% methanol or ethanol is most often employed. Concerns with the oral toxicity of methylene chloride have led to the recent termination of the only triacetate fiber preparation faciHty in the United States, although manufacture stiH exists elsewhere in the world (49). 

The largest shifts in frequency occur for methyl acetate, where the hydrogens in formaldehyde are replaced by a methyl group and a methoxy group, and most strikingly in acetyl chloride, where the hydrogen atom is replaced by a chlorine atom and a methyl group. 

One way to investigate the electrophilic properties of these molecules is to examine the orbital that each uses to accept electrons from a nucleophile. This orbital is the lowest-unoccupied molecular orbital (LUMO). Examine the LUMO for methyl acetate (Z=OCH3), acetaldehyde (Z=H), N,N-dimethylacetamide (Z=N(CH3)2) and acetyl chloride (Z=C1) (acetaldehyde is not a carboxylic acid derivative, but is included here for comparison). What is the shape of the LUMO in the region of the carbonyl group Is it a o or 7U orbital Is it bonding or antibonding What other atoms contribute to the LUMO Which bonds, if any, would be weakened when a nucleophile transfers its electrons into the LUMO ... 

A molecule with a low energy LUMO can accept electrons more readily than a molecule with a higher energy LUMO. The LUMO energies (in au) for the above molecules ai e 0.192 (methyl acetate), 0.161 (acetaldehyde), 0.212 (N,N-dimethylacetamide), and 0.132 (acetyl chloride). Order these molecules from most electrophilic to least electrophilic. 

Acetyl-2-Dimethylsulfamylthioxanthene A suspension of 2-dimethylsulfamylthioxanthene (12.22 grams, 0.04 mol) in 60 ml of dimethoxymethane is cooled to 0°C and 17.2 ml of a 2.91 M solution of n-butyl lithium in heptane is added slowly in a nitrogen atmosphere while the temperature is maintained below 10°C. After an additional 10 minutes of stirring, the cooling bath is removed and a solution of 2.96 grams of methyl acetate in 20 ml of di-methoxyethane is added during % hour and then the mixture is stirred at 25°C for an additional 3 hours. The reaction mixture is then treated with 60 ml of ethyl acetate and with 60 ml of a 10% aqueous ammonium chloride solution. The layers are separated and the ethyl acetate layer is washed once with water (25 ml) and then the solvent is removed by distillation. 

Methanol, ethanol, acetone, methylene chloride, methyl acetate, THF, methyl cellosolve, ethyl cellosolve, butyl cellosolve, n-xylene, p-xylene, and o-xylene... 

The methoxy group of methyl acetate formed during the thermal decomposition of acetyl peroxide appears as an emission, whereas methyl chloride shows enhanced absorption. Consider the reaction sequence in equation (40). 

Dermal Effects. Skin irritation was noted in wildlife officers at the RMA after they handled sick or dead ducks without gloves (NIOSH 1981). Although the investigators concluded that diisopropyl methylphosphonate contributed to the local effects, a number of other compounds were present. Analysis of the pond water indicated the presence of a number of organic and inorganic contaminants, including diisopropyl methylphosphonate (11.3 ppm) aldrin (0.368 ppm) dieldrin (0.0744 ppm) dicyclo-pentadiene, bicycloheptadiene, diethyl benzene, dimethyl disulfide, methyl acetate, methyl isobutyl ketone, toluene, and sodium (49,500 ppm) chloride (52,000 ppm) arsenic (1,470 ppm) potassium (180 ppm) fluoride (63 ppm) copper (2.4 ppm) and chromium (0.27 ppm). Because of the presence of numerous compounds, it is unclear whether diisopropyl methylphosphonate was related to the irritation. 

All solvents used for general applications were of reagent grade. For special purposes, purification of solvents was effected using standard procedures. All other reagents were used as supplied commercially except as noted. A solution of chloromethyl methyl ether (6 mmole/mL) in methyl acetate was prepared by adding acetyl chloride (141.2 g, 1.96 mol) to a mixture of dimethoxy methane (180 mL, 2.02 mol) and anhydrous methanol (5.0 mL, 0.12 mol).20 The solution was diluted with 300 mL of 1,1,2,2-tetrachloroethane and used as a stock solution for the chloromethylation experiments. 

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... 

Methyl acetate Methyl acrylate Methyl r-butyrate Methyl w-butyrate Methyl chloride Methyl ethyl ketone Methyl formae Methyl iodide Methyl propionate Mehyl propyl ketone Methyl sulfide Naphthalene Nitric acid Nitric acid, 60% Nitrobenzene Nitrogen dioxide Nitrotoluene Octane Octyl alcohol Pentachloroethane Pentane Phenol... 

Eastman-Halcon A process for making acetic anhydride from syngas. The basic process is the carbonylation of methyl acetate. Methanol is made directly from the carbon monoxide and hydrogen of syngas. Acetic acid is a byproduct of the cellulose acetate manufacture for which the acetic anhydride is needed. The carbonylation is catalyzed by rhodium chloride and chromium hexacarbonyl. 

Methylenebis(oxy) ]bis(2-chloroformaldehyde), see Bis (2-chloroethoxy) methane Methylene chlorobromide, see Bromochloromethane Methylene dichloride, see Methylene chloride Methylene dimethyl ether, see Methylal Methyl 2,2-divinyl ketone, see Mesityl oxide Methylene glycol, see Formaldehyde Methylene glycol dimethyl ether, see Methylal Methylene oxide, see Formaldehyde Methyl ethanoate, see Methyl acetate (1 -Methylethenyl)benzene, see a-Methylstyrene Methyl ethoxol, see Methyl cellosolve 1-Methylethylamine, see Isopropylamine (l-Methylethyl)benzene, see Isopropylbenzene Methylethyl carbinol, see sec-Bntyl alcohol Methyl ethylene oxide, see Propylene oxide ds-Methylethyl ethylene, see cis-2-Pentene frans-Methylethyl ethylene, see frans-2-Pentene Methyl ethyl ketone, see 2-Bntanone Methylethylmethane, see Butane... 

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. 

Carbomethoxytropinone. A mixture of 1.35 g of sodium methoxide (this is sodium in a minimum amount of methanol), 3.5 g of tropinone, 4 ml of dimethylcarbonate and 10 ml of toluene is refluxed for 30 min. Cool to 0° and add 15 ml of water that contains 2.5 g of ammonium chloride. Extract the solution after shaking with four 50 ml portions of chloroform, dry, evaporate the chloroform in vacuo. Dissolve the oil residue in 100 ml of ether, wash twice with a mixture of 6 ml of saturated potassium carbonate and three ml of 3 N KOH. Dry and evaporate in vacuo to recover the unreacted tropinone. Take up the oil in a solution of aqueous ammonium chloride and extract with chloroform, dry, and evaporate in vacuo to get an oil. The oil is dissolved in hot acetone, cool, and scratch inside of flask with glass rod to precipitate 2-carbomethoxytropinone. Recrystallize 16 g of this product in 30 ml of hot methyl acetate and add 4 ml of cold water and 4 ml of acetone. Put in freezer for 2 /2 to 3 hours. Filter and wash the precipitate with cold methyl acetate to get pure product. 

Figure 2. Typical hydrodynamic radius distributions (/(RjO) of individual triblock PMMA-Z>-PS-Z>-PMMA copolymer chain end-capped with oxalyl chloride in a solvent mixture of methyl acetate and acetonitrile (10/1, v/v) at 45 °C and the aggregates formed via the self-assembly of the triblock copolymer chains at 29 °C, where the triblock copolymer concentration is 1 x 10 4 g / mL.[35]...

Ultraviolet irradiation of oxadiazoline (38d) at 333.6 nm (or irradiation using benzophenone as a triplet sensitiser) gave 2-diazopropane and methyl acetate. A triplet biradical intermediate formed by cleavage of the C(OMe)—N bond was postulated <90TL863>. Oxadiazolinone (42) underwent nucleophilic attack at the carbonyl group by methyllithium to give acetate (41) after treatment of the product with acetyl chloride <89CJC1753>. 

In the first system described by Clarke, the solvent consists of the lower layer obtained after the thorough equilibration of 50 25 25 dichloroethane-methyl acetate-water. Cortisone acetate was run as the control. In the second system, hydrocortisone was used as the reference substance. The solvent consists of the lower layer obtained after the thorough equilibration of 50 25 25 methylene chloride-dioxane-water. The Rf values in the second system are cortisone acetate = 1.88, prednisone =... 

Problem 16.54 What products are formed when 1 mol of urea reacts with (a) 1 mol, (b) a second mol of methyl acetate (or acetyl chloride) ... 

Methyl chloride Methylcyclohexanol 5-Methyl-3-heptanone Methyl acetate Methyl acrylate Methyl bromide Methyl cellosolve Methyl cellosolve acetate Methyl chloroform Methyl iodide Methyl isoamyl acetate Methyl isobutyl carbinol... 

Figure 4. Profiles of volatiles for high-quality peanuts, raw and roasted (1) ethanol (2) pentane (3) 2-propanol (4) acetone (5) methylene chloride (6) methyl acetate (7) 2-methylpropanal (8) diacetyl (9) 3-methylbutanal (10) 2-methyl-butanal (11) 2,3-pentanedione (12) S-methylpyrrole (13) toluene (14) hexanal (15) 2-methylpyrazine (16) xylene (17) 2-heptanone (18) 2,5-dimethylpyrazine (19) 2-pentylfuran (20) 2-ethyl-5-methylpyrazine (21) 2-ethyl-3,6-dimethylpyra-zine (22) phenylacetaldehyde.

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