Methyl acetate Methylamines

Methoxyethanol 2-Methoxyethyl acetate Methyl acetate Methyl acetoacetate Methyl acetylacetate Methyl acrylate Methylamine 2-Methylbutane 2-Methyl- 1-butanol... 

Cyclopentanone Cyanoacetic acid Ammonium acetate Hydrogen Magnesium Methyl iodide Methylamine Hydrogen chloride... 

Conventional uses of methanol account for 90% of present consumption and include formaldehyde, dimethyl terephthalate, methyl methacrylate, methyl halides, methylamines and various solvent and other applications. Newer uses for methanol that have revitalized its growth and outlook include a new technology for acetic acid, single cell protein, methyl tertiary butyl ether-(MTBE), and water denitrification. Potential uses for methanol include its use as a carrier for coal in pipelines, as a source of hydrogen or synthesis gas used in direct reduction of iron ore, as a direct additive to or a feedstock for gasoline, peak power shaving and other fuel related possibilities. Table II lists the world methanol demand by end use in 1979. 

Methanol is used as a solvent, an antifreeze, a refrigerant, and a chemical intermediate. The greatest chemical uses for methanol as of 1998 were formaldehyde, 33 percent MTBE, 27 percent acetic acid, 7 percent and chloromethane, 5 percent. Other chemicals derived from methanol include methyl methacrylate, methylamines, and dimethyl terephthalate. 

Recent computational work has suggested the existence of a mechanism for aminolysis that bypasses the tetrahedral intermediates. Transition structures corresponding to both stepwise addition-elimination through a tetrahedral intermediate and direct substitution were found for the reaction of methylamine with methyl acetate and phenyl acetate. There is considerable development of charge separation in the direct displacement mechanism because proton transfer lags rupture of the C—O bond. 

A direct substitution mechanism was indicated for the 2-pyridone catalysis of aminolysis of methyl acetate by methylamine." This mechanism is represented in Figure 7.9. It avoids a tetrahedral intermediate and describes a concerted displacement process that is facilitated by proton transfer involving 2-pyridone. Two very closely related TSs involving either the 2-hydroxypyridine or 2-pyridone tautomers were found. These TSs show extensive cleavage of the C-0 bond (2.0-2.2 A) and formation... 

Methyl acetate Methyl acetoacetatc Methylacetylacetone Methyl alcohol Methylallylaketone Methylamine N Methylanilme 9-Methylanthracene Methyl benzoate Methyl-0-benzoylbenzoatc Methylbenzylaniline Methyl bromide... 

Meroxapol 174 Meroxapol 251 Meroxapol 252 Meroxapol 254 Meroxapol 258 Meroxapol 311 Methanesulfonyl chloride Methoxymethyl isocyanate p-Methoxyphenylacetic acid Methyl acetate Methyl acetoacetate 4 -Methyl acetophenone Methylamine Methylamine, aqueous solutions Methyl anthranilate Methyl carbamate Methyl chloride 1,2-Methylenedioxybenzene N-Methylethanolamine N-Methylformamide Methyl 2-furoate 4-Methylpentanoic acid 1-Methylpiperidine 2-Methylpiperidine 3-Methylpiperidine 4-Methylpiperidine 1-Methyl-2-piperidineethanol Methyl pivalate 4-(Methylsulfonyl) acetophenone 4-(Methylthio) acetophenone... 

Common name Methylamine Acetaldehydt 5 Acetone Acetic acid Methyl acetate Acetamide Acetonitrile... 

Compound Name Methyl Acetate Propionic Acid Propionic Anhydride Methyl Mercaptan Dimethyl Sulfide Formic Acid Methyl Alcohol Hexamethylenetetramine Methoxychlor Methoxychlor Diethylebe Glycol Monomethyl Ether Methylacetylene-Propadiene Mixture Methylacetylene-Propadiene Mixture Crotonaldehyde Methyl Acrylate Methyl Formal Methyl Alcohol Methallyl Chloride Methylamine N-Methylaniline Methyl Amyl Acetate Methyl Amyl Alcohol Methyl Isobutyl Carbinol N-Amyl Methyl Ketone O-Toluidine 0-Toluidine N-Methylaniline N-Methylaniline Propyleneiniiine. 

In the field of log P calculations, the free energy methodology was applied to the water/chloroform system using Monte Carlo simulations - and to water/carbon tetrachloride using molecular dynamics simulations. Because the computer resources necessary for such calculations appear enormous, only a few log P values for small organic compounds (methylamine, dimethylamine, methanol, ethanol, propanol, dimethyl ether, acetonitrile, acetic acid, methyl acetate, acetone) were examined even in organic solvents relatively simple to model. A major source of variation between experimental and calculated log P values may lie in the assumption of the immiscibility of the two solvent systems, an assumption which is not supported experimentally. 

Mercury chloride Methane Methanol Methoxylbutanol Methyl acrylate Methyl bromide Methyl ethyl ketone Methyl glycol acetate Methyl isobutyl ketone Methyl methacrylate Methyl methyacrylate Methyl pyrrolidone Methyl salicylate Methylamine, aqueous... 

Fractionally distd under vacuum, then fractionally crystd twice from its melt. Impurities include acetic acid, methyl amine and H2O. For detailed purification procedure, see Knecht and Kolthoff, Inorg Chem 1 195 1962. Although /9-methylacetamide is commercially available it is often extensively contaminated with acetic acid, methylamine, water and an unidentified impurity. The recommended procedure is to synthesise it in the laboratory by direct reaction. The gaseous amine is passed into hot glacial acetic acid, to give a partially aq soln of methylammonium acetate which is heated to ca 130° to expel water. Chemical methods of purificatn such as extractn by pet ether, treatment with H2SO4, K2CO3 or CaO can be used but are more laborious. 

Oxime carbamates have high polarity and solubility in water and are relatively chemically and thermally unstable. They are relatively stable in weakly acidic to neutral media (pH 4-6) but unstable in strongly acidic and basic media. Rapid hydrolysis occurs in strongly basic aqueous solutions (pH > 9) to form the parent oxime/alcohol and methylamine, which is enhanced at elevated temperature. Additionally, oxime carbamates are, generally, stable in most organic solvents and readily soluble in acetone, methanol, acetonitrile, and ethyl acetate, with the exception of aliphatic hydrocarbons. Furthermore, most oxime carbamates contain an active -alkyl (methyl) moiety that can be easily oxidized to form the corresponding sulfoxide or sulfone metabolites. 

Alternatively, dissolve 220 g 4-benzyloxy-3-indoleacetic acid (or equimolar amount other indoleacetic acid) in 2 L absolute methanol and reflux six hours in the presence of 20 g Dowex 50X8 sulfonic acid resin. Filter (decolor with carbon if desired) and concentrate below 35° until precipitation starts then cool to precipitate and filter to get 200 g of the methyl ester. Add 200 g of the ester to 600 ml 40% aqueous methylamine over twelve hours with vigorous stirring. Filter, wash precipitate with water and dry to get 187 g of the N-methyl-acetamide (reflux two hours in 500 ml benzene to remove unreacted ester). 24 g of the acetamide in 300 ml tetrahydrofuran is added dropwise to 10 g lithium aluminum hydride in 300 ml tetrahydrofuran reflux ten hours, cool to 15° and add dropwise with stirring 50 ml ethyl acetate. Reflux two hours and proceed as above to get 15 g (II) or analog. 

To a mixture of 360 g 50% KOH and 138 ml methanol, add with stirring at -5° 70.5 g dimethyl ester of acetone dicarboxylic acid (dimethyl-beta-ketoglutarate — see method 3 for preparation) and let temperature rise to about 25° over V2 hour. Let stand ten minutes, cool to 0° and add 65 ml ether. Filter, wash precipitate with 65 ml ethanol and 150 ml ether at 0C to get 75 g (III). To 322 ml 1N HCI at 80c, add 41.1 g (I I) and stir twenty minutes cool to 10°, add 211 ml IN HCI, 98.2 g (Ml). 26.4 g Na acetate and 28.2 g methylamine HCI. Stir four hours at room temperature, cool to 10°, and saturate with 410 g KOH. Extract four times with methyl-Cl or benzene (75 ml each, fifteen minutes stirring) and evaporate in vacuum to get the methyl ester of tropan-3-one-2-COOH (IV), which precipitates from the oil (can distill 85/0,2). Test for activity. Dissolve 28.3 g (IV) in 170 ml 10% sulfuric acid cool to -5° and treat with 3.63 kg 1.5% Na-Hg amalgam with vigorous stirring at 0°. See below for easier methods of reducing (IV),... 

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