Methyl alcohol chlorination

The physical properties of methylene chloride are Hsted in Table 1 and the binary a2eotropes in Table 2. Methylene chloride is a volatile Hquid. Although methylene chloride is only slightly soluble in water, it is completely miscible with other grades of chlorinated solvents, diethyl ether, and ethyl alcohol. It dissolves in most other common organic solvents. Methylene chloride is also an excellent solvent for many resins, waxes, and fats, and hence is well suited to a wide variety of industrial uses. Methylene chloride alone exhibits no dash or fire point. However, as Htde as 10 vol % acetone or methyl alcohol is capable of producing a dash point. 

Chloroform can be manufactured from a number of starting materials. Methane, methyl chloride, or methylene chloride can be further chlorinated to chloroform, or carbon tetrachloride can be reduced, ie, hydrodechlorinated, to chloroform. Methane can be oxychlorinated with HCl and oxygen to form a mixture of chlorinated methanes. Many compounds containing either the acetyl (CH CO) or CH2CH(OH) group yield chloroform on reaction with chlorine and alkali or hypochlorite. Methyl chloride chlorination is now the most common commercial method of producing chloroform. Many years ago chloroform was almost exclusively produced from acetone or ethyl alcohol by reaction with chlorine and alkali. 

The early sources of phenol were the destructive distillation of coal and the manufacture of methyl alcohol from wood. In both cases, phenol was a by-product. Recovered volumes were limited by whatever was made accidentally in the process. Initial commercial routes to on-purpose phenol involved the reaction of benzene with sulfuric acid (1920), chlorine (1928), or hydrochloric acid (1939) all these were followed by a subsequent hydrolysis step (reaction with water to get the -OH group) to get phenol. These processes required high temperatures and pressures to make the reactions go. They re multistep processes requiring special metallurgy to handle the corrosive mixtures involved. None of these processes is in commercial use today. 

Sodium hydroxide, Nitromethane, Chlorine gas, Calcium chloride Phosphorous trichloride, Aluminum chloride, Methyl chloride, Methylene chloride, Hydrochloric acid, Isopropyl alcohol, Toluene, Pyridine, Calcium chloride Sodium cyanide, Carbon tetrachloride, Ethyl alcohol, Chlorine gas... 

The tinctura iodi of the British Pharmacopoeia is a soln. of half an ounce of iodine, and a quarter of an ounce of potassium iodide in a pint of rectified spirit. P. Wantig found the mol. ht. of soln. —1 941 Cals., and S. U. Pickering —1 714 per 880 mol. of ethyl alcohol. C. Lowig found that alcoholic tincture of bromine is slowly decomposed in darkness, rapidly in light. Alcoholic soln. of iodine, according to H. E. Barnard, are stable in light and in darkness, but according to J. M. Eder they decompose 1000 times more slowly than chlorine water under similar conditions T. Budde has shown that hydriodic acid, acetic ester, and aldehyde are formed, and the electrical conductivity of the soln. increases. J. H. Mathews and E. H. Archibald and W. A. Patrick found a freshly prepared AT-soln. to have an electrical conductivity of 2 4 XlO-6 reciprocal ohms and a sat. soln., 1 61 X10 4 reciprocal ohms at 25°. The decomposition is accelerated by the presence of platinum. The heat of soln. decreases with concentration from —7 92 to —7 42 cals, respectively for dilute and sat. soln. in methyl alcohol, and likewise from —4 88 to —5 22 cals, for similar soln. in ethyl alcohol. The solubility of iodine in aq. soln. of propyl alcohol is not very different from that in ethyl alcohol. 

Methylene dichloride and chloroform may be produced by modified methods using a mixture of chlorine, methane, and methyl chloride as feed. Chlorination is run at 350-400°C reactor temperature at slightly above atmospheric pressure. A 2.6 1 chlorine methane ratio results in an optimal yield of chloroform. Alternatively, excess methane is reacted with chlorine at 485-510°C to produce methylene dichloride as the main product.181 The predominant method, however, still is the chlorination of methyl chloride manufactured by the reaction of methyl alcohol and hydrogen chloride.181... 

Thiotrithiazyl Iodide, N3S4I, may be prepared by dissolving thiotrithiazyl chloride in ice-cold water and adding excess of an ice-cold solution of potassium iodide. It is also formed by the action of iodine dissolved in methyl alcohol on thiotrithiazyl chloride, but prepared in this way it is invariably contaminated with chlorine. It is a dark red crystalline powder which decomposes spontaneously with evolution of iodine on exposure to air.3... 

Trinitroanisol may also be prepared by the interaction of methyl iodide and silver picrate, and by the nitration of anisic acid, during which the carboxyl group is lost, but the most convenient method appears to be that of Jackson70 and his collaborators by which a methoxy group is substituted for chlorine in a nucleus already nitrated. A methyl alcohol solution of picryl... 

Toxic solvents, such as methyl alcohol, benzene, and chlorinated hydrocarbons, can penetrate the skin through cuts and abrasions. On contact, these solvents cause chronic dermatitis and allergic skin reactions in susceptible individuals. 

Methylchloride. Industrially it is obtained by chlorinating methane or reacting methyl alcohol with hydrogen chloride in the presence of dehydrating substances. 

In an electrostatic potential map, the color red indicates regions of a molecule that are electron-rich. The map shows that chlorine is the most electronegative atom in methyl alcohol, and the direction of polarity of the C-Cl bond is ... 

From Methyl Formate By chlorination of methyl formate, obtained from methyl alcohol and formic acid according to the equation ... 

A small quantity, about 10 ml., of methyl chloroformate is placed in a flask fitted with a tap-funnel, a tube to introduce the phosgene and an exit tube, and after cooling to 0° C. a current of chlorine-free phosgene is bubbled in. Methyl alcohol is added from the tap-funnel, after a time, in volume about one-third of that of the liquid in the flask, this addition being made all at once. The addition of a fresh quantity of methyl alcohol is made when it is obvious that the phosgene is no longer being absorbed. The total quantity of methanol used should preferably not exceed 150 ml. 

Methyl phenylarsinate, C6H5.AsO(OCH3)2, is a colourless liquid, B.pt. 188° C. at 95 mm., density 1-8946 at 23° C. it is readily decomposed by water to the acid and methyl alcohol. The ethyl ester boils at 168° to 170° C. at 16 mm., density 1-318 at 15 C. When treated with chlorine it yields phenylliydroxychloroarsinc, chloral, and hydrogen chloride. ... 

Such a compound, however, if produced by the action of chlorine upon methyl alcohol, evidently splits off hydrochloric acid and yields an aldehyde, as follows ... 

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