From ethyl alcohol

Diethyl ether may be prepared from ethyl alcohol by the sulphuric acid process. A mixture of alcohol and sulphuric acid in equimolecular proportions is heated to about 140° and alcohol is run in at the rate at which the ether produced distils from the reaction mixture. Ethyl hydrogen sulphate (or ethyl sulphuric acid) is first formed and this yields ether either by reacting directly with a molecule of alcohol or by the formation and alcoholysis of diethyl sulphate (I) ... 

Reflux a mixture of 15 g. of homoanisamide, 30 g. of potassium hydroxide and 300 ml. of ethanol on a water bath for 5 hours. Dilute with 750 ml. of water, evaporate to 75 ml. and acidify to Congo red. Collect the acid and recrystallise it from ethyl alcohol. The yield of p-methoxy-phenylacetic acid, m.p. 86-87°, is 13 g. 

Atophan. In a 1 litre round-bottomed flask, equipped with a reflux condenser, place 25 g. (24 ml.) of purified benzaldehyde (Section IV,115), 22 g. of freshly-distilled P3 ruvic acid and 200 ml. of absolute ethyl alcohol. Heat the mixture to tlie boiling point on a water bath and add slowly, with frequent shaking, a solution of 23 g. (22 -5 ml.) of pure aniline in 100 ml. of absolute ethyl alcohol. The addition usually occupies about 1 hour. Reflux the mixture on a water bath for 3 hours, and allow to stand overnight. Filter off the crude atophan (1) at the pump and wash the crystals with a little ether. Recrystallise from ethyl alcohol (about 20 ml. per gram). The yield of pure 2-phenvlquinoUne-4-carboxvUc acid, m.p. 210°, is 30 g. 

FIGURE 15 3 The mecha nism of acid catalyzed for mation of diethyl ether from ethyl alcohol... 

From Ethyl Alcohol. Some acetaldehyde is produced commercially by the catalytic oxidation of ethyl alcohol. The oxidation is carried out by passing alcohol vapors and preheated air over a silver catalyst at 480°C (98). 

The ethyl acetate, free from ethyl alcohol, is dried with anhydrous magnesium sulfate. 

The organic phase is dried over sodium sulfate, filtered, the dichloroethane is evaporated off and the residue is crystallized from ethyl alcohol (95%). The product is dried in the oven and there is thus obtained about 800 grams (yield 90%) of the N-(2,5-diethoxyphenyl)-4-butoxy phenoxy acetamide, MP 101°C. 

Hydrobromic acid 50% w/w (325 g) diluted with water (2 liters) was added slowly at the boil and the precipitated embonic acid removed by filtering hot and washing twice with hot water (1 liter). The filtrate and washings were evaporated to dryness in a steam pan and the residue recrystallized from ethyl alcohol (1,200 ml), to yield the dibromide (320 g). 

To 3.8 grams of the base dissolved in 35 cc of ethyl alcohol is added 1.6 grams of dimethyl sulfate. The solution is allowed to stand at room temperature for about 12 hours. The salt formed is filtered, recrystallized from ethyl alcohol, and is found to have a melting point of 203° to 204°C. 

Preparation of 2-Hydroxy-4,4 -Dicyanostilbene 10 grams of 2-amino-4,4 -dicyanostilbene thus prepared were dissolved in 400 cc of boiling glacial acetic acid and 200 cc of dilute sulfuric acid added the solution was suddenly chilled and diazotized over one and a half hours at 5° to 10°C with sodium nitrate (3.0 grams/15 cc H O). The diazonium salt solution was decomposed by boiling for 15 minutes with 600 cc of 55% aqueous sulfuric acid solution the solution was diluted, cooled and filtered. The residue crystallized from ethyl alcohol as lemon yellow prismatic needles, MP 296°C. 

The common name of an ester consists of two words. The first word (methyl, ethyl,...) is derived from that of the alcohol the second word (formate, acetate,...) is the name of the acid with the -ic suffix replaced by -ate. Thus ethyl formate (Table 22.4) is made from ethyl alcohol and formic acid ... 

Diethyl chlorophosphate can also be prepared from ethyl alcohol and phosphoryl chloride in the presence of base, but the method shown is reported to give better yields. The intermediate diethyl chlorophosphate has been condensed with nitrophenol in a manner similar to that used for parathion (Equation 39). 

This procedure, coupled with the procedure described on p. 41, illustrates the Barbier-Wieland method for systematically degrading carboxylic acids. foxwor-Desoxycholic acid may be prepared from wor-desoxycholic acid by repetition of this procedure. If the chromic acid oxidation product is not sufficiently solid to filter after dilution with water, the mixture must be extracted with ether and washed with dilute hydrochloric acid before the alkaline extraction. Wxwor-Desoxycholic acid may be crystallized from ethyl alcohol. It melts at 239-241°. 

The production of fulminates (silver and mercury fulminates) from ethyl alcohol and nitric acid takes place by way of methylnitrolic acid. This question was discussed on p. 149. 

Butanol, which at one time was an unwanted by-product in the preparation of acetone, is now the most important product of the fermentation. The building of a large new factory in Puerto Rico using 10,000 tons of molasses per annum for its production is an indication of this importance. Butanol is probably still the best solvent for cellulose nitrate lacquers. Dibutyl phthalate is certainly the most widely used plasticizer for synthetic resins, and butyl oleate, tributyl citrate and dibutyl tartrate have also been described as plasticizers. Another important use of butanol is as a source of butadiene, which serves as an intermediate in the conversion of sucrose into a synthetic rubber. Although in recent years other methods have been described for the preparation of butanol (for example, from ethyl alcohol and from acetylene), yet the fermentation of carbohydrates is still the cheapest process. 

Sahcylsalicylic acid [532-94-3] (salsalate) is prepared by the action of phosphoms trichloride, phosphoms oxychloride, or thionyl chloride on salicylic acid at low temperatures in an appropriate solvent. The cmde product is recrystallized rapidly from ethyl alcohol to avoid hydrolysis and esterification. It is used as an analgesic and an antipyretic, as well as in the treatment of acute and chronic rheumatism and arthritis. It does not induce gastric disturbances because it is only slowly hydrolyzed in the intestine. Owing to the slowness of its hydrolysis (two molecules of salicylic acid per molecule of the ester), the action of sahcylsalicylic acid is less prompt but more persistent than that of other salicylates. Other salicylates of interest include ethylene glycol mono salicylate [87-28-5], dipropylene glycol monomethylether salicylate, bomyl salicylate [560-88-3], and -acetamidophenyl salicylate [118-57-0]. 

Material. Diethyl ether shall be made from ethyl alcohol conforming to the requirements... 

Other important raw material uses of ethyl alcohol are conversion to esters and ethers, vinegar, ethyl chloride, butadiene, styrene, and chloral (for DDT). Nearly all the new developments in chemicals from ethyl alcohol, particularly the four-, six-, and eight-carbon derivatives are based on alcohol derived from petroleum. The butyl alcohol and butyl acetate so made supplement the production by fermentation and from oxidation of hydrocarbons and synthesis gas operations. The consumption of ethyl alcohol for all industrial uses (denatured alcohol) exceeded 1.2 billion pounds (100% basis) in 1950. More than 700,000,000 pounds of this were made from petroleum. 

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