Acetic acid from ethyl alcohol

Commercially, these acids are produced in several ways (I) oxidation of relevant alcohol—e.g.. acetic acid from ethyl alcohol (2) oxidation of relevant aldehyde—e g. acetic acid from acetaldehyde (3) bacterial... 

Manufacture of acetic acid from ethyl alcohol... 

Nitrodiphenylamine-6 -arsinic acid, obtained when p-bromo-nitrobenzene is used in the foregoing, crystallises from acetic acid or ethyl alcohol in yellow prisms, possessing similar properties to the preceding acids. 

Ethyl acetate is to be produced from the acetic acid and ethyl alcohol feed used in the illustrations of Secs. 14.1 and 14.2. If the feed and the product streams are both at 100°C, and 37.2 percent of the acid is converted to the ester, determine the total heat input into any reactor to produce 2500 kg of the ester. Show that this heat input is equivalent to that obtained in the illustrations in the previous sections. 

Esters can be thought of as the result of removing one molecule of water from a carboxylic As we will see in Section 28-6, one acid and an alcohol. Removing a molecule of water from acetic acid and ethyl alcohol method of forming esters involves gives ethyl acetate acid-catalyzed reaction of an alcohol... 

The kinetics of the formation of ethyl acetate from acetic acid and ethyl alcohol as homogeneously catalyzed by a constant amount of HCl has been studied by titrating 1-cc aliquots of the reaction mixture with 0.0612 N base at various times. The data presented in Table Pl-3 have been obtained at 25°C [15]. 

The ester formation process involves excision of a water molecule from acetic acid and ethyl alcohol, as in the following drawing ... 

Step polymerizations involve successive reactions between pairs of mutually-reactive functional groups which initially are provided by the monomer(s). The number of functional groups present on a molecule of monomer (i.e. its functionality) is of crucial importance, as can be appreciated by considering the formation of ester linkages from the condensation reaction of carboxylic acid groups with hydroxyl groups. Acetic acid and ethyl alcohol are monofunctional compounds which upon reaction together yield ethyl acetate with elimination of water... 

Alcohol to acetic acid Aldehydes to alcohols (e.g., acetaldehyde to ethyl alcohol) Starch to glucose Hexose phosphate from hexose and phosphoric acid... 

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 ... 

The conversion of ethyl alcohol by way of acetaldehyde into acetic acid is the chemical expression equivalent to acetic fermentation. In this process the acetic bacteria utilise atmospheric oxygen in order to bind the hydrogen. That the hydrogen which has to be removed is activated, and not the oxygen (as was formerly thought), is shown by experiments in which oxygen is eaxluded and replaced by quinone the bacteria produce acetic acid from alcohol as before and the quinone is reduced to hydroquinone. 

Twenty-five years ago the only oxygenated aliphatics produced in important quantities were ethyl and n-butyl alcohols and acetone made by the fermentation of molasses and grain, glycerol made from fats and oils, and methanol and acetic acid made by the pyrolysis of wood. In 1927 the production of acetic acid (from acetylene) and methanol (from synthesis gas) was begun, both made fundamentally from coal. All these oxygenated products are still made from the old raw materials by the same or similar processes, but the amount so made has changed very little in the past quarter century. Nearly all the tremendous growth in the production of this class of compounds has come from petroleum hydrocarbons. 

W. Traube described the formation of what he called sulphimide, along with ammonia and imidosulphonic acid, when sulphamide is heated at 200°-210°. The solid product is treated with water, the soln. mixed with silver nitrate, and the precipitated silver sulphimide, purified by recrystallization, is decomposed with dil. hydrochloric acid. The aq. soln. decomposes when the attempt is made to isolate the solid, for when the soln. is evaporated below 40°, only ammonium hydrosulphate remains. A. Hantzsch and A. Holl found the soln. in ethyl acetate has properties in accord with the trimolecular formula sulphucyl trumide, or trisulphimide, (S02.NH)3—e.g. ebulliscopic determinations of the mol. wt. and the electrical conductivities of the aq. soln. of trisulphimide and its salts. They were able to isolate a crystalline solid by crystallization from ethyl alcohol which they considered to be trisulphimide itself. A. Hantzsch and B. C. Stuer, however, showed that the alleged compound is extremely unstable, and that the soln. obtained by W. Traube, and the solid obtained by A. Hantzsch and A. Holl, was really sulphuryl imidodiamide, only indications of the transient formation of trisulphimide in non-aqueous solvents were obtained. Trisulphimide acts as an acid, and a few salts have been reported. A. Hantzsch and B. C. Stuer consider that the compound has tautomeric forms—a true imide and an acid ... 

Ethyl acetate (boiling point 77.1, density 0.9005, flash point -4°C) is manufactured from ethyl alcohol and acetic acid. 

A more recent process allows the manufacture of ethyl acetate from ethyl alcohol without the use of acetic acid or any other cofeedstocks. In the process (Fig. 1), ethyl alcohol is heated and passed through a catalytic dehydrogenation reactor where part of the ethyl alcohol is dehydrogenated to form ethyl acetate and hydrogen. 

Ethyl acetate, which is a comparatively small molecule, has the typical fruity character associated with all the lower esters, and a more or less equal balance between the influence of the two structural units, derived from ethyl alcohol and acetic acid. Linalyl acetate and geranyl acetate, however, although retaining the typical character of an acetate have much less of the ester fruitiness and are more closely related to the corresponding alcohols, linalool, and geraniol. The dominance of the alcohol appears to be even greater in phenylethyl acetate and paracresyl acetate (a phenolic ester). 

A considerable wood hydrolysis industry with rather old traditions is located in the Soviet Union. The main fermentation product based on hexoses in wood hydrolyzates is ethyl alcohol, but pentoses and aliphatic acids can also be utilized in the production of proteins (see Section 10.2.3). A variety of chemicals, including ethylene, ethylene oxide, acetaldehyde, and acetic acid, can be produced from ethyl alcohol. One interesting future application of ethyl alcohol concerns its use as a motor fuel mixed with gasoline (gasohol). 

When the mixture used in the preparation of the preceding acid (Method 3) is heated at 160° to 170° C., only a small quantity of diphenylamine-o-arsinic acid results, the main product being triphenylamine-o-arsinic acid. This acid crystallises from ethyl alcohol in colourless, prismatic crystals, decomposing at 150° C. It is easily soluble in warm alcohols, very sparingly soluble in water, and insoluble in ether and acetone. Its acetic acid solution is coloured intense greeir on the addition of a little nitric acid. 

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