Acetic acid with alcohols

Fig. 14. Taft correlation with polar substituent constants (a ) of the vapour phase esterification of acetic acid with alcohols ( ) and of the olefin formation from alcohols (O) over Na-poisoned silica—alumina at 250°C [126]. 1, Methanol 2, ethanol 3, 1-propanol 4, 1-butanol 5, 2-methyl-l-propanol 6, 2-propanol 7, 2-butanol 8, 2-methyl-2-propanol.

Very ref rax live liquid strong aceth. odor. Readily combustible Fin hazard Rash pi 1WF dj I 080 mp — 73 bp 139" o I 3904 Slowly soluble in water, forming acetic acid, with alcohol forms ethyl acetate sol in chloroform, ether LDj, orally in rals 1 78 g/kg. H F Smyth el aL, Arch. tnd. Hyg. Occup Med 4. 119 ( 95l)... 

Allow a mixture of 0-5 g. of the tertiary amine and 0-5 ml. of colourless methyl iodide to stand for 5 minutes. If reaction has not occurred, warm under reflux for 5 minutes on a water bath and then cool in ice water. The mixture will generally set solid if it does not, scratch the sides of the tube with a glass rod. RecrystaUise the solid product from absolute alcohol, ethyl acetate, acetone, glacial acetic acid or alcohol-ether. 

Other Esters. The esterification of acetic acid with various alcohols in the vapor phase has been studied using several catalysts precipitated on pumice (67). 

One process (182) esterifi.es the acetic acid with ethanol (or methanol) and then converts the ester to alcohol by hydrogenolysis in the vapor phase over a copper—2inc catalyst. 

Examples are given of common operations such as absorption of ammonia to make fertihzers and of carbon dioxide to make soda ash. Also of recoveiy of phosphine from offgases of phosphorous plants recoveiy of HE oxidation, halogenation, and hydrogenation of various organics hydration of olefins to alcohols oxo reaction for higher aldehydes and alcohols ozonolysis of oleic acid absorption of carbon monoxide to make sodium formate alkylation of acetic acid with isobutylene to make teti-h ty acetate, absorption of olefins to make various products HCl and HBr plus higher alcohols to make alkyl hahdes and so on. 

Heptyl alcohol has been prepared by the reduction of heptaldehyde with zinc dust and acetic acid,i with sodium amalgam and acetic acid, with sodium in toluene and acetic acid, and with hydrogen and a platinum catalyst. Heptaldehyde has also been reduced biochemically by adding it to a fermenting sugar solution. Heptyl alcohol has been prepared by the reduction of heptoamide with sodium and amyl alcohol. ... 

In order to avoid competitive bimolecular photoreactions such as ketone reduction by hydrogen abstraction, poor hydrogen donating solvents are recommended (acetonitrile, acetic acid, tertiary alcohols). In those cases where ketene trapping is desired, solvents must also be miscible with water or other protic nucleophiles. 

The above keto-nitrile (15 grams) was methylated with a solution of diazomethane in ether. (The diazomethane solution was prepared using 20 grams of N-nitrosomethylurea.) The ether and excess diazomethane were evaporated on the steam bath and the oil dissolved in ethanol (50 ml). To this was added a solution of guanidine in ethanol (100 ml) (prepared from 8.1 grams of the hydrochloride). The solution was refluxed for 5 hours, the alcohol removed and the residue treated with 5N sodium hydroxide. The insoluble material was then filtered. After purification by precipitation from dilute acetic acid with sodium hydroxide and by recrystallization from ethanol the product formed clear colorless needles (8.0 grams), MP 218°-220°C as described in U.S. Patent 2,602,794. 

If acetic acid and alcohol are mixed in equimolecular proportions, a reaction ensues leading to the formation of an equilibrium mixture of the two substances with the ester and water. If water and the ester are mixed in equimolecular proportions, a reaction ensues leading to the equilibrium mixture of these two substances with the acid and alcohol. Thus the reaction ... 

Scheme 10.2 Esterification of acetic acid with isopentyl alcohol.

Esterification of stearic acid and acetic acid with propanol and butanol in the presence of Fe2(S04)3/KSF montmorillonite [37]. The rate enhancement observed (1.5-2.5 times) was ascribed to the higher temperature of the catalyst bed (calculated to be 9-18 K above the bulk temperature). Reaction conditions batch (no stirring) and a stirred single-mode tank reactor, catalyst particle size 5 mm, 10-fold excess of alcohol. 

Izumi and Urabe [105] found first that POM compounds could be entrapped strongly on active carbons. The supported POMs catalyzed etherization of ferf-butanol and n-butanol, esterification of acetic acid with ethanol, alkylation of benzene, and dehydration of 2-propanol [105], In 1991, Neumann and Levin [108] reported the oxidation of benzylic alcohols and amines catalyzed by the neutral salt of Na5[PV2Mo10O40] impregnated on active carbon. Benzyl alcohols were oxidized efficiently to the corresponding benzaldehydes without overoxidation ... 

As far as the velocity and the extent of the conversion are concerned, the two processes are, however, altogether different. Whereas an acid is practically instantaneously and completely converted into a salt by an equivalent amount of a sufficiently strong base (neutralisation), a process on which, indeed, alkalimetry and acidimetry depend, it is not possible to obtain from equimolecular amounts of acid and alcohol the theoretical (calculated) amount of ester. A certain maximal quantity of ester is formed, but always falls short of the theoretical, and it is impossible, even by indefinitely extending the duration of the reaction, to make the unchanged acid and alcohol produce ester in excess of that maximum. If, for example, equimolecular amounts of acetic acid and alcohol are allowed to interact in a closed system, only two-thirds of each enter into reaction, and it is impossible to induce the remaining third of acetic acid to react with that of alcohol. The maximum yield of ester therefore amounts to only two-thirds, or 66-7 per cent, of the theoretical quantity. The quantitative difference in the course of the two reactions mentioned above depends on the fact that esterification is a so-called reversible reaction , i.e. one in which the reaction products represented on the right-hand side of the equation (ester and water) also interact in the opposite direction ... 

How much ester will be formed when 3 moles of alcohol react with 1 mole of acetic acid How much when 30 g. of acetic acid and 50 g. of alcohol are used In what proportions by weight must acetic acid and alcohol be caused to interact in order to convert 75 per cent of the former into ester ... 

The R61e of the Sulphuric Acid.—If acetic acid and alcohol alone are heated together no noticeable reaction takes place even after a long time. The reaction is only started by added sulphuric acid, which may be replaced by gaseous hydrogen chloride. In all probability these mineral acids form an unstable addition compound (more likely with the acetic acid) and this compound reacts with alcohol to... 

The European Commission has mandated the European Committee for Standardization to establish a validated method of analysis for the determination of OMLs and SMLs. If a product complies with the compositional requirements of the directives, i.e., it is produced from authorized monomers and additives, then it may be tested for any desired application. If it meets the migration requirements, it is acceptable for use in cases covered by that test method. Typical food simulants used in the tests are hot water, acetic acid, ethyl alcohol and olive oil. The choice of an appropriate simulant depends on the type of food expected to come into contact with the packaging. 

Evidently the alteration of the F , values with introduction of chlorines cannot be attributed to its effect on the alteration of the strengths of the substituted acetic acids, for alcohols and esters exhibit similar changes. In order to examine the moment of the C—Cl union, some idea of the nature of its orientation at a water-air interfece must be obtained. 

Phenylacetamide has been obtained by a wide variety of reactions from benzyl cyanide with water at 250-260° 6 from benzyl cyanide with water and cadmium oxide at 240° 6 from benzyl cyanide with sulfuric acid 7 8 by saturation of an acetone solution of benzyl cyanide with potassium hydrosulfide 9 from benzyl cyanide with sodium peroxide 10 by electrolytic reduction of benzyl cyanide in sodium hydroxide 11 from ethyl phenyl-acetate with alcoholic 12 or aqueous 13 ammonia from phenyl-acetic acid with ammonium acetate 14 or urea 15 from diazoacetophenone with ammoniacal silver solution 16 from phenyl-acetic acid imino ether hydrochloride and water 17 from acetophenone with ammonium poly sulfide at 215° 18 from benzoic acid 19 and by heating the ammonium salt of phenyl-acetic acid.20... 

Acetic acid is an important industrial chemical. The reaction of acetic acid with hydroxyl-containing compounds, especially alcohols, results in the formation of acetate esters. The largest use of acetic acid is in the production ofvinyl acetate (Figure 1.1). Vinyl acetate can be produced through the reaction of acetylene and acetic acid. It is also produced from ethylene and acetic acid. Vinyl acetate is polymerized into polyvinyl acetate (PVA), which is used in the production of fibers, films, adhesives, and latex paints. 

Acetic acid with various alcohols 2-Methyl-l-propanol with various acids ... 

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