Butyl alcohol from butyric acid

Erlenmeyer found that the butyl alcohol present in fusel oil yields iso-butyric acid (see below) on oxidation, and is therefore isobutyl alcohol, and he also showed that from isobutyl iodide the same valeric acid is obtained as from the amyl alcohol of fusel oil, which is therefore isoamyl alcohol, derived from dimethylethylmethane. Secondary butyl alcohol was first obtained as hydrate de butylene from erythritol by de Luynes. A. Lieben obtained it from zinc ethyl and dichloroethyl ether, and since he found that on oxidation it gives a ketone he recognised it as secondary butyl alcohol. Lieben and A. Rossi obtained normal butyl alcohol from butyric acid, which was converted into butyraldehyde by distilling calcium butyrate and calcium formate, and a solution of this reduced with a large amount of sodium amalgam. They give structural formulae for the four butyl alcohols, with the boiling-points. 

Clofibrate Clofibrate, ethyl ether 2-(4-chloropheoxy)-M( -butyric acid (20.2.2), is synthesized by esterifying 2-(4-chlorophenoxy)-/yo-butyric acid (20.2.1) with ethyl alcohol. This is synthesized in a single-stage reaction from 4-chlorophenol, acetone, and chloroform in the presence of an alkali, evidently by initial formation of chlorethone-trichloro-tert-butyl alcohol, which under the reaction conditions is converted into (4-chlorophenoxy)trichloro-fert-butyl ether, and further hydrolyzed to the desired acid 20.2.1, which is further esterified with ethanol in the presence of inorganic acid [6-8]. 

Another oxo plant, now being constructed, will make butyl compounds (88). These may be the source of butyl alcohol, butyl acetate, butyric acid for the manufacture of cellulose acetate butyrate and other products, butyraldehyde for polyvinyl butyral, and the eight-carbon compounds including 2-ethylhexanol. All these will add to the present production of the same compounds made by the older methods from acetaldehyde via aldol condensation. 

The total yield of 201 was increased and the synthesis time reduced by extracting [nC]butyric acid from its lithium salt by dry 0.1% HCl/He gas mixture and carrying out its pyrolysis at 530 °C over glass beads (equation 104). The relative reactivity of 201 to primary, secondary and tertiary alcohols (equation 105a, b, c) has been found to be as 1 0.4 0.1, respectively. Several bioactive compounds have been labelled with [nC]propyl ketene, such as carbohydrate compounds193 and IV-butyl compounds, for instance /V- 11 C]butyryl THPO, 202, and some phorbol esters192, 203, 204 and 205. 

Mixed ethers result when alcohols and phenols are used with thoria at 390°—420° and esterification takes place when alcohol and acid interact at 350°-400°. Esterification10 is more complete in the presence of titanic oxide at 280°—300°. One molecule of acid is used with twelve molecules of alcohol, and in this way methyl, ethyl, propyl, butyl, and benzyl esters have been prepared from acetic, propionic and butyric acids. 

Oxidation of primary alcohols in acid media is often accompanied by esterification. By the use of the proper proportions of reactants, fair yields of esters may be obtained directly from the alcohols e.g., -butyl n>butyrate (47%) by chromic acid oxidation of n-butyl alcohol. Aqueous acid chlorate solutions in the presence of vanadium pentoxide have been used for this purpose. ... 

According to LaFar, Granulobacter, often called the true butyric acid bacillus or B. butylicus, possesses the faculty of storing up within its cells interior granulose. From glucose this organism produces butyl alcohol, carbon dioxide, hydrogen, and butyric acid. 

Fembach and Strange (1911) were issued the British patents 15,203-15,204 on Acetone and high alcohols (amyl, butyl, or ethyl alcohols and butyric, propionic or acetic acid) from starches, sugars, and other carbohydrates. In 1913, the first plant for the production of butanol from potatoes began in... 

Fernbach A, Strange EH (1911) Acetone and higher alcohols (amyl, butyl or ethyl alcohols and butyric, propionic or a< ic acid) from starches, sugars and other carbohydrates. British Patent 15203-15204 Fischer RJ, Helms J, Dii P (1993) Cloning, sequencing and molecular analysis of the sol operon of Clostridium acetobutylicum, a chromosomal locus involved in solventogenesis. J Bacteriol 175 6959-6969 Fond O, Jansen NB, Tsao GT (1985) A model of acetic acid and 2,3-butanediol inhibition of the growth and metabolism of Klebsiella oxytoca. Biotechnol Lett 7 727-732... 

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