Normal butyl alcohol

Normal butyl alcohol, propyl carbinol, n-butanol, 1-buianol, CH3CH2CH2CH2OH. B.p. 117 C. Manufactured by reduction of crotonaldehyde (2-buienal) with H2 and a metallic catalyst. Forms esters with acids and is oxidized first to butanal and then to butanoic acid. U.S. production 1978 300 000 tonnes. 

When all the ethyl nitrite has been added, the reaction mixture is refluxed for approximately one hour, then concentrated to dryness under reduced pressure (25 to 30 mm Hg) and at a maximum temperature of 70°C. The crystalline residue is dissolved in 35 liters of water and adjusted to a pH of 8 to 9 by addition (with cooling and stirring) of 11 to 12 kg of caustic soda. The sodium chloride formed is filtered off, and the filter cake is washed with 20 liters of normal butyl alcohol. This wash liquid is used for the first extraction of the product from the aqueous filtrate. The filtrate is then further extracted with four successive 20-liter portions of n-butyl alcohol. 

Synthesis gas can be tailored in this manner to fit any number of specific applications. For example, a commercial route to aldehydes (the R-CHO signature group) and alcohols (the R-OH signature group) is the Oxo reaction, as discussed in the section on normal butyl alcohol in Chapter 14. In that reaction, the CO H2 ratio needed is I . Careful adjustment of the three feedstocks, CH4, C02, and H2O and the amount of recycling will give this combination. 

There are many other commercial alcohols besides methanol. This chapter treats the ones traded in the largest volumes ethyl alcohol, isopropyl alcohol (IPA), normal butyl alcohol (NBA), 2-ethyl hexanol (2-EH) and li4-butanediol (BDO). 

Normal butyl alcohol (NBA) was first recovered in the 1920s as a by-product of acetone manufacture via cornstarch fermentation. That route is almost extinct now. A small percent is still made from acetaldehyde. The primary source of NBA, however, is the Oxo process. 

Normal butyl alcohol + Secondary butyl alcohol... 

Hill, A.E. and Malisoff, W.M. The mutual solubility of liquids. 111. The mutual solubility of phenol and water. IV. The mutual solubility of normal butyl alcohol and water, J. Am. Chem. Soc., 48(4) 918-927, 1926. 

Available forms 203 Replacement for normal butyl alcohol in nitrocellulose lacquers, alkyd resin formulations, and thinners, distillation range 115-120C, flash p 100F (37.7C) (OC). 601 Replacement for methyl ethyl ketone in vinyl and nitrocellulose applications, distillation range 74—84C, flash p 10F (-12.2C) (OC). 

Properties Water-white, high-boiling hquid mild odor. Bp 240-250C, refr index 1.425, fp -30C, wt/ gal approximately 8.24 lb (20C), flash p 220F (104.4C) (CC). Miscible with most alcohols, ketones, esters, oils, hydrocarbons. Combustible. Derivation By the standard esterification process using normal butyl alcohol and oxalic acid. Grade According to ester content 90%, 95%, 99-100%. 

As butyl alcohol had only a restricted use, both for war and industrial purposes, ej eriments were started by Dr. Weizmann in order to develop a process for converting normal butyl alcohol into methyl-ethyl ketone which, in the pure state, is equally suitable as acetone for the manufacture of cordite. The process, which was a catalytic one, was worked out on a laboratory scale, and promised to give good yields it was decided to erect a large-scale plant at Toronto, which, however, only commenced successful operation just before the signing of the Armistice,... 

Bulk Density. Bulk density is determined by a method in which 1 g of lead azide is added incrementally to a vertical, graduated tube about 0.5 cm diam and partially filled with normal butyl alcohol. Particles adhering to the sides are washed down with butyl alcohol, addition of which is continued until the volume of material in the tube is exactly 5 ml. After standing 15 min without jarring or vibrating, the level of the lead azide column is read, calibration corrections applied, and the bulk density, calculated ftom the volume occupied, reported in g/ml. 

Propyl carbinol—Primary normal butyl alcohol—Butyl alcohol of fermentation—CHs—CHa—CHa—CHaOH—is formed in small quantities during alcoholic fermentation, and may be obtained by repeated fractional distillation from the oily liquid left in the... 

Write equations using graphic formulas by which normal butyl alcohol can be converted into (a) normal octane, ( ) normal butylene, (c) secondary butyl alcohol, (d) normal amyl alcohol, (e) normal butane, (/) butylene bromide, (g) secondary butyl bromide, (h) methylethyl ketone, (i) methyl-diethyl carbinol. 

Normal Butyl Alcohol, 1-Butanol, Butyric Alcohol, Propyl Carbinol, 1-Hydroxybutane)... 

Normal Butyl Alcohol (50% v)— Anhydrous Ethyl Alcohol (50% v) Methyl Isobutyl Carbinol (30% v)— Anhydrous Ethyl Alcohol (70% v) Methyl Isobutyl Carbinol (30% v)— Anhydrous Isopropyl Alcohol (70% v) Normal Propyl Alcohol Secondary Butyl Alcohol Normal Butyl Alcohol Methyl Isobutyl Carbinol (60% v)— Anhydrous Isopropyl Alcohol (40% v) Secondary Amyl Alcohol Amyl Alcohol (mixed isomers)... 

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. 

Kauri-butanol value Volume in ml at 25°C (77°F) of a solvent, corrected to a defined standard, required to produce a defined degree of turbidity when added to 20 g of a standard solution of kauri resin in normal butyl alcohol. For kauri-butanol values of 69 and above, the standard is toluene and has an assigned value of 105. For kauri-butanol values below 60, the standard is a blend of 75% n-heptane and 25% toluene and has an assigned value of 40. Abbreviation is KB value. Paint pigment, drying oils, polymers, resins, naval stores, cellulosics esters, and ink vehicles, vol 3. American Society for Testing and Material, Conshohocken, PA, 2001. Fhck EW (1991) Industrial synthetic resins handbook. Williams Andrews Publishing/Noyes, New York. 

Nonylene Nonylphenol Normal Amyl Alochol Normal Butyl Acetate Normal Butyl Acrylate Normal Butyl Alcohol Normal Butyraldehyde Normal Decyl Alcohol Normal Lead Acetate Normal Propyl Acetate Normal Propyl Alochol Norvalamine... 

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