Butyl, 77 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. 

Secondary butyl alcohol, methylethyl car-binol, 2-butanol, CH3CH2CH(Me)OH. B.p. I00°C. Manufactured from the butane-butene fraction of the gas from the cracking of petroleum. Used to prepare butanone. 

Place 92 5 g. (114 5 ml.) of n-butyl alcohol and 8 55 g. of purified red phosphorus (Section 11,50,5) in a 500 ml. round-bottomed flask (attached at C) and 100 g. (32 ml.) of bromine in A. Pass a stream of cold water through the condenser F and through the double surface condenser fitted at D the condenser F prevents the volatilisation of the alcohol from the 

Divide the saturated solution of n-butyl alcohol in water into three approximately equal parts. Treat these respectively with about 2-5 g. of sodium chloride, potassium carbonate and sodium hydroxide, and shake each until the soli have dissolved. Observe the effect of these compounds upon the solubility of n-butanol in water. These results illustrate the phenomenon of salting out of organic compounds, t.e., the decrease of solubility of organic compounds in water when the solution is saturated with an inorganic compound. The alcohol layer which separates is actually a saturated solution of water in n-butyl alcohol. 

Carry out the Lucas test with iso-propyl alcohol, n-butyl alcohol, scc.-butyl alcohol, cycZohexanol and iert.-butyl alcohol. Obtain an unknown alcohol from the instructor for test. 

Series reactions occur in which the tert-butyl hydrogen sulfate reacts to unwanted tert-butyl alcohol  

The commercial constant boiling point alcohol, b.p. 80°/760 mm., containing 88 per cent, of tert..butyl alcohol, may be used 28-5 g. are required. 

Shake 1 ml. of anhydrous methyl alcohol with 1 ml. of paraffin oil. Repeat the experiment with 1 ml. of n butyl alcohol. From your results state which is the better solvent for paraffin oil (a mixture of higher hydrocarbons) and thus explain why n-butanol and higher alcohols are incorporated in pyroxylin lacquers in preference to methyl and ethyl alcohols. 

Obtain five small dry test-tubes (75 x 10 mm. ) and introduce 1 ml. of the following alcohols into each ethyl alcohol, n-butyl alcohol, jcc.-butyl alcohol, cycZohexanol and reactivity towards sodium. 

Reflux a mixture of 68 g. of anhydrous zinc chloride (e.g., sticks), 40 ml. (47 -5 g.) of concentrated hydrochloric acid and 18-5 g. (23 ml.) of sec.-butyl alcohol (b.p. 99-100°) in the apparatus of Fig. 777, 25, 1 for 2 hours. Distil oflF the crude chloride untU the temperature rises to 100°. Separate the upper layer of the distillate, wash it successively with water, 5 per cent, sodium hydroxide solution and water dry with anhydrous calcium chloride. Distil through a short column or from a Claisen flask with fractionating side arm, and collect the fraction of b.p. 67-70° some high boiling point material remains in the flask. Redistil and collect the pure cc. butyl chloride at 67-69°. The yield is 15 g. 

Fit up the apparatus shown in Fig. Ill, 31, 1 the capacity of the Claisen flask should be 100 ml. Place 40 g. (24-6 ml.) of redistilled thionyl chloride in the flask and 60 g. (62 ml.) of dry n-butyl alcohol (b.p. 116-117°) in the dropping funnel. Cool the flask in ice and add the n-butyl alcohol, with frequent shaking, over 1 hour (1). Reflux the mixture gently for 1 hour to complete the reaction and to remove the residual hydrogen chloride. Arrange the apparatus for distillation, and distil under normal pressure until the temperature rises to 120° then distil under diminished pressure (Fig. 11, 20, 1) and collect the di-n-butyl sulphite at 116-118°/20 mm. The yield is 66 g. 

The student will doubtless be aware of the fact that methyl, ethyl, n-propyl and iso propyl alcohols are completely miscible with water. The solubilities of the higher aloohols decrease progressively as the carbon content increases. The solubilities of all types of alcohols with five carbon atoms or more are quite small. For the isomeric butyl alcohols the solubilities (g. per 100 g. of water at 20°) are n-butyl, 8 iso-butyl, 23 scc.-butyl, 13 ierl.-butyl, completely miscible. 

Fit a 500 ml. round-bottomed flask with a dropping funnel and a double surface condenser alternatively, the flask may be provided with a two-way addition tube (Fig. II, 13, 9) and the dropping funnel and condenser inserted into the latter. Place 37 g. (46 ml.) of iso-butyl alcohol (b.p. 106-108°) and 40 g. (41 ml.) of pure pyridine in the flask and 119 g. (73 ml.) of redistilled thionyl chloride in the dropping funnel. Insert a cotton wool or calcium chloride guard tube into the mouth of the funnel. Introduce the thionyl chloride during 3-4 hours a white solid 

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