Butyl, 77 alcohol

Uses n-Butyl alcohol is used extensively in a number of industries. For instance, it is used as a solvent in industries associated with the manufacture of paints, varnishes, synthetic resins, gums, pharmaceuticals, vegetable oils, dyes, and alkaloids. n-Butyl alcohol also finds use in the manufacture of artificial leather, rubber, and plastic cements, shellac, raincoats, perfumes, and photographic films. 

Toxicity n-Butyl alcohol is a highly refractive liquid and bums with a strongly luminous flame. Exposure to n-Butyl alcohol causes irritation to the eyes, nose, throat, and respiratory system. Prolonged exposure results in symptoms of headache, vertigo, drowsiness, comeal inflammation, blurred vision, photophobia, and cracked skin. It is advised that workers coming in contact with n-Butyl alcohol should use protective clothing and barrier creams.2107108 

Propylene and synthesis gas give //-butyl alcohol iso-butyl alcohol is a by-product. 

Oberly R, Tansy MF LC50 values for rats acutely exposed to vapors of acrylic and methacrylic acid esters, jf Toxicol Environ Health 16 811, 1985 

Carpenter CP et al Range-finding toxicity data List VUl. Toxicol Appl Pharmacol 28 313, 1974 

Englehardt G, KlimischJJ -Butyl acrylate monomer Cytogenetic investigations in the bone marrow of Chinese hamsters and rats after 4-day inhalation. Fundam Appl Toxicol 3 640, 1983 

DePass LR et al Acrylic acid, ethyl acrylate, and butyl acrylate Dermal oncogenicity bioassays of acrylic acid, ethyl acrylate, and butyl acrylate. J Toxicol Environ Health 14 115-120, 1984 

Reininghaus W, Koestner A, Klimisch HJ Chroic toxicity and oncogenicity of inhaled methyl acrylate and w-butyl acrylate in Sprague-Dawley rats. Food Chem Toxicol 29 329-339, 1991 

Synonyms 2-methyl-2-propanol trimethyl carbinol fert-bntanol 

Acute oral LD50 value (rats) 3500 mg/kg Exposure Limits 

Flammable liquid, flash point 9°C (48°F) autoignition temperature 478°C (892°F) presents a Are hazard in contact with heat or flame vapor forms explosive mixtures with air, LEL and UEL values 2.4 and 8.0% by volume of air, respectively. It may react violently with strong oxidizers. 

When added to a cold aqueous solution of NaOH and passing chlorine into the mixture it forms ferf-butyl hypochlorite. 

---

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

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. 

Tertiary butyl alcohol, trimethyl carbinol, tertiary butanol. 2-methyl-2-propanol, Me3COH. Colourless prisms, m.p. 25°C, b.p. 83°C. Prepared by absorbing isobutene (2-methylpropene) in sulphuric acid, neutralizing and steam distilling the liquor. Converted to isobutene by heating with oxalic acid. Potassium-/-buloxide is a very strong base. 

The tendency to separate is expressed most often by the cloud point, the temperature at which the fuei-alcohol mixture loses its clarity, the first symptom of insolubility. Figure 5.17 gives an example of how the cloud-point temperature changes with the water content for different mixtures of gasoline and methanol. It appears that for a total water content of 500 ppm, that which can be easily observed considering the hydroscopic character of methanol, instability arrives when the temperature approaches 0°C. This situation is unacceptable and is the reason that incorporating methanol in a fuel implies that it be accompanied by a cosolvent. One of the most effective in this domain is tertiary butyl alcohol, TBA. Thus a mixture of 3% methanol and 2% TBA has been used for several years in Germany without noticeable incident. 

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. 

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. 

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 [Pg.261]

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. 

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 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... 

In a 250 ml. separatory funnel place 25 g. of anhydrous feri.-butyl alcohol (b.p. 82-83°, m.p. 25°) (1) and 85 ml. of concentrated hydrochloric acid (2) and shake the mixture from time to time during 20 minutes. After each shaking, loosen the stopper to relieve any internal pressure. Allow the mixture to stand for a few minutes until the layers have separated sharply draw off and discard the lower acid layer. Wash the halide with 20 ml. of 5 per cent, sodium bicarbonate solution and then with 20 ml. of water. Dry the preparation with 5 g. of anhydrous calcium chloride or anhydrous calcium, sulphate. Decant the dried liquid through a funnel supporting a fluted Alter paper or a small plug of cotton wool into a 100 ml. distilling flask, add 2-3 chips of porous porcelain, and distil. Collect the fraction boiling at 49-51°. The yield of feri.-butyl chloride is 28 g. 

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. 

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... 

The small capacity apparatus is especially recommended for the use of students the consumption of iodine by a large class of students is not unreasonably high. Larger apparatus, e.g., 60 ml. and 100 ml. capacity holding 100 g. and 200 g. respectively of iodine, are generally preferred for routine preparations of alkyl iodides the bolt-head flask should then be of 250 or 500 ml. capacity. Thus for n-butyl iodide a typical preparation would employ 120 g. (148-5 ml.) of n.butyl alcohol, 21 75 g. of red phosphorus, and 200 g. of iodine. 

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. 

---