1- -butylamine

Submitted by Kenneth N. Campbell, Armiger H. Sommers, and Barbara K. Campbell. 

2-Dimethylethylenimine. A cold mixture of 110 g. (60 ml., 1.06 moles) of concentrated sulfuric acid and 200 ml. of water is added in portions, with shaking, to a solution of 100 g. (107 ml., 1.12 moles) of 2-amino-2-methyl-l-propanol in 200 ml. of water contained in a 1-1. round-bottomed flask (Note 1). The flask is fitted with a thermometer extending into the liquid and a short still head carrying a downward condenser. 

Water is distilled from the mixture at atmospheric pressure until the temperature of the solution reaches 115° (Notes 2 and 3) whereupon the liquid is transferred to a 500-ml. round-bottomed flask. This flask is connected to the distillation apparatus used previously except that the thermometer is replaced by a capillary tube. Distillation is then continued under the reduced pressure obtainable from a water aspirator. The bath temperature is raised to 175° over a period of about an hour and is held there until the mixture solidifies (usually 30-60 minutes longer), and for 1 hour thereafter. The flask is cooled and broken to remove the product. 

The brown solid from the above operations is ground in a mortar and placed in a 500-ml. distilling flask equipped with a downward condenser and a reeeiver. A cold solution of 100 g. 

The organic layer is separated from the drying agent and distilled from a few fresh pellets of potassium hydroxide through a column of the Whitmore-Fenske type. After a 3- to 5-g. forerun, the product distils at 71-72° the yield is 36-41 g. (45-51%) (Notes 4 and 5). 

Plastics, lacquers, cellulose esters, fruit essences, perfumes, and chemical intermediates additive to unleaded gasoline 

Toxicology. At high concentrations tert-butyl alcohol causes narcosis in animals, and it is expected that severe exposure in humans will result in the same effect with repeated exposures in rodents the urinary tract is the primary target. 

In humans, heavy exposure may cause irritation of the eyes, nose, and throat headache nausea fatigue and dizziness. Systemic effects have not been reported. Application of tert-butyl alcohol to skin causes slight erythema and hyperemia.  

Signs of intoxication in rats were ataxia and narcosis the oral LDso was 3.5g/kg. In a 90-day study in F344 rats and B6C3F1 mice, 

Increased kidney weights that correlated with increased chronic nephropathy occurred in male mice and rats exposed by inhalation to concentrations up to 2100ppm for 13 weeks.  

Isopropylamine is used as a dehairing agent and as an intermediate in the preparation of 

Colorless volatile liqnid with an odor of ammonia density 0.694 at 15°C (59°F) boils at 33-34°C (91-93°F) freezes at -lOLC ( 149°F) soluble in water, alcohol, and ether strongly alkaline. 

Isopropylamine is a strong irritant to the eyes, skin, and respiratory system. A short exposure to 10-20 ppm can canse irritation of the nose and throat in hnmans (Proctur and Hughes 1978). Prolonged exposure to high concentrations may lead to pnlmonary edema. Skin contact can canse dermatitis and skin bums. Exposure to 8000 ppm for 4 hours was lethal to rats. 

LD50 value, oral (mice) 2200 mg/kg Exposure Limits 

Highly flammable hquid flash point (closed cup) -37°C (-35°F), open cup -26°C (—15°F) vapor pressure 478 torr at 20°C (68°F) vapor density 2.0 (air = 1), the vapor is heavier than air and can travel some distance to a source of ignition and flashback autoignition temperature 402°C (756°F) fireextinguishing agent dry chemical, CO2, or alcohol foam use water to keep fire-exposed containers cool and to flush and dilute the spiU. 

Refractive index at 20 C Viacoeity at 2S C Vapor preeeure at 20 0 Weight per gallon at 20 C Add insoluble l UllaUon range IniUal boiling point Not leae than 06% 

Butyl acrylate is mainly used to produce acrylic polymers. About 40% of these polymers are used by the coatings industry, while another quarter of this chemical is reacted with the ethylene to produce a copolymer. Another 18% is used by the adhesives industry, and an additional 8% is used to make textiles. 

The f-butylamine reacts with sodium MBT intermediate to produce TBBS accelerator for rubber. 

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Fowkes and Harkins reported that the contact angle of water on paraffin is 111° at 25°C. For a O.lAf solution of butylamine of surface tension 56.3 mJ/m, the contact angle was 92°. Calculate the film pressure of the butylamine absorbed at the paraffin-water interface. State any assumptions that are made. 

Cool the solution in ice while the alkali hydroxide is dissolving some ammonia gas is evolved. When the potassium hydroxide has dissolved, separate the amine, and dry it for 24 hours over sodium hydroxide pellets. Filter into a Claisen flask and distil. Collect the di-n-butylamine at 157-160°. The yield is 31 g. 

These two vibrations are clearly visible at 3270 and 3380 cm in the IR spectrum of butylamine shown in Figure 22 la Secondary amines such as diethylamme shown m Figure 22 7i> exhibit only one peak which is due to N—H stretching at 3280 cm Ter tiary amines of course are transparent m this region because they have no N—H bonds... 

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