1911 Encyclopædia Britannica/Amyl Alcohols

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AMYL ALCOHOLS (C5HuOH). Eight amyl alcohols are known: normal amyl alcohol CH3-(CH2)4-OH, isobutyl carbinol or isoamyl alcohol (CH3)2-CH-CH2~CH2OH, active amyl alcohol (CH3)(C2H5):CH-CH2()H, tertiarybutylcarbinol(CH3)3C-CH2OH, diethyl carbinol (C2H5)2CH-OH, methyl (n) propyl carbinol (CH4-CH? CHQ) (CH3):CH:OH, methyl isopropyl carbinol (CH3)2:CH(CH3):CHOH, and dimethyl ethyl carbinol (CH,)2-(C, H5);C~OH. Of these alcohols, the first four are primary, the last one a. tertiary, the other three secondary alcohols; three of them, viz. active amyl alcohol, methyl (n) propyl carbinol, and methyl isopropyl carbinol, contain an asymmetric carbon atom and can consequently each exist in two optically active, and one optically inactive form. The most important is isobutyl carbinol, this being the chief constituent of fermentation amyl alcohol, and consequently a constituent of fusel (q.v.) oil. It may be separated from fusel oil by shaking with strong brine solution, separating the oily layer from the brine layer and distilling it, the portion boiling between 1 2 5° and 14o°C. being collected. For further purification it may be shaken with hot milk of lime, the oily layer separated, dried with calcium chloride and fractionated, the fraction boiling between 128° and 132°C. only being collected. It may be synthetically prepared from isobutyl alcohol by conversion into isovaleryl-aldehyde, which is subsequently reduced to isobutyl carbinol by means of sodium amalgam.

It is a colourless liquid of specific gravity 0-8248 (o°C.), boiling at I3I'6°C., slightly soluble in water, easily soluble in alcohol, ether, chloroform and benzene. It possesses a characteristic strong smell and a sharp burning taste. When perfectly pure, it is not a poison, although the impure product is. On passing its vapour through a red-hot tube, it undergoes decomposition with production of acetylene, ethylene, propylene, &c. It is oxidized by chromic acid mixture to isovaleryl-aldehyde; and it forms crystalline addition compounds with calcium and stannic chlorides.

The other amyl alcohols may be obtained synthetically. Of these, tertiary butyl carbinol has been the most difficult to obtain, its synthesis having only been accomplished in 1891, by L. Tissier (Comptes Rendus, 1891, 112, p. 1065) by the reduction of a mixture of trim ethyl acetic acid and trimethylacetyl chloride with sodium amalgam. It is a solid whichkmelts at 48°-50° C. and boils at II2'3° C.

AMYL NITRITE (isoamyl nitrite), C5Hu-ONO, a liquid prepared by passing nitrous fumes (from starch and concentrated nitric acid) into warm isoamyl alcohol; or by distilling a mixture of 26 parts of potassium nitrite in 1 5 parts of water with 30 parts of isoamyl alcohol in 30 parts of sulphuric acid (Renard, Jahresb., 1874, p. 352). It is a yellow-coloured liquid of speciic gravity 0-877, boiling at about 95°-96° C. It has a characteristic penetrating odour, and produces marked effects on the system when its vapour is inhaled. It is insoluble in water, but dissolves readily in alcohol, ether, glacial acetic acid, chloroform and benzene. On heating with methyl alcohol it is converted into isoamyl alcohol, methyl nitrite being produced at the same time; a similar reaction takes place with ethyl alcohol, but the change is less complete. It is readily decomposed by nascent hydrogen, with the formation of ammonia and isoamyl alcohol; and on hydrolysis with caustic potash it forms potassium nitrite and isoamyl alcohol. When the liquid is dropped on to fused caustic potash, it forms potassium valerate. Amyl nitrite finds application in medicine, and in the preparation of anhydrous diazonium salts (E. Knoevenagel, Berichte, 1890, 23, p. 2094).

AMYMONE, in ancient Greek legend, daughter of Danaiis. With her sisters, she had been sent to look for water, the district of Argos being then parched through the anger of Poseidon. Amymone having thrown her spear at a stag, missed it, but hit a satyr asleep in the brake. The satyr pursued her, and she called for help on Poseidon, who appeared, and for love of her beauty caused a spring to well up, which received her name. Aeschylus wrote a satyric drama on the subject. By the god Amymone became the mother of Nauplius, the Wrecker. Her meeting with Poseidon at the spring is frequently represented on ancient coins and gems.

Apollodorus ii. I, 4; Hyginus, Fab. 169; Properties ii. 26. AMYNTAS I., king of Macedonia (c. 540-498 B.c.), was a tributary vassal of Darius Hystaspes. With him the history of Macedonia may be said to begin. He was the first of its rulers to have relations with other countries; he entered into. an alliance with the Peisistratidae, and when Hippias was driven out of Athens he offered him the territory of Anthemus on the Thermaic Gulf, with the object of turning the Greek party feuds to his own advantage (Herodotus v. 17, 94; Justin vii. 2; Thucydides ii. 100; Pausanias ix. 40). See MACEDONIAN EMPIRE. AMYNTAS II. (or III.), son of Arrhidaeus, great-grandson of Alexander I., king of Macedonia from 393 (or 389) to 369 B.C.