Butyl compounds, Butyl alcohols
Butyl group consists of the group of atoms C4H9- . It is derived by removing one hydrogen atom from either of the isomers of butane, C4H10, and exists in four isomeric forms. Two isomers of butane exist, n-butane, also called 1–butane (CH3CH2CH2CH3), and iso-butane, also called 2-methylpropane (CH3CH(CH3)CH3).
Removing a hydrogen atom from the first isomer can result in the formation of two different butyl groups, one designated as n-butyl, and the other as sec-butyl (secondary butyl). The structure of the n-butyl group is CH3CH2CH2CH2- ; the structure of the sec-butyl group is 2 CH3CH CH(CH - 3) . The difference is that the n-butyl group
|n–butyl acetate||manufacture of photographic film, safety glass, artificial leather, perfumes, and flavoring agents|
|N–butyl pthalate||insect repellant|
|n–butyltrichlorosilane||production of silicones|
|4–tert–butyl catechol||used to slow down or stop polymerization reactions in the production of certain plastics and synthetic rubbers|
|butylate (bis [2–methyl–propyl] carbamothoic acid S–ethyl ester) herbicide t–butyl acetate||gasoline additive|
|4–tert–butylphenyl salicylate||light absorber in plastic food wrappings|
|n–butylamine||raw material in the synthesis of many products, including dyes, pharmaceuticals, insecticides, and rubber chemicals|
|sec–butylamine||prevents the growth of fungi|
|n–butyl citrate||anti–foaming agent; plasticizer; manufacture of inks and polishes|
|1–butyl–3–metanilyurea||treatment of hypoglycemia (an abnormally low blood sugar level)|
|butylmethoxydibenzoyl–methane||screens out ultraviolet light|
|t–butyl nitrate||jet propellant|
|n–butyl strearate||used to soften cosmetics, plastics, textiles, and other types of polymers|
bonds to other atoms via an end carbon atom, while the sec-butyl group bonds via an "inner" carbon atom.
Removal of a hydrogen atom from the iso-butane isomer can result in the formation of two different butyl groups. One of these groups is commonly known as tertbutyl or 1, 1-dimethylethyl [(CH3)3C- ]. The tertprefix stands for tertiary, indicating that the open bond is from a carbon atom that is attached to three other carbon atoms. The other butyl group that can be formed from iso-butane is the isobutyl or 2-methylpropyl group [(CH3)2CHCH2- ].
A large number of compounds containing the butyl group exist. Many of them are relatively simple and can be represented by the formula C4H9X, where X stands for a halogen, a hydroxyl group, an amine, or some other group. The following sections review some of the most important of these compounds.
Four butyl alcohols exist, each formed by the addition of a hydroxyl group (OH) to one of the four butyl isomers discussed above. Their names and structures are as follows: n-butyl alcohol (or 1-butanol) CH3CH2CH2CH2OH; iso-butyl alcohol (or 2-methyl-1-propanol) (CH3)2CH CH2OH; sec-butyl alcohol (or 2-butanol) CH3CHOHCH2 CH3; tert-butyl alcohol (or 2-methyl-2-propanol) (CH3)3 COH.
The boiling points of the butyl alcohols decrease regularly in moving down the above list, from 244°F (118°C) for n-butyl alcohol to 226°F (108°C) for isobutyl alcohol to 212°F (100°C) for sec-butyl alcohol to 180°F (82°C) for tert-butyl alcohol. A similar pattern exists for solubility of the alcohols, increasing from 8 g per 100 g of water for n-butyl alcohol to 10 g per 100 g of water and 12.5 g per 100 g of water for the next two forms to complete miscibility for tert-butyl alcohol.
The four butyl alcohols undergo very different reactions in many instances. As an example, n-butyl and isobutyl alcohol can be oxidized rather easily to yield aldehydes. Oxidation of sec-butyl alcohol, however, results in the formation of a ketone. Oxidation of tert-butyl alcohol occurs only under the most extreme conditions, resulting in the complete oxidation of the compound to carbon dioxide and water.
Of the four butyl alcohols, n-butyl alcohol is in the greatest demand commercially. It is used as a solvent for fats, waxes, gums, shellac, varnish, and other materials in many industrial processes. It is also used as the starting point in the preparation of other butyl compounds. All of the butyl alcohols are of some interest in the synthetic flavoring industry since they can react with organic acids to make pleasant smelling esters. For example, n-butyl butanoate has the odor of pineapple; 2-methylpropyl propanoate smells like rum; 2-methylpropyl methanoate, like apple; n-butyl methanoate, like banana; and n-butyl ehtanoate, like strawberry.
The accompanying table summarizes some butyl compounds and their most important uses.
Budavari, Susan, ed. The Merck Index. 11th ed. Rahway, NJ: Merck and Company, 1989. pp. 236-242.
Carey, Francis A. Organic Chemistry. New York: McGraw-Hill, 2002.
Hawley, Gessner G., ed. The Condensed Chemical Dictionary. 9th edition. New York: Van Nostrand Reinhold, 1977, pp. 133-142.
Loudon, G. Mark. Organic Chemistry. Oxford: Oxford University Press, 2002.