''tert''-Butylamine (also erbumine and other names) is an organic chemical compound with the formula (CH
3)
3CNH
2. It is a colorless liquid with a typical amine-like odor. ''tert''-Butylamine is one of the four isomeric
amine
In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...
s of
butane
Butane () is an alkane with the formula C4H10. Butane exists as two isomers, ''n''-butane with connectivity and iso-butane with the formula . Both isomers are highly flammable, colorless, easily liquefied gases that quickly vaporize at ro ...
, the others being
''n''-butylamine,
''sec''-butylamine and
isobutylamine
Isobutylamine is an organic chemical compound (specifically, an amine) with the formula (CH3)2CHCH2NH2, and occurs as a colorless liquid.zeolite
Zeolites are a group of several microporous, crystalline aluminosilicate minerals commonly used as commercial adsorbents and catalysts. They mainly consist of silicon, aluminium, oxygen, and have the general formula ･y where is either a meta ...
catalyst
Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...
s:
:NH
3 + CH
2=C(CH
3)
2 → H
2NC(CH
3)
3
The
Ritter reaction
The Ritter reaction (sometimes called the Ritter amidation) is a chemical reaction that transforms a nitrile into an ''N''-alkyl amide using various electrophilic alkylating reagents. The original reaction formed the alkylation, alkylating agent u ...
of
isobutene
Isobutylene (or 2-methylpropene) is a hydrocarbon with the chemical formula . It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. It is a colorless flammable gas, and is of considerable industrial value.
Productio ...
with
hydrogen cyanide
Hydrogen cyanide (formerly known as prussic acid) is a chemical compound with the chemical formula, formula HCN and structural formula . It is a highly toxic and flammable liquid that boiling, boils slightly above room temperature, at . HCN is ...
is not useful because it produces too much waste.
:(CH
3)
2C=CH
2 + HCN + H
2O → (CH
3)
3CNHCHO
:(CH
3)
3CNHCHO + H
2O → (CH
3)
3CNH
2 + HCO
2H
In the laboratory, it can be prepared by the
hydrogenolysis of 2,2-dimethylethylenimine, or via ''tert''-butylphthalimide.
Uses
''tert''-Butylamine is used as an intermediate in the preparation of the
sulfenamides such as ''N''-''tert''-butyl-2-benzothiazylsulfenamide and ''N''-''tert''-butyl-2-benzothiazylsulfenimide. As rubber accelerators, these compounds modify the rate of
vulcanization
Vulcanization (British English: vulcanisation) is a range of processes for hardening rubbers. The term originally referred exclusively to the treatment of natural rubber with sulfur, which remains the most common practice. It has also grown to ...
of
rubber
Rubber, also called India rubber, latex, Amazonian rubber, ''caucho'', or ''caoutchouc'', as initially produced, consists of polymers of the organic compound isoprene, with minor impurities of other organic compounds.
Types of polyisoprene ...
. A variety of
pesticide
Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others (see table). The most common of these are herbicides, which account for approximately 50% of all p ...
s are derived from this amine, including
terbacil,
terbutryn, and
terbumeton.
In pharmacology under the name erbumine, ''tert''-butylamine has been used as a
counterion in drug substances such as
perindopril erbumine.
See also
*
Borane ''tert''-butylamine complex
References
{{DEFAULTSORT:Butylamine, tert-
Alkylamines
Tert-butyl compounds