Diallylamine is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula HN(CH₂CH=CH₂)₂. It is a colorless liquid with an ammonia-like odor. It is multifunctional, featuring a

secondary amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such a ...

and two alkene groups. Diallylamine is used in the production of ''N,N''-diallyldichloroacetamide and ''N,N''-diallyldimethylammonium chloride.

Preparation

It is produced commercially by partial hydrogenation of

acrylonitrile Acrylonitrile is an organic compound with the formula and the structure . It is a colorless, volatile liquid although commercial samples can be yellow due to impurities. It has a pungent odor of garlic or onions. In terms of its molecular ...

: : 2NCCH=CH₂ + 4H₂ → HN(CH₂CH=CH₂)₂ + NH₃ A laboratory route to diallylamine entails diallylation of

calcium cyanamide Calcium cyanamide is the inorganic compound with the formula CaCN2. It is the calcium salt of the cyanamide () anion. This chemical is used as fertilizer and is commercially known as nitrolime. It was first synthesized in 1898 by Adolph Frank and ...

followed by decyanation of the product.{{cite journal , doi=10.15227/orgsyn.005.0043, title=Diallylamine, journal=Organic Syntheses, year=1925, volume=5, page=43, author=E. B. Vliet

Related compounds

Allylamine Allylamine is an organic compound with the formula C3H5NH2. This colorless liquid is the simplest stable unsaturated amine. Production and reactions All three allylamines, mono-, di-, and triallylamine, are produced by the treating allyl chlori ...

Triallylamine Triallylamine is the organic compound with the formula N(CH2CH=CH2)3. It is a colorless liquid with an ammonia-like odor. It is multifunctional, featuring a tertiary amine and three alkene groups. Triallylamine (and mono- and diallyl amines) is p ...

References

Amines Allylamines