1,2-Diaminopropane (propane-1,2-diamine) is

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula CHCH(NH)CHNH. A colorless liquid, it is the simplest chiral

diamine A diamine is an amine with two amino groups. Diamines are used as monomers to prepare polyamides, polyimides, and polyureas. The term ''diamine'' refers mostly to Primary (chemistry), primary diamines, as those are the most reactive. In terms of ...

Preparation

Industrially, this compound is synthesized by the

ammonolysis In chemistry, ammonolysis (/am·mo·nol·y·sis/) is the process of splitting ammonia into NH2- + H+. Ammonolysis reactions can be conducted with organic compounds to produce amines (molecules containing a nitrogen atom with a lone pair, :N), o ...

of 1,2-dichloropropane: :CHCHClCHCl + 4 NH → CHCH(NH)CHNH + 2 NHCl This preparation allows for the use of waste chloro-organic compounds to form useful amines using inexpensive and readily available

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

. The racemic mixture of this chiral compound may be separated into enantiomers by conversion into the diastereomeric tartaric acid ammonium salt. After purification of the diastereomer, the diamine can be regenerated by treatment of the ammonium salt with sodium hydroxide. Alternate reagents for

chiral resolution Chiral resolution, or enantiomeric resolution, is a process in stereochemistry for the separation of racemic mixture into their enantiomers. It is an important tool in the production of optically active compounds, including drugs. Another term wit ...

include N-p-toluenesulfonylaspartic acid, N-benzenesulfonylaspartic acid, or N-benzoylglutamic acid.

Uses

1,2-Diaminopropane is used in the synthesis of ''N'',''N''-disalicylidene-1,2-propanediamine, a salen-type

ligand In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's el ...

, usually abbreviated as salpn, that is used as a metal deactivating additive in

motor oil Motor oil, engine oil, or engine lubricant is any one of various substances used for the lubrication of internal combustion engines. They typically consist of base oils enhanced with various additives, particularly antiwear additives, deterge ...

Related compounds and derivatives

1,2-Diaminopropane forms

coordination complex A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of chemical bond, bound molecules or ions, that are in turn known as ' ...

es similar to tris(ethylenediamine)cobalt(III). Owing to the presence of the methyl groups, o(pn)₃sup>3+ can exist as 24 stereoisomers. Two chiral 1,2-diamines are 1,2-diaminocyclohexane and 2,3-diaminobutane. The chiral diastereomers of those diamines are C₂-symmetric.

References

{{DEFAULTSORT:Diaminopropane, 1, 2- Diamines Chelating agents Fuel antioxidants Corrosion inhibitors