1,2-Diaminopropane

1,2-Diaminopropane (propane-1,2-diamine) is organic compound with the formula CH3CH(NH2)CH2NH2. A colorless liquid, it is the simplest chiral diamine. It is used as a bidentate ligand in coordination chemistry.

1,2-Diaminopropane
Names
Preferred IUPAC name
1,2-Propanediamine
Systematic IUPAC name
Propane-1,2-diamine
Identifiers
3D model (JSmol)
605274
ChEBI
ChemSpider
ECHA InfoCard 100.001.051
EC Number
  • 201-155-9
25709
MeSH 1,2-diaminopropane
RTECS number
  • TX6650000
UNII
UN number 2258
Properties
C3H10N2
Molar mass 74.127 g·mol−1
Appearance Colourless liquid
Odor Fishy, ammoniacal
Density 870 mg mL−1
Melting point −37.1 °C; −34.9 °F; 236.0 K
Boiling point 119.6 °C; 247.2 °F; 392.7 K
Vapor pressure 1.9 Pa (at 20 °C)
-58.1·10−6 cm3/mol
1.446
Thermochemistry
205.64 J K−1 mol−1
247.27 J K−1 mol−1
Std enthalpy of
formation (ΔfH⦵298)
 −98.2–−97.4 kJ mol−1
Std enthalpy of
combustion (ΔcH⦵298)
 −2.5122–−2.5116 MJ mol−1
Hazards
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H226, H302, H312, H314
P280, P305+351+338, P310
Flash point 34 °C (93 °F; 307 K)
360 °C (680 °F; 633 K)
Explosive limits 1.9–11.1%
Lethal dose or concentration (LD, LC):
  • 434 mg kg−1 (dermal, rabbit)
  • 2.23 g kg−1 (oral, rat)
Related compounds
Related alkanamines
Related compounds
 2-Methyl-2-nitrosopropane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Preparation

Industrially, this compound is synthesized by the ammonolysis of 1,2-dichloropropane:[1]

CH3CHClCH2Cl + 4 NH3 → CH3CH(NH2)CH2NH2 + 2 NH4Cl

This preparation allows for the use of waste chloro-organic compounds to form useful amines using inexpensive and readily available ammonia.[1]

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.[2] Alternate reagents for chiral resolution include N-p-toluenesulfonylaspartic acid, N-benzenesulfonylaspartic acid, or N-benzoylglutamic acid.[3]

Uses

Metal deactivator

1,2-Diaminopropane is used in the synthesis of N,N′-disalicylidene-1,2-propanediamine, a salen-type ligand, usually abbreviated as salpn, that is used as a metal deactivating additive in motor oils.[4]

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References
  1. Bartkowiak, M.; Lewandowski, G.; Milchert, E.; Pelech, R. (2006). "Optimization of 1,2-Diaminopropane Preparation by the Ammonolysis of Waste 1,2-Dichloropropane". Ind. Eng. Chem. Res. 45 (16): 5681–5687. doi:10.1021/ie051134u.
  2. Romanowski, G.; Wera, M. (2010). "Mononuclear and dinuclear chiral vanadium(V) complexes with tridentate Schiff bases derived from R(−)-1,2-diaminopropane: Synthesis, structure, characterization and catalytic properties". Polyhedron. 29 (13): 2747–2754. doi:10.1016/j.poly.2010.06.030.
  3. JP application 04-018057, Sakie, N. & Haruyo, S., "Production of Optically Active 1,2-propanediamine"
  4. Dabelstein, W.; Reglitzky A.; Schutze A.; Reders, K. "Automotive Fuels". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_719.pub2.
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