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Salpn ligand

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Salpn ligand
Names
IUPAC name 2,2'-{1,2-Propanediyl­bis}­diphenol
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.159 Edit this at Wikidata
EC Number
  • 202-374-2
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C17H18N2O2/c1-13(19-12-15-7-3-5-9-17(15)21)10-18-11-14-6-2-4-8-16(14)20/h2-9,11-13,20-21H,10H2,1H3/b18-11+,19-12+Key: RURPJGZXBHYNEM-GDAWTGGTSA-N
SMILES
  • OC1=CC=CC=C1/C=N/CC(C)/N=C/C2=CC=CC=C2O
Properties
Chemical formula C17H18N2O2
Molar mass 282.343 g·mol
Hazards
GHS labelling:
Pictograms GHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word Warning
Hazard statements H226, H302, H315, H317, H319, H360, H411, H412
Precautionary statements P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P270, P272, P273, P280, P281, P301+P312, P302+P352, P303+P361+P353, P305+P351+P338, P308+P313, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P391, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N (what is  ?) Infobox references
Chemical compound

Salpn is the common name for a chelating ligand, properly called N,N′-bis(salicylidene)-1,2-propanediamine, used as a motor oil additive.

The molecular structure of pure (metal-free) salpn, sometimes denoted H2(salpn) or salpnH2, can be described as the salen ligand with a methyl group attached to the ethylene bridge that links the two nitrogen atoms.

As in the case of salen compound, the actual ligand is usually the conjugate base salpn, the divalent anion that result from the metal-free compound by the loss of two hydroxyl protons. This dianion is commonly denoted "(salpn)" in formulas of metal complexes.

The abbreviation "salpn" is also sometimes used for the structural isomer N,N′-bis(salicylidene)-1,3-diamino­propane and its conjugate base, derived from 1,3-diaminopropane rather than 1,2-diaminopropane.

Preparation

The synthesis of salpn is achieved by a condensation reaction of 1,2-diaminopropane with salicylaldehyde:

2C6H4(OH)CHO + CH3CH(NH2)CH2NH2 → 2CH3CHNCH2N + 2H2O

Uses

Salpn is used as a fuel additive as a metal deactivator in motor oils. Trace metals degrade the fuels by catalyzing oxidation processes that lead to gums and solids. Metal deactivators like salpn form stable coordination compounds with the metals, suppressing their catalytic activity. While salpn forms stable chelate complexes with many metals including copper, iron, chromium, and nickel, it is the coordination with copper that makes it a popular choice as a fuel additive. Copper has the highest catalytic activity in fuel, and salpn forms a highly stable square planar complex with the metal.

Salpn is preferred over salen, possibly because it has higher solubility in non-polar liquids.

References

  1. ^ Dabelstein, W.; Reglitzky A.; Schutze A.; Reders, K. "Automotive Fuels". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 978-3527306732.
  2. K. Rajender Reddy, M. V. Rajasekharan, and J.-P. Tuchagues (1998): "Synthesis, Structure, and Magnetic Properties of Mn(salpn)N3, a Helical Polymer, and Fe(salpn)N3, a Ferromagnetically Coupled Dimer(salpnH2 = N,N′-bis(Salicylidene)-1,3-diaminopropane)". Inorganic Chemistry, volume 37, issue 23, pages 5978–5982. doi:10.1021/ic971592y
  3. Evans, D. A.; Miller, S. J.; Lectka, T.; von Matt. P. (1999). "Chiral Bis(oxazoline)copper(II) Complexes as Lewis Acid Catalysts for Enantioselective Diels–Alder Reaction". J. Am. Chem. Soc. 121: 7559–7573. doi:10.1021/ja991190k.
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