Pelargonic acid

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Pelargonic acid
Names
Preferred IUPAC name
Nonanoic acid
Other names
Nonoic acid; nonylic acid; 1-octanecarboxylic acid; C9:0 (lipid numbers)
Identifiers
3D model (
JSmol
)
1752351
ChEBI
ChemSpider
ECHA InfoCard
 100.003.574 Edit this at Wikidata
EC Number
  • 203-931-2
185341
KEGG
UNII
  • InChI=1S/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11) checkY
    Key: FBUKVWPVBMHYJY-UHFFFAOYSA-N checkY
  • InChI=1/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11)
    Key: FBUKVWPVBMHYJY-UHFFFAOYAF
  • CCCCCCCCC(=O)O
Properties
C9H18O2
Molar mass 158.241 g/mol
Appearance Clear to yellowish oily liquid
Density 0.900 g/cm3
Melting point 12.5 °C (54.5 °F; 285.6 K)
Boiling point 254 °C (489 °F; 527 K)
Critical point (T, P) 439 °C (712 K), 2.35 MPa
0.3 g/L
Acidity (pKa)
  • 4.96[1]
  • 1.055 at 2.06–2.63 K (−271.09 – −270.52 °C; −455.96 – −454.94 °F)
  • 1.53 at −191 °C (−311.8 °F; 82.1 K)
1.4322
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Corrosive
GHS labelling:
GHS05: Corrosive GHS07: Exclamation mark
Warning
H315, H319, H412
P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Flash point 114 °C (237 °F; 387 K)
405 °C (761 °F; 678 K)
Related compounds
Related compounds
decanoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pelargonic acid, also called nonanoic acid, is an

salts
of pelargonic acid are called pelargonates or nonanoates.

The acid is named after the

esters
of the acid.

Preparation

Together with azelaic acid, it is produced industrially by ozonolysis of oleic acid.[2]

Alternatively, pelargonic acid can be produced in a two-step process beginning with coupled

hydrogenated to give esters of pelargonic acid.[3]

A laboratory preparation involves permanganate oxidation of

1-decene.[4]

Occurrence and uses

Pelargonic acid occurs naturally as esters in the oil of pelargonium.

Synthetic esters of pelargonic acid, such as methyl pelargonate, are used as flavorings. Pelargonic acid is also used in the preparation of

4-nonanoylmorpholine is an ingredient in some pepper sprays
.

The

turfgrass. It works by causing leaks in plant cell membranes, allowing chlorophyll molecules to escape the chloroplast. Under sunlight, these misplaced molecules cause immense oxidative damage to the plant.[5]

The methyl form and ethylene glycol pelargonate act as

Glycine max.[6]

Esters of pelargonic acid are precursors to lubricants.

Pharmacological effects

Pelargonic acid may be more potent than

teratogenicity.[7]

See also

References

  1. ^ Lide, D. R. (Ed.) (1990). CRC Handbook of Chemistry and Physics (70th Edn.). Boca Raton (FL):CRC Press.
  2. doi:10.1002/14356007.a10_245.pub2
  3. ISBN 978-3527306732
    .
  4. doi:10.15227/orgsyn.060.0011
    .
  5. doi:10.1016/j.pestbp.2004.06.010
    .
  6. PMID 12147760
    . p. 229.
  7. ^
    PMID 23177536
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Pelargonic_acid&oldid=1218901588"