Sebacoyl chloride

Sebacoyl chloride (or sebacoyl dichloride) is a di-acyl chloride, with formula (CH2)8(COCl)2. A colorless oily liquid with a pungent odor, it is soluble in hydrocarbons and ethers. Sebacoyl chloride is corrosive; like all acyl chlorides, it hydrolyzes, evolving hydrogen chloride. It is less susceptible to hydrolysis though than shorter chain aliphatic acyl chlorides.[1]

Sebacoyl chloride
Skeletal formula of sebacoyl chloride
Ball-and-stick model
Names
Preferred IUPAC name
Decanedioyl dichloride
Other names
Sebacoyl dichloride
Identifiers
  • 111-19-3 checkY
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.495 Edit this at Wikidata
EC Number
  • 203-843-4
MeSH C061659
  • InChI=1S/C10H16Cl2O2/c11-9(13)7-5-3-1-2-4-6-8-10(12)14/h1-8H2 ☒N
    Key: WMPOZLHMGVKUEJ-UHFFFAOYSA-N ☒N
  • InChI=1/C10H16Cl2O2/c11-9(13)7-5-3-1-2-4-6-8-10(12)14/h1-8H2
    Key: WMPOZLHMGVKUEJ-UHFFFAOYAH
  • ClC(=O)CCCCCCCC(=O)CCl
Properties
C10H16Cl2O2
Molar mass 239.14 g/mol
Density 1.12 g cm−3
Melting point −2.5 °C (27.5 °F; 270.6 K)
Boiling point 220 °C (428 °F; 493 K)
Hazards
Safety data sheet External MSDS
NFPA 704 (fire diamond)
3
0
2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

PreparationEdit

Sebacoyl chloride can be prepared by reacting sebacic acid with an excess of thionyl chloride. Residual thionyl chloride can be removed by distillation.[2]

UseEdit

Sebacoyl chloride can be polymerized with hexamethylenediamine yielding nylon-6,10.[3]

See alsoEdit

ReferencesEdit

  1. ^ Morgan, Paul W.; Kwolek, Stephanie L. (April 1959). "The nylon rope trick: Demonstration of condensation polymerization". Journal of Chemical Education. 36 (4): 182. doi:10.1021/ed036p182.
  2. ^ Erdmann, L.; Uhrich, K.E. (October 2000). "Synthesis and degradation characteristics of salicylic acid-derived poly(anhydride-esters)". Biomaterials. 21 (19): 1941–1946. doi:10.1016/S0142-9612(00)00073-9.
  3. ^ Enkelmann, Volker; Wegner, Gerhard (1976-11-01). "Mechanism of interfacial polycondensation and the direct synthesis of stable polyamide membranes". Die Makromolekulare Chemie. 177 (11): 3177–3189. doi:10.1002/macp.1976.021771106. ISSN 0025-116X.