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
Names
Preferred IUPAC name
Decanedioyl dichloride
Other names
Sebacoyl dichloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.495
EC Number
  • 203-843-4
MeSH C061659
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)
Flammability code 0: Will not burn. E.g. waterHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
0
3
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 YN ?)
Infobox references

Preparation

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

Use

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

See also

References
  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.
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