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
CAS Number	111-19-3 Y
3D model (JSmol)	Interactive image
ChemSpider	59462 N
ECHA InfoCard	100.003.495
EC Number	203-843-4
MeSH	C061659
PubChem CID	66072
UNII	8JT2RJH7AU Y
CompTox Dashboard (EPA)	DTXSID3059397
InChI 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
SMILES ClC(=O)CCCCCCCC(=O)CCl
Properties
Chemical formula	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
NFPA 704 (fire diamond)	3 0 2 W
Safety data sheet (SDS)	External MSDS
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

• Sebacic acid
• Adipoyl chloride