Sebacoyl chloride
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Names | |
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Preferred IUPAC name Decanedioyl dichloride | |
Other names Sebacoyl dichloride | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.003.495 |
EC Number |
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MeSH | C061659 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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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 | |
NFPA 704 (fire diamond) | |
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). |
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]
Preparation
[edit]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
[edit]Sebacoyl chloride can be polymerized with hexamethylenediamine yielding nylon-6,10.[3]
See also
[edit]References
[edit]- ^ Morgan, Paul W.; Kwolek, Stephanie L. (April 1959). "The nylon rope trick: Demonstration of condensation polymerization". Journal of Chemical Education. 36 (4): 182. Bibcode:1959JChEd..36..182M. doi:10.1021/ed036p182.
- ^ 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. PMID 10941915.
- ^ 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.