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Sebacoyl chloride

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Sebacoyl chloride
Skeletal formula of sebacoyl chloride
Skeletal formula of sebacoyl chloride
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name Decanedioyl dichloride
Other names Sebacoyl dichloride
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.495 Edit this at Wikidata
EC Number
  • 203-843-4
MeSH C061659
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H16Cl2O2/c11-9(13)7-5-3-1-2-4-6-8-10(12)14/h1-8H2Key: WMPOZLHMGVKUEJ-UHFFFAOYSA-N
  • InChI=1/C10H16Cl2O2/c11-9(13)7-5-3-1-2-4-6-8-10(12)14/h1-8H2Key: WMPOZLHMGVKUEJ-UHFFFAOYAH
SMILES
  • ClC(=O)CCCCCCCC(=O)CCl
Properties
Chemical formula C10H16Cl2O2
Molar mass 239.14 g/mol
Density 1.12 g cm
Melting point −2.5 °C (27.5 °F; 270.6 K)
Boiling point 220 °C (428 °F; 493 K)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 0: Will not burn. E.g. waterInstability 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
3 0 2W
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Preparation

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

Use

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

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. Bibcode:1959JChEd..36..182M. 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. PMID 10941915.
  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.
Diacyl chlorides (-COCl)2
Chemical structure of the -COCl group
Category:Acyl chlorides
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