Adipoyl chloride


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Adipoyl chloride (or adipoyl dichloride) is the organic compound with the formula (CH2CH2C(O)Cl)2. It is a colorless liquid. It reacts with water to give adipic acid.

Adipoyl chloride
Skeletal formula
Skeletal formula
Names
Preferred IUPAC name

Hexanedioyl dichloride

Other names

Adipoyl dichloride

Identifiers

3D model (JSmol)
507709
ChemSpider
ECHA InfoCard 100.003.525 Edit this at Wikidata
EC Number
  • 203-876-4
UN number 3265

  • InChI=1S/C6H8Cl2O2/c7-5(9)3-1-2-4-6(8)10/h1-4H2 check

    Key: PWAXUOGZOSVGBO-UHFFFAOYSA-N check

  • InChI=1/C6H8Cl2O2/c7-5(9)3-1-2-4-6(8)10/h1-4H2

    Key: PWAXUOGZOSVGBO-UHFFFAOYAI

  • O=C(Cl)CCCCC(Cl)=O

Properties
C6H8Cl2O2
Molar mass 183.03 g·mol−1
Density 1.25 g/cm3
Boiling point 105 to 107 °C (221 to 225 °F; 378 to 380 K) at 2 mmHg
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 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 hazards (white): no code

3

1

2

Flash point 160 °C (320 °F; 433 K) (closed cup)
Related compounds

Related compounds

 Adipic acid
Hexanedihydrazide
Hexanedinitrile
Hexanediamide

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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It is prepared by treatment of adipic acid with thionyl chloride.[1] Adipoyl chloride reacts with hexamethylenediamine to form nylon 6,6.[2]

See also

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References

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  1. ^ P. C. Guha; D. K. Sankaran (1946). "Muconic Acid". Organic Syntheses. 26: 57–60. doi:10.15227/orgsyn.026.0057. PMID 20280761.
  2. ^ Morgan, Paul W.; Kwolek, Stephanie L. (April 1959). "The nylon rope trick: Demonstration of condensation polymerization". J. Chem. Educ. 36 (4): 182. Bibcode:1959JChEd..36..182M. doi:10.1021/ed036p182.

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