:Adipoyl chloride
{{Chembox
| verifiedrevid = 477242895
| Watchedfields = changed
| ImageFileL1 = Adipoyl_chloride.png
| ImageNameL1 = Skeletal formula
| ImageFileR1 = Adipoyl-chloride-3D-balls.png
| ImageName1 = Ball-and-stick model
| PIN = Hexanedioyl dichloride
| OtherNames = Adipoyl dichloride
|Section1={{Chembox Identifiers
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H8Cl2O2/c7-5(9)3-1-2-4-6(8)10/h1-4H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PWAXUOGZOSVGBO-UHFFFAOYSA-N
| CASNo = 111-50-2
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 61034
| ChemSpiderID = 54993
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 203-876-4
| UNNumber = 3265
| SMILES = O=C(Cl)CCCCC(Cl)=O
| InChI = 1/C6H8Cl2O2/c7-5(9)3-1-2-4-6(8)10/h1-4H2
| InChIKey = PWAXUOGZOSVGBO-UHFFFAOYAI
| Beilstein = 507709}}
|Section2={{Chembox Properties
| C=6 | H=8 | Cl=2 | O=2
| Density = 1.25 g/cm3
| MeltingPt =
| BoilingPtC = 105 to 107
| BoilingPt_notes = at 2 mmHg
}}
|Section7={{Chembox Hazards
| NFPA-H = 3
| NFPA-F = 1
| NFPA-R = 2
| NFPA-S =
| FlashPtC = 160
| FlashPt_notes = (closed cup)}}
| Section8 = {{Chembox Related
| OtherCompounds = Adipic acid
Hexanedihydrazide
Hexanedinitrile
Hexanediamide
}}
}}
Adipoyl chloride (or adipoyl dichloride) is the organic compound with the formula (CH2CH2C(O)Cl)2. It is a clear brown liquid. It reacts with water to give adipic acid.
It is prepared by treatment of adipic acid with thionyl chloride.{{cite journal|journal=Organic Syntheses|title=Muconic Acid|volume=26|year=1946|author1=P. C. Guha |author2=D. K. Sankaran|pages=57–60|doi=10.15227/orgsyn.026.0057|pmid=20280761}}
Adipoyl chloride reacts with hexamethylenediamine to form nylon 6,6.{{Cite journal |title=The nylon rope trick: Demonstration of condensation polymerization |first1=Paul W. |last1=Morgan |first2=Stephanie L. |last2=Kwolek |authorlink2=Stephanie Kwolek |journal= J. Chem. Educ. |volume=36 |issue=4 |page=182 |doi=10.1021/ed036p182 |date=April 1959|bibcode=1959JChEd..36..182M }}
See also
References
{{reflist}}
External links
- [http://msds.chem.ox.ac.uk/AD/adipoyl_chloride.html MSDS Safety data] {{Webarchive|url=https://web.archive.org/web/20100109131018/http://msds.chem.ox.ac.uk/AD/adipoyl_chloride.html |date=2010-01-09 }}
{{Navbox acyl chlorides}}