Decanedioyl dichloride

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Structural formula
Structure of decanedioyl dichloride
General
Surname Decanedioyl dichloride
other names
  • Sebacoyl dichloride
  • Decanedioic acid chloride
Molecular formula C 10 H 16 Cl 2 O 2
Brief description

colorless liquid with a pungent odor

External identifiers / databases
CAS number 111-19-3
EC number 203-843-4
ECHA InfoCard 100.003.495
PubChem 66072
Wikidata Q3289067
properties
Molar mass 239.14 g mol −1
Physical state

liquid

density

1.12 g cm −3

Melting point

−5 ° C

boiling point

161 ° C (at 19 hPa )

solubility

Decomposes in water

safety instructions
GHS labeling of hazardous substances
05 - Corrosive 07 - Warning

danger

H and P phrases H: 302-314-335
P: 280-301 + 330 + 331-305 + 351 + 338-308 + 310
Toxicological data

400 mg / kg mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Decanedioyl dichloride is the bis- carboxylic acid chloride of decanedioic acid ( sebacic acid ).

properties

Decanedioyl dichloride is a colorless liquid with a pungent odor and soluble in hydrocarbons and diethyl ether . Decanedioyl dichloride is corrosive; like all carboxylic acid chlorides , it hydrolyzes in water with the release of hydrogen chloride . However, it is less sensitive to hydrolysis than shorter-chain aliphatic carboxylic acid chlorides.

Decanedioyl dichloride has a flash point of 113 ° C.

Manufacturing

Decanedioyl dichloride can be prepared by reacting decanedioic acid in an excess of thionyl chloride . Remaining thionyl chloride can be removed by distillation after the reaction .

use

Decandioyldichlorid can with hexamethylene diamine to nylon 6,10 polycondensed be.

Individual evidence

  1. ↑ a b c d e f g h i Entry on sebacoyl dichloride in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
  2. ↑ Paul W. Morgan, Stephanie L. Kwolek: The nylon rope trick: Demonstration of condensation polymerization . In: Journal of Chemical Education . tape 36 , no. 4 , April 1959, p. 182 , doi : 10.1021 / ed036p182 .
  3. ↑ L. Erdmann, KE Uhrich: Synthesis and degradation characteristics of salicylic acid-derived poly (anhydride-esters) . In: Biomaterials . tape 21 , no. October 19 , 2000, p. 1941-1946 , doi : 10.1016 / S0142-9612 (00) 00073-9 .
  4. ↑ Volker Enkelmann, Gerhard Wegner: Mechanism of interfacial polycondensation and the direct synthesis of stable polyamide membranes . In: The Macromolecular Chemistry . tape 177 , no. November 11 , 1976, p. 3177-3189 , doi : 10.1002 / macp.1976.021771106 .