m -xylylenediamine

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Structural formula
Structural formula of m-xylylenediamine
General
Surname m -xylylenediamine
other names
  • m -XDA
  • 1,3-bis (aminomethyl) benzene
  • 1,3-bis (aminomethyl) benzene ( IUPAC )
Molecular formula C 8 H 12 N 2
Brief description

colorless to yellowish liquid

External identifiers / databases
CAS number 1477-55-0
EC number 216-032-5
ECHA InfoCard 100.014.575
PubChem 15133
Wikidata Q15726051
properties
Molar mass 136.20 g mol −1
Physical state

liquid

density

1.052 g cm −3

Melting point

14.1 ° C

boiling point

247 ° C

Vapor pressure

4 Pa (25 ° C)

solubility

miscible with water

Refractive index

1.5718

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

danger

H and P phrases H: 302-332-314-317-412
EUH: 071
P: 260-280-304 + 340-301 + 330 + 331-303 + 361 + 353-305 + 351 + 338-310-273
MAK

Switzerland: 0.1 mg m −3

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

m -Xylylenediamine is a chemical compound that is used in the manufacture of plastics.

Manufacturing

m -Xylylenediamine can be produced by reducing m -benzenedicarbonitrile with hydrogen in the presence of ammonia using a cobalt catalyst.

properties

The spectroscopic data of m -xylylenediamine are given in the literature.

use

Similar to the phenylenediamines , m -xylylenediamine is also used as a crosslinker for epoxides and for the production of polyurethanes. The thermoset made from bisphenol A diglycidyl ether cross-linked with m- xylylenediamine has such advantageous properties that it is used as a material in construction and automotive engineering.

Individual evidence

  1. a b c d e f g Entry on m-phenylenebis (methylamine) in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
  2. CDC: NIOSH Pocket Guide to Chemical Hazards - m-Xylene-alpha, alpha'-diamine , accessed April 14, 2015.
  3. R. Brömme: About some amido derivatives of m-xylene . In: Reports of the German Chemical Society . 21, No. 2, 1888, pp. 2700-2706. doi : 10.1002 / cber.18880210292 .
  4. Galperin et al. J. Appl. Chem. USSR (Engl. Transl.), 1971, 44, pp. 403, 396, 397.
  5. Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 1477-55-0 or M-xylylenediamine ), accessed on November 2, 2015.
  6. a b Patent US4482741A : Preparation of xylylenediamine. Published November 13, 1984 , Inventor: Paul R. Kurek.
  7. Xinzhi Chen, Zhou Shaodong, Chao Qian: hydrogen transfer reduction of nitriles in DBU based ionic liquids . In: Arkivoc . 2012, No. 8, 128-136, pp. 128-136. doi : 10.3998 / ark.5550190.0013.812 .
  8. Albert Jeyakumar, Han Goossens, Bart Noordover, Manoranjan Prusty, Matthias Scheibitz, Cor Koning: Polyamide-6,6-based blocky copolyamides obtained by solid-state modification . In: Journal of Polymer Science Part A: Polymer Chemistry . 51, No. 23, December 1, 2013, pp. 5118-5129. doi : 10.1002 / pola.26944 .
  9. ^ Ha Q. Pham, Maurice J. Marks: Epoxy Resins . In: Ullmann's Encyclopedia of Industrial Chemistry . September. doi : 10.1002 / 14356007.a09_547.pub2 .
  10. Patent US3379683 : Polyurethanes prepared from m-xylylenediamine.
  11. F. Fragaa, C. Castro-Dı́aza, E. Rodrı́guez-Núñeza, JM Martı́nez-Ageitos: Physical aging for an epoxy network diglycidyl ether of bisphenol A / m-xylylenediamine . In: polymer . 44, No. 19, September 2003, pp. 5779-5784. doi : 10.1016 / S0032-3861 (03) 00624-4 .