Naphthylene-1,5-diisocyanate

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Structural formula
Structural formula of naphthylene-1,5-diisocyanate
General
Surname Naphthylene-1,5-diisocyanate
other names
  • NDI
  • 1,5-naphthylene diisocyanate
Molecular formula C 12 H 6 N 2 O 2
Brief description

Hardly flammable flakes, white to yellowish solid with an aromatic odor

External identifiers / databases
CAS number 3173-72-6
EC number 221-641-4
ECHA InfoCard 100.019.675
PubChem 18503
Wikidata Q2786152
properties
Molar mass 210.19 g mol −1
Physical state

firmly

density

1.42 g cm −3

Melting point

127 ° C

boiling point
  • 315 ° C
  • 167 ° C (7 hPa)
Vapor pressure

<0.9 hPa (20 ° C)

solubility

practically insoluble in water

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
07 - Warning 08 - Dangerous to health

danger

H and P phrases H: 315-317-319-332-334-335-412
P: 261-273-280-284-304 + 340 + 312-342 + 311
Toxicological data

0.27 mg / l / 4 h ( LC 50 ,  rat ,  inh. )

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

Naphthylene-1,5-diisocyanate is a chemical compound from the group of organic diisocyanates .

Extraction and presentation

Naphthylene-1,5-diisocyanate is produced industrially in high yields by pyrolysis of methyl-1,5-naphthylene carbamate , which in turn is synthesized from 1,5-naphthylenedinitrile and amidation , chlorination and Hofmann rearrangement .

properties

Naphthylene-1,5-diisocyanate is a flammable, hardly ignitable, white to yellowish solid with an aromatic odor, which is practically insoluble in water and slowly decomposes in it. The compound begins to decompose from 200 ° C.

use

Naphthylene-1,5-diisocyanate is mainly used in the automotive industry for the production of polyurethane - elastomer and synthetic rubber used. In its pure and technical form, it is a solid substance whose effects are comparable to those of diphenylmethane-4,4'-diisocyanate .

safety instructions

Naphthylene-1,5-diisocyanate has a strong irritant effect on the skin and mucous membranes. The metabolite of 1,5-naphthylene diisocyanate, 1,5-diaminonaphthalene , is genotoxic and carcinogenic in animal experiments. Since no data were available on the extent of hydrolytic formation of 1,5-diaminonaphthalene after ingestion of 1,5-naphthylene diisocyanate, 1,5-naphthylene diisocyanate was classified in carcinogen category 3B.

Individual evidence

  1. ↑ a b c d e f g h i j k Entry on naphthylene-1,5-diisocyanate in the GESTIS substance database of the IFA , accessed on January 28, 2019(JavaScript required) .
  2. ↑ a b c Leng, G. (2012): 1,5-Naphthylenediisocyanat (NDI), BAT Value Documentation , 2009, Annual Thresholds and Classifications for the Workplace, doi: 10.1002 / 3527600418.bb317372d0015 .
  3. ↑ Entry on 1,5-naphthylene diisocyanate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on January 28, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .
  4. ↑ Google Patents: DE10034226A1 - Process for the production of 1,5-naphthylene diisocyanate - Google Patents , accessed on January 28, 2019