Diethylene glycol dinitrate

Structural formula
General
Surname	Diethylene glycol dinitrate
other names	Diethylene glycol dinitrate; Diglycol dinitrate; Didi; Bis (hydroxyethyl) ether dinitrate; DEGN; DEGDN; Oxydiethylenedinitrate;
Molecular formula	C 4 H 8 N 2 O 7
Brief description	colorless to yellowish liquid
External identifiers / databases
EC number	211-745-8
ECHA InfoCard	100.010.679
PubChem	61198
Wikidata	Q5275149
properties
Molar mass	196.12 g mol −1
Physical state	liquid
density	1.377 g cm −3 (25 ° C)
Melting point	−11.3 ° C (unstable form); 2 ° C (stable modification);
boiling point	160 ° C (if heated quickly)
Vapor pressure	0.48 Pa (20 ° C)
solubility	sparingly soluble in water (3.9 g l −1 at 25 ° C); soluble in organic solvents; hardly soluble in ethanol , carbon tetrachloride and carbon disulfide ;
safety instructions
H and P phrases	H: 200-300-310-330-373-412
	P: ?
Toxicological data	753 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 .

Diethylene glycol dinitrate is a chemical compound from the group of nitric acid esters . It was first described in 1927 by William H. Rinkenbach .

Extraction and presentation

Diethyleneglycoldinitrate can as nitroglycerin by nitration of diethylene glycol with mixed acid are prepared batchwise or continuously.

properties

Diethylene glycol dinitrate is an oily, colorless to yellowish, explosive liquid. It decomposes when heated above 190 ° C.

use

Diethylene glycol dinitrate is used for the production of low-smoke, erosion-reducing “cold” powders. During World War II, it was a component of German gun powders along with cellulose nitrate , centralite and potassium sulfate . The explosive power is only about 2/3 that of glycerol trinitrate , it is also less sensitive to impact. It can be gelatinized with collodion wool.

safety instructions

Diethylene glycol dinitrate reacts by impact or friction, heating or other ignition sources with rapid decomposition with the formation of large quantities of gas. The compound is a methaemoglobin generator and is as toxic as nitroglycerin. Its vapors or absorption through the skin cause headaches.

Diethylene glycol dinitrate was included in the EU's ongoing action plan ( CoRAP ) in 2016 in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation . The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. The reasons for the intake of diethylene glycol dinitrate were concerns about the high risk characterization ratio (RCR) and the dangers arising from a possible assignment to the group of PBT / vPvB substances, the possible dangers due to carcinogenic and reproductive properties and as a potential endocrine disruptor . The re-evaluation took place from 2016 and was carried out by Italy . A final report was then published.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on diethylene glycol dinitrate in the GESTIS substance database of the IFA , accessed on March 25, 2018(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on diethylene glycol dinitrate. In: Römpp Online . Georg Thieme Verlag, accessed on March 25, 2018.
↑ Entry on diethylene glycol dinitrate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on March 30, 2018. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Google Patents: US1686344A - Diethylene glycol dinitrate and process of preparing same - Google Patents , accessed March 25, 2018.
^ Josef Köhler, Rudolf Meyer, Axel Homburg: Explosivstoffe . John Wiley & Sons, 2012, ISBN 3-527-66007-0 ( limited preview in Google Book Search).
↑ Lexicon of Chemistry: Diethylene glycol dinitrate , accessed on March 25, 2018.
↑ European Chemicals Agency (ECHA): Substance Evaluation Conclusion and Evaluation Report .
↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): Oxydiethylene dinitrate , accessed on May 2, 2020.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on diethylene glycol dinitrate in the GESTIS substance database of the IFA , accessed on March 25, 2018(JavaScript required) .

[RömppOnline-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on diethylene glycol dinitrate. In: Römpp Online . Georg Thieme Verlag, accessed on March 25, 2018.

[CLP_100.010.679-3] Entry on diethylene glycol dinitrate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on March 30, 2018. Manufacturers or distributors can expand the harmonized classification and labeling .

[google.com-4] Google Patents: US1686344A - Diethylene glycol dinitrate and process of preparing same - Google Patents , accessed March 25, 2018.

[Josef_Köhler,_Rudolf_Meyer,_Axel_Homburg-5] Josef Köhler, Rudolf Meyer, Axel Homburg: Explosivstoffe . John Wiley & Sons, 2012, ISBN 3-527-66007-0 ( limited preview in Google Book Search).

[spektrum.de-6] Lexicon of Chemistry: Diethylene glycol dinitrate , accessed on March 25, 2018.

[7] European Chemicals Agency (ECHA): Substance Evaluation Conclusion and Evaluation Report .

[8] Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): Oxydiethylene dinitrate , accessed on May 2, 2020.