Azodicarbonamide

Azodicarbonamide

Names
IUPAC name Carbamoyliminourea
Other names Azodicarboxamide; Azobisformamide; C,C'-Azodi(formamide); Diazenedicarboxamide
Identifiers
CAS Number	123-77-3 Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL28517 Y
ChemSpider	4575589 Y
ECHA InfoCard	100.004.229
EC Number	204-650-8
E number	E927a (glazing agents, ...)
PubChem	31269
UNII	56Z28B9C8O Y
InChI InChI=1S/C2H4N4O2/c3-1(7)5-6-2(4)8/h(H2,3,7)(H2,4,8)/b6-5+ Y Key: XOZUGNYVDXMRKW-AATRIKPKSA-N Y InChI=1/C2H4N4O2/c3-1(7)5-6-2(4)8/h(H2,3,7)(H2,4,8)/b6-5+ Key: XOZUGNYVDXMRKW-AATRIKPKBW
SMILES O=C(/N=N/C(=O)N)N
Properties
Chemical formula	C2H4N4O2
Molar mass	116.08 g·mol−1
Appearance	Yellow to orange/red crystalline powder
Melting point	225 °C (437 °F; 498 K) (decomposes)
Hazards
Safety data sheet	[1]
EU classification (DSD)	Harmful (Xn)
R-phrases	R42 R44
S-phrases	S22 S24 S37
NFPA 704	1 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Azodicarbonamide, or azo(bis)formamide, is a chemical compound with the molecular formula C₂H₄O₂N₄. It is a yellow to orange-red, odorless, crystalline powder.

The principal use of azodicarbonamide is in the production of foamed plastics as a blowing agent. The thermal decomposition of azodicarbonamide results in the evolution of nitrogen, carbon monoxide, carbon dioxide, and ammonia gases, which are trapped in the polymer as bubbles to form a foamed article.

Azodicarbonamide is used in plastics, synthetic leather, and other industries and can be pure or modified. Modification affects the reaction temperatures. Pure azodicarbonamide generally reacts around 200 °C. In the plastic, leather, and other industries, modified azodicarbonamide (average decomposition temperature 170 °C) contains additives that accelerate the reaction or react at lower temperatures.

An example of the use of azodicarbonamide as a blowing agent is found in the manufacture of vinyl (PVC) foam, where it plays a role in the formation of air bubbles by breaking down into gas at high temperature. Vinyl foam is springy and does not slip on smooth surfaces. It is useful for carpet underlay and floor mats. Commercial yoga mats made of vinyl foam have been available since the 1980s; the first mats were cut from carpet underlay.

As a food additive, azodicarbonamide is used as a flour bleaching agent and a dough conditioner. It reacts with moist flour as an oxidizing agent. The main reaction product is biurea, a derivative of urea, which is stable during baking. Secondary reaction products include semicarbazide and ethyl carbamate. It is known by the E number E927. Many restaurants in the US fast food industry removed the additive in response to negative publicity.

In the United States, azodicarbonamide has generally recognized as safe (GRAS) status and is allowed to be added to flour at levels up to 45 ppm. Azodicarbonamide has not been authorized for use in Australia and the European Union as a food additive.