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Azodicarbonamide

Names
IUPAC name Carbamoyliminourea
Other names Azodicarobxamide Azobisformamide C,C'-azodi(formamide)
Identifiers
CAS Number	123-77-3
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL28517
ChemSpider	4575589
ECHA InfoCard	100.004.229
E number	E927a (glazing agents, ...)
PubChem CID	31269
UNII	56Z28B9C8O
CompTox Dashboard (EPA)	DTXSID0024553
InChI InChI=1S/C2H4N4O2/c3-1(7)5-6-2(4)8/h(H2,3,7)(H2,4,8)/b6-5+Key: XOZUGNYVDXMRKW-AATRIKPKSA-N 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	116.080 g·mol
Appearance	Yellow to orange/red crystalline powder
Hazards
NFPA 704 (fire diamond)	2 1 2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) Infobox references

Azodicarbonamide, or azobisformamide, is an synthetic chemical with the molecular formula C₂H₄O₂N₄. It is a yellow to orange red, odorless, crystalline powder. As a food additive, it is known by the E number E927.

Use as a food additive

Azodicarbonamide is used in food industry as a food additive, a flour bleaching agent and improving agent. It reacts with moist flour as an oxidizing agent. The main reaction product is biurea (not urea), which is stable during baking. Secondary reaction products include semicarbazide and ethyl carbamate.

The United States allows azodicarbonamide to be added to flour at levels up to 45 ppm. Use of azodicarbonamide as a food additive is banned in Australia and in Europe. In Singapore, the use of azodicarbonamide can result in up to 15 years imprisonment and a fine of $450,000.

Other uses

The principal use of azodicarbonamide is in the production of foamed plastics as an additive. 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. Common examples of this application are window and door gaskets, padded floor mats, gym/exercise mats, shoe soles, etc.

It is important to mention that azodicarbonamide in the use of plastics, synthetic leather and other uses can be pure or modified. This is important because modification affects the reaction temperatures. Pure azodicarbonamide generally reacts around 200 degrees C, but there are some products that the reaction temperature must be lower, depending on the application. In the plastic, leather and other industries, modified azodiarbonamide (average decomposition temperature 170 degrees C) contain additives that accelerate the reaction or react at lower temperatures.

Safety

In the UK, the Health and Safety Executive has identified azodicarbonamide as a respiratory sensitizer (a possible cause of asthma) and determined that products should be labeled with "May cause sensitisation by inhalation."

Azodicarbonamide may cause an allergic reaction in those sensitive to other azo compounds, such as food dyes. The consumption of azodicarbonamide may also heighten an allergic reaction to other ingredients in a food.

In connection with food safety, it has wrongly been claimed that azodicarbonamide is completely decomposed into common substances during baking, either into urea or (alternatively) into gases (carbon dioxide, carbon monoxide, nitrogen, and ammonia). Toxicological studies of the reactions of azodicarbonamide show that it is rapidly converted to biurea in dough, which is a stable compound not decomposed upon cooking.

See also

• Semicarbazide

References

1. "Azodicarbonamide (CICADS)". Inchem. International Programme on Chemical Safety. Retrieved 2010-08-14.
2. "Azodicarbonamide FCC Grade (98%)". Garuda International, Inc. 2009-02-13. Retrieved 2010-08-14.
3. Joiner, Robert; Marks, Henry (1963). "A New Powdered Agent for Flour Maturing" (PDF). Cereal Chemistry. 40: 539–553. {{cite journal}}: |first2= missing |last2= (help); Unknown parameter |DUPLICATE DATA: last= ignored (help); Unknown parameter |month= ignored (help)
4. Becalski A, Lau BP, Lewis D, Seaman SW (2004-09-10). "Semicarbazide formation in azodicarbonamide-treated flour: a model study". Journal of agricultural and food chemistry. 52 (18). Journal of Agricultural and Food Chemistry: 5730–4. doi:10.1021/jf0495385. PMID 15373416.{{cite journal}}: CS1 maint: multiple names: authors list (link)
5. Cañas, BJ; Diachenko, GW; Nyman, PJ (1997). "Ethyl carbamate levels resulting from azodicarbonamide use in bread". Food Additives & Contaminants. 14 (1): 89–94. doi:10.1080/02652039709374501. PMID 9059587. {{cite journal}}: Unknown parameter |doi_brokendate= ignored (|doi-broken-date= suggested) (help); Unknown parameter |month= ignored (help)
6. "CFR - Code of Federal Regulations Title 21". United States Department of Health and Human Services. 2009-04-01. Retrieved 2010-08-14.
7. "Substances causing/worsening asthma". UK Occupational Health and Safety. WorkSafe Victoria. Retrieved 2010-08-14.
8. "054. Azodicarbonamide (FAO Nutrition Meetings Report Series 40abc)". FAO/WHO. 1966-10-18. Retrieved 2010-08-14.

• Food additives
• Azo compounds
• Commercial baking
• Bleaches