2-Cyanoguanidine

From Wikipedia, the free encyclopedia
Jump to: navigation, search
2-Cyanoguanidine
Skeletal formulaπ
Ball-and-stick model
Names
IUPAC name
2-Cyanoguanidine
Other names
Cyanoguanidine, dicyanodiamide, N-cyanoguanidine, 1-cyanoguanidine, Guanidine-1-carbonitrile, dicyandiamin, Didin, DCD, Dicy
Identifiers
461-58-5 YesY
ChemSpider 9611 YesY
EC number 207-312-8
Jmol-3D images Image
PubChem 10005
RTECS number ME9950000
Properties
C2H4N4
Molar mass 84.08 g/mol
Appearance White crystals
Density 1.400 g/cm3
Melting point 209.5 °C (409.1 °F; 482.6 K)
Boiling point 252 °C (486 °F; 525 K)
41.3 g/l
log P -0.52
2.25·10−10 atm.m3/mol
Hazards
Main hazards harmful (Xn)
R-phrases R20/21/22
S-phrases S24/25
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 YesY verify (what isYesY/N?)
Infobox references

2-Cyanoguanidine is an nitrile derived from guanidine. It is a dimer of cyanamide, from which it can be prepared. 2-Cyanoguanidine is a colourless solid that is soluble in water, acetone, and alcohol, but not nonpolar organic solvents.[1]

Production and use[edit]

2-Cyanoguanidine is produced by treating cyanamide with base. It is produced in soil by decomposition of cyanamide. A variety of useful compounds are produced from 2-cyanoguanidine, guanidines and melamine. It is also used as a slow fertilizer. Formerly, it was used as a fuel in some explosives. It is used in the adhesive industry as a curing agent for epoxies.[1]

Chemistry[edit]

There are two tautomeric forms, differing in the protonation and bonding of the nitrogen to which the nitrile group is attached.

Dicyandiamide tautomerism.png

2-Cyanoguanidine can also exist in a zwitterionic form via a formal acid–base reaction among the nitrogens.

Cyanoguanidine zwitterion.png

Loss of ammonia (NH3) from the zwitterionic form, followed by deprotonation of the remaining central nitrogen atom, gives the dicyanamide anion, [N(CN)2].

Controversy[edit]

In September 2012, traces of dicyandiamide were found in milk produced by New Zealand company Fonterra.[2] Fonterra, Federated Farmers, and the Government moved quickly to reassure the public and overseas buyers there was no risk to health.[3] Fonterra has received praise for its handling of the DCD issue.[4] The levels were very low and attempts were made to prevent the test results from being reported in the media.[5]

References[edit]

  1. ^ a b Thomas Güuthner; Bernd Mertschenk (2006). "Cyanamides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_139.pub2. 
  2. ^ "Government downplays DCD risk". 3 News NZ. January 27, 2013. 
  3. ^ Astley, Mark (January 28, 2013). "Government defends Fonterra's safety". 3 News NZ. 
  4. ^ "DCD concerns: NZ handling of crisis was ‘textbook’ - Rabobank". Dairy Reporter. February 21, 2013. 
  5. ^ Watkins, Tracy (14 April 2013). "Secrecy Over DCD In Milk Scare Revealed". Sunday Star-Times. Retrieved 13 April 2013. 

External links[edit]