Isobutylidenediurea

Isobutylidenediurea
Names
	Preferred IUPAC name N,N′′-(2-Methylpropane-1,1-diyl)diurea
	Other names Isodur; Diureidoisobutane; Isobutylenediurea; Isobutylidene biurea; 1,1-Diureidisobutane; Isobutylidendiharnstoff;1,1'-Isobutylidenedi-urea; 1,1'-Isobutylidenebisurea; N,N-(isobutylidene)diurea; N,N-(Isobutylidene)bisurea
Identifiers
CAS Number	6104-30-9;
3D model (JSmol)	Interactive image;
ChemSpider	21083;
ECHA InfoCard	100.025.505
EC Number	228-055-8;
MeSH	C014058
PubChem CID	22478;
UNII	20K1225668;
CompTox Dashboard (EPA)	DTXSID8027614 ;
	InChI InChI=1S/C6H14N4O2/c1-3(2)4(9-5(7)11)10-6(8)12/h3-4H,1-2H3,(H3,7,9,11)(H3,8,10,12) Key: QFHMNFAUXJAINK-UHFFFAOYSA-N; InChI=1/C6H14N4O2/c1-3(2)4(9-5(7)11)10-6(8)12/h3-4H,1-2H3,(H3,7,9,11)(H3,8,10,12) Key: QFHMNFAUXJAINK-UHFFFAOYAM;
	SMILES CC(C)C(NC(=O)N)NC(=O)N;
Properties
Chemical formula	C6H14N4O2
Molar mass	174.204 g·mol−1
Appearance	White solid
Solubility in water	Low
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Isobutylidenediurea (abbreviated IBDU) is an organic compound with the formula (CH₃)₂CHCH{NHC(O)NH₂}₂. It is a derivative of urea (OC(NH₂)₂), which itself is highly soluble in water, but IBDU is not. It functions as a controlled-release fertiliser owing to its low solubility, which limits the rate of its hydrolysis to urea, which is a fast-acting fertiliser.^[1]

It is produced by the condensation reaction of isobutyraldehyde and two equivalents of urea:

(CH₃)₂CHCHO + 2 OC(NH₂)₂ → (CH₃)₂CHCH{NHC(O)NH₂}₂ + H₂O

The controlled-release process is the reverse of the above reaction, which only occurs after the IBDU dissolves.

Related materials

A number of CRF's have been developed based on urea. Related to IBDU is crotonylidene diurea (Crotodur). Simpler are various urea-formaldehyde materials such as ureaform, which consists of methylene diurea and dimethylene triurea.^[2]

References

^ C. Nitschke; G. Scherr (2012). "Urea Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o27_o04. ISBN 978-3527306732.
^ Dittmar, Heinrich; Drach, Manfred; Vosskamp, Ralf; Trenkel, Martin E.; Gutser, Reinhold; Steffens, Günter (2009). "Fertilizers, 2. Types". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.n10_n01. ISBN 978-3527306732.

[Ullmann-1] C. Nitschke; G. Scherr (2012). "Urea Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o27_o04. ISBN 978-3527306732.

[Ull-2] Dittmar, Heinrich; Drach, Manfred; Vosskamp, Ralf; Trenkel, Martin E.; Gutser, Reinhold; Steffens, Günter (2009). "Fertilizers, 2. Types". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.n10_n01. ISBN 978-3527306732.

[1]

[2]