Isobutylidenediurea

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]

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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.025.505
EC Number
  • 228-055-8
MeSH C014058
UNII
  • 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
  • CC(C)C(NC(=O)N)NC(=O)N
Properties
C6H14N4O2
Molar mass 174.204 g·mol−1
Appearance White solid
Low
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.

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