Isobutylidenediurea (abbreviated IBDU) is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
with the formula (CH
3)
2CHCH
2. It is a derivative of urea (OC(NH
2)
2), which itself is highly soluble in water, but IBDU is not. It functions as a
controlled-release fertiliser 224px, Methylene diurea (MDU) is component of the most popular controlled-release fertilizers.
A controlled-release fertiliser (CRF) is a granulated fertiliser that releases nutrients gradually into the soil (i.e., with a controlled release peri ...
owing to its low solubility, which limits the rate of its
hydrolysis
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile.
Biological hydrolys ...
to urea, which is a fast-acting fertiliser.
It is produced by the
condensation reaction
In organic chemistry, a condensation reaction is a type of chemical reaction in which two molecules are combined to form a single molecule, usually with the loss of a small molecule such as water. If water is lost, the reaction is also known as a ...
of
isobutyraldehyde
Isobutyraldehyde is the chemical compound with the formula (CH3)2CHCHO. It is an aldehyde, isomeric with n-butyraldehyde (butanal). Isobutyraldehyde is made, often as a side-product, by the hydroformylation of propene. Its odour is described as ...
and two equivalents of urea:
: (CH
3)
2CHCHO + 2 OC(NH
2)
2 → (CH
3)
2CHCH
2 + H
2O
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
Crotonylidene diurea (CDU) is an organic compound formed by the condensation of crotonaldehyde with two equivalents of urea. It is a white, water-soluble solid. CDU is a component of some controlled-release fertilizer 224px, Methylene diurea (MD ...
(Crotodur). Simpler are various urea-formaldehyde materials such as
ureaform, which consists of
methylene diurea
Methylene diurea (MDU) is the organic compound with the formula CH2(NHC(O)NH2)2. It is a white water-soluble solid. The compound is formed by the condensation of formaldehyde with urea. Methylene diurea is the substrate for the enzyme methylen ...
and
dimethylene triurea.
[{{Ullmann, doi= 10.1002/14356007.n10_n01 , title= Fertilizers, 2. Types , year=2009 , last1=Dittmar , first1=Heinrich , last2=Drach , first2=Manfred , last3=Vosskamp , first3=Ralf , last4=Trenkel , first4=Martin E. , last5=Gutser , first5=Reinhold , last6=Steffens , first6=Günter]
References
Ureas
Soil improvers
Fertilizers