Isobutylidenediurea

Last updated
Isobutylidenediurea
IBDU.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 228-055-8
MeSH C014058
PubChem CID
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
AppearanceWhite solid
Low
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

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]

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<span class="mw-page-title-main">Butyraldehyde</span> Chemical compound

Butyraldehyde, also known as butanal, is an organic compound with the formula CH3(CH2)2CHO. This compound is the aldehyde derivative of butane. It is a colorless flammable liquid with an unpleasant smell. It is miscible with most organic solvents.

<span class="mw-page-title-main">Methacrylic acid</span> Chemical compound

Methacrylic acid, abbreviated MAA, is an organic compound with the formula CH2=C(CH3)COOH. This colorless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its esters, especially methyl methacrylate (MMA), and to poly(methyl methacrylate) (PMMA).

<span class="mw-page-title-main">Semicarbazide</span> Chemical compound

Semicarbazide is the chemical compound with the formula OC(NH2)(N2H3). It is a water-soluble white solid. It is a derivative of urea.

<span class="mw-page-title-main">Crotonaldehyde</span> Chemical compound

Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.

<i>para</i>-Cresidine Chemical compound

para-Cresidine is an organic compound with the formula CH3OC6H3(CH3)NH2. It is a white solid that is soluble in organic solvents. The compound features both amine and methoxy functional groups. It is used as an intermediate in preparation of dyes and pigments.

<span class="mw-page-title-main">Tolidine</span> Chemical compound

2-Tolidine (orthotolidine, o-tolidine; not to be confused with o-toluidine) is an organic compound with the chemical formula (C6H4(CH3)NH2)2. Several isomers are known; the 3-tolidine derivative is also important commercially. It is a colorless compound although commercial samples are often colored. It is slightly soluble in water. It forms salts with acids, such as the hydrochloride, which is commercially available.

<span class="mw-page-title-main">Controlled-release fertiliser</span>

A controlled-release fertiliser (CRF) is a granulated fertiliser that releases nutrients gradually into the soil. Controlled-release fertilizer is also known as controlled-availability fertilizer, delayed-release fertilizer, metered-release fertilizer, or slow-acting fertilizer. Usually CRF refers to nitrogen-based fertilizers. Slow- and controlled-release involve only 0.15% of the fertilizer market (1995).

<span class="mw-page-title-main">3,3'-Dichlorobenzidine</span> Chemical compound

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<span class="mw-page-title-main">Phthalonitrile</span> Chemical compound

Phthalonitrile is an organic compound with the formula C6H4(CN)2, which is an off-white crystal solid at room temperature. It is a derivative of benzene, containing two adjacent nitrile groups. The compound has low solubility in water but is soluble in common organic solvents. The compound is used as a precursor to phthalocyanine and other pigments, fluorescent brighteners, and photographic sensitizers.

Transamidation is a chemical reaction in which an amide reacts with an amine to generate a new amide:

<span class="mw-page-title-main">Bis(hydroxymethyl)urea</span> Chemical compound

Bis(hydroxymethyl)urea is an organic compound with the formula OC(NHCH2OH)2. This white water-soluble solid is an intermediate in the formation of urea-formaldehyde resins. It forms upon treatment of urea with an excess of formaldehyde.

<span class="mw-page-title-main">Methylene diurea</span> Chemical compound

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 methylenediurea deaminase.

Dimethylene triurea (DMTU) is the organic compound with the formula (H2NC(O)NHCH2NH)2CO. It is a white water-soluble solid. The compound is formed by the condensation of formaldehyde with urea. Both branched and linear isomers exist.

<span class="mw-page-title-main">Crotonylidene diurea</span> Chemical compound

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 fertilizers.

<span class="mw-page-title-main">Methylol urea</span> Chemical compound

Methylol urea is the organic compound with the formula H2NC(O)NHCH2OH. It is a white, water-soluble solid that decomposes near 110 °C.

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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