Dimethylene triurea

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Dimethylene triurea
Dimethylene triurea.svg
Names
Preferred IUPAC name
5-Oxa-2,4,6,8-tetraazanonane-1,9-diamide
Other names
methylenebis(urea), 5-oxo-2,4,6,8-Tetraazanonanediamide, 1,3-bis[(carbamoylamino)methyl]urea
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 604-987-4
KEGG
PubChem CID
  • InChI=1S/C5H12N6O3/c6-3(12)8-1-10-5(14)11-2-9-4(7)13/h1-2H2,(H3,6,8,12)(H3,7,9,13)(H2,10,11,14)
    Key: OKNSZPQWMKXIEO-UHFFFAOYSA-N
  • C(NC(=O)N)NC(=O)NCNC(=O)N
Properties
C5H12N6O3
Molar mass 204.190 g·mol−1
Appearancewhite solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

Applications

DMTU is an intermediate in the production of urea-formaldehyde resins. [1]

Together with methylene diurea, DMTU is a component of some controlled-release fertilizers. [2]

Related Research Articles

Urea, also called carbamide, is an organic compound with chemical formula CO(NH2)2. This amide has two amino groups joined by a carbonyl functional group. It is thus the simplest amide of carbamic acid.

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

Pentaerythritol is an organic compound with the formula C(CH2OH)4. Classified as a polyol, it is a white solid. Pentaerythritol is a building block for the synthesis and production of explosives, plastics, paints, appliances, cosmetics, and many other commercial products.

<span class="mw-page-title-main">Formaldehyde</span> Organic compound (H–CHO); simplest aldehyde

Formaldehyde is a naturally occurring organic compound with the formula CH2O and structure H−CHO. The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde, hence it is stored as an aqueous solution (formalin), which is also used to store animal specimens. It is the simplest of the aldehydes and one of the simplest of the carbohydrates. The common name of this substance comes from its similarity and relation to formic acid.

<span class="mw-page-title-main">Hemiaminal</span> Organic compound or group with a hydroxyl and amine attached to the same carbon

In organic chemistry, a hemiaminal is a functional group or type of chemical compound that has a hydroxyl group and an amine attached to the same carbon atom: −C(OH)(NR2)−. R can be hydrogen or an alkyl group. Hemiaminals are intermediates in imine formation from an amine and a carbonyl by alkylimino-de-oxo-bisubstitution. Hemiaminals can be viewed as a blend of aminals and geminal diol. They are a special case of amino alcohols.

Urea-formaldehyde (UF), also known as urea-methanal, so named for its common synthesis pathway and overall structure, is a nontransparent thermosetting resin or polymer. It is produced from urea and formaldehyde. These resins are used in adhesives, plywood, particle board, medium-density fibreboard (MDF), and molded objects. In agriculture, urea-formaldehyde compounds are one of the most commonly used types of slow-release fertilizer.

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

Sulfamic acid, also known as amidosulfonic acid, amidosulfuric acid, aminosulfonic acid, sulphamic acid and sulfamidic acid, is a molecular compound with the formula H3NSO3. This colourless, water-soluble compound finds many applications. Sulfamic acid melts at 205 °C before decomposing at higher temperatures to water, sulfur trioxide, sulfur dioxide and nitrogen.

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

Biuret is a chemical compound with the chemical formula HN(CONH2)2. It is a white solid that is soluble in hot water. A variety of organic derivatives are known. The term "biuret" also describes a family of organic compounds with the chemical formula R1R2N−C(=O)−N(R3)−C(=O)−NR4R5, where R1, R2, R3, R4 and R5 are hydrogen, organyl or other groups. Also known as carbamylurea, it results from the condensation of two equivalents of urea. It is a common undesirable impurity in urea-based fertilizers, as biuret is toxic to plants.

<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.

<span class="mw-page-title-main">Melamine resin</span> Hard, thermosetting plastic material often used in dinnerware

Melamine resin or melamine formaldehyde is a resin with melamine rings terminated with multiple hydroxyl groups derived from formaldehyde. This thermosetting plastic material is made from melamine and formaldehyde. In its butylated form, it is dissolved in n-butanol and xylene. It is then used to cross-link with alkyd, epoxy, acrylic, and polyester resins, used in surface coatings. There are many types, varying from very slow to very fast curing.

<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">Formaldehyde releaser</span> Chemical compound used as a preservative that slowly releases formaldehyde.

A formaldehyde releaser, formaldehyde donor or formaldehyde-releasing preservative is a chemical compound that slowly releases formaldehyde. Formaldehyde-releasers are added to prevent microbial growth and extend shelf life. The intent of these compounds is that they release formaldehyde at levels that suppress microbial growth but sufficiently low to not threaten humans. The use of these chemicals in cosmetics has elicited controversy.

A thermoset polymer matrix is a synthetic polymer reinforcement where polymers act as binder or matrix to secure in place incorporated particulates, fibres or other reinforcements. They were first developed for structural applications, such as glass-reinforced plastic radar domes on aircraft and graphite-epoxy payload bay doors on the Space Shuttle.

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

Dimethylol ethyleneurea is an organic compound derived from formaldehyde and urea. It is a colourless solid that is used for treating cellulose-based heavy fabrics to inhibit wrinkle formation. Dimethylol ethylene urea (DMEU) bonds with the hydroxyl groups present in long cellulose chains and prevents the formation hydrogen bonding between the chains, the primary cause of wrinkling. This treatment produces permanently wrinkle-resistant fabrics and is different from the effects achieved from using fabric softeners. An additional names for DMEU includes 1,3-bis(hydroxymethyl)-tetrahydro-2-imidazolone.

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

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.

<span class="mw-page-title-main">Ureas</span>

In chemistry, ureas are a class of organic compounds with the formula (R2N)2CO where R = H, alkyl, aryl, etc. Thus, in addition to describing the specific chemical compound urea ((H2N)2CO), urea is the name of a functional group that is found in many compounds and materials of both practical and theoretical interest. Generally ureas are colorless crystalline solids, which, owing to the presence of fewer hydrogen bonds, exhibit melting points lower than that of urea itself.

<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.

<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.

Hydroxymethylation is a chemical reaction that installs the CH2OH group. The transformation can be implemented in many ways and applies to both industrial and biochemical processes.

References

  1. Steinhof, Oliver; Kibrik, Éléonore J.; Scherr, Günter; Hasse, Hans (2014). "Quantitative and qualitative1H, 13C, and15N NMR spectroscopic investigation of the urea-formaldehyde resin synthesis". Magnetic Resonance in Chemistry. 52 (4): 138–162. doi:10.1002/mrc.4044. PMID   24496721. S2CID   1457586.
  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.