Oxamide

Oxamide
Oxamide
Identifiers
CAS number 471-46-5
Properties
Molecular formula C2H4N2O2
Molar mass 88.0654 g/mol
Appearance White powder
Density 1.667 g/cm3
Solubility in water Soluble
Solubility ethanol
Hazards
EU classification Mild Irritant (6.1)
R-phrases R36
S-phrases S25
Flash point >300 °C
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Oxamide is the organic compound with the formula (CONH2)2. This white crystalline solid is soluble in ethanol, slightly soluble in water and insoluble in diethyl ether. Oxamide is the diamide derived from oxalic acid.

Contents

Production and applications

Oxamide is produced from hydrogen cyanide, which is oxidized to cyanogen, which is then hydrolyzed.[1]

The main application is as substitute urea in fertilizers. Oxamide hydrolyzes (releases ammonia) very slowly, which is sometimes preferred vs the quick release by urea.

It is used as a stabilizer for nitrocellulose preparations. It also finds use in APCP rocket motors as a high performance burn rate suppressant. The use of oxamide in concentrations of 1-3 wt% has shown to slow the linear burn rate while having minimal impact on propellant specific impulse.

Reactions

Upon heating above 350 °C, it decomposes to cyanogen and water. Oxamide forms self-assembled monolayers consisting of a hydrogen bonded network.[2]

References

  1. ^ Wilhelm Riemenschneider, Minoru Tanifuji "Oxalic Acid" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a18_247.
  2. ^ Nguyen T.L., Fowler F.W., Lauher J.W., "Commensurate and incommensurate hydrogen bonds. An exercise in crystal engineering." Journal of the American Chemical Society, 123(44), pp. 11057-64, 2001. doi:10.1021/ja016635v

External links


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Look at other dictionaries:

  • oxamide — ● oxamide ou oxalamide nom masculin Diamide H2N―CO―CO―NH2 de l acide oxalique. ⇒OXAMIDE, subst. masc. CHIM. Poudre blanche microcristalline, presque insoluble dans l eau, que l on obtient en décomposant à chaud l oxalate d ammonium (d apr. GRAND …   Encyclopédie Universelle

  • Oxamide — Ox*am ide, n, [Oxalic + amide.] (Chem.) A white crystalline neutral substance ({C2O2(NH2)2)} obtained by treating ethyl oxalate with ammonia. It is the acid amide of oxalic acid. Formerly called also {oxalamide}. [1913 Webster] …   The Collaborative International Dictionary of English

  • oxamide — oksamidas statusas T sritis chemija formulė (CONH₂)₂ atitikmenys: angl. oxamide rus. оксамид ryšiai: sinonimas – etandiamidas …   Chemijos terminų aiškinamasis žodynas

  • oxamide — noun A white crystalline solid, the double amide of oxalic acid, used as a stabilizer for nitrocellulose preparations and as a substitute for urea in fertilizers …   Wiktionary

  • oxamide — (o ksa mi d ) s. m. Produit de distillation de l oxalate d ammoniaque …   Dictionnaire de la Langue Française d'Émile Littré

  • oxamide — ox·amide …   English syllables

  • oxamide — äkˈsamə̇d; ˈäksəˌmīd, mə̇d noun Etymology: International Scientific Vocabulary ox (II) + amide; originally formed in French : a high melting crystalline amide (CONH2)2 obtainable by treating ethyl oxalate with ammonia : the diamide of oxalic acid …   Useful english dictionary

  • diphenyl oxamide — Oxanilide Ox*an i*lide, n. [Oxalic + aniline + amide.] (Chem.) A white crystalline substance, resembling oxanilamide, obtained by heating aniline oxalate, and regarded as a double anilide of oxalic acid; called also {diphenyl oxamide}. [1913… …   The Collaborative International Dictionary of English

  • phenyl oxamide — Oxanilamide Ox a*nil*am ide, n. [Oxanilic + amide.] (Chem.) A white crystalline nitrogenous substance, obtained indirectly by the action of cyanogen on aniline, and regarded as an anilide of oxamic acid; called also {phenyl oxamide}. [1913… …   The Collaborative International Dictionary of English

  • C2O2NH22 — Oxamide Ox*am ide, n, [Oxalic + amide.] (Chem.) A white crystalline neutral substance ({C2O2(NH2)2)} obtained by treating ethyl oxalate with ammonia. It is the acid amide of oxalic acid. Formerly called also {oxalamide}. [1913 Webster] …   The Collaborative International Dictionary of English

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