Acetamide

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Acetamide
Acetamide skeletal.svg
Acetamide-3D-balls.png
Names
IUPAC names
Acetamide
Ethanamide
Other names
acetic acid amide
Identifiers
60-35-5 YesY
ChEBI CHEBI:27856 YesY
ChEMBL ChEMBL16081 YesY
ChemSpider 173 YesY
DrugBank DB02736 YesY
EC number 200-473-5
4661
Jmol-3D images Image
KEGG C06244 YesY
PubChem 178
RTECS number AB4025000
UNII 8XOE1JSO29 YesY
Properties
C2H5NO
Molar mass 59.07 g·mol−1
Appearance colorless, hygroscopic
Odor odorless
mouse-like with impurities
Density 1.159 g/cm3
Melting point 79 to 81 °C (174 to 178 °F; 352 to 354 K)
Boiling point 221.2 °C (430.2 °F; 494.3 K) (decomposes)
2000 g L−1[1]
Solubility ethanol 500 g L−1[1]
pyridine 166.67 g L−1[1]
soluble in chloroform, glycerol, benzene[1]
log P -1.26
Vapor pressure 1.3 Pa
Acidity (pKa) 16.5
1.4274
Viscosity 2.052 cP (91 °C)
Structure
trigonal
Hazards
Safety data sheet External MSDS
EU classification Harmful (Xn)
Carc. Cat. 3
R-phrases R40
S-phrases (S2) S36/37
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 126 °C (259 °F; 399 K)
Lethal dose or concentration (LD, LC):
700 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 YesY verify (what isYesY/N?)
Infobox references

Acetamide (IUPAC: ethanamide) is an organic compound with the formula CH3CONH2. It is the simplest amide derived from acetic acid. It finds some use as a plasticizer and as an industrial solvent.[2] The related compound N,N-dimethylacetamide (DMA) is more widely used, but it is not prepared from acetamide.

Production[edit]

Laboratory scale[edit]

Acetamide can be produced in the laboratory by dehydrating ammonium acetate:[3]

CH3COONH4 → CH3C(O)NH2 + H2O

Alternatively acetamide can be obtained in excellent yield via ammonolysis of acetylacetone under conditions commonly used in reductive amination.[4]

Industrial scale[edit]

In a similar fashion to some laboratory methods, acetamide is produced dehydrating ammonium acetate or via the hydrolysis of acetonitrile, a byproduct of the production of acrylonitrile:[2]

CH3CN + H2O → CH3C(O)NH2

Use[edit]

Occurrence[edit]

Acetamide has been detected near the center of the Milky Way galaxy.[5] This finding is potentially significant because acetamide has an amide bond, similar to the essential bond between amino acids in proteins. This finding lends support to the theory that organic molecules that can lead to life (as we know it on Earth) can form in space.

On 30 July 2015, scientists reported that upon the first touchdown of the Philae lander on comet 67/P‍‍ '​‍s surface, measurements by the COSAC and Ptolemy instruments revealed sixteen organic compounds, four of which were seen for the first time on a comet, including acetamide, acetone, methyl isocyanate and propionaldehyde.[6][7][8]

In addition, acetamide is found infrequently on burning coal dumps, as a mineral of the same name.[9][10]

Acetamide crystal structure

References[edit]

  1. ^ a b c d The Merck Index, 14th Edition, 36
  2. ^ a b "Acetic Acid", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a01_045.pub2 
  3. ^ Coleman, G. H.; Alvarado, A. M. (1923). "Acetamide". Org. Synth. 3: 3. ; Coll. Vol. 1, p. 3 
  4. ^ Schwoegler, Edward J.; Adkins, Homer (1939). "Preparation of Certain Amines". Journal of the American Chemical Society 61 (12): 3499–3502. doi:10.1021/ja01267a081. 
  5. ^ Hollis, J. M.; Lovas, F. J.; Remijan, A. J.; Jewell, P. R.; Ilyushin, V. V.; Kleiner, I. (2006). "Detection of Acetamide (CH3CONH2): The Largest Interstellar Molecule with a Peptide Bond" (pdf). The Astrophysical Journal 643 (1): L25–L28. Bibcode:2006ApJ...643L..25H. doi:10.1086/505110. 
  6. ^ Jordans, Frank (30 July 2015). "Philae probe finds evidence that comets can be cosmic labs". The Washington Post. Associated Press. Retrieved 30 July 2015. 
  7. ^ "Science on the Surface of a Comet". European Space Agency. 30 July 2015. Retrieved 30 July 2015. 
  8. ^ Bibring, J.-P.; Taylor, M.G.G.T.; Alexander, C.; Auster, U.; Biele, J.; Finzi, A. Ercoli; Goesmann, F.; Klingehoefer, G.; Kofman, W.; Mottola, S.; Seidenstiker, K.J.; Spohn, T.; Wright, I. (31 July 2015). "Philae's First Days on the Comet - Introduction to Special Issue". Science (journal) 349 (6247): 493. doi:10.1126/science.aac5116. Retrieved 30 July 2015. 
  9. ^ "Acetamide". Mindat.org. 
  10. ^ "Acetamide" (pdf). Handbook of Mineralogy. RRUFF Project. 

External links[edit]