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Acetamide

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Title: Acetamide  
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Subject: Carboxamide, Amide, Potassium chloride, Oxygen, Acetonitrile
Collection: Acetamides, Hazardous Air Pollutants, Iarc Group 2B Carcinogens, Plasticizers
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Acetamide

Acetamide
Names
IUPAC names
Acetamide
Ethanamide
Other names
acetic acid amide
Identifiers
 Y
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
DrugBank  Y
EC number 200-473-5
Jmol-3D images Image
KEGG  Y
PubChem
RTECS number AB4025000
UNII  Y
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
Harmful (Xn)
Carc. Cat. 3
R-phrases R40
S-phrases (S2) S36/37
NFPA 704
1
3
1
Flash point 126 °C (259 °F; 399 K)
Lethal dose or concentration (LD, LC):
LD50 (Median dose)
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).
 Y  (: Y/N?)

Acetamide (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.

Contents

  • Production 1
    • Laboratory scale 1.1
    • Industrial scale 1.2
  • Use 2
  • Occurrence 3
  • References 4
  • External links 5

Production

Laboratory scale

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

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

Occurrence

Acetamide has been detected near the center of the Earth) can form in space.

On 30 July 2015, scientists reported that upon the first touchdown of the 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

  1. ^ a b c d The Merck Index, 14th Edition, 36
  2. ^ a b "Acetic Acid",  
  3. ^ Coleman, G. H.; Alvarado, A. M. (1923). "Acetamide".  
  4. ^ Schwoegler, Edward J.; Adkins, Homer (1939). "Preparation of Certain Amines". Journal of the American Chemical Society 61 (12): 3499–3502.  
  5. ^ Hollis, J. M.; Lovas, F. J.; Remijan, A. J.; Jewell, P. R.; Ilyushin, V. V.; Kleiner, I. (2006). ): The Largest Interstellar Molecule with a Peptide Bond"2CONH3"Detection of Acetamide (CH (pdf). The Astrophysical Journal 643 (1): L25–L28.  
  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".  
  9. ^ "Acetamide". Mindat.org. 
  10. ^ "Acetamide" (pdf). Handbook of Mineralogy. RRUFF Project. 

External links

  • International Chemical Safety Card 0233
  • "Acetamide". Webmineral.org. 
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