Acetamide

Last updated
Acetamide
Acetamide skeletal.svg
Acetamide-3D-balls.png
Names
Preferred IUPAC name
Acetamide [1]
Systematic IUPAC name
Ethanamide
Other names
Acetic acid amide
Acetylamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.430 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-473-5
KEGG
PubChem CID
RTECS number
  • AB4025000
UNII
  • InChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4) Yes check.svgY
    Key: DLFVBJFMPXGRIB-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)
    Key: DLFVBJFMPXGRIB-UHFFFAOYAC
  • O=C(N)C
Properties
C2H5NO
Molar mass 59.068 g·mol−1
Appearancecolorless, hygroscopic solid
Odor odorless
mouse-like with impurities
Density 1.159 g cm−3
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 [2]
Solubility ethanol 500 g L−1 [2]
pyridine 166.67 g L−1 [2]
soluble in chloroform, glycerol, benzene [2]
log P −1.26
Vapor pressure 1.3 Pa
Acidity (pKa)15.1 (25 °C, H2O) [3]
−0.577 × 10−6 cm3 g−1
1.4274
Viscosity 2.052 cP (91 °C)
Structure
trigonal
Thermochemistry [4]
91.3 J·mol−1·K−1
Std molar
entropy (S⦵298)
115.0 J·mol−1·K−1
−317.0 kJ·mol−1
Hazards
GHS labelling:
GHS-pictogram-silhouette.svg
Warning
H351
P201, P202, P281, P308+P313, P405, P501
NFPA 704 (fire diamond)
3
1
1
Flash point 126 °C (259 °F; 399 K)
Lethal dose or concentration (LD, LC):
7000 mg kg−1 (rat, oral)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Acetamide (systematic name: ethanamide) is an organic compound with the formula CH3CONH2. It is derived from acetic acid. It finds some use as a plasticizer and as an industrial solvent. [5] The related compound N,N-dimethylacetamide (DMA) is more widely used, but it is not prepared from acetamide. Acetamide can be considered an intermediate between acetone, which has two methyl (CH3) groups either side of the carbonyl (CO), and urea which has two amide (NH2) groups in those locations. Acetamide is also a naturally occurring mineral [6] with the IMA symbol: Ace. [7]

Contents

Production

Laboratory scale

Acetamide can be produced in the laboratory from ammonium acetate by dehydration: [8]

[NH4][CH3CO2] → CH3C(O)NH2 + H2O

Alternatively acetamide can be obtained in excellent yield via ammonolysis of acetylacetone under conditions commonly used in reductive amination. [9]

It can also be made from anhydrous acetic acid, acetonitrile and very well dried hydrogen chloride gas, using an ice bath, alongside more valuable reagent acetyl chloride. Yield is typically low (up to 35%), and the acetamide made this way is generated as a salt with HCl.

Industrial scale

In a similar fashion to some laboratory methods, acetamide is produced by dehydrating ammonium acetate or via the hydration of acetonitrile, a byproduct of the production of acrylonitrile.: [5]

CH3CN + H2O → CH3C(O)NH2

Uses

Acetamide is used as a plasticizer and an industrial solvent. [5] Molten acetamide is good solvent with a broad range of applicability. Notably, its dielectric constant is higher than most organic solvents, allowing it to dissolve inorganic compounds with solubilities closely analogous to that of water. [10] Acetamide has uses in electrochemistry and the organic synthesis of pharmaceuticals, pesticides, and antioxidants for plastics. [11] It is a precursor to thioacetamide. [12]

Occurrence

Acetamide has been detected near the center of the Milky Way galaxy. [13] 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 – acetamide, acetone, methyl isocyanate, and propionaldehyde [14] [15] [16] – were seen for the first time on a comet.

In addition, acetamide is found infrequently on burning coal dumps, as a mineral of the same name. [17] [18]

Acetamide crystal structure Acetamide crystal structure.png
Acetamide crystal structure

Related Research Articles

In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine.

<span class="mw-page-title-main">Amide</span> Organic compounds of the form RC(=O)NR′R″

In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula R−C(=O)−NR′R″, where R, R', and R″ represent any group, typically organyl groups or hydrogen atoms. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. It can be viewed as a derivative of a carboxylic acid with the hydroxyl group replaced by an amine group ; or, equivalently, an acyl (alkanoyl) group joined to an amine group.

<span class="mw-page-title-main">Acid–base reaction</span> Chemical reaction

An acid–base reaction is a chemical reaction that occurs between an acid and a base. It can be used to determine pH via titration. Several theoretical frameworks provide alternative conceptions of the reaction mechanisms and their application in solving related problems; these are called the acid–base theories, for example, Brønsted–Lowry acid–base theory.

Acetonitrile, often abbreviated MeCN, is the chemical compound with the formula CH3CN and structure H3C−C≡N. This colourless liquid is the simplest organic nitrile. It is produced mainly as a byproduct of acrylonitrile manufacture. It is used as a polar aprotic solvent in organic synthesis and in the purification of butadiene. The N≡C−C skeleton is linear with a short C≡N distance of 1.16 Å.

<span class="mw-page-title-main">Acetate</span> Salt compound formed from acetic acid and a base

An acetate is a salt formed by the combination of acetic acid with a base. "Acetate" also describes the conjugate base or ion typically found in aqueous solution and written with the chemical formula C
2H
3O−
2. The neutral molecules formed by the combination of the acetate ion and a positive ion are also commonly called "acetates". The simplest of these is hydrogen acetate with corresponding salts, esters, and the polyatomic anion CH
3CO−
2, or CH
3COO−
.

In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group. The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons.

The Brønsted–Lowry theory (also called proton theory of acids and bases) is an acid–base reaction theory which was proposed independently by Johannes Nicolaus Brønsted and Thomas Martin Lowry in 1923. The fundamental concept of this theory is that when an acid and a base react with each other, the acid forms its conjugate base, and the base forms its conjugate acid by exchange of a proton (the hydrogen cation, or H+). This theory is a generalization of the Arrhenius theory.

In chemistry, acetylation is an organic esterification reaction with acetic acid. It introduces an acetyl group into a chemical compound. Such compounds are termed acetate esters or simply acetates. Deacetylation is the opposite reaction, the removal of an acetyl group from a chemical compound.

<span class="mw-page-title-main">Acetone</span> Organic compound ((CH3)2CO); simplest ketone

Acetone, is an organic compound with the formula (CH3)2CO. It is the simplest and smallest ketone. It is a colorless, highly volatile and flammable liquid with a characteristic pungent odor.

Propanamide has the chemical formula CH3CH2C=O(NH2). It is the amide of propanoic acid.

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

Dimethylacetamide (DMAc or DMA) is the organic compound with the formula CH3C(O)N(CH3)2. This colorless, water-miscible, high-boiling liquid is commonly used as a polar solvent in organic synthesis. DMA is miscible with most other solvents, although it is poorly soluble in aliphatic hydrocarbons.

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

Ammonium acetate, also known as spirit of Mindererus in aqueous solution, is a chemical compound with the formula NH4CH3CO2. It is a white, hygroscopic solid and can be derived from the reaction of ammonia and acetic acid. It is available commercially.

Ethylamine, also known as ethanamine, is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It condenses just below room temperature to a liquid miscible with virtually all solvents. It is a nucleophilic base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.

In chemistry, aminolysis (/am·i·nol·y·sis/) is any chemical reaction in which a molecule is lysed by reacting with ammonia or an amine. The case where the reaction involves ammonia may be more specifically referred to as ammonolysis.

Bis(trimethylsilyl)amine (also known as hexamethyldisilazane and HMDS) is an organosilicon compound with the molecular formula [(CH3)3Si]2NH. The molecule is a derivative of ammonia with trimethylsilyl groups in place of two hydrogen atoms. An electron diffraction study shows that silicon-nitrogen bond length (173.5 pm) and Si-N-Si bond angle (125.5°) to be similar to disilazane (in which methyl groups are replaced by hydrogen atoms) suggesting that steric factors are not a factor in regulating angles in this case. This colorless liquid is a reagent and a precursor to bases that are popular in organic synthesis and organometallic chemistry. Additionally, HMDS is also increasingly used as molecular precursor in chemical vapor deposition techniques to deposit silicon carbonitride thin films or coatings.

Carbamic acid, which might also be called aminoformic acid or aminocarboxylic acid, is the chemical compound with the formula H2NCOOH. It can be obtained by the reaction of ammonia NH3 and carbon dioxide CO2 at very low temperatures, which also yields ammonium carbamate [NH4]+[NH2CO2]−. The compound is stable only up to about 250 K (−23 °C); at higher temperatures it decomposes into those two gases. The solid apparently consists of dimers, with the two molecules connected by hydrogen bonds between the two carboxyl groups –COOH.

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

Fluoroboric acid or tetrafluoroboric acid is an inorganic compound with the simplified chemical formula H+[BF4]−. Unlike other strong acids like H2SO4 or HClO4, the pure tetrafluoroboric acid does not exist. The term "fluoroboric acid" refers to a range of chemical compounds, depending on the solvent. The H+ in the simplified formula of fluoroboric acid represents the solvated proton. The solvent can be any suitable Lewis base. For instance, if the solvent is water, fluoroboric acid can be represented by the formula [H3O]+[BF4]−, although more realistically, several water molecules solvate the proton: [H(H2O)n]+[BF4]−. The ethyl ether solvate is also commercially available, where the fluoroboric acid can be represented by the formula [H( 2O)n]+[BF4]−, where n is most likely 2.

Acid–base extraction is a subclass of liquid–liquid extractions and involves the separation of chemical species from other acidic or basic compounds. It is typically performed during the work-up step following a chemical synthesis to purify crude compounds and results in the product being largely free of acidic or basic impurities. A separatory funnel is commonly used to perform an acid-base extraction.

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water and other trace elements.

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

Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is the 3-carbon aldehyde. It is a colourless, flammable liquid with a slightly fruity odour. It is produced on a large scale industrially.

References

  1. ↑ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 841. doi:10.1039/9781849733069-FP001. ISBN   978-0-85404-182-4.
  2. 1 2 3 4 The Merck Index , 14th Edition, 36
  3. ↑ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN   9781498754293.
  4. ↑ John Rumble (June 18, 2018). CRC Handbook of Chemistry and Physics (99th ed.). CRC Press. pp. 5–3. ISBN   978-1138561632.
  5. 1 2 3 "Acetic Acid". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_045.pub2.
  6. ↑ Mindat: Naturally occurring acetamide
  7. ↑ Warr, L.N. (2021). "IMA-CNMNC approved mineral symbols". Mineralogical Magazine. 85 (3): 291–320. Bibcode:2021MinM...85..291W. doi: 10.1180/mgm.2021.43 . S2CID   235729616.
  8. ↑ Coleman, G. H.; Alvarado, A. M. (1923). "Acetamide". Organic Syntheses . 3: 3. doi:10.15227/orgsyn.003.0003.; Collective Volume, vol. 1, p. 3
  9. ↑ Schwoegler, Edward J.; Adkins, Homer (1939). "Preparation of Certain Amines". J. Am. Chem. Soc. 61 (12): 3499–3502. doi:10.1021/ja01267a081.
  10. ↑ Stafford, O. F. (1933). "Acetamide as a Solvent". J. Am. Chem. Soc. 55 (10): 3987–3988. doi:10.1021/ja01337a011.
  11. ↑ Wagner, Frank S. (2002). Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons. doi:10.1002/0471238961.0103052023010714.a02.pub2. ISBN   9780471238966.
  12. ↑ Schwarz, G. (1945). "2,4-Dimethylthiazole". Organic Syntheses . 25: 35.; Collective Volume, vol. 3, p. 332
  13. ↑ 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". Astrophys. J. 643 (1): L25–L28. Bibcode:2006ApJ...643L..25H. doi: 10.1086/505110 .
  14. ↑ Jordans, Frank (30 July 2015). "Philae probe finds evidence that comets can be cosmic labs". The Washington Post. Associated Press. Archived from the original on 23 December 2018. Retrieved 30 July 2015.
  15. ↑ "Science on the Surface of a Comet". European Space Agency. 30 July 2015. Retrieved 30 July 2015.
  16. ↑ 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 . 349 (6247): 493. Bibcode:2015Sci...349..493B. doi: 10.1126/science.aac5116 . PMID   26228139.
  17. ↑ "Acetamide". Mindat.org.
  18. ↑ "Acetamide" (PDF). Handbook of Mineralogy. RRUFF Project.
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