60-35-5 Usage
Chemical Description
Acetamide is an organic compound that is used as a solvent and a starting material for the synthesis of various chemicals.
Description
Acetamide, also known as MEA or ethanamide, is the amide of acetic acid. It is a white crystalline solid in pure form with a mousy odor and low toxicity. Acetamide is produced by dehydrating ammonium acetate and is found in red beetroot. It occurs as hexagonal colorless deliquescent crystals with a musty odor and is incompatible with strong acids, strong oxidizing agents, strong bases, and triboluminescent materials.
Uses
Used in Plastic and Chemical Industries:
Acetamide is used as a plasticizer and industrial solvent. Molten acetamide serves as an excellent solvent for many organic and inorganic compounds, making it a versatile option in these industries.
Used as a Solubilizer:
Acetamide renders sparingly soluble substances more soluble in water by mere addition or by fusion, which is beneficial in various applications.
Used as a Stabilizer:
It is used in the manufacture of methylamine and denaturing alcohol, contributing to the stability of these products.
Used in Organic Syntheses:
Acetamide is utilized in organic syntheses, including the production of polymeric materials such as polyvinyl acetamide, which is used as an absorbent.
Used in the Textile Industry:
Acetamide is used as a co-monomer and serves as a wetting agent and penetration accelerator for dyes, making it valuable in the textile industry.
Used in the Cosmetics and Personal Care Industry:
Ethanolamine, an amide made from acetamide and monoethanolamine, is used in the formulation of bubble baths, hair conditioners, shampoos, wave sets, moisturizers, and other bath and hair care products. It increases the water content of the top layers of the skin and enhances the appearance and feel of hair.
Used as a Raw Material:
Acetamide is a raw material in the organic synthesis of methylamine, thioacetamide, and serves as an intermediate in the preparation of medicines, insecticides, and plastics.
Used in Cryoscopy, Soldering, and Other Applications:
As a dipolar solvent, acetamide finds many uses as a solvent for both inorganic and organic compounds. Its solvency has led to widespread uses in cryoscopy, soldering, and the textile industry.
Used in the Lacquer, Explosives, and Cosmetics Industries:
The neutral and amphoteric characteristics of acetamide allow its use as an antacid in these industries.
Used as a Plasticizer in Coatings, Fixtures, Cloth, and Leather:
Acetamide's hygroscopic properties make it useful as a plasticizer in various applications, including coatings, fixtures, cloth, and leather.
Used as a Humectant for Paper:
Acetamide's ability to retain moisture makes it an effective humectant for the paper industry.
Synthesis
Laboratory synthesis can be carried out according to the following steps. Put 3kg glacial acetic acid into a 5L flask and add ammonium carbonate equivalent to 400g ammonia. The flask is equipped with a high-efficiency fractionation column, a condenser and a receiver. Heat the reaction mixture until it boils slowly, adjust the heating so that the distillation rate does not exceed 180mg / h until the top temperature reaches 110 ℃. A mixture of 1400-1500 ml of water and acetic acid was obtained. Change the receiver, slowly increase the heating, and continue the distillation at the same speed until the top temperature rises to 140 ℃. The distillate is 500-700ml, mainly acetic acid, which is reserved for the next feeding. Transfer the residue into a flask with fractionation column and air condenser, distill under normal pressure, and collect the fractions before 210 ℃ and 210-216 ℃ respectively. The latter is acetamide, weighing 1150-1200g. The former can also distill and recover some products. The total weight of the two is 1200-1250g, and the yield is 87% - 90%.
The recrystallization of acetylamine is usually carried out by distillation and solvent recrystallization. The commonly used solvents are acetone, benzene, ethyl acetate, methyl acetate, chloroform, dioxane or the mixture of benzene and ethyl acetate. For example, 1kg of acetamide prepared by the above method is recrystallized with a mixed solvent of 1l benzene and 300ml ethyl acetate to obtain a colorless needle like pure product. The purity of products obtained from industrial production shall not be lower than 98%, and the freezing point shall not be lower than 76 ℃.
Air & Water Reactions
Deliquescent. Very soluble in water.
Reactivity Profile
Acetamide may react with azo and diazo compounds to generate toxic gases. May form flammable gases with strong reducing agents. Reacts as a weak bases (weaker than water). Mixing with dehydrating agents such as P2O5 or SOCl2 generates acetonitrile Burns to give toxic mixed oxides of nitrogen (NOx).
Health Hazard
After oral exposures to acetamide, animals developed liver tumors. However, no informa-
tion is available on the carcinogenic effects of acetamide in humans. The US EPA has not
classifi
ed acetamide for carcinogenicity. The IARC has classifi
ed acetamide as a Group 2B,
meaning a possible human carcinogen.
Health Hazard
Mild irritant; acute oral toxicity in animals very low; oral LD50 value (rats):7000 mg/kg; carcinogenic to animals; oraladministration caused blood and liver tumorsin mice and rats; carcinogenicity: animal limited evidence, no evidence in humans.
Fire Hazard
The flash point of Acetamide has not been determined, but Acetamide is probably combustible.
Safety Profile
Suspected carcinogen with experimental carcinogenic and neoplastigenic data. Moderately toxic by intraperitoneal and possibly other routes. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. See also AMIDES. When heated to decomposition it emits toxic fumes of NOx,.
Potential Exposure
Used as a stabilizer, plasticizer, wetting agent; solvent in plastics, lacquers, explosive; soldering flux ingredient; and chemical manufacturing
Carcinogenicity
The IARC has determined that there is
sufficient evidence of carcinogenicity for
acetamide in experimental animals and that it
is possibly carcinogenic to humans.
Environmental Fate
The mechanism of toxicity of acetamide is not known; the
response profile is quite different from the better studied
dimethyl derivative. Acetamide appears to be in a class of
chemicals which, although producing liver cancer in rodents, is
less sensitive to inactive in genetic tests looking at formation of
micronuclei. The carcinogenic response in rodents appears
related to the formation of hydroxylamine from the primary
metabolite acetohydroxamic acid.
storage
Acetamide should be kept stored in a tightly closed container, in a cool, dry, ventilated area. It should be protected against physical damage, away from any source of heat, ignition, or oxidizing materials.
Shipping
UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required
Purification Methods
Acetamide is crystallised by dissolving in hot MeOH (0.8mL/g), diluting with Et2O and allowing to stand [Wagner J Chem Edu 7 1135 1930]. Alternate crystallisation solvents are acetone, *benzene, chloroform, dioxane, methyl acetate or *benzene/ethyl acetate mixtures (3:1 and 1:1). It has also been recrystallised from hot water after treating with HCl-washed activated charcoal (which had been repeatedly washed with water until free from chloride ions), then crystallised again from hot 50% aqueous EtOH and finally twice from hot 95% EtOH [Christoffers & Kegeles J Am Chem Soc 85 2562 1963]. Finally it is dried in a vacuum desiccator over P2O5. Acetamide is also purified by distillation (b 221-223o) or by sublimation in vacuo. It has also been purified by two recrystallisations from cyclohexane containing 5% (v/v) of *benzene. Needle-like crystals separate and are filtered, washed with a small volume of distilled H2O and dried with a flow of dry N2. [Slebocka-Tilk et al. J Am Chem Soc 109 4620 1987, Beilstein 2 H 175, 2 I 80, 2 II 177, 2 III 384, 2 IV 399.]
Toxicity evaluation
Acetamide will exist as a vapor in the ambient atmosphere.
Atmospheric degradation occurs by reaction with photochemically
produced hydroxyl radicals. The half-life for this
reaction in air is estimated to be 7.6 days. If released to soil,
acetamide is expected to have very high mobility and is not
expected to adsorb to suspended solids and sediment. Experiments
suggest that this chemical may break down in the
environment through biodegradation and not through hydrolysis.
Volatilization from water surfaces is not expected to be an
important fate process based on this compound’s estimated
Henry’s law constant.
Incompatibilities
Reacts with strong acids, such as hydrochloric, sulfuric, and nitric, strong oxidizers; strong bases; strong reducing agents such as hydrides; ammoniaisocyanates, phenols, cresols. Contact with water causes slow hydrolyzation to ammonia and acetate salts.
Waste Disposal
Add to alcohol or benzene as a flammable solvent and incinerate; oxides of nitrogen produced may be scrubbed out with alkaline solution. All federal, state, and local environmental regulations must be observed.
Precautions
During handling and/use of acetamide, workers should wear special protective equipment. After leaving work areas, workers should wash hands, face, forearms, and neck, dispose of outer clothing, and change to clean garments at the end of the day.
Check Digit Verification of cas no
The CAS Registry Mumber 60-35-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 0 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 60-35:
(4*6)+(3*0)+(2*3)+(1*5)=35
35 % 10 = 5
So 60-35-5 is a valid CAS Registry Number.
InChI:InChI=1/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)
60-35-5Relevant articles and documents
The 3rd degree of biomimetism: Associating the cavity effect, ZnII coordination and internal base assistance for guest binding and activation
Parrot,Collin,Bruylants,Reinaud
, p. 5479 - 5487 (2018)
The synthesis and characterization of a resorcinarene-based tetra(imidazole) ligand is reported. The properties of the corresponding ZnII complex are studied in depth, notably by NMR spectroscopy. In MeCN, acid-base titration reveals that one out of the four imidazole arms is hemi-labile and can be selectively protonated, thereby opening a coordination site in the exo position. Quite remarkably, the 4th imidazole arm promotes binding of an acidic molecule (a carboxylic acid, a β-diketone or acetamide), by acting as an internal base, which allows guest binding as an anion to the metal center in the endo position. Most importantly, the presence of this labile imidazole arm makes the ZnII complex active for the catalyzed hydration of acetonitrile. It is proposed that it acts as a general base for activating a water molecule in the vicinity of the metal center during its nucleophilic attack to the endo-bound MeCN substrate. This system presents a unique degree of biomimetism when considering zinc enzymes: a pocket for guest binding, a similar first coordination sphere, a coordination site available for water activation in the cis position relative to the substrate and finally an internal imidazole residue that plays the role of a general base.
Swift, E. H.,Butler, E. A.
, p. 146 - 153 (1956)
Measurement and calculation of the rate constant for the reaction of isopropyl isocyanate with hydroxyl radical
Parker, James K.,Espada-Jallad, Cyntia,Parker, Claudia L.,Witt, John D.
, p. 187 - 197 (2009)
The rate constant for the gas-phase reaction of hydroxyl radical with isopropyl isocyanate (IIC) has been measured, relative to toluene, in the T =287-321 K range at atmospheric pressure in air. Ultraviolet photolysis of methyl nitrite served as the sourc
EXAFS/FTIR Characterization and Selective Hydration of Acetonitrile on Silica-Supported *)4V6O19>
Yamaguchi, Masatsugu,Shido, Takafumi,Ohtani, Hiroko,Isobe, Kiyoshi,Ichikawa, Masaru
, p. 717 - 718 (1995)
Silica-supported *)4V6O19 exhibited high catalytic activities in the gas-phase hydration of acetonitrile towards acetamide at 350-473 K with selectivity of over 97percent and dehydrogenation of 2-propanol to acetone.EXAFS, XPS and FTIR studies suggested that thermal evacuation of silica-supported *)4V6O19> at 473 K led to the removal of the bridged oxygen atoms in the V6O19 framework.The resulting deoxygenated samples enhanced the acetonitrile hydration, while catalyzed the dehydration of 2-propanol to propene besides the dehydrogenation reaction, probably owing to the newly generated Lewis acid site.
Karrer,Haab
, p. 950,956 (1949)
Catalytic hydration of benzonitrile and acetonitrile using nickel(0)
Crestani, Marco G.,Arevalo, Alma,Garcia, Juventino J.
, p. 732 - 742 (2006)
The homogeneous catalytic hydration of benzo- and acetonitrile under thermal conditions was achieved using nickel(0) compounds of the type [(dippe)Ni(η2-NCR)] with R = phenyl or methyl (compounds 1 and 2, respectively), as the specific starting intermediates. Alternatively, the complexes may be prepared in situ by direct reaction of the precursor [(dippe)NiH]2 (3) with the respective nitrile. Hydration appears to occur homogeneously, as tested by mercury drop experiments, producing benzamide and acetamide, respectively. Addition of Bu4NI did not lead to catalysis inhibition, suggesting the prevalence of Ni(0) intermediates during catalysis. Hydration using analogous complexes of 3, such as [(dtbpe)NiH] 2 (4) and [(dcype)NiH]2 (5) was also addressed.
Unmasking the Action of Phosphinous Acid Ligands in Nitrile Hydration Reactions Catalyzed by Arene-Ruthenium(II) Complexes
Tomás-Mendivil, Eder,Cadierno, Victorio,Menéndez, María I.,L?pez, Ram?n
, p. 16874 - 16886 (2015)
The catalytic hydration of benzonitrile and acetonitrile has been studied by employing different arene-ruthenium(II) complexes with phosphinous (PR2OH) and phosphorous acid (P(OR)2OH) ligands as catalysts. Marked differences in activity were found, depending on the nature of both the P-donor and η6-coordinated arene ligand. Faster transformations were always observed with the phosphinous acids. DFT computations unveiled the intriguing mechanism of acetonitrile hydration catalyzed by these arene-ruthenium(II) complexes. The process starts with attack on the nitrile carbon atom of the hydroxyl group of the P-donor ligand instead of on a solvent water molecule, as previously suggested. The experimental results presented herein for acetonitrile and benzonitrile hydration catalyzed by different arene-ruthenium(II) complexes could be rationalized in terms of such a mechanism.
Half-Sandwich Iridium Complexes Based on β-Ketoamino Ligands: Preparation, Structure, and Catalytic Activity in Amide Synthesis
Wang, Yang,Guo, Wen,Guan, Ai-Lin,Liu, Shuang,Yao, Zi-Jian
, p. 11514 - 11520 (2021/07/31)
A series of β-ketoamino-based N,O-chelate half-sandwich iridium complexes with the general formula [Cp*IrClL] have been prepared in good yields. These air-insensitive iridium complexes showed desirable catalytic activity in an amide preparation under mild conditions. A number of amides with diverse substituted groups were furnished in a one-pot reaction with good-to-excellent yields through an amidation reaction of NH2OH·HCl with aldehydes in the presence of these iridium(III) precursors. The excellent catalytic activity, mild reaction conditions, and broad substrate scope gave this type of iridium catalyst potential for use in industry. All of the obtained iridium complexes were well characterized by different spectroscopy techniques. The exact molecular structure of complex 3 has been confirmed by single-crystal X-ray analysis.
Manganese-Pincer-Catalyzed Nitrile Hydration, α-Deuteration, and α-Deuterated Amide Formation via Metal Ligand Cooperation
Ben-David, Yehoshoa,Diskin-Posner, Yael,Kar, Sayan,Milstein, David,Zhou, Quan-Quan,Zou, You-Quan
, p. 10239 - 10245 (2021/08/24)
A simple and efficient system for the hydration and α-deuteration of nitriles to form amides, α-deuterated nitriles, and α-deuterated amides catalyzed by a single pincer complex of the earth-abundant manganese capable of metal-ligand cooperation is reported. The reaction is selective and tolerates a wide range of functional groups, giving the corresponding amides in moderate to good yields. Changing the solvent from tert-butanol to toluene and using D2O results in formation of α-deuterated nitriles in high selectivity. Moreover, α-deuterated amides can be obtained in one step directly from nitriles and D2O in THF. Preliminary mechanistic studies suggest the transformations contributing toward activation of the nitriles via a metal-ligand cooperative pathway, generating the manganese ketimido and enamido pincer complexes as the key intermediates for further transformations.
Metal-Free Solvent Promoted Oxidation of Benzylic Secondary Amines to Nitrones with H2O2
Adrio, Javier,Amarante, Giovanni Wilson,Granato, álisson Silva
, p. 13817 - 13823 (2021/10/01)
An environmentally benign protocol for the generation of nitrones from benzylic secondary amines via catalyst-free oxidation of secondary amines using H2O2 in MeOH or CH3CN is described. This methodology provides a selective access to a variety of C-aryl nitrones in yields of 60 to 93%. Several studies have been performed to shed light on the reaction mechanism and the role of the solvent.