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.
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 ℃.
Description
Acetamide (MEA or ethanamide), the amide of acetic acid, is a white crystalline solid in pure form with a mousy odor. Low toxicity. It is produced by dehydrating ammonium acetate. Acetamide is found in red beetroot.
Acetamide is used primarily as a solvent, plasticizer, and a wetting and penetrating agent. it was used as an intermediate in the synthesis of methylamine, thioacetamide, hypnotics, insecticides, medicinals and various plastics, a soldering flux ingredient, a wetting agent and penetration accelerator for dyes, and as a plasticizer in leather, cloth and coatings.
ethanolamine is an amide made from acetamide and monoethanolamine. It is a clear liquid. In cosmetics and personal care products, It 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 by drawing moisture from the surrounding air. It also enhances the appearance and feel of hair, by increasing hair body, suppleness, or sheen, or by improving the texture of hair that has been damaged physically or by chemical treatment.
Chemical Properties
Different sources of media describe the Chemical Properties of 60-35-5 differently. You can refer to the following data:
1. Acetamide occurs as hexagonal colourless deliquescent crystals with a musty odour. It is incompatible with strong acids, strong oxidising agents, strong bases, and triboluminescent materials. Acetamide is used primarily as a solvent, a plasticiser, and a wetting and penetrating agent. Workplace exposures to acetamide are associated with the plastic and chemical industries.
2. Acetamide is a colorless to yellow, deliquescent, crystalline solid. Odorless if pure, “mousy” odor if impure. Odor threshold5140 160 milligram per cubic meter.
Uses
Different sources of media describe the Uses of 60-35-5 differently. You can refer to the following data:
1. Acetamide is often used as plasticizer and as industrial solvent.
molten acetamide is an excellent solvent for many organic and inorganic compounds.
Solubilizer.
renders sparingly soluble substances more soluble in water by mere addition or by fusion.
stabilizer.
manufacture of methylamine, denaturing alcohol.
In organic syntheses.
Acetamide is used as a co-monomer in the production of polymeric materials such as polyvinyl acetamide, a polymeric product used as an absorbent.
It can be used for the transamidation of carbxamides in 1,4-dioxane in the absence of a catalyst.
2. Cryoscopy; organic synthesis; general
solvent; lacquers; explosives, soldering flux;
wetting agent; plasticizer
3. As a dipolar solvent, acetamide finds many uses as a solvent for
both inorganic and organic compounds. The solvency has led
to widespread uses in industry including applications in
cryoscopy, soldering, and the textile industry. The neutral and
amphoteric characteristics allow its use as an antacid in the
lacquer, explosives, and cosmetics industries. Its hygroscopic
properties make it useful as a plasticizer in coatings, fixtures,
cloth, and leather, and as a humectant for paper. It is also a raw
material in organic synthesis of methylamine and thioacetamide
and as an intermediate in preparation of medicines,
insecticides, and plastics.
General Description
Colorless crystals with a mousy odor (NTP, 1999). Low toxicity.
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
Different sources of media describe the Health Hazard of 60-35-5 differently. You can refer to the following data:
1. 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.
2. 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.
Hydration of Aliphatic Nitriles Catalyzed by an Osmium Polyhydride: Evidence for an Alternative Mechanism
Babón, Juan C.,Esteruelas, Miguel A.,López, Ana M.,O?ate, Enrique
, p. 7284 - 7296 (2021/05/29)
The hexahydride OsH6(PiPr3)2 competently catalyzes the hydration of aliphatic nitriles to amides. The main metal species under the catalytic conditions are the trihydride osmium(IV) amidate derivatives OsH3{κ2-N,O-[HNC(O)R]}(PiPr3)2, which have been isolated and fully characterized for R = iPr and tBu. The rate of hydration is proportional to the concentrations of the catalyst precursor, nitrile, and water. When these experimental findings and density functional theory calculations are combined, the mechanism of catalysis has been established. Complexes OsH3{κ2-N,O-[HNC(O)R]}(PiPr3)2 dissociate the carbonyl group of the chelate to afford κ1-N-amidate derivatives, which coordinate the nitrile. The subsequent attack of an external water molecule to both the C(sp) atom of the nitrile and the N atom of the amidate affords the amide and regenerates the κ1-N-amidate catalysts. The attack is concerted and takes place through a cyclic six-membered transition state, which involves Cnitrile···O-H···Namidate interactions. Before the attack, the free carbonyl group of the κ1-N-amidate ligand fixes the water molecule in the vicinity of the C(sp) atom of the nitrile.
A CO2-mediated base catalysis approach for the hydration of triple bonds in ionic liquids
Han, Buxing,Ke, Zhengang,Li, Ruipeng,Liu, Zhimin,Tang, Minhao,Wang, Yuepeng,Zeng, Wei,Zhang, Fengtao,Zhao, Yanfei
supporting information, p. 9870 - 9875 (2021/12/27)
Herein, we report a CO2-mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO2 (e.g., azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the anion-complexed CO2 could abstract one proton from proton resources (e.g., IL cation) and transfer it to the CN or CC bonds via a six-membered ring transition state, thus realizing their hydration. In particular, tetrabutylphosphonium 2-hydroxypyridine shows high efficiency for hydration of nitriles and CC bond-containing compounds under a CO2 atmosphere, affording a series of carbonyl compounds in excellent yields. This catalytic protocol is simple, green, and highly efficient and opens a new way to access carbonyl compounds via triple bond hydration under mild and metal-free conditions.
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.
