HOME

TheInfoList



Click Here for Items Related To - dimethylacetamide
OR:
dimethylacetamide on:   [Wikipedia]   [Google]   [Amazon]

Dimethylacetamide (DMAc or DMA) is the
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...
with the
formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...
CH3C(O)N(CH3)2. This colorless, water-miscible, high-boiling liquid is commonly used as a polar
solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
in
organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
. DMA is miscible with most other solvents, although it is poorly soluble in
aliphatic In organic chemistry, hydrocarbons ( compounds composed solely of carbon and hydrogen) are divided into two classes: aromatic compounds and aliphatic compounds (; G. ''aleiphar'', fat, oil). Aliphatic compounds can be saturated, like hexane ...
hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ...
s.


Synthesis and production

DMA is prepared commercially by the reaction of
dimethylamine Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to arou ...
with acetic anhydride or
acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main componen ...
. Dehydration of the salt of dimethylamine and acetic acid also furnishes this compound: : CH3CO2H·HN(CH3)2 → H2O + CH3CON(CH3)2 Dimethylacetamide can also be produced by the reaction of
dimethylamine Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to arou ...
with methyl acetate. : The separation and purification of the product is carried out by multistage
distillation Distillation, or classical distillation, is the process of separating the components or substances from a liquid mixture by using selective boiling and condensation, usually inside an apparatus known as a still. Dry distillation is the he ...
in rectification columns. DMA is obtained with essentially quantitive (99%) yield referred to methyl acetate.


Reactions and applications

The chemical reactions of dimethylacetamide are typical of ''N'',''N''-disubstituted
amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it i ...
s.
Hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysi ...
of the acyl-N bond occurs in the presence of acids: : CH3CON(CH3)2 + H2O + HCl → CH3COOH + (CH3)2NH2+Cl− However, it is resistant to bases. For this reason DMA is a useful solvent for reactions involving strong bases such as sodium hydroxide. Dimethylacetamide is commonly used as a solvent for fibers (e.g., polyacrylonitrile, spandex) or in the
adhesive Adhesive, also known as glue, cement, mucilage, or paste, is any non-metallic substance applied to one or both surfaces of two separate items that binds them together and resists their separation. The use of adhesives offers certain advant ...
industry. It is also employed in the production of
pharmaceuticals A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy ( pharmacotherapy) is an important part of the medical field and re ...
and plasticizers as a reaction medium. A solution of lithium chloride in DMAc (LiCl/DMAc) can dissolve
cellulose Cellulose is an organic compound with the formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of β(1→4) linked D-glucose units. Cellulose is an important structural component of the primary cell wa ...
. Unlike many other cellulose solvents, LiCl/DMAc gives a molecular dispersion, i.e. a "true solution". For this reason, it is used in gel permeation chromatography to determine the
molar mass distribution The molar mass distribution (or molecular weight distribution) describes the relationship between the number of moles of each polymer species (Ni) and the molar mass (Mi) of that species. In linear polymers, the individual polymer chains rarely hav ...
of cellulose samples. Dimethylacetamide is also used as an excipient in drugs, e.g. in Vumon (
teniposide Teniposide (trade name Vumon) is a chemotherapeutic medication used in the treatment of childhood acute lymphocytic leukemia (ALL), Hodgkin's lymphoma, certain brain tumours, and other types of cancer. It is in a class of drugs known as podophyllot ...
), Busulfex ( busulfan) or Amsidine (
amsacrine Amsacrine (synonyms: m-AMSA, acridinyl anisidide) is an antineoplastic agent. It has been used in acute lymphoblastic leukemia. Mechanism Its planar fused ring system can intercalate into the DNA of tumor cells, thereby altering the major and ...
).


Toxicity

Dimethylacetamide, like most simple alkyl amides, is of low acute toxicity. Chronic exposure can cause hepatotoxicity.U.S. Department of Health and Human Services & U.S. Department of Labor (1978
Occupational Health Guideline for Dimethyl Acetamide
Now: Occupational Health Guideline for Chemical Hazards
DHHS (NIOSH) Publication Number 81-123
January 1981. The National Institute for Occupational Safety and Health (NIOSH). At high doses (400 mg/kg body mass daily), dimethylacetamide causes effects on the
central nervous system The central nervous system (CNS) is the part of the nervous system consisting primarily of the brain and spinal cord. The CNS is so named because the brain integrates the received information and coordinates and influences the activity of all p ...
(e.g. depression, hallucinations and
delusion A delusion is a false fixed belief that is not amenable to change in light of conflicting evidence. As a pathology, it is distinct from a belief based on false or incomplete information, confabulation, dogma, illusion, hallucination, or som ...
). Dimethylacetamide may be incompatible with
polycarbonate Polycarbonates (PC) are a group of thermoplastic polymers containing carbonate groups in their chemical structures. Polycarbonates used in engineering are strong, tough materials, and some grades are optically transparent. They are easily work ...
or ABS. Devices (e.g. syringes) that contain polycarbonate or ABS can dissolve when coming into contact with dimethylacetamide.


Regulation

In 2011, dimethylacetamide was identified in the EU as a Substance of very high concern (SVHC) because of its reproductive toxicity. In 2014, the European Commission has started an investigation to restrict the use of dimethylacetamide in the EU according to
REACH Reach or REACH may refer to: Companies and organizations * Reach plc, formerly Trinity Mirror, large British newspaper, magazine, and digital publisher * Reach Canada, an NGO in Canada * Reach Limited, an Asia Pacific cable network company ...
. In 2015, the CNESST (Committee on Standards, Equity, Health and Safety at Work in
Quebec Quebec ( ; )According to the Canadian government, ''Québec'' (with the acute accent) is the official name in Canadian French and ''Quebec'' (without the accent) is the province's official name in Canadian English is one of the thirte ...
) has adopted a tightened classification of dimethylacetamide:Commission des normes, de l'équité, de la santé et de la sécurité du travail (CNESST), Quebec, Canada
WHMIS 2015 classification of N,N-Dimethylacetamide


References

{{Reflist


External links


Process flowsheet of Dimethylacetamide Production from Acetic Acid and Dimethylamine


Amide solvents Acetamides