Dimethylacetamide

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Dimethylacetamide
Dimethylacetamide.svg
Dimethylacetamide-3D-balls-B.png
Names
Preferred IUPAC name
N,N-Dimethylacetamide
Identifiers
3D model (JSmol)
AbbreviationsDMA, DMAC, DMAc [1]
1737614
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.389 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-826-4
MeSH dimethylacetamide
PubChem CID
RTECS number
  • AB7700000
UNII
  • InChI=1S/C4H9NO/c1-4(6)5(2)3/h1-3H3 Yes check.svgY
    Key: FXHOOIRPVKKKFG-UHFFFAOYSA-N Yes check.svgY
  • CN(C)C(C)=O
Properties
C4H9NO
Molar mass 87.122 g·mol−1
AppearanceColorless liquid
Odor Ammoniacal
Density 0.937 g/mL
Melting point −20 °C (−4 °F; 253 K)
Boiling point 165.1 °C; 329.1 °F; 438.2 K
Miscible
log P −0.253
Vapor pressure 300 Pa
UV-vis (λmax)270 nm
1.4375
Viscosity 0.945 mPa·s [2]
Thermochemistry
178.2 J/(K·mol)
−300.1 kJ/mol
−2.5835–−2.5805 MJ/mol
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H312, H319, H332, H360
P280, P308+P313
NFPA 704 (fire diamond)
2
2
0
Flash point 63 °C (145 °F; 336 K)
490 °C (914 °F; 763 K)
Explosive limits 1.8–11.5%
Lethal dose or concentration (LD, LC):
2.24 g/kg (dermal, rabbit)
4.3 g/kg (oral, rat)
4.8 g/kg (oral, rat)
4.62 g/kg (oral, mouse) [3]
2475 ppm (rat, 1  h) [3]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 10 ppm (35 mg/m3) [skin] [4]
REL (Recommended)
TWA 10 ppm (35 mg/m3) [skin] [4]
IDLH (Immediate danger)
300 ppm [4]
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

Synthesis and production

DMA is prepared commercially by the reaction of dimethylamine with acetic anhydride or acetic acid. Dehydration of the salt of dimethylamine and acetic acid also furnishes this compound: [5]

CH3CO2H·HN(CH3)2 → H2O + CH3CON(CH3)2

Dimethylacetamide can also be produced by the reaction of dimethylamine with methyl acetate. [6]

Industrial synthesis of dimethylacetamide.svg

The separation and purification of the product is carried out by multistage distillation in rectification columns. DMA is obtained with essentially quantitive (99%) yield referred to methyl acetate. [6]

Reactions and applications

The chemical reactions of dimethylacetamide are typical of N,N-disubstituted amides. Hydrolysis 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. [7]

Dimethylacetamide is commonly used as a solvent for fibers (e.g., polyacrylonitrile, spandex) or in the adhesive industry. [5] It is also employed in the production of pharmaceuticals and plasticizers as a reaction medium.

A solution of lithium chloride in DMAc (LiCl/DMAc) can dissolve cellulose. 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 of cellulose samples.

Dimethylacetamide is also used as an excipient in drugs, e.g. in Vumon (teniposide), Busulfex (busulfan) or Amsidine (amsacrine).

Toxicity

Dimethylacetamide, like most simple alkyl amides, is of low acute toxicity. Chronic exposure can cause hepatotoxicity. [8] [9] [10] [11] At high doses (400 mg/kg body mass daily), dimethylacetamide causes effects on the central nervous system (e.g. depression, hallucinations and delusion). [8] [12] [13]

Dimethylacetamide may be incompatible with polycarbonate or ABS. Devices (e.g. syringes) that contain polycarbonate or ABS can dissolve when coming into contact with dimethylacetamide. [14]

Regulation

In 2011, dimethylacetamide was identified in the EU as a Substance of very high concern (SVHC) because of its reproductive toxicity. [15] In 2014, the European Commission has started an investigation to restrict the use of dimethylacetamide in the EU according to REACH. [16]

In 2015, the CNESST (Committee on Standards, Equity, Health and Safety at Work in Quebec) has adopted a tightened classification of dimethylacetamide: [17]

DescriptionCategory GHS hazard statement
Reproductive toxicity2Suspected of damaging fertility or the unborn child (H361)
Specific target organ toxicity – repeated exposure2May cause damage to organs through prolonged or repeated exposure (H373)
Serious eye damage/eye irritation2Causes serious eye irritation (H319)
Acute toxicity – inhalation3Toxic if inhaled (H331)
Specific target organ toxicity – single exposure – narcotic effects3May cause drowsiness or dizziness (H336)
Flammable liquid4Combustible liquid (H227)

Related Research Articles

<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−
.

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

N,N-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. It consists of a tertiary amine, featuring dimethylamino group attached to a phenyl group. This oily liquid is colourless when pure, but commercial samples are often yellow. It is an important precursor to dyes such as crystal violet.

<span class="mw-page-title-main">Ethyl acetate</span> Organic compound (CH₃CO₂CH₂CH₃)

Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

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

Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish removers. Methyl acetate is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent being less toxic and less soluble in water. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or aqueous acids. Methyl acetate is not considered a VOC in the USA.

<span class="mw-page-title-main">Acetic anhydride</span> Organic compound with formula (CH₃CO)₂O

Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.

Dimethylformamide is an organic compound with the formula (CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions. Dimethylformamide is odorless, but technical-grade or degraded samples often have a fishy smell due to impurity of dimethylamine. Dimethylamine degradation impurities can be removed by sparging samples with an inert gas such as argon or by sonicating the samples under reduced pressure. As its name indicates, it is structurally related to formamide, having two methyl groups in the place of the two hydrogens. DMF is a polar (hydrophilic) aprotic solvent with a high boiling point. It facilitates reactions that follow polar mechanisms, such as SN2 reactions.

<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.

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

Amyl acetate (pentyl acetate) is an organic compound and an ester with the chemical formula CH3COO[CH2]4CH3 and the molecular weight 130.19 g/mol. It is colorless and has a scent similar to bananas and apples. The compound is the condensation product of acetic acid and 1-pentanol. However, esters formed from other pentanol isomers (amyl alcohols), or mixtures of pentanols, are often referred to as amyl acetate. The symptoms of exposure to amyl acetate in humans are dermatitis, central nervous system depression, narcosis and irritation to the eyes and nose.

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

Tributyl phosphate, known commonly as TBP, is an organophosphorus compound with the chemical formula (CH3CH2CH2CH2O)3PO. This colourless, odorless liquid finds some applications as an extractant and a plasticizer. It is an ester of phosphoric acid with n-butanol.

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 around 40%. An estimated 270,000 tons were produced in 2005.

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

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

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

n-Butyl acetate is an organic compound with the formula CH3CO2(CH2)3CH3. A colorless, flammable liquid, it is the ester derived from n-butanol and acetic acid. It is found in many types of fruit, where it imparts characteristic flavors and has a sweet smell of banana or apple. It is used as an industrial solvent

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

Propyl acetate, also known as propyl ethanoate, is an organic compound. Nearly 20,000 tons are produced annually for use as a solvent. This colorless liquid is known by its characteristic odor of pears. Due to this fact, it is commonly used in fragrances and as a flavor additive. It is formed by the esterification of acetic acid and propan-1-ol, often via Fischer–Speier esterification, with sulfuric acid as a catalyst and water produced as a byproduct.

<span class="mw-page-title-main">Propan-1-ol</span> Primary alcohol compound

Propan-1-ol is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colourless liquid and an isomer of 2-propanol. It is formed naturally in small amounts during many fermentation processes and used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.

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

Isopropyl acetate is an ester, an organic compound which is the product of esterification of acetic acid and isopropanol. It is a clear, colorless liquid with a characteristic fruity odor.

<span class="mw-page-title-main">Isoamyl acetate</span> Chemical compound with banana odor

Isoamyl acetate, also known as isopentyl acetate, is an organic compound that is the ester formed from isoamyl alcohol and acetic acid, with the molecular formula .It is a colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents. Isoamyl acetate has a strong odor which is described as similar to both banana and pear. Pure isoamyl acetate, or mixtures of isoamyl acetate, amyl acetate, and other flavors in ethanol may be referred to as banana oil or pear oil.

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

Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.

<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.

2-Ethoxyethyl acetate is an organic compound with the formula CH3CH2OCH2CH2O2CCH3. It is the ester of ethoxyethanol and acetic acid. A colorless liquid, it is partially soluble in water.

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

Acetyl hypochlorite, also known as chlorine acetate, is a chemical compound with the formula CH3COOCl. It is a photosensitive colorless liquid that is a short lived intermediate in the Hunsdiecker reaction.

References

  1. ↑ Munro, D. D.; Stoughton, R. B. (1965). "Dimethylacetamide (DMAC) and Dimethylformamide (DMFA). Effect on Percutaneous Absorption". Archives of Dermatology. 92 (5): 585–586. doi:10.1001/archderm.1965.01600170101020. PMID   5844405.
  2. ↑ Iloukhani, H., K. Khanlarzadeh. "Densities, viscosities, and refractive indices for binary and ternary mixtures of N, N-dimethylacetamide (1)+ 2-methylbutan-2-ol (2)+ ethyl acetate (3) at 298.15 K for m liquid region and at ambient pressure". Journal of Chemical & Engineering Data, 51.4 (2006): 1226–1231. doi:10.1021/je050538q.
  3. 1 2 "Dimethyl acetamide". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. 1 2 3 NIOSH Pocket Guide to Chemical Hazards. "#0218". National Institute for Occupational Safety and Health (NIOSH).
  5. 1 2 Cheung, H.; Tanke, R. S.; Torrence, G. P. "Acetic Acid". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_045.pub2.
  6. 1 2 Grafmans, Horst; Maas, Steffen; Weck, Alexander; Rütter, Heinz; Schulz, Michael; Ross, Karl-Heinz. "Method for the production of n,n-dimethylacetamide (DMAC)". Google Patents. BASF SE. Retrieved 18 July 2019.
  7. ↑ Zen, S.; Kaji, E. (1977). "Dimethyl nitrosuccinate". Organic Syntheses . 57: 60.; Collective Volume, vol. 6, p. 503
  8. 1 2 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).
  9. ↑ Baum, S. L.; Suruda, A. J. (1997). "Toxic Hepatitis from Dimethylacetamide". International Journal of Occupational and Environmental Health. 3 (1): 1–4. doi:10.1179/oeh.1997.3.1.1. PMID   9891094.
  10. ↑ Lee, C.-Y.; Jung, S.-J.; Kim, S.-A.; Park, K.-S.; Ha, B.-G. (2006). "Incidence of dimethylacetamide induced hepatic injury among new employees in a cohort of elastane fibre workers". Occupational and Environmental Medicine. 63 (10): 688–693. doi:10.1136/oem.2005.023580. PMC   2078052 . PMID   16728503.
  11. ↑ Gong, W.; Liu, X.; Zhu, B. (2016). "Dimethylacetamide-induced occupational toxic hepatitis with a short term recurrence: a rare case report". Journal of Thoracic Disease. 8 (6): E408–E411. doi:10.21037/jtd.2016.04.44. PMC   4885965 . PMID   27293868.
  12. ↑ Weiss, A. J.; Jackson, L. G.; Carabasi, R. A.; Mancall, E. L.; White, J. C. (1962). "A Phase I Study of Dimethylacetamide". Cancer Chemotherapy Reports. 16 (February 1962): 477–485. PMID   14005853.
  13. ↑ Weiss, A. J.; Mancall, E. L.; Koltes, J. A.; White, J. C.; Jackson, L. G. (1962). "Dimethylacetamide: A Hitherto Unrecognized Hallucinogenic Agent". Science. 136 (3511): 151–152. doi:10.1126/science.136.3511.151. PMID   14005854.
  14. ↑ FDA warns health care professionals not to use Treanda Injection (solution) with closed system transfer devices, adapters, and syringes containing polycarbonate or acrylonitrile-butadiene-styrene. 10 March 2015.
  15. ↑ Agreement of the Member State Committee on the Identification of N,N-Dimethylacetamide (DMAC) as a Substance of Very High Concern – Adopted on 24 November 2011.
  16. ↑ Commission Regulation (EU) No 895/2014, Official Journal of the European Union, 19.08.2014.
  17. ↑ 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.
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