Dimethylformamide

  • N, N- Dimethylmethanamid
  • N, N -dimethylformamide
  • Ameisensäuredimethylamid
  • DMF

Colorless to yellowish liquid with a faint amine-like odor

Liquid

0.95 g · cm -3 ( 20 ° C)

-61 ° C

153 ° C

3,77 hPa ( 20 ° C)

Miscible with water and many organic solvents

3.82 (8 ) D ( 1.3 × 10-29 C · m)

1.4305 (20 ° C)

Risk

15 mg · m-3

-239.3 KJ / mol

Template: Infobox chemical / molecular formula search available

Dimethylformamide (DMF), more precisely N, N -dimethylformamide is an amide of formic acid. DMF is used as polar organic solvent.

Production

The large scale production of DMF is carried out in two different ways, according to a one-step and a two-stage process. In the one-step synthesis of dimethylamine is reacted with carbon monoxide at elevated temperature and pressure directly to DMF. The reaction is carried out in the liquid phase with the aid of a catalyst ( sodium methylate )

In two-step synthesis, the conversion of dimethylamine is carried out with formic acid methyl ester, is produced as a by- product methanol:

Both reactions proceeded with high yields without the formation of significant by-products. Purification of the product in both cases by multistage distillation.

Properties

DMF is a colorless to yellowish, semi-volatile liquid that mixes with water and many organic solvents. The amide decomposes under light and heat exposure to dimethylamine and formaldehyde.

Use

  • DMF is used as solvent for a variety of solid, liquid or gaseous substances, for polymers such as polyacrylonitrile, PVC, polyamides, polyurethanes, epoxy resins, as well as cellulose and derivatives thereof.
  • DMF is used as catalyst in the preparation of acid chlorides from carboxylic acids and oxalyl chloride.
  • DMF is in the laboratory, since polar aprotic, often used for reactions with polar transition states as solvent. In nucleophilic substitutions may be compared to eg Methanol drastic speed increases are recorded.
  • DMF is used in the chemical art as an extraction agent for the separation of benzene, acetylene, 1,3- butadiene.
  • DMF is an additive to fuel, it serves as a catalyst for the combustion
  • DMF is an intermediate in the synthesis of acetals, aldehydes, carboxylic esters and nitriles
  • From DMF and phosphorus oxychloride can be the Vilsmeier -Haack reagent which is used for the formylation of aromatic compounds and the chlorination of carboxylic acids produced.

Safety

After both acute and after chronic exposure results in hepatocellular injury. Histologically, microvesicular fatty change ( fatty liver ) and changes of the liver tissue show no pronounced inflammation.

The material is in Appendix 6 to number 30 of Annex XVII of the REACH Regulation (EC ) No 1907/2006 listed as toxic to reproduction category 2.

CAS registry number Vapor pressure Electric dipole moment Debye Dangerous Substances Directive (67/548/EEC) 1,3-Butadiene Formylation reaction CRC Handbook of Chemistry and Physics Integrated Authority File
55630
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