Formamide

• Methanamide
• Formamide

Colorless to yellowish odorless liquid

Liquid

1.13 g · cm -3

2 ° C

210 ° C.

3 Pa ( 20 ° C)

Completely miscible with water

1.4472 (20 ° C)

Risk

• 5580 mg · kg -1 ( LD50, rat, oral)
• 17,000 mg · kg -1 ( LD50, Rabbit, transdermal)

-254.0 KJ / mol

Template: Infobox chemical / molecular formula search available

Formamide is the amide of formic acid and the simple carboxylic acid amide.

Production

Industrially, formamide is produced by reacting carbon monoxide with ammonia. This will react first carbon monoxide with methanol to methyl formate. This is then reacted with ammonia, the methanol released is returned to the first reaction stage.

Formamide may apply in small quantities in the production of amphetamine.

Properties

Physical Properties

At room temperature the substance is present as a colorless and odorless liquid. It is hygroscopic and acts as a solvent and a reducing agent.

Chemical Properties

Formamide is unstable at temperatures above 185 ° C. At 185 ° C it splits purely thermal ( without catalysts) into carbon monoxide, carbon dioxide and ammonia, without cyanide is detected. At 220 ° C, the formation of ammonia is enhanced, while also forming hydrogen cyanide. With increasing temperature, the formation of ammonium carbonate, ammonium bicarbonate and ammonium carbamate increases, the latter being particularly easily formed from anhydrous ammonia with carbon dioxide. Prolonged thermal loading to a black, insoluble solid which is identical with polymeric cyanide and could be isolated from the purine forms. This polymer (residue) is from 360 ° C also hydrocyanic acid and isocyanic acid. In addition Isocyanuric formed from formamide by thermal stress.

For the production of hydrocyanic acid by elimination of water from formamide catalysts are used which accelerate the desired reaction, while the thermal cracking, which leads to undesired products is displacing. Metal oxides are suitable for this purpose, such as stainless steel.

Occurrence

Formamide is the simplest amide and ubiquitous in the universe. It was * and generally detected in the comet Hale- Bopp and Hyakutake and the galactic center of Sagittarius A in the interstellar medium.

Use

Formamide is used primarily by reaction with sulfuric acid for the industrial synthesis of formic acid and ammonium sulfate. Furthermore, it is processed in the vacuum formamide synthesis by pyrolysis of hydrogen cyanide. It is also used as an intermediate for the production of drugs, and fungicides, such as theophylline and theobromine, or as catalyst in the carbonylation reaction.

Formamide is a commonly used solvent, such as for paints, certain polymers and stain and ink markers.

The most important producer of formamide is BASF with a production capacity of 100,000 tons per year (as of 1998), the majority of formamide produced is processed directly at the place of manufacture.