N -formylmorpholine

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Structural formula
Structural formula of N-formylmorpholine
General
Surname N -formylmorpholine
other names
  • 4-formylmorpholine
  • 4-morpholine carboxaldehyde
Molecular formula C 5 H 9 NO 2
Brief description

colorless and odorless liquid

External identifiers / databases
CAS number 4394-85-8
EC number 224-518-3
ECHA InfoCard 100.022.291
PubChem 20417
Wikidata Q27275975
properties
Molar mass 115.13 g mol −1
Physical state

liquid or solid, depending on the room temperature.
Contaminated product can be liquid

density

1.15 g cm −3

Melting point

23 ° C

boiling point

244 ° C

Vapor pressure

3 Pa (30 ° C)

solubility

easily soluble in water

Refractive index

1.485 (20 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 317
P: 280-302 + 352
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

N -formylmorpholine is a chemical compound from the group of nitrogen-oxygen heterocycles and carboxamides .

Extraction and presentation

N -formylmorpholine can be obtained by reacting morpholine with carbon monoxide . Other synthetic methods are also known.

properties

N -Formylmorpholine is a flammable, hardly inflammable, colorless and odorless liquid that is easily soluble in water. Your aqueous solution has an alkaline reaction. If heated above 400 ° C, decomposition occurs.

use

N -Formylmorpholine is used for the production of adenine hydrochloride (marked with C 14 ) and terphenyldialdehyde . It is also used as an extractant .

Trivia

On February 16, 2018, around 300 kilograms of N -formylmorpholine and around 70 kilograms of methanol flowed into the Rhine from a leaky pipeline in BASF's North plant in Ludwigshafen via the cooling water system .

Individual evidence

  1. ↑ a b c d e f g h i j k l Entry on N-formylmorpholine in the GESTIS substance database of the IFA , accessed on February 19, 2018(JavaScript required) .
  2. ↑ a b Data sheet 4-Formylmorpholine, 99% from Sigma-Aldrich , accessed on February 19, 2018 ( PDF ).
  3. ↑ George A. Olah, Lena Ohannesian, Massoud Arvanaghi: Synthetic methods and reactions. 119. N-Formylmorpholine: a new and effective formylating agent for the preparation of aldehydes and dialkyl (1-formylalkyl) phosphonates from Grignard or organolithium reagents. In: The Journal of Organic Chemistry. 49, 1984, p. 3856, doi : 10.1021 / jo00194a045 .
  4. ↑ Leo Schmid: Formylation with "supercritical" CO2: Efficient Ruthenium-Catalyzed Synthesis of N-Formylmorpholine. In: Catalysis Letters. 88, p. 105, doi : 10.1023 / A: 1024009722078 .
  5. ^ Heinz-Gerhard Franck, Jürgen W. Stadelhofer: Industrial Aromatic Chemistry Raw Materials Processes Products . Springer-Verlag, 2013, ISBN 978-3-662-07875-4 , pp. 115 ( limited preview in Google Book search).
  6. ↑ Augsburger Allgemeine: Ludwigshafen: BASF: No danger from solvents that have flowed into the Rhine - celebrities, curiosities, TV - Augsburger Allgemeine , accessed on February 19, 2018.
  7. ↑ Product leak into the Rhine: Product leak into the Rhine  ( page no longer available , search in web archives )  Info: The link was automatically marked as defective. Please check the link according to the instructions and then remove this notice. , accessed February 19, 2018.@1@ 2Template: Dead Link / www.basf.com