N -vinylformamide

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Structural formula
Structural formula of N-vinylformamide
General
Surname N -vinylformamide
other names
  • N -ethenylformamide
  • VFA
Molecular formula C 3 H 5 NO
External identifiers / databases
CAS number 13162-05-5
EC number 236-102-9
ECHA InfoCard 100.032.806
PubChem 83191
Wikidata Q1959616
properties
Molar mass 71.08 g mol −1
Physical state

liquid

density

1.02 g cm −3

Melting point

−8.9 ° C

boiling point

210 ° C

Vapor pressure

40 Pa (30 ° C)

solubility

Fully miscible with water

Refractive index

1.492 (25 ° C)

safety instructions
GHS labeling of hazardous substances
05 - Corrosive 07 - Warning

danger

H and P phrases H: 302-318
P: 201-261-280-305 + 351 + 338-308 + 313
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 -Vinylformamide ( VFA ), also known as N -ethenylformamide , is an amide of formic acid .

properties

N -Vinylformamide is a clear, almost colorless liquid that can be mixed with water as required. The solubility in polar organic solvents is very good. N -Vinylformamide can be distilled in vacuo . At 13 mbar the boiling point is 84 ° C, at 5 mbar 80 ° C. The calculated boiling point at normal pressure is approx. 210 ° C. Unstabilized, it is not stable at temperatures above 40 ° C, since it tends to decompose or to self-catalyze polymerization. At −10 ° C, however, it can be stored unchanged for over a year. In aqueous solution, VFA is relatively stable in the pH range 7 to 8, while it hydrolyzes quickly in acidic (pH <4) or alkaline (pH> 8.5).

VFA is not mutagenic.

Manufacturing

N- vinylformamide was first synthesized in 1964 - more by chance. An attempt was originally made to obtain 2-formylamino-propionitrile by pyrolysis . However, the desired product reacted further with cleavage of HCN to form N- vinylformamide.

In the large-scale synthesis developed by BASF , N- vinylformamide is produced from acetaldehyde and formamide (see also figure). First, acetaldehyde ( 1 ) is reacted with hydrogen cyanide to form lactic acid nitrile ( 2 ). Formamide is condensed on this with elimination of water , so that 2-formylamino-propionitrile ( 3 ) is formed. This splits off hydrogen cyanide at elevated temperatures, so that finally N- vinylformamide ( 4 ) is formed. The hydrogen cyanide goes back into the reaction cycle.

The large-scale synthesis of N-vinylformamide

use

N- vinylformamide has been manufactured on an industrial scale since the beginning of the 21st century . It serves as a monomer for the polymerization to polyvinylformamide , which in turn is partially or completely hydrolyzed to polyvinylamine . The world's largest manufacturer of VFA is BASF in Ludwigshafen am Rhein , which processes it directly into polyvinylamine , which is primarily used in the paper industry .

Individual evidence

  1. ↑ a b c d G. Hommel, HF Bender: Handbook of dangerous goods. Springer, ISBN 3-540-20370-2 , leaflet 2481.
  2. ↑ a b Data sheet N-Vinylformamide from Sigma-Aldrich , accessed on April 12, 2011 ( PDF ).
  3. ↑ Robert K. Pinschmidt Jr., Walter L. Renz, W. Eamon Carroll, Khalil Yacoub, Jennifer Drescher, AF Nordquist, Ning Chen Air Products: N-vinylformamides - Building Block for Novel Polymer Structures . In: Journal of Macromolecular Science, Part A . tape 34 , no. 10 , 1997, pp. 1885-1905 , doi : 10.1080 / 10601329708010315 .
  4. ↑ S. Jendrzejewski, W. Steglich: Thermolysis of Oxazolin-5-ones, XI 1) N-acylimines and enamides by gas-phase pyrolysis of 4-alkyl-2-oxazolin-5-ones . In: Chemical Reports . tape 114 , no. 4 , 1981, p. 1337-1342 , doi : 10.1002 / cber.19811140412 .
  5. ↑ Entry on N-vinylformamide in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
  6. ↑ a b c d e f A. Madl: The cationically induced oligomerization of N-vinylformamide . Chemnitz 2000, DNB  962394262 , urn : nbn: de: bsz: ch1-200000482 (dissertation, TU Chemnitz).
  7. ↑ P. Kurtz, H. Disselnkötter: Enamide . In: Justus Liebig's Annals of Chemistry . tape 764 , no. 1 , 1973, p. 69-93 , doi : 10.1002 / jlac.19727640110 .
  8. ↑ Polyvinylformamide and polyvinylamine ( Memento from June 28, 2007 in the Internet Archive ). In: Nachrichten aus der Chemie 49/2001.

literature

  • W. Auhorn, F. Linhart: Polyvinylamine - A new class of polymers for paper manufacture with environmentally friendly properties. In: Das Papier 46/1992, pp. 38–45.
  • WJ Auhorn: Specialty chemicals for special papers - chemicals to achieve multifunctional properties. In: Wochenblatt für Papierfabrikation 8/1999, pp. 505-510.
  • Alexander MadlStefan SpangeNorbert Mahr: Bromine as an initiator for the oligomerization of vinylformamide (VFA) . In: Polymer Bulletin . tape 44 , no. 1 , 2000, pp. 39-46 , doi : 10.1007 / s002890050571 .
  • Torsten Meyer, Stefan Spange, Stephanie Hesse, Christian Jäger, Cornelia Bellmann: Radical Grafting Polymerization of Vinylformamide with Functionalized Silica Particles . In: Macromolecular Chemistry and Physics . tape 204 , no. 4 , 2003, p. 725-732 , doi : 10.1002 / macp.200390042 .
  • Alexander Madl, Stefan Spange: Synthesis and application of oligo (vinylamine) . In: Macromolecular Symposia . tape 161 , no. 1 , 2000, pp. 149-158 , doi : 10.1002 / 1521-3900 (200010) 161: 13.0.CO; 2-P .