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Synthesis on N-vinyl formamide

a technology of n-vinylformamide and synthesis method, which is applied in the preparation of carboxylic acid amides, organic chemistry, chemistry apparatus and processes, etc., can solve the problems of nvf material synthesized by this method, exhibited lower than desired purity, and most likely restricted process

Inactive Publication Date: 2006-02-02
UNIVERSITY OF PITTSBURGH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This method increases the purity and molecular weight of N-vinylformamide, reduces the need for stringent conditions, and avoids the hydrolysis issues associated with traditional methods, resulting in a more stable and higher-quality product.

Problems solved by technology

As this highly toxic chemical cannot be transported, the process is most likely restricted to Ludwigshafen.
It has been reported that the NVF material synthesized by this method, exhibited lower than desired purity.
Obviously the presence of water during this reaction creates problems.

Method used

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  • Synthesis on N-vinyl formamide
  • Synthesis on N-vinyl formamide
  • Synthesis on N-vinyl formamide

Examples

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experimental examples

[0043] In the studies of the present invention, some of the quantities were varied between experiments but the quantities set forth in the examples below are representative values and scales. No attempt was made to optimize any of the reactions studied.

[0044] (1) One-Pot Reaction of acetaldehyde, formamide and acetic anhydride

[0045] i) No solvent: Acetaldehyde [21 ml; 0.377 mol], formamide [5 ml; 0.126 mol; containing 0.5 mol % K2CO3] and acetic anhydride [6 ml; 0.062 mol] were added to a flask and stirred at approximately 10° C. for 2 h. The reaction was allowed to warm to room temperature over 1 h and then heated to 70° C. IR monitoring was done throughout, demonstrating disappearance of the anhydride peaks and indicating the synthesis of the HEF adduct.

[0046] ii) With solvent: The same method as i) was followed but in addition, 40 ml of isooctane was added at the start of the reaction. Two layers were present throughout the reaction. IR monitoring was done throughout, demonstr...

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Abstract

A process to produce N-vinylformamide includes the steps of: reacting hydroxyethyl formamide with a reactant including at least one cyclic anhydride group to form an ester, and dissociating (or cracking) the ester to synthesize N-vinylformamide and a compound including at least one diacid group. The ester can be dissociated using heat. The reactant including at least one cyclic anhydride group can, for example, be succinic anhydride, maleic anhydride, phthalic anhydride, a polymer including at least one cyclic anhydride group, or a solid support to which at least one cyclic anhydride group is covalently tethered. Preferably, the cyclic anhydride is regenerated from the diacid formed in the synthesis of the ester by heating the diacid to dehydrate the diacid. The temperature required to dehydrate diacid groups is preferably higher than the temperature use to dissociate the ester.

Description

CROSS-REFERENCE TO RELATED APPLICATION [0001] The present application claims benefit of U.S. Provisional Patent Application Ser. No. 60 / 407,077, filed Aug. 30, 2003, the disclosure of which is incorporate herein by reference.BACKGROUND OF THE INVENTION [0002] The present invention relates to the synthesis of N-vinylformamide, and particularly, to the synthesis of N-vinylformamide using cyclic anhydride reagents. [0003] N-vinylformamide (NVF) is a monomer with potentially useful properties in that it free-radically polymerizes to produce water-soluble poly(N-vinylformamide) (PNVF) and also undergoes controlled radical polymerization using RAFT methodology. Badesso, R. J.; Nordquist, A. F.; Pinschmidt, Jr. R. K.; and Sagl, D. J. “Hydrophilic polymers: performance with Environmental Acceptance”, Glass, E.; Ed.; America Chemical Society, Washington, D.C., 1995, p 489. PNVF is probably the most practical precursor for preparation of poly(vinylamine). Because vinyl amine is unstable and h...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07C231/12C07B61/00C07C233/03
CPCC07C233/03C07C231/12
Inventor BECKMAN, ERIC J.CHAPMAN, TONY M.FAVERO, CEDRICK GILBERTCAPELLI, CHRISTOPHER C.SWIFT, HAROLD E.
Owner UNIVERSITY OF PITTSBURGH