N-Vinylformamide — Syntheses and Chemistry of a Multifunctional Monomer

Abstract

N‐Vinylformamide (VFA), the simplest member of the enamide group, is the key compound in the synthesis of linear cationic polymers with primary amino groups. In recent decades VFA has been the object of intensive research activity in industry and in universities with the aim of developing an economic method of synthesis. The various principles underlying the synthesis are described and the possibilities for their industrial realisation are discussed. From the large number of methods two variants have now been established as industrial production procedures at BASF and Mitsubishi Kasei Corp. (MKC). VFA is now available in tonne quantities in high purity. An overview of the versatile reaction possibilities of this multifunctional monomer and an extensive list of references are also given. The radical polymerisation to polyvinylformamides and their further reaction to polyvinylamines are not covered in this review.

N-vinylformamide - a new environmentally friendly water-soluble monomer

“…Ale by³ to krok we w³aoeciwym kierunku zmierzaj¹cym do prób hydrolizy polimerów innych enamidów otrzymywanych na drodze winylowania acetylenu, np. N,N-winylometyloacetamidu [8]:…”

“…Koncern BASF swoj¹ technologiê opar³ na nitrylu kwasu mlekowego stanowi¹cym addukt cyjanowodoru do aldehydu octowego [8]. Dzia³aj¹c formamidem na nitryl kwasu mlekowego ju¿ w 1969 r. otrzymano tam N-winyloformamid:…”

“…AAM jest cia³em sta³ym, NVF stanowi natomiast w normalnych warunkach ciecz i -co warto podkreoeliae -nietoksyczn¹. Wybrane inne w³aoeciwooeci charaktery-zuj¹ce NVF [8] to: -masa molowa: 71 g/mol;…”

Polyvinylamine - a base for new routes in hydrophilic polymers development

“…Większe na dzieje stw arzały reakcje polegające na hydrolizie poli(N--winyloamidów) lub innych polimerów, w których gru pa winylowa jest bezpośrednio zw iązana z atomem azo tu. Za przykład może służyć hydroliza poli(N-winyloimidu kwasu bursztynowego) [4] poli(tetrabutyro-N-winylokarbam inianu) [5] oraz poli(N-winyloacetamidu) [6,7], Stosunkowo najlepsze wyniki osiągano w ostat nim przypadku, aczkolwiek i one nie były w pełni zado walające. Hydroliza kw asow a poli(N-winyloacetamidu) wym aga bowiem stosow ania dosyć drastycznych w a runków, mianowicie użycia 1 M HC1 w temp.…”

Alginic acid‐g‐poly(N‐vinylformamide) graft copolymer: Synthesis, characerization, swelling, and flocculation property

“…Grafting of vinyl monomer, the method, on to polymeric backbone of alginic acid not only improves the drawbacks but also increases its properties such as swelling and flocculation because the additional properties of vinyl monomer are superimposed. N ‐vinylformamide (NVF), a key compound in synthesis of cationic polymers,23 is hydrophilic and low toxic in nature. It has potential interests in a number of areas such as petroleum recovery from oil wells, water treatment, and effective drag reducing agent and the major applications such as dry and wet strength for paper making 24–29.…”