3377-92-2Relevant articles and documents
Novel synthesis routes for the preparation of low toxic vinyl ester and vinyl carbonate monomers
Hofecker, Andreas,Knaack, Patrick,Liska, Robert,Markovic, Marica,Ovsianikov, Aleksandr,Steinbauer, Patrick
supporting information, p. 3629 - 3641 (2020/10/02)
UV curing of photopolymerizable monomers, like (meth)acrylates, has been utilized for coatings for more than half a century and more recently in further developed areas such as tissue engineering. However, these monomers have major disadvantages, e.g., high irritancy and cytotoxicity, which leads to limited use in tissue engineering regarding health issues. Vinyl esters (VE) and vinyl carbonates (VC) can compete with (meth)acrylates in terms of material properties and have significantly lower toxicity, but lack in cost efficient synthesis methods. The purpose of this communication is to establish new pathways to overcome this drawback. It was shown that VEs can be synthesized either by vinyloxy trimethylsilane or by acetaldehyde in excellent yields. Moreover, a new method to synthesize vinyl chloroformate as precursor for VCs in lab scale was evolved by a catalyzed reaction of vinyloxy trimethylsilane with a phosgene solution. Finally, the cytotoxicity tests showed auspicious results.
PROCESS FOR THE PRODUCTION OF HIGHER CARBOXYLIC ACID VINYL ESTERS
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Page/Page column 40; 42-43, (2017/01/31)
This invention concerns a process for the production of vinyl esters of carboxylic acids with 3 to 20 carbon atoms, via vinylation in the presence of palladium (Pd) catalyst in combination with copper (Cu) as co-catalyst stabilized by organic salts in the presence of ethylene and air or oxygen.
Transvinylation as a First Stage of Coupling Production of Vinyl Esters and Acetic Acid or Propionic Acid Reaction Products
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Paragraph 0058-0059, (2014/12/09)
Process for coproduction of a vinyl ester of the formula R—C(O)O—CH═CH by transvinylation reaction of a carboxylic acid of the formula R—C(O)OH with a transvinylating reagent of the formula R1—C(O)O CH═CH2, characterized in that (a) the transvinylation reaction is conducted continuously at a temperature of 90 to 160° C. and at a pressure of 0.5 to 15 MPa without withdrawal of a reactant in the presence of a transition meta/catalyst containing at least one transition metal selected from the group of ruthenium, osmium, rhodium, iridium, palladium and platinum; (b) the resulting reaction mixture is separated into its constituents and the vinyl ester of the formula R—C(O)O—CH═CH2 and the carboxylic acid of the formula R1—C(O)—OH are removed; and (c) the carboxylic acid obtained after step (b) is converted to a derivative of the formula R1—C(O)—X, R1—CH2—OH or R6—C(O)—OH in which X is vinyloxy, O—CH—CH2, halogen, alkoxy of the formula OR2 in which R2 is a substituted or unsubstituted hydrocarbyl radical having 1 to 10 carbon atoms, amino of the formula NR3R4 in which R3 and R4 are each independently hydrogen or a substituted or unsubstituted hydrocarbyl radical having 1 to 10 carbon atoms, or carboxyl of the formula O—C(O)—R5 in which R5 is hydrogen or a substituted or unsubstituted hydrocarbyl radical having 1 to 10 carbon atoms, and R6 is the partly or fully halogen-substituted R1 radical.
