Novel reaction between cyclic formal and ethylene oxide

Abstract

Novel reactions between trioxane and ethylene oxide were discovered, and three novel cyclic formals were isolated and identified. These novel cyclic compounds clarified the initiation mechanism of the copolymerization of trioxane and ethylene oxide. This type of reaction was not limited to the reaction between trioxane and ethylene oxide but was also generalized to the reaction between the cyclic formal and ethylene oxide. Although an NMR method for analyzing the ethylene oxide sequences of the acetal copolymer from trioxane and ethylene oxide has not yet been established, the three newly found novel cyclic compounds, composed of 1 mol of ethylene oxide and 1 mol of trioxane, 2 mol of ethylene oxide and 1 mol of trioxane, and 3 mol of ethylene oxide and 1 mol of trioxane, were useful for analyzing the ethylene oxide sequences. These compounds gave only one consecutive oxyethylene unit, two consecutive oxyethylene units, and three consecutive oxyethylene units in three consecutive oxymethylene units, respectively, and gave different 1H NMR spectra for each oxyethylene unit. Considering these data, we synthesized three polymeric model compounds that had one consecutive oxyethylene sequence, two consecutive oxyethylene sequences, and three consecutive oxyethylene sequences in an oxymethylene main chain. By a linear combination of the 1H NMR spectrum of each oxyethylene unit of the three polymeric model compounds, we succeeded in determining the ethylene oxide sequences by the 1H NMR method for the copolymer from trioxane and ethylene oxide. © 2003 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 520–533, 2004

Synthesis and crystallization behavior of acetal copolymer/silica nanocomposite by in situ cationic ring‐opening copolymerization of trioxane and 1,3‐dioxolane

“…Acetal copolymer resin is typically prepared by the cationic ring‐opening copolymerization of trioxane and a cyclic ether, such as ethylene oxide2–9 or 1,3‐dioxolane 10–13. The copolymerization can be initiated by Lewis acid such as BF 3 · O(Et) 2 , TiCl 4 14 and CH 3 CO ClO 4 15 as well as MoO 2 (C 5 H 7 O 2 ) 2 11.…”

Siloxane Coordination Revisited: Si−O Bond Character, Reactivity and Magnificent Molecular Shapes

“…Hence, an unsupported bite angle of the crown‐type macrocycle reduces the cation binding ability significantly. The experimental findings are supported by the fact that a series of ring contracted and sila‐crown ethers bearing several −CH 2 −CH 2 −O− as well as one‐ or two −SiR 2 −O− units have been described in literature, [146−154] but, no coordination compounds have been isolated and crystallographically characterized to date.…”

An Oligomer with Terminal Unsaturated Double Bonds Based on Epidian 5 and Ethylacrylic Acid

“…Like many other synthetic polymers, it is produced by different formulas. Another method is a copolymerization of 1,3,5-trioxane with cyclic ethers or acetals as copolymer synthesis with 1,3dioxolane 3 or ethylene oxide, 4 preferably with εcaprolactone. To obtain the reactions catalyzed by clay minerals, montmorillonite was used as a catalyst for the cationic polymerization of several vinyl and heterocyclic monomers.…”