By F.E. Bailey
A complete therapy of a giant relatives of polymers important in a variety of purposes in such fields as automobile, pharmaceutical, beauty, metal-working, mining, commercial coating, fabric, development, and residential furniture. Summarizes the chemistry and mechanisms; presents uncomplicated prepa
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Extra info for Alkylene Oxides and Their Polymers
W. H. Millet, Iron Age Engr. 25 (8):51 (1948). Bibliography G. O. , Glycols, Reinhold Publishing Company, ACS Monograph, New York, 1952. A. S. Malinovski, Epoxides and Their Derivatives, translated from Russian, 1965 Israel Program for Scientific Translation, Jerusalem, 1965. Page 35 4— Polymerization of 1,2-Epoxides I— Introduction The 1,2-epoxides, or vicinal epoxides, include the alkylene oxides, the simplest of which is ethylene oxide. The first reported polymerization of ethylene oxide was by Wurtz in 1863 (1), who described the reaction of ethylene oxide heated in a sealed tube with water and, later, with alkali and with zinc chloride catalysts.
First, propylene is chlorinated to form allyl chloride, which is then reacted with hypochlorous acid to give glycerol dichlorohydrin. Caustic treatment of glycerol dichlorohydrin then produces epichlorohydrin. In Japan, a process has been used in which allyl chloride is epoxidized with hydrogen peroxide to give epichlorohydrin directly. C— Uses At one time, the major use of epichlorohydrin was as an intermediate in the manufacture of glycerol. Now, 55 percent of the production is consumed in the making of epoxy resins.
021 111° While all three ring systems are opened by cationic or acid-initiated mechanisms, only the 1,2-epoxide oxirane can be polymerized by both anionic and cationic initiation. Notice that only 1,2-epoxyethane, ethylene oxide, is derived by epoxidation of an alkene and, thus, is the only alkylene oxide in this series. Ethylene oxide has the molecular structure shown below. This epoxide ring has an estimated strain energy of 14 kcal/mol (13), and this is the high driving force for ring-opening polymerization to poly(ethylene oxide).
Alkylene Oxides and Their Polymers by F.E. Bailey