After ingestion or inhalation, epichlorohydrin is rapidly absorbed into the body through the skin. Epichlorohydrin itself is a reactive epoxide that is metabolized by conjugation to glutathione and hydration by epoxide hydrolases. The same hemoglobin adducts have been detected in epichlorohydrin humans and rats. Epichlorohydrin is widely distributed throughout the body. In rodents, the highest tissue concentrations occurred in the nose after inhalation and in the stomach after ingestion. In rats, regardless of the route of exposure, most of the absorbed epichlorohydrin is rapidly metabolized, partly excreted via the lungs as carbon dioxide and partly excreted in the urine as water-soluble compounds.
Epichlorohydrin has been shown to be a general sidearm precursor for several lariat ether compounds <1992CSR39>. It has recently been used to form macrocycles through the reaction of oxirane fragments (see Figure 19). Thus, epichlorohydrin is treated with BF3 Et2O to give oligomeric dichlorides. This in turn is treated with triethanolamine to form a 13-crown-4 derivative containing a single nitrogen. Macrocycles are included in the network used to complex metal ions such as Ag+ and Au3+. When 1-chloro-2,3-epithiopropane replaces epichlorohydrin in the initial step, a macrocycle containing O, S, and N is formed. The selective incorporation of oxygen- and sulfur-containing resins was analyzed in the presence of other metals such as Pb2+, Cu2+ and Zn2+ <1997MI931>.
Epichlorohydrin (ECH) is another versatile chemical intermediate used in a wide variety of applications including epoxy resins, textiles, paper products, inks, dyes, automotive and aircraft parts, biocides, personal care products and ion exchange resins . Historically, ECH has been produced through a three-step process, starting with the chlorination of propylene to produce allyl chloride [Figure 42(a)]. The main by-products of the first reaction are cis and trans 1,3-dichloropropene and 1,2-dichloropropane. The following chlorohydrination of allyl chlorides yields a mixture of dichlorohydrins (also known as glycerol dichlorohydrins) [Figure 42(b)]. 1,2,3-Trichloropropane is a by-product of this reaction. In the third step, ECH is produced by alkaline dehydrochlorination of dichloropropanol isomers [Figure 42(c)]. The traditional manufacture of epichlorohydrin is a corrosive process that causes significant downtime.
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