Oxygen epichlorohydrin

The absence of any polar grouping gives this material superior low temperature performance when compared to the epichlorohydrin terpolymers, but this is at the expense of oil resistance. The unsaturated nature of the main chain confers excellent resistance to oxygen, ozone and UV light. 

Oxygenated organics Acrylic acid esters, epichlorohydrin Monomers may escape from polymers... 

Propranolol, a drug that is used to lower blood pressure, is prepared from the epoxide epichlorohydrin. First, the oxygen of 1-naphthol displaces the chlorine of epichlorohydrin in an SN2 reaction. Then the epoxide ring is opened by the nucleophilic nitrogen of isopropylamine in another SN2 reaction to form propranolol. 

Epoxy resins, which are used as adhesives, are also thermoset polymers that form by cross-linking when the two components of the resin are mixed. One component is a low-molecular-mass linear polymer formed by the reaction of the conjugate base of bisphenol A with epichlorohydrin. The nucleophilic oxygens of the phenolate dianion can either displace the chlorine or open the epoxide ring of epichlorohydrin. A slight excess of epichlorohydrin is used to keep these polymer chains short and to ensure that the linear molecules have epoxide groups at their ends. 

Hydroxythiadiazoles exhibit marked acid properties (see Section 4.26.2.8) and exist essentially in the hydroxy form (68AHC(9)107). Alkylation with alkyl halides or sulfates and base in dipolar aprotic solvents usually forms ethers. In media where the oxygen atom is screened by solvation or by formation of ion pairs, mixtures of N- and O -alkylation products are formed. The reaction of 3-chloro-4-hydroxy-l,2,5-thiadiazole with epichlorohydrin catalyzed by piperidine in the absence of a solvent gave a mixture of N- and O-alkylated products in about equal amounts (72JMC651). Treatment of 3 - hydroxy-4-(A - morpholino) -... 

Application The modern Vinnolit oxychlorination process produces ethylene dichloride (EDC) by an exothermic reaction from feedstocks including ethylene, anhydrous hydrogen chloride (HCI) and oxygen. Anhydrous HCI can be used from the VCM process as well as from other processes such as isocyanates (MDI, TDI), chlorinated methanes, chlorinated ethanes, epichlorohydrin, etc. 

Chlorine-containing Polymers. Polymers containing one chlorine atom in various environments (other sustituents) were studied by XPS poly(vinyl chloride) PVC, poly(chlorotrifluoro-ethylene) PCTFE, an (ethylene-chlorotrifluoroethylene) copolymer, and poly(epichlorohydrine) PEPI, were chosen because besides carbon atoms they contain chlorine in presence of hydrogen, fluorine, and oxygen atoms. The valence band spectra of these compounds (see Figure 9) show that features can be easily and unambiguously assigned to a contribution from the chlorine molecular orbitals. 

Several patents and two papers deal with the epoxidation of allyl chloride [98, 99]. Actually, a process based on TS-1 would represent an environmentally cleaner alternative to current production of epichlorohydrin. In this regard, one study has addressed the cost of commercial hydrogen peroxide with the in situ production of the oxidant, by the use of molecular oxygen and anthrahydroquinone compounds [99]. In a mechanistic study, the kinetic data were interpreted on the basis of Eley-Rideal isotherms, with the rate of reaction being first order on TS-1 and between 0 and 1 on H2O2 and C3H5CI (Equation 18.8) [98]. 

When an unsymmetrical secondary alcohol is formed, depending on which carbon-oxygen bond is cleaved. With propylene oxide, for example, a base-catalyzed reaction favors the formation of the secondary alcohol almost exclusively, whereas, a non-catalytic or acid-catalyzed alcoholysis yields a mixture of the isomeric ethers. However, the reactions of other a-epoxides, such as 3,4-epoxy-l-butene, 3,4-epoxy-l-chloropropane (epichlorohydrin), 3,4-epoxy-l-propanol (glycidol), and styrene oxide, are more complicated with respect to which isomer is favored. ... 

The ligands shown in Table 7 are structurally closely related to those described in Section 2. The difference is, that while two linkers are still CH2 groups, the third one is an oxygen function. The synthesis of this type of ligand (138)-(145) is based on epichlorohydrine as the starting material (Equation (16)). 

Similar products are apparently obtained in the interaction of white phosphorus and oxygen with epoxides (epichlorohydrin, styrene oxide, and 1,4-bu-tylene oxide) or with phenols, polyhydric alcohols or mercaptanes using ethylacetate as solvent... 

Key Words Ethylene oxide, Propylene oxide. Epoxybutene, Market, Isoamylene oxide. Cyclohexene oxide. Styrene oxide, Norbornene oxide. Epichlorohydrin, Epoxy resins, Carbamazepine, Terpenes, Limonene, a-Pinene, Fatty acid epoxides, Allyl epoxides, Sharpless epoxidation. Turnover frequency, Space time yield. Hydrogen peroxide, Polyoxometallates, Phase-transfer reagents, Methyltrioxorhenium (MTO), Fluorinated acetone, Alkylmetaborate esters. Alumina, Iminium salts, Porphyrins, Jacobsen-Katsuki oxidation, Salen, Peroxoacetic acid, P450 BM-3, Escherichia coli, lodosylbenzene, Oxometallacycle, DFT, Lewis acid mechanism, Metalladioxolane, Mimoun complex, Sheldon complex, Michaelis-Menten, Schiff bases. Redox mechanism. Oxygen-rebound mechanism, Spiro structure. 2008 Elsevier B.V. 

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