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The addition of chlorohydrin

Time:2015/11/25 8:26:37

Contact sensitivity to 1-(4-(chlorohydrin)phenyl)-chlorohydrin in a polymer chemist


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An exploratory study of the addition reactions of ethyleneglycol, chlorohydrin and 1,3-dichloro-2-propanol to 1-dodecene


sec-Dodecyl ethers of ethyleneglycol, chlorohydrin, and 1,3-dichloro-2-propanol have been prepared by reacting 1-dodecene with the corresponding substituted alcohol in the presence of BF3 as a catalyst.

The addition of ethyleneglycol to 1-dodecene proceeds best in the presence of a reaction solvent (e.g., nitromethane), which suppresses side reactions. The resulting ethers consist almost exclusively of the mono-sec-dodecyl derivatives. The maximum yield was about 50 mol% on dodecene intake and 75%m on converted ethyleneglycol.

The addition of chlorohydrin and 1,3-dichloro-2-propanol to dodecene can easily be conducted without a reaction solvent; yields are 77 and 67 mol% respectively on 1-dodecene intake. A reaction scheme for the addition of ethyleneglycol to 1-dodecene is proposed.