Chloro-glyceryl ethers

The chloro-glyceryl ethers described earlier can be converted into the final glyceryl ether sulfonate by a Streckerization reaction, that is, use of sodium sulfite to perform sulfonation. However, the resulting composition of the surfactant will have an increased amount of sodium chloride by-product, which is very difficult to remove from the product. Therefore, it is recommended that an additional reaction step be performed to dehalogenate the product into a glycidyl ether. 

Trichioro-giyceryi ether FIGURE 8.3 Epoxidation of chloro-glyceryl ethers to giycidyi ethers... 

The chloro-glyceryl ethers are treated with an alkali metal hydroxide solution, commonly sodium hydroxide, to epoxidize the hydroxyl group on the ether with the neighboring chlorine atom as seen in Figure 8.3. This reaction produces an undesired by-product of sodium chloride and water. In addition to epoxidizing the chloro-glyceryl ethers, another benefit of this reaction is the neutralization and destruction of the catalyst, which will prevent any further reactions from occurring. ... 

Care must be taken with this reaction to prevent the hydrolysis of the epoxide. The basic solution in the presence of water at high temperatures and extended reaction times can hydrolyze the epoxide into hydroxy glyceryl ether, effectively replacing the chlorine atoms on the chloro-glyceryl ethers. Figure 8.3, with hydroxyl groups. These hydroxyl groups are unable to be converted into sulfonates by Streckerization. 

The aqueous sulfite/bisulfite solution is reacted with the glycidyl ethers to produce the final sulfonated product. As seen in Figure 8.4, the epoxide group as well as any chlorine atoms on the higher oligomers are sulfonated. For each mole of sodium sulfite that is reacted, an equimolar amount of sodium chloride is produced. Looking at the chemistry, it is easy to surmise that the chloro-glyceryl ethers from step 1 (Section 8.2) could have been used in this reaction with only sodium sulfite, but an excess of the undesired salt by-product would have been formed. 

Spirit of glyceryl trinitrate. See Nitroglycerin Spirit of Hartshorn. See Ammonium hydroxide Spirit of nitrous ether. See Ethyl nitrite Spirit orange. See Solvent yellow 14 Spirits of salt. See Hydrochloric acid Spirits of turpentine. See Turpentine Spirits of wine. See Alcohol Spirit of trinitroglycerin. See Nitroglycerin Spirit of turpentine. See Turpentine Spiro (benzofuran-2(3H), 1 -(2) cyclohexene)-3,4 -dione, 7-chloro-2, 4,6-trimethoxy-6 -p-methyl-. See Griseofulvin Spiro [bicycio [3.1.1] heptane-2,2 -oxirane], 6,6-dimethyl-. See Epoxypinane Spiro [1,3-dioxane-5,2 (2H)-napthalene], hexahydro-2,5, 5 -trimethyl-. See Dimethyl hexahydronaphthyl dihydroxymethyl acetal Spirofior. See 3-Ethyl-2,4-dioxaspiro (5.5) undec-8-ene... 

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