Process for preparing divinylarene dioxides
View Patent ↗A process for preparing a divinylarene dioxide including reacting (a) at least one divinylarene; and (b) at least one peracid oxidant compound, under conditions to form a divinylarene dioxide product; wherein the peracid oxidant compound is capable of providing an increased yield of a divinylarene dioxide product.
1. A process for preparing a divinylarene dioxide comprising reacting (a) at least one divinylarene; (b) at least one basic compound; (c) at least one oxidant; wherein the oxidant comprises a peracid oxidant capable of reacting with the divinylarene tinder reaction conditions to form a divinylarene dioxide product at a yield of greater than 50 percent.
2. The process of claim 1 , wherein the divinylarene, the basic compound, and the peracid oxidant reaction is carried out under homogeneous reaction conditions.
3. The process of claim 1 , wherein the oxidant comprises an aliphatic peracid oxidant or an aromatic peracid oxidant.
4. The process of claim 1 , wherein the reaction of the divinylarene, the basic compound, and the peracid oxidant is carried out under heterogeneous conditions sufficient to form a divinylarene dioxide product.
5. The process of claim 1 , wherein the peracid oxidant comprises performic acid, peracetic acid, m-chloroperbenzoic acid, perbenzoic acid, monoperphthalic acid, and mixtures thereof.
6. The process of claim 1 , wherein the peracid oxidant is added to the reaction mixture as a solid; or wherein the peracid compound is first mixed in a solution and then the solution subsequently added the reaction mixture.
7. A process for preparing a divinylarene dioxide comprising reacting (a) at least one divinylarene; (b) at one basic compound; (c) at least one oxidant; wherein the oxidant comprises a peracid compound capable of reacting with the divinylarene under reaction conditions to form a divinylarene dioxide product at a yield of greater than 50 percent, and wherein the peracid oxidant used in the reaction is generated in-situ.
8. The process of claim 1 , including a solvent; and wherein the solvent comprises chlorinated hydrocarbons; aromatic hydrocarbons; polar solvents; ethers; alcohols; fluorinated alcohols; or mixtures thereof.
9. The process of claim 1 , wherein the at least one divinylarene is divinylbenzene; and wherein the divinylarene dioxide formed is divinylbenzene dioxide.
10. The process of claim 1 , wherein the reaction is carried out at a temperature within the range of from about 0° C. to about 100° C.
11. The process of claim 1 , wherein the concentration of the at least one divinylarene ranges from about 1 weight percent to about 100 weight percent; and wherein the molar ratio of the oxidant compared to the divinylarene in the present invention ranges from about 1 mol/mol to about 20 mol/mol.
12. The process of claim 1 , further including the step of separating the divinylarene dioxide reaction product from residual components of the reaction mixture by a separation method; and wherein the separation method comprises chromatography, precipitation, extraction, filtration, or distillation.
13. The process of claim 1 , further including the step of purifying the divinylarene dioxide reaction product; and wherein the divinylarene dioxide reaction product is purified by distillation.
14. The process of claim 1 , wherein the basic compound is sodium carbonate, potassium carbonate, sodium-hydrogencarbonate, potassium-hydrogencarbonate, sodium phosphate, potassium phosphate or mixtures thereof.
15. The process of claim 1 , wherein the basic compound is added to the reaction mixture as a solid; or wherein the basic compound is added to the reaction mixture as an aqueous solution.
16. The process of claim 1 , wherein the molar ratio of the basic compound compared to the peracid compound ranges about 0.5 mol/mol to about 5 mol/mol.
17. The process of claim 15 , wherein the pH of aqueous phase is from about 5 to about 11.
18. A process for preparing a divinylarene dioxide comprising reacting (a) at least one divinylarene; (b) at one basic compound; (c) at least one oxidant; wherein the oxidant comprises a peracid compound capable of reacting with the divinylarene under reaction conditions to form a divinylarene dioxide product at a yield of greater than 50 percent; and (d) a phase transfer agent; wherein the phase transfer agent comprises tetraakyl, tetraaryl, or mixed alkyl-aryl ammonium hydroxides or salts; and mixtures thereof.
19. The process of claim 18 , wherein the phase transfer agent includes tetrabutylammonium hydroxide, tetrabutylammonium chloride, tetrabutylammonium acetate; tetraphenylammonium hydroxide, chloride tetraphylammonium acetate or mixtures thereof.
20. The process of claim 18 , wherein the molar ratio of the divinylarene and phase transfer agent ranges from about 0.01 mol/mol to about 5 mol/mol.
21. The process of claim 1 , wherein the basic compound is a miscible organic base; and wherein the organic base is an aliphatic amine, a heteroaromatic compound or mixtures thereof.
22. The process of 21 , wherein the organic base is pyrazole, imidazole, pyridine, triethyl amine, or mixtures thereof.