Method for preparing high purity mono-hydrolyzed acyl halide compound
A method for preparing a high purity (e.g. greater than 70 wt. %) mono-hydrolyzed acyl halide compound as a precipitate from solution comprising the steps of preparing a solution comprising: i) at least 80 v/v % of a hydrocarbon solvent, ii) water at a molar concentration greater than its solubility limit within the solvent but less that its solubility limit in solution, iii) a tri-hydrocarbyl phosphate compound, and iv) a polyfunctional acyl halide compound at molar ratio to both water and the tri-hydrocarbyl phosphate compound of at least 1:1.
1. A method for preparing a mono-hydrolyzed acyl halide compound as a precipitate from solution comprising the step of preparing a solution comprising:
i) at least 80 v/v % of a hydrocarbon solvent having a water solubility of less than 800 ppm,
ii) water at a molar concentration greater than its solubility limit within the solvent but less that its solubility limit in solution,
iii) a tri-hydrocarbyl phosphate compound, and
iv) a polyfunctional acyl halide compound at molar ratio to both water and the tri-hydrocarbyl phosphate compound of at least 1:1.
2. The method of claim 1 wherein the precipitate comprises at least 70 wt % of the mono-hydrolyzed acyl halide compound.
3. The method of claim 1 wherein the precipitate comprises at least 90 wt % of the mono-hydrolyzed acyl halide compound.
4. The method of claim 1 wherein at least one of the polyfunctional acyl halide compound or water are continuously added to the solution.
5. The method of claim 1 wherein both the polyfunctional acyl halide compound and water are continuously added to the solution.
6. The method of claim 1 wherein the concentration of the polyfunctional acyl halide compound is maintained in the solution at a molar ratio greater than 1:1 with water and at least 2:1 with the tri-hydrocarbyl phosphate compound.
7. The method of claim 1 wherein the concentration of water is maintained in the solution at a concentration greater than its solubility limit within the solvent but less that its solubility limit in solution.
8. The method of claim 1 wherein the solution comprises from 100 ppm to 1 weight percent of water.
9. The method of claim 1 wherein the solution comprises from 0.1 to 20 weight percent of the polyfunctional acyl halide compound.
10. The method of claim 1 wherein the polyfunctional acyl halide compound and mono-hydrolyzed acyl halide compound both have a molecule weight less than 300 Daltons.
11. The method of claim 1 wherein the polyfunctional acyl halide compound and mono-hydrolyzed acyl halide compound both comprise equal to or less than 30 carbon atoms.
12. The method of claim 1 wherein the polyfunctional acyl halide compound and mono-hydrolyzed acyl halide compound both comprise from 4 to 12 carbon atoms.
13. The method of claim 1 wherein the polyfunctional acyl halide compound comprises a carbon containing moiety selected from: an arene group substituted with a plurality of acyl halide functional groups; and the mono-hydrolyzed acyl halide compound comprises an arene group substituted with at least one acyl halide functional group and a carboxylic acid functional group.
14. The method of claim 1 wherein the tri-hydrocarbyl compound is represented by:
wherein R 1 , R 2 and R 3 are independently selected from hydrogen and hydrocarbyl groups comprising from 1 to 10 carbon atoms, with the proviso that no more than one of R 1 , R 2 and R 3 are hydrogen.
15. The method of claim 13 wherein R 1 , R 2 and R 3 are independently selected from: aliphatic and arene groups.