In-situ method for preparing hydrolyzed acyl halide compound
View Patent ↗An in-situ method for preparing a hydrolyzed, acyl halide-containing compound by combining a reactant including a plurality of acyl halide functional groups containing reactant, a tri-hydrocarbyl phosphate compound and water within a hydrocarbon or halogenated hydrocarbon solvent.
1. A method for preparing a reaction product comprising at least one acyl halide functional group and a carboxylic acid functional group in a solution comprising a hydrocarbon or halogenated hydrocarbon solvent having a water solubility of less than 800 ppm;
wherein the reaction product has a solubility limit of less than 1 weight percent in the solvent and is produced to a molar concentration greater than its solubility limit within the solvent while remaining soluble in solution, and
wherein the solution comprises at least 80 v/v % solvent in combination with:
i) water at a molar concentration greater than its solubility limit within the solvent but less that its solubility limit with the solution,
ii) a reactant comprising a plurality of acyl halide functional groups at a molar concentration less than its solubility limit within the solvent and at a molar ratio with water from 1:2 to 1000:1, and
iii) a tri-hydrocarbyl phosphate compound at a molar ratio with the reactant from 100:1 to 1:1000 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.
2. The method of claim 1 wherein the reactant and reaction product both have a molecule weight less than 700 amu (Daltons).
3. The method of claim 1 wherein the reactant and reaction product both have a molecule weight less than 300 amu (Daltons).
4. The method of claim 1 wherein the reactant and reaction product both comprise equal to or less than 30 carbon atoms.
5. The method of claim 1 wherein the reactant and reaction product both comprise from 4 to 12 carbon atoms.
6. The method of claim 1 wherein the reactant comprises a carbon containing moiety selected from: an aliphatic or arene group substituted with a plurality of acyl halide functional groups; and the reaction product comprises an aliphatic or arene group substituted with at least one acyl halide functional group and a carboxylic acid functional group.
7. The method of claim 1 wherein the reaction product comprises an aliphatic or arene group substituted with at least one acyl halide functional group and single carboxylic acid functional group.
8. The method of claim 1 wherein the solution comprises:
i) water at a concentration of less than 1 wt. %,
ii) the reactant at a concentration of less than 10 wt. % and
iii) the tri-hydrocarbyl phosphate compound at a concentration of less than 10 wt. %.
9. The method of claim 1 wherein the solution comprises:
i) water at a concentration of less than 0.5 wt. %,
ii) the reactant at a concentration of less than 5 wt. %, and
iii) the tri-hydrocarbyl phosphate compound at a concentration of less than 5 wt. %.
10. The method of claim 1 wherein the solution comprises the reactant at a molar ratio with water from 1:2 to 100:1.
11. The method of claim 1 wherein the solution comprises the tri-hydrocarbyl phosphate compound at a molar ratio with the reactant of 10:1 to 1:100.
12. The method of claim 1 wherein the hydrocarbon solvent has a water solubility of less than 150 ppm.
13. The method of claim 1 wherein R 1 , R 2 and R 3 are independently selected from: aliphatic and arene groups.
14. The method of claim 1 wherein R 1 , R 2 and R 3 are independently selected from alkyl groups.