Method for preparing high purity mono-hydrolyzed acyl halide compound

Patent metadata

Field	Value
Publication number	US-9029600-B2
Application number	US-201214125208-A
Country	US
Kind code	B2
Filing date	Sep 14, 2012
Priority date	Sep 29, 2011
Publication date	May 12, 2015
Grant date	May 12, 2015

Abstract

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.

First claim

The invention claimed is:

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.

Assignees

• Qiu Xiaohua S
• Jons Steven D
• Koob Joseph D
• Peery Martin H
• Rosenberg Steven
• Roy Abhishek
• Tomlinson Ian A
• Dow Global Technologies Llc

Inventors

• Qiu Xiaohua S
• Jons Steven D
• Koob Joseph D
• Peery Martin H
• Rosenberg Steven
• Roy Abhishek
• Tomlinson Ian A

Classifications

• C07C53/42

  of acids containing three or more carbon atoms · CPC title

• C07C51/62 Primary

  by reactions not involving the carboxylic acid halide group · CPC title

• C07C51/58 Primary

  Preparation of carboxylic acid halides · CPC title

• C07F9/11

  with hydroxyalkyl compounds without further substituents on alkyl · CPC title