Method for the dehydration of lactate salt to acrylic acid or acrylic salt

Patent metadata

Field	Value
Publication number	US-9828325-B2
Application number	US-201615067210-A
Country	US
Kind code	B2
Filing date	Mar 11, 2016
Priority date	Mar 13, 2015
Publication date	Nov 28, 2017
Grant date	Nov 28, 2017

Abstract

Methods for catalytically dehydrating lactate salt to acrylic acid, acrylate salt, or mixtures thereof with high yield and selectivity and without significant conversion to undesired side products, such as, acetaldehyde, propionic acid, and acetic acid, are provided. The catalysts include acid-base bifunctional catalysts.

First claim

What is claimed is:

1. A method of making acrylic acid, metal acrylate, or mixtures thereof comprising dehydrating a metal lactate by contacting a stream comprising said metal lactate with a KH 2 PO 4 catalyst comprising an acidic site and a basic site, and wherein said acidic site is a Brønsted acid with a pK a of about 4 to about 7, wherein the stream comprises a diluent selected from the group consisting of acetone, C3 to C8 linear and branched alcohols, C5 to C8 linear and branched alkanes, ethyl acetate, non-volatile ethers (including diphenyl ether), and mixtures thereof.

2. The method of claim 1 , wherein said pK a is about 4.5 to about 6.2.

3. The method of claim 2 , wherein said pK a is about 5.3.

4. The method of claim 1 , wherein said catalyst is generated from a polyphosphate by hydrolysis.

5. The method of claim 1 , wherein said catalyst includes an inert support that is constructed of a material selected from the group consisting of silicates, aluminates, zirconates, carbons, metal oxides, and mixtures thereof.

6. The method of claim 1 , wherein the metal in said metal lactate is selected from the group consisting of lithium, sodium, potassium, cesium, magnesium, calcium, strontium, and barium.

7. The method of claim 1 , wherein said stream contacts said catalyst at a temperature less than about 700° C.

8. The method of claim 7 , wherein said temperature is about 250° C. to about 450° C.

9. The method of claim 1 , wherein said contacting of said stream with said catalyst is performed with a residence time of about 0.1 s to about 1 day.

10. The method of claim 9 , wherein said residence time is about 1 s to about 1 h.

11. The method of claim 1 , wherein said stream contacts said catalyst at a pressure of about 5 bar to about 100 bar.

12. The method of claim 11 , wherein said pressure is less than about 25 bar.

13. The method of claim 1 , wherein said method has a selectivity for acrylic acid, metal acrylate, and mixtures thereof of at least about 80 mol %.

14. The method of claim 1 , wherein said method has a selectivity for propionic acid of less than about 1 mol %.

15. The method of claim 1 , wherein said method has a conversion of metal lactate of at least about 80 mol %.

16. A method of making acrylic acid, sodium acrylate, or mixtures thereof comprising contacting:
a. a stream comprising:
i. sodium lactate, and
ii. a solvent, with

b. a KH 2 PO 4 catalyst comprising an acidic site and a basic site, wherein said acidic site is a Brønsted acid with a pK a of about 4.5 to about 6.2, and wherein, said contacting of said stream with said acid-base bifunctional catalyst is performed at a temperature about 250° C. to about 450° C., and at a residence time less than about 1 day, whereby acrylic acid, sodium acrylate, or mixtures thereof are produced as a result of said stream contacting said acid-base bifunctional catalyst.

17. The method of claim 16 , wherein said solvent comprises water.

Assignees

• Procter & Gamble

Inventors

• Collias Dimitris Ioannis
• Velasquez Juan Esteban
• Godlewski Jane Ellen
• Hayes Jeffrey Charles
• Laidig William David

Classifications

• C07C57/04

  Acrylic acid; Methacrylic acid · CPC title

• C07C51/377 Primary

  by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups {(C07C51/36 - C07C51/373 take precedence)} · CPC title

• C07C51/41

  Preparation of salts of carboxylic acids ({C07C51/093 - C07C51/34 take precedence} preparation of soap C11D) · CPC title