Method of making acrylic acid from hydroxypropionic acid

Patent metadata

Field	Value
Publication number	US-9890102-B1
Application number	US-201615342428-A
Country	US
Kind code	B1
Filing date	Nov 3, 2016
Priority date	Nov 3, 2016
Publication date	Feb 13, 2018
Grant date	Feb 13, 2018

Abstract

Methods for making acrylic acid, acrylic acid derivatives, or mixtures thereof by contacting a stream containing hydroxypropionic acid, hydroxypropionic acid derivatives, or mixtures thereof with either an active catalyst containing an amorphous and partially-dehydrated phosphate salt or a precursor catalyst containing a crystalline phosphate salt in a reactor with a low corrosion rate are provided.

First claim

What is claimed is:

1. A method of making acrylic acid, acrylic acid derivatives, or mixtures thereof comprising contacting a gas feed stream comprising water vapor and hydroxypropionic acid, hydroxypropionic acid derivatives, or mixtures thereof with a catalyst in a single-layer reactor at a temperature, a water partial pressure, a Gas Hourly Space Velocity (GHSV), and a Weight Hourly Space Velocity (WHSV) to dehydrate said hydroxypropionic acid, hydroxypropionic acid derivatives, or mixtures thereof, resulting in the production of acrylic acid, acrylic acid derivatives, or mixtures thereof; wherein said catalyst comprises a phosphate salt comprising a cation and an anion represented by the empirical formula:
[H 2(1-x) PO (4-x) ] −

wherein x is any real number greater than or equal to 0 and less than or equal to 1; wherein said water partial pressure is equal to or greater than about 0.4 bar; wherein said single-layer reactor comprises a wall, an outer surface, and an inner surface; wherein said wall is made from a wall material, has a wall thickness, and extends from said outer surface to said inner surface; wherein said wall material comprises aluminum in an amount between about 1 wt % and about 50 wt %; wherein said inner surface is in contact with said catalyst; and wherein said single-layer reactor has a corrosion rate lower than about 1.3 millimeters per year (mm/y) during said dehydration.

2. The method of claim 1 ; wherein said phosphate salt is crystalline; wherein said x is 0 or 1; and wherein said cation is a monovalent cation selected from the group consisting of K + , Cs + , and mixtures thereof.

3. The method of claim 1 ; wherein said phosphate salt is amorphous and partially-dehydrated; wherein said x is any real number greater than 0 and less than 1; and wherein said cation is a monovalent cation selected from the group consisting of K + , Cs + , and mixtures thereof.

4. The method of claim 1 ; wherein said amount of said aluminum is between about 3 wt % and about 5 wt %.

5. The method of claim 1 ; wherein said wall material further comprises nickel in an amount between about 50 wt % and about 75 wt %, chromium in an amount between about 15 wt % and about 20 wt %, and iron in an amount between about 3 wt % and about 30 wt %.

6. The method of claim 1 ; wherein said wall material further comprises iron in an amount of about 70 wt % and chromium in an amount of about 22 wt %.

7. The method of claim 1 ; wherein said inner surface is subjected to oxidation and forms an oxide-based surface passivating layer comprising alumina.

8. The method of claim 7 ; wherein said oxidation occurs during said dehydration.

9. The method of claim 7 ; wherein said oxidation occurs before said dehydration.

10. The method of claim 1 ; wherein said corrosion rate is lower than 0.13 mm/y during said dehydration.

11. The method of claim 1 ; wherein said hydroxypropionic acid is lactic acid; wherein said gas feed stream comprises a diluent; wherein said diluent consists essentially of nitrogen; wherein said temperature is between about 300° C. and about 450° C.; wherein said water partial pressure is equal to or greater than 0.8 bar; and wherein said GHSV is between about 2,300 h −1 and about 3,600 h −1 , and said WHSV is between about 0.2 h −1 and about 2 h −1 .

12. The method of claim 1 ; wherein said acrylic acid, acrylic acid derivatives, or mixtures thereof are produced with a yield of at least about 80 mol % and with a selectivity of at least about 80 mol %.

13. The method of claim 1 ; wherein propionic acid is produced as an impurity along with said acrylic acid, acrylic acid derivatives, or mixtures thereof; and wherein the selectivity of said propionic acid is less than about 1 mol %.

14. The method of claim 1 ; wherein said phosphate salt is crystalline; wherein said x is 1; wherein said cation is K + ; wherein said wall material further comprises nickel in an amount between about 50 wt % and about 75 wt %, chromium in an amount between about 15 wt % and about 20 wt %, and iron in an amount between about 3 wt % and about 30%; wherein said amount of said aluminum is between about 3 wt % and about 5 wt %; wherein said hydroxypropionic acid is lactic acid; wherein said temperature is about 375° C. and said water partial pressure is about 13 bar; wherein said GHSV is about 2,300 h −1 and said WHSV is between about 0.3 h −1 and about 0.4 h −1 ; wherein said acrylic acid, acrylic acid derivatives, or mixtures thereof are produced with a yield of at least about 80% and with a selectivity of at least about 80% over a TOS of about 72 h; wherein propionic acid is produced as an impurity along with said acrylic acid, acrylic acid derivatives, or mixtures thereof; and wherein the selectivity of said propionic acid is less than about 1 mol % over said TOS of about 72 h.

15. The method of claim 1 ; wherein said phosphate salt is crystalline; wherein said x is 1; wherein said cation is K + ; wherein said wall material further comprises nickel in an amount of about 60 wt %, chromium in an amount between about 20 wt % and about 30 wt %, and iron in an amount between about 3 wt % and about 20 wt %; wherein said amount of said aluminum is between about 1 wt % and about 4 wt %; wherein said hydroxypropionic acid is lactic acid; wherein said temperature is about 375° C. and said water partial pressure is about 13 bar; wherein said GHSV is about 2,300 h −1 and said WHSV is between about 0.3 h −1 and about 0.4 h −1 ; wherein said acrylic acid, acrylic acid derivatives, or mixtures thereof are produced with a yield of at least about 80% and with a selectivity of at least about 80% over a TOS of about 72 h; wherein said acrylic acid, acrylic acid derivatives, or mixtures thereof are produced with a yield of at least about 80 mol % and with a selectivity of at least about 80 mol % over a TOS of about 72 h; wherein propionic acid is produced as an impurity along with said acrylic acid, acrylic acid derivatives, or mixtures thereof; and wherein the selectivity of said propionic acid is less than about 1 mol % over said TOS of about 72 h.

Assignees

• Procter & Gamble

Inventors

• Collias Dimitris Ioannis
• Godlewski Jane Ellen
• Velasquez Juan Esteban

Classifications

• C07C59/08

  Lactic 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

• C07C51/04

  from carboxylic acid halides · CPC title

• B01J2219/02

  Apparatus characterised by their chemically-resistant properties · CPC title

• C07C45/72

  by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups · CPC title