IP Library Granted Patent US 9,505,693
Granted Patent B2
US 9,505,693 · App. 14/351,331 · Granted Nov 29, 2016

Process for the hydrodechlorination of a liquid feed comprising dichloroacetic acid

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Quick Facts
Patent No.
US 9,505,693
App. No.
14/351,331
Granted
Nov 29, 2016
Kind
B2
Abstract

The process of the present invention pertains to a process wherein a liquid feed comprising monochloroacetic acid, dichloroacetic acid, and optionally acetic acid and/or trichloroacetic acid is subjected to a catalytic hydrodechlorination step by contacting it with a source of hydrogen in the presence of a solid heterogeneous hydrogenation catalyst situated in a fixed catalyst bed, wherein the liquid feed is fed to the top of avertical tubular reactor at a superficial mass velocity of between and 10 kg/s per square meter of the horizontal cross-section of the vertical tubular reactor and a rate of between 250 and 3,000 kg/hr per m of said catalyst bed, wherein the source of hydrogen is fed to the top or bottom of the vertical tubular reactor at a rate of between 0.025 to 0.25 Nm/s per square meter of the horizontal cross-section of the vertical tubular reactor, so as to obtain an average axial pressure gradient of at least 2 kPa per meter of said catalyst bed, and wherein the temperature in the top of the vertical tubular reactor is between 100 and 200° C., and wherein the pressure in the top of the vertical tubular reactor is between 0.2 and 1.0 MPa.

Claims (26)

1. A process comprising subjecting a liquid feed comprising monochloroacetic acid and dichloroacetic acid to a catalytic hydrodechlorination step by contacting it with a source of hydrogen to convert the dichloroacetic acid into monochloroacetic acid in the presence of a solid heterogeneous hydrogenation catalyst comprising one or more metals of Group VIII of the Periodic Table of the Elements deposited on a carrier, wherein said catalytic hydrodechlorination step is carried out in a vertical tubular reactor with a diameter exceeding 0.4 m, with the solid heterogeneous hydrogenation catalyst being situated in a fixed catalyst bed, wherein the liquid feed is fed to the top of said vertical tubular reactor at a superficial mass velocity of between 1 and 10 kg/s per square meter of the horizontal cross-section of the vertical tubular reactor and a rate of between 250 and 3,000 kg/hr per m 3 of said catalyst bed, wherein the source of hydrogen is fed to the top or bottom of the vertical tubular reactor at a superficial gas velocity of between 0.025 to 0.25 Nm 3 /s per square meter of the horizontal cross-section of the vertical tubular reactor, so as to obtain an average axial pressure gradient of at least 2 kPa per meter of said catalyst bed, and wherein the temperature in the top of the vertical tubular reactor is between 100 and 200° C., and wherein the pressure in the top of the vertical tubular reactor is between 0.2 and 1.0 MPa.

2. The process according to claim 1 wherein the liquid feed fed to the top of said vertical tubular reactor comprises at least 5.5% by weight acetic acid.

3. The process according to claim 1 wherein the fixed catalyst bed in which the heterogeneous hydrogenation catalyst is situated has been prepared by loading the vertical tubular reactor with the heterogeneous hydrogenation catalyst using a dense loading technique.

4. The process according to claim 1 wherein the liquid feed is fed to the top of said vertical tubular reactor at a superficial mass velocity of between 2.5 and 6 kg/s per square meter of the horizontal cross-section of the vertical tubular reactor.

5. The process according to claim 1 wherein the heterogeneous hydrogenation catalyst comprises between 0.1 and 3% by weight, based on the total weight of the heterogeneous hydrogenation catalyst, of the one or more metals of Group VIII of the Periodic Table of the Elements.

6. The process according to claim 1 wherein the carrier is selected from the group consisting of activated carbon, silica, alumina, zirconium oxide, and titanium oxide.

7. The process according to claim 6 , wherein the carrier is in the form of particles, said particles being in the form of irregularly shaped granules, spheres, rings, trilobes, quadrulobes, or extrudates.

8. The process according to claim 7 wherein the particles are in the form of extrudates, trilobes, or quadrulobes, and wherein said extrudates, trilobes or quadrulobes have a diameter of between 0.8 and 3 mm and a length of between 1 and 10 mm.

9. The process according to claim 1 wherein the heterogeneous hydrogenation catalyst comprises at least one of palladium and platinum.

10. The process according to claim 1 wherein the temperature in the top of the vertical tubular reactor is between 145 and 175° C.

11. The process according to claim 1 wherein the source of hydrogen is fed to the top of the vertical tubular reactor, resulting in a co-current downflow with the liquid feed.

12. The process according to claim 11 wherein the pressure in the top of the vertical tubular reactor is between 0.3 and 0.6 MPa.

13. The process according to claim 1 wherein the source of hydrogen is fed to the bottom of the vertical tubular reactor and the pressure at the bottom of the vertical tubular reactor is between 0.3 and 0.6 MPa.

14. The process according to claim 1 wherein the liquid feed subjected to the catalytic hydrodechlorination step comprises

(i) between 60 and 99.5% by weight of monochloroacetic acid,

(ii) between 0.05 and 20% by weight of dichloroacetic acid,

(iii) between 0 and 30% by weight of acetic acid,

(iv) between 0.1 and 5% by weight of water, and

(v) between 0 and 5% by weight of other components,

up to a total of 100%, based on the total weight of the liquid feed.

15. The process according to claim 3 wherein the liquid feed is fed to the top of said vertical tubular reactor at a superficial mass velocity of between 2.5 and 6 kg/s per square meter of the horizontal cross-section of the vertical tubular reactor.

16. The process according to claim 4 wherein the heterogeneous hydrogenation catalyst comprises between 0.1 and 3% by weight, based on the total weight of the heterogeneous hydrogenation catalyst, of the one or more metals of Group VIII of the Periodic Table of the Elements.

17. The process according to claim 5 wherein the carrier is selected from the group consisting of activated carbon, silica, alumina, zirconium oxide, and titanium oxide.

18. The process according to claim 3 wherein the temperature in the top of the vertical tubular reactor is between 145 and 175° C.

19. The process according to claim 5 wherein the source of hydrogen is fed to the top of the vertical tubular reactor, resulting in a co-current downflow with the liquid feed.

20. The process according to claim 9 wherein the source of hydrogen is fed to the bottom of the vertical tubular reactor and the pressure at the bottom of the vertical tubular reactor is between 0.3 and 0.6 MPa.

Assignments (4)
CHANGE OF NAME Recorded Sep 18, 2019
From: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: NOURYON CHEMICALS INTERNATIONAL B.V.
Reel/Frame 050426/0671 →
SECURITY INTEREST Recorded Oct 1, 2018
From: STARFRUIT US MERGER SUB 1 LLC; STARFRUIT US MERGER SUB 2 LLC; AKZO NOBEL SURFACE CHEMISTRY LLC; AKZO NOBEL CHEMICALS B.V.; AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: WILMINGTON TRUST (LONDON) LIMITED, AS COLLATERAL AGENT
Reel/Frame 047231/0001 →
CHANGE OF ADDRESS Recorded May 15, 2017
From: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 042745/0406 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 15, 2014
From: NIEUWHOF, MELLE RINZE; KOOIJMAN, CORNELIS; VOS, HENDRIK JAN; TOLLIN, LARS MAGNUS; VAN DEN BERG, JACOBUS; VAN HAL, HENRICUS JOHANNES MARINUS PETRUS
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 033545/0861 →