IP Library Granted Patent US 9,505,694
Granted Patent B2
US 9,505,694 · App. 14/351,313 · Granted Nov 29, 2016

Process for the purification of a liquid feed comprising MCA and DCA

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Quick Facts
Patent No.
US 9,505,694
App. No.
14/351,313
Granted
Nov 29, 2016
Kind
B2
Abstract

The present invention pertains to a process for the purification of a substantially water-free liquid feed comprising monochloroacetic acid, dichloroacetic acid, optionally acid chlorides, optionally anhydrides, and optionally acetic acid, which comprises the steps of (a) adding water to the liquid feed so that a liquid feed is obtained comprising between 0.01 and 5% by weight of water, based on the total weight of the liquid feed, and (b) subsequently subjecting the liquid feed obtained in step (a) 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.

Claims (30)

1. A process for the purification of a substantially water-free liquid feed comprising monochloroacetic acid and dichloroacetic acid to produce a hydrogenation product, which comprises the steps of

(a) obtaining the substantially water-free liquid feed from a section of a monochloroacetic acid production plant wherein acetic acid is reacted with chlorine in the presence of a catalyst,

(b) stripping the substantially water-free liquid feed using HCl at a pressure between 2 and 10 bar,

(c) adding water to the substantially water-free liquid feed so that a second liquid feed is obtained comprising between 0.01 and 5% by weight of water, based on the total weight of the second liquid feed, and

(d) subsequently subjecting the second liquid feed 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, thus producing the hydrogenation product,

wherein the hydrogenation product is a monochloroacetic acid-comprising product having a reduced dichloroacetic acid content and a Pt—Co color (as determined according to ISO-6271) that is equal to or below a value of 300.

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

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

4. 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.

5. The process according to claim 1 wherein the substantially water-free liquid feed comprises between 0.01 and 35% by weight of acid chlorides.

6. The process according to claim 1 wherein the second liquid feed 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 0.1 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 second liquid feed.

7. The process according to claim 1 wherein the hydrodechlorination step is carried out using a vertical tubular reactor containing the solid hydrogenation heterogeneous catalyst.

8. The process according to claim 7 wherein the solid hydrogenation heterogeneous catalyst is situated in a fixed catalyst bed.

9. The process according to claim 8 wherein the second liquid feed is fed to the top of the vertical tubular reactor and hydrogen gas or a mixture of hydrogen gas and up to 50 mole % of an inert gas is either fed to the top or fed to the bottom of the vertical tubular reactor.

10. The process according to claim 7 wherein hydrogen gas or a mixture of hydrogen gas and up to 50 mole % of an inert gas is fed to the top of the vertical tubular reactor, 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.

11. The process according to claim 7 wherein hydrogen gas or a mixture of hydrogen gas and up to 50 mole % of an inert gas is fed to the bottom of the vertical tubular reactor, the temperature at the top of the vertical tubular reactor is between 100 and 200° C. and wherein the pressure at the bottom of the vertical tubular reactor is between 0.2 and 1.0 MPa.

12. The process according to claim 3 wherein the carrier is selected from the group consisting of activated carbon, silica, alumina, zirconium oxide, and titanium oxide.

13. The process according to claim 4 wherein the substantially water-free liquid feed comprises between 0.01 and 35% by weight of acid chlorides.

14. The process according to claim 2 wherein the hydrodechlorination step is carried out using a vertical tubular reactor containing the solid hydrogenation heterogeneous catalyst.

15. The process according to claim 14 wherein the solid hydrogenation heterogeneous catalyst is situated in a fixed catalyst bed.

16. The process according to claim 15 wherein the second liquid feed is fed to the top of the vertical tubular reactor and hydrogen gas or a mixture of hydrogen gas and up to 50 mole % of an inert gas is either fed to the top or fed to the bottom of the vertical tubular reactor.

17. The process according to claim 14 wherein hydrogen gas or a mixture of hydrogen gas and up to 50 mole % of an inert gas is fed to the top of the vertical tubular reactor, 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.

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

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

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 Feb 21, 2015
From: NIEUWHOF, MELLE RINZE; KOOIJMAN, CORNELIS; KOELEWIJN, WILLEM; VOS, HENDRIK JAN; TOLLIN, LARS MAGNUS; VAN HAL, HENRICUS JOHANNES MARINUS PETRUS
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 035000/0687 →