IP Library › Granted Patent US 10,377,727
Granted Patent B2
US 10,377,727 · App. 15/765,738 · Granted Aug 13, 2019

Process for the preparation of gamma-valerolactone

Inventors: Nicolas André Vélu Popoff (Amsterdam, NL); Jan Cornelis van der Waal (Amsterdam, NL)
Assignee: Synvina C.V.
C07D307/33B01J21/04B01J21/063B01J21/066B01J21/08B01J21/12B01J23/04B01J23/72B01J23/755B01J23/80B01J23/892B01J23/8966
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Quick Facts
Patent No.
US 10,377,727
App. No.
15/765,738
Granted
Aug 13, 2019
Kind
B2
Abstract

Gamma-valerolactone is prepared from a levulinic acid ester in a continuous process where a stream of the levulinic acid ester together with a gaseous stream of a hydrogen-containing gas is contacted with a hydrogenation catalyst, where the levulinic acid ester is in the liquid phase, and where the hydrogenation catalyst is a solid particulate catalyst including at least one hydrogenating metal, supported on an oxide carrier.

Claims (32)

1. A continuous process for the preparation of gamma-valerolactone (GVL) from a levulinic acid ester comprising:

contacting a stream of the levulinic acid ester together with a gaseous stream of a hydrogen-containing gas with a hydrogenation catalyst,

wherein the levulinic acid ester is in the liquid phase,

wherein the hydrogenation catalyst is a solid particulate catalyst comprising at least one hydrogenating metal, supported on an oxide carrier, and

which is conducted in the absence of solvent.

2. The process according to claim 1 , wherein the hydrogenating metal in the hydrogenation catalyst is selected from the group consisting of one or more of the metals of groups 8 to 11 of the Periodic Table of Elements.

3. The process according to claim 1 , wherein the levulinic acid ester is an alkyl levulinate.

4. The process according to claim 1 , which is conducted at a temperature in the range of 75 to 400° C.

5. The process according to claim 1 , wherein the hydrogenation catalyst comprises nickel as hydrogenating metal.

6. The process according to claim 5 , wherein the hydrogenation catalyst comprises nickel in an amount of 1 to 75% wt, calculated as metal and based on the hydrogenation catalyst.

7. The process according to claim 5 , wherein the hydrogenation catalyst comprises a platinum-group metal as dopant.

8. The process according to claim 1 , wherein the hydrogenation catalyst comprises copper as hydrogenating metal.

9. A continuous process for the preparation of gamma-valerolactone (GVL) from a levulinic acid ester comprising:

contacting a stream of the levulinic acid ester together with a gaseous stream of a hydrogen-containing gas with a hydrogenation catalyst,

wherein the levulinic acid ester is in the liquid phase,

wherein the hydrogenation catalyst is a solid particulate catalyst comprising at least one hydrogenating metal, supported on an oxide carrier,

wherein the hydrogenation catalyst comprises copper as hydrogenating metal, and

wherein the hydrogenation catalyst comprises a zinc compound as dopant.

10. The process according to claim 9 , wherein the hydrogenation catalyst comprises copper in an amount of 1 to 75% wt, calculated as metal and based on the hydrogenation catalyst.

11. A continuous process for the preparation of gamma-valerolactone (GVL) from a levulinic acid ester comprising:

contacting a stream of the levulinic acid ester together with a gaseous stream of a hydrogen-containing gas with a hydrogenation catalyst,

wherein the levulinic acid ester is in the liquid phase,

wherein the hydrogenation catalyst is a solid particulate catalyst comprising at least one hydrogenating metal, supported on an oxide carrier, and

wherein the hydrogenation catalyst comprises a platinum-group metal as hydrogenating metal and, optionally, tin or a tin compound as dopant.

12. The process according to claim 11 , wherein the platinum group metal is platinum.

13. The process according to claim 11 , wherein the hydrogenation catalyst comprises a platinum group metal in an amount of 0.1 to 7.5% wt, calculated as metal and based on the hydrogenation catalyst.

14. The process according to claim 11 , wherein the hydrogenation catalyst comprises tin or a tin compound in an amount of 20 to 200% wt, calculated as metal and based on the platinum-group metal.

15. The process according to claim 9 , wherein the oxide carrier contains an alkali metal.

16. The process according to claim 15 , wherein the alkali metal is potassium.

17. The process according to claim 15 , wherein the amount of alkali metal is in the range of 0.2 to 10% wt, calculated as element and based on the oxide carrier.

18. The process according to claim 11 , wherein the oxide carrier is selected from the group consisting of alumina, silica, zirconia, titania and mixtures thereof.

19. The process according to claim 5 , wherein the hydrogenation catalyst is supported on a carrier of aluminum oxide.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 4, 2020
From: SYNVINA C.V.
To: FURANIX TECHNOLOGIES B.V.
Reel/Frame 052005/0498 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 5, 2018
From: POPOFF, NICOLAS ANDRÉ VÉLU; VAN DER WAAL, JAN CORNELIS
To: SYNVINA C.V.
Reel/Frame 046268/0241 →
Priority Claims (1)
NL 2015578 · Oct 6, 2015 · national
Continuity (1)
Related Publication 20180290993A1 · Oct 11, 2018