IP Library Granted Patent US 11,384,042
Granted Patent B2
US 11,384,042 · App. 17/282,393 · Granted Jul 12, 2022

Process for hydroformylation of short-chain olefins in the gas phase

Inventors: Jennifer Haßelberg (Dortmund, DE); Robert Franke (Marl, DE); Frank Stenger (Alzenau, DE); Peter Kreis (Dortmund, DE); Corinna Hecht (Haltern am See, DE); Marc Oliver Kristen (Haltern am See, DE)
Assignee: Evonik Operations GmbH
C07C45/505B01J21/08B01J27/224B01J31/0271B01J31/20B01J31/2234B01J31/2404B01J35/026B01J2231/321B01J2531/004B01J2531/822
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Quick Facts
Patent No.
US 11,384,042
App. No.
17/282,393
Granted
Jul 12, 2022
Kind
B2
Abstract

A hydroformylation process can be used for short-chain olefins, especially C2 to C5 olefins, wherein the catalyst system is heterogenized on a support that contains a porous ceramic material. Systems can also be used for carrying out said process.

Claims (23)

1. A process for hydroformylating C2 to C8 olefins in a reaction zone using a heterogenized catalyst system, the process comprising:

passing a gaseous feed mixture containing the C2 to C8 olefins together with synthesis gas over a support composed of a porous ceramic material, on which the catalyst system is in a heterogenized form;

wherein the catalyst system comprises a metal from group 8 or 9 of the Periodic Table of the Elements, at least one organic phosphorus-containing ligand, a stabilizer, and optionally, an ionic liquid;

wherein the support is in the form of a powder, in the form of a granular material, or in the form of pellets and wherein the support consists of a carbidic ceramic material, a nitridic ceramic material, a silicidic ceramic material, or a mixture thereof; and

wherein a washcoat of the same or another ceramic material, with respect to the ceramic material of the support, is applied on the support.

2. The process according to claim 1 , wherein the at least one organic phosphorus-containing ligand in the hydroformylation catalyst system has the general formula (VI):

R′-A-R″-A-R′″  (VI),

wherein R′, R″, and R′″ are each organic radicals,

with the proviso that R′ and R′″ are not identical, and

wherein each A is a bridging —O—P(—O) 2 — group, where two of the three oxygen atoms —O— are each bonded to the radical R′ and the radical R′″.

3. The process according to claim 1 , wherein the stabilizer is an organic amine compound containing at least one 2,2,6,6-tetramethylpiperidine unit of formula (I):

4. The process according to claim 1 , wherein when said support consists of a nitridic ceramic material, the nitridic ceramic material is selected from the group consisting of silicon nitride, boron nitride, aluminium nitride, and mixtures thereof;

wherein when said support consists of a carbidic ceramic material, the carbidic ceramic materials selected from the group consisting of silicon carbide, boron carbide, tungsten carbide, and mixtures thereof; and

wherein when said support consists of a silicidic ceramic material, the silicidic ceramic material is molybdenum silicide.

5. The process according to claim 4 , wherein the support consists of a carbidic ceramic material.

6. The process according to claim 5 , wherein the support consists of silicon carbide.

7. The process according to claim 1 , wherein the amount of the washcoat present on the support is ≤20% by weight, based on the total amount of support.

8. The process according to claim 1 , wherein the support has a median particle diameter (d50) of 0.1 mm to 7 mm.

9. The process according to claim 1 , wherein the hydroformylation is conducted at a temperature in the range from 65 to 200° C.

10. The process according to claim 1 , wherein the hydroformylation is conducted at a pressure not greater than 35 bar.

11. The process according to claim 1 , wherein the catalyst system does not comprise any ionic liquid.

12. The process according to claim 9 , wherein the hydroformylation is conducted at a temperature in the range from 85 to 150° C.

13. The process according to claim 10 , wherein the hydroformylation is conducted at a pressure not greater than 25 bar.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 19, 2023
From: EVONIK OPERATIONS GMBH
To: EVONIK OXENO GMBH & CO. KG
Reel/Frame 065692/0785 →
Priority Claims (1)
EP 18198794 · Oct 5, 2018 · regional
Continuity (1)
Related Publication 20210340091A1 · Nov 4, 2021