IP Library Granted Patent US 7,317,130
Granted Patent B2
US 7,317,130 · App. 10/525,376 · Granted Jan 8, 2008

Method for the hydroformylation of olefinically unsaturated compounds, especially olefins, in the presence of cyclic carbonic acid esters

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 7,317,130
App. No.
10/525,376
Granted
Jan 8, 2008
Kind
B2
Abstract

The present invention relates to a process for preparing aldehydes by hydroformylation of olefinically unsaturated compounds catalyzed by metals of groups 8 to 10 of the Periodic Table of the Elements in the presence of cyclic carbonic esters and ligands which contain no sulfonic acid or sulfonate group.

Claims (21)

1. A process comprising hydroformylating an olefinically unsaturated compound having from 3 to 24 carbon atoms in the presence of at least one metal of groups 8 to 10 of the Periodic Table of the Elements as catalyst, wherein the hydroformylation is carried out in the presence of at least 0.1 mol %, based on the olefinically unsaturated compound, of at least one cyclic carbonic ester of the formula I

where

R 1 , R 2 , R 3 , R 4 are identical or different and are each H or a substituted or unsubstituted aliphatic, alicyclic, aromatic, aliphatic-alicyclic, aliphatic-aromatic or alicyclic-aromatic hydrocarbon radical having from 1 to 27 carbon atoms,

n is 0-5

X is a divalent substituted or unsubstituted, aliphatic, alicyclic, aromatic, aliphatic-alicyclic or aliphatic-aromatic hydrocarbon radical having from 1 to 27 carbon atoms,

and at least one ligand which contains no sulfonic acid group or sulfonate group, wherein the cyclic carbonic ester component is present in solvent amounts for the catalyst.

2. The process as claimed in claim 1 , wherein R 1 , R 2 , R 3 , R 4 and X are substituted by identical or different substituents selected from among O, N, NH, N-alkyl and N-dialkyl radicals, fluorine, chlorine, bromine, iodine, —OH, OR, —CN, —C(O)alkyl or —C(O)O-alkyl.

3. The process as claimed in claim 1 , wherein the hydroformylation is carried out in the presence of at least 0.1 mol %, based on the olefinically unsaturated compound, of at least one solvent which is relatively nonpolar compared to the cyclic carbonic ester I and is immiscible with the cyclic carbonic ester I.

4. The process as claimed in claim 3 , wherein substituted or unsubstituted hydrocarbons having from 5 to 50 carbon atoms, olefinically unsaturated compounds or olefins having from 3 to 24 carbon atoms are used as nonpolar solvent.

5. The process as claimed in claim 1 , wherein the output from the hydroformylation reaction is separated into a fraction comprising predominantly the catalyst and the cyclic carbonic ester and a fraction comprising predominantly the hydroformylation products.

6. The process as claimed in claim 3 , wherein the output from the hydroformylation reaction is separated into a fraction comprising predominantly the catalyst and a nonpolar solvent and a fraction comprising predominantly the hydroformylation products and the cyclic carbonic ester.

7. The process as claimed in claim 1 , wherein the output from the hydroformylation reaction is separated into a fraction comprising predominantly the catalyst and unreacted olefinically unsaturated compounds and a fraction comprising predominantly the hydroformylation products and the cyclic carbonic ester.

8. The process as claimed in claim 1 , wherein the fraction comprising the catalyst is recirculated to the hydroformylation reaction.

9. The process as claimed in claim 1 , wherein the cyclic carbonic ester used is ethylene carbonate, propylene carbonate or butylene carbonate or a mixture thereof.

10. The process as claimed in claim 1 , wherein the hydroformylation is carried out in the presence of phosphonites, phosphites, phosphine oxides, phosphines, phosphinites, phosphinines and/or phosphinanes.

11. The process as claimed in claim 1 , wherein unreacted olefinically unsaturated compounds (olefins) are separated off from the reactor output or from the hydroformylation products and are recirculated to the hydroformylation reaction.

12. The process as claimed in claim 1 , wherein unreacted olefinically unsaturated compounds are separated off from the reactor output or from the hydroformylation products and are used in a second reaction stage.

13. The process as claimed in claim 1 , which is carried out in the absence of carboxylic acids.

14. The process as claimed in claim 1 , wherein the metal comprises rhodium.

15. The process as claimed in claim 9 , wherein the cyclic carbonic ester used comprises propylene carbonate.

16. The process as claimed in claim 1 , wherein the cyclic carbonic ester component is present in an amount by weight greater than the amount of olefinically unsaturated compound.

Assignments (2)
CHANGE OF NAME Recorded Feb 25, 2010
From: OXENO OLEFINCHEMIE GMBH
To: EVONIK OXENO GMBH
Reel/Frame 024006/0287 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 8, 2006
From: MOELLER, OLIVER; FRIDAG, DIRK; BORGMANN, CORNELIA; HESS, DIETER; WIESE, KLAUS-DIETHER
To: OXENO OLEFINCHEMIE GMBH
Reel/Frame 017876/0877 →