DIPHOSPHITE WITH ONE ME WING BLOCK AND ONE TBU WING BLOCK

Description

[0001] The invention relates to a diphosphite with a Me-wing building block and a t< Bu-wing building block and its use in hydroformylation.

[0002] Phosphorus-containing compounds play a crucial role as ligands in a variety of reactions, e.g. in hydrogenation, hydrocyanation and also in hydroformylation.

[0003] CN 215 196 872 U describes diphosphites and their use in hydroformylation.

[0004] CN 103 467 517 B describes a process for the preparation of a diphosphite.

[0005] The technical object of the invention is to provide a compound with which an increased yield can be achieved in the hydroformylation of olefins.

[0006] The object is achieved by a connection according to claim 1.

[0007] Compound having the structure (1):

[0008] In addition to the connection itself, a method is also claimed in which the connection described above is used.

[0009] Procedure comprising the following steps: a) Initially introducing an olefin; b) adding the compound described above; c) adding a substance comprising Rh; d) supplying H 2 and CO; e) heating the reaction mixture from a) to d), whereby the olefin is converted to an aldehyde.

[0010] In a variant of the process, the substance comprising Rh is selected from: Rh(acac)(CO) 2 , [(acac)Rh(COD)] (acac = acetylacetonate anion; COD = 1,5-cyclooctadiene), Rh 4 CO 12 .

[0011] In a variant of the method, the substance comprising Rh is Rh(acac)(CO) 2 .

[0012] In the following, the invention will be explained in more detail using an exemplary embodiment. Catalysis experiments

[0013] The hydroformylation was carried out in a 16 ml autoclave from the HEL group, Hertfordshire, UK, equipped with pressure control, gas flow measurement, and a gassing stirrer. The substrate (1-octene) was heated to reflux over sodium for several hours and distilled under argon.

[0014] For the experiments, the reaction solutions were prepared in advance under an argon atmosphere. 100 ppm of Rh(acac)(CO)2 and the corresponding amount of ligand (L:Rh = 50:1) were weighed and made up to the desired temperature with 8.0 ml of toluene. The mass of toluene added in each case was determined for GC analysis. 1.80 g of 1-octene (16 mmol) were then added. The prepared solutions were then filled into the autoclave, which was flushed three times with argon and three times with synthesis gas (Linde; H2 (99.999%):CO (99.997%) = 1:1). The autoclave was then heated to the desired temperature at a total pressure of 10 bar while stirring (900 rpm). Once the reaction temperature was reached, the synthesis gas pressure was increased to 17 bar, and the reaction was conducted at constant pressure for 1 h. After the reaction time, the autoclave was cooled to room temperature, depressurized while stirring, and purged with argon.After completion of the reaction, 0.5 ml of each reaction mixture was removed, diluted with 4 ml of pentane, and analyzed by gas chromatography: HP 5890 Series II plus, PONA, 50 m x 0.2 mm x 0.5 µm. The quantitative determination of residual olefin and aldehyde was performed using toluene as an internal standard.

[0015] The experiment was carried out with the compounds (1) and (2) carried out.

[0016] The experiment with the connection (2) serves as a comparison test. Results of the catalysis experiments

[0017] [Rh]: 100 ppm, p: 17 bar, T: 120 °C; t: 1 h Table: Hydroformylation of 1-octene Yield [%] (1)* 18 (2) 11 *compound according to the invention

[0018] The tests carried out prove that the task is solved by a compound according to the invention.

Claims

1. Compound having the structure (1):

2. Process comprising the process steps of: a) initially charging an olefin; b) adding a compound according to Claim 1; c) adding a substance comprising Rh; d) feeding in H2 and CO; e) heating the reaction mixture from a) to d), to convert the olefin to an aldehyde.

3. Process according to Claim 2, wherein the substance comprising Rh is selected from: Rh(acac) (CO)2, [(acac)Rh(COD)] (acac = acetylacetonate anion; COD = 1,5-cyclooctadiene), Rh4CO12.

4. Process according to either of Claims 2 and 3, wherein the substance comprising Rh is Rh(acac) (CO)2.