Low-pressure hydroformylation of diisobutene

Patent metadata

Field	Value
Publication number	US-12281063-B2
Application number	US-202117798607-A
Country	US
Kind code	B2
Filing date	Feb 1, 2021
Priority date	Feb 11, 2020
Publication date	Apr 22, 2025
Grant date	Apr 22, 2025

Abstract

A hydroformylation process for preparing 3,5,5-trimethylhexanal comprising reacting 2,4,4-trimethylpent-2-ene with H2 and CO in a reaction zone in the presence of one or more free organophosphite ligands of the general formula (I)wherein R1, R2, R3, R4 and R5 are each independently H, C1- to C9-alkyl or C1- to C9-alkoxy and R1, R2,R3, R4 and R5 are not H at the same time, andR6, R7, R8, R° and R1° are each independently H, C1- to C9-alkyl or C1- to C9-alkoxy and Re, R7,R8, R° and R1° are not H at the same time, andR11, R12, R13, R14 and R15 are each independently H, C1- to C9-alkyl or C1- to C9-alkoxy and R11,R12, R13, R14 and R15 are not H at the same time,and a homogeneous rhodium catalyst complexed with one or more organophosphite ligands of the general formula (I) at a pressure of 1 to 100 bar abs and a temperature of from 50 to 200° C.

First claim

The invention claimed is:

1. A hydroformylation process for preparing 3,5,5-trimethylhexanal comprising reacting 2,4,4-trimethylpent-2-ene with H 2 and CO in a reaction zone in the presence of one or more free organophosphite ligands of general formula (I)

wherein,
R 1 , R 2 , R 3 , R 4 and R 5 are each independently H, C 1 - to C 9 -alkyl or C 1 - to C 9 -alkoxy and R 1 , R 2 , R 3 , R 4 and R 5 are not H at the same time, and
R 6 , R 7 , R 8 , R 9 and R 10 are each independently H, C 1 - to C 9 -alkyl or C 1 - to C 9 -alkoxy and R 6 , R 7 , R 8 , R 9 and R 10 are not H at the same time, and
R 11 , R 12 , R 13 , R 14 and R 15 are each independently H, C 1 - to C 9 -alkyl or C 1 - to C 9 -alkoxy and R 11 , R 12 , R 13 , R 14 and R 15 are not H at the same time,
and a homogeneous rhodium catalyst complexed with one or more organophosphite ligands of the general formula (I) at a pressure of 1 to 100 bar abs and a temperature of from 50 to 200° C.

2. The process according to claim 1 , wherein a mixture comprising 2,4,4-trimethylpent-1-ene and 2,4,4-trimethylpent-2-ene is converted to 3,5,5-trimethylhexanal.

3. The process according to claim 2 , wherein the ratio of 2,4,4-trimethylpent-1-ene to 2,4,4-trimethylpent-2-ene in the mixture used is in the range from 99:1 to 1:99.

4. The process according to claim 1 , wherein the total amount of 2,4,4-trimethylpent-1-ene and 2,4,4-trimethylpent-2-ene of the total amount of olefin in the feed to the reaction zone is from 10 to 100%.

5. The process according to claim 1 , wherein the hydroformylation is carried out at a temperature of 80 to 150° C.

6. The process according to claim 1 , wherein the hydroformylation is carried out at a pressure of 5 to 80 bar abs.

7. The process according to claim 1 , wherein the molar ratio of the total amount of organophosphite ligands of the general formula (I) in the reaction zone to the total amount of rhodium in the reaction zone is in the range from 1:1 to 100:1.

8. The process according to claim 1 , wherein the rhodium concentration in the reaction zone is in the range of 20 to 250 ppmw based on the total weight of the liquid phase in the liquid phase in the reaction zone.

9. The process according to claim 1 , wherein the one or more organophosphite ligands of the general formula (I) are one or more of the following compounds:

Organophosphite

ligand of general

R 2 , R 4 , R 5 , R 7 , R 9 ,

formula (I)
R 1 , R 6 , R 11
R 3 , R 8 , R 13
R 10 , R 12 , R 14 , R 15

I)
Methyl
Methyl
H

II)
Methyl
H
H

III)
Ethyl
Ethyl
H

IV)
Ethyl
H
H

V)
n-Propyl
n-Propyl
H

VI)
n-Propyl
H
H

VII)
Isopropyl
Isopropyl
H

VIII)
Isopropyl
H
H

IX)
n-Butyl
n-Butyl
H

X)
n-Butyl
H
H

XI)
sec-Butyl
sec-Butyl
H

XII)
sec-Butyl
H
H

XIII)
Isobutyl
Isobutyl
H

XIV)
Isobutyl
H
H

XV)
tert-Butyl
tert-Butyl
H

XVI)
tert-Butyl
H
H

XVII)
Methoxy
Methoxy
H

XVIII)
Methoxy
H
H

XIX)
Ethoxy
Ethoxy
H

XX)
n-Propoxy
n-Propoxy
H

XXI)
n-Propoxy
H
H

XXII)
Isopropoxy
Isopropoxy
H

XXIII)
Isopropoxy
H
H

XXIV)
n-Butoxy
n-Butoxy
H

XXV)
n-Butoxy
H
H

XXVI)
sec-Butoxy
sec-Butoxy
H

XXVII)
sec-Butoxy
H
H

XXVIII)
Isobutoxy
Isobutoxy
H

XXIX)
Isobutoxy
H
H

XXX)
tert-Butoxy
tert-Butoxy
H

XXXI)
tert-Butoxy
H
H

XXXII)
n-Nonyl
H
H.

10. The

Assignees

• Basf Se

Inventors

• Schwaben Jonas
• Paciello Rocco
• Papp Rainer

Classifications

• C07C49/203

  with only carbon-to-carbon double bonds as unsaturation · CPC title

• C07C45/50 Primary

  by oxo-reactions · CPC title

• C07C45/505 Primary

  Asymmetric hydroformylation · CPC title

• C07F9/145 Primary

  with hydroxyaryl compounds · CPC title