Hydroformylation method for the large-scale production of aldehydes and/or alcohols

Patent metadata

Field	Value
Publication number	US-11014863-B2
Application number	US-201816613307-A
Country	US
Kind code	B2
Filing date	May 14, 2018
Priority date	May 16, 2017
Publication date	May 25, 2021
Grant date	May 25, 2021

Abstract

A process for preparing C4 to C13 monohydroxy compounds from a bottom fraction arising in the distillation of a crude mixture of C4 to C13 oxo-process aldehydes from cobalt-catalyzed or rhodium-catalyzed hydroformylation, or in the distillation of a crude mixture of C4 to C13 oxo-process alcohols, which comprises contacting the bottom fraction in the presence of hydrogen with a catalyst comprising copper oxide and aluminum oxide, at a temperature of 150° C. to 300° C. and a pressure of 20 bar to 300 bar and subjecting the resulting crude hydrogenation product to distillation, and the amount of C4 to C13 monohydroxy compounds present in the crude hydrogenation product after the hydrogenation being greater than the amount of C4 to C13 monohydroxy compounds given stoichiometrically from the hydrogenation of the ester and aldehyde compounds present in the bottom fraction, including the C4 to C13 monohydroxy compounds still present in the bottom fraction before the hydrogenation.

First claim

The invention claimed is:

1. A process for preparing C 4 to C 13 monohydroxy compounds from a bottom fraction arising in the distillation of a crude mixture of C 4 to C 13 oxo-process aldehydes from cobalt-catalyzed or rhodium-catalyzed hydroformylation, or in the distillation of a crude mixture of C 4 to C 13 oxo-process alcohols, which comprises contacting the bottom fraction in the presence of hydrogen with a catalyst comprising copper oxide (CuO) and aluminum oxide, at a temperature of 180° C. to 260° C. and a pressure of 150 bar to 280 bar and subjecting the resulting crude hydrogenation product to distillation, and the amount of C 4 to C 13 monohydroxy compounds present in the crude hydrogenation product after the hydrogenation being greater than the amount of C 4 to C 13 monohydroxy compounds given stoichiometrically from the hydrogenation of the ester and aldehyde compounds present in the bottom fraction, including the C 4 to C 13 monohydroxy compounds still present in the bottom fraction before the hydrogenation.

2. The process according to claim 1 , wherein the catalyst comprises copper oxide (CuO) with a fraction of 40 to 80 weight percent, aluminum oxide with a fraction of 5 to 60 weight percent, and 0 to 30 weight percent of manganese oxide (MnO), lanthanum oxide or zinc oxide, the weight percentages are based on the total weight of the oxidic material present in the catalyst after calcining, the sum of the weight fractions adds up to 90 to 100 percent, and the fraction of oxidic material in the catalyst is at least 80 weight percent, based on the total weight of the catalyst after calcining.

3. The process according to claim 1 , for producing C 4 to C 9 monohydroxy compounds from a bottom fraction arising in the distillation of a crude mixture of C 4 to C 9 oxo-process aldehydes from cobalt-catalyzed or rhodium-catalyzed hydroformylation, or in the distillation of a crude mixture of C 4 to C 9 oxo-process alcohols.

4. The process according to claim 3 , for producing n-butanol and/or isobutanol from a bottom fraction arising in the distillation of a crude mixture of C 4 oxo-process aldehydes from rhodium-catalyzed hydroformylation, or in the distillation of a crude mixture of C 4 oxo-process alcohols.

5. The process according to claim 1 , wherein the bottom fraction, before being contacted with hydrogen and a catalyst, is subjected to extraction, distillation or stripping.

6. The process according to claim 1 , wherein the bottom fraction, before being contacted with hydrogen and a catalyst, is subjected to extraction and distillation.

7. The process according to claim 1 , wherein a part of the crude hydrogenation product obtained from the hydrogenation is returned to the disclosed process and a part of the crude hydrogenation product obtained from the hydrogenation is subjected to distillation.

8. A process for preparing C 4 monohydroxy compounds by hydrogenolysis of C 8 diols, which comprises contacting C 8 diols in the presence of hydrogen with a catalyst comprising copper oxide and aluminum oxide, at a temperature of 150° C. to 300° C. and a pressure of 20 bar to 300 bar, reacting the C 8 diols at least partially to give C 4 monohydroxy compounds, and subjecting the resulting crude C 8 diol hydrogenation product to distillation.

9. A process for preparing C 4 monohydroxy compounds from the bottom fraction arising in the distillation of a crude mixture of C 4 oxo-process aldehydes from rhodium-catalyzed hydroformylation or in the distillation of a crude mixture of C 4 oxo-process alcohols, which comprises contacting the bottom fraction in the presence of hydrogen with a catalyst comprising copper oxide and aluminum oxide, at a temperature of 150° C. to 300° C. and a pressure of 20 bar to 300 bar and subjecting the resulting crude hydrogenation product to distillation, and the amount of n-butanol, isobutanol or a mixture thereof present in the crude hydrogenation product after the hydrogenation being greater than the amount of n-butanol, isobutanol or a mixture thereof given stoichiometrically from the hydrogenation of the ester and aldehyde compounds present in the bottom fraction, including the C 4 monohydroxy compounds still present in the bottom fraction before the hydrogenation.

Assignees

• Basf Se

Inventors

• Zuend Stephan
• Papp Rainer
• Breitscheidel Boris
• Lange De Oliveira Armin

Classifications

• C07C47/02

  Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen · CPC title

• C07C45/50

  by oxo-reactions · CPC title

• C07C31/12

  containing four carbon atoms · CPC title

• C07C29/149 Primary

  with hydrogen or hydrogen-containing gases · CPC title

• C07C29/141

  with hydrogen or hydrogen-containing gases · CPC title