Single step conversion of N-butyraldehyde to 2-ethylhexanal

Patent metadata

Field	Value
Publication number	US-9822053-B2
Application number	US-201615009098-A
Country	US
Kind code	B2
Filing date	Jan 28, 2016
Priority date	Jan 28, 2016
Publication date	Nov 21, 2017
Grant date	Nov 21, 2017

Abstract

Disclosed is a method of making and using a titania supported palladium catalyst for the single step synthesis of 2-ethylhexanal from a feed of n-butyraldehyde. This titania supported palladium catalyst demonstrates high n-butyraldehyde conversion but also produces 2-ethylhexanal in an appreciable yield with maintained activity between runs. This method provides a single step synthesis of 2-ethylhexanal from n-butyraldehyde with a catalyst that can be regenerated that provides cleaner downstream separations relative to the traditional caustic route.

First claim

What is claimed is:

1. A method for a single step synthesis of 2-ethylhexanal comprising: contacting n-butyraldehyde and a hydrogen gas with a palladium on titania eggshell type catalyst under vapor-phase condensation conditions to obtain a reaction product comprising 2-ethylhexanal;
wherein the palladium eggshell catalyst comprises a palladium shell deposited on a titania support comprising nano-sized particles of palladium having a diameter less than about 10 nanometers; and
wherein the palladium shell deposited on the titania support is concentrated within about 300 micrometers of the palladium eggshell type catalyst's exterior surface.

2. The method according to claim 1 , wherein the nano-sized particles of palladium have a diameter of less than about 2 nanometers.

3. The method according to claim 1 , wherein the n-butyraldehyde and the palladium eggshell type catalyst are contacted at about atmospheric pressure.

4. The method according to claim 1 , wherein the n-butyraldehyde and the palladium eggshell type catalyst are contacted at a temperature of about 290° C.

5. The method according to claim 1 , wherein the reaction product comprises at least 30 weight % 2-ethylhexanal.

6. The method according to claim 1 , wherein the conversion of n-butyraldehyde is at least 70%.

7. The method according to claim 1 , wherein the palladium eggshell catalyst has 0.1 weight % palladium nanoparticles on the titania.

8. The method according to claim 1 , wherein the palladium eggshell catalyst can be regenerated in air at a temperature from about 400° C. to about 450° C.

9. A method for a single step synthesis of 2-ethylhexanal comprising: contacting n-butyraldehyde and a hydrogen gas with a palladium on titania eggshell type catalyst under vapor-phase condensation conditions at about atmospheric pressure to obtain a reaction product comprising 2-ethylhexanal;
wherein the palladium eggshell catalyst comprises about 0.1 weight % of a palladium metal shell deposited on a titania support comprising nano-sized particles of palladium having a diameter less than about 2 nanometers; and
wherein the palladium shell deposited on the titania support is concentrated within about 300 micrometers of the palladium eggshell type catalyst's exterior surface.

10. The method according to claim 9 , wherein the n-butyraldehyde and the palladium on titania eggshell type catalyst are contacted to obtain a reaction mixture comprising at least 80 weight % 2-ethylhexanal, 2-ethylhexenal, and 2-ethylhexanol.

11. The method according to claim 9 , wherein less than 10 weight % of the reaction product are heptenes.

12. The method according to claim 9 , wherein the n-butyraldehyde and the palladium eggshell type catalyst are contacted at a temperature of about 290° C.

13. The method according to claim 9 , wherein the conversion of n-butyraldehyde is at least 70%.

Assignees

• Eastman Chem Co

Inventors

• BOPPANA Venkata Bharat
• Hampton Jr Kenneth Wayne
• Liu Zhufang
• Sumner Jr Charles Edwan
• Tustin Gerald C
• Steinmetz Guy Ralph
• Steffey Melissa Page

Classifications

• B01J37/0236

  Drying, e.g. preparing a suspension, adding a soluble salt and drying · CPC title

• B01J37/16

  Reducing · CPC title

• Y02P20/584

  Recycling of catalysts · CPC title

• B01J21/063

  Titanium; Oxides or hydroxides thereof · CPC title

• C07C45/72 Primary

  by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups · CPC title