Method for producing olefin and olefination reaction catalyst

Patent metadata

Field	Value
Publication number	US-12410109-B2
Application number	US-202118028589-A
Country	US
Kind code	B2
Filing date	Sep 15, 2021
Priority date	Sep 28, 2020
Publication date	Sep 9, 2025
Grant date	Sep 9, 2025

Abstract

Provided is a method capable of producing an olefin with high selectivity and high yield using a vicinal diol as a raw material. A method for producing an olefin includes a step of reacting a compound including two adjacent carbon atoms each containing a hydroxy group with hydrogen and forming an olefin, and in this step, the reaction of the compound including two adjacent carbon atoms each containing a hydroxy group with the hydrogen proceeds in the presence of a catalyst under a condition substantially free of a solvent. The catalyst includes a carrier, at least one oxide supported on the carrier and selected from the group consisting of oxides of group-6 elements and oxides of group-7 elements, and at least one metal supported on the carrier and selected from the group consisting of silver, iridium, and gold.

First claim

The invention claimed is:

1. A method for producing butadiene, the method comprising an olefinating step of reacting erythritol with hydrogen and forming the butadiene, wherein in the olefinating step, a reaction of the erythritol with the hydrogen proceeds in the presence of a catalyst under a condition substantially free of a solvent, wherein the catalyst is ReO X —Au/CeO 2 or ReO X —Ag/CeO 2 .

2. The method for producing butadiene according to claim 1 , wherein the erythritol is a liquid under the condition of the reaction, and the butadiene is a gas under the condition of the reaction.

3. The method for producing butadiene according to claim 1 , wherein the erythritol includes two or more pairs of structures, each structure having two adjacent carbon atoms each containing a hydroxy group, and the butadiene to be produced contains two or more pairs of carbon-carbon double bonds.

4. The method for producing butadiene according to claim 1 , wherein the erythritol includes two or more pairs of structures, each structure having two adjacent carbon atoms each containing a hydroxy group.

5. The method for producing butadiene according to claim 1 , wherein the butadiene to be produced includes 1,3-butadiene.

6. The method for producing butadiene according to claim 1 , wherein in the olefinating step, the butadiene is produced with a selectivity of 70% or greater.

7. The method for producing butadiene according to claim 1 , wherein a reaction time in the olefinating step is from 10 to 60 hours.

8. The method for producing butadiene according to claim 1 , wherein a reaction temperature in the olefinating step is from 50 to 250° C.

9. A catalyst for an olefination reaction, the catalyst, to be used in a reaction of erythritol with hydrogen forming butadiene, comprising a carrier, a film of at least one oxide supported on the carrier and selected from the group consisting of oxides of group-6 elements and oxides of group-7 elements, and a film of at least one metal supported on the carrier and selected from the group consisting of silver and gold,
wherein the at least one oxide supported on the carrier and selected from the group consisting of oxides of group-6 elements and oxides of group-7 elements includes rhenium oxide, and
wherein the carrier includes cerium oxide.

10. The method for producing butadiene according to claim 1 , in which the erythritol includes two pairs of structures, each structure having two adjacent carbon atoms each containing a hydroxy group.

11. The method for producing butadiene according to claim 1 , in which the catalyst includes a film of silver or gold and a film of cerium oxide in this order on a rhenium oxide carrier.

12. The method for producing butadiene according to claim 1 , in which a content ratio of a solvent in a raw material mixture in the olefinating step is 0.1 parts by mass or less based on a total amount (100 parts by mass) of the erythritol.

13. The method for producing butadiene according to claim 1 , in which a content ratio of a solvent in a raw material mixture in the olefinating step is 0.05 parts by mass or less, based on a total amount (100 parts by mass) of the erythritol.

14. The method for producing butadiene according to claim 1 , in which the reaction in the olefinating step proceeds under conditions substantially free of water and an organic solvent.

15. The catalyst for an olefination reaction according to claim 9 , including the film of the metal and the film of the oxide in this order on the carrier.

Assignees

• Daicel Corp

Inventors

• Kajikawa Yasuteru
• Hirai Yuuichirou
• Ono Keisuke
• Tomishige Keiichi
• Nakagawa Yoshinao

Classifications

• C07C2523/68

  with arsenic, antimony, bismuth, vanadium, niobium, tatalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium · CPC title

• C07C2523/10

  of rare earths · CPC title

• B01J23/688

  with manganese, technetium or rhenium · CPC title

• B01J23/10

  of rare earths · CPC title

• C07C2523/52

  Gold · CPC title