Catalyst for reduction reaction of 3,4-dihydroxytetrahydrofuran, and method for producing 3,4-dihydroxytetrahydrofuran reduced product

Patent metadata

Field	Value
Publication number	US-11040334-B2
Application number	US-201716485379-A
Country	US
Kind code	B2
Filing date	Dec 28, 2017
Priority date	Feb 13, 2017
Publication date	Jun 22, 2021
Grant date	Jun 22, 2021

Abstract

Provided is a catalyst for reduction reaction with which 1,4-butanediol or tetrahydrofuran can be obtained with higher selectivity than with the related art, using a raw material derived from biomass. The catalyst is used in a reduction reaction of 3,4-dihydroxytetrahydrofuran with hydrogen, wherein the catalyst contains metal catalysts (1) and (2) below; metal catalyst (1): a catalyst containing M1 and M2 below as metal species and supported on a carrier; and metal catalyst (2): a catalyst containing M1 below as a metal species and supported on a carrier; M1: one or more selected from the group consisting of iron and elements belonging to periods 4 to 6 and groups 5 to 7 of the periodic table; and M2: one or more selected from the group consisting of ruthenium, osmium, and elements belonging to periods 4 to 6 and groups 9 to 11 of the periodic table.

First claim

The invention claimed is:

1. A catalyst for reduction reaction of 3,4-dihydroxytetrahydrofuran, the catalyst being used in a reaction for reducing 3,4-dihydroxytetrahydrofuran by reaction with hydrogen, wherein the catalyst contains a metal catalyst (1) and a metal catalyst (2) below;
metal catalyst (1): a catalyst containing M1 and M2 below as metal species and supported on a carrier; and
metal catalyst (2): a catalyst containing M1 below as a metal species and supported on a carrier;
M1: one or more selected from the group consisting of iron and elements belonging to periods 4 to 6 and belonging to groups 5 to 7 of the periodic table; and
M2: one or more selected from the group consisting of ruthenium, osmium, and elements belonging to periods 4 to 6 and belonging to groups 9 to 11 of the periodic table.

2. The catalyst for reduction reaction of 3,4-dihydroxytetrahydrofuran according to claim 1 , wherein the M1 in the metal catalyst (1) is rhenium and the M2 in the metal catalyst (1) is gold.

3. The catalyst for reduction reaction of 3,4-dihydroxytetrahydrofuran according to claim 1 , wherein the carrier in the metal catalyst (1) is cerium oxide.

4. The catalyst for reduction reaction of 3,4-dihydroxytetrahydrofuran according to claim 1 , wherein the M1 in the metal catalyst (2) is rhenium.

5. The catalyst for reduction reaction of 3,4-dihydroxytetrahydrofuran according to claim 1 , wherein the carrier in the metal catalyst (2) is an activated carbon.

6. A method for producing a 3,4-dihydroxytetrahydrofuran reduced product, the method comprising reducing 3,4-dihydroxytetrahydrofuran by reaction with hydrogen, wherein the reaction of 3,4-dihydroxytetrahydrofuran and hydrogen is allowed to proceed in the presence of the catalyst for reduction reaction of 3,4-dihydroxytetrahydrofuran described in claim 1 .

7. The method for producing a 3,4-dihydroxytetrahydrofuran reduced product according to claim 6 , wherein the reaction of 3,4-dihydroxytetrahydrofuran and hydrogen is performed in an atmosphere with a hydrogen partial pressure of 3 MPa or higher.

8. The method for producing a 3,4-dihydroxytetrahydrofuran reduced product according to claim 6 , the method comprising subjecting erythritol to cyclodehydration to obtain 3,4-dihydroxytetrahydrofuran prior to the reducing 3,4-dihydroxytetrahydrofuran.

9. A catalyst for reduction reaction of 3,4-dihydroxytetrahydrofuran, the catalyst being used in a reaction for reducing 3,4-dihydroxytetrahydrofuran by reaction with hydrogen, wherein the catalyst contains a catalyst (A) and a catalyst (B) below; and at least one of the catalyst (A) and the catalyst (B) are catalysts in which M1 below is supported as a metal species;
catalyst (A): an inorganic oxide; and
catalyst (B): an activated carbon;
M1: one or more selected from the group consisting of iron and elements belonging to periods 4 to 6 and belonging to groups 5 to 7 of the periodic table.

10. The catalyst for reduction reaction of 3,4-dihydroxytetrahydrofuran according to claim 9 , wherein the M1 is rhenium.

11. The catalyst for reduction reaction of 3,4-dihydroxytetrahydrofuran according to claim 9 , wherein the inorganic oxide in the catalyst (A) is cerium oxide.

12. The catalyst for reduction reaction of 3,4-dihydroxytetrahydrofuran according to claim 9 , wherein the catalyst (B) is a catalyst in which the M1 is supported as a metal species.

13. The catalyst for reduction reaction of 3,4-dihydroxytetrahydrofuran according to claim 9 , wherein the catalyst (A) and the catalyst (B) are catalysts in which the M1 is supported as a metal species.

14. A method for producing a 3,4-dihydroxytetrahydrofuran reduced product, the method comprising reducing 3,4-dihydroxytetrahydrofuran by reaction with hydrogen, wherein the reaction of 3,4-dihydroxytetrahydrofuran and hydrogen is allowed to proceed in the presence of the catalyst for reduction reaction of 3,4-dihydroxytetrahydrofuran described in claim 9 .

15. A method for producing a 3,4-dihydroxytetrahydrofuran reduced product, the method comprising reducing 3,4-dihydroxytetrahydrofuran by reaction with hydrogen, wherein the reaction of 3,4-dihydroxytetrahydrofuran and hydrogen is allowed to proceed by performing a reaction in the presence of a metal catalyst (1) below in a first stage and performing a reaction in the presence of a metal catalyst (2) below in a second stage;
metal catalyst (1): a catalyst containing M1 and M2 below as metal species and supported on a carrier; and
metal catalyst (2): a catalyst containing M1 below as a metal species and supported on a carrier;
M1: one or more selected from the group consisting of iron and elements belonging to periods 4 to 6 and belonging to groups 5 to 7 of the periodic table; and
M2: one or more selected from the group consisting of ruthenium, osmium, and elements belonging to periods 4 to 6 and belonging to groups 9 to 11 of the periodic table.

16. A method for producing a 3,4-dihydroxytetrahydrofuran reduced product, the method comprising reducing 3,4-dihydroxytetrahydrofuran by reaction with hydrogen, wherein the reaction of 3,4-dihydroxytetrahydrofuran and hydrogen is allowed to proceed by performing a reaction in the presence of a catalyst (A) below in a first stage and performing a reaction in the presence of a catalyst (B) below in a second stage;
wherein at least one of the catalyst (A) and the catalyst (B) are catalysts in which M1 below is supported as a metal species;
catalyst (A): an inorganic oxide; and
catalyst (B): an activated carbon;
M1: one or more selected from the group consisting of iron and elements belonging to periods 4 to 6 and belonging to groups 5 to 7 of the periodic table.

Assignees

• Daicel Corp

Inventors

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

Classifications

• B01J23/36 Primary

  Rhenium · CPC title

• C07C31/20

  Dihydroxylic alcohols · CPC title

• B01J23/10

  of rare earths · CPC title

• C07C27/04

  by reduction of oxygen-containing compounds (C07C29/14 takes precedence) · CPC title

• B01J23/688 Primary

  with manganese, technetium or rhenium · CPC title