Method for regenerating hydrogenation catalyst

Patent metadata

Field	Value
Publication number	US-2022072518-A1
Application number	US-201917417376-A
Country	US
Kind code	A1
Filing date	Dec 30, 2019
Priority date	Dec 28, 2018
Publication date	Mar 10, 2022
Grant date	—

Abstract

The present invention relates to a method for regenerating a dicarboxylic acid or carboxylic acid hydrogenation catalyst, and more particularly, to a method for regenerating a hydrogenation catalyst to be used in a reaction of converting a dicarboxylic acid group into a diol group. The present invention provides an effect of regenerating a catalyst deactivated by the deposition of esters to be produced in a reaction of converting a dicarboxylic acid group into a diol group.

First claim

1 . A method for regenerating a catalyst used in a hydrogenation reaction of carboxylic acid or carboxylic acid ester, the method comprising the steps of:
(a) adding a used catalyst to an organic solvent and washing the catalyst while stirring the catalyst; (b) separating and recovering the catalyst by filtering after the washing; and (c) drying and reactivating the separated and recovered catalyst.

2 . A method for regenerating a catalyst used in a hydrogenation reaction of carboxylic acid or carboxylic acid ester, the method comprising the steps of:
(i) adding a used catalyst and a solvent to a reactor; (ii) replacing a composition of gas inside the reactor with hydrogen; and (iii) reactivating the catalyst by performing a hydrothermal hydrogenation reaction while stirring under a condition in which a reactor internal temperature is 100-400° C. and a hydrogen gas pressure is 1-20 Mpa.

3 . The method of claim 1 , wherein the organic solvent includes at least one selected from the group consisting of acetone, pyridine, hexafluoroisopropanol, methanol, ethanol, propanol, butanol, cyclohexane, toluene, and dichloromethane.

4 . The method of claim 1 , wherein the step (a) of washing the catalyst while stirring the catalyst is performed at 0-150° C. for 0.15-12 hours.

5 . The method of claim 1 , wherein the drying in the step (c) is performed at a temperature of 40-200° C.

6 . The method of claim 2 , wherein the solvent in the step (i) includes at least one selected from water, carboxylic acid, alcohol, and carboxylic acid ester.

7 . The method of claim 6 , wherein, based on 100 parts by weight of the solvent, water is included in an amount of 50-100 parts by weight and at least one of carboxylic acid, alcohol, and carboxylic acid ester is included in an amount of 0-50 parts by weight.

8 . The method of claim 2 , wherein the hydrothermal hydrogenation reaction in the step (iii) is performed for 0.5-48 hours.

9 . The method of claim 1 , wherein the hydrogenation reaction converts a dicarboxylic acid group into a diol group.

10 . The method of claim 1 , wherein the carboxylic acid functional group includes one selected from the group consisting of oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, phthalic acid, isopthalic acid, cyclohexane dicarboxylic acid, and terephthalic acid.

11 . The method of claim 1 , wherein the activity of the used catalyst is lowered by fouling caused by deposition of a material produced in a process of converting a dicarboxylic acid group into a diol group.

12 . The method of claim 11 , wherein the produced material includes ester.

13 . The method of claim 1 , wherein the catalyst includes a precious metal-transition metal supported on a support.

14 . The method of claim 13 , wherein the precious metal includes at least one selected from the group consisting of palladium (Pd), rhodium (Rh), ruthenium (Ru), iridium (Ir), and platinum (Pt), and
the transition metal includes at least one selected from the group consisting of tin (Sn), iron (Fe), rhenium (Re), and gallium (Ga).

15 . The method of claim 13 , wherein the support includes at least one selected from silica, alumina, zirconia, titania, and carbon.

16 . The method of claim 15 , wherein the carbon is at least one selected from the group consisting of activated carbon, carbon black, graphite, graphene, ordered mesoporous carbon (OMC), and carbon nanotubes.

Assignees

• Hanwha Solutions Corp

Inventors

• Yook Sun Woo
• Kim Jeong Kwon
• Jeon Bong Sik
• Myeong Wan Jae

Classifications

• B01J38/58 Primary

  and gas addition thereto · CPC title

• C07C29/147

  of carboxylic acids or derivatives thereof · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• B01J38/10

  using elemental hydrogen · CPC title

• B01J23/626

  with tin · CPC title