IP Library Granted Patent US 10,752,567
Granted Patent B2
US 10,752,567 · App. 16/336,140 · Granted Aug 25, 2020

Method for acid treatment conditioning of a catalyst in the production of glycols

Inventors: Duraisamy Muthusamy (Houston, TX); Viet Quoc Nguyen (Houston, TX)
Assignee: Shell Oil Company
C07C29/132B01J25/02B01J31/04C07C31/202
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Quick Facts
Patent No.
US 10,752,567
App. No.
16/336,140
Granted
Aug 25, 2020
Kind
B2
Abstract

Implementations of the disclosed subject matter provide methods for producing ethylene glycol from a carbohydrate feed which may include conditioning a heterogeneous hydrogenation catalyst by treatment with a protic acid resulting in an acid-conditioned heterogeneous hydrogenation catalyst. Next, in a reactor under hydrogenation conditions, the carbohydrate feed may be contacted with a bi-functional catalyst system comprising the acid-conditioned heterogeneous hydrogenation catalyst, and a soluble retro-Aldol catalyst. An intermediate product stream may be obtained from the reactor including ethylene glycol.

Claims (16)

1. A method for producing ethylene glycol from a carbohydrate feed comprising:

a) conditioning a heterogeneous hydrogenation catalyst by treatment with a protic acid for a first period of time resulting in an acid-conditioned heterogeneous hydrogenation catalyst;

b) next, in a first reactor under hydrogenation conditions, the carbohydrate feed is contacted for a second period of time, with the carbohydrate feed with a bi-functional catalyst system comprising:

1) the acid-conditioned heterogeneous hydrogenation catalyst, and

2) a soluble retro-Aldol catalyst;

c) obtaining an intermediate product stream, from the first reactor, comprising ethylene glycol,

wherein the second period of time follows the first period of time.

2. The method of claim 1 , wherein the protic acid is at least one selected from the group consisting of: organic acid, mineral acid, and combinations thereof.

3. The method of claim 2 , wherein the organic acid is at least one selected from the group consisting of: formic acid, acetic acid, propionic acid, butyric acid, glycolic acid, lactic acid, citric acid, benzoic acid, and combinations thereof.

4. The method of claim 3 , wherein the organic acid is at least one selected from the group consisting of: lactic acid, glycolic acid, and combinations thereof.

5. The method of claim 2 , wherein the mineral acid is at least one selected from the group consisting of: HCl, H 2 SO 4 , H 3 PO 4 , benzene sulfonic acid and combinations thereof.

6. The method of claim 1 , wherein the conditioning step (a) is carried out with a concentration of protic acid in the range of from 0.001 wt % to 50 wt %.

7. The method of claim 1 , wherein the conditioning step (a) is carried out with an acid solution solvent selected from the group consisting of: H 2 O, alcohol, and combinations thereof.

8. The method of claim 1 , wherein the heterogeneous hydrogenation catalyst comprises at least one selected from the group consisting of: Raney-Ni, Raney-Co, Raney-Cu, Raney-Ru, Ni, Co, Cu, Cu—Zn, Cu—Cr, Ni—Mo, Ni—W, and Ni—Cr.

9. The method of claim 1 , wherein the heterogeneous hydrogenation catalyst is further promoted with one or more selected from the group consisting of: Al, Fe, Cr, Mn, Co, Cu, Mo, Ru, Rh, Pd, Ag, W, Re, Ir, Pt, Au, In, Sn, Sb, and Pb.

10. The method of claim 1 , wherein the heterogeneous hydrogenation catalyst comprises Raney-Ni.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 21, 2025
From: SHELL OIL COMPANY
To: TECHNIP ENERGIES FRANCE
Reel/Frame 072620/0036 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 21, 2025
From: SHELL OIL COMPANY
To: TECHNIP ENERGIES FRANCE
Reel/Frame 072620/0308 →
CHANGE OF NAME Recorded Mar 7, 2022
From: SHELL OIL COMPANY
To: SHELL USA, INC.
Reel/Frame 059694/0819 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 8, 2021
From: MUTHUSAMY, DURAISAMY; NGUYEN, VIET QUOC
To: SHELL OIL COMPANY
Reel/Frame 057412/0645 →