# US 11,077,428 B2 · Hydrogenolysis catalysts with high acid tolerance

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- Number: US 11,077,428 B2
- Document ID: US11077428B2
- Status: Granted
- Kind: B2
- Application number: 16/511,289
- Filed: 2019-07-15
- Published: 2019-11-07
- Granted: 2021-08-03
- Earliest claimed: 2015-03-26
- Assignees: BASF SE
- Applicants: BASF Corporation
- Inventors: Deepak S. Thakur; William O. Tuttle; Arunabha Kundu; Keenan Lee Deutsch; Jeffrey Baciak
- Web page: https://patentgrep.com/patent/US11077428B2

## CPC

- B01J 23/002: {Mixed oxides other than spinels, e.g. perovskite}
- B01J 21/14: Silica and magnesia
- B01J 23/72: Copper
- B01J 23/80: with zinc, cadmium or mercury
- B01J 23/8892: {Manganese}
- B01J 35/32: Bulk density
- B01J 35/37: Crush or impact strength
- B01J 35/394: {Metal dispersion value, e.g. percentage or fraction}
- B01J 35/613: {10-100 m2/g}
- B01J 35/633: {less than 0.5 ml/g}
- B01J 35/635: {0.5-1.0 ml/g}
- B01J 37/0018: {Addition of a binding agent or of material, later completely removed among others as result of heat treatment, leaching or washing,(e.g. forming of pores; protective layer, desintegrating by heat)}
- B01J 37/04: Mixing {(B01J37/0009, B01J37/0018 take precedence)}
- B01J 37/08: Heat treatment {(B01J37/0009, B01J37/0018 take precedence)}
- C07C 29/149: with hydrogen or hydrogen-containing gases
- B01J 23/70: of the iron group metals or copper
- B01J 2231/60: Reduction reactions, e.g. hydrogenation
- B01J 2523/00: Constitutive chemical elements of heterogeneous catalysts
- B01J 2523/23: Calcium
- B01J 2523/27: Zinc
- B01J 2523/72: Manganese
- B01J 2523/845: Cobalt
- B01J 2523/847: Nickel
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A catalyst includes a mixed metal oxide; an alumina; silica, and calcium, where the mixed metal oxide includes Cu and at least one of Mn, Zn, Ni, or Co. Such catalysts exhibit enhanced tolerance sulfur-containing compounds and free fatty acids.

## Claims

### Claim 1

A catalyst comprising:
a mixed metal oxide comprising Cu and Mn;
an alumina;
silica; and
calcium;
wherein the catalyst comprises about 2 wt % to about 10 wt % Mn.

### Claim 2 (depends on 1)

The catalyst of claim 1, wherein the catalyst comprises a surface, and wherein the percent of Cu at the surface in relation to total Cu content of the catalyst is from about 0.5% to about 20%.

### Claim 3 (depends on 1)

The catalyst of claim 1, wherein the catalyst comprises about 15 wt % to about 50 wt % Cu.

### Claim 4 (depends on 1)

The catalyst of claim 1, wherein the mixed metal oxide further comprises Zn, and wherein the catalyst comprises about 15 wt % to about 50 wt % Zn.

### Claim 5 (depends on 1)

The catalyst of claim 1, wherein the alumina is present in the catalyst at about 10 wt % to about 30 wt %.

### Claim 6 (depends on 1)

The catalyst of claim 1, wherein the silica is present in the catalyst at about 10 wt % to about 30 wt %.

### Claim 7 (depends on 1)

The catalyst of claim 1, wherein the calcium is present in the catalyst at about 2 wt % to about 10 wt %.

### Claim 8 (depends on 1)

The catalyst of claim 1, wherein the catalyst comprises 0.5 wt % or less of sodium, chromium, barium, or a combination of two or more thereof.

### Claim 9 (depends on 1)

The catalyst of claim 1, wherein the catalyst has a Brunauer-Emmett-Teller surface area from about 10 m2/g to about 150 m2/g.

### Claim 10 (depends on 1)

The catalyst of claim 1, wherein the catalyst has a mercury pore volume from about 0.10 cm3/g to about 0.80 cm3/g.

### Claim 11 (depends on 1)

The catalyst of claim 1, wherein the catalyst has a packed ambient bulk density from about 0.3 g/cm3 to about 1.6 g/cm3.

### Claim 12 (depends on 1)

The catalyst of claim 1, wherein the catalyst has a side crush strength from about 2.5 lbs/mm to about 12 lbs/mm.

### Claim 13 (depends on 1)

A method of making the catalyst of claim 1, the method comprising calcining a shaped material;
wherein:
the shaped material is formed by shaping a paste, the paste comprising:
a mixed metal oxide comprising Cu and Mn;
an alumina;
a silica sol; and
calcium hydroxide.

### Claim 14 (depends on 1)

A process comprising
hydrogenation and/or hydrogenolysis of a feedstock by contacting the feedstock and H2 with the catalyst of claim 1,
wherein the feedstock comprises at least one carbonyl group.

### Claim 15 (depends on 14)

The process of claim 14, wherein the feedstock comprises fatty acid methyl esters.