# US 11,306,044 B2 · Removing oxygen from ODH process by injecting alcohol

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- Number: US 11,306,044 B2
- Document ID: US11306044B2
- Status: Granted
- Kind: B2
- Application number: 17/316,556
- Filed: 2021-05-10
- Published: 2021-10-07
- Granted: 2022-04-19
- Earliest claimed: 2018-10-19
- Assignees: NOVA Chemicals (International) S.A.
- Applicants: NOVA Chemicals (International) S.A.
- Inventors: Bolaji Olayiwola; Vasily Simanzhenkov; Shahin Goodarznia; Mohamed Aiffa
- Web page: https://patentgrep.com/patent/US11306044B2

## CPC

- C07C 5/48: with oxygen as an acceptor
- B01J 23/002: {Mixed oxides other than spinels, e.g. perovskite}
- B01J 23/28: Molybdenum
- B01J 23/6482: {Vanadium}
- B01J 23/6484: {Niobium}
- B01J 23/755: Nickel
- C07C 7/14891: {alcohols}
- C07C 2523/20: Vanadium, niobium or tantalum
- C07C 2523/22: Vanadium
- C07C 2523/28: Molybdenum
- C07C 2527/057: Selenium or tellurium; Compounds thereof
- Y02P 20/52: using catalysts, e.g. selective catalysts
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Provided in this disclosure is a process for the oxidative dehydrogenation of a lower alkane into a corresponding alkene. The process includes providing a gas stream comprising the lower alkane to a reactor; contacting, in the oxidative dehydrogenation reactor, the lower alkane with a catalyst that includes a mixed metal oxide; and providing to the last 50% of the oxidative dehydrogenation reactor a stream comprising from 0.01 vol. % to 10 vol. % of a C1-C3 alcohol.

## Claims

### Claim 1

A process for the oxidative dehydrogenation of a lower alkane into a corresponding alkene, the process comprising:
providing a gas stream comprising the lower alkane and oxygen to an oxidative dehydrogenation reactor;
contacting, in the oxidative dehydrogenation reactor, the lower alkane with an oxidative dehydrogenation catalyst comprising a mixed metal oxide;
providing a stream comprising from 0.01 vol. % to 10 vol. % of a C1-C3 alcohol to the oxidative dehydrogenation reactor within the last 50% of the total reaction zone in the oxidative dehydrogenation reactor; and obtaining an effluent comprising the corresponding alkene.

### Claim 2 (depends on 1)

The process of claim 1, wherein the stream comprising the C1-C3 alcohol further comprises an inert gas.

### Claim 3 (depends on 1)

The process of claim 1, wherein the effluent comprises less than 100 parts per million by volume (ppmv) O2.

### Claim 4 (depends on 1)

The process of claim 1, wherein the stream comprising the C1-C3 alcohol is provided to the oxidative dehydrogenation reactor within the last 30% of the total reaction zone in the oxidative dehydrogenation reactor.

### Claim 5 (depends on 1)

The process of claim 1, wherein the stream comprising the C1-C3 alcohol is provided to the oxidative dehydrogenation reactor within the last 10% of the total reaction zone in the oxidative dehydrogenation reactor.

### Claim 6 (depends on 1)

The process of claim 1, wherein the oxidative dehydrogenation catalyst comprises a mixed metal oxide selected from the group consisting of:
(i) a catalyst of the formula:
MoaVbTecNbdPdeOf
wherein a is 1, b is from 0.01 to 1.0, c is from 0.01 to 1.0, d is from 0.01 to 1.0, e is from 0.00 to 0.10, and f is a number to satisfy the valence state of the catalyst;
(ii) a catalyst of the formula:
NigAhBiDj Of
wherein:
A is selected from the group consisting of Ti, Ta, V, Nb, Hf, W, Y, Zn, Zr, Si and Al or mixtures thereof;
Bis selected from the group consisting of La, Ce, Pr, Nd, Sm, Sb, Sn, Bi, Pb, Tl, In, Te, Cr, Mn, Mo, Fe, Co, Cu, Ru, Rh, Pd, Pt, Ag, Cd, Os, Ir, Au, Hg, or a mixture thereof;
D is selected from the group consisting of Ca, K, Mg, Li, Na, Sr, Ba, Cs, and Rb or a mixture thereof; and
O is oxygen; and
g is from 0.1 to 0.9, h is from 0.04 to 0.9; i is from 0 to 0.5; j is from 0 to 0.5; and, f is a number to satisfy the valence state of the catalyst;
(iii) a catalyst of the formula:
MOaEkGlOf
wherein:
E is selected from the group consisting of Ba, Ca, Cr, Mn, Nb, Ta, Ti, Te, V, W or a mixture thereof;
G is selected from the group consisting of Bi, Ce, Co, Cu, Fe, K, Mg, V, Ni, P, Pb, Sb, Si, Sn, Ti, U, or a mixture thereof;
a is 1; k is from 0 to 2; I is from 0 to 2, with the proviso that the total value of I for Co, Ni, Fe or a mixture thereof is less than 0.5; and f is a number to satisfy the valence state of the catalyst;
(iv) a catalyst of the formula:
VmMonNbpTeqMerOf
wherein:
Me is a metal selected from the group consisting of Ta, Ti, W, Hf, Zr, Sb or a mixture thereof;
m is from 0.1 to 3; n is from 0.5 to 1.5; p is from 0.001 to 3; q is from 0.001 to 5; r is from 0 to 2; and f is a number to satisfy the valence state of the catalyst; and
(v) a catalyst of the formula:
MoaVrXsYtZuMvOr
wherein:
X is Nb, Ta, or a mixture
thereof; Y is Sb, Ni, or a
mixture thereof;
Z is Te, Ga, Pd, W, Bi, Al, or a mixture thereof;
M is Fe, Co, Cu, Cr, Ti, Ce, Zr, Mn, Pb, Mg, Sn, Pt, Si, La, K, Ag, In, or a mixture thereof;
a is 1; r is from 0.05 to 1.0; s is from 0.001 to 1.0; t is from 0.001 to 1.0; u is from 0.001 to 0.5; v is from 0.001 to 0.3; and f is a number to satisfy the valence state of the catalyst.

### Claim 7 (depends on 1)

The process of claim 1, wherein the lower alkane is a C1-C3 alkane.

### Claim 8 (depends on 1)

The process of claim 1, wherein the lower alkane is ethane.

### Claim 9 (depends on 1)

The process of claim 1, wherein the effluent comprises a carboxylicacid carboxylic acid.

### Claim 10 (depends on 1)

The process of claim 1, wherein the C1-C3 alcohol comprises ethanol.

### Claim 11 (depends on 1)

The process of claim 1, wherein the effluent comprises acetic acid.

### Claim 12 (depends on 1)

The process of claim 1, wherein the process comprises two or more oxidative dehydrogenation reactors.

### Claim 13 (depends on 1)

The process of claim 1, wherein the C1-C3 alcohol is at a concentration of 0.05 vol. % to 2 vol. %.