# US 11,993,566 B2 · Hydroformylation method

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- Number: US 11,993,566 B2
- Document ID: US11993566B2
- Status: Granted
- Kind: B2
- Application number: 17/641,744
- Filed: 2021-07-26
- Published: 2022-09-29
- Granted: 2024-05-28
- Earliest claimed: 2020-07-30
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Yonghyun Kwon; Hyunseok Nam; Jihoon Kim; Jangkeun Cho; Daeheung Choi
- Web page: https://patentgrep.com/patent/US11993566B2

## CPC

- C07C 45/50: by oxo-reactions
- B01J 31/0204: {Ethers}
- B01J 31/185: {Phosphites ((RO)3P) , their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof}
- B01J 31/20: Carbonyls
- B01J 31/2208: {Oxygen, e.g. acetylacetonates}
- B01J 31/2234: {Beta-dicarbonyl ligands, e.g. acetylacetonates}
- B01J 31/2409: {with more than one complexing phosphine-P atom}
- B01J 2231/321: Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
- B01J 2531/822: Rhodium
- B01J 2531/827: Iridium
- B01J 2531/845: Cobalt
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

A hydroformylation method including preparing an aldehyde by reacting a raw-C5 feed with a synthetic gas in the presence of a catalyst composition.

## Claims

### Claim 1

A hydroformylation method, the method comprising:
reacting a raw-C5 feed with a synthetic gas in the presence of a catalyst composition to produce an aldehyde,
wherein the catalyst composition comprises a phosphorous-based ligand, a transition metal compound of Chemical Formula 1, and a solvent:
[Chemical Formula 11
M(L1)x(L2)y(L3)z [Chemical Formula 1]
wherein in Chemical Formula 1,
M is selected from the group consisting of rhodium (Rh), cobalt (Co), iridium (Ir), ruthenium (Ru), iron (Fe), nickel (Ni), palladium (Pd), platinum (Pt) and osmium (Os);
L1, L2 and L3 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, carbonyl (CO), cyclooctadiene, norbornene, chlorine, triphenylphosphine (TPP) and acetylacetonato (AcAc); and
x, y and z are each independently an integer of 0 to 5, and x, y and z are not 0 at the same time;
wherein the solvent comprises one or more selected from the group consisting of tetraethylene glycol dimethyl ether (TEGDME), 1,2,4-trimethylbenzene and cumene; and
wherein the raw-C5 feed has a total weight ratio of less than 1,000 and the solvent has a total weight ratio of 500 or greater, based on a total weight of the transition metal compound.

### Claim 2 (depends on 1)

The hydroformylation method of claim 1, wherein the raw-C5 feed is a product of a naphtha cracking center (NCC) process, and the raw-C5 feed comprises a mixture of a terminal monoene, an internal monoene and a diene.

### Claim 3 (depends on 2)

The hydroformylation method of claim 2, wherein, an amount of the diene in the raw-C5 feed is 30% by weight or more based on a total weight of the mixture of the terminal monoene, internal monoene and diene.

### Claim 4 (depends on 1)

The hydroformylation method of claim 1, wherein the phosphorous-based ligand comprises one or more selected from the group consisting of 1,2-bis(diphenylphosphino)ethane, 4,5-bis(diphenylphosphino), triphenylphosphine and 6,6′-[(3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy) This(dibenzo[d,f][1,3,2]dioxaphosphephine).

### Claim 5 (depends on 1)

The hydroformylation method of claim 1, wherein the transition metal compound comprises one or more selected from the group consisting of cobalt carbonyl [CO2(CO)8], acetylacetonatodicarbonyl rhodium [Rh(AcAc)(CO)2], acetylacetonatocarbonyl triphenylphosphine rhodium [Rh(AcAc)(CO)(TPP))], hydridocarbonyl tri(triphenylphosphine)rhodium [HRh(C0)(TPP)3], acetylacetonatodicarbonyl iridium [Ir(AcAc)(CO)2], hydridocarbonyl tri(triphenylphosphine)iridium [HIr(CO)(TPP)3] and chloro(1,5-cyclooctadiene)rhodium [Rh(COD)Cl2].

### Claim 6 (depends on 1)

The hydroformylation method of claim 1, wherein the hydroformylation method is carried out at a reaction temperature of 90° C. or higher and a reaction pressure of 15 bar or higher.

### Claim 7 (depends on 1)

The hydroformylation method of claim 1, wherein a molar ratio of the raw-C5 feed to the synthetic gas is from 95:5 to 5:95.

### Claim 8 (depends on 1)

The hydroformylation method of claim 1, wherein the synthetic gas comprises carbon monoxide and hydrogen, in a molar ratio of from 5:95 to 70:30.