# US 10,766,836 B2 · Methods and systems for separating olefins

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 10,766,836 B2
- Document ID: US10766836B2
- Status: Granted
- Kind: B2
- Application number: 14/210,035
- Filed: 2014-03-13
- Published: 2014-09-18
- Granted: 2020-09-08
- Earliest claimed: 2013-03-14
- Assignees: Kellogg Brown & Root LLC
- Applicants: Kellogg Brown & Root LLC
- Inventors: Vijender Kumar Verma; Curtis Eng
- Web page: https://patentgrep.com/patent/US10766836B2

## CPC

- C07C 7/167: for removal of compounds containing a triple carbon-to-carbon bond
- C07C 7/09: by fractional condensation
- C10G 7/00: Distillation of hydrocarbon oils
- C10G 45/32: Selective hydrogenation of the diolefin or acetylene compounds
- F25J 3/0219: {Refinery gas, cracking gas, coke oven gas, gaseous mixtures containing aliphatic unsaturated CnHm or gaseous mixtures of undefined nature}
- F25J 3/0233: {separation of CnHm with 1 carbon atom or more}
- F25J 3/0238: {separation of CnHm with 2 carbon atoms or more}
- F25J 3/0242: {separation of CnHm with 3 carbon atoms or more}
- F25J 3/0252: {separation of hydrogen (production of hydrogen containing gas in general C01B3/00, e.g. separation of hydrogen or hydrogen containing gases form gaseous mixtures at low temperatures C01B3/506)}
- C10G 2300/1088: Olefins
- C10G 2400/20: C2-C4 olefins
- F25J 2205/04: in the feed line, i.e. upstream of the fractionation step
- F25J 2210/04: Mixing or blending of fluids with the feed stream
- F25J 2210/12: Refinery or petrochemical off-gas
- F25J 2215/62: Ethane or ethylene
- F25J 2230/30: Compression of the feed stream
- F25J 2245/02: Recycle of a stream in general, e.g. a by-pass stream
- Y02P 30/40: Ethylene production
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C10G: CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION (cracking to hydrogen or synthesis gas C01B; cracking or pyrolysis of hydrocarbon gases to individual hydrocarbons or mixtures thereof of definite or specified constitution C07C; cracking to cokes C10B); RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- F25J: LIQUEFACTION, SOLIDIFICATION OR SEPARATION OF GASES OR GASEOUS {OR LIQUEFIED GASEOUS} MIXTURES BY PRESSURE AND COLD TREATMENT {OR BY BRINGING THEM INTO THE SUPERCRITICAL STATE (cryogenic pumps F04B37/08; gas storage vessels, gas holders F17; filing vessels with, or discharging from vessels, compressed, liquefied or solidified gases F17C; refrigeration machines, plants, or systems F25B)}
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Systems and methods for separating one or more olefins are provided. In one or more embodiments, the method for separating one or more olefins can include separating at least a portion of one or more C3 and heavier hydrocarbons from a hydrocarbon containing C1 to C20 hydrocarbons to provide a first mixture that can include methane, ethane, ethylene, and/or acetylene. At least a portion of the first mixture can be hydrogenated to convert at least a portion of the acetylene to ethane and ethylene. At least a portion of the methane can be separated from the hydrogenated mixture to provide a second mixture that can include ethane and ethylene. At least a portion of the ethylene can be separated from the second mixture to provide a first product that can include at least 95 mol % ethylene and a second product that can include at least 95 mol % ethane.

## Claims

### Claim 1

A method for separating one or more olefins comprising:
separating at least a portion of C3 and heavier hydrocarbons from a hydrocarbon comprising C1 to C20 hydrocarbons and hydroogen to provide a first hydrocarbon mixture comprising methane, ethane, ethylene, acetylene, and hydrogen;
hydrogenating at least a portion of the first hydrocarbon mixture to convert at least a portion of the acetylene to ethane and ethylene to provide a hydrogenated mixture, wherein the hydrogenation is performed using contained hydrogen in the first hydrocarbon mixture, optionally supplemented by an external stream with hydrogen concentration of at least 50 mol %;
cooling and condensing the hydrogenated mixture, at a temperature ranging from 5° C. to −40° C.;
separating at least a portion of the methane from the condensed hydrogenated mixture to provide a second hydrocarbon mixture comprising ethane and ethylene; and
separating at least a portion of the ethylene from the second hydrocarbon mixture to provide a first product comprising at least 97 mol % ethylene and a second product comprising at least 97 mol % ethane, wherein the at least a portion of ethylene is separated from the second hydrocarbon mixture using a vapor-liquid separator at a temperature greater than boiling point of propylene, that is greater than about −48° C. and at a pressure of about 360 kPa to about 4,000 kPa, wherein the hydrogenated mixture is cooled using refrigerated propylene.

### Claim 2 (depends on 1)

The method of claim 1, further comprising transferring at least a portion of the second product to a pyrolysis furnace.

### Claim 3 (depends on 1)

The method of claim 1, wherein the at least a portion of C3 and heavier hydrocarbons are separated from the hydrocarbon comprising C1 to C20 hydrocarbons at a pressure of about 400 kPa to about 3,000 kPa.

### Claim 4 (depends on 1)

The method of claim 1, wherein the at least a portion of methane is separated from the condensed hydrogenated mixture at a pressure of about 600 kPa to about 4,200 kPa, and the ethylene is separated from the second hydrocarbon mixture at a pressure of about 500 kPa to about 2,500 kPa.

### Claim 5 (depends on 1)

The method of claim 1, wherein at least a portion of the hydrocarbon comprising C1 to C20 hydrocarbons is produced by cracking a heavy hydrocarbon containing C4+ hydrocarbons in a fluid catalytic cracker, a pyrolytic process, or combination thereof.

### Claim 6 (depends on 1)

The method of claim 1, wherein the at least a portion of C3 and heavier hydrocarbons are separated from the hydrocarbon comprising C1 to C20 hydrocarbons at a pressure of about 800 kPa to about 2,000 kPa, the methane is separated from the condensed, hydrogenated mixture at a pressure of about 900 kPa to about 3,500 kPa, and the ethylene is separated from the second hydrocarbon mixture at a pressure of about 500 kPa to about 2,500 kPa.

### Claim 7 (depends on 1)

The method of claim 1, wherein the at least a portion of the first hydrocarbon mixture is hydrogenated in the presence of a catalyst.

### Claim 8 (depends on 1)

The method of claim 1, wherein a methane concentration in the hydrocarbon comprising C1 to C20 hydrocarbons is less than 12 mol %.

### Claim 9

A method for separating one or more olefins comprising:
compressing a fluid comprising C1-C20 hydrocarbons, water, one or more acid gases, and hydrogen to obtain a compressed fluid;
scrubbing at least a portion of the compressed fluid to remove at least a portion of the one or more acid gases to provide a scrubbed fluid;
separating at least a portion of the water from the scrubbed fluid to provide a dehydrated fluid containing less than 0.5 mol % water, wherein the dehydrated fluid comprises the C1-C20 hydrocarbons and hydrogen;
separating at least a portion of C4 and heavier hydrocarbons from the dehydrated fluid to provide a hydrocarbon comprising C1-C3 hydrocarbons and hydrogen;
separating at least a portion of C3 hydrocarbons from the hydrocarbon comprising C1-C3 hydrocarbons to provide a first hydrocarbon mixture comprising ethane, ethylene, acetylene, methane, and hydrogen, where the hydrogen concentration in the first hydrocarbon mixture is from about 0.1 mol % to less than 15 mol %;
hydrogenating at least a portion of the first hydrocarbon mixture to convert at least a portion of the acetylene to ethane and ethylene to provide a hydrogenated mixture, wherein the hydrogenation is performed using contained hydrogen in the first hydrocarbon mixture, optionally supplemented by an external stream with hydrogen concentration of at least 50 mol %;
cooling and condensing the hydrogenated mixture, at a temperature ranging from 5° C. to −40° C.;
separating at least a portion of the methane from the condensed, hydrogenated mixture to provide a second hydrocarbon mixture comprising ethane and ethylene; and
separating at least a portion of the ethylene from the second hydrocarbon mixture to provide a first product comprising at least 97 mol % ethylene and a second product comprising at least 97 mol % ethane, wherein the at least a portion of ethylene is separated from the second hydrocarbon mixture using a vapor-liquid separator at a temperature greater than boiling point of propylene, that is greater than about −48° C. and at a pressure of about 360 kPa to about 4,000 kPa, wherein the hydrogenated mixture is cooled using refrigerated propylene.

### Claim 10 (depends on 9)

The method of claim 9, further comprising transferring all or a portion of the second product to a pyrolysis furnace.

### Claim 11 (depends on 9)

The method of claim 9, wherein the fluid has a methane concentration of less than 15 mol %.

### Claim 12 (depends on 9)

The method of claim 9, wherein the fluid has a hydrogen concentration of less than 15 mol %.

### Claim 13 (depends on 9)

The method of claim 9, wherein the at least a portion of C4 and heavier hydrocarbons are separated from the dehydrated fluid at a pressure of about 500 kPa to about 3,500 kPa.

### Claim 14 (depends on 9)

The method of claim 9, wherein the at least a portion of C3 hydrocarbons are separated from the hydrocarbon comprising C1-C3 hydrocarbons at a pressure of about 400 kPa to about 3,000 kPa.

### Claim 15 (depends on 9)

The method of claim 9, wherein at least a portion of the C1-C20 hydrocarbons is produced by cracking a heavy hydrocarbon containing C4+ hydrocarbons in a fluid catalytic cracker, a pyrolytic process, or a combination thereof.

### Claim 16 (depends on 9)

The method of claim 9, wherein the at least a portion of C4 and heavier hydrocarbons are separated from the dehydrated fluid at a pressure of about 800 kPa to about 2,000 kPa, the at least a portion of methane is separated from the condensed, hydrogenated mixture at a pressure of about 900 kPa to about 3,500 kPa, and the at least a portion of ethylene is separated from the second hydrocarbon mixture at a pressure of about 500 kPa to about 2,500 kPa.

### Claim 17 (depends on 9)

The method of claim 9, wherein the at least a portion of ethylene is separated from the second hydrocarbon mixture at a pressure of about 500 kPa to about 2,500 kPa.

### Claim 18 (depends on 1)

The method of claim 1, wherein the hydrogenated mixture is cooled using a chilling system, wherein the chilling system includes a first cooler, a first vapor/liquid separator receiving the cooled hydrogenated mixture from the first cooler, and a second cooler receiving a gaseous hydrogenated mixture from the vapor/liquid separator.

### Claim 19 (depends on 18)

The method of claim 18, wherein the first cooler provides a first cooled condensed portion of the hydrogenated mixture, wherein the second cooler includes at least one heat exchanger and a second vapor/liquid separator, and wherein the second vapor/liquid separator provides at least a tail gas and a second cooled condensed portion of the hydrogenated mixture.