# US 10,118,876 B2 · Butadiene extraction process

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

- Number: US 10,118,876 B2
- Document ID: US10118876B2
- Status: Granted
- Kind: B2
- Application number: 15/230,817
- Filed: 2016-08-08
- Published: 2016-11-24
- Granted: 2018-11-06
- Earliest claimed: 2012-10-04
- Assignees: Lummus Technology Inc.
- Applicants: Lummus Technology Inc.
- Inventors: Robert John Brummer; Kevin John Schwint; Thomas Alexander Dwyer
- Web page: https://patentgrep.com/patent/US10118876B2

## CPC

- C07C 7/005: {Processes comprising at least two steps in series}
- B01D 1/30: Accessories for evaporators {; Constructional details thereof}
- B01D 11/0492: {Applications, solvents used}
- C07C 5/09: to carbon-to-carbon double bonds
- C07C 7/10: by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
- C07C 7/167: for removal of compounds containing a triple carbon-to-carbon bond
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)

## Abstract

A process for recovering butadiene from a C4 fraction is disclosed. The process may include: contacting a mixed C4 stream comprising butane, butene, and butadiene, with a solvent comprising an organic solvent and water in a butadiene pre-absorber column to recover an overheads fraction comprising at least a portion of the butane, butene, and water, and a first bottoms fraction comprising the organic solvent, butadiene, and at least a portion of the butene; and feeding the first bottoms fraction to a butadiene extraction unit to recover a butene fraction, a crude butadiene fraction, and a solvent fraction.

## Claims

### Claim 1

A system for recovering 1,3-butadiene from a C4 fraction, comprising:
a feed line for providing a hydrocarbon fraction containing butanes, butenes, 1,2-butadiene, 1,3-butadiene, C4 acetylenes, C3 acetylenes, and C5+ hydrocarbons;
a butadiene extraction unit for receiving at least a portion of the hydrocarbon fraction and separating the hydrocarbon fraction into a 1,3-butadiene fraction, a C3 acetylene fraction, a C4 acetylene fraction, one or more fractions comprising the butanes and butenes, and a fraction comprising 1,2-butadiene and the C5+ hydrocarbons;
a reactor for receiving and selectively hydrogenating at least one of the C3 acetylene fraction and the C4 acetylene fraction to produce a hydrogenated effluent comprising olefins, dienes, and oligomer byproducts;
a separator for receiving the hydrogenated effluent and the fraction comprising the 1,2-butadiene and the C5+ hydrocarbons and to recover a heavies fraction comprising the C5+ hydrocarbons and the oligomer byproducts and a lights fraction comprising the olefins, dienes, and 1,2-butadiene; and
a flow line for feeding the lights fraction to the butadiene extraction unit.

### Claim 2 (depends on 1)

The system of claim 1, wherein the C4 acetylene fraction comprises C4 acetylenes and 1,2-butadiene.

### Claim 3 (depends on 2)

The system of claim 2, further comprising a flow line for feeding the C4 acetylene fraction to the reactor for selectively hydrogenating.

### Claim 4 (depends on 1)

The system of claim 1, wherein the butadiene extraction unit is further configured to recover a vinylcyclohexene fraction.

### Claim 5 (depends on 1)

The system of claim 1, further comprising a vaporization system for vaporizing a portion of the hydrocarbon fraction to produce a vapor fraction a liquid fraction.

### Claim 6 (depends on 1)

The system of claim 1, wherein the butadiene extraction unit comprises one or more of the following:
a pre-absorber;
a pre-fractionation column;
a feed scrubber/stripper system
a main wash column;
a rectifier;
an afterwash column;
an acetylene fractionator;
a butadiene fractionator;
an acetylene washer;
a solvent purification system; or
a degasser and cooling column.

### Claim 7

A system for recovering 1,3-butadiene from a C4 fraction, comprising:
a vaporization system for receiving a hydrocarbon fraction containing butanes, butenes, 1,2-butadiene, 1,3-butadiene, C4 acetylenes, C3 acetylenes, and C5+ hydrocarbons and producing a vapor fraction and a liquid fraction;
a butadiene unit for receiving the vapor fraction and recovering a 1,3-butadiene fraction, a C3 acetylene fraction, a C4 acetylene fraction, one or more fractions comprising the butanes and butenes, and a fraction comprising the 1,2-butadiene and the C5+ hydrocarbons;
a reactor for receiving and selectively hydrogenating at least one of the C3 acetylene fraction and the C4 acetylene fraction to produce a hydrogenated effluent comprising olefins, dienes, and oligomer byproducts;
a separator for receiving the hydrogenated effluent and the fraction comprising the 1,2-butadiene and the C5+ hydrocarbons and to recover a heavies fraction comprising the C5+ hydrocarbons and the oligomer byproducts and a lights fraction comprising the olefins, dienes, and 1,2-butadiene;
a flow line for feeding the liquid fraction to the separator as a reflux; and
a flow line for feeding the lights fraction to the butadiene extraction unit.

### Claim 8 (depends on 7)

The system of claim 7, wherein the butadiene extraction unit is further configured to recover a vinylcyclohexene fraction.

### Claim 9

A system for recovering 1,3-butadiene from a C4 fraction, comprising:
a feed line for providing a hydrocarbon fraction containing butanes, butenes, 1,2-butadiene, 1,3-butadiene, C4 acetylenes, C3 acetylenes, and C5+ hydrocarbons;
a butadiene extraction unit for receiving a portion of the hydrocarbon fraction and separating the hydrocarbon fraction into a 1,3-butadiene fraction, a C3 acetylene fraction, a C4 acetylene fraction, one or more fractions comprising the butanes and butenes, and a fraction comprising 1,2-butadiene and the C5+ hydrocarbons;
a reactor for selectively hydrogenating at least one of the C3 acetylene fraction and the C4 acetylene fraction to produce a hydrogenated effluent comprising olefins, dienes, and oligomer byproducts;
a separator for receiving the hydrogenated effluent and the fraction comprising the 1,2-butadiene and the C5+ hydrocarbons and to recover a heavies fraction comprising the C5+ hydrocarbons and the oligomer byproducts and a lights fraction comprising the olefins, dienes, and 1,2-butadiene, wherein the separator is configured to receive a remaining portion of the hydrocarbon fraction as a reflux; and
a flow line for feeding the light fraction to the butadiene extraction unit.

### Claim 10 (depends on 9)

The system of claim 9, wherein the C4 acetylene fraction comprises C4 acetylenes and 1,2-butadiene, the system further comprising a flow line for feeding the C4 acetylene fraction to the reactor for selectively hydrogenating.

### Claim 11 (depends on 9)

The system of claim 9, wherein the butadiene extraction unit is further configured to recover a vinylcyclohexene fraction, the system further comprising a flow line for feeding the vinylcyclohexene fraction to the separator, configured to recover the vinylcyclohexene in the heavies fraction.

### Claim 12

A system for recovering 1,3-butadiene from a C4 fraction, comprising:
a feed line for providing a hydrocarbon fraction containing butanes, butenes, 1,2-butadiene, 1,3-butadiene, C4 acetylenes, C3 acetylenes, and C5+ hydrocarbons;
a butadiene extraction unit for receiving at least a portion of the hydrocarbon fraction and separating the hydrocarbon fraction into a 1,3-butadiene fraction, a C3 acetylene fraction, a C4 acetylene fraction, one or more fractions comprising the butanes and butenes, a vinylcyclohexene fraction, and a fraction comprising 1,2-butadiene and the C5+ hydrocarbons;
a reactor for selectively hydrogenating at least one of the C3 acetylene fraction and the C4 acetylene fraction to produce a hydrogenated effluent comprising olefins, dienes, and oligomer byproducts;
a separator for receiving the hydrogenated effluent, the vinylcyclohexene fraction, and the fraction comprising the 1,2-butadiene and the C5+ hydrocarbons and to recover a heavies fraction, comprising the C5+ hydrocarbons, the vinylcyclohexene, and the oligomer byproducts, and a lights fraction, comprising the olefins, dienes, and 1,2-butadiene; and
a flow line for feeding the lights fraction to the butadiene extraction unit.

### Claim 13

A system for recovering 1,3-butadiene from a C4 fraction, comprising:
a feed line for providing a hydrocarbon fraction containing butanes, butenes, 1,2-butadiene, 1,3-butadiene, C4 acetylenes, C3 acetylenes, and C5+ hydrocarbons;
a butadiene extraction unit for receiving at least a portion of the hydrocarbon fraction and separating the hydrocarbon fraction into a 1,3-butadiene fraction, a C3 acetylene fraction, a C4 acetylene fraction, one or more fractions comprising the butanes and butenes, and a fraction comprising 1,2-butadiene and the C5+ hydrocarbons;
a reactor for selectively hydrogenating at least one of the C3 acetylene fraction and the C4 acetylene fraction to produce a hydrogenated effluent comprising olefins, dienes, and oligomer byproducts;
a separator for receiving the hydrogenated effluent and the fraction comprising the 1,2-butadiene and the C5+ hydrocarbons and to recover a heavies fraction comprising the C5+ hydrocarbons and the oligomer byproducts and a lights fraction comprising the olefins, dienes, and 1,2-butadiene;
a flow line for feeding the lights fraction to the butadiene extraction unit; and
a flow line for feeding at least a portion of the hydrocarbon fraction to the separator as a reflux.

### Claim 14 (depends on 13)

The system of claim 13, wherein the separator is configured to operate where the reflux comprises only the hydrocarbon fraction or a portion thereof.

### Claim 15

A system for recovering 1,3-butadiene from a C4 fraction, comprising:
a feed line for providing a hydrocarbon fraction containing butanes, butenes, 1,2-butadiene, 1,3-butadiene, C4 acetylenes, C3 acetylenes, and C5+ hydrocarbons;
a butadiene extraction unit for receiving at least a portion of the hydrocarbon fraction and separating the hydrocarbon fraction into a 1,3-butadiene fraction, a C3 acetylene fraction, a C4 acetylene fraction, one or more fractions comprising the butanes and butenes, and a fraction comprising 1,2-butadiene and the C5+ hydrocarbons;
a reactor for selectively hydrogenating at least one of the C3 acetylene fraction and the C4 acetylene fraction to produce a hydrogenated effluent comprising olefins, dienes, and oligomer byproducts;
a separator for receiving the hydrogenated effluent and the fraction comprising the 1,2-butadiene and the C5+ hydrocarbons and to recover a heavies fraction comprising the C5+ hydrocarbons and the oligomer byproducts and a lights fraction comprising the olefins, dienes, and 1,2-butadiene;
a flow line for feeding the lights fraction to the butadiene extraction unit;
a vaporization system for vaporizing a portion of the hydrocarbon fraction to produce a vapor fraction and a liquid fraction; and
a flow line for feeding the liquid fraction to the separator as a reflux.

### Claim 16

A system for recovering 1,3-butadiene from a C4 fraction, comprising:
a vaporization system for receiving a hydrocarbon fraction containing butanes, butenes, 1,2-butadiene, 1,3-butadiene, C4 acetylenes, C3 acetylenes, and C5+ hydrocarbons and producing a vapor fraction and a liquid fraction;
a butadiene unit for receiving the vapor fraction and recovering a 1,3-butadiene fraction, a C3 acetylene fraction, a C4 acetylene fraction, a vinylcyclohexene fraction, one or more fractions comprising the butanes and butenes, and a fraction comprising the 1,2-butadiene and the C5+ hydrocarbons;
a reactor for selectively hydrogenating at least one of the C3 acetylene fraction and the C4 acetylene fraction to produce a hydrogenated effluent comprising olefins, dienes, and oligomer byproducts;
a separator for receiving the hydrogenated effluent, the vinylcyclohexene fraction, and the fraction comprising the 1,2-butadiene and the C5+ hydrocarbons and to recover a heavies fraction, comprising the C5+ hydrocarbons, the vinylcyclohexene, and the oligomer byproducts, and a lights fraction, comprising the olefins, dienes, and 1,2-butadiene;
a flow line for feeding the liquid fraction to the separator as a reflux; and
a flow line for feeding the lights fraction to the butadiene extraction unit.