# US 2019/0375697 A1 · Hydrocarbon production method and production apparatus

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- Number: US 2019/0375697 A1
- Document ID: US20190375697A1
- Status: Published application
- Kind: A1
- Application number: 16/487,100
- Filed: 2018-02-21
- Published: 2019-12-12
- Earliest claimed: 2017-03-08
- Assignees: Zeon Corporation
- Applicants: Zeon Corporation
- Inventors: Hideaki MIKI
- Web page: https://patentgrep.com/patent/US20190375697A1

## CPC

- C07C 2/50: Diels-Alder conversion
- C07C 5/333: Catalytic processes
- B01D 3/143: {by two or more of a fractionation, separation or rectification step}
- B01D 3/40: Extractive distillation
- B01J 19/245: {placed in series}
- C07C 2/52: Catalytic processes
- C07C 5/03: of non-aromatic carbon-to-carbon double bonds
- C07C 5/3332: {with metal oxides or metal sulfides}
- C07C 5/48: with oxygen as an acceptor
- C07C 7/005: {Processes comprising at least two steps in series}
- C07C 7/04: by distillation
- C07C 7/08: by extractive distillation
- C07B 61/00: Other general methods
- C07C 2521/04: Alumina
- C07C 2521/06: Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- C07C 2523/04: Alkali metals
- C07C 2523/28: Molybdenum
- C07C 2523/42: Platinum
- C07C 2523/44: Palladium
- C07C 2523/62: with gallium, indium, thallium, germanium, tin or lead
- C07C 2523/72: Copper
- C07C 2523/89: combined with noble metals
- C07C 2603/68: Dicyclopentadienes; Hydrogenated dicyclopentadienes
- 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)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

A hydrocarbon production method for producing hydrocarbons from a hydrocarbon mixture includes: a first extractive distillation step of performing extractive distillation of an extractive distillation target to obtain a fraction (A) in which isoprene and piperylene are enriched and a fraction (B) in which a linear hydrocarbon and a branched hydrocarbon are enriched; a first distillation step of obtaining a fraction (C) in which isoprene is enriched and a fraction (D) in which piperylene is enriched from the fraction (A); a dehydrogenation step of performing dehydrogenation or oxidative dehydrogenation of either or both of the linear hydrocarbon and the branched hydrocarbon contained in the fraction (B) to obtain a dehydrogenated product; and a recovery step of supplying the dehydrogenated product to an extractive distillation column or a distillation column and obtaining isoprene and/or piperylene from the dehydrogenated product.

## Claims

### Claim 1

A hydrocarbon production method for producing hydrocarbons from a hydrocarbon mixture containing isoprene, piperylene, a linear hydrocarbon having a carbon number of 5 and including one or fewer carbon-carbon double bonds, and a branched hydrocarbon having a carbon number of 5 and including one or fewer carbon-carbon double bonds, comprising:
a first extractive distillation step of using a first extractive distillation column to perform extractive distillation of an extractive distillation target including the hydrocarbon mixture or a pretreated hydrocarbon mixture resulting from pretreatment of the hydrocarbon mixture to obtain a fraction (A) in which isoprene and piperylene are enriched and a fraction (B) in which the linear hydrocarbon and the branched hydrocarbon, having lower solubility than isoprene and piperylene in an extractant used in the extractive distillation, are enriched;
a first distillation step of using a first distillation column to perform distillation of a fraction obtained after separation of the extractant from the fraction (A) to obtain a fraction (C) in which isoprene is enriched and a fraction (D) in which piperylene is enriched;
a dehydrogenation step of performing dehydrogenation or oxidative dehydrogenation of either or both of the linear hydrocarbon and the branched hydrocarbon contained in the fraction (B) to obtain a dehydrogenated product including either or both of a linear hydrocarbon dehydrogenated product containing piperylene and a branched hydrocarbon dehydrogenated product containing isoprene; and
a recovery step of supplying the dehydrogenated product to an extractive distillation column or a distillation column and obtaining either or both of isoprene and piperylene from the dehydrogenated product.

### Claim 2 (depends on 1)

The hydrocarbon production method according to claim 1, wherein the dehydrogenated product is supplied to the first extractive distillation column in the recovery step.

### Claim 3 (depends on 1)

The hydrocarbon production method according to claim 1, wherein the dehydrogenation step includes: a step of separating the linear hydrocarbon and the branched hydrocarbon contained in the fraction (B); and a step of performing dehydrogenation or oxidative dehydrogenation of either or both of the linear hydrocarbon and the branched hydrocarbon that have been separated.

### Claim 4 (depends on 3)

The hydrocarbon production method according to claim 3, further comprising a step of determining a required production amount of isoprene and piperylene, wherein
an amount of either or both of the linear hydrocarbon and the branched hydrocarbon that is dehydrogenated or oxidatively dehydrogenated in the dehydrogenation step is adjusted in accordance with the required production amount that is determined.

### Claim 5 (depends on 1)

The hydrocarbon production method according to claim 1, wherein
the hydrocarbon mixture further contains cyclopentadiene,
the extractive distillation target includes the pretreated hydrocarbon mixture, and
the pretreatment includes: a step of dimerizing cyclopentadiene in the hydrocarbon mixture to obtain a hydrocarbon mixture containing dicyclopentadiene; and a step of using a predistillation column to perform distillation of the hydrocarbon mixture containing dicyclopentadiene to obtain the pretreated hydrocarbon mixture and a fraction (E) in which dicyclopentadiene is enriched.

### Claim 6 (depends on 5)

The hydrocarbon production method according to claim 5, further comprising:
an isoprene purification step of purifying the fraction (C) in an isoprene purification section including a second extractive distillation column to obtain high-purity isoprene;
a piperylene purification step of purifying the fraction (D) in a piperylene purification section to obtain high-purity piperylene;
a dicyclopentadiene purification step of purifying the fraction (E) in a dicyclopentadiene purification section to obtain high-purity dicyclopentadiene; and
a hydrogenation step of hydrogenating at least one of a residue discharged in the isoprene purification step, a residue discharged in the piperylene purification step, and a residue discharged in the dicyclopentadiene purification step.

### Claim 7 (depends on 6)

The hydrocarbon production method according to claim 6, wherein
either or both of the linear hydrocarbon and the branched hydrocarbon are dehydrogenated in the dehydrogenation step, and
residue hydrogenation in the hydrogenation step is performed using hydrogen produced in dehydrogenation of either or both of the linear hydrocarbon and the branched hydrocarbon in the dehydrogenation step.

### Claim 8

A hydrocarbon production apparatus for producing hydrocarbons from a hydrocarbon mixture containing isoprene, piperylene, a linear hydrocarbon having a carbon number of 5 and including one or fewer carbon-carbon double bonds, and a branched hydrocarbon having a carbon number of 5 and including one or fewer carbon-carbon double bonds, comprising:
a first extractive distillation column that performs extractive distillation of an extractive distillation target including the hydrocarbon mixture or a pretreated hydrocarbon mixture resulting from pretreatment of the hydrocarbon mixture;
a stripping column that separates an extractant from a fraction (A) that flows out from the bottom of the first extractive distillation column;
a first distillation column that performs distillation of a fraction obtained by separating the extractant from the fraction (A) in the stripping column;
a dehydrogenation section that performs dehydrogenation or oxidative dehydrogenation of at least a portion of a fraction (B) that flows out from the top of the first extractive distillation column to obtain a dehydrogenated product; and
a dehydrogenated product line that supplies the dehydrogenated product obtained in the dehydrogenation section to an extractive distillation column or a distillation column.

### Claim 9 (depends on 8)

The hydrocarbon production apparatus according to claim 8, wherein the dehydrogenated product line supplies the dehydrogenated product to the first extractive distillation column.

### Claim 10 (depends on 8)

The hydrocarbon production apparatus according to claim 8, wherein the dehydrogenation section includes a separator that is capable of separating the linear hydrocarbon and the branched hydrocarbon, and a dehydrogenator that performs dehydrogenation or oxidative dehydrogenation of either or both of the linear hydrocarbon and the branched hydrocarbon that are separated in the separator.

### Claim 11 (depends on 8)

The hydrocarbon production apparatus according to claim 8, wherein
the hydrocarbon mixture further contains cyclopentadiene, and
the hydrocarbon production apparatus further comprises, upstream of the first extractive distillation column as viewed in a direction of flow of the hydrocarbon mixture:
a dimerizer that dimerizes cyclopentadiene in the hydrocarbon mixture to obtain a hydrocarbon mixture containing dicyclopentadiene; and
a predistillation column that performs distillation of the hydrocarbon mixture containing dicyclopentadiene to obtain the pretreated hydrocarbon mixture.

### Claim 12 (depends on 11)

The hydrocarbon production apparatus according to claim 11, further comprising:
an isoprene purification section that includes a second extractive distillation column and that purifies a fraction (C) that flows out from the top of the first distillation column to obtain high-purity isoprene;
a piperylene purification section that purifies a fraction (D) that flows out from the bottom of the first distillation column to obtain high-purity piperylene;
a dicyclopentadiene purification section that purifies a fraction (E) that flows out from the bottom of the predistillation column to obtain high-purity dicyclopentadiene; and
a hydrogenator that performs hydrogenation of at least one of a residue discharged from the isoprene purification section, a residue discharged from the piperylene purification section, and a residue discharged from the dicyclopentadiene purification section.

### Claim 13 (depends on 12)

The hydrocarbon production apparatus according to claim 12, wherein
either or both of the linear hydrocarbon and the branched hydrocarbon are dehydrogenated in the dehydrogenator, and
the hydrocarbon production apparatus further comprises a hydrogen line that supplies the hydrogenator with hydrogen produced in the dehydrogenator.