# US 12,116,532 B2 · Compositions from the chemical recycling of plastic-derived streams and uses thereof

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- Number: US 12,116,532 B2
- Document ID: US12116532B2
- Status: Granted
- Kind: B2
- Application number: 17/760,372
- Filed: 2021-02-10
- Published: 2023-04-20
- Granted: 2024-10-15
- Earliest claimed: 2020-02-10
- Assignees: Eastman Chemical Company
- Applicants: Eastman Chemical Company
- Inventors: Daryl Bitting; David Eugene Slivensky; Xianchun Wu; Bruce Roger DeBruin; Damon Ray Billodeaux
- Web page: https://patentgrep.com/patent/US12116532B2

## CPC

- C10G 1/10: from rubber or rubber waste
- C01B 3/32: by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide or air
- C10B 53/07: {of solid raw materials consisting} of synthetic polymeric materials, e.g. tyres (recovery or working-up of waste materials of organic macromolecular compounds or compositions based thereon by dry-heat treatment for obtaining partially depolymerised materials C08J11/10; production of liquid hydrocarbon mixtures from rubber or rubber waste C10G1/10)
- C10G 1/002: {in combination with oil conversion- or refining processes}
- C10G 9/00: Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
- C10J 3/62: with separate withdrawal of the distillation products
- C10J 3/66: by introducing them into the gasification zone
- C10K 3/008: {by cracking}
- C01B 2203/025: containing a partial oxidation step
- C10G 2300/1003: Waste materials
- C10G 2300/201: Impurities
- C10G 2300/202: Heteroatoms content, i.e. S, N, O, P
- C10G 2300/4006: Temperature
- C10G 2300/4012: Pressure
- C10G 2400/20: C2-C4 olefins
- C10G 2400/26: Fuel gas
- C10G 2400/28: Propane and butane
- C10J 2300/0903: Feed preparation
- C10J 2300/0906: Physical processes, e.g. shredding, comminuting, chopping, sorting
- C10J 2300/0909: Drying
- C10J 2300/0926: Slurries comprising bio-oil or bio-coke, i.e. charcoal, obtained, e.g. by fast pyrolysis of biomass
- C10J 2300/0946: Waste, e.g. MSW, tires, glass, tar sand, peat, paper, lignite, oil shale
- C10J 2300/0969: Carbon dioxide
- C10J 2300/0973: Water
- C10J 2300/0976: as steam
- C10J 2300/1846: Partial oxidation, i.e. injection of air or oxygen only
- Y02P 20/143: the feedstock being recycled material, e.g. plastics
- 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
- C01B: NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; {METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C}
- C10B: DESTRUCTIVE DISTILLATION OF CARBONACEOUS MATERIALS FOR PRODUCTION OF GAS, COKE, TAR, OR SIMILAR MATERIALS (cracking oils C10G; underground gasification of minerals E21B43/295)
- C10J: PRODUCTION OF PRODUCER GAS, WATER-GAS, SYNTHESIS GAS FROM SOLID CARBONACEOUS MATERIAL, OR MIXTURES CONTAINING THESE GASES (synthesis gas from liquid or gaseous hydrocarbons C01B; underground gasification of minerals E21B43/295); CARBURETTING AIR OR OTHER GASES
- C10K: PURIFYING OR MODIFYING THE CHEMICAL COMPOSITION OF COMBUSTIBLE GASES CONTAINING CARBON MONOXIDE
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Methods and systems are provided for the conversion of waste plastics into various useful downstream recycle-content products. More particularly, the present system and method involves integrating a pyrolysis facility with a cracker facility by introducing at least a stream of r-pyrolysis gas into the cracker facility. In the cracker facility, the r-pyrolysis gas may be separated to form one or more recycle content products, and can enhance the operation of the facility.

## Claims

### Claim 1

A recycle content pyrolysis gas (r-pyrolysis gas) composition, wherein said r-pyrolysis gas composition comprises:
at least 20 and not more than 75 weight percent of ethylene and/or propylene;
at least 5 and not more than 50 weight percent of ethane and/or propane;
at least 5 and not more than 60 weight percent of methane;
an ethylene to ethane weight ratio or propylene to propane weight ratio of at least 1:1 and not more than 3:1; C4+ olefins in an amount of not more than 10 weight percent;
C4 paraffins in an amount of not more than 5 weight percent; and
at least one of the following properties (i) through (ix):
(i) C4 hydrocarbons in an amount of not more than 20 weight percent;
(ii) hydrogen in an amount of not more than 10 weight percent;
(iii) C3+ diolefins in an amount of not more than 10 weight percent;
(iv) halogens in an amount of not more than 1 ppm;
(v) carbonyls in an amount of not more than 100 ppm;
(vi) carbon dioxide in an amount of not more than 100 ppm;
(vii) carbon monoxide in an amount of not more than 2500 ppm;
(viii) arsine and/or phosphine in an amount of not more than 15 ppb; and
(ix) sulfur-containing compounds in an amount of not more than 100 ppm,
and
wherein said r-pyrolysis gas is formed by the pyrolysis of recycle waste plastic or materials derived therefrom; wherein a portion of said r-pyrolysis gas is not hydrogenated that is sent to a cracking furnace; and wherein said composition comprises at least 0.5 and not more than about 35 weight percent of butadiene, based on the total weight of the composition.

### Claim 2 (depends on 1)

The composition of claim 1, wherein said composition comprises at least 0.1 and not more than 25 weight percent of nitrogen-containing compounds, based on the total weight of the composition.

### Claim 3 (depends on 1)

The composition of claim 1, wherein said composition comprises at least 0.5 and not more than about 35 weight percent of butadiene, based on the total weight of the composition.

### Claim 4 (depends on 1)

The composition of claim 1, wherein said composition comprises not more than about 35 weight percent of C5 and heavier components, based on the total weight of the composition.

### Claim 5 (depends on 1)

The composition of claim 1, wherein said composition comprises not more than about 35 weight percent of aromatics, based on the total weight of the composition.

### Claim 6 (depends on 1)

The composition of claim 1, wherein the composition includes at least two of the properties (i) through (ix).

### Claim 7 (depends on 1)

The composition of claim 1, wherein said composition comprises at least 20 and not more than 75 weight percent of ethylene.

### Claim 8 (depends on 1)

The composition of claim 1, wherein said composition has an ethylene to ethane weight ratio of at least 1:1 and not more than 3:1.

### Claim 9 (depends on 1)

The composition of claim 1, wherein said composition comprises at least 5 and not more than 50 weight percent of ethane.

### Claim 10 (depends on 1)

The composition of claim 1, wherein said composition comprises at least 20 and not more than 75 weight percent of propylene.

### Claim 11 (depends on 1)

The composition of claim 1, wherein said composition has an propylene to propane weight ratio of at least 1:1 and not more than 3:1.

### Claim 12 (depends on 1)

The composition of claim 1, wherein said composition comprises at least 5 and not more than 50 weight percent of propane, based on the total weight of the composition.

### Claim 13 (depends on 1)

The composition of claim 1, wherein the composition has a pressure of not more than 500 psig.

### Claim 14 (depends on 1)

The composition of claim 1, wherein the composition has a pressure of at least 200 psig.

### Claim 15 (depends on 1)

The composition of claim 1, wherein the composition has a temperature of at least 250 and not more than 1000° C.