IP Library Granted Patent US 12,270,000
Granted Patent B2
US 12,270,000 · App. 18/247,138 · Granted Apr 8, 2025

Recovery of aliphatic hydrocarbons

Inventors: Jean-Paul Andre Marie Joseph Ghislain Lange (Amsterdam, NL); Kai Jürgen Fischer (Amsterdam, NL); Guus Van Rossum (Amsterdam, NL); Timothé Johannes Olthof (Amsterdam, NL); Willem Derks (Amsterdam, NL); Hendrik Stichter (Amsterdam, NL)
Assignee: SHELL USA, INC.
C10G67/0445C10G67/06C10G2300/202C10G2300/4081
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Quick Facts
Patent No.
US 12,270,000
App. No.
18/247,138
Granted
Apr 8, 2025
Kind
B2
Abstract

The invention relates to a process for the recovery of aliphatic hydrocarbons from a liquid stream comprising aliphatic hydrocarbons, heteroatom containing organic compounds and optionally aromatic hydrocarbons, involving a) liquid-liquid extraction of said liquid stream with an extraction solvent, wherein before and/or after step a) heteroatom containing organic compounds, optional aromatic hydrocarbons and optional other contaminants are removed from said liquid stream and/or from a raffinate stream resulting from step a), respectively, by contacting the latter stream(s) with a sorption agent. Further, the invention relates to a process for the recovery of aliphatic hydrocarbons from plastics comprising the above-mentioned process; and to a process for steam cracking a hydrocarbon feed comprising aliphatic hydrocarbons as recovered in one of the above-mentioned processes.

Claims (32)

1. A process for the recovery of aliphatic hydrocarbons from a liquid hydrocarbon feedstock stream comprising aliphatic hydrocarbons, heteroatom containing organic compounds and optionally aromatic hydrocarbons, wherein the liquid hydrocarbon feedstock stream comprises at least part of a hydrocarbon product formed in a process comprising cracking of waste plastics, said process comprising the step of:

a) contacting at least part of the liquid hydrocarbon feedstock stream with an extraction solvent a) which contains one or more heteroatoms and subjecting the liquid hydrocarbon feedstock stream to liquid-liquid extraction with the extraction solvent a), resulting in a first stream comprising aliphatic hydrocarbons and a second stream comprising extraction solvent a), heteroatom containing organic compounds and optionally aromatic hydrocarbons; and

b) mixing at least part of the second stream resulting from step a) with a demixing solvent b) which contains one or more heteroatoms and has a miscibility in heptane which is lower than the miscibility of extraction solvent a) in heptane, and separating the resulting mixture into a first stream comprising heteroatom containing organic compounds and optionally aromatic hydrocarbons and a second stream comprising extraction solvent a) and demixing solvent b); wherein:

(i) before step a), part of the heteroatom containing organic compounds is removed from the liquid hydrocarbon feedstock stream by contacting at least part of that stream with a sorption agent; and

(ii) after step a), heteroatom containing organic compounds are removed from the first stream resulting from step a), wherein that stream comprises aliphatic hydrocarbons and heteroatom containing organic compounds, by contacting at least part of that stream with a sorption agent.

2. The process according to claim 1 , wherein:

(i) part of the heteroatom containing organic compounds is removed from the liquid hydrocarbon feedstock stream by contacting at least part of that stream with a sorption agent, and at least part of the treated stream resulting from step (i) is fed to step a); and

(ii) the first stream resulting from step a) comprises aliphatic hydrocarbons and heteroatom containing organic compounds, and heteroatom containing organic compounds are removed from that stream by contacting at least part of that stream with a sorption agent.

3. The process according to claim 1 , further comprising the steps of:

c) separating at least part of the second stream resulting from step b) into a first stream comprising demixing solvent b) and a second stream comprising extraction solvent a);

d) recycling at least part of the extraction solvent a) from the second stream resulting from step c) to step a); and

e) optionally recycling at least part of the demixing solvent b) from the first stream resulting from step c) to step b).

4. The process according to claim 1 , wherein:

the extraction solvent a) has a R a,heptane of at least 5 MPa 1/2 and a demixing solvent b) has a R a,heptane of at least 20 MPa 1/2 , wherein R a,heptane refers to the Hansen solubility parameter distance with respect to heptane as determined at 25° C.; and

the R a,heptane for the demixing solvent b) is greater than the R a,heptane for extraction solvent a), wherein said difference in R a,heptane for solvents a) and b) is at least 1 MPa 1/2 .

5. The process according to claim 1 , wherein the extraction solvent a) comprises one or more solvents selected from the group consisting of ammonia diols and triols, including monoethylene glycol (MEG), monopropylene glycol (MPG), any isomer of butanediol and glycerol; glycol ethers, including oligoethylene glycols, including diethylene glycol, triethylene glycol and tetraethylene glycol, and monoalkyl ethers thereof, including diethylene glycol ethyl ether; amides, including N-alkylpyrrolidone, wherein the alkyl group comprises 1 to 8 carbon atoms, including N-methylpyrrolidone (NMP), formamide and di- and monoalkyl formamides and acetamides, wherein the alkyl group comprises 1 to 8 carbon atoms, including dimethyl formamide (DMF), methyl formamide and dimethyl acetamide; dialkylsulfoxide, wherein the alkyl group comprises 1 to 8 carbon atoms, including dimethylsulfoxide (DMSO); sulfones, including sulfolane; N-formyl morpholine (NFM); furan ring containing components and derivatives thereof, including furfural, 2-methyl-furfuran, furfuryl alcohol and tetrahydrofurfuryl alcohol; hydroxy esters, including lactates, including methyl and ethyl lactate; trialkyl phosphates, including triethyl phosphate;

phenolic compounds, including phenol and guaiacol; benzyl alcoholic compounds, including benzyl alcohol; aminic compounds, including ethylenediamine, monoethanolamine, diethanolamine and triethanolamine; nitrile compounds, including acetonitrile and propionitrile;

trioxane compounds, including 1,3,5-trioxane; carbonate compounds, including propylene carbonate and glycerol carbonate; and cycloalkanone compounds, including dihydrolevoglucosenone.

6. The process according to claim 3 , wherein the demixing solvent b) comprises one or more solvents selected from the group consisting of water and diols and triols, including monoethylene glycol (MEG), monopropylene glycol (MPG), any isomer of butanediol and glycerol; glycol ethers, including oligoethylene glycols, including diethylene glycol, triethylene glycol and tetraethylene glycol, and monoalkyl ethers thereof, including diethylene glycol ethyl ether; amides, including N-alkylpyrrolidone, wherein the alkyl group comprises 1 to 8 carbon atoms, including N-methylpyrrolidone (NMP), formamide and di- and monoalkyl formamides and acetamides, wherein the alkyl group comprises 1 to 8 carbon atoms, including dimethyl formamide (DMF), methyl formamide and dimethyl acetamide; dialkylsulfoxide, wherein the alkyl group comprises 1 to 8 carbon atoms, including dimethylsulfoxide (DMSO); sulfones, including sulfolane; N-formyl morpholine (NFM); furan ring containing components and derivatives thereof, including furfural, 2-methyl-furan, furfuryl alcohol and tetrahydrofurfuryl alcohol; hydroxy esters, including lactates, including methyl and ethyl lactate, trialkyl phosphates, including triethyl phosphate;

phenolic compounds including phenol and guaiacol; benzyl alcoholic compounds, including benzyl alcohol; aminic compounds, including ethylenediamine, monoethanolamine, diethanolamine, and triethanolamine; nitrile compounds, including acetonitrile and propionitrile;

trioxane compounds, including 1,3,5-trioxane; carbonate compounds, including propylene carbonate and glycerol carbonate; and cycloalkanone compounds, including dihydrolevoglucosenone.

7. The process according to claim 1 , wherein:

a washing solvent c) is added to step a) resulting in a first stream comprising aliphatic hydrocarbons and a second stream comprising washing solvent c), extraction solvent a), heteroatom containing organic compounds and optionally aromatic hydrocarbons; or

the first stream resulting from step a) comprises aliphatic hydrocarbons and extraction solvent a), at least part of which first stream is contacted with a washing solvent c) and is subjected to liquid-liquid extraction with the washing solvent c), resulting in a first stream comprising aliphatic hydrocarbons and a second stream comprising washing solvent c) and extraction solvent a).

8. The process according to claim 7 , wherein the washing solvent c) is identical to or different from demixing solvent b).

9. A process for the recovery of aliphatic hydrocarbons from plastics, wherein at least part of the plastics comprises heteroatom containing organic compounds, said process comprising the steps of:

(I) cracking the plastics and recovering a hydrocarbon product comprising aliphatic hydrocarbons, heteroatom containing organic compounds and optionally aromatic hydrocarbons; and

(II) subjecting a liquid hydrocarbon feedstock stream, which comprises at least part of the hydrocarbon product obtained in step (I), to the process of claim 1 .

10. Process for steam cracking a hydrocarbon feed, wherein the hydrocarbon feed comprises aliphatic hydrocarbons as recovered in a process according to claim 1 .

11. Process for steam cracking a hydrocarbon feed, comprising the steps of:

recovering aliphatic hydrocarbons from a liquid hydrocarbon feedstock stream in a process according to claim 1 , and

steam cracking a hydrocarbon feed which comprises aliphatic hydrocarbons as recovered in the preceding step.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 30, 2023
From: LANGE, JEAN-PAUL ANDRE MARIE JOSEPH GHISLAIN; FISCHER, KAI JÜRGEN; VAN ROSSUM, GUUS; OLTHOF, TIMOTHÉ JOHANNES; DERKS, WILLEM; STICHTER, HENDRIK
To: SHELL USA, INC.
Reel/Frame 063794/0604 →
CHANGE OF NAME Recorded Mar 30, 2023
From: SHELL OIL COMPANY
To: SHELL USA, INC.
Reel/Frame 063192/0071 →
Priority Claims (1)
EP 20202190 · Oct 16, 2020 · regional
Continuity (1)
Related Publication 20230374401A1 · Nov 23, 2023
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