# US 12,214,304 B2 · Separating hydrocarbons with dihydrolevoglucosenone or a derivative of dihydrolevoglucosenone as a solvent

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- Number: US 12,214,304 B2
- Document ID: US12214304B2
- Status: Granted
- Kind: B2
- Application number: 17/913,494
- Filed: 2021-04-19
- Published: 2023-06-29
- Granted: 2025-02-04
- Earliest claimed: 2020-04-24
- Assignees: Shell USA, Inc.
- Applicants: Shell USA, Inc.
- Inventors: Thomas Brouwer; Boelo Schuur
- Web page: https://patentgrep.com/patent/US12214304B2

## CPC

- B01D 3/40: Extractive distillation
- C07C 7/08: by extractive distillation
- C10G 21/16: Oxygen-containing 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)
- 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

## Abstract

The present invention provides a process for separating unsaturated hydrocarbons from a mixture of saturated and unsaturated hydrocarbons, which process comprises the steps of (a) contacting the mixture with a solvent; (b) allowing to form two phases in equilibrium, a first phase comprising solvent and unsaturated hydrocarbons and a second phase comprising the remainder of the mixture; (c) removing the phases separately; and (d) removing from at least one of the phases the hydrocarbons to obtain at least one product stream and regenerated solvent for use in step (a), wherein the solvent comprises dihydrolevoglucosenone or a derivative of dihydrolevoglucosenone.

## Claims

### Claim 1

Process for separating unsaturated hydrocarbons from a mixture of saturated and unsaturated hydrocarbons, which process comprises the steps of
(a) contacting the mixture with a solvent;
(b) allowing to form two phases in equilibrium, a first phase comprising solvent and unsaturated hydrocarbons and a second phase comprising the remainder of the mixture;
(c) removing the phases separately; and
(d) removing (i) unsaturated hydrocarbons from the first phase, (ii) saturated hydrocarbons from the second phase, or (iii) unsaturated hydrocarbons from the first phase and saturated hydrocarbons from the second phase, to obtain at least one product stream and regenerated solvent for use in step (a),
wherein the solvent comprises dihydrolevoglucosenone.

### Claim 2 (depends on 1)

Process according to claim 1, comprising the steps of
(1) feeding the mixture into a distillation column having a stripping section and a rectifying section, wherein the mixture is introduced between the stripping section and the rectifying section;
(2) introducing the solvent into the top of the distillation column;
(3) removing from the bottom of the distillation column a bottom stream comprising solvent and unsaturated hydrocarbons;
(4) reheating part of the bottom stream to obtain a vapour stream that is introduced into the bottom of the distillation column;
(5) removing unsaturated hydrocarbons from the remainder of the bottom stream to obtain a first product stream comprising unsaturated hydrocarbons and regenerated solvent for use in step (2);
(6) removing from the top of the distillation column a vapour stream comprising the remainder of the mixture; and
(7) condensing the vapour stream and returning a first part of the condensed vapour stream as reflux into the top of the distillation column, and withdrawing the remaining second part of the condensed vapour stream as distillate.

### Claim 3 (depends on 1)

Process according to claim 1, comprising the steps of
(1) feeding the mixture in liquid form together with the solvent into a contactor;
(2) allowing in the contactor the formation of two phases, a liquid extract comprising solvent and unsaturated hydrocarbons and a liquid raffinate comprising the remainder of the mixture;
(3) removing the liquid extract from the contactor;
(4) removing unsaturated hydrocarbons from the liquid extract to obtain a first product stream comprising unsaturated hydrocarbons and regenerated solvent for use in step (1);
(5) removing the liquid raffinate from the contactor; and
(6) removing hydrocarbons from the liquid raffinate to obtain a second product stream comprising the remainder of the mixture and regenerated solvent for use in step (1).