# US 2019/0169154 A1 · Processes and systems for the recycle of process water in the production of ethylene glycol

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- Number: US 2019/0169154 A1
- Document ID: US20190169154A1
- Status: Published application
- Kind: A1
- Application number: 16/092,843
- Filed: 2017-04-10
- Published: 2019-06-06
- Earliest claimed: 2016-04-12
- Assignees: Shell Oil Company
- Applicants: Shell Oil Company
- Inventors: Jesse Raymond BLACK; Roel Guillaume Hubertus Leonardus BASTINGS; Alexandre MOLINA
- Web page: https://patentgrep.com/patent/US20190169154A1

## CPC

- C07D 317/38: Ethylene carbonate
- B01D 3/007: {Energy recuperation; Heat pumps}
- B01D 3/148: {in combination with at least one evaporator}
- B01D 53/18: Absorbing units; Liquid distributors therefor (B01D3/16, B01D3/26, B01D3/30 take precedence; packing elements B01J19/30, B01J19/32)
- B01J 8/0446: {the flow within the beds being predominantly vertical}
- B01J 8/0492: {Feeding reactive fluids (for solid material, see B01J8/0015)}
- C07C 29/106: {of oxiranes}
- B01J 2208/025: Two or more types of catalyst
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Processes for producing ethylene carbonate and/or ethylene glycol, and associated reaction systems are similarly provided. Specifically, a process is provided that comprises supplying an overhead absorber stream withdrawn from an absorber to a vapor-liquid separator to yield an aqueous bottoms stream and a recycle gas stream; supplying an aqueous process stream comprising one or more impurities to a distillation apparatus to yield an overhead impurities stream and a purified aqueous process stream; supplying at least a portion of the purified aqueous process stream and an ethylene oxide product stream to the absorber; and contacting the ethylene oxide product stream with the purified aqueous process stream in the absorber in the presence of one or more carboxylation and hydrolysis catalysts to yield a fat absorbent stream comprising ethylene carbonate and/or ethylene glycol.

## Claims

### Claim 1

A process for the production of ethylene carbonate and/or ethylene glycol comprising:
a) supplying an overhead absorber stream withdrawn from an absorber to a vapor-liquid separator to yield an aqueous bottoms stream and a recycle gas stream;
b) supplying an aqueous process stream comprising one or more impurities to a distillation apparatus to yield an overhead impurities stream and a purified aqueous process stream;
c) supplying at least a portion of the purified aqueous process stream and an ethylene oxide product stream to the absorber; and
d) contacting the ethylene oxide product stream (4) with the purified aqueous process stream in the absorber in the presence of one or more carboxylation and hydrolysis catalysts to yield a fat absorbent stream comprising ethylene carbonate and/or ethylene glycol.

### Claim 2 (depends on 1)

The process according to claim 1 wherein the aqueous process stream supplied to the distillation apparatus comprises at least a portion of one or more streams selected from the group consisting of: the aqueous bottoms stream withdrawn from the vapor-liquid separator, an overhead dehydrator stream withdrawn from a dehydrator, and a combination thereof.

### Claim 3 (depends on 1)

The process according to claim 1, wherein the one or more impurities are selected from the group consisting of: formaldehyde, acetaldehyde, 2,3-epoxy-1,4-dioxane, 1,3-dioxolane, 1,4-dioxane, 2-methyl-1,3-dioxolane, 2-methoxy ethanol, 2,2′-bis-1,3-dioxolane, 2-chloro-methyl-1,3-dioxolane, 2-chloroethanol, and a combination thereof.

### Claim 4 (depends on 1)

The process according to claim 1 further comprising:
supplying the aqueous process stream to a preheater and a flash vessel prior to supplying the aqueous process stream to the distillation apparatus.

### Claim 5 (depends on 4)

The process according to claim 4, wherein the preheater is heated via heat integration with a hot process stream withdrawn from a separator.

### Claim 6 (depends on 1)

The process according claim 1 wherein heat is supplied to the distillation apparatus using a reboiler, and wherein the reboiler is heated by heat integration with a hot process stream withdrawn from a separator.

### Claim 7 (depends on 1)

The process according to claim 1 further comprising:
e) supplying at least a portion of the fat absorbent stream to one or more finishing reactors to yield a finishing reactor product stream, and
f) supplying at least a portion of the finishing reactor product stream to a dehydrator to yield a dehydrator bottom stream and an overhead dehydrator stream.

### Claim 8 (depends on 7)

The process according to claim 7 further comprising:
g) supplying at least a portion of the dehydrator bottom stream to a separator to yield a glycol product stream and a hot process stream; and
h) supplying at least a portion of the hot process stream to the absorber.

### Claim 9

A system for the production of ethylene carbonate and/or ethylene glycol, wherein the system comprises:
an absorber comprising one or more carboxylation and hydrolysis catalysts, at least two inlets and at least two outlets, wherein a first inlet of the absorber is fluidly connected to an outlet of an ethylene oxide reactor;
a vapor-liquid separator comprising an inlet and an outlet, wherein the inlet of the vapor-liquid separator is fluidly connected to a first outlet of the absorber; and
a distillation apparatus comprising an inlet and an outlet, wherein the inlet of the distillation apparatus is fluidly connected to the outlet of the vapor-liquid separator and the outlet of the distillation apparatus is fluidly connected to a second inlet of the absorber.

### Claim 10 (depends on 9)

The system according to claim 9 further comprising:
a preheater comprising an inlet and an outlet, wherein the inlet of the preheater is fluidly connected to the outlet of the vapor-liquid separator; and
a flash vessel comprising an inlet and an outlet, wherein the inlet of the flash vessel is fluidly connected to the outlet of the preheater and the outlet of the flash vessel is fluidly connected to the inlet of distillation apparatus.
