# US 11,111,203 B2 · System and method for manufacturing ester-based composition

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- Number: US 11,111,203 B2
- Document ID: US11111203B2
- Status: Granted
- Kind: B2
- Application number: 16/838,593
- Filed: 2020-04-02
- Published: 2020-10-08
- Granted: 2021-09-07
- Earliest claimed: 2019-04-04
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Hyun Kyu Kim; Sung Kyu Lee; Jeong Ju Moon; Hyoung Jun; Chan Hyu Jin
- Web page: https://patentgrep.com/patent/US11111203B2

## CPC

- B01J 19/2445: {placed in parallel}
- B01D 3/14: Fractional distillation {or use of a fractionation or rectification column}
- B01J 4/008: {Feed or outlet control devices}
- B01J 19/0053: {Details of the reactor}
- B01J 31/12: containing organo-metallic compounds or metal hydrides
- C07C 67/03: by reacting an ester group with a hydroxy group
- C07C 67/08: by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
- C07C 67/48: Separation; Purification; Stabilisation; Use of additives
- B01J 31/122: {Metal aryl or alkyl compounds}
- B01J 2204/002: the feeding side being of particular interest
- B01J 2219/00031: Semi-batch or fed-batch processes
- B01J 2219/00038: Processes in parallel
- B01J 2219/00164: controlling the flow
- B01J 2231/49: Esterification or transesterification
- B01J 2531/46: Titanium
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- 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

## Abstract

The present disclosure relates to a method and a system for manufacturing an ester-based composition which are characterized in sequentially operating a plurality of batch reactors, and since an ester-based composition is semi-continuously manufactured, the productivity is high and the stability of a batch reactor is secured.

## Claims

### Claim 1

A system for manufacturing an ester-based composition, the system comprising:
a mixer in which a reaction mixture of a polycarboxylic acid and a first alcohol having 3 to 10 alkyl carbon atoms is formed, wherein the mixer comprises a polycarboxylic acid injection path and a first alcohol injection path;
a reaction unit provided with N number of batch reactors connected in parallel in which an esterification reaction of the reaction mixture is performed, an inlet line for receiving the reaction mixture from the mixer, and an outlet line for discharging reaction products from the N number of batch reactors;
a supply control unit for controlling the injection amount and the injection path of the reaction mixture such that the reaction mixture is sequentially supplied to the N number of batch reactors from the mixer to allow the reaction to be sequentially completed, wherein the supply control unit is disposed between the mixer and the reaction unit; and
a separation unit for receiving the reaction products through the outlet line of the reaction unit and removing unreacted alcohol therefrom.

### Claim 2 (depends on 1)

The system of claim 1, further comprising a trans-reaction unit for performing a trans-esterification reaction by adding a second alcohol having 3 to 10 alkyl carbon atoms to the reaction products from which the unreacted alcohol has been removed, wherein the second alcohol injected from the trans-reaction unit is different from the first alcohol injected from the mixer.

### Claim 3 (depends on 1)

The system of claim 1, wherein at least one batch reactor a mong the N number of batch reactors comprises a gas-liquid separation column connected to an upper portion of the batch reactor and separating alcohol and water discharged through the upper portion of the batch reactor, a condenser for cooling a gas discharged through an upper line of the gas-liquid separation column, and a decanter for separating a liquid discharged through a lower line of the gas-liquid separation column and a liquid condensed in the condenser into different layers and recirculating the alcohol into the batch reactor.

### Claim 4 (depends on 1)

The system of claim 1, wherein the supply control unit controls one or more of the injection path and the injection flow rate of the reaction mixture to be changed according a predetermined time interval.

### Claim 5 (depends on 4)

The system of claim 4, wherein the time interval is 50% to 150% of a value obtained by dividing the reaction duration in one batch reactor by N.

### Claim 6

A system for manufacturing an ester-based composition, the system comprising:
a mixer in which a reaction mixture of a polycarboxylic acid and a first alcohol having 3 to 10 alkyl carbon atoms is formed, wherein the mixer comprises a polycarboxylic acid injection path and a first alcohol injection path;
a reaction unit provided with N number of batch reactors connected in parallel in which an esterification reaction of the reaction mixture is performed, an inlet line for receiving the reaction mixture from the mixer, and an outlet line for discharging reaction products from the N number of batch reactors;
a supply control unit for controlling the injection amount and the injection path of the reaction mixture such that the reaction mixture is sequentially supplied to the N number of batch reactors from the mixer to allow the reaction to be sequentially completed, wherein the supply control unit is disposed between the mixer and the reaction unit; and
a separation unit for receiving the reaction products through the outlet line of the reaction unit and removing unreacted alcohol therefrom,
wherein the polycarboxylic acid is one or more selected from the group consisting of a dicarboxylic acid, a tricarboxylic acid, and a tetracarboxylic acid.

### Claim 7 (depends on 6)

The system of claim 6, wherein
the dicarboxylic acid is one or more selected from the group consisting of a linear dicarboxylic acid having 2 to 10 carbon atoms, a terephthalic acid, a phthalic acid, an isophthalic acid, a cyclohexane dicarboxylic acid, an anhydride thereof, and a derivative thereof,
the tricarboxylic acid is one or more selected from the group consisting of a citric acid, a trimellitate acid, a cyclohexane tricarboxylic acid, an anhydride thereof, and a derivative thereof, and
the tetracarboxylic acid is one or more selected from the group consisting of a benzenetetracarboxylic acid, a furantetracarboxylic acid, a cyclohexane tetracarboxylic acid, a tetrahydrofuran tetracarboxylic acid, an anhydride thereof, and a derivative thereof.
