Method and system for manufacturing ester-based composition

Patent metadata

Field	Value
Publication number	US-11512166-B2
Application number	US-202016838778-A
Country	US
Kind code	B2
Filing date	Apr 2, 2020
Priority date	Apr 4, 2019
Publication date	Nov 29, 2022
Grant date	Nov 29, 2022

Abstract

The present disclosure relates to a method for continuously manufacturing an ester-based composition and a manufacturing system therefor, the method improving a manufacturing yield by optimizing process variables of each reactor of a reaction unit in which a plurality of reactors are connected in series.

First claim

The invention claimed is:

1. A method for manufacturing an ester-based composition, the method comprising:
a step S1 of injecting a polycarboxylic acid and an alcohol having 3 to 10 alkyl carbon atoms into a mixer to form a reaction mixture;
a step S2 of continuously injecting the reaction mixture into a reaction unit in which a total of N reactors are connected in series from a first reactor to an N-th reactor, thereby continuously manufacturing reaction products;
a step S3 of continuously moving the reaction products into a separation unit to remove the unreacted alcohol; and
a step S4 of injecting the unreacted alcohol removed from the separation unit back into any one reactor of the reaction unit, wherein N is an integer of 3 or greater, and Formulas 1) and 2) are satisfied:
T n1-1 ≤T n1   1)

E n2-1 ≥E n2 ≥E 1   2)

wherein, in Formulas 1) and 2), n1 is an integer of 2 to N, and n2 is an integer of 3 to N,
T x =Temperature of an x-th reactor
E x ={(Number of moles of the alcohol injected into an x-th reactor−c*Number of moles of polycarboxylic acid injected into an x-th reactor)/(c*Number of moles of polycarboxylic acid injected into the first reactor)*100%}
wherein c is the number of carboxylic acid groups contained in one molecule of the polycarboxylic acid, and in T x and E x , x is an integer of 1 to N.

2. The method of claim 1 , wherein the separation unit comprises one or more separation columns or a purification tank of a drum type.

3. The method of claim 1 , further comprising
a step S1-1 of adding a catalyst to the reaction mixture between the step S1 and the step S2; or
a step S1-2 of adding a catalyst to the polycarboxylic acid and the alcohol before the step S1.

4. The method of claim 3 , wherein the catalyst is tetraalkyl titanate.

5. The method of claim 1 , wherein the step S1 further comprises a step in which the reaction mixture is heated to 50-200° C.

6. The method of claim 1 , wherein T 1 is 100-220° C. and T N is 200-250° C.

7. The method of claim 1 , wherein E 1 is −30 to 80% and E N is 0 to 80%.

8. The method of claim 1 , further comprising a step S5 of injecting the alcohol having 3 to 10 alkyl carbon atoms into the reaction products from which the unreacted alcohol is removed to perform a trans-esterification reaction, wherein the alcohol injected in the step S5 is different from the alcohol injected in the step S1.

9. The method of claim 1 , wherein the polycarboxylic acid is one or more selected from the group consisting of a dicarboxylic acid, a tricarboxylic acid, and a tetracarboxylic acid.

10. The method of claim 9 , 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.

11. A system for manufacturing an ester-based composition, the system comprising:
a mixer in which a reaction mixture of a polycarboxylic acid and an alcohol having 3 to 10 alkyl carbon atoms is formed;
a reaction unit having N number of reactors connected in series in which an esterification reaction of the reaction mixture is performed, wherein N is an integer of 3 or greater;
a separation unit including one or more separation columns for receiving reaction products and removing the unreacted alcohol therefrom;
a recovery unit for injecting the unreacted alcohol removed from the separation unit back into a reactor of the reaction unit; and
a variable control unit that controls the temperature of each reactor and the amount of the alcohol injected into the reactor to satisfy Formulas 1) and 2) below:
T n1-1 ≤T n1   1)

E n2-1 ≥E n2 ≥E 1   2)

wherein, in Formulas 1) and 2), n1 is an integer of 2 to N, and n2 is an integer of 3 to N,
T x =Temperature of an x-th reactor
E x ={(Number of moles of the alcohol injected into an x-th reactor−c*Number of moles of polycarboxylic acid injected into an x-th reactor)/(c*Number of moles of polycarboxylic acid injected into the first reactor)*100%}
wherein c is the number of carboxylic acid groups contained in one molecule of the polycarboxylic acid, and in T x and E x , x is an integer of 1 to N.

12. The system of claim 11 , further comprising a trans-reaction unit for performing a trans-esterification reaction by adding the alcohol having 3 to 10 alkyl carbon atoms to the reaction products from which the unreacted alcohol has been removed, wherein the alcohol injected from the trans-reaction unit is different from the alcohol injected from the mixer.

Assignees

• Lg Chemical Ltd

Inventors

• Kim Hyun Kyu
• Moon Jeong Ju
• Jun Hyoung
• Lee Sung Kyu
• Jin Chan Hyu
• Kim Joo Ho

Classifications

• C08G63/183

  Terephthalic acids · CPC title

• B01J19/0053

  Details of the reactor · CPC title

• B01J19/0013

  Controlling the temperature of the process · CPC title

• C08G63/85

  Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof {(C08G63/823 takes precedence)} · CPC title

• B01J2219/00051

  Controlling the temperature · CPC title