	US 12,215,186 B2
	Process for making novel polycondensation pre-polyesters, other copolyester precursors, and copolyesters
Robert Jacks Sharpe, Madison, AL (US); and Emmett Dudley Crawford, Kingsport, TN (US)
Assigned to Eastman Chemical Company, Kingsport, TN (US)
Appl. No. 17/596,690
Filed by Eastman Chemical Company, Kingsport, TN (US)
PCT Filed Jun. 26, 2020, PCT No. PCT/US2020/039742 § 371(c)(1), (2) Date Dec. 16, 2021, PCT Pub. No. WO2020/264244, PCT Pub. Date Dec. 30, 2020.
Claims priority of provisional application 62/868,314, filed on Jun. 28, 2019.
Claims priority of provisional application 62/868,299, filed on Jun. 28, 2019.
Prior Publication US 2022/0363816 A1, Nov. 17, 2022
Int. Cl. C08G 63/183 (2006.01); C07C 69/75 (2006.01); C07C 69/82 (2006.01); C07D 307/68 (2006.01); C08G 63/199 (2006.01)

CPC C08G 63/183 (2013.01) [C07C 69/75 (2013.01); C07C 69/82 (2013.01); C07D 307/68 (2013.01); C08G 63/199 (2013.01); C07C 2601/04 (2017.05); C07C 2601/14 (2017.05); C07C 2601/16 (2017.05)]

20 Claims

1. A process for making a polycondensation pre-polyester, a polyester, or both, comprising the following steps:

A. Acylation of at least one diacid chloride to form at least one diester, comprising the following steps:

1. Adding at least one alcohol, at least one base, and optionally, at least one aprotic solvent to a first reaction zone;

2. Adding at least one aprotic solvent and at least one diacid chloride to a second reaction zone;

3. Feeding the contents in the first reaction zone into the second reaction zone;

B. Partial hydrolysis of the diester product of Step A to form at least one monoacid comprising the following steps:

1. Adding the product of Step A and at least one aprotic solvent to a third reaction zone;

2. Adding at least one base, water, and at least one alcohol to a fourth reaction zone;

3. Feeding the contents in the fourth reaction zone into the third reaction zone; and

C. Esterifying the monoacid of Step B to form a diester comprising the following steps:

1. Adding the monoacid of Step B, at least one diol, at least one catalyst, at least one aprotic solvent and at least one carbodiimide and reacting under esterification conditions;

D. Reacting the diester of Step C and with acidic conditions to form a diacid, comprising the following steps:

1. Reacting the diester of Step C with at least one acid, and at least one aprotic solvent; and then performing either Step E or Step F as follows:

E. Bisalkylation of the diacid of Step D to form a pentamer comprising the following step: dissolve the diacid of Step D in at least one aprotic solvent, add at least one base, and then react with at least one haloalcohol; or

F. Esterifiying the diacid of Step D to form a pentamer comprising the following step: dissolve the diacid of Step D in at least one aprotic solvent and react with at least one diol and at least one carbodiimide with at least one catalyst, provided that the diol is not the same as in Step C.