High-purity dibasic acid compositions and methods of making the same
View Patent ↗High-purity dibasic acid compositions are generally disclosed. In some embodiments, the dibasic acid compositions are solutions or suspensions. In some other embodiments, the compositions are solid-state compositions. In some such embodiments, the solid-state compositions include a dibasic acid as a crystalline solid and further include a low quantity of certain impurities, such as monobasic acids, various esters, and the like. Methods and systems for making such high-purity dibasic acid compositions are also disclosed.
1. A method of forming a purified solid-state dibasic acid composition, comprising:
providing a first composition, which comprises a first amount of dibasic acid and a first amount of one or more monobasic acids, each dissolved in a solvent system; and
cooling the first composition to form a second composition, which comprises a second amount of the dibasic acid in solid-state form suspended in the solvent system, and a second amount of the one or more monobasic acids dissolved in the solvent system;
wherein at least 80 percent by weight of the one or more monobasic acids in the second composition are dissolved in the solvent system; and
wherein the one or more monobasic acids comprise compounds of formula (IVa) and, optionally, compounds of formula (IVb):
wherein:
Y 2 is C 6-36 alkylene, C 6-36 alkenylene, C 4-36 oxyalkylene, each of which is optionally substituted one or more times by substituents selected from the group consisting of a halogen atom, —OH, —O(C 1-6 alkyl), —NH 2 , —NH(C 1-6 alkyl), and N(C 1-6 alkyl) 2 ;
R 5 is C 1-12 alkyl, C 1-12 heteroalkyl, C 2-12 alkenyl, or C 2-12 heteroalkenyl, each of which is optionally substituted one or more times by substituents selected independently from R 6 ;
R 6 is a halogen atom, —OH, —NH 2 , C 1-6 alkyl, C 1-6 heteroalkyl, C 2-6 alkenyl, C 2-6 heteroalkenyl, C 3-10 cyclokalkyl, or C 2-10 heterocycloalkyl;
R 8 C 1-12 alkyl, C 1-12 heteroalkyl, C 2-12 alkenyl, or C 2-12 heteroalkenyl, each of which is optionally substituted one or more times by substituents selected independently from R 9 ; and
R 9 is a halogen atom, C 1-6 alkyl, C 1-6 heteroalkyl, C 2-6 alkenyl, C 2-6 heteroalkenyl, C 6-14 aryl, C 2-14 heteroaryl, C 3-10 cyclokalkyl, or C 2-10 heterocycloalkyl.
2. The method of claim 1 , wherein the first composition is heated to at least 40° C.
3. The method of claim 2 , wherein the solvent system comprises toluene, ortho-xylene, meta-xylene, para-xylene, acetone, dimethylformamide, tetrahydrofuran, methylene dichloride, dimethyl sulfoxide, or any mixture thereof.
4. The method of claim 3 , wherein the solvent system comprises toluene, ortho-xylene, meta-xylene, para-xylene, or any mixture thereof.
5. The method claim 1 , wherein the dibasic acid is a compound of formula (II):
wherein, Y 1 is C 6-36 alkylene, C 6-36 alkenylene, C 6-36 heteroalkylene, or C 6-36 heteroalkenylene, each of which is optionally substituted one or more times by substituents selected independently from R 3 ;
R 3 is a halogen atom, —OH, —NH 2 , C 1-6 alkyl, C 1-6 heteroalkyl, C 2-6 alkenyl, or C 2-6 heteroalkenyl.
6. The method of claim 5 , wherein Y 1 is C 6-36 alkylene, C 6-36 alkenylene, or C 4-36 oxyalkylene, each of which is optionally substituted one or more times by substituents selected from the group consisting of a halogen atom, —OH, —O(C 1-6 alkyl), —NH 2 , —NH(C 1-6 alkyl), and N(C 1-6 alkyl) 2 .
7. The method of claim 6 , wherein Y 1 is C 6-36 alkylene, C 6-36 alkenylene, or C 4-36 oxyalkylene, each of which is optionally substituted one or more times by —OH.
8. The method of claim 7 , wherein Y 1 is —(CH 2 ) 8 —, —(CH 2 ) 9 —, —(CH 2 ) 10 —, —(CH 2 ) 11 —, —(CH 2 ) 12 —, —(CH 2 ) 13 —, —(CH 2 ) 14 —, —(CH 2 ) 15 —, —(CH 2 ) 16 —, —(CH 2 ) 17 —, —(CH 2 ) 18 —, —(CH 2 ) 19 —, —(CH 2 ) 20 —, —(CH 2 ) 21 —, or —(CH 2 ) 22 —.
9. The method of claim 1 , wherein at least 80 percent of the dibasic acid in the second composition is in solid-state form suspended in the solvent system.
10. The method of claim 1 , wherein Y 2 is C 6-36 alkylene, C 6-36 alkenylene, or C 4-36 oxyalkylene, each of which is optionally substituted one or more times by —OH.
11. The method of claim 10 , wherein Y 2 is —(CH 2 ) 8 —, —(CH 2 ) 9 —, —(CH 2 ) 10 —, —(CH 2 ) 11 —, —(CH 2 ) 12 —, —(CH 2 ) 13 —, —(CH 2 ) 14 —, —(CH 2 ) 15 —, —(CH 2 ) 16 —, —(CH 2 ) 17 —, —(CH 2 ) 18 —, —(CH 2 ) 19 —, —(CH 2 ) 20 —, —(CH 2 ) 21 —, or —(CH 2 ) 22 —.
12. The method of claim 1 , wherein R 5 is C 1-14 alkyl, C 2-14 alkenyl, or C 2-14 oxyalkyl, each of which is optionally substituted one or more times by —OH.
13. The method of claim 12 , wherein R 5 is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, tert-pentyl, neopentyl, hexyl, or 2-ethylhexyl.
14. The method of claim 13 , wherein R 5 is methyl.
15. The method of claim 1 , wherein R 8 is C 1-14 alkyl, C 2-14 alkenyl, or C 2-14 oxyalkyl, each of which is optionally substituted one or more times by —OH.
16. The method of claim 15 , wherein R 8 is heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, or heptadecyl.
17. The method of claim 15 , wherein R 8 is nonyl or undecyl.