High-purity dibasic acid compositions and methods of making the same

Patent metadata

Field	Value
Publication number	US-9926255-B2
Application number	US-201615287986-A
Country	US
Kind code	B2
Filing date	Oct 7, 2016
Priority date	Oct 8, 2013
Publication date	Mar 27, 2018
Grant date	Mar 27, 2018

Abstract

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.

First claim

What is claimed is:

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.

Assignees

• Elevance Renewable Sciences

Inventors

• Patel Alpeshkumar K
• Pease Brian
• Dreyer Bradon J
• Viswanath Yenamandra
• Albert Brian
• Cohen Steven A

Classifications

• C07C67/303

  by hydrogenation of unsaturated carbon-to-carbon bonds · CPC title

• C07C51/43 Primary

  by change of the physical state, e.g. crystallisation · CPC title

• C07C67/475

  by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of [IMAGE cpc-sch-C07C-0963.gif] groups between different molecules · CPC title

• C07C51/09

  from carboxylic acid esters or lactones · CPC title