Processes for preparing calixarenes

Patent metadata

Field	Value
Publication number	US-12049440-B2
Application number	US-202117554438-A
Country	US
Kind code	B2
Filing date	Dec 17, 2021
Priority date	Feb 9, 2018
Publication date	Jul 30, 2024
Grant date	Jul 30, 2024

Abstract

This invention relates to a process for preparing a calixarene compound by reacting a phenolic compound and an aldehyde in the presence of at least one nitrogen-containing base as a catalyst to form the calixarene compound. The invention also relates to processes for high-yield, high solid-content production of a calixarene compound, with high selectivity toward a high-purity calix[8]arene compound, without carrying out a recrystallization step.

First claim

We claim:

1. A process for preparing a calixarene compound, comprising:
reacting a phenolic compound and an aldehyde in the presence of at least one nitrogen-containing base as a catalyst to form the calixarene compound, wherein the nitrogen-containing base is a tetraalkyl ammonium hydroxide, wherein each alkyl moiety in the tetraalkyl ammonium hydroxide is independently C 1 to C 2 alkyl.

2. The process of claim 1 , wherein the tetraalkyl ammonium hydroxide is tetramethyl ammonium hydroxide.

3. The process of claim 1 , wherein the tetraalkyl ammonium hydroxide is tetraethyl ammonium hydroxide.

4. The process of claim 1 , wherein the phenolic compound is phenol, an alkyl phenol, or an arylalkyl phenol.

5. The process of claim 4 , wherein the phenolic compound is a para-C 1 -C 24 alkyl phenol, benzyl phenol, or cumyl phenol.

6. The process of claim 1 , wherein the aldehyde is formaldehyde or paraformaldehyde.

7. The process of claim 1 , wherein the molar ratio of the phenolic compound to the aldehyde ranges from about 1:1.5 to about 1.5:1, and the molar ratio of the phenolic compound to the nitrogen-containing base ranges from about 200:1 to about 20:1.

8. The process of claim 1 , wherein the reaction is carried out in the presence of an organic solvent.

9. The process of claim 8 , wherein the mass ratio of the phenolic compound to the organic solvent is no less than 0.25:1.

10. The process of claim 1 , wherein the reaction is carried out under reflux conditions.

11. The process of claim 1 , wherein the aldehyde is paraformaldehyde and the reaction is carried out without reflux.

12. A one-step process for preparing a calixarene compound, comprising:
reacting a phenolic compound and an aldehyde in the presence of at least one nitrogen-containing base as a catalyst to form the calixarene compound in a one-step process, wherein the nitrogen-containing base is a tetraalkyl ammonium hydroxide, wherein each alkyl moiety in the tetraalkyl ammonium hydroxide is independently C 1 to C 6 alkyl.

13. The process of claim 12 , wherein the phenolic compound is phenol, an alkyl phenol, or an arylalkyl phenol.

14. The process of claim 13 , wherein the phenolic compound is a para-C 1 -C 24 alkyl phenol, benzyl phenol, or cumyl phenol.

15. The process of claim 12 , wherein the aldehyde is formaldehyde or paraformaldehyde.

16. The process of claim 12 , wherein the molar ratio of the phenolic compound to the aldehyde ranges from about 1:1.5 to about 1.5:1, and the molar ratio of the phenolic compound to the nitrogen-containing base ranges from about 200:1 to about 20:1.

17. The process of claim 12 , wherein the reaction is carried out in the presence of an organic solvent.

18. The process of claim 17 , wherein the mass ratio of the phenolic compound to the organic solvent is no less than 0.25:1.

19. The process of claim 12 , wherein the reaction is carried out under reflux conditions.

20. The process of claim 12 , wherein the aldehyde is paraformaldehyde and the reaction is carried out without reflux.

Assignees

• Si Group Inc

Inventors

• Haase Cornelius
• Biittig Ricky
• Staats Allyson
• Atwood Philip David
• Webb Jim
• Chichak Kelly

Classifications

• C08G8/12

  with monohydric phenols having only one hydrocarbon substituent ortho on para to the OH group, e.g. p-tert.-butyl phenol · CPC title

• C07C39/15

  with all hydroxy groups on non-condensed rings {, e.g. phenylphenol} · CPC title

• B01J31/0244

  with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine · CPC title

• B01J31/0239

  Quaternary ammonium compounds · CPC title

• C07C37/20 Primary

  using aldehydes or ketones · CPC title