Processes for preparing calixarenes

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 6 alkyl.

2. 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 an amidine compound having the formula of

wherein R 1 , R 2 , R 3 , and R 4 are each independently H, alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; or any two or more of R 1 , R 2 , R 3 , and R 4 can be bonded together to form a five- to nine-membered ring structure.

3. The process of claim 2 , wherein the amidine compound is selected from the group consisting of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 1,2-dimethyl-1,4,5,6-tetrahydropyrimidine, 1-ethyl-2-methyl-1,4,5,6-tetrahydropyrimidine, 1,2-diethyl-1,4,5,6-tetrahydropyrimidine, 1-n-propyl-2-methyl-1,4,5,6-tetrahydropyrimidine, 1-isopropyl-2-methyl-1,4,5,6-tetrahydropyrimidine, 1-ethyl-2-n-propyl-1,4,5,6-tetrahydropyrimidine, and 1-ethyl-2-isopropyl-1,4,5,6-tetrahydropyrimidine.

4. 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 an imidazole compound, or a pyridine compound.

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

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

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

8. 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.

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

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 process for a high-yield, high solid-content production of a calixarene compound, comprising:

reacting a phenolic compound, an aldehyde, and a base catalyst in the presence of an organic solvent, in a highly concentrated reaction system, wherein the mass ratio of the phenolic compound to the organic solvent in the reaction system is no less than 0.25:1, to produce a calixarene-containing product having at least 50% solids, wherein the organic solvent is an ether or a mixture containing thereof.

13. The process of claim 12 , wherein the organic solvent is a mixture further containing an aromatic hydrocarbon.

14. The process of claim 12 , wherein the organic solvent is a mixture further containing a straight-chain C 11 to C 20 hydrocarbon.

15. The process of claim 12 , wherein the ether is diphenyl ether, diethylene glycol dimethyl ether, or diethylene glycol dibutyl ether.

16. The process of claim 12 , wherein the mass ratio of the phenolic compound and the organic solvent is no less than 1:1.

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

18. The process of claim 17 , wherein the phenolic compound is a para-tert-C 4 -C 8 alkyl phenol, benzyl phenol, or cumyl phenol.

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

20. The process of claim 2 , wherein the phenolic compound is phenol, an alkyl phenol, or an arylalkyl phenol.

21. The process of claim 20 , wherein the phenolic compound is a para-C 1 -C 24 alkyl phenol, benzyl phenol, or cumyl phenol.

22. The process of claim 2 , wherein the aldehyde is formaldehyde or paraformaldehyde.

23. The process of claim 2 , 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.

24. The process of claim 2 , wherein the reaction is carried out in the presence of an organic solvent.

25. The process of claim 2 , wherein the reaction is carried out under reflux conditions.

26. The process of claim 2 , wherein the aldehyde is paraformaldehyde and the reaction is carried out without reflux.

27. The process of claim 4 , wherein the imidazole compound is selected from the group consisting of imidazole, 2-methylimidazole, n-methylimidazole, and 1,2-dimethylimidazole.

28. The process of claim 4 , wherein the pyridine compound is selected from the group consisting of pyridine, 4-methylaminopyridine, 2-methylaminopyridine, and 4-dimethylaminopyridine.

29. The process of claim 4 , wherein the aldehyde is formaldehyde or paraformaldehyde.

30. The process of claim 4 , 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.

31. The process of claim 4 , wherein the reaction is carried out in the presence of an organic solvent.

32. The process of claim 4 , wherein the reaction is carried out under reflux conditions.

33. The process of claim 4 , wherein the aldehyde is paraformaldehyde and the reaction is carried out without reflux.