METHODS OF MANUFACTURE OF SALTS OF HYDROXY-SUBSTITUTED AROMATIC COMPOUNDS AND POLYETHERIMIDES

1 . A method for the manufacture of a metal salt of a hydroxy-substituted aromatic compound, the method comprising:

reacting a hydroxy-substituted aromatic compound with a base comprising a metal cation in an aqueous medium to provide a mixture comprising water and a metal salt of the hydroxy-substituted aromatic compound;

contacting the mixture with a substantially water-immiscible solvent at a temperature greater than the boiling point of water at a prevailing pressure;

introducing an optionally substituted C 1-6 aliphatic alcohol; and

removing water and the alcohol to provide a slurry comprising the metal salt of the hydroxy-substituted aromatic compound and the water-immiscible solvent.

2 . A method for the manufacture of a metal salt of a hydroxy-substituted aromatic compound, the method comprising:

reacting a hydroxy-substituted aromatic compound with a base comprising a metal cation in an aqueous medium to provide a mixture comprising water and a metal salt of the hydroxy-substituted aromatic compound;

contacting the mixture with a substantially water-immiscible solvent at a temperature greater than the boiling point of water at a prevailing pressure;

partially removing water and the water-immiscible solvent from the contacted mixture to provide a water-immiscible, solvent-rich phase comprising the metal salt of the hydroxy-substituted aromatic compound and the water-immiscible solvent;

introducing an optionally substituted C 1-6 aliphatic alcohol to the water-immiscible phase to provide a solution; and

separating the water and the isopropanol from the solution to provide a slurry comprising the metal salt of the hydroxy-substituted aromatic compound and the water-immiscible solvent.

3 . A method for the manufacture of a metal salt of a hydroxy-substituted aromatic compound, the method comprising:

reacting a hydroxy-substituted aromatic compound with a base comprising a metal cation in an organic medium comprising isopropanol, to provide a mixture comprising a metal salt of the hydroxy-substituted aromatic compound, an optionally substituted C 1-6 alcohol, and water produced from the reaction between the hydroxy-substituted aromatic compound and the base;

contacting the mixture with a substantially water-immiscible solvent at a temperature greater than the boiling point of water at a prevailing pressure to provide a mixture further comprising the substantially water-immiscible solvent; and

removing water and the alcohol from the mixture further comprising the substantially water-immiscible solvent, to provide a slurry comprising the metal salt of the hydroxy-substituted aromatic compound and the water-immiscible solvent.

4 . The method of claim 1 , wherein the slurry comprises less than 500 ppm of water.

5 . The method of claim 1 , wherein the method further comprises:

introducing a polar aprotic solvent to the slurry, wherein the polar aprotic solvent has a boiling point greater than the boiling point of the water-immiscible solvent; and

removing the water-immiscible solvent from the slurry containing the polar aprotic solvent, to provide a composition comprising the polar aprotic solvent and the metal salt of the hydroxy-substituted aromatic compound.

6 . The method of claim 5 , wherein the polar aprotic solvent is diphenyl sulfone, sulfolane, dimethyl sulfoxide, N-methyl-2-pyrrolidone, dimethyl formamide, DMAc, or a combination comprising at least one of the foregoing.

7 . The method of claim 1 , wherein the aliphatic alcohol is isopropanol.

8 . The method of claim 1 , wherein the hydroxyl-substituted aromatic compound is of the formula

wherein R a and R b are each independently a halogen atom or a monovalent C 1-12 hydrocarbon group, p and q are each independently integers of 0 to 4, c is zero to 4, and X a is a single bond, —O—, —S—, —S(O)—, —S(O) 2 —, —C(O)—, or a C 1-18 organic bridging group; and

the base is an alkali metal hydroxide, an alkaline carbonate, an alkali bicarbonate, or a combination comprising at least one of the foregoing.

9 . The method of claim 1 , wherein

the hydroxyl-substituted aromatic compound is 2,2-bis(4-hydroxyphenyl)propane or 4,4′-dihydroxybiphenyl; and

the base is sodium hydroxide or potassium hydroxide.

10 . The method of claim 1 , wherein the water-immiscible solvent comprises benzene, toluene, xylene, phenetole, anisole, veratrole, diphenylsulfone, chlorobenzene, bromobenzene, ortho-dichlorobenzene, 1,3-dichlorobenzene, 1,4-dichlorobenzene, 1,3,5-trichlorobenzene, 1,2,4-trichlorobenzene, or a combination comprising at least one of the foregoing.

11 . The method of claim 1 , wherein the water-immiscible solvent comprises ortho-dichlorobenzene.

12 . A method for the manufacture of a polyetherimide composition, the method comprising

polymerizing a bis(N-(substituted phthalimido))aromatic compound and an alkali metal salt of a dihydroxy aromatic compound of claim 1 to form a polyetherimide composition.

13 . The method of claim 12 , wherein the polymerizing is carried out without a phase transfer catalyst.

14 . The method of claim 12 , wherein the polymerization is carried out in the presence of a phase transfer catalyst.

15 . The method of claim 2 , wherein the method further comprises:

introducing a polar aprotic solvent to the slurry, wherein the polar aprotic solvent has a boiling point greater than the boiling point of the water-immiscible solvent; and

removing the water-immiscible solvent from the slurry containing the polar aprotic solvent, to provide a composition comprising the polar aprotic solvent and the metal salt of the hydroxy-substituted aromatic compound.

16 . The method of claim 2 , wherein the polar aprotic solvent is diphenyl sulfone, sulfolane, dimethyl sulfoxide, N-methyl-2-pyrrolidone, dimethyl formamide, DMAc, or a combination comprising at least one of the foregoing.

17 . The method of claim 2 , wherein the aliphatic alcohol is isopropanol.

18 . The method of claim 3 , wherein the method further comprises:

introducing a polar aprotic solvent to the slurry, wherein the polar aprotic solvent has a boiling point greater than the boiling point of the water-immiscible solvent; and

removing the water-immiscible solvent from the slurry containing the polar aprotic solvent, to provide a composition comprising the polar aprotic solvent and the metal salt of the hydroxy-substituted aromatic compound.

19 . The method of claim 3 , wherein the polar aprotic solvent is diphenyl sulfone, sulfolane, dimethyl sulfoxide, N-methyl-2-pyrrolidone, dimethyl formamide, DMAc, or a combination comprising at least one of the foregoing.

20 . The method of claim 3 , wherein the aliphatic alcohol is isopropanol.