Abstract: Methods for synthesizing and purifying 2-aryl-3,3-bis(4-hydroxyaryl)phthalimidine compounds are provided. The method includes heating a reaction mixture including a phenolphthalein, a primary aryl amine, and an acid catalyst to form a phthalimidine; precipitating the phthalimidine from the reaction mixture to provide a crude phthalimidine; providing a solution including the crude phthalimidine, an additive, and at least one solvent; contacting the solution with one or more purification agents to provide a treated solution; precipitating and recovering a phthalimidine adduct from the treated solution; and recovering a purified phthalimidine compound from the adduct.

Abstract: Methods for synthesizing and purifying 2-aryl-3,3-bis(4-hydroxyaryl)phthalimidine compounds are provided. The method includes heating a reaction mixture including a phenolphthalein, a primary aryl amine, and an acid catalyst to form a phthalimidine; precipitating the phthalimidine from the reaction mixture to provide a crude phthalimidine; providing a solution including the crude phthalimidine, an additive, and at least one solvent; contacting the solution with one or more purification agents to provide a treated solution; precipitating and recovering a phthalimidine adduct from the treated solution; and recovering a purified phthalimidine compound from the adduct.

Abstract: Disclosed herein is a method for producing a purified 2-aryl-3,3-bis(4-hydroxyaryl)phthalimidine of formula (I) wherein R1 is hydrogen or a C1-25 hydrocarbyl group and R2 is a hydrogen, a C1-25 hydrocarbyl group, or a halogen, and wherein the method comprises dissolving a crude phthalimidine compound in an aqueous base solution; precipitating the dissolved, crude phthalimidine compound from the aqueous base solution by adding an acid in an amount effective to lower the pH of the solution to 9.0 to 12.0, to provide a semicrude phthalimidine compound; and isolating the semicrude phthalimidine compound from the aqueous base solution, to provide the purified 2-aryl-3,3-bis(4-hydroxyaryl)phthalimidine of formula (I), and having a phenolphthalein compound content of less than 2,500 ppm, based on the weight of the purified 2-aryl-3,3-bis(4-hydroxyaryl)phthalimidine.

Abstract: Disclosed herein is a method for producing a purified 2-aryl-3,3-bis(4-hydroxyaryl) phthalimidine of formula (I) wherein R1 is hydrogen or a C1-25 hydrocarbyl group and R2 is a hydrogen, a C1-25 hydrocarbyl group, or a halogen, and wherein the method comprises dissolving a crude phthalimidine compound in an aqueous base solution; precipitating the dissolved, crude phthalimidine compound from the aqueous base solution by adding an acid in an amount effective to lower the pH of the solution to 9.0 to 12.0, to provide a semicrude phthalimidine compound; and isolating the semicrude phthalimidine compound from the aqueous base solution, to provide the purified 2-aryl-3,3-bis(4-hydroxyaryl) phthalimidine of formula (I), and having a phenolphthalein compound content of less than 2,500 ppm, based on the weight of the purified 2-aryl-3,3-bis(4-hydroxyaryl)phthalimidine.

Abstract: Disclosed is a method for producing a purified 2-aryl-3,3-bis(4-hydroxyaryl)phthalimidine of formula (I) wherein R1 is hydrogen or a C1-25 hydrocarbyl group and R2 is a hydrogen, a C1-25 hydrocarbyl group, or a halogen, and wherein the method comprises dissolving a crude phthalimidine compound in an aqueous base solution; precipitating the dissolved, crude phthalimidine compound from the aqueous base solution by adding an acid in an amount effective to lower the pH of the solution to 9.0 to 12.0, to provide a semicrude phthalimidine compound; and isolating the semicrude phthalimidine compound from the aqueous base solution, to provide the purified 2-aryl-3,3-bis(4-hydroxyaryl)phthalimidine of formula (I), and having a phenolphthalein compound content of less than 2,500 ppm, based on the weight of the purified 2-aryl-3,3-bis(4-hydroxyaryl)phthalimidine.

Abstract: Disclosed is a method for producing a purified 2-aryl-3,3-bis(4-hydroxyaryl)phthalimidine of formula (I) wherein R1 is hydrogen or a C1-25 hydrocarbyl group and R2 is a hydrogen, a C1-25 hydrocarbyl group, or a halogen, and wherein the method comprises dissolving a crude phthalimidine compound in an aqueous base solution; precipitating the dissolved, crude phthalimidine compound from the aqueous base solution by adding an acid in an amount effective to lower the pH of the solution to 9.0 to 12.0, to provide a semicrude phthalimidine compound; and isolating the semicrude phthalimidine compound from the aqueous base solution, to provide the purified 2-aryl-3,3-bis(4-hydroxyaryl)phthalimidine of formula (I), and having a phenolphthalein compound content of less than 2,500 ppm, based on the weight of the purified 2-aryl-3,3-bis(4-hydroxyaryl)phthalimidine.

Abstract: Disclosed herein is a method for producing a purified 2-aryl-3,3-bis(4-hydroxyaryl) phthalimidine of formula (I) wherein R1 is hydrogen or a C1-25 hydrocarbyl group and R2 is a hydrogen, a C1-25 hydrocarbyl group, or a halogen, and wherein the method comprises dissolving a crude phthalimidine compound in an aqueous base solution; precipitating the dissolved, crude phthalimidine compound from the aqueous base solution by adding an acid in an amount effective to lower the pH of the solution to 9.0 to 12.0, to provide a semicrude phthalimidine compound; and isolating the semicrude phthalimidine compound from the aqueous base solution, to provide the purified 2-aryl-3,3-bis(4-hydroxyaryl)phthalimidine of formula (I), and having a phenolphthalein compound content of less than 2,500 ppm, based on the weight of the purified 2-aryl-3,3-bis(4-hydroxyaryl)phthalimidine.

Abstract: A method of producing a phenolphthalein comprises reacting a phenolic compound of the formula: wherein R1 is a hydrogen or a C1-C12 hydrocarbyl group, with a phthalic anhydride compound of the formula: wherein R2 is a hydrogen, a C1-C12 hydrocarbyl group, or a halogen, in the presence of a heterogeneous catalyst and a promoter to form a reaction mixture comprising a phenolphthalein compound of the formula: wherein each R1 is independently a hydrogen or a C1-C12 hydrocarbyl group, and R2 is a hydrogen, a C1-C12 hydrocarbyl group, or a halogen; wherein the heterogeneous catalyst comprises a metal oxide composition in combination with a porous support, wherein the metal is molybdenum, tungsten, or a combination comprising at least one of the foregoing metals.

Abstract: A method for producing a phenolphthalein compound comprises: reacting a phenolic compound of the formula: wherein R1 is a hydrogen or a C1-C12 hydrocarbyl group, with a phthalic anhydride compound of the formula: wherein R2 is a hydrogen, a C1-C12 hydrocarbyl group, or a halogen, in the presence of a heterogeneous catalyst and a promoter to form a reaction mixture comprising a phenolphthalein compound of the formula: wherein each R1 is independently a hydrogen or a C1-C12 hydrocarbyl group; and R2 is a hydrogen, a C1-C12 hydrocarbyl group, or a halogen; wherein the heterogeneous catalyst comprises, on a porous support, a calcination product of a heteropolyacid composition.

Abstract: A method for producing a phenolphthalein compound is disclosed, comprising: reacting a phenolic compound of the formula: wherein Ra is a hydrogen or a C1-C12 hydrocarbyl group, with a phthalic anhydride compound of the formula: wherein Rb is a hydrogen, a C1-C12 hydrocarbyl group, or a halogen, in the presence of an ionic liquid catalyst composition and a promoter to form a reaction mixture comprising a phenolphthalein compound of the formula: wherein each Ra is independently a hydrogen or a C1-C12 hydrocarbyl group, and Rb is a hydrogen, a C1-C12 hydrocarbyl group, or a halogen; wherein the ionic liquid catalyst composition comprises a combination of an ionic liquid and a metal halide wherein the metal is selected from the group consisting of a Group IIB, IIIA, VIII, or IVA metal, and a combination thereof.

Abstract: A method for purifying a 2-aryl-3,3-bis(hydroxyaryl)phthalimidine comprises contacting a crude 2-aryl-3,3-bis(hydroxyaryl)phthalimidine with a purification agent, removing a 2-aryl-3-(aminoaryl)-3-(hydroxyaryl)phthalimidine compound from the crude 2-aryl-3,3-bis(hydroxyaryl)phthalimidine, and producing a purified 2-aryl-3,3-bis(hydroxyaryl)phthalimidine product comprising less than 200 parts per million of the 2-aryl-3-(aminoaryl)-3-(hydroxyaryl)phthalimidine compound. The purification agent is selected from the group consisting of an acidic material, an organic acid chloride, an organic anhydride, or a combination thereof. The 2-aryl-3-(aminoaryl)-3-(hydroxyaryl)phthalimidine compound has a formula: wherein each R1 is independently selected from a group consisting of a hydrocarbyl radical, a nitro radical, and a halogen atom; “a” is an integer from 0 to 4; and Ar1 and Ar2 are independently at each occurrence an aromatic radical.

Abstract: Disclosed herein is a method for producing a purified 2-aryl-3,3-bis(4-hydroxyaryl) phthalimidine of formula (I) wherein R1 is hydrogen or a C1-25 hydrocarbyl group and R2 is a hydrogen, a C1-25 hydrocarbyl group, or a halogen, and wherein the method comprises dissolving a crude phthalimidine compound in an aqueous base solution; precipitating the dissolved, crude phthalimidine compound from the aqueous base solution by adding an acid in an amount effective to lower the pH of the solution to 9.0 to 12.0, to provide a semicrude phthalimidine compound; and isolating the semicrude phthalimidine compound from the aqueous base solution, to provide the purified 2-aryl-3,3-bis(4-hydroxyaryl)phthalimidine of formula (I), and having a phenolphthalein compound content of less than 2,500 ppm, based on the weight of the purified 2-aryl-3,3-bis(4-hydroxyaryl)phthalimidine.

Abstract: A method for producing a phenolphthalein compound is disclosed, comprising: reacting a phenolic compound of the formula: wherein Ra is a hydrogen or a C1-C12 hydrocarbyl group, with a phthalic anhydride compound of the formula: wherein Rb is a hydrogen, a C1-C12 hydrocarbyl group, or a halogen, in the presence of an ionic liquid catalyst composition and a promoter to form a reaction mixture comprising a phenolphthalein compound of the formula: wherein each Ra is independently a hydrogen or a C1-C12 hydrocarbyl group, and Rb is a hydrogen, a C1-C12 hydrocarbyl group, or a halogen; wherein the ionic liquid catalyst composition comprises a combination of an ionic liquid and a metal halide wherein the metal is selected from the group consisting of a Group IIB, IIIA, VIII, or IVA metal, and a combination thereof

Abstract: A method of producing a phenolphthalein comprises reacting a phenolic compound of the formula: wherein R1 is a hydrogen or a C1-C12 hydrocarbyl group, with a phthalic anhydride compound of the formula: wherein R2 is a hydrogen, a C1-C12 hydrocarbyl group, or a halogen, in the presence of a heterogeneous catalyst and a promoter to form a reaction mixture comprising a phenolphthalein compound of the formula: wherein each R1 is independently a hydrogen or a C1-C12 hydrocarbyl group, and R2 is a hydrogen, a C1-C12 hydrocarbyl group, or a halogen; wherein the heterogeneous catalyst comprises a metal oxide composition in combination with a porous support, wherein the metal is molybdenum, tungsten, or a combination comprising at least one of the foregoing metals.

Abstract: A method for producing a phenolphthalein compound comprises: reacting a phenolic compound of the formula: wherein R1 is a hydrogen or a C1-C12 hydrocarbyl group, with a phthalic anhydride compound of the formula: wherein R2 is a hydrogen, a C1-C12 hydrocarbyl group, or a halogen, in the presence of a heterogeneous catalyst and a promoter to form a reaction mixture comprising a phenolphthalein compound of the formula: wherein each R1 is independently a hydrogen or a C1-C12 hydrocarbyl group; and R2 is a hydrogen, a C1-C12 hydrocarbyl group, or a halogen; wherein the heterogeneous catalyst comprises, on a porous support, a calcination product of a heteropolyacid composition.

Abstract: Disclosed herein is a method comprising reacting a phenolphthalein material and a primary hydrocarbyl amine in the presence of an acid catalyst to form a reaction mixture comprising 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine, wherein the phenolphthalein material comprises greater than or equal to 99 weight percent phenolphthalein, based on the total weight of the phenolphthalein material; quenching the reaction mixture and treating the quenched reaction mixture to obtain a first solid. The first solid is purified by a combination of techniques to produce a solid comprising 2-hydrocarbyl-3,3-bis(4-hydroxyaryl)phthalimidine with sufficient purity to be used as a monomer in the synthesis of clear polymers.

Abstract: A method for purifying a 2-aryl-3,3-bis(hydroxyaryl)phthalimidine comprises contacting a crude 2-aryl-3,3-bis(hydroxyaryl)phthalimidine with a purification agent, removing a 2-aryl-3-(aminoaryl)-3-(hydroxyaryl)phthalimidine compound from the crude 2-aryl-3,3-bis(hydroxyaryl)phthalimidine, and producing a purified 2-aryl-3,3-bis(hydroxyaryl)phthalimidine product comprising less than 200 parts per million of the 2-aryl-3-(aminoaryl)-3-(hydroxyaryl)phthalimidine compound. The purification agent is selected from the group consisting of an acidic material, an organic acid chloride, an organic anhydride, or a combination thereof. The 2-aryl-3-(aminoaryl)-3-(hydroxyaryl)phthalimidine compound has a formula: wherein each R1 is independently selected from a group consisting of a hydrocarbyl radical, a nitro radical, and a halogen atom; “a” is an integer from 0 to 4; and Ar1 and Ar2 are independently at each occurrence an aromatic radical.

Abstract: Methods for purifying a p,p-bisphenol A generally include distilling a feed stream comprising p,p-BPA in a distillation column at a pressure less than or equal to 20 millibars. The distillation column separates the bisphenol feed stream to produce a light fraction, an intermediate fraction and a heavy fraction. The intermediate fraction comprising the purified bisphenol contains lesser impurities that the p,p-BPA in the feed stream. In one embodiment, the intermediate stream is recovered using a side-draw. The side-draw is located between a first zone and a third zone in the distillation column.