公开(公告)号：US08809486B2

公开(公告)日：2014-08-19

申请号：US13548934

申请日：2012-07-13

申请人： Venkata Rama Narayanan Ganapathy Bhotla ,  Balakrishnan Ganesan ,  Kishan Gurram ,  Salkod Parameshwar Mallika ,  Kumar Arun Satyanarayana ,  Swaminathan Shubashree

发明人： Venkata Rama Narayanan Ganapathy Bhotla ,  Balakrishnan Ganesan ,  Kishan Gurram ,  Salkod Parameshwar Mallika ,  Kumar Arun Satyanarayana ,  Swaminathan Shubashree

IPC分类号： C08G73/10 ,  C08G73/00 ,  C08G73/06

CPC分类号： C07D209/46 ,  C08G64/12

摘要： 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. Subsequent trituration with aqueous methanol and recrystallization from isopropanol can result in product having undetectable levels of phenolphthalein derivatives.

摘要翻译： 公开了一种制备式（I）的纯化的2-芳基-3,3-双（4-羟基芳基）苯并二氮嘧啶的方法，其中R1是氢或C1-25烃基，R2是氢，C1-25烃基 基团或卤素，并且其中所述方法包括将粗的邻苯二酰亚胺化合物溶解在碱性水溶液中; 通过加入一种有效降低溶液pH至9.0至12.0的酸，从碱性水溶液中沉淀出溶解的粗的苯并二氮嘧啶化合物，得到半羟基苯并二氮嘧啶化合物; 并从碱水溶液中分离半代邻苯二甲酰亚胺化合物，得到纯化的式（I）2-芳基-3,3-双（4-羟基芳基）苯并二氮嘧啶，其酚酞化合物含量小于2,500ppm，基于 关于纯化的2-芳基-3,3-双（4-羟基芳基）苯并二氮吡啶的重量。 随后用甲醇水溶液研磨并从异丙醇中重结晶可导致具有不可检测水平的酚酞衍生物的产物。

公开(公告)号：US20100152416A1

公开(公告)日：2010-06-17

申请号：US12333451

申请日：2008-12-12

申请人： Venkata Rama Narayanan Ganapathy BHOTLA ,  Balakrishnan GANESAN ,  Kishan Gurram ,  Salkod Parameshwar MALLIKA ,  Kumar Arun Satyanarayana ,  Swaminathan SHUBASHREE

发明人： Venkata Rama Narayanan Ganapathy BHOTLA ,  Balakrishnan GANESAN ,  Kishan Gurram ,  Salkod Parameshwar MALLIKA ,  Kumar Arun Satyanarayana ,  Swaminathan SHUBASHREE

IPC分类号： C08G73/06 ,  C07D209/48 ,  C07D307/20

CPC分类号： C07D209/46 ,  C08G64/12

摘要： 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. Subsequent trituration with aqueous methanol and recrystallization from isopropanol can result in product having levels of phenolphthalein derivatives that are not detectable.

摘要翻译： 本文公开了一种制备式（I）的纯化的2-芳基-3,3-双（4-羟基芳基）苯并二氮嘧啶的方法，其中R1是氢或C1-25烃基，R2是氢，C1-25 烃基或卤素，并且其中所述方法包括将粗的邻苯二甲酰亚胺化合物溶解在碱性水溶液中; 通过加入一种有效降低溶液pH至9.0至12.0的酸，从碱性水溶液中沉淀出溶解的粗的苯并二氮嘧啶化合物，得到半羟基苯并二氮嘧啶化合物; 并从碱水溶液中分离半代邻苯二甲酰亚胺化合物，得到纯化的式（I）2-芳基-3,3-双（4-羟基芳基）苯并二氮嘧啶，其酚酞化合物含量小于2,500ppm，基于 关于纯化的2-芳基-3,3-双（4-羟基芳基）苯并二氮吡啶的重量。 随后用甲醇水溶液研磨并从异丙醇中重结晶可产生具有不可检测的酚酞衍生物含量的产物。

公开(公告)号：US07868190B2

公开(公告)日：2011-01-11

申请号：US12240112

申请日：2008-09-29

申请人： Venkata Rama Narayanan Ganapathy Bhotla ,  Shivappa Basappa Halligudi ,  Gurram Kishan ,  Salkod Parameshwar Mallika ,  Bhaskar Veldurthy

发明人： Venkata Rama Narayanan Ganapathy Bhotla ,  Shivappa Basappa Halligudi ,  Gurram Kishan ,  Salkod Parameshwar Mallika ,  Bhaskar Veldurthy

IPC分类号： C07D307/78

CPC分类号： C07D307/885

摘要： 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.

摘要翻译： 酚酞化合物的制备方法包括：使下式的酚化合物：其中R1是氢或C1-C12烃基，与下式的邻苯二甲酸酐化合物反应：其中R2是氢，C1-C12烃基 基团或卤素，在多相催化剂和促进剂的存在下形成包含下式的酚酞化合物的反应混合物：其中每个R 1独立地是氢或C 1 -C 12烃基; R2是氢，C1-C12烃基或卤素; 其中所述非均相催化剂在多孔载体上包含杂多酸组合物的煅烧产物。

公开(公告)号：US07838689B2

公开(公告)日：2010-11-23

申请号：US12239952

申请日：2008-09-29

申请人： Venkata Rama Narayanan Ganapathy Bhotla ,  Dwairath Dhar ,  Gurram Kishan ,  Salkod Parameshwar Mallika

发明人： Venkata Rama Narayanan Ganapathy Bhotla ,  Dwairath Dhar ,  Gurram Kishan ,  Salkod Parameshwar Mallika

IPC分类号： C07D407/00

CPC分类号： C09B11/08 ,  C07D307/83 ,  C09B67/0096

摘要： 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.

摘要翻译： 公开了一种生产酚酞化合物的方法，其包括：使下式的酚化合物与下式的邻苯二甲酸酐化合物反应：其中R a为氢或C 1 -C 12烃基，其中R b为氢，C 1 -C 12烃基或卤素，在离子液体催化剂组合物和促进剂的存在下形成包含下式的酚酞化合物的反应混合物：其中每个R a独立地是氢或C 1 -C 12烃基，和 Rb是氢，C1-C12烃基或卤素; 其中所述离子液体催化剂组合物包含离子液体和金属卤化物的组合，其中所述金属选自IIB，IIIA，VIII或IVA族金属及其组合。

公开(公告)号：US20100081831A1

公开(公告)日：2010-04-01

申请号：US12239952

申请日：2008-09-29

申请人： Venkata Rama Narayanan Ganapathy BHOTLA ,  Dwairath DHAR ,  Gurram KISHAN ,  Salkod Parameshwar MALLIKA

发明人： Venkata Rama Narayanan Ganapathy BHOTLA ,  Dwairath DHAR ,  Gurram KISHAN ,  Salkod Parameshwar MALLIKA

IPC分类号： C07D307/83

CPC分类号： C09B11/08 ,  C07D307/83 ,  C09B67/0096

摘要： 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

摘要翻译： 公开了一种生产酚酞化合物的方法，其包括：使下式的酚化合物与下式的邻苯二甲酸酐化合物反应：其中R a为氢或C 1 -C 12烃基，其中R b为氢，C 1 -C 12烃基或卤素，在离子液体催化剂组合物和促进剂的存在下形成包含下式的酚酞化合物的反应混合物：其中每个R a独立地是氢或C 1 -C 12烃基，和 Rb是氢，C1-C12烃基或卤素; 其中所述离子液体催化剂组合物包含离子液体和金属卤化物的组合，其中所述金属选自IIB，IIIA，VIII或IVA族金属及其组合

公开(公告)号：US20120309926A1

公开(公告)日：2012-12-06

申请号：US13548934

申请日：2012-07-13

申请人： Venkata Rama Narayanan Ganapathy BHOTLA ,  Balakrishnan GANESAN ,  Kishan GURRAM ,  Salkod Parameshwar MALLIKA ,  Kumar Arun SATYANARAYANA ,  Swaminathan SHUBASHREE

发明人： Venkata Rama Narayanan Ganapathy BHOTLA ,  Balakrishnan GANESAN ,  Kishan GURRAM ,  Salkod Parameshwar MALLIKA ,  Kumar Arun SATYANARAYANA ,  Swaminathan SHUBASHREE

IPC分类号： C07D209/46 ,  C08G73/06

CPC分类号： C07D209/46 ,  C08G64/12

摘要： 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. Subsequent trituration with aqueous methanol and recrystallization from isopropanol can result in product having undetectable levels of phenolphthalein derivatives.

摘要翻译： 公开了一种制备式（I）的纯化的2-芳基-3,3-双（4-羟基芳基）苯并二氮嘧啶的方法，其中R1是氢或C1-25烃基，R2是氢，C1-25烃基 基团或卤素，并且其中所述方法包括将粗的邻苯二酰亚胺化合物溶解在碱性水溶液中; 通过加入一种有效降低溶液pH至9.0至12.0的酸，从碱性水溶液中沉淀出溶解的粗的苯并二氮嘧啶化合物，得到半羟基苯并二氮嘧啶化合物; 并从碱水溶液中分离半代邻苯二甲酰亚胺化合物，得到纯化的式（I）2-芳基-3,3-双（4-羟基芳基）苯并二氮嘧啶，其酚酞化合物含量小于2,500ppm，基于 关于纯化的2-芳基-3,3-双（4-羟基芳基）苯并二氮吡啶的重量。 随后用甲醇水溶液研磨并从异丙醇中重结晶可导致具有不可检测水平的酚酞衍生物的产物。

公开(公告)号：US07915430B2

公开(公告)日：2011-03-29

申请号：US12239908

申请日：2008-09-29

申请人： Venkata Rama Narayanan Ganapathy Bhotla ,  Shivappa Basappa Halligudi ,  Gurram Kishan ,  Salkod Parameshwar Mallika ,  Bhaskar Veldurthy

发明人： Venkata Rama Narayanan Ganapathy Bhotla ,  Shivappa Basappa Halligudi ,  Gurram Kishan ,  Salkod Parameshwar Mallika ,  Bhaskar Veldurthy

IPC分类号： C07D209/48 ,  C07D307/20

CPC分类号： C07D307/885

摘要： 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.

摘要翻译： 一种生产酚酞的方法包括使下式的酚化合物：其中R1是氢或C1-C12烃基，与下式的邻苯二甲酸酐化合物反应：其中R2是氢，C1-C12烃基， 或卤素，在非均相催化剂和促进剂的存在下，形成包含下式的酚酞化合物的反应混合物：其中每个R 1独立地是氢或C 1 -C 12烃基，并且R 2是氢，C 1 -C12烃基或卤素; 其中所述非均相催化剂包括与多孔载体组合的金属氧化物组合物，其中所述金属是钼，钨或包含至少一种前述金属的组合。

公开(公告)号：US20100081829A1

公开(公告)日：2010-04-01

申请号：US12240112

申请日：2008-09-29

申请人： Venkata Rama Narayanan Ganapathy BHOTLA ,  Shivappa Basappa HALLIGUDI ,  Gurram KISHAN ,  Salkod Parameshwar MALLIKA ,  Bhaskar VELDURTHY

发明人： Venkata Rama Narayanan Ganapathy BHOTLA ,  Shivappa Basappa HALLIGUDI ,  Gurram KISHAN ,  Salkod Parameshwar MALLIKA ,  Bhaskar VELDURTHY

IPC分类号： C07D209/34 ,  C07D307/87

CPC分类号： C07D307/885

摘要： 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.

摘要翻译： 酚酞化合物的制备方法包括：使下式的酚化合物：其中R 1是氢或C 1 -C 12烃基与下式的邻苯二甲酸酐化合物反应：其中R 2是氢，C 1 -C 12烃基 基团或卤素，在多相催化剂和促进剂的存在下形成包含下式的酚酞化合物的反应混合物：其中每个R 1独立地是氢或C 1 -C 12烃基; R2是氢，C1-C12烃基或卤素; 其中所述多相催化剂在多孔载体上包含杂多酸组合物的煅烧产物。

公开(公告)号：US08247523B2

公开(公告)日：2012-08-21

申请号：US12333451

申请日：2008-12-12

申请人： Venkata Rama Narayanan Ganapathy Bhotla ,  Balakrishnan Ganesan ,  Kishan Gurram ,  Salkod Parameshwar Mallika ,  Kumar Arun Satyanarayana ,  Swaminathan Shubashree

发明人： Venkata Rama Narayanan Ganapathy Bhotla ,  Balakrishnan Ganesan ,  Kishan Gurram ,  Salkod Parameshwar Mallika ,  Kumar Arun Satyanarayana ,  Swaminathan Shubashree

IPC分类号： C08G73/10 ,  C08G73/00 ,  C08G73/06

CPC分类号： C07D209/46 ,  C08G64/12

摘要： 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. Subsequent trituration with aqueous methanol and recrystallization from isopropanol can result in product having levels of phenolphthalein derivatives that are not detectable.

摘要翻译： 本文公开了一种制备式（I）的纯化的2-芳基-3,3-双（4-羟基芳基）苯并二氮嘧啶的方法，其中R1是氢或C1-25烃基，R2是氢，C1-25 烃基或卤素，并且其中所述方法包括将粗的邻苯二甲酰亚胺化合物溶解在碱性水溶液中; 通过加入一种有效降低溶液pH至9.0至12.0的酸，从碱性水溶液中沉淀出溶解的粗的苯并二氮嘧啶化合物，得到半羟基苯并二氮嘧啶化合物; 并从碱水溶液中分离半代邻苯二甲酰亚胺化合物，得到纯化的式（I）2-芳基-3,3-双（4-羟基芳基）苯并二氮嘧啶，其酚酞化合物含量小于2,500ppm，基于 关于纯化的2-芳基-3,3-双（4-羟基芳基）苯并二氮吡啶的重量。 随后用甲醇水溶液研磨并从异丙醇中重结晶可产生具有不可检测的酚酞衍生物含量的产物。

公开(公告)号：US20100081828A1

公开(公告)日：2010-04-01

申请号：US12239908

申请日：2008-09-29

申请人： Venkata Rama Narayanan Ganapathy BHOTLA ,  Shivappa Basappa HALLIGUDI ,  Gurram KISHAN ,  Salkod Parameshwar MALLIKA ,  Bhaskar VELDURTHY

发明人： Venkata Rama Narayanan Ganapathy BHOTLA ,  Shivappa Basappa HALLIGUDI ,  Gurram KISHAN ,  Salkod Parameshwar MALLIKA ,  Bhaskar VELDURTHY

IPC分类号： C07D209/48 ,  C07D307/20

CPC分类号： C07D307/885

摘要： 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.

摘要翻译： 一种生产酚酞的方法包括使下式的酚化合物：其中R1是氢或C1-C12烃基，与下式的邻苯二甲酸酐化合物反应：其中R2是氢，C1-C12烃基， 或卤素，在非均相催化剂和促进剂的存在下，形成包含下式的酚酞化合物的反应混合物：其中每个R 1独立地是氢或C 1 -C 12烃基，并且R 2是氢，C 1 -C12烃基或卤素; 其中所述非均相催化剂包括与多孔载体组合的金属氧化物组合物，其中所述金属是钼，钨或包含至少一种前述金属的组合。