USRE34626E - Isomerization of bisphenols - Google Patents

Isomerization of bisphenols Download PDF

Info

Publication number
USRE34626E
USRE34626E US08/027,734 US2773493A USRE34626E US RE34626 E USRE34626 E US RE34626E US 2773493 A US2773493 A US 2773493A US RE34626 E USRE34626 E US RE34626E
Authority
US
United States
Prior art keywords
carbon atoms
bisphenol
bisphenols
acid
phenol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US08/027,734
Inventor
Udo Rudolph
Claus Wulff
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Priority to US08/027,734 priority Critical patent/USRE34626E/en
Application granted granted Critical
Publication of USRE34626E publication Critical patent/USRE34626E/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by exchange of hydrocarbon groups, which may be substituted, from the same of other compounds, e.g. transalkylation

Definitions

  • This invention relates to a process for the preparation of bisphenols and bisphenol mixtures by the isomerization of bisphenols on acid or alkaline catalysts in the presence of the corresponding phenols.
  • Bisphenols are important raw materials for chemical products such as epoxide resins and polycarbonates based e.g. on bisphenol A.
  • the properties of the polycarbonate may be modified for certain applications by adding other polycarbonates to these polymers, e.g. polycarbonates based on other bisphenols, e.g. for the purpose of increasing the flame resIstance of polycarbonates based on tetrachloro or tetrabromobisphenol A. etc., for increasing the heat distortion temPerature of polycarbonates based on tetramethyl bisphenol, etc . . .
  • Bisphenol A and alkyl phenols may be converted into 3,5-dimethyl-4,4'-dihydroxydiphenyl-2,2-propane and/or 3,3',5,5'-tetramethyl-4,4-dihydroxydiphenyl-2,2-propane and/or 1,1,3,4,6-pentamethyl-3-(3,5-dimethyl-4-hydroxyphenyl)-indan-5-ol.
  • the present invention therefore relates to a process for the isomerization of bisphenols, characterized in that bisphenols are reacted with phenols in the presence of catalysts.
  • bisphenol A for example, can readily be isomerized into the following bisphenols in the presence of 2,6-dimethyl phenol and in the presence of a suitable catalyst:
  • Bisphenol A for example, will give rise to other bisphenols in the presence of suitable catalysts and in the presence of other phenols.
  • Suitable other phenols have at least one unsubstituted position on the aromatic ring.
  • Multinuclear phenols may also be used according to the invention.
  • R 1 to R 8 may be identical or different and denote. independently of one another, hydrogen or C 1 to C 12 alkyl and X denotes a C 1 to C 12 alkylidene or C 3 to C 12 cycloalkylidene group in the ortho or para position to the OH group
  • bisphenols corresponding to formula (IV): 2,2-bis-(4-hydroxyphenol)-propane (bisphenol A), 2,2-bis-(4-hydroxyphenyl)-butane, 2,2-bis-(4-hydroxyphenyl)-2-methylbutane and 1,1-bis-(4-hydroxyphenyl)-cyclohexane.
  • Bisphenol A is preferred.
  • the phenols may be compounds corresponding to formula (V) ##STR5## wherein
  • R 1 , R 2 , R 3 and R 4 denote, independently of one another, hydrogen, C 1 to C 12 alkyl, halogen (e.g. Cl, Br), C 6 to C 24 aryl, C 1 to C 12 alkoxy or C 5 to C 30 cycloalkyl, C 1 to C 12 alkyl being preferred.
  • the catalysts used according to the invention may be acids or bases, preferably acids for example protonic acids such as hydrohalic acids, e.g. hydrochloric acid; sulphuric acid, perchloric acid, benzene sulphonic acid, lewis acids such as borone trifluoride, acid ion exchange resins, etc . . . Acid ion exchange resins are preferred.
  • hydrohalic acids e.g. hydrochloric acid
  • sulphuric acid perchloric acid
  • benzene sulphonic acid lewis acids
  • acids such as borone trifluoride, acid ion exchange resins, etc . . .
  • Acid ion exchange resins are preferred.
  • the catalysts may be used e.g. with the addition of sulphurcontaining compounds such as those commonly used e.g. for the preparation of bisphenol A from phenol and acetone.
  • the ion exchange resins may be partly or completely neutralized with mercapto amines or thiazolines (e.g. U.S. Pat. No. 3,394,089).
  • Suitable acid ion exchangers include the commercially available reaction products of styrene-divinyl benzene copolymers with conventional sulphonating agents such as sulphuric acid, chlorosulphonic acid, etc . . . They may be available e.g. in a spherical form, (particle sizes from 0.3 to 1.5 mm in diameter). They may have a normal or a monodisperse diameter distribution.
  • Their total capacity of acid functions in a water-moist form with a water content of about 75 to 85% by weight ranges from 0.7 to 2.1 mval/ml of ion exchanger, preferably from 3.5 to 5 mval, based on 1 g of dry substance of ion exchanger.
  • the reaction according to the invention is carried out at the temperatures normally employed for the preparation of bisphenol. Temperatures from 20° to 150° C., especially from 40° to 80° C. have proved to be suitable.
  • the reaction may be carried out at pressures below or above normal pressure, e.g. at 10 -3 to 10 -5 bar. Normal pressure is preferred.
  • the water moist ion exchangers may be dried before their use according to the invention by means of heat (20° to 150° C.), optionally under vacuum (up to 10 -5 bar) or optionally by washing with hydrophilic organic liquids such as alcohols (e.g. methanol, ethanol or propanols) or phenols or by azeotropic distillation with organic liquids such as toluene, xylene, methylene chloride, etc . . .
  • hydrophilic organic liquids such as alcohols (e.g. methanol, ethanol or propanols) or phenols
  • organic liquids such as toluene, xylene, methylene chloride, etc . . .
  • the ion exchange resin is then rinsed with the phenol required for the preparation of the bisphenol and the bisphenol which is to be converted is dissolved in this medium at temperatures above the melting point of the phenol.
  • the reaction mixture obtained after the reaction of bisphenol and phenol may be worked up by the usual methods such as distillation, crystallization, etc . . .
  • the process may be carried out continuously or batch wise.
  • the bisphenol or mixture of bisphenols prepared by this process may be used for known applications and is suitable in particular for the preparation of polycarbonates and of polymer alloys obtainable from the polycarbonates.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

This invention relates to a process for the preparation of bisphenols and bisphenol mixtures by the isomerization of bisphenols on acid or alkaline catalysts in the presence of the corresponding phenols.

Description

This invention relates to a process for the preparation of bisphenols and bisphenol mixtures by the isomerization of bisphenols on acid or alkaline catalysts in the presence of the corresponding phenols.
Bisphenols are important raw materials for chemical products such as epoxide resins and polycarbonates based e.g. on bisphenol A. The properties of the polycarbonate may be modified for certain applications by adding other polycarbonates to these polymers, e.g. polycarbonates based on other bisphenols, e.g. for the purpose of increasing the flame resIstance of polycarbonates based on tetrachloro or tetrabromobisphenol A. etc., for increasing the heat distortion temPerature of polycarbonates based on tetramethyl bisphenol, etc . . .
These processes are very complicated. They require not only a polycarbonate based on bisphenol A but in addition the preparation of a sufficient quantity of another bisphenol and of the corresponding polycarbonate. There are only a few bisphenols on the market apart from bisphenol A so that the preparation of other bisphenols generally requires development of a new process. Moreover, mixing of the polymers requires an additional step, e.g. of extrusion.
It has now been found that bisphenols isomerize in the presence of a certain phenol, e.g. 2,6-dimethyl phenol, in the presence of a suitable catalyst.
Bisphenol A and alkyl phenols, for example, may be converted into 3,5-dimethyl-4,4'-dihydroxydiphenyl-2,2-propane and/or 3,3',5,5'-tetramethyl-4,4-dihydroxydiphenyl-2,2-propane and/or 1,1,3,4,6-pentamethyl-3-(3,5-dimethyl-4-hydroxyphenyl)-indan-5-ol.
The present invention therefore relates to a process for the isomerization of bisphenols, characterized in that bisphenols are reacted with phenols in the presence of catalysts.
According to the invention, bisphenol A, for example, can readily be isomerized into the following bisphenols in the presence of 2,6-dimethyl phenol and in the presence of a suitable catalyst:
3,5-dimethyl-4,4'-dihydroxydiphenyl-2,2-propane (I) ##STR1##
3,3',5,5'-tetramethyl-4,4'-dihydroxydiphenyl-2,2-propane (II) ##STR2##
1,1,3,4,6-pentamethyl-3-(3,5-dimethyl-4-hydroxyphenyl)-indan-5-ol (III) ##STR3##
Bisphenol A, for example, will give rise to other bisphenols in the presence of suitable catalysts and in the presence of other phenols. Suitable other phenols have at least one unsubstituted position on the aromatic ring. The following are examples: mono- to tetra-C1 -C12 -alkyl-substituted phenols such as o-, m- and p-methyl phenol, o-, m-, and p-ethyl phenol, etc.; 2,6-dimethyl phenol etc.; mono or multi halogenated phenols (e.g. with Cl or Br) such as o-, m- and p-chlorophenol, o-, m- and p-bromophenol, 2,6-dichlorophenol, 2,6-dibormophenol, etc.; mono- or multi- C1 -C10 -alkoxy-substituted phenols and mono- or multi- C6 -C24 -aryl or C5 -C30 -cycloalkyl-substituted phenols, etc. Multinuclear phenols may also be used according to the invention.
Bisphenols corresponding to formula (IV) ##STR4## wherein R1 to R8 may be identical or different and denote. independently of one another, hydrogen or C1 to C12 alkyl and X denotes a C1 to C12 alkylidene or C3 to C12 cycloalkylidene group in the ortho or para position to the OH group
may also be used according to the invention.
The following are examples of bisphenols corresponding to formula (IV): 2,2-bis-(4-hydroxyphenol)-propane (bisphenol A), 2,2-bis-(4-hydroxyphenyl)-butane, 2,2-bis-(4-hydroxyphenyl)-2-methylbutane and 1,1-bis-(4-hydroxyphenyl)-cyclohexane. Bisphenol A is preferred.
The phenols may be compounds corresponding to formula (V) ##STR5## wherein
R1, R2, R3 and R4 denote, independently of one another, hydrogen, C1 to C12 alkyl, halogen (e.g. Cl, Br), C6 to C24 aryl, C1 to C12 alkoxy or C5 to C30 cycloalkyl, C1 to C12 alkyl being preferred.
The catalysts used according to the invention may be acids or bases, preferably acids for example protonic acids such as hydrohalic acids, e.g. hydrochloric acid; sulphuric acid, perchloric acid, benzene sulphonic acid, lewis acids such as borone trifluoride, acid ion exchange resins, etc . . . Acid ion exchange resins are preferred.
The catalysts may be used e.g. with the addition of sulphurcontaining compounds such as those commonly used e.g. for the preparation of bisphenol A from phenol and acetone. U.S. Pat. Nos. .Badd.2,468,982 and 2,623,908, for example, disclose the use of e.g. thioglycolic acid and 3-mercaptopropionic acid; the addition of thiophenols is known from U.S. Pat. No. 2,359,242, the addition of alkyl mercaptans is known from U.S. Pat. No. 2,775,620 and the addition of hydrogen sulphide is known from Chemical Abstracts 58, 1403e. The ion exchange resins may be partly or completely neutralized with mercapto amines or thiazolines (e.g. U.S. Pat. No. 3,394,089).
Examples of suitable acid ion exchangers include the commercially available reaction products of styrene-divinyl benzene copolymers with conventional sulphonating agents such as sulphuric acid, chlorosulphonic acid, etc . . . They may be available e.g. in a spherical form, (particle sizes from 0.3 to 1.5 mm in diameter). They may have a normal or a monodisperse diameter distribution. Their total capacity of acid functions in a water-moist form with a water content of about 75 to 85% by weight ranges from 0.7 to 2.1 mval/ml of ion exchanger, preferably from 3.5 to 5 mval, based on 1 g of dry substance of ion exchanger.
The reaction according to the invention is carried out at the temperatures normally employed for the preparation of bisphenol. Temperatures from 20° to 150° C., especially from 40° to 80° C. have proved to be suitable. The reaction may be carried out at pressures below or above normal pressure, e.g. at 10-3 to 10-5 bar. Normal pressure is preferred.
The water moist ion exchangers may be dried before their use according to the invention by means of heat (20° to 150° C.), optionally under vacuum (up to 10-5 bar) or optionally by washing with hydrophilic organic liquids such as alcohols (e.g. methanol, ethanol or propanols) or phenols or by azeotropic distillation with organic liquids such as toluene, xylene, methylene chloride, etc . . .
The ion exchange resin is then rinsed with the phenol required for the preparation of the bisphenol and the bisphenol which is to be converted is dissolved in this medium at temperatures above the melting point of the phenol. The reaction mixture obtained after the reaction of bisphenol and phenol may be worked up by the usual methods such as distillation, crystallization, etc . . .
The process may be carried out continuously or batch wise.
The bisphenol or mixture of bisphenols prepared by this process may be used for known applications and is suitable in particular for the preparation of polycarbonates and of polymer alloys obtainable from the polycarbonates.
EXAMPLE 1
228 g of bisphenol A (1 mol), 1464 g of 2,6-dimethyl phenol (12 mol), about 250 g of ion exchange resin Lewatit (manufacturers Bayer AG) moist with dimethyl phenol and 0.68 g of β-mercaptopropionic acid are stirred together in a conventional laboratory apparatus at about 60° C. and the progress of conversion is monitored gas chromatographically. By the end of 6 hours, about 25% of 3,5-dimethyl-4,4'-dihydroxydiphenyl-2,2-propane, about 10% of 3,3'-5,5'-tetramethyl-4,4'-dihydroxydiphenyl-2,2-propane and about 5% of 1,1,3,4,6-pentamethyl-3-(3,5-dimethyl-4-hydroxyphenyl)-indan-5-ol have formed from the bisphenol A. White crystals of the bisphenol mixture described above are obtained after removal of the ion exchanger by filtration and distillation of the phenol.
EXAMPLE 2
228 g of bisphenol A (1 mol), 1296 g of o-cresol (12 mol), about 250 g of o-cresol-moist ion exchange resin Lewatit SC 102® (manufacturer Bayer AG) and 0.68 g of β-mercaptopropionic acid are stirred together in a conventional laboratory apparatus at about 60° C. and the progress of conversion is monitored gas chromatographically. By the end of 5 hours, about 25% of the bisphenol A has been converted into 3-methyl-4,4'-dihydroxydiphenyl-2,2-propane, 20% has been converted into 3,3'-dimethyl-4,4'-dihydroxydiphenyl-2,2-propane and about 5% has been converted into indans. White crystals of the bisphenol mixture described above are obtained after the ion exchanger has been filtered off and the phenol distilled off.

Claims (3)

What is claimed is:
1. In the process for isomerization of bisphenols in the presence of phenols and catalyst, the improvement comprises contacting a bisphenol of the formula ##STR6## with a phenol of the formula ##STR7## and a catalyst selected from the group consisting of protonic acids, Lewis acids and acid ion exchange resins,
wherein
R1 to R8 are the same or different and each is, independent of the others, hydrogen or alkyl having 1-12 carbon atoms,
X is alkylidene having 1-12 carbon atoms or cycloalkylidene having 3-12 carbon atoms, with X in the ortho or para position to the --OH,
R11 to R14 are the same or different and each is, independent of the others, .Iadd.hydrogen, .Iaddend.alkyl having 1-12 carbon atoms, halogen, aryl having 6-24 carbon atoms, alkoxy having 1-12 carbon atoms or cycloalkyl having 5-30 carbon atoms.
2. The process according to claim 1 wherein the catalyst is an acid ion exchange resin, which is the reaction product of styrene/divinyl benzene copolymers with a sulfonating agent, having particle sizes of 0.3 to 1.5 mm in diameter and having a total capacity of acid functions in a water-moist form with a water content of about 75-85% by weight ranging from 0.7 to 2.1 m val/ml of ion exchanger based on one gram of dry exchanger.
3. Bisphenol mixtures obtained by the process according to claim 1.
US08/027,734 1988-08-16 1993-02-01 Isomerization of bisphenols Expired - Lifetime USRE34626E (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US08/027,734 USRE34626E (en) 1988-08-16 1993-02-01 Isomerization of bisphenols

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE3827643A DE3827643A1 (en) 1988-08-16 1988-08-16 ISOMERIZATION OF BISPHENOLS
DE3827643 1988-08-16
US07/389,354 US5015784A (en) 1988-08-16 1989-08-03 Isomerization of bisphenols
US08/027,734 USRE34626E (en) 1988-08-16 1993-02-01 Isomerization of bisphenols

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US07/389,354 Reissue US5015784A (en) 1988-08-16 1989-08-03 Isomerization of bisphenols

Publications (1)

Publication Number Publication Date
USRE34626E true USRE34626E (en) 1994-05-31

Family

ID=6360878

Family Applications (2)

Application Number Title Priority Date Filing Date
US07/389,354 Ceased US5015784A (en) 1988-08-16 1989-08-03 Isomerization of bisphenols
US08/027,734 Expired - Lifetime USRE34626E (en) 1988-08-16 1993-02-01 Isomerization of bisphenols

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US07/389,354 Ceased US5015784A (en) 1988-08-16 1989-08-03 Isomerization of bisphenols

Country Status (4)

Country Link
US (2) US5015784A (en)
EP (1) EP0355513B1 (en)
JP (1) JP2723625B2 (en)
DE (2) DE3827643A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015107467A1 (en) 2014-01-14 2015-07-23 Sabic Global Technologies B.V. Methods of manufacture of 2-hydrocarbyl-3,3-bis(hydroxyaryl)phthalimidines

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3827643A1 (en) * 1988-08-16 1990-02-22 Bayer Ag ISOMERIZATION OF BISPHENOLS
EP0782978B1 (en) * 1996-01-05 2000-04-05 General Electric Company Method for preparing and purifying 1,1,1-tris(4-hydroxyphenyl)ethane
US5874644A (en) * 1996-04-12 1999-02-23 Gammill; Ben Method and system for bisphenol a production using controlled turbulence
US5959158A (en) * 1996-04-12 1999-09-28 Gammill; Ben Method and system for bisphenol a production using water
US5763686A (en) * 1996-12-16 1998-06-09 General Electric Company Method for preparing 1,1,1-tris(4-hydroxyphenyl)ethane
US6433236B1 (en) * 2000-03-21 2002-08-13 Arteva North America S.A.R.L. Acid catalyzed isomerization of substituted diaryls
US6960697B2 (en) * 2002-03-13 2005-11-01 Mitsubishi Chemical Corporation System and method of producing bisphenol-A (BPA)
US20050075520A1 (en) * 2002-03-13 2005-04-07 O'young Drow Lionel System and method of producing bisphenol-A (BPA) using two stage crystallization
US8735634B2 (en) 2011-05-02 2014-05-27 Sabic Innovative Plastics Ip B.V. Promoter catalyst system with solvent purification
US9290618B2 (en) 2011-08-05 2016-03-22 Sabic Global Technologies B.V. Polycarbonate compositions having enhanced optical properties, methods of making and articles comprising the polycarbonate compositions
US9490405B2 (en) 2012-02-03 2016-11-08 Sabic Innovative Plastics Ip B.V. Light emitting diode device and method for production thereof containing conversion material chemistry
US9287471B2 (en) 2012-02-29 2016-03-15 Sabic Global Technologies B.V. Polycarbonate compositions containing conversion material chemistry and having enhanced optical properties, methods of making and articles comprising the same
WO2013130606A2 (en) 2012-02-29 2013-09-06 Sabic Innovative Plastics Ip B.V. Polycarbonate made from low sulfur bisphenol a and containing converions material chemistry, and articles made therefrom
US9346949B2 (en) 2013-02-12 2016-05-24 Sabic Global Technologies B.V. High reflectance polycarbonate
WO2014066784A1 (en) 2012-10-25 2014-05-01 Sabic Innovative Plastics Ip B.V. Light emitting diode devices, method of manufacture, uses thereof
US9553244B2 (en) 2013-05-16 2017-01-24 Sabic Global Technologies B.V. Branched polycarbonate compositions having conversion material chemistry and articles thereof
CN105492519B (en) 2013-05-29 2018-03-09 沙特基础全球技术有限公司 The lighting apparatus of thermoplasticity optical transport product with colour stable
CN113574090A (en) * 2019-03-14 2021-10-29 三菱化学株式会社 Bisphenol composition and polycarbonate resin

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1066137A (en) * 1964-07-24 1967-04-19 Shawinigan Chem Ltd Reduction of isomeric impurity in diphenylol propane
GB1474168A (en) * 1973-07-03 1977-05-18 Shell Int Research Isomerization of bisphenol
US4156790A (en) * 1978-04-10 1979-05-29 General Electric Company Isomerization of dihydroxydiphenyl compounds
JPS5798229A (en) * 1980-12-10 1982-06-18 Mitsubishi Chem Ind Ltd Recovering method of bisphenol a
JPS57114540A (en) * 1981-01-06 1982-07-16 Mitsubishi Chem Ind Ltd Isomerization of bisphenols
JPS59122434A (en) * 1982-12-28 1984-07-14 Cosmo Co Ltd Preparation of p-p bisphenolmethane or ethane
JPS61118335A (en) * 1984-11-12 1986-06-05 Mitsubishi Petrochem Co Ltd Method for producing 2,2-bis(4-hydroxyaryl)propanes
JPS6229543A (en) * 1985-08-01 1987-02-07 Mitsui Toatsu Chem Inc Production of beta,gamma-unsaturated alkenyl group-substituted phenol
JPS62201833A (en) * 1986-02-28 1987-09-05 Mitsui Toatsu Chem Inc Isomerization of bisphenol compound
US4814520A (en) * 1986-09-02 1989-03-21 Idemitsu Petrochemical Company Limited Process for producing 2,2-bis(4'hydroxyphenyl) propanes
US4822923A (en) * 1987-10-19 1989-04-18 Shell Oil Company Isomerization of by-products of bis-phenol synthesis
US4825010A (en) * 1987-10-19 1989-04-25 Shell Oil Company Isomerization of by-products of bi-phenol synthesis
US5015784A (en) * 1988-08-16 1991-05-14 Bayer Aktiengesellschaft Isomerization of bisphenols

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01118335A (en) * 1987-10-30 1989-05-10 Jidosha Imono Kk Manufacture of mold
DE68901666T2 (en) * 1988-03-15 1993-02-11 Aleados Del Cobres S A Alecosa HEAT CONTAINER FOR LIQUIDS, FAT PRODUCTS, GELS AND SIMILAR.
JPH02201833A (en) * 1989-01-31 1990-08-10 Meidensha Corp Magnetic driving type electrode for vacuum interrupter

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1066137A (en) * 1964-07-24 1967-04-19 Shawinigan Chem Ltd Reduction of isomeric impurity in diphenylol propane
GB1474168A (en) * 1973-07-03 1977-05-18 Shell Int Research Isomerization of bisphenol
US4156790A (en) * 1978-04-10 1979-05-29 General Electric Company Isomerization of dihydroxydiphenyl compounds
JPS5798229A (en) * 1980-12-10 1982-06-18 Mitsubishi Chem Ind Ltd Recovering method of bisphenol a
JPS57114540A (en) * 1981-01-06 1982-07-16 Mitsubishi Chem Ind Ltd Isomerization of bisphenols
JPS59122434A (en) * 1982-12-28 1984-07-14 Cosmo Co Ltd Preparation of p-p bisphenolmethane or ethane
JPS61118335A (en) * 1984-11-12 1986-06-05 Mitsubishi Petrochem Co Ltd Method for producing 2,2-bis(4-hydroxyaryl)propanes
JPS6229543A (en) * 1985-08-01 1987-02-07 Mitsui Toatsu Chem Inc Production of beta,gamma-unsaturated alkenyl group-substituted phenol
JPS62201833A (en) * 1986-02-28 1987-09-05 Mitsui Toatsu Chem Inc Isomerization of bisphenol compound
US4814520A (en) * 1986-09-02 1989-03-21 Idemitsu Petrochemical Company Limited Process for producing 2,2-bis(4'hydroxyphenyl) propanes
US4822923A (en) * 1987-10-19 1989-04-18 Shell Oil Company Isomerization of by-products of bis-phenol synthesis
US4825010A (en) * 1987-10-19 1989-04-25 Shell Oil Company Isomerization of by-products of bi-phenol synthesis
US5015784A (en) * 1988-08-16 1991-05-14 Bayer Aktiengesellschaft Isomerization of bisphenols

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015107467A1 (en) 2014-01-14 2015-07-23 Sabic Global Technologies B.V. Methods of manufacture of 2-hydrocarbyl-3,3-bis(hydroxyaryl)phthalimidines

Also Published As

Publication number Publication date
US5015784A (en) 1991-05-14
EP0355513B1 (en) 1994-09-21
DE3827643A1 (en) 1990-02-22
DE58908398D1 (en) 1994-10-27
EP0355513A3 (en) 1990-12-27
JPH0283345A (en) 1990-03-23
JP2723625B2 (en) 1998-03-09
EP0355513A2 (en) 1990-02-28

Similar Documents

Publication Publication Date Title
USRE34626E (en) Isomerization of bisphenols
US7112702B2 (en) Process for the synthesis of bisphenol
US5302774A (en) Process for the production of bisphenols
US8263521B2 (en) Process for producing bisphenol A
US5914431A (en) Cocatalysts for the synthesis of bisphenols
US5212206A (en) Ion exchange modified with mercapto amines
CA2090655A1 (en) Process for preparing a bisphenol
US5284981A (en) Ion exchangers modified with mercapto amines
US4931594A (en) Method for making aromatic bisphenols
US4912263A (en) Ionic exchangers modified with thiazolines
US4847432A (en) Method for the purification of ion exchange resins used in the production of bisphenol A
JPH09176068A (en) Method for producing tris (hydroxyphenyl) compound using ion exchange resin
WO1997008122A1 (en) Isomerization of bisphenols
CA1318331C (en) Ion exchangers modified with mercapto amines
US3173891A (en) Polycarbonate process
KR100554772B1 (en) Method for manufacturing bisphenol
US20050119111A1 (en) Catalytic reactions using thermally stable resins
US7304189B2 (en) Methods for preparing 1,1,1-tris(4-hydroxyphenyl)alkanes
EP3243810B1 (en) Method for producing a bisphenol
WO2006012312A1 (en) Methods for preparing 1, 1, 1 -tri s(4-hydroxyphenyl)alkanes
EP4243980A1 (en) Catalyst system and process for producing bisphenol-a
US4467121A (en) Fluorinated diphenols and method for their preparation
JPS63139142A (en) Production of monoaralkylated phenols
JPS6368534A (en) Novel bisphenols and production thereof

Legal Events

Date Code Title Description
FPAY Fee payment

Year of fee payment: 8

FPAY Fee payment

Year of fee payment: 12