Isopropylidene Diphenol Produced Patents (Class 568/728)
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Publication number: 20030125587Abstract: There is disclosed a process for producing bisphenol A by continuously supplying phenol to a first-stage reactor in a continuous multi-stage fixed-bed reaction system composed of at least two reactors each filled in with a cation exchange resin as a catalyst, and continuously supplying acetone separately to each of the reactors, characterized by arranging a reactor which is filled in with a fresh or regenerated cation exchange resin on the final stage in the case of replacing the most seriously deteriorated cation exchange resin in catalytic activity with the fresh or regenerated cation exchange resin, and operating the final stage reactor so that the ratio R of the feed rate of acetone to the consumption rate thereof falls within more than one to less than 3. The above process makes it possible to efficiently produce bisphenol A having favorable hue, while maintaining the acetone feed rate at a relatively low level.Type: ApplicationFiled: October 30, 2002Publication date: July 3, 2003Inventor: Tetsuya Saruwatari
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Patent number: 6586637Abstract: Acetone and phenol are reacted in the presence of an acid-type ion exchange resin. The reaction mixture obtained from the reaction is subjected to a reduced-pressure distillation to recover bisphenol A as a fraction discharged from the bottom of a distillation column. Before the reaction, the acid-type ion exchange resin is washed with phenol to produce a phenol solution. The phenol solution is distilled together with a fraction obtained from the top of a distillation column. The bisphenol A produced in the process exhibits a stable hue.Type: GrantFiled: September 7, 2001Date of Patent: July 1, 2003Assignee: Idemitsu Petrochemical Co., Ltd.Inventor: Masahiro Iwahara
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Patent number: 6586640Abstract: A process for the manufacture of a hydroxy-substituted organic compound comprising decomposing an organic hydroperoxide, preferably a compound of the formula Ar—C(CH3)2O2H, wherein Ar is a substituted or unsubstituted mononuclear or polynuclear aromatic group. The decomposition is carried out in the presence of a catalyst comprising highly fluorinated polymer having sulfonic acid groups with the catalyst being in the form of particles of which at least about 20 weight % have a particle size less than about 300 &mgr;m. Cumene hydroperoxide can be decomposed in the process to phenol and acetone which can be reacted to form bisphenol A in the presence of the same catalyst that was used for the decomposition.Type: GrantFiled: June 20, 2002Date of Patent: July 1, 2003Assignee: E. I. du Pont de Nemours and CompanyInventors: Ralph Birchard Lloyd, Qun Sun, Mark Andrew Harmer, Edward George Howard, Jr.
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Publication number: 20030120120Abstract: Provided is a production process for high quality bisphenol A which is reduced in a sulfonic acid-containing heavy matter contained in the product and which is improved in a hue. In an after-treating step for a reaction mixed solution obtained by condensing excess phenol with acetone in the presence of an acid catalyst, a filtering step by a filter is provided at least in one step between a step for dissolving an adduct of bisphenol A and phenol by using a phenol-containing solution and a step for crystallizing and separating the above adduct from this solution.Type: ApplicationFiled: October 31, 2002Publication date: June 26, 2003Inventors: Kazuyuki Hirano, Ken Fujimoto
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Publication number: 20030114716Abstract: Acetone and phenol are reacted over a strong acid catalyst in the presence of lower alcohol. The lower alcohol can be methanol, ethanol, n-propanol, iso-propanol, n-butanol, sec-butanol, tertiary-butanol and iso-butanol. For each mole of acetone one mole or more of lower alcohol is provided, and one to four moles of lower alcohol are preferred.Type: ApplicationFiled: August 30, 2002Publication date: June 19, 2003Inventor: Barrie W. Jackson
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Publication number: 20030088130Abstract: This disclosure relates to a method for producing and using catalysts in the production of bisphenols, and in particular to a method for producing catalysts which contain poly-sulfur mercaptan promoters, and using these catalysts in the production of bisphenol-A and its derivatives.Type: ApplicationFiled: September 18, 2001Publication date: May 8, 2003Applicant: General Electric Company.Inventors: Jimmy Lynn Webb, James Lawrence Spivack
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Publication number: 20030055295Abstract: Method for producing multiple chemical reactions and for rapid screening of chemicals, catalysts, process conditions and the like is disclosed. The method includes the steps of providing an array of reactor vessels and reactants; loading each reactor vessel with at least one reactant; and allowing the reactions to proceed for a predetermined time interval. A volume increment is withdrawn from each reactor vessel and a volume increment of at least one reactant is added to each reactor vessel in the array. The steps of volume increment withdrawal and addition are repeated after successive time intervals until the reactions reach a substantially steady state. The loading, withdrawal, and addition steps are performed by liquid or solid handling robots. In one embodiment, the volume increment withdrawal occurs before, after, or contemporaneously with the volume increment addition.Type: ApplicationFiled: September 4, 2002Publication date: March 20, 2003Applicant: General Electric CompanyInventors: William Patrick Flanagan, James Lawrence Spivack, Cheryl Lynn Sabourin
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Patent number: 6534686Abstract: This disclosure relates to a method for producing and using catalysts in the production of bisphenols, and in particular to a method for producing catalysts which contain attached mercaptan promoters, and using these catalysts in the production of bisphenol-A and its derivatives.Type: GrantFiled: September 18, 2001Date of Patent: March 18, 2003Assignee: General Electric CompanyInventors: Jimmy Lynn Webb, James Lawrence Spivack
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Publication number: 20030050514Abstract: A method for producing a bisphenol is disclosed. The method entails reacting in at least one first reactant selected from a first group consisting of phenol and substituted phenols with at least one second reactant selected from a second group consisting of ketones and diols, in the presence of hydrogen chloride catalyst and volatile sulphur compound having an SH bond as co-catalyst. The reaction product is a mixture that contains bisphenol, first reactant and second reactant. The catalyst and co-catalyst and water of reaction are separated by distillation. The method is characterized by the high reaction rates and selectivities.Type: ApplicationFiled: July 16, 2002Publication date: March 13, 2003Inventors: Tony Van Osselaer, Werner Verhoeven, Domien Sluyts
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Publication number: 20030050513Abstract: A process for the manufacture of a hydroxy-substituted organic compound comprising decomposing an organic hydroperoxide, preferably a compound of the formula Ar—C(CH3)2O2H, wherein Ar is a substituted or unsubstituted mononuclear or polynuclear aromatic group. The decomposition is carried out in the presence of a catalyst comprising highly fluorinated polymer having sulfonic acid groups with the catalyst being in the form of particles of which at least about 20 weight % have a particle size less than about 300 &mgr;m. Cumene hydroperoxide can be decomposed in the process to phenol and acetone which can be reacted to form bisphenol A in the presence of the same catalyst that was used for the decomposition.Type: ApplicationFiled: June 20, 2002Publication date: March 13, 2003Inventors: Ralph Birchard Lloyd, Qun Sun, Mark Andrew Harmer, Edward George Howard
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Publication number: 20030045758Abstract: A method of producing a chemical reaction is provided. In the practice of one embodiment of the invention, the method includes the steps of providing a reaction vessel and reactants; placing at least one of the reactants in the reaction vessel; and allowing the reaction to proceed for a time interval. A volume increment of at least one of the reactants is withdrawn from the reaction vessel, and a volume increment of at least one of the reactants is added to the reaction vessel. The volume increment withdrawal/addition is repeated after successive time intervals until the reaction reaches a substantially steady state. In various alternative embodiments, the volume increment withdrawal can take place before, after, or contemporaneously with the volume increment addition.Type: ApplicationFiled: June 26, 2002Publication date: March 6, 2003Applicant: General Electric CompanyInventors: William Patrick Flanagan, Cheryl Lynn Sabourin, James Lawrence Spivack
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Patent number: 6512148Abstract: A process for the production of bisphenol A, including providing a melt of a crystalline adduct of bisphenol A and phenol, contacting the melt with a cation donating solid to neutralize the strong acid therewith, and then heating the melt to vaporize and remove phenol from the melt.Type: GrantFiled: September 26, 2001Date of Patent: January 28, 2003Assignee: Mitsubishi Chemical CorporationInventors: Susumu Yamamoto, Atsumi Kukidome, Makoto Nomura, Keiji Maehara, Kenji Nagahama
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Publication number: 20030013928Abstract: In the production of bisphenol A by condensation of phenol and acetone with the use of a cation exchange resin as a catalyst and a free mercaptan as a promoter, the superficial velocity of raw material within the reaction column packed with a cation exchange resin is controlled to be in the range of 1.5 m/hr to 6 m/hr.Type: ApplicationFiled: August 27, 2002Publication date: January 16, 2003Inventor: Tetsuya Saruwatari
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Publication number: 20030013927Abstract: In the production of bisphenol A by condensation of phenol and acetone with the use of a cation exchange resin as a catalyst and optionally a free mercaptan as a promoter, the degree of conversion of phenol is maintained by increasing the molar ratio of acetone/phenol with the deterioration of the cation exchange resin.Type: ApplicationFiled: August 20, 2002Publication date: January 16, 2003Inventor: Tetsuya Saruwatari
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Publication number: 20030013926Abstract: There is disclosed a method of producing bisphenol A, in which bisphenol A is produced by condensation of phenol and acetone with the use of a cation exchange resin as a catalyst and a free mercaptan as a promoter, comprising feeding phenol and acetone to a multi-stage reactor in which at least two fixed bed-type adiabatic reactors packed with the cation exchange resin are arranged in series and a heat exchanger is provided at an inlet of each of the reactors, and controlling the temperature within each of the reactors so as not to exceed 90° C.Type: ApplicationFiled: August 16, 2002Publication date: January 16, 2003Inventor: Tetsuya Saruwatari
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Publication number: 20030013925Abstract: There is provided a process for producing bisphenol A exhibiting a stable hue without undesired coloration even when treated at an elevated temperature. In the process for producing bisphenol A by reacting acetone with phenol in the presence of an acid-type ion exchange resin as a catalyst and then subjecting the reaction mixture to a reduced-pressure distillation to recover the bisphenol A from a fraction discharged from a bottom of distillation column, said process comprises: washing said acid-type ion exchange resin filled in a reactor with phenol before used in the reaction; and distilling a phenol solution obtained after the washing together with a fraction obtained from a top of the distillation column to recover phenol.Type: ApplicationFiled: September 7, 2001Publication date: January 16, 2003Inventor: Masahiro Iwahara
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Publication number: 20020177740Abstract: A process for the manufacture of a polyphenol compound such as bisphenol-A by introducing into a reaction zone a phenolic compound reactant, a carbonyl compound reactant, and a catalyst promoter comprising a dithioketal compound, and reacting the ingredients within the reaction zone in the presence of an acid catalyst.Type: ApplicationFiled: April 13, 2001Publication date: November 28, 2002Inventors: David Palmer, Pui Kwan Wong
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Patent number: 6486364Abstract: The acid catalyzed condensation of phenol with acetone in the presence of a thiol promoter to produce bisphenol A is found to occur with greater overall selectivity when the catalyst employed is an amine modified acidic resin catalyst. Amine modified acidic resin catalysts are prepared from acidic resins such as sulfonated polystyrene by neutralization of a portion of the acidic functional groups present with an amine such as pyridine. Where the thiol promoter is itself an amine the use of an amine such as pyridine as the modifying agent reduces the amount of thiol promoter required to achieve high selectivity.Type: GrantFiled: December 19, 2000Date of Patent: November 26, 2002Assignee: General Electric CompanyInventor: James Lawrence Spivack
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Patent number: 6486363Abstract: The present invention relates to a process for the manufacture of bis(4-hydroxyaryl)alkanes by heterogeneous acid-catalyzed reaction of aromatic hydroxy compounds with ketones in reactors connected in series, which in the direction of advancing conversion are operated with rising temperature and optionally with increasing loading.Type: GrantFiled: July 12, 1996Date of Patent: November 26, 2002Assignee: Bayer AktiengesellschaftInventors: Klaus Berg, Hans-Josef Buysch, Alfred Eitel, Gerhard Fennhoff, Georg Malamet, Clauss Wulff
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Patent number: 6486222Abstract: The invention is a catalytic ion exchange resin bed with low pressure drop, low catalyst breakage and low catalyst deactivation as well as an improved process for the production of bisphenol A employing such a catalytic ion exchange resin bed.Type: GrantFiled: April 9, 2001Date of Patent: November 26, 2002Assignee: General Electric CompanyInventors: Gaylord M. Kissinger, Sheldon J. Shafer, Harish R. Acharya, Rudy Francois Alain J. Peemans, Eduard H. Schlarmann
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Patent number: 6465697Abstract: A process for the manufacture of a polyphenol compound such as bisphenol-A by introducing into a reaction zone a phenolic compound reactant, a carbonyl compound reactant, and a catalyst promoter comprising a dithioketal compound, and reacting the ingredients within the reaction zone in the presence of an acid catalyst.Type: GrantFiled: April 13, 2001Date of Patent: October 15, 2002Assignee: Resolution Performance Products LLCInventors: David Palmer, Pui Kwan Wong
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Patent number: 6459004Abstract: A cleavage method of bisphenols capable of yielding a product containing high-purity isopropenylphenol and phenol is disclosed, including (1) a cleavage step of supplying the mixture containing bisphenols together with chroman derivatives and flavan derivatives formed as by-products in the production process of bisphenols to a cleaving vessel and carrying out a cleavage reaction in the presence of a basic or acidic catalyst at a temperature of from 150 to 260° C. under a reduced pressure condition of not higher than 300 mmHg, (2) a distillation step of supplying the cleavage step product formed in the cleavage step in a vapor state to a distillation column and distilling at a temperature of from 130 to 200° C. under a reduced pressure condition of not higher than 300 mmHg, and (3) a reflux step of condensing the distillate from the distillation step, refluxing a part thereof to the distillation step at a reflux ratio of from 0.01 to 3, and discharging out the residue from the system.Type: GrantFiled: February 23, 2001Date of Patent: October 1, 2002Assignee: Mitsui Chemicals, Inc.Inventors: Yuzo Ono, Kouichirou Terada, Kiyoshi Mizuma, Mikio Shibasaki
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Patent number: 6429343Abstract: The present invention provides a process for producing bisphenol A which is capable of prolonging the life of an acid-type ion exchange resin partially modified with a sulfur-containing amine compound as catalyst, and increasing the yield of bisphenol A per unit quantity of the catalyst. There is disclosed a process for producing bisphenol A by reacting acetone with phenol in the presence of an acid-type ion exchange resin partially modified with a sulfur-containing amine compound as catalyst and alkylmercaptan as co-catalyst, said process comprising: conducting said reaction using a multi-stage reaction apparatus comprising at least two individual reactors connected in series to each other, wherein the molar ratio of total alkylmercaptan to total acetone and the molar ratio of total acetone to phenol are increased as the conversion rate of the phenol is decreased.Type: GrantFiled: August 21, 2001Date of Patent: August 6, 2002Assignee: Idemitsu Petrochemical Co., Ltd.Inventor: Masahiro Iwahara
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Patent number: 6414200Abstract: Silylmethanethiols have been found to be useful promoters in the acid catalyzed condensation reaction between phenol and acetone to afford bisphenol A. Silylmethanethiols provide improvements in both the rate and selectivity of bisphenol A formation relative to known thiol promoters such as 3-mercaptopropionic acid or hexanethiol.Type: GrantFiled: December 19, 2000Date of Patent: July 2, 2002Assignee: General Electric CompanyInventors: James Lawrence Spivack, Jimmy Lynn Webb, Victoria Jean Eddy-Helenek, Joseph Richard Wetzel
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Patent number: 6414199Abstract: Provided is a method of producing bisphenol A in which the life of the acid-type ion-exchange resin used as a catalyst can be prolonged. The method comprises reacting phenol and acetone in the presence of an acid-type ion-exchange resin serving as a catalyst and an alkylmercaptan serving as a promoter to give bisphenol A, in which three or more reactors connected in series are used and all of phenol, all of an alkylmercaptan and a part of acetone are fed into the first reactor while the remaining acetone, divided into plural portions, is into all the second to the last reactors.Type: GrantFiled: December 13, 2000Date of Patent: July 2, 2002Assignee: Idemitsu Petrochemical Co., Ltd.Inventor: Tetsuya Saruwatari
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Patent number: 6329556Abstract: This invention relates to a process for preparing bisphenol A by the condensation of phenol with acetone in the presence of cation exchange resin obtained by sulfonating copolymers of monovinyl monomers mainly consisting of styrenes and divinyl monomers as crosslinking agent while using divinylbiphenyl and divinylbenzene mainly as said divinyl monomers and controlling the molar ratio of divinylbiphenyl to divinylbenzene at 10/0-2/8. The cation exchange resin to be used as catalyst in the condensation reaction shows a long life, maintains the production of bisphenol A over a long period of time, possesses high strength and is useful for economical and advantageous production of bisphenol A.Type: GrantFiled: November 29, 2000Date of Patent: December 11, 2001Assignee: Nippon Steel Chemical Co., Ltd.Inventors: Katsuhiko Sakura, Shingo Ueda, Genki Takeuchi, Shyouta Shirasaka, Toshikazu Maruyama, Yasuharu Hukuda, Taketoshi Kitoh, Morio Kimura
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Patent number: 6307111Abstract: The present invention relates to a process for the continuous production of dihydroxydiarylalkanes (bisphenols) by the reaction of fresh phenol, phenol and isoalkenylphenol from the decomposition of by-products, and ketone. In this process the bulk of the bisphenol is recovered from the reaction mixture by crystallization and the mother liquor obtained is freed from phenol by distillation. The phenol is returned to the reaction and the bottoms obtained during the distillation are decomposed in a reactive rectification after addition of a basic catalyst. The phenol and isoalkenylphenol leaving at the top are led back into the reaction; the bottoms from the first reactive column are acidified and in a second reactive rectification, in the presence of an acid catalyst, are further decomposed into phenol, which distils off and is reused in the reaction, and bottoms, which are disposed of.Type: GrantFiled: November 12, 1999Date of Patent: October 23, 2001Assignee: Bayer AktiengesellschaftInventors: Gerhard Fennhoff, Hans-Josef Buysch, Gerd Fengler
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Patent number: 6303835Abstract: Phenol and isopropenylphenol are recovered from BPA tars by sparging the fluidized BPA tar while heating in the presence of a basic catalyst. Sparging dramatically increases the efficiency of phenol and isopropenylphenol recovery. Recovered isopropenylphenol may be converted to bisphenol A in the distillate by reaction with phenol and an acidic catalyst.Type: GrantFiled: September 11, 2000Date of Patent: October 16, 2001Assignee: General Electric CompanyInventors: Sheldon Jay Shafer, Eric James Pressman, Julia Lam Lee
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Patent number: 6300528Abstract: Cleaning of a reactor used in the production of bisphenols is enhanced by heating the reactor wall, for example by the introduction of steam into the shell surrounding the reactor. The steam heats the wall which lies between the shell and the interior reaction chamber, and thus facilitates melting/dissolution of bisphenol:phenol adduct that has formed on the wall on the inside of reaction chamber. The steam is introduced for a period of at least 5 minutes, and preferably for a period of from 5 to 60 minutes. In a variation of this method, a solubility-increasing composition is introduced into the reaction chamber to increase the solubility of the bisphenol during the introduction of steam. Suitable solubility-increasing compositions include hydrochloric acid and/or water, or a mixture of acetone and phenol.Type: GrantFiled: April 3, 2000Date of Patent: October 9, 2001Assignee: General Electric CompanyInventors: Gerrit Op Den Dries, Martin Jaco Soeters, Marcellinus Adrianus Klaverveld, Eduard Hendricus Schlarmann, Guido Theodorus Fridiswidus Maria Van Dooremal
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Patent number: 6294702Abstract: The present invention relates to a process for the continuous production of dihydroxydiphenylalkanes (bisphenols) by the reaction of fresh phenol, and of phenol obtained from the cracking of by-products, with isoalkenylphenol and ketone. In the course of this process, the reaction mixture is worked up by distillation and a high purity bisphenol is produced. The bottom products and distillates containing the by-products are cracked under basic conditions and optionally thereafter under acidic conditions. The cracked products, which substantially consist of isoalkenylphenol and phenol, are recycled, optionally after purification, with the phenol obtained during the purification of bisphenol, to the reaction to form bisphenol, and the residue obtained from cracking is disposed of.Type: GrantFiled: December 13, 1999Date of Patent: September 25, 2001Assignee: Bayer AktiengesellschaftInventors: Gerhard Fennhof, Hans-Josef Buysch, Gerd Fengler, Tony van Osselaer
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Patent number: 6288284Abstract: The present invention relates to a process for the production of bis(4-hydroxyaryl)alkanes by an acid-catalyzed reaction between aromatic hydroxy compounds and ketones, in which the temperature, ketone content and water content of a liquid reaction mixture are adjusted by means of a suitably composed gas phase.Type: GrantFiled: July 3, 2000Date of Patent: September 11, 2001Assignee: Bayer AktiengesellschaftInventors: Rob Eek, Kaspar Hallenberger, Christine Mendoza-Frohn, Georg Ronge, Gerhard Fennhoff, Domien Sluyts, Werner Verhoeven
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Patent number: 6245951Abstract: In a semicontinuous method for manufacturing bisphenols, reduced fouling in the pre-reactor is achieved by using two or more prereactors are used to continuously condense the dihydric phenol and the ketone or aldehyde to produce a partial reaction product in which the reaction of the dihydric phenol and the ketone or aldehyde is 10 to 70% complete. This partial reaction product is continuously removed from the pre-reactors, combined and introduced to a batchwise completion reactor. A stream of water or aqueous hydrochloric acid is added in alternating intervals to the pre-reactors, such that one is being cleaned by shifting the solubility of the bisphenol product at the same time that the other(s) continue to product a normal product stream which includes seed crystals for enhancing the performance of the batchwise completion reactor.Type: GrantFiled: October 12, 1999Date of Patent: June 12, 2001Assignee: General Electric CompanyInventors: Rudy Peemans, Jan-Peter Visser, Hendrik Herman Caré, Edwin Van Der Schuit, Robbert Vos
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Patent number: 6211417Abstract: The present invention relates to a process for the production of bis-(4-hydroxyaryl)-alkanes by a heterogeneously catalyzed reaction of aromatic hydroxy compounds with ketones in at least two reactors connected in series, which, as the reaction progresses, are operated at higher temperatures, wherein the total quantity of ketone is divided between the individual reactors in such a manner that the higher is the temperature of the particular reactor, the smaller is the proportion per reactor, the highest possible reactor loading is maintained and the temperatures and temperature gradients are kept as low as possible.Type: GrantFiled: July 12, 1999Date of Patent: April 3, 2001Assignee: Bayer AktiengesellschaftInventors: Gerd Fengler, Hans-Josef Buysch, Frieder Heydenreich, Rob Eek, Gerhard Fennhoff
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Patent number: 6203612Abstract: An alternative and improved method for cleaning cooling and/or crystallization surfaces of a crystallizer fouled with a crystallized bisphenol as a result of processing a slurry derived from the production of bisphenol is provided. The method includes the steps of: (a) draining from 20 to 80%, and preferably about 50% of the slurry from the crystallizer; (b) replacing the drained slurry with a solvent comprising phenol, thereby forming a diluted slurry; (c) increasing the temperature in the crystallizer to a temperature at which the crystallized bisphenol is dissolved in the diluted slurry, and then rapidly cooling the diluted slurry to a temperature of 45 to 55° C.; and (d) adding a seed slurry containing solid bisphenol at a concentration of 5 to 30%. The seed slurry has a temperature of 45 to 55° C. and is added until conditions are established at which bisphenol crystals added to the crystallizer do not redissolve.Type: GrantFiled: March 30, 2000Date of Patent: March 20, 2001Assignee: General Electric CompanyInventors: Rudy Peemans, Jan Huibert Weijland, Mourice Van Sintemaartensdijk
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Patent number: 6191316Abstract: The present invention relates to a process for working up the residual mother liquors from the production of dihydroxydiarylalkanes (bisphenols) discharged from the process once the bisphenol has been separated.Type: GrantFiled: November 12, 1999Date of Patent: February 20, 2001Assignee: Bayer AktiengesellschaftInventors: Gerhard Fennhoff, Hans-Josef Buysch, Gerd Fengler
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Patent number: 6133486Abstract: The disclosure is of a process for recovering valuable phenol and acetone from by-products of the condensation of phenol and a ketone from a mother liquor obtained for example upon crystallization of a 1:1 adduct of phenol and bisphenol, the mother liquor containing phenol, bisphenol, isomers, contaminant by-products of the condensation reaction of phenol with the ketone and acidic impurities. The mother liquor is distilled/evaporated leaving a tarry residue, which is the feedstock for the process of the invention. The recovery comprises catalytically cracking the feedstock with catalytic proportions of an aromatic sulfonic acid to extract the bisphenol-A values as phenol and acetone.Type: GrantFiled: December 30, 1998Date of Patent: October 17, 2000Assignee: General Electric CompanyInventors: Christianus J. J. Maas, Martin H. Oyevaar, Jos H. M. Graff
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Patent number: 6130359Abstract: An improved process for producing Bisphenol-A which is essentially free of sodium impurity using rotary vacuum filter pumps which utilize a liquid ring seal to effect drawing a vacuum on a Bisphenol-A/phenol slurry, the improvement is in using phenol as the liquid ring seal medium.Type: GrantFiled: September 16, 1998Date of Patent: October 10, 2000Assignee: General Electric CompanyInventor: Gaylord M. Kissinger
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Patent number: 6049014Abstract: A process for producing n-propyl bromide during the bromination of bis- or trisphenols uses non-aqueous n-propanol as the bromination solvent, providing salable yields of n-propyl bromide to accompany the brominated bisphenol or trisphlenol.Type: GrantFiled: February 19, 1998Date of Patent: April 11, 2000Assignee: Great Lakes Chemical CorporationInventors: Anne P. Noonan, Stephen C. Scherrer
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Patent number: 6013845Abstract: A reactor system for conducting chemical reactions is presented in which a reactor is operated in an upflow mode with a fixed bed catalyst and randomly distributed reactor packing therein. The reactor system and the process in which it is used exhibit plug flow behavior and are amenable to employing lightly crosslinked ion exchange resin catalysts.Type: GrantFiled: March 19, 1997Date of Patent: January 11, 2000Assignee: Shell Oil CompanyInventors: Edgar Donald Allan, Raymond Lawrence June, YeMon Chen, Robert Lawrence Blackbourn
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Patent number: 6011184Abstract: An integrated process for the preparation and recovery of BPA in pure form utilizes a series of steps to crystallize the 1:1 adduct of phenol and bisphenol-A, with periodic descaling of the crystallizer surfaces with a modified reactor/crystallizer containing 1 to 40 percent water.Type: GrantFiled: April 6, 1998Date of Patent: January 4, 2000Assignee: General Electric CompanyInventors: Johan Adrianus Aarssen, Gerrit Op Den Dries, Ad Nieuwlaat, Marcel Vieveen, Rudy Francois Alain Joseph Peemans
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Patent number: 5874644Abstract: Methods/systems for making a relatively high-purity bisphenol A product from phenol and acetone. Controlled turbulence is used to form bisphenol A adduct solids having improved physical properties. Phenol is separated from the bisphenol A product while inhibiting decomposition of bisphenol A.Type: GrantFiled: April 12, 1996Date of Patent: February 23, 1999Inventor: Ben Gammill
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Patent number: 5856589Abstract: An improvement in the continuous preparation of a bisphenol comprising maintaining the efficiency of the adduct crystallizer. The improvement comprises maintaining the Delta-T of the crystallizer at less than about 4.degree. C.Type: GrantFiled: August 8, 1997Date of Patent: January 5, 1999Assignee: General Electric CompanyInventor: Michael J. Cipullo
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Patent number: 5783733Abstract: An integrated process for the preparation and recovery of a bisphenol based on the condensation reaction of a ketone and a phenol in the presence of an ion-exchange resin.Type: GrantFiled: June 13, 1996Date of Patent: July 21, 1998Assignee: General Electric CompanyInventor: Gaylord Michael Kissinger
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Patent number: 5777180Abstract: An improved process for the production of bisphenols is presented in which ketones and phenols are reacted in the presence of an acidic cationic exchange resin catalyst and a mercaptan cocatalyst. Prior to the reaction, alkyl alcohol is removed from the ketone stream. Cocatalyst is withdrawn from the reactor so that cocatalyst derivatives such as disulphide ions can be removed from the presence of the catalyst thereby reducing the possibility of catalyst poisoning.Type: GrantFiled: December 18, 1996Date of Patent: July 7, 1998Assignee: Shell Oil CompanyInventors: Raymond Lawrence June, Robert Lawrence Blackbourn, Edgar Donald Allan, James Laurel Buechele
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Patent number: 5698600Abstract: The invention relates to the synthesis of bisphenols from monophenols and carbonyl compounds such as aldehydes and ketones with concentrated mineral acids such as hydrochloric acid and/or hydrogen chloride gas as acid catalysts and a mercaptan as cocatalyst, which is fixed by an ion-pair bond to a matrix insoluble in the reaction medium.Type: GrantFiled: October 15, 1996Date of Patent: December 16, 1997Assignee: Bayer AGInventors: Claus Wulff, Gerhard Fennhoff, Alfred Eitel
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Patent number: 5589517Abstract: A modified strongly acidic ion exchange resin of a sulfonic acid type is disclosed. Modification is conducted by ionically binding a particular N,N-di-substituted mercaptoalkylamine to a strongly acidic ion exchange resin of a sulfonic acid type. The N,N-di-substituted mercaptoalkylamine is specifically represented by the following formulae: ##STR1## wherein R.sup.1 represents hydrogen or a C.sub.1-6 alkyl group, R.sup.2 and R.sup.3 independently represent a C.sub.1-10 alkyl group, a and b denote 0-3, respectively, a+b denotes 2 or 3, and m denotes 4 or 5. The modified ion exchange resin makes an improved catalyst in the preparation of a bisphenol by the condensation reaction of a phenol with a ketone.Type: GrantFiled: April 6, 1995Date of Patent: December 31, 1996Assignee: Mitsubishi Chemical CorporationInventors: Takahiro Sugawara, Michi Watanabe, Naoko Sumitani, Miwa Shirasaki, Toshitaka Suzuki
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Patent number: 5502016Abstract: In the process of bisphenol-A systhesis a method for controlling the water content of the resultant cation-exchanger bed wherein an acid ion-exchanger resin in the form of a sulphonated styrene-divinylbenzene copolymer is washed with phenol and the resulted washing is contacted with a basic ion-exchanger resin. Water is removed from the washing by distillation, and the dewatered phenol is recycled to wash the cation-exchanger bed. The catalyst bed is then washed with a mixture of phenol acetone and water, and this washing is contacted with the basic ion-exchange resin and recycled to wash the cation exchanger bed so as to obtain the desired moisture content.Type: GrantFiled: May 23, 1994Date of Patent: March 26, 1996Assignees: Instytut Ciezkiej Syntezy Organicznej Blachownia, Zaklady Chemiczne BlachowniaInventors: Maciej Kiedik, Andrzej Krueger, Jo/ zef Ko t, Antoni Korek, Wojciech Balcerowiak, Jacek Hetper, Maria Majchrzak, Jan Niedziela, Ryszard Kosciuk, Anna Rzodeczko, Jerzy Mro/ z, Zbigniew Swiderski
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Patent number: 5475155Abstract: 4,4'-Dihydroxy-alpha-alkylstilbenes of high purity are prepared by reacting at a temperature of from about -20.degree. C. to about 20.degree. C. a mixture of (1) at least one alpha-haloketone, (2) at least one phenolic hydroxyl-containing compound or alkoxy-containing aromatic compound, and (3) at least one strong protonic acid or Lewis acid; such that the mole ratio of phenolic hydroxyl-containing compound or alkoxy-containing aromatic compound:alpha-haloketone(s) is from 0.1:1 to 1.9:1, and the mole ratio of phenolic hydroxyl-containing compound or alkoxy-containing aromatic compound:alpha-haloketone(s):strong protonic acid or Lewis acid is from about 0.1:1:0.0026 to about 1.9:1:0.95. The high purity 4,4'-dihydroxy-alpha-alkylstilbenes are useful for the advancement of epoxy resins, for the preparation of phenoxy resins and for the preparation of epoxy resins.Type: GrantFiled: January 18, 1995Date of Patent: December 12, 1995Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Maria I. Villarreal, David A. Carr
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Patent number: 5463140Abstract: A process for the condensation of an aldehyde or ketone starting material with a phenol, unsubstituted in the 4-position, comprises reacting the aldehyde or ketone starting material with the phenol in a reaction mixture in the presence of a soluble or insoluble mercaptosulfonic acid compound under conditions sufficient to bring about formation of a geminal bisphenolic moiety at each aldehyde or ketone moiety in the starting material. A miscible mercaptosulfonic acid compound is characterized by the formula(HS).sub.a -.theta.-(SO.sub.3 H).sub.bor a precursor thereof, wherein .theta. is an alkylene, cycloaliphatic, arylene, alkylenearylene, alkylenecycloaliphatic, alkylenearyl, heterocyclic or alkyleneheterocyclic residue.Type: GrantFiled: August 31, 1994Date of Patent: October 31, 1995Assignee: The Dow Chemical CompanyInventors: Richard M. Wehmeyer, Marlin E. Walters, Emmett L. Tasset, Steven L. Brewster
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Patent number: 5455282Abstract: The invention relates to repeatedly regeneratable ion exchanger resins with a thin covering of alkyl-SH groups.Type: GrantFiled: January 30, 1995Date of Patent: October 3, 1995Assignee: Bayer AktiengesellschaftInventors: Klaus Berg, Georg Malamet, Franz Backes, Alfred Eitel, Claus Wulff