Preparing From A Phenol And An Aldehyde Or Ketone Patents (Class 568/727)
  • Patent number: 6620939
    Abstract: 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: Grant
    Filed: September 18, 2001
    Date of Patent: September 16, 2003
    Assignee: General Electric Company
    Inventors: Jimmy Lynn Webb, James Lawrence Spivack
  • Patent number: 6610889
    Abstract: Methods and compositions are provided for the direct catalytic asymmetric aldol reaction of aldehydes with donor molecules selected from ketones and nitroalkyl compounds. The reactions employ as catalyst a Group 2A or Group 2B metal complex of a ligand of formula I, as defined further herein.
    Type: Grant
    Filed: October 31, 2001
    Date of Patent: August 26, 2003
    Assignee: The Board of Trustees of the Leland Stanford Junior University
    Inventors: Barry M. Trost, Hisanaka Ito
  • Patent number: 6586640
    Abstract: 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: Grant
    Filed: June 20, 2002
    Date of Patent: July 1, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Ralph Birchard Lloyd, Qun Sun, Mark Andrew Harmer, Edward George Howard, Jr.
  • Patent number: 6534686
    Abstract: 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: Grant
    Filed: September 18, 2001
    Date of Patent: March 18, 2003
    Assignee: General Electric Company
    Inventors: Jimmy Lynn Webb, James Lawrence Spivack
  • Publication number: 20030045758
    Abstract: 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: Application
    Filed: June 26, 2002
    Publication date: March 6, 2003
    Applicant: General Electric Company
    Inventors: William Patrick Flanagan, Cheryl Lynn Sabourin, James Lawrence Spivack
  • Publication number: 20030028055
    Abstract: The present invention is a high-quality bisphenol A wherein the content of sodium is not more than 80 ppb and the content of each element of the group A consisting of iron, nickel, chromium, manganese, lead, and molybdenum is not more than 50 ppb, or a high-quality bisphenol A containing an organic compound such as 9,9′-dimethylxanthene, 2-(4-hydroxyphenyl)-2,4,4-trimethylchroman, 2,2,4-trimethyl-chromene, etc., in an amount of lower than a specific amount, and a preparation process of these high-quality bisphenol A. When an aromatic polycarbonate is prepared using the high-quality bisphenol of the invention, an aromatic polycarbonate which is not colored at the preparation thereof and molding the polycarbonate.
    Type: Application
    Filed: August 2, 2001
    Publication date: February 6, 2003
    Inventors: Hideaki Nakamura, Masamitsu Inomata, Toshizumi Miura
  • Patent number: 6492566
    Abstract: The present invention discloses an improved process for the preparation of dihydroxydiphenylmethanes by reacting phenol over a microporous alumino-silicate zeolite catalyst composite material in the presence of a condensing agent and a solvent at a temperature in the range of 5 to 200° C. for a period between 0.1 to 24 hours at autogeneous pressure and separating the dihydroxydiphenylmethanes by any conventional method.
    Type: Grant
    Filed: January 19, 2000
    Date of Patent: December 10, 2002
    Assignee: Council of Scientific and Industrial Research
    Inventors: Anand Pal Singh, Sharda Dagade
  • Patent number: 6486364
    Abstract: 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: Grant
    Filed: December 19, 2000
    Date of Patent: November 26, 2002
    Assignee: General Electric Company
    Inventor: James Lawrence Spivack
  • Patent number: 6486363
    Abstract: 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: Grant
    Filed: July 12, 1996
    Date of Patent: November 26, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Berg, Hans-Josef Buysch, Alfred Eitel, Gerhard Fennhoff, Georg Malamet, Clauss Wulff
  • Patent number: 6486222
    Abstract: 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: Grant
    Filed: April 9, 2001
    Date of Patent: November 26, 2002
    Assignee: General Electric Company
    Inventors: Gaylord M. Kissinger, Sheldon J. Shafer, Harish R. Acharya, Rudy Francois Alain J. Peemans, Eduard H. Schlarmann
  • Patent number: 6465697
    Abstract: 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: Grant
    Filed: April 13, 2001
    Date of Patent: October 15, 2002
    Assignee: Resolution Performance Products LLC
    Inventors: David Palmer, Pui Kwan Wong
  • Publication number: 20020142923
    Abstract: Hindered tert-butylphenolic antioxidant compositions characterized by a low level of volatile and undesirable single-ring tert-butylphenolic antioxidants and a high level of non-volatile multi-ring (or methylene bridged) tert-butylphenolic antioxidants are obtained by reacting a specific mixture of ultra pure ortho-tert-butylphenol (OTBP), ultra pure 2,6-di-tert-butylphenol (DTBP) and formaldehyde in a solvent in the presence of catalyst. These antioxidants are further characterized by having a low level of 2,6-di-tert-butylphenol, low levels of ortho-tert-butylphenol, and trace levels of 2,4,6-tri-tert-butylphenol.
    Type: Application
    Filed: March 8, 2002
    Publication date: October 3, 2002
    Inventor: Vincent J. Gatto
  • Publication number: 20020123656
    Abstract: 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: Application
    Filed: December 19, 2000
    Publication date: September 5, 2002
    Applicant: General Electric Company
    Inventor: James Lawrence Spivack
  • Patent number: 6429343
    Abstract: 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: Grant
    Filed: August 21, 2001
    Date of Patent: August 6, 2002
    Assignee: Idemitsu Petrochemical Co., Ltd.
    Inventor: Masahiro Iwahara
  • Patent number: 6414200
    Abstract: 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: Grant
    Filed: December 19, 2000
    Date of Patent: July 2, 2002
    Assignee: General Electric Company
    Inventors: James Lawrence Spivack, Jimmy Lynn Webb, Victoria Jean Eddy-Helenek, Joseph Richard Wetzel
  • Patent number: 6329556
    Abstract: 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: Grant
    Filed: November 29, 2000
    Date of Patent: December 11, 2001
    Assignee: Nippon Steel Chemical Co., Ltd.
    Inventors: Katsuhiko Sakura, Shingo Ueda, Genki Takeuchi, Shyouta Shirasaka, Toshikazu Maruyama, Yasuharu Hukuda, Taketoshi Kitoh, Morio Kimura
  • Patent number: 6326461
    Abstract: This invention is directed to a method of preparing a natural resin by liquefying wood, bark, forest residues, wood industry residues, or other biomass using rapid destructive distillation (fast pyrolysis). Fast pyrolysis produces both vapors and char from biomass, and following removal of the char from the product vapors, a liquid pitch product is recovered and processed by distillation, evaporation, or a combination thereof, in order to obtain a natural resin which may be in either liquid or solid form. The natural resin comprises a total phenolic content from about 30% to about 80% (w/w), and is a highly-reactive ligninic compound that has been found to be suitable for use within resin formulations without requiring any further extraction or fractionation procedures. Resins comprising up to 60% natural resin have been prepared and tested in board production and found to exhibit similar properties associated with commercially available resins.
    Type: Grant
    Filed: July 29, 1999
    Date of Patent: December 4, 2001
    Assignee: Ensyn Group, Inc.
    Inventors: Regi Giroux, Barry Freel, Robert Graham
  • Patent number: 6307111
    Abstract: 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: Grant
    Filed: November 12, 1999
    Date of Patent: October 23, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Fennhoff, Hans-Josef Buysch, Gerd Fengler
  • Patent number: 6303835
    Abstract: 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: Grant
    Filed: September 11, 2000
    Date of Patent: October 16, 2001
    Assignee: General Electric Company
    Inventors: Sheldon Jay Shafer, Eric James Pressman, Julia Lam Lee
  • Patent number: 6300528
    Abstract: 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: Grant
    Filed: April 3, 2000
    Date of Patent: October 9, 2001
    Assignee: General Electric Company
    Inventors: Gerrit Op Den Dries, Martin Jaco Soeters, Marcellinus Adrianus Klaverveld, Eduard Hendricus Schlarmann, Guido Theodorus Fridiswidus Maria Van Dooremal
  • Patent number: 6294702
    Abstract: 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: Grant
    Filed: December 13, 1999
    Date of Patent: September 25, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Fennhof, Hans-Josef Buysch, Gerd Fengler, Tony van Osselaer
  • Patent number: 6288284
    Abstract: 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: Grant
    Filed: July 3, 2000
    Date of Patent: September 11, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rob Eek, Kaspar Hallenberger, Christine Mendoza-Frohn, Georg Ronge, Gerhard Fennhoff, Domien Sluyts, Werner Verhoeven
  • Patent number: 6245951
    Abstract: 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: Grant
    Filed: October 12, 1999
    Date of Patent: June 12, 2001
    Assignee: General Electric Company
    Inventors: Rudy Peemans, Jan-Peter Visser, Hendrik Herman Caré, Edwin Van Der Schuit, Robbert Vos
  • Patent number: 6229037
    Abstract: The invention provides a polyorganosiloxane catalyst with both of a sulfonic acid group-containing hydrocarbon group and a mercapto group-containing hydrocarbon group, wherein the total amount of the sulfonic acid group-containing hydrocarbon group and the mercapto group-containing hydrocarbon group is within a range of 0.3 to 2.0 &mgr;mol per unit surface area (1 m2) of the polyorganosiloxane catalyst. The catalyst of the invention is highly active for the reaction to produce bisphenol A from acetone and phenol, with the deterioration of the catalyst under extreme suppression.
    Type: Grant
    Filed: April 4, 2000
    Date of Patent: May 8, 2001
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Tsuneyuki Okubo, Kazutoshi Matsu, Takao Araki, Toshihiro Takai
  • Patent number: 6211417
    Abstract: 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: Grant
    Filed: July 12, 1999
    Date of Patent: April 3, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerd Fengler, Hans-Josef Buysch, Frieder Heydenreich, Rob Eek, Gerhard Fennhoff
  • Patent number: 6203612
    Abstract: 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: Grant
    Filed: March 30, 2000
    Date of Patent: March 20, 2001
    Assignee: General Electric Company
    Inventors: Rudy Peemans, Jan Huibert Weijland, Mourice Van Sintemaartensdijk
  • Patent number: 6201160
    Abstract: Alcohols are prepared by the catalytic hydrogenation of the corresponding carbonyl compounds at elevated temperatures and at superatmospheric pressure in the liquid phase by a process in which the catalyst used contains copper on an SiO2-containing carrier in the presence or absence of one or more of the elements magnesium, barium, zinc and chromium.
    Type: Grant
    Filed: November 19, 1996
    Date of Patent: March 13, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Brudermüller, Matthias Irgang, Martin Schmidt-Radde, Franz Merger, Tom Witzel, Detlef Kratz, Eckehard Danz, Arnold Wittwer, Michael Hesse, Manfred Sauerwald, Cristina Freire Erdbrügger
  • Patent number: 6191316
    Abstract: 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: Grant
    Filed: November 12, 1999
    Date of Patent: February 20, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Fennhoff, Hans-Josef Buysch, Gerd Fengler
  • Patent number: 6143856
    Abstract: A phenolic-rich pyrolysis oil is produced by pyrolysing lignocellulosic material at a temperature of no more than about 550.degree. C under an absolute pressure of no more than about 50 kPa to produce pyrolysis vapors, and condensing the pyrolysis vapors to obtain a condensate consisting of a phenolic-rich pyrolysis oil having a dew point of about 65 to about 75.degree. C. under an absolute pressure of about 15 to about 20 kPa. Such a phenolic-rich pyrolysis can be directly used in making phenol-formaldehyde resol resins.
    Type: Grant
    Filed: February 5, 1999
    Date of Patent: November 7, 2000
    Assignee: Pyrovac Technologies Inc.
    Inventors: Christian Roy, Xiao Lu, Hooshang Pakdel
  • Patent number: 6084136
    Abstract: This invention relates to a process for the production of tetrabromobisphenol-A by the bromination of bisphenol-A, which process features: (a) feeding to a reaction mass (i) bisphenol-A and (ii) a stream of gaseous bromine, the gaseous stream having a Reynold's No. .gtoreq.40,000; (b) the reaction mass containing from about 50 to about 20,000 ppm unreacted bromine and less than 20 wt % HBr; and (c) the reaction mass having precipitated therefrom tetrabromobisphenol-A, all of (a)(ii), (b) and (c) occurring during the bisphenol-A feed.
    Type: Grant
    Filed: June 11, 1998
    Date of Patent: July 4, 2000
    Assignee: Albmarle Corporation
    Inventors: Richard A. Holub, Steven R. Alferi, Bonnie G. McKinnie, Hassan Y. Elnagar
  • Patent number: 6011184
    Abstract: 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: Grant
    Filed: April 6, 1998
    Date of Patent: January 4, 2000
    Assignee: General Electric Company
    Inventors: Johan Adrianus Aarssen, Gerrit Op Den Dries, Ad Nieuwlaat, Marcel Vieveen, Rudy Francois Alain Joseph Peemans
  • Patent number: 6002051
    Abstract: Novel compounds of the general formula ##STR1## wherein each R.sub.1 is independently a tertiary alkyl group containing from 4 to about 8 carbon atoms and each of X, Y and Z is independently hydrogen or a hydrocarbon-based group, provided at least one of X, Y and Z is an aliphatic hydrocarbon group containing at least 7 carbon atoms, and wherein R.sub.1 is different from the at least one of X, Y and Z that is an aliphatic hydrocarbon group containing at least 7 carbon atoms, R.sub.2 is an alkylene or alkylidene group, and n is a number ranging from zero to about 4. Also disclosed are methods for preparing novel phenolic compounds, organic compositions, including lubricants based on oils of lubricating viscosity and fuels based on normally liquid fuels and additive concentrates containing the novel phenolic compounds of this invention.
    Type: Grant
    Filed: October 16, 1992
    Date of Patent: December 14, 1999
    Assignee: The Lubrizol Corporation
    Inventors: Louis Burjes, Calvin W. Schroeck
  • Patent number: 6002050
    Abstract: This invention relates to a process for the production of tetrabromobisphenol-A, which process features: a water and water miscible solvent reaction medium; a relatively high reaction temperature; and the presence, in the reaction medium, of unreacted Br.sub.2 during the feed of bisphenol-A to the reactor.
    Type: Grant
    Filed: September 8, 1998
    Date of Patent: December 14, 1999
    Assignee: Albemarle Corporation
    Inventor: Bonnie G. McKinnie
  • Patent number: 5959159
    Abstract: A process for resolving racemic diesters of (R,S)(.+-.)-5-hydroxy-3-(4'-hydroxyphenyl)-1,1,3-trimethylindane is disclosed. The process utilizes a microbial enzyme derived from Chromobacterium viscosum to catalyze the enantioselective and regioselective hydrolysis of the (S)(-)-enantiomer of the racemic mixture to its corresponding monoester at a faster rate than the (R)(+)-enantiomer. A substantially pure (S)(-)-indane monoester is thereby formed, while the (R)(+)-indane diester remains unreacted. The (S)(-)-monoester and the (R)(+)-diester can then be hydrolyzed using conventional techniques to form optically active (R)(+)- and (S)(-)-5-hydroxy-3-(4'-hydroxyphenyl)-1,1,3-trimethylindane enantiomers for use as monomers in the synthesis of chiral polymers.
    Type: Grant
    Filed: October 24, 1997
    Date of Patent: September 28, 1999
    Assignee: Molecular OptoElectronics Corporation
    Inventors: Romas Joseph Kazlauskas, Xiaoming Zhang
  • Patent number: 5874645
    Abstract: A process which includes the step of heating a compound of Formula (I): ##STR1## wherein R.sup.1 is a hydroxyphenyl group or a group of Formula (II): ##STR2## and R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently in each occurrence H or a C.sub.1-10 alkyl group; to a temperature in the range of from 100.degree. C. to 400.degree. C. under reaction conditions sufficient to form one or more 4,4'-dihydroxy-alpha-substituted stilbenes.
    Type: Grant
    Filed: April 25, 1997
    Date of Patent: February 23, 1999
    Assignee: The Dow Chemical Company
    Inventors: Anthony P. Haag, Thomas A. Chamberlin, Robert E. Hefner, Jr., David A. Carr
  • Patent number: 5874644
    Abstract: 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: Grant
    Filed: April 12, 1996
    Date of Patent: February 23, 1999
    Inventor: Ben Gammill
  • Patent number: 5856589
    Abstract: 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: Grant
    Filed: August 8, 1997
    Date of Patent: January 5, 1999
    Assignee: General Electric Company
    Inventor: Michael J. Cipullo
  • Patent number: 5789628
    Abstract: A process for the production of 2,2'-bis(4-hydroxyphenyl)propanes by reacting the corresponding phenols and carbonyl compounds in the presence of organopolysiloxanes containing sulphonate and mercapto groups and acting as a catalyst, consisting of units of the formula?O.sub.3/2 --Si--R.sup.1 --SO.sub.3 --!.sub.x M.sup.x+ (I),wherein R.sup.1 is a linear or branched alkylene group having 1 to 12 C atoms, a cycloalkylene group having 5 to 8 C atoms or a unit of the formulae ##STR1## and units of the formulaO.sub.3/2 --Si--R.sup.
    Type: Grant
    Filed: September 20, 1996
    Date of Patent: August 4, 1998
    Assignee: Degussa Aktiengesellschaft
    Inventors: Emmanuel Auer, Stefan Wieland, Hans Lansink-Rotgerink, Hauke Jacobsen, Heike Riedemann
  • Patent number: 5786522
    Abstract: An integrated process for the preparation and recovery of BPA in pure form utilizes a series of steps to crystallize pure BPA of improved color stability and recycle separated impurities to improve overall yields. The principal impurity recycled to the process is o,p-BPA which functions as a color stabilizer in the product and in polycarbonate resins prepared from the BPA.
    Type: Grant
    Filed: September 13, 1996
    Date of Patent: July 28, 1998
    Assignee: General Electric Company
    Inventor: Michael J. Cipullo
  • Patent number: 5783733
    Abstract: 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: Grant
    Filed: June 13, 1996
    Date of Patent: July 21, 1998
    Assignee: General Electric Company
    Inventor: Gaylord Michael Kissinger
  • Patent number: 5780690
    Abstract: The invention relates to a process for the synthesis of bis-(4-hydroxyphenyl)-alkanes on ion-exchange resins or mixtures of ion-exchange resins which are modified with alkyl-SH groups, wherein the monophenols and carbonyl compounds to be used have first been purified to remove substances which can transfer alkyl groups.
    Type: Grant
    Filed: April 8, 1997
    Date of Patent: July 14, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Berg, Gerhard Fennhoff, Ralf Pakull, Hans-Josef Buysch, Bernhard Wehrle, Alfred Eitel, Claus Wulff, Jurgen Kirsch
  • Patent number: 5777180
    Abstract: 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: Grant
    Filed: December 18, 1996
    Date of Patent: July 7, 1998
    Assignee: Shell Oil Company
    Inventors: Raymond Lawrence June, Robert Lawrence Blackbourn, Edgar Donald Allan, James Laurel Buechele
  • Patent number: 5723691
    Abstract: In the preparation of bisphenol-A by condensation of phenol with acetone in the presence of an acidic ion-exchange resin catalyst, pretreatment of the catalyst to render it free of acidic oligomers which are detrimental to the preparation of bisphenol-A entails washing the catalyst resin with deionized water until the washings show a specific conductance of less than 50 micromho/cm at 25.degree. C.
    Type: Grant
    Filed: August 31, 1995
    Date of Patent: March 3, 1998
    Assignee: General Electric Company
    Inventors: Michael John Cipullo, Eric James Pressman
  • Patent number: 5698600
    Abstract: 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: Grant
    Filed: October 15, 1996
    Date of Patent: December 16, 1997
    Assignee: Bayer AG
    Inventors: Claus Wulff, Gerhard Fennhoff, Alfred Eitel
  • Patent number: 5679312
    Abstract: A reactive stripping process for continuously carrying out chemical reactions while separating the reactants from the reaction products is provided. The process comprises passing liquid reactants and an inert stripping gaseous stream in a reactor column (1) having a plurality of perforated trays (2) provided therein and interconnected by a plurality of downcomers (3), screens (4 and 5) provided on the trays (2) and the top openings of the downcomers (3). The trays (2) and downcomers (3) are associated with the screens (4 and 5) to form a chamber optionally provided with a solid particulate or liquid catalyst (6) therein. A reactive stripping apparatus for performing such a process is also provided. According to the invention, at least one reaction product and the reaction mixture having different boiling points can be separated in order that chemical reactions proceed continuously as desired.
    Type: Grant
    Filed: October 30, 1995
    Date of Patent: October 21, 1997
    Assignees: China Petro-Chemical Corporation, Tianjin University
    Inventors: Shiyi Jin, Jitang Yuan, Zongli Zhang, Huisheng Lu, Lianshun Wang, Jinzhu Yin
  • Patent number: 5648561
    Abstract: High purity and ultrapure bisphenol A is prepared in a novel process.
    Type: Grant
    Filed: October 11, 1995
    Date of Patent: July 15, 1997
    Assignees: China Petro-Chemical Corporation, Tianjin University
    Inventors: Qiu Tan, Minhua Zhang, Shenbo Yu, Zongzhang Liu, Shenghua Qian, Chuanzhao Li
  • Patent number: 5631338
    Abstract: The present invention provides a process for preparing bisphenol A with a high conversion and selectivity by reacting phenol with acetone in the presence of both a polyorganosiloxane having a mercapto group-containing hydrocarbon group and an acid. It is preferable that the polyorganosiloxane having a mercapto group-containing hydrocarbon group and the acid is a polyorganosiloxane having both a mercapto group-containing hydrocarbon group and a sulfonic acid group.
    Type: Grant
    Filed: July 11, 1995
    Date of Patent: May 20, 1997
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Kaoru Inoue, Tuneyuki Ohkubo, Takashi Terajima
  • Patent number: 5629456
    Abstract: A fluorene derivative of high purity is produced by reacting fluorenone with phenoxyethanol in the presence of a sulfuric acid-thiol catalyst system, dissolving the reaction mixture in a lower aliphatic alcohol and adding water to the resulting solution for precipitation of 9,9-bis(4-(2-hydroxyethoxy)phenyl)fluorene [fluorene derivative]. A fluorene derivative of still higher purity is obtained by recrystallization from a lower aliphatic alcohol.In accordance with this invention, a fluorene derivative can be produced advantageously on a commercial scale without incurring any appreciable loss of fluorenone, in good yield, with high efficiency and in a reduced production time.
    Type: Grant
    Filed: December 7, 1994
    Date of Patent: May 13, 1997
    Assignee: Osaka Gas Company Limited
    Inventors: Mitsuaki Yamada, Katsuhide Okimi, Katsuyuki Takahashi, Norio Nagano
  • Patent number: 5616816
    Abstract: Novel compounds of the general formula ##STR1## wherein each R.sub.1 is independently a tertiary alkyl group containing from 4 to about 8 carbon atoms and each of X, Y and Z is independently hydrogen or a hydrocarbon-based group, provided at least one of X, Y and Z is an aliphatic hydrocarbon group containing at least 7 carbon atoms, and wherein R.sub.1 is different from the at least one of X, Y and Z that is an aliphatic hydrocarbon group containing at least 7 carbon atoms, R.sub.2 is an alkylene or alkylidene group, and n is a number ranging from zero to about 4. Also disclosed are methods for preparing novel phenolic compounds, organic compositions, including lubricants based on oils of lubricating viscosity and fuels based on normally liquid fuels and additive concentrates containing the novel phenolic compounds of this invention.
    Type: Grant
    Filed: June 1, 1995
    Date of Patent: April 1, 1997
    Assignee: The Lubrizol Corporation
    Inventors: Louis Burjes, Calvin W. Schroeck
  • Patent number: 5589517
    Abstract: 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: Grant
    Filed: April 6, 1995
    Date of Patent: December 31, 1996
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Takahiro Sugawara, Michi Watanabe, Naoko Sumitani, Miwa Shirasaki, Toshitaka Suzuki